# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? #================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_volume ? _journal_year ? loop_ _publ_author_address ; School of Chemistry and Environment South China Normal University Guangzhou 510006 P.R. China ; #TrackingRef '- xx.cif' #==================================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Hong Deng School of Chemistry and Environment South China Nomal University Guangzhou 510006 P. R. China ; _publ_contact_author_email dh@scnu.edu.cn _publ_contact_author_fax '86 20 33381880' _publ_contact_author_phone '86 20 33381880' _publ_contact_letter ; Dear Sir or Madam: Please consider this CIF as supplmentary data for a manuscript submitted to CrystEngComm. Deng Hong ; _publ_requested_coeditor_name ? #======================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; ? ; _publ_contact_author_name 'Hong Deng' _publ_author_name 'Hong Deng' data_1 _database_code_depnum_ccdc_archive 'CCDC 819503' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 Cd N6 O2, H2 O' _chemical_formula_sum 'C13 H12 Cd N6 O3' _chemical_formula_weight 412.69 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 C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.252(3) _cell_length_b 8.9154(11) _cell_length_c 14.8686(18) _cell_angle_alpha 90.00 _cell_angle_beta 109.9530(10) _cell_angle_gamma 90.00 _cell_volume 3021.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.805 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616.0 _exptl_absorpt_coefficient_mu 1.469 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.650 _exptl_absorpt_correction_T_max 0.683 _exptl_absorpt_process_details 'Apex2 (Bruker, 2005)' _exptl_special_details ; In the original refinement the lattice water molecule showed significantly elongated thermal ellipsoids indicating disorder. The molecule was thus refined as being disordered over two sites in a ratio of 0.65(2): 0.35(2). ; _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 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 7575 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.20 _reflns_number_total 2729 _reflns_number_gt 2189 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker, 2005)' _computing_cell_refinement 'Apex2 (Bruker, 2005)' _computing_data_reduction 'Apex2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL 6.12 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.12' _computing_molecular_graphics 'SHELXTL 6.12' _computing_publication_material 'SHELXTL 6.12' _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^)+(0.0714P)^2^+13.0727P] 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 2725 _refine_ls_number_parameters 218 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1320 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2063(3) 0.5878(8) -0.0601(5) 0.0524(16) Uani 1 1 d . . . H1 H 0.2382 0.5327 -0.0632 0.063 Uiso 1 1 calc R . . C2 C 0.1913(4) 0.7166(9) -0.1136(6) 0.073(2) Uani 1 1 d . . . H2 H 0.2121 0.7485 -0.1523 0.087 Uiso 1 1 calc R . . C3 C 0.1444(5) 0.7960(9) -0.1077(7) 0.087(3) Uani 1 1 d . . . H3 H 0.1330 0.8845 -0.1422 0.105 Uiso 1 1 calc R . . C4 C 0.1140(4) 0.7450(9) -0.0506(7) 0.073(2) Uani 1 1 d . . . H4 H 0.0818 0.7982 -0.0469 0.088 Uiso 1 1 calc R . . C5 C 0.1316(3) 0.6145(7) 0.0010(4) 0.0456(15) Uani 1 1 d . . . C6 C 0.1000(3) 0.5498(8) 0.0608(4) 0.0473(15) Uani 1 1 d . . . C7 C 0.0535(3) 0.6238(10) 0.0761(6) 0.065(2) Uani 1 1 d . . . H7 H 0.0420 0.7185 0.0503 0.078 Uiso 1 1 calc R . . C8 C 0.0246(4) 0.5544(14) 0.1302(7) 0.089(3) Uani 1 1 d . . . H8 H -0.0060 0.6030 0.1425 0.106 Uiso 1 1 calc R . . C9 C 0.0412(4) 0.4138(15) 0.1654(7) 0.096(3) Uani 1 1 d . . . H9 H 0.0210 0.3630 0.1992 0.115 Uiso 1 1 calc R . . C10 C 0.0883(4) 0.3496(12) 0.1496(6) 0.078(3) Uani 1 1 d . . . H10 H 0.1009 0.2560 0.1765 0.094 Uiso 1 1 calc R . . C11 C 0.1785(3) -0.0816(8) 0.2421(5) 0.0535(17) Uani 1 1 d . . . C12 C 0.1448(3) -0.1868(8) 0.2766(5) 0.0548(18) Uani 1 1 d . . . H12A H 0.1514 -0.2850 0.2540 0.066 Uiso 1 1 calc R . . H12B H 0.1038 -0.1630 0.2436 0.066 Uiso 1 1 calc R . . C13 C 0.1521(4) -0.2054(8) 0.3814(7) 0.067(2) Uani 1 1 d . . . Cd1 Cd 0.202534(17) 0.31208(5) 0.08104(3) 0.03652(19) Uani 1 1 d . . . N1 N 0.1778(2) 0.5376(5) -0.0043(3) 0.0409(11) Uani 1 1 d . . . N2 N 0.1172(2) 0.4139(7) 0.0977(4) 0.0506(14) Uani 1 1 d . . . N3 N 0.1582(3) 0.0193(7) 0.1747(4) 0.0611(16) Uani 1 1 d . . . N4 N 0.2028(2) 0.0993(6) 0.1698(4) 0.0495(13) Uani 1 1 d . . . N5 N 0.2521(2) 0.0490(7) 0.2416(4) 0.0553(15) Uani 1 1 d . . . N6 N 0.2383(2) -0.0596(6) 0.2852(4) 0.0506(13) Uani 1 1 d . . . O1 O 0.2023(3) -0.2043(5) 0.4349(4) 0.0640(14) Uani 1 1 d . . . O2 O 0.1082(3) -0.2194(8) 0.4010(5) 0.090(2) Uani 1 1 d . . . O1WA O 0.0111(7) 0.973(2) 0.342(3) 0.34(2) Uani 0.65(2) 1 d PU A 1 O1WB O 0.0326(10) 0.961(3) 0.530(3) 0.23(3) Uani 0.35(2) 1 d PU . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.069(4) 0.049(4) 0.047(4) 0.003(3) 0.031(3) -0.001(3) C2 0.105(7) 0.058(5) 0.059(5) 0.018(4) 0.032(5) -0.004(5) C3 0.123(8) 0.053(5) 0.084(7) 0.022(4) 0.033(6) 0.012(5) C4 0.082(6) 0.049(4) 0.088(6) 0.009(4) 0.027(5) 0.021(4) C5 0.047(3) 0.040(3) 0.041(3) -0.006(3) 0.005(3) 0.005(3) C6 0.040(3) 0.060(4) 0.040(3) -0.011(3) 0.010(3) 0.009(3) C7 0.050(4) 0.078(5) 0.062(5) -0.026(4) 0.013(4) 0.014(4) C8 0.061(5) 0.143(10) 0.071(6) -0.035(6) 0.034(5) 0.013(6) C9 0.065(5) 0.160(11) 0.082(7) 0.010(7) 0.049(5) 0.011(7) C10 0.065(5) 0.119(7) 0.062(5) 0.025(5) 0.037(4) 0.017(5) C11 0.058(4) 0.048(4) 0.056(4) 0.015(3) 0.020(3) 0.006(3) C12 0.047(4) 0.063(4) 0.052(4) 0.022(3) 0.013(3) 0.003(3) C13 0.061(5) 0.042(4) 0.103(7) 0.010(4) 0.032(5) -0.005(3) Cd1 0.0388(3) 0.0388(3) 0.0336(3) 0.00475(17) 0.01443(19) 0.00302(18) N1 0.050(3) 0.038(3) 0.037(3) -0.001(2) 0.018(2) 0.005(2) N2 0.046(3) 0.069(4) 0.041(3) 0.005(3) 0.020(2) 0.005(3) N3 0.069(4) 0.067(4) 0.044(3) 0.009(3) 0.014(3) -0.002(3) N4 0.053(3) 0.045(3) 0.060(4) 0.010(3) 0.032(3) -0.002(3) N5 0.055(3) 0.060(4) 0.058(4) -0.007(3) 0.028(3) -0.003(3) N6 0.053(3) 0.053(3) 0.043(3) 0.005(3) 0.014(3) 0.008(3) O1 0.072(4) 0.063(3) 0.058(3) 0.004(2) 0.024(3) -0.010(3) O2 0.064(4) 0.132(6) 0.091(5) 0.012(4) 0.049(3) -0.003(4) O1WA 0.086(12) 0.211(19) 0.67(6) -0.20(3) 0.07(2) -0.043(13) O1WB 0.085(16) 0.093(19) 0.43(6) 0.01(3) -0.03(2) -0.028(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 C1 N1 1.326(8) . ? C1 C2 1.374(10) . ? C1 H1 0.9300 . ? C2 C3 1.368(13) . ? C2 H2 0.9300 . ? C3 C4 1.378(13) . ? C3 H3 0.9300 . ? C4 C5 1.378(10) . ? C4 H4 0.9300 . ? C5 N1 1.339(8) . ? C5 C6 1.475(10) . ? C6 N2 1.336(8) . ? C6 C7 1.391(9) . ? C7 C8 1.380(13) . ? C7 H7 0.9300 . ? C8 C9 1.365(14) . ? C8 H8 0.9300 . ? C9 C10 1.368(12) . ? C9 H9 0.9300 . ? C10 N2 1.337(9) . ? C10 H10 0.9300 . ? C11 N3 1.311(8) . ? C11 N6 1.384(8) . ? C11 C12 1.448(9) . ? C12 C13 1.516(12) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 O2 1.201(9) . ? C13 O1 1.208(10) . ? Cd1 N4 2.310(5) . ? Cd1 N6 2.319(5) 4 ? Cd1 N1 2.344(5) . ? Cd1 N2 2.348(5) . ? Cd1 O1 2.374(5) 6 ? Cd1 O1 2.402(6) 4 ? N3 N4 1.318(8) . ? N4 N5 1.379(7) . ? N5 N6 1.272(7) . ? N6 Cd1 2.319(5) 4_545 ? O1 Cd1 2.374(5) 6_556 ? O1 Cd1 2.402(6) 4_545 ? O1WB O1WB 1.68(5) 5_576 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 123.6(7) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C3 C2 C1 117.2(8) . . ? C3 C2 H2 121.4 . . ? C1 C2 H2 121.4 . . ? C2 C3 C4 120.0(8) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 119.6(8) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 120.4(7) . . ? N1 C5 C6 116.9(5) . . ? C4 C5 C6 122.7(6) . . ? N2 C6 C7 121.4(7) . . ? N2 C6 C5 116.6(5) . . ? C7 C6 C5 122.0(7) . . ? C8 C7 C6 118.9(9) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C9 C8 C7 119.5(8) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 118.2(9) . . ? C8 C9 H9 120.9 . . ? C10 C9 H9 120.9 . . ? N2 C10 C9 123.6(9) . . ? N2 C10 H10 118.2 . . ? C9 C10 H10 118.2 . . ? N3 C11 N6 108.5(6) . . ? N3 C11 C12 127.3(7) . . ? N6 C11 C12 123.8(6) . . ? C11 C12 C13 123.6(6) . . ? C11 C12 H12A 106.4 . . ? C13 C12 H12A 106.4 . . ? C11 C12 H12B 106.4 . . ? C13 C12 H12B 106.4 . . ? H12A C12 H12B 106.5 . . ? O2 C13 O1 128.3(10) . . ? O2 C13 C12 117.3(8) . . ? O1 C13 C12 114.4(7) . . ? N4 Cd1 N6 92.0(2) . 4 ? N4 Cd1 N1 164.59(18) . . ? N6 Cd1 N1 90.60(18) 4 . ? N4 Cd1 N2 95.05(19) . . ? N6 Cd1 N2 91.6(2) 4 . ? N1 Cd1 N2 69.69(18) . . ? N4 Cd1 O1 100.92(18) . 6 ? N6 Cd1 O1 142.4(2) 4 6 ? N1 Cd1 O1 86.09(17) . 6 ? N2 Cd1 O1 121.75(19) . 6 ? N4 Cd1 O1 101.02(18) . 4 ? N6 Cd1 O1 77.31(19) 4 4 ? N1 Cd1 O1 94.37(17) . 4 ? N2 Cd1 O1 160.71(18) . 4 ? O1 Cd1 O1 65.6(2) 6 4 ? C1 N1 C5 119.3(6) . . ? C1 N1 Cd1 122.4(4) . . ? C5 N1 Cd1 118.2(4) . . ? C6 N2 C10 118.2(6) . . ? C6 N2 Cd1 118.1(4) . . ? C10 N2 Cd1 123.3(5) . . ? C11 N3 N4 108.2(6) . . ? N3 N4 N5 107.0(5) . . ? N3 N4 Cd1 129.3(4) . . ? N5 N4 Cd1 122.8(4) . . ? N6 N5 N4 109.4(5) . . ? N5 N6 C11 106.8(5) . . ? N5 N6 Cd1 128.2(4) . 4_545 ? C11 N6 Cd1 124.8(4) . 4_545 ? C13 O1 Cd1 106.6(5) . 6_556 ? C13 O1 Cd1 136.3(6) . 4_545 ? Cd1 O1 Cd1 114.4(2) 6_556 4_545 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.327 _refine_diff_density_min -0.646 _refine_diff_density_rms 0.120 data_2a _database_code_depnum_ccdc_archive 'CCDC 819504' #TrackingRef '- xx.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C13 H10 Cd N10), H0.48 O0.24, 2(H2 O)' _chemical_formula_sum 'C26 H24.48 Cd2 N20 O2.24' _chemical_formula_weight 877.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.742(5) _cell_length_b 8.9651(18) _cell_length_c 16.641(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.13(3) _cell_angle_gamma 90.00 _cell_volume 3366.2(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description piece _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.732 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1737.9 _exptl_absorpt_coefficient_mu 1.324 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.801 _exptl_absorpt_correction_T_max 0.853 _exptl_absorpt_process_details 'Apex2 (Bruker, 2005)' _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 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 12552 _diffrn_reflns_av_R_equivalents 0.0699 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 25.19 _reflns_number_total 3029 _reflns_number_gt 2522 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker, 2005)' _computing_cell_refinement 'Apex2 (Bruker, 2005)' _computing_data_reduction 'Apex2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL 6.12 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.12' _computing_molecular_graphics 'SHELXTL 6.12' _computing_publication_material 'SHELXTL 6.12' _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^)+(0.1078P)^2^+7.1505P] 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 2977 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0659 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1672 _refine_ls_wR_factor_gt 0.1563 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.10407(10) 0.5760(3) 0.05235(15) 0.0588(16) Uani 1 1 d G . . C2 C 0.05383(14) 0.6502(4) 0.0572(2) 0.083(3) Uani 1 1 d G . . H2 H 0.0400 0.7337 0.0237 0.100 Uiso 1 1 calc R . . C3 C 0.02424(15) 0.5996(5) 0.1120(3) 0.100(3) Uani 1 1 d G . . H3 H -0.0094 0.6493 0.1153 0.120 Uiso 1 1 calc R . . C4 C 0.04489(16) 0.4748(5) 0.1621(2) 0.091(3) Uani 1 1 d G . . H4 H 0.0251 0.4409 0.1988 0.110 Uiso 1 1 calc R . . C5 C 0.09513(17) 0.4006(4) 0.1573(2) 0.079(2) Uani 1 1 d G . . H5 H 0.1090 0.3170 0.1907 0.094 Uiso 1 1 calc R . . N1 N 0.12472(13) 0.4511(3) 0.10238(17) 0.0550(12) Uani 1 1 d G . . C6 C 0.13685(11) 0.6142(3) -0.00471(13) 0.0597(16) Uani 1 1 d G . . C7 C 0.11336(17) 0.7271(4) -0.0673(2) 0.094(3) Uani 1 1 d G . . H7 H 0.0777 0.7757 -0.0731 0.113 Uiso 1 1 calc R . . C8 C 0.1495(2) 0.7592(5) -0.1207(2) 0.114(4) Uani 1 1 d G . . H8 H 0.1371 0.8335 -0.1613 0.137 Uiso 1 1 calc R . . C9 C 0.2013(2) 0.6851(5) -0.1142(2) 0.096(3) Uani 1 1 d G . . H9 H 0.2235 0.7060 -0.1501 0.115 Uiso 1 1 calc R . . C10 C 0.21885(16) 0.5780(4) -0.0518(2) 0.0694(18) Uani 1 1 d G . . H10 H 0.2537 0.5258 -0.0466 0.083 Uiso 1 1 calc R . . N2 N 0.18844(12) 0.5448(3) 0.00202(17) 0.0590(13) Uani 1 1 d G . . C11 C 0.3592(3) 0.3216(7) 0.1609(4) 0.0561(15) Uani 1 1 d . . . C12 C 0.3621(4) 0.3321(8) 0.2509(4) 0.068(2) Uani 1 1 d . . . H12A H 0.4028 0.3516 0.2849 0.082 Uiso 1 1 calc R . . H12B H 0.3506 0.2369 0.2687 0.082 Uiso 1 1 calc R . . C13 C 0.3227(3) 0.4529(7) 0.2677(3) 0.0539(14) Uani 1 1 d . . . Cd1 Cd 0.213245(17) 0.34231(4) 0.09837(2) 0.0454(2) Uani 1 1 d . . . N3 N 0.3101(2) 0.3046(6) 0.0955(3) 0.0486(11) Uani 1 1 d . . . N4 N 0.3292(2) 0.2992(7) 0.0273(3) 0.0567(12) Uani 1 1 d . . . N5 N 0.3863(3) 0.3076(9) 0.0510(4) 0.0777(19) Uani 1 1 d . . . N6 N 0.4071(3) 0.3255(9) 0.1355(4) 0.081(2) Uani 1 1 d . . . N7 N 0.2661(2) 0.4746(6) 0.2209(3) 0.0531(11) Uani 1 1 d . . . N8 N 0.2478(2) 0.5908(6) 0.2558(3) 0.0554(13) Uani 1 1 d . . . N9 N 0.2915(3) 0.6357(6) 0.3203(3) 0.0574(13) Uani 1 1 d . . . N10 N 0.3403(3) 0.5522(7) 0.3297(3) 0.0637(14) Uani 1 1 d . . . O1W O 0.0308(4) 0.0771(12) 0.0745(9) 0.181(5) Uani 1 1 d . . . H1WA H 0.0496 0.0482 0.0364 0.272 Uiso 1 1 d R . . H1WB H 0.0594 0.1241 0.1171 0.272 Uiso 1 1 d R . . O2W O 0.0000 0.131(10) 0.2500 0.20(4) Uani 0.24 2 d SP . . H2WB H 0.0000 0.0357 0.2500 0.298 Uiso 0.24 2 d SPR . . H2WA H 0.0079 0.1854 0.2163 0.298 Uiso 0.12 1 d PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.057(3) 0.058(4) 0.054(3) -0.017(3) 0.006(3) 0.012(3) C2 0.080(5) 0.068(5) 0.083(5) -0.016(4) -0.001(5) 0.029(4) C3 0.057(4) 0.120(8) 0.123(7) -0.032(7) 0.029(5) 0.019(5) C4 0.075(5) 0.106(7) 0.106(6) -0.022(5) 0.049(5) -0.001(5) C5 0.079(5) 0.091(6) 0.075(4) -0.010(4) 0.037(4) 0.017(4) N1 0.059(3) 0.055(3) 0.053(3) -0.003(2) 0.020(2) 0.008(2) C6 0.071(4) 0.044(3) 0.055(3) 0.002(3) 0.007(3) 0.013(3) C7 0.119(7) 0.070(5) 0.076(5) 0.017(4) 0.003(5) 0.026(5) C8 0.197(13) 0.075(6) 0.074(5) 0.031(4) 0.046(7) 0.033(7) C9 0.160(10) 0.066(5) 0.068(5) 0.014(4) 0.047(6) 0.003(6) C10 0.095(5) 0.056(4) 0.065(4) 0.010(3) 0.036(4) 0.004(4) N2 0.080(4) 0.046(3) 0.049(3) 0.006(2) 0.019(3) 0.008(3) C11 0.051(3) 0.053(4) 0.057(3) -0.006(3) 0.007(3) 0.013(3) C12 0.079(5) 0.059(4) 0.055(4) -0.004(3) 0.003(3) 0.019(3) C13 0.061(3) 0.056(3) 0.044(3) 0.002(2) 0.015(3) 0.005(3) Cd1 0.0511(3) 0.0437(3) 0.0425(3) 0.00198(14) 0.0160(2) 0.00744(15) N3 0.048(3) 0.053(3) 0.045(2) -0.007(2) 0.015(2) 0.004(2) N4 0.052(3) 0.061(3) 0.056(3) -0.009(3) 0.015(2) 0.001(2) N5 0.048(3) 0.112(5) 0.073(4) -0.029(4) 0.018(3) 0.005(3) N6 0.049(3) 0.119(6) 0.070(4) -0.024(3) 0.009(3) 0.014(3) N7 0.064(3) 0.046(3) 0.052(2) -0.003(2) 0.021(2) 0.006(2) N8 0.066(3) 0.047(3) 0.057(3) -0.008(2) 0.025(3) 0.000(3) N9 0.069(3) 0.055(3) 0.049(3) -0.008(2) 0.021(3) 0.001(3) N10 0.074(3) 0.062(3) 0.052(3) -0.013(2) 0.015(2) 0.002(3) O1W 0.088(5) 0.119(7) 0.282(13) -0.014(8) -0.022(7) 0.004(5) O2W 0.13(4) 0.35(11) 0.07(3) 0.000 -0.04(3) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3900 . ? C1 N1 1.3900 . ? C1 C6 1.4438 . ? C2 C3 1.3900 . ? C2 H2 0.9300 . ? C3 C4 1.3900 . ? C3 H3 0.9300 . ? C4 C5 1.3900 . ? C4 H4 0.9300 . ? C5 N1 1.3900 . ? C5 H5 0.9300 . ? N1 Cd1 2.337(3) . ? C6 N2 1.3475 . ? C6 C7 1.4352 . ? C7 C8 1.4416 . ? C7 H7 0.9300 . ? C8 C9 1.3728 . ? C8 H8 0.9300 . ? C9 C10 1.3799 . ? C9 H9 0.9300 . ? C10 N2 1.3466 . ? C10 H10 0.9300 . ? N2 Cd1 2.372(3) . ? C11 N6 1.330(10) . ? C11 N3 1.334(8) . ? C11 C12 1.481(10) . ? C12 C13 1.512(10) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N10 1.328(8) . ? C13 N7 1.341(8) . ? Cd1 N9 2.317(5) 4_545 ? Cd1 N3 2.338(5) . ? Cd1 N7 2.356(5) . ? Cd1 N4 2.385(5) 7 ? N3 N4 1.350(7) . ? N4 N5 1.291(8) . ? N4 Cd1 2.385(5) 7 ? N5 N6 1.348(9) . ? N7 N8 1.330(7) . ? N8 N9 1.303(7) . ? N9 N10 1.346(8) . ? N9 Cd1 2.317(5) 4 ? O1W H1WA 0.9174 . ? O1W H1WB 0.9176 . ? O2W H2WB 0.8511 . ? O2W H2WA 0.8100 . ? 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 C2 C1 N1 120.0 . . ? C2 C1 C6 124.9 . . ? N1 C1 C6 115.0 . . ? C1 C2 C3 120.0 . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? N1 C5 C4 120.0 . . ? N1 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 N1 C1 120.0 . . ? C5 N1 Cd1 121.70(7) . . ? C1 N1 Cd1 118.15(8) . . ? N2 C6 C7 121.6 . . ? N2 C6 C1 119.8 . . ? C7 C6 C1 118.6 . . ? C6 C7 C8 114.6 . . ? C6 C7 H7 122.7 . . ? C8 C7 H7 122.7 . . ? C9 C8 C7 123.0 . . ? C9 C8 H8 118.5 . . ? C7 C8 H8 118.5 . . ? C8 C9 C10 116.7 . . ? C8 C9 H9 121.7 . . ? C10 C9 H9 121.7 . . ? N2 C10 C9 123.7 . . ? N2 C10 H10 118.1 . . ? C9 C10 H10 118.1 . . ? C10 N2 C6 120.3 . . ? C10 N2 Cd1 123.17(7) . . ? C6 N2 Cd1 115.97(8) . . ? N6 C11 N3 111.2(6) . . ? N6 C11 C12 123.0(6) . . ? N3 C11 C12 125.8(7) . . ? C11 C12 C13 113.3(5) . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? N10 C13 N7 111.6(6) . . ? N10 C13 C12 124.1(6) . . ? N7 C13 C12 124.2(6) . . ? N9 Cd1 N1 96.29(17) 4_545 . ? N9 Cd1 N3 97.1(2) 4_545 . ? N1 Cd1 N3 163.63(15) . . ? N9 Cd1 N7 90.38(18) 4_545 . ? N1 Cd1 N7 90.38(15) . . ? N3 Cd1 N7 80.09(17) . . ? N9 Cd1 N2 163.65(17) 4_545 . ? N1 Cd1 N2 70.33(6) . . ? N3 Cd1 N2 97.81(14) . . ? N7 Cd1 N2 98.82(15) . . ? N9 Cd1 N4 90.1(2) 4_545 7 ? N1 Cd1 N4 96.22(16) . 7 ? N3 Cd1 N4 93.20(18) . 7 ? N7 Cd1 N4 173.28(18) . 7 ? N2 Cd1 N4 82.29(16) . 7 ? C11 N3 N4 104.6(5) . . ? C11 N3 Cd1 125.7(4) . . ? N4 N3 Cd1 127.8(4) . . ? N5 N4 N3 109.8(5) . . ? N5 N4 Cd1 114.6(4) . 7 ? N3 N4 Cd1 126.6(4) . 7 ? N4 N5 N6 109.5(6) . . ? C11 N6 N5 105.0(6) . . ? N8 N7 C13 105.4(5) . . ? N8 N7 Cd1 127.9(4) . . ? C13 N7 Cd1 126.6(4) . . ? N9 N8 N7 108.5(5) . . ? N8 N9 N10 111.0(5) . . ? N8 N9 Cd1 123.8(4) . 4 ? N10 N9 Cd1 125.0(4) . 4 ? C13 N10 N9 103.4(5) . . ? H1WA O1W H1WB 105.2 . . ? H2WB O2W H2WA 127.3 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.19 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 2.303 _refine_diff_density_min -0.640 _refine_diff_density_rms 0.161 data_2b _database_code_depnum_ccdc_archive 'CCDC 819505' #TrackingRef '- xx.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C13 H10 N10 Zn), 3(H2 O)' _chemical_formula_sum 'C26 H26 N20 O3 Zn2' _chemical_formula_weight 797.45 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.854(5) _cell_length_b 8.9005(19) _cell_length_c 15.976(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.176(2) _cell_angle_gamma 90.00 _cell_volume 3087.6(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.715 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624.0 _exptl_absorpt_coefficient_mu 1.623 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.633 _exptl_absorpt_correction_T_max 0.688 _exptl_absorpt_process_details 'Apex2 (Bruker, 2005)' _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 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 7707 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.20 _reflns_number_total 2787 _reflns_number_gt 2403 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker, 2005)' _computing_cell_refinement 'Apex2 (Bruker, 2005)' _computing_data_reduction 'Apex2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL 6.12 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.12' _computing_molecular_graphics 'SHELXTL 6.12' _computing_publication_material 'SHELXTL 6.12' _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^)+(0.0331P)^2^+3.2091P] 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 2781 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0728 _refine_ls_wR_factor_gt 0.0692 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.32145(10) 0.4607(3) 0.26962(14) 0.0252(5) Uani 1 1 d . . . C2 C 0.36415(11) 0.3442(3) 0.25529(16) 0.0303(5) Uani 1 1 d . . . H2A H 0.3551 0.2490 0.2782 0.036 Uiso 1 1 calc R . . H2B H 0.4061 0.3717 0.2884 0.036 Uiso 1 1 calc R . . C3 C 0.35979(11) 0.3244(3) 0.16063(16) 0.0271(5) Uani 1 1 d . . . C4 C 0.10416(14) 0.3855(3) 0.1680(2) 0.0465(7) Uani 1 1 d . . . H4 H 0.1205 0.3022 0.2025 0.056 Uiso 1 1 calc R . . C5 C 0.05293(15) 0.4529(4) 0.1786(2) 0.0616(9) Uani 1 1 d . . . H5 H 0.0357 0.4170 0.2203 0.074 Uiso 1 1 calc R . . C6 C 0.02775(14) 0.5729(4) 0.1274(2) 0.0575(9) Uani 1 1 d . . . H6 H -0.0073 0.6196 0.1327 0.069 Uiso 1 1 calc R . . C7 C 0.05514(13) 0.6236(3) 0.0679(2) 0.0455(7) Uani 1 1 d . . . H7 H 0.0386 0.7052 0.0318 0.055 Uiso 1 1 calc R . . C8 C 0.10772(11) 0.5527(3) 0.06143(16) 0.0320(6) Uani 1 1 d . . . C9 C 0.14136(12) 0.6042(3) 0.00097(16) 0.0345(6) Uani 1 1 d . . . C10 C 0.11987(15) 0.7189(3) -0.0593(2) 0.0539(8) Uani 1 1 d . . . H10 H 0.0833 0.7683 -0.0629 0.065 Uiso 1 1 calc R . . C11 C 0.15320(18) 0.7584(4) -0.1136(2) 0.0607(9) Uani 1 1 d . . . H11 H 0.1397 0.8364 -0.1538 0.073 Uiso 1 1 calc R . . C12 C 0.20655(17) 0.6831(3) -0.1087(2) 0.0540(8) Uani 1 1 d . . . H12 H 0.2292 0.7075 -0.1461 0.065 Uiso 1 1 calc R . . C13 C 0.22562(14) 0.5707(3) -0.04724(17) 0.0402(6) Uani 1 1 d . . . H13 H 0.2619 0.5195 -0.0434 0.048 Uiso 1 1 calc R . . N1 N 0.26350(9) 0.4783(2) 0.21773(12) 0.0267(4) Uani 1 1 d . . . N2 N 0.24114(9) 0.5960(2) 0.25119(12) 0.0275(4) Uani 1 1 d . . . N3 N 0.28499(9) 0.6445(2) 0.32027(13) 0.0282(5) Uani 1 1 d . . . N4 N 0.33625(9) 0.5611(2) 0.33400(13) 0.0310(5) Uani 1 1 d . . . N5 N 0.30802(9) 0.3057(2) 0.09476(12) 0.0247(4) Uani 1 1 d . . . N6 N 0.32663(9) 0.2869(2) 0.02233(13) 0.0291(4) Uani 1 1 d . . . N7 N 0.38641(10) 0.2965(3) 0.04538(15) 0.0418(6) Uani 1 1 d . . . N8 N 0.40884(10) 0.3201(3) 0.13260(15) 0.0422(6) Uani 1 1 d . . . N9 N 0.13149(9) 0.4330(2) 0.11088(13) 0.0294(5) Uani 1 1 d . . . N10 N 0.19405(9) 0.5317(2) 0.00748(12) 0.0303(5) Uani 1 1 d . . . O2W O 0.5000 0.5767(8) 0.2500 0.169(3) Uani 1 2 d S . . H4W H 0.4819 0.5057 0.2162 0.253 Uiso 1 1 d R . . Zn1 Zn 0.217069(12) 0.34324(3) 0.100742(17) 0.02444(10) Uani 1 1 d . . . O1W O 0.97507(13) 0.9078(4) 0.9255(2) 0.1216(13) Uani 1 1 d . . . H1W H 0.9396 0.9034 0.9317 0.182 Uiso 1 1 d R . . H2W H 0.9862 0.9984 0.9344 0.182 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 C1 0.0288(13) 0.0271(12) 0.0203(11) 0.0018(9) 0.0085(10) -0.0009(10) C2 0.0291(13) 0.0321(13) 0.0260(13) 0.0004(10) 0.0035(10) 0.0067(10) C3 0.0264(12) 0.0267(12) 0.0285(13) -0.0016(9) 0.0090(10) 0.0054(9) C4 0.0466(17) 0.0499(17) 0.0536(18) 0.0042(14) 0.0310(15) 0.0081(14) C5 0.052(2) 0.069(2) 0.082(2) -0.0012(19) 0.0485(19) 0.0058(17) C6 0.0314(16) 0.067(2) 0.079(2) -0.0185(19) 0.0237(16) 0.0079(15) C7 0.0314(15) 0.0459(16) 0.0529(18) -0.0098(14) 0.0040(13) 0.0130(12) C8 0.0275(13) 0.0340(14) 0.0293(13) -0.0091(11) 0.0015(10) 0.0045(10) C9 0.0399(15) 0.0293(13) 0.0302(14) -0.0024(11) 0.0049(11) 0.0063(11) C10 0.064(2) 0.0476(18) 0.0458(18) 0.0123(15) 0.0116(16) 0.0220(16) C11 0.096(3) 0.0412(18) 0.0435(18) 0.0153(14) 0.0193(18) 0.0162(18) C12 0.091(3) 0.0413(17) 0.0377(17) 0.0072(13) 0.0313(17) 0.0000(16) C13 0.0582(18) 0.0342(14) 0.0349(15) -0.0001(11) 0.0240(13) 0.0022(13) N1 0.0313(11) 0.0255(10) 0.0250(10) -0.0017(8) 0.0113(9) 0.0026(8) N2 0.0327(12) 0.0273(10) 0.0246(10) -0.0018(8) 0.0119(9) 0.0022(9) N3 0.0335(11) 0.0277(11) 0.0268(11) -0.0035(8) 0.0147(9) -0.0007(9) N4 0.0333(11) 0.0339(11) 0.0269(11) -0.0032(9) 0.0109(9) 0.0013(9) N5 0.0262(10) 0.0273(10) 0.0223(10) 0.0001(8) 0.0099(8) 0.0024(8) N6 0.0270(11) 0.0356(11) 0.0279(11) -0.0045(9) 0.0129(9) -0.0001(9) N7 0.0287(12) 0.0644(15) 0.0355(13) -0.0111(11) 0.0146(10) -0.0011(11) N8 0.0269(12) 0.0643(16) 0.0350(13) -0.0107(11) 0.0090(10) 0.0027(10) N9 0.0267(11) 0.0345(11) 0.0288(11) -0.0025(9) 0.0110(9) 0.0030(9) N10 0.0391(12) 0.0279(11) 0.0249(10) 0.0006(8) 0.0116(9) 0.0022(9) O2W 0.091(4) 0.159(5) 0.249(8) 0.000 0.041(4) 0.000 Zn1 0.02559(17) 0.02702(16) 0.02288(16) 0.00163(11) 0.01072(11) 0.00338(11) O1W 0.0539(18) 0.099(2) 0.185(4) -0.030(2) -0.002(2) 0.0031(16) _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 C1 N4 1.324(3) . ? C1 N1 1.334(3) . ? C1 C2 1.490(3) . ? C2 C3 1.495(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N5 1.326(3) . ? C3 N8 1.331(3) . ? C4 N9 1.325(3) . ? C4 C5 1.373(4) . ? C4 H4 0.9300 . ? C5 C6 1.359(5) . ? C5 H5 0.9300 . ? C6 C7 1.368(5) . ? C6 H6 0.9300 . ? C7 C8 1.389(4) . ? C7 H7 0.9300 . ? C8 N9 1.337(3) . ? C8 C9 1.482(4) . ? C9 N10 1.341(3) . ? C9 C10 1.385(4) . ? C10 C11 1.367(5) . ? C10 H10 0.9300 . ? C11 C12 1.372(5) . ? C11 H11 0.9300 . ? C12 C13 1.375(4) . ? C12 H12 0.9300 . ? C13 N10 1.341(3) . ? C13 H13 0.9300 . ? N1 N2 1.347(3) . ? N1 Zn1 2.1970(19) . ? N2 N3 1.311(3) . ? N3 N4 1.346(3) . ? N3 Zn1 2.1818(19) 4 ? N5 N6 1.362(3) . ? N5 Zn1 2.1368(19) . ? N6 N7 1.302(3) . ? N6 Zn1 2.232(2) 7 ? N7 N8 1.343(3) . ? N9 Zn1 2.165(2) . ? N10 Zn1 2.196(2) . ? O2W H4W 0.8501 . ? Zn1 N3 2.1818(19) 4_545 ? Zn1 N6 2.232(2) 7 ? O1W H1W 0.8488 . ? O1W H2W 0.8449 . ? 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 N4 C1 N1 111.5(2) . . ? N4 C1 C2 124.6(2) . . ? N1 C1 C2 123.8(2) . . ? C1 C2 C3 113.43(19) . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2B 108.9 . . ? C3 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? N5 C3 N8 111.5(2) . . ? N5 C3 C2 125.4(2) . . ? N8 C3 C2 123.1(2) . . ? N9 C4 C5 123.3(3) . . ? N9 C4 H4 118.4 . . ? C5 C4 H4 118.4 . . ? C6 C5 C4 119.1(3) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C7 118.6(3) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C6 C7 C8 119.7(3) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? N9 C8 C7 121.3(3) . . ? N9 C8 C9 115.7(2) . . ? C7 C8 C9 123.0(2) . . ? N10 C9 C10 121.6(3) . . ? N10 C9 C8 115.9(2) . . ? C10 C9 C8 122.5(2) . . ? C11 C10 C9 119.0(3) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C10 C11 C12 120.0(3) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C13 118.3(3) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? N10 C13 C12 122.6(3) . . ? N10 C13 H13 118.7 . . ? C12 C13 H13 118.7 . . ? C1 N1 N2 105.68(18) . . ? C1 N1 Zn1 125.94(15) . . ? N2 N1 Zn1 128.37(15) . . ? N3 N2 N1 107.79(18) . . ? N2 N3 N4 110.68(18) . . ? N2 N3 Zn1 127.26(15) . 4 ? N4 N3 Zn1 121.85(15) . 4 ? C1 N4 N3 104.31(19) . . ? C3 N5 N6 104.59(18) . . ? C3 N5 Zn1 125.77(16) . . ? N6 N5 Zn1 128.55(14) . . ? N7 N6 N5 109.26(19) . . ? N7 N6 Zn1 115.14(15) . 7 ? N5 N6 Zn1 129.76(15) . 7 ? N6 N7 N8 109.3(2) . . ? C3 N8 N7 105.3(2) . . ? C4 N9 C8 118.0(2) . . ? C4 N9 Zn1 124.35(18) . . ? C8 N9 Zn1 117.40(16) . . ? C13 N10 C9 118.5(2) . . ? C13 N10 Zn1 125.17(17) . . ? C9 N10 Zn1 116.06(16) . . ? N5 Zn1 N9 167.21(7) . . ? N5 Zn1 N3 95.49(7) . 4_545 ? N9 Zn1 N3 94.19(8) . 4_545 ? N5 Zn1 N10 96.88(7) . . ? N9 Zn1 N10 74.81(7) . . ? N3 Zn1 N10 165.46(8) 4_545 . ? N5 Zn1 N1 84.57(7) . . ? N9 Zn1 N1 86.69(7) . . ? N3 Zn1 N1 92.48(7) 4_545 . ? N10 Zn1 N1 96.27(7) . . ? N5 Zn1 N6 93.07(7) . 7 ? N9 Zn1 N6 95.22(7) . 7 ? N3 Zn1 N6 90.24(7) 4_545 7 ? N10 Zn1 N6 81.49(8) . 7 ? N1 Zn1 N6 176.55(7) . 7 ? H1W O1W H2W 105.8 . . ? 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 N4 C1 C2 C3 -137.9(2) . . . . ? N1 C1 C2 C3 40.9(3) . . . . ? C1 C2 C3 N5 -49.5(3) . . . . ? C1 C2 C3 N8 132.0(2) . . . . ? N9 C4 C5 C6 1.3(5) . . . . ? C4 C5 C6 C7 -1.0(5) . . . . ? C5 C6 C7 C8 -0.4(5) . . . . ? C6 C7 C8 N9 1.7(4) . . . . ? C6 C7 C8 C9 -177.7(3) . . . . ? N9 C8 C9 N10 -4.7(3) . . . . ? C7 C8 C9 N10 174.8(2) . . . . ? N9 C8 C9 C10 174.8(3) . . . . ? C7 C8 C9 C10 -5.8(4) . . . . ? N10 C9 C10 C11 0.3(5) . . . . ? C8 C9 C10 C11 -179.1(3) . . . . ? C9 C10 C11 C12 1.0(5) . . . . ? C10 C11 C12 C13 -1.3(5) . . . . ? C11 C12 C13 N10 0.3(5) . . . . ? N4 C1 N1 N2 0.3(3) . . . . ? C2 C1 N1 N2 -178.6(2) . . . . ? N4 C1 N1 Zn1 179.01(14) . . . . ? C2 C1 N1 Zn1 0.1(3) . . . . ? C1 N1 N2 N3 0.0(2) . . . . ? Zn1 N1 N2 N3 -178.67(14) . . . . ? N1 N2 N3 N4 -0.3(2) . . . . ? N1 N2 N3 Zn1 174.43(14) . . . 4 ? N1 C1 N4 N3 -0.5(3) . . . . ? C2 C1 N4 N3 178.4(2) . . . . ? N2 N3 N4 C1 0.5(2) . . . . ? Zn1 N3 N4 C1 -174.58(15) 4 . . . ? N8 C3 N5 N6 0.8(3) . . . . ? C2 C3 N5 N6 -177.8(2) . . . . ? N8 C3 N5 Zn1 -168.00(16) . . . . ? C2 C3 N5 Zn1 13.4(3) . . . . ? C3 N5 N6 N7 -0.8(3) . . . . ? Zn1 N5 N6 N7 167.59(17) . . . . ? C3 N5 N6 Zn1 150.37(17) . . . 7 ? Zn1 N5 N6 Zn1 -41.2(3) . . . 7 ? N5 N6 N7 N8 0.5(3) . . . . ? Zn1 N6 N7 N8 -155.31(17) 7 . . . ? N5 C3 N8 N7 -0.5(3) . . . . ? C2 C3 N8 N7 178.1(2) . . . . ? N6 N7 N8 C3 0.0(3) . . . . ? C5 C4 N9 C8 0.0(4) . . . . ? C5 C4 N9 Zn1 173.9(3) . . . . ? C7 C8 N9 C4 -1.5(4) . . . . ? C9 C8 N9 C4 178.0(2) . . . . ? C7 C8 N9 Zn1 -175.83(19) . . . . ? C9 C8 N9 Zn1 3.6(3) . . . . ? C12 C13 N10 C9 0.9(4) . . . . ? C12 C13 N10 Zn1 175.2(2) . . . . ? C10 C9 N10 C13 -1.2(4) . . . . ? C8 C9 N10 C13 178.2(2) . . . . ? C10 C9 N10 Zn1 -176.0(2) . . . . ? C8 C9 N10 Zn1 3.4(3) . . . . ? C3 N5 Zn1 N9 66.2(4) . . . . ? N6 N5 Zn1 N9 -99.9(4) . . . . ? C3 N5 Zn1 N3 -72.84(19) . . . 4_545 ? N6 N5 Zn1 N3 121.02(19) . . . 4_545 ? C3 N5 Zn1 N10 114.82(19) . . . . ? N6 N5 Zn1 N10 -51.31(19) . . . . ? C3 N5 Zn1 N1 19.14(19) . . . . ? N6 N5 Zn1 N1 -146.99(19) . . . . ? C3 N5 Zn1 N6 -163.38(19) . . . 7 ? N6 N5 Zn1 N6 30.5(2) . . . 7 ? C4 N9 Zn1 N5 -124.8(3) . . . . ? C8 N9 Zn1 N5 49.1(4) . . . . ? C4 N9 Zn1 N3 14.3(2) . . . 4_545 ? C8 N9 Zn1 N3 -171.75(17) . . . 4_545 ? C4 N9 Zn1 N10 -175.4(2) . . . . ? C8 N9 Zn1 N10 -1.41(16) . . . . ? C4 N9 Zn1 N1 -78.0(2) . . . . ? C8 N9 Zn1 N1 96.00(17) . . . . ? C4 N9 Zn1 N6 104.9(2) . . . 7 ? C8 N9 Zn1 N6 -81.12(18) . . . 7 ? C13 N10 Zn1 N5 14.3(2) . . . . ? C9 N10 Zn1 N5 -171.31(17) . . . . ? C13 N10 Zn1 N9 -175.6(2) . . . . ? C9 N10 Zn1 N9 -1.23(17) . . . . ? C13 N10 Zn1 N3 -133.8(3) . . . 4_545 ? C9 N10 Zn1 N3 40.6(4) . . . 4_545 ? C13 N10 Zn1 N1 99.6(2) . . . . ? C9 N10 Zn1 N1 -86.06(18) . . . . ? C13 N10 Zn1 N6 -77.8(2) . . . 7 ? C9 N10 Zn1 N6 96.59(18) . . . 7 ? C1 N1 Zn1 N5 -25.78(18) . . . . ? N2 N1 Zn1 N5 152.61(19) . . . . ? C1 N1 Zn1 N9 163.56(19) . . . . ? N2 N1 Zn1 N9 -18.05(18) . . . . ? C1 N1 Zn1 N3 69.50(19) . . . 4_545 ? N2 N1 Zn1 N3 -112.11(18) . . . 4_545 ? C1 N1 Zn1 N10 -122.13(19) . . . . ? N2 N1 Zn1 N10 56.26(19) . . . . ? C1 N1 Zn1 N6 -72.7(12) . . . 7 ? N2 N1 Zn1 N6 105.7(12) . . . 7 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.377 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.065 data_3 _database_code_depnum_ccdc_archive 'CCDC 819506' #TrackingRef '- xx.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H6 Cd N9' _chemical_formula_sum 'C8 H6 Cd N9' _chemical_formula_weight 340.63 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 13.780(2) _cell_length_b 7.6575(13) _cell_length_c 10.3601(18) _cell_angle_alpha 90.00 _cell_angle_beta 101.124(2) _cell_angle_gamma 90.00 _cell_volume 1072.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description piece _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.109 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 2.033 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.700 _exptl_absorpt_correction_T_max 0.737 _exptl_absorpt_process_details 'Apex2 (Bruker, 2005)' _exptl_special_details ; In the original refinement the molecule showed significantly elongated thermal ellipsoids indicating disorder. The ethanol molecule was thus refined as being disordered over two sites in a ratio of 0.5: 0.5. Due to the significant overlap of the disordered atoms the following restraints and constraints were applied: The adps of the disordered atoms were restrained to be close to isotropic and those of equivalent atoms were set to be identical. ; _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 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 6141 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.40 _reflns_number_total 1978 _reflns_number_gt 1848 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker, 2005)' _computing_cell_refinement 'Apex2 (Bruker, 2005)' _computing_data_reduction 'Apex2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL 6.12 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.12' _computing_molecular_graphics 'SHELXTL 6.12' _computing_publication_material 'SHELXTL 6.12' _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^)+(0.0249P)^2^+1.8608P] 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 1961 _refine_ls_number_parameters 200 _refine_ls_number_restraints 75 _refine_ls_R_factor_all 0.0289 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0682 _refine_ls_wR_factor_gt 0.0672 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.164 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5090(3) -0.1647(5) 0.7809(3) 0.0262(8) Uani 1 1 d . . . C2 C 0.4366(3) -0.1480(6) 0.8709(4) 0.0306(8) Uani 1 1 d . . . H2A H 0.4610 -0.2142 0.9503 0.037 Uiso 1 1 calc R . . H2B H 0.4332 -0.0264 0.8958 0.037 Uiso 1 1 calc R . . C3 C 0.3348(3) -0.2093(5) 0.8134(3) 0.0259(8) Uani 1 1 d . . . C6 C 0.0399(3) 0.4345(5) 0.5007(4) 0.0354(9) Uani 1 1 d D . . C7 C 0.1285(7) 0.4783(12) 0.4639(10) 0.028(2) Uani 0.50 1 d PDU . . H7 H 0.1363 0.5897 0.4314 0.033 Uiso 0.50 1 calc PR . . C8 C 0.2063(7) 0.3589(11) 0.4745(10) 0.034(2) Uani 0.50 1 d PDU . . H8 H 0.2674 0.3947 0.4587 0.041 Uiso 0.50 1 calc PR . . Cd1 Cd 0.332541(19) 0.01927(3) 0.54240(2) 0.02234(11) Uani 1 1 d . . . N1 N 0.4957(2) -0.0990(4) 0.6595(3) 0.0287(7) Uani 1 1 d . . . N2 N 0.5802(2) -0.1363(4) 0.6184(3) 0.0287(7) Uani 1 1 d . . . N3 N 0.6405(3) -0.2202(5) 0.7105(3) 0.0338(8) Uani 1 1 d . . . N4 N 0.5971(2) -0.2404(4) 0.8144(3) 0.0308(7) Uani 1 1 d . . . N5 N 0.2821(2) -0.1533(4) 0.7000(3) 0.0312(7) Uani 1 1 d . . . N6 N 0.1932(3) -0.2362(5) 0.6869(3) 0.0369(8) Uani 1 1 d . . . N7 N 0.1946(3) -0.3364(5) 0.7888(3) 0.0381(8) Uani 1 1 d . . . N8 N 0.2839(2) -0.3221(4) 0.8713(3) 0.0297(7) Uani 1 1 d . . . N9 N 0.1926(3) 0.1931(4) 0.5073(3) 0.0325(7) Uani 1 1 d D . . C4 C 0.1082(6) 0.1457(13) 0.5324(12) 0.042(2) Uani 0.50 1 d PDU . . H4 H 0.0997 0.0297 0.5544 0.051 Uiso 0.50 1 calc PR . . C5 C 0.0300(7) 0.2597(11) 0.5279(13) 0.045(2) Uani 0.50 1 d PDU . . H5 H -0.0301 0.2182 0.5435 0.054 Uiso 0.50 1 calc PR . . C4' C 0.1327(8) 0.1880(15) 0.5972(11) 0.046(3) Uani 0.50 1 d PDU . . H4' H 0.1441 0.1011 0.6610 0.056 Uiso 0.50 1 calc PR . . C5' C 0.0562(8) 0.3031(14) 0.6002(11) 0.047(3) Uani 0.50 1 d PDU . . H5' H 0.0172 0.2955 0.6638 0.057 Uiso 0.50 1 calc PR . . C7' C 0.0982(11) 0.443(2) 0.4114(13) 0.061(4) Uani 0.50 1 d PDU . . H7' H 0.0873 0.5243 0.3435 0.073 Uiso 0.50 1 calc PR . . C8' C 0.1750(10) 0.3251(15) 0.4250(12) 0.056(4) Uani 0.50 1 d PDU . . H8' H 0.2198 0.3408 0.3693 0.067 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.026(2) 0.0264(19) 0.0247(18) 0.0023(15) 0.0017(15) -0.0026(15) C2 0.030(2) 0.036(2) 0.0247(18) 0.0034(16) 0.0024(16) 0.0015(17) C3 0.029(2) 0.0262(19) 0.0230(17) 0.0021(14) 0.0070(16) 0.0034(16) C6 0.028(2) 0.029(2) 0.048(2) 0.0043(19) 0.0045(18) 0.0067(19) C7 0.034(5) 0.022(4) 0.029(5) 0.008(3) 0.011(4) 0.006(3) C8 0.026(5) 0.036(5) 0.040(5) 0.001(4) 0.005(4) -0.001(4) Cd1 0.02327(18) 0.02275(17) 0.02125(16) -0.00018(10) 0.00490(12) 0.00210(10) N1 0.0321(18) 0.0303(18) 0.0241(15) 0.0032(13) 0.0067(13) 0.0029(14) N2 0.0287(18) 0.0297(17) 0.0275(16) 0.0018(13) 0.0047(14) -0.0018(14) N3 0.0291(19) 0.0377(19) 0.0369(18) 0.0099(15) 0.0117(15) 0.0035(15) N4 0.0243(18) 0.0361(19) 0.0321(17) 0.0104(14) 0.0058(14) 0.0003(14) N5 0.0291(18) 0.0364(19) 0.0268(16) 0.0043(14) 0.0021(14) -0.0011(15) N6 0.032(2) 0.041(2) 0.0360(19) 0.0073(16) 0.0020(15) -0.0041(16) N7 0.033(2) 0.041(2) 0.0398(19) 0.0084(16) 0.0059(16) -0.0036(16) N8 0.0293(18) 0.0303(18) 0.0302(16) 0.0057(14) 0.0078(14) 0.0003(14) N9 0.0318(19) 0.0269(18) 0.0380(18) 0.0008(14) 0.0048(15) 0.0046(15) C4 0.029(5) 0.029(4) 0.068(6) 0.004(5) 0.007(5) -0.001(4) C5 0.025(5) 0.040(5) 0.069(6) 0.009(5) 0.006(5) 0.001(4) C4' 0.053(6) 0.047(6) 0.040(5) 0.013(4) 0.013(5) 0.021(5) C5' 0.050(6) 0.049(5) 0.048(5) 0.015(5) 0.021(5) 0.023(5) C7' 0.059(7) 0.072(7) 0.057(7) 0.030(6) 0.024(6) 0.029(6) C8' 0.046(7) 0.070(7) 0.060(7) 0.024(6) 0.030(5) 0.028(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N4 1.329(5) . ? C1 N1 1.334(5) . ? C1 C2 1.497(5) . ? C2 C3 1.490(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N8 1.327(5) . ? C3 N5 1.328(5) . ? C6 C7' 1.339(11) . ? C6 C5 1.380(9) . ? C6 C7 1.389(9) . ? C6 C5' 1.427(11) . ? C6 C6 1.486(8) 3_566 ? C7 C8 1.396(11) . ? C7 H7 0.9300 . ? C8 N9 1.337(9) . ? C8 H8 0.9300 . ? Cd1 N5 2.309(3) . ? Cd1 N9 2.313(3) . ? Cd1 N8 2.326(3) 4 ? Cd1 N2 2.408(3) 3_656 ? Cd1 N4 2.444(3) 2_656 ? Cd1 N1 2.509(3) . ? N1 N2 1.345(4) . ? N2 N3 1.307(5) . ? N2 Cd1 2.408(3) 3_656 ? N3 N4 1.338(4) . ? N4 Cd1 2.444(3) 2_646 ? N5 N6 1.364(5) . ? N6 N7 1.302(5) . ? N7 N8 1.361(5) . ? N8 Cd1 2.326(3) 4_556 ? N9 C4 1.293(9) . ? N9 C8' 1.315(10) . ? N9 C4' 1.359(9) . ? C4 C5 1.380(10) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C4' C5' 1.379(10) . ? C4' H4' 0.9300 . ? C5' H5' 0.9300 . ? C7' C8' 1.378(17) . ? C7' H7' 0.9300 . ? C8' H8' 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 N4 C1 N1 111.3(3) . . ? N4 C1 C2 124.0(3) . . ? N1 C1 C2 124.6(3) . . ? C3 C2 C1 114.4(3) . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? N8 C3 N5 111.3(3) . . ? N8 C3 C2 124.3(3) . . ? N5 C3 C2 124.3(3) . . ? C7' C6 C5 106.5(9) . . ? C7' C6 C7 28.6(6) . . ? C5 C6 C7 114.7(6) . . ? C7' C6 C5' 120.1(7) . . ? C5 C6 C5' 34.6(5) . . ? C7 C6 C5' 110.1(6) . . ? C7' C6 C6 120.1(7) . 3_566 ? C5 C6 C6 123.7(6) . 3_566 ? C7 C6 C6 121.5(6) . 3_566 ? C5' C6 C6 119.7(6) . 3_566 ? C6 C7 C8 121.5(8) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? N9 C8 C7 119.9(8) . . ? N9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? N5 Cd1 N9 94.88(12) . . ? N5 Cd1 N8 94.92(12) . 4 ? N9 Cd1 N8 98.34(12) . 4 ? N5 Cd1 N2 163.90(11) . 3_656 ? N9 Cd1 N2 100.92(11) . 3_656 ? N8 Cd1 N2 79.81(11) 4 3_656 ? N5 Cd1 N4 98.05(12) . 2_656 ? N9 Cd1 N4 83.29(12) . 2_656 ? N8 Cd1 N4 166.75(11) 4 2_656 ? N2 Cd1 N4 86.96(11) 3_656 2_656 ? N5 Cd1 N1 79.35(11) . . ? N9 Cd1 N1 157.78(11) . . ? N8 Cd1 N1 103.50(11) 4 . ? N2 Cd1 N1 87.04(10) 3_656 . ? N4 Cd1 N1 76.40(11) 2_656 . ? C1 N1 N2 104.3(3) . . ? C1 N1 Cd1 122.7(2) . . ? N2 N1 Cd1 132.3(2) . . ? N3 N2 N1 110.0(3) . . ? N3 N2 Cd1 110.8(2) . 3_656 ? N1 N2 Cd1 135.9(2) . 3_656 ? N2 N3 N4 108.9(3) . . ? C1 N4 N3 105.5(3) . . ? C1 N4 Cd1 136.3(2) . 2_646 ? N3 N4 Cd1 112.8(2) . 2_646 ? C3 N5 N6 105.4(3) . . ? C3 N5 Cd1 128.5(3) . . ? N6 N5 Cd1 125.7(2) . . ? N7 N6 N5 108.7(3) . . ? N6 N7 N8 109.4(3) . . ? C3 N8 N7 105.1(3) . . ? C3 N8 Cd1 131.9(3) . 4_556 ? N7 N8 Cd1 121.3(2) . 4_556 ? C4 N9 C8' 106.6(8) . . ? C4 N9 C8 119.6(7) . . ? C8' N9 C8 28.6(6) . . ? C4 N9 C4' 33.3(5) . . ? C8' N9 C4' 114.0(7) . . ? C8 N9 C4' 109.6(7) . . ? C4 N9 Cd1 124.2(5) . . ? C8' N9 Cd1 126.0(5) . . ? C8 N9 Cd1 115.6(5) . . ? C4' N9 Cd1 118.3(5) . . ? N9 C4 C5 122.9(8) . . ? N9 C4 H4 118.6 . . ? C5 C4 H4 118.6 . . ? C6 C5 C4 120.8(8) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? N9 C4' C5' 124.4(8) . . ? N9 C4' H4' 117.8 . . ? C5' C4' H4' 117.8 . . ? C4' C5' C6 116.7(8) . . ? C4' C5' H5' 121.6 . . ? C6 C5' H5' 121.6 . . ? C6 C7' C8' 116.7(10) . . ? C6 C7' H7' 121.6 . . ? C8' C7' H7' 121.6 . . ? N9 C8' C7' 127.7(10) . . ? N9 C8' H8' 116.2 . . ? C7' C8' H8' 116.2 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.625 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.095 data_4 _database_code_depnum_ccdc_archive 'CCDC 819507' #TrackingRef '- xx.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C8 H7 N5 O2 Zn), 4(H O0.50)' _chemical_formula_sum 'C16 H20 N10 O7 Zn2 ' _chemical_formula_weight 595.20 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.896(3) _cell_length_b 16.987(3) _cell_length_c 9.7748(19) _cell_angle_alpha 90.00 _cell_angle_beta 119.087(2) _cell_angle_gamma 90.00 _cell_volume 2451.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2210 _cell_measurement_theta_min 1.83 _cell_measurement_theta_max 25.20 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 2.013 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.575 _exptl_absorpt_correction_T_max 0.617 _exptl_absorpt_process_details 'Apex2 (Bruker, 2005)' _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 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 6194 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.20 _reflns_number_total 2210 _reflns_number_gt 1865 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker, 2005)' _computing_cell_refinement 'Apex2 (Bruker, 2005)' _computing_data_reduction 'Apex2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL 6.12 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.12' _computing_molecular_graphics 'SHELXTL 6.12' _computing_publication_material 'SHELXTL 6.12' _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^)+(0.0654P)^2^+3.5672P] 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 2209 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1151 _refine_ls_wR_factor_gt 0.1105 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.043 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.23336(3) 0.39258(2) 1.15347(4) 0.03146(18) Uani 1 1 d . . . O2 O 0.14095(17) 0.31088(17) 1.0896(3) 0.0497(7) Uani 1 1 d . . . C3 C 0.0634(3) 0.3405(2) 0.9999(4) 0.0400(9) Uani 1 1 d . . . O1 O 0.0501(2) 0.41099(18) 0.9796(4) 0.0690(10) Uani 1 1 d . . . C2 C 0.2089(2) 0.5113(2) 0.8983(4) 0.0323(8) Uani 1 1 d . . . N4 N 0.2469(2) 0.44728(17) 0.9849(3) 0.0332(7) Uani 1 1 d . . . C4 C -0.0134(2) 0.2831(2) 0.9186(4) 0.0347(8) Uani 1 1 d . . . C5 C -0.0987(2) 0.3106(2) 0.8182(4) 0.0383(9) Uani 1 1 d . . . H5 H -0.1090 0.3644 0.8006 0.046 Uiso 1 1 calc R . . C8 C -0.0005(3) 0.2031(2) 0.9401(5) 0.0498(11) Uani 1 1 d . . . H8 H 0.0565 0.1826 1.0069 0.060 Uiso 1 1 calc R . . C6 C -0.1687(2) 0.2581(2) 0.7441(4) 0.0391(9) Uani 1 1 d . . . H6 H -0.2264 0.2774 0.6774 0.047 Uiso 1 1 calc R . . C7 C -0.0738(3) 0.1540(2) 0.8609(5) 0.0491(11) Uani 1 1 d . . . H7 H -0.0647 0.0999 0.8753 0.059 Uiso 1 1 calc R . . N5 N -0.15704(19) 0.18015(17) 0.7643(3) 0.0356(7) Uani 1 1 d . . . N3 N 0.3082(2) 0.4212(2) 0.9454(4) 0.0433(8) Uani 1 1 d . . . C1 C 0.1383(3) 0.5604(3) 0.9017(6) 0.0649(14) Uani 1 1 d . . . H1A H 0.0890 0.5667 0.7971 0.097 Uiso 1 1 calc R . . H1B H 0.1630 0.6111 0.9446 0.097 Uiso 1 1 calc R . . H1C H 0.1167 0.5355 0.9654 0.097 Uiso 1 1 calc R . . N1 N 0.2461(2) 0.52475(18) 0.8070(3) 0.0352(7) Uani 1 1 d . . . N2 N 0.3078(2) 0.4670(2) 0.8394(4) 0.0447(8) Uani 1 1 d . . . O1W O 0.4074(3) 0.4145(3) 0.6742(6) 0.1068(15) Uani 1 1 d . . . H1WB H 0.4178 0.3649 0.6948 0.160 Uiso 1 1 d R . . H1WA H 0.4038 0.4326 0.7525 0.160 Uiso 1 1 d R . . O2W O 0.1665(5) 0.7703(4) 0.8806(7) 0.0638(18) Uani 0.50 1 d P . . H2WB H 0.2195 0.7538 0.9394 0.096 Uiso 0.50 1 d PR . . H2WA H 0.1345 0.7302 0.8379 0.096 Uiso 0.50 1 d PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0249(3) 0.0321(3) 0.0317(3) 0.00038(16) 0.00937(19) -0.00002(16) O2 0.0251(14) 0.0497(17) 0.0562(17) -0.0006(14) 0.0054(13) -0.0064(12) C3 0.032(2) 0.045(2) 0.039(2) -0.0036(17) 0.0135(17) -0.0035(17) O1 0.0473(19) 0.0415(19) 0.090(3) -0.0037(17) 0.0112(18) -0.0091(15) C2 0.0313(18) 0.0325(19) 0.0334(18) -0.0004(15) 0.0158(15) 0.0005(15) N4 0.0305(15) 0.0360(16) 0.0333(16) 0.0005(13) 0.0155(13) 0.0023(13) C4 0.0292(19) 0.0356(19) 0.0364(19) -0.0021(15) 0.0136(16) -0.0024(15) C5 0.0322(19) 0.0288(18) 0.045(2) 0.0025(16) 0.0114(16) 0.0009(15) C8 0.0234(19) 0.045(2) 0.059(3) 0.003(2) 0.0033(18) 0.0034(17) C6 0.0242(18) 0.040(2) 0.040(2) 0.0017(16) 0.0058(16) 0.0011(16) C7 0.030(2) 0.032(2) 0.063(3) 0.0013(18) 0.0055(19) 0.0007(16) N5 0.0264(15) 0.0347(16) 0.0377(16) -0.0031(13) 0.0092(13) 0.0000(13) N3 0.0398(18) 0.0421(18) 0.051(2) 0.0104(16) 0.0243(16) 0.0141(15) C1 0.068(3) 0.057(3) 0.091(4) 0.028(3) 0.055(3) 0.031(2) N1 0.0305(16) 0.0359(17) 0.0354(16) 0.0031(13) 0.0130(13) 0.0035(13) N2 0.0446(19) 0.0475(19) 0.051(2) 0.0103(16) 0.0302(17) 0.0160(16) O1W 0.111(4) 0.122(4) 0.105(4) 0.009(3) 0.066(3) 0.022(3) O2W 0.078(5) 0.061(4) 0.042(3) -0.007(3) 0.022(3) 0.014(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 Zn1 O2 1.951(3) . ? Zn1 N1 1.989(3) 6_566 ? Zn1 N4 2.000(3) . ? Zn1 N5 2.044(3) 8_556 ? O2 C3 1.273(5) . ? C3 O1 1.216(5) . ? C3 C4 1.506(5) . ? C2 N4 1.336(5) . ? C2 N1 1.338(4) . ? C2 C1 1.468(5) . ? N4 N3 1.345(4) . ? C4 C5 1.372(5) . ? C4 C8 1.376(6) . ? C5 C6 1.373(5) . ? C5 H5 0.9300 . ? C8 C7 1.377(5) . ? C8 H8 0.9300 . ? C6 N5 1.340(5) . ? C6 H6 0.9300 . ? C7 N5 1.333(5) . ? C7 H7 0.9300 . ? N5 Zn1 2.044(3) 8_455 ? N3 N2 1.294(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? N1 N2 1.352(4) . ? N1 Zn1 1.989(3) 6_565 ? O1W H1WB 0.8639 . ? O1W H1WA 0.8551 . ? O2W H2WB 0.8426 . ? O2W H2WA 0.8431 . ? 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 Zn1 N1 121.33(12) . 6_566 ? O2 Zn1 N4 117.46(12) . . ? N1 Zn1 N4 106.26(12) 6_566 . ? O2 Zn1 N5 96.75(12) . 8_556 ? N1 Zn1 N5 106.79(12) 6_566 8_556 ? N4 Zn1 N5 106.31(12) . 8_556 ? C3 O2 Zn1 109.5(3) . . ? O1 C3 O2 123.2(4) . . ? O1 C3 C4 120.6(3) . . ? O2 C3 C4 116.2(3) . . ? N4 C2 N1 108.9(3) . . ? N4 C2 C1 126.4(3) . . ? N1 C2 C1 124.7(3) . . ? C2 N4 N3 106.7(3) . . ? C2 N4 Zn1 133.5(2) . . ? N3 N4 Zn1 119.7(2) . . ? C5 C4 C8 118.7(4) . . ? C5 C4 C3 119.5(3) . . ? C8 C4 C3 121.8(3) . . ? C4 C5 C6 119.4(3) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C4 C8 C7 118.7(4) . . ? C4 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? N5 C6 C5 122.5(3) . . ? N5 C6 H6 118.7 . . ? C5 C6 H6 118.7 . . ? N5 C7 C8 123.1(4) . . ? N5 C7 H7 118.4 . . ? C8 C7 H7 118.4 . . ? C7 N5 C6 117.6(3) . . ? C7 N5 Zn1 123.1(3) . 8_455 ? C6 N5 Zn1 119.3(2) . 8_455 ? N2 N3 N4 109.0(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 N1 N2 106.2(3) . . ? C2 N1 Zn1 135.2(2) . 6_565 ? N2 N1 Zn1 118.5(2) . 6_565 ? N3 N2 N1 109.1(3) . . ? H1WB O1W H1WA 103.7 . . ? H2WB O2W H2WA 106.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.686 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.092 data_5 _database_code_depnum_ccdc_archive 'CCDC 819508' #TrackingRef '- xx.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H20 Mn2 N20' _chemical_formula_sum 'C26 H20 Mn2 N20' _chemical_formula_weight 722.50 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 21/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 14.078(3) _cell_length_b 9.3366(17) _cell_length_c 22.029(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.811(3) _cell_angle_gamma 90.00 _cell_volume 2844.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.59 _cell_measurement_theta_max 25.15 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.687 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464.0 _exptl_absorpt_coefficient_mu 0.948 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.774 _exptl_absorpt_correction_T_max 0.804 _exptl_absorpt_process_details 'Apex2 (Bruker, 2005)' _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 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 16763 _diffrn_reflns_av_R_equivalents 0.0610 _diffrn_reflns_av_sigmaI/netI 0.0894 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 28.03 _reflns_number_total 6897 _reflns_number_gt 3855 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker, 2005)' _computing_cell_refinement 'Apex2 (Bruker, 2005)' _computing_data_reduction 'Apex2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL 6.12 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.12' _computing_molecular_graphics 'SHELXTL 6.12' _computing_publication_material 'SHELXTL 6.12' _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^)+(0.0487P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6645 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1031 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1214 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _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 C1 C 1.0808(3) 0.5516(4) 0.11636(19) 0.0489(10) Uani 1 1 d . . . H1 H 1.0202 0.5306 0.0932 0.059 Uiso 1 1 calc R . . C2 C 1.1352(4) 0.4413(5) 0.1455(2) 0.0609(12) Uani 1 1 d . . . H2 H 1.1117 0.3480 0.1428 0.073 Uiso 1 1 calc R . . C3 C 1.2239(4) 0.4719(5) 0.1784(2) 0.0611(13) Uani 1 1 d . . . H3 H 1.2620 0.3993 0.1991 0.073 Uiso 1 1 calc R . . C4 C 1.2579(3) 0.6103(5) 0.18110(19) 0.0522(11) Uani 1 1 d . . . H4 H 1.3193 0.6318 0.2031 0.063 Uiso 1 1 calc R . . C5 C 1.1999(3) 0.7162(4) 0.15088(15) 0.0359(9) Uani 1 1 d . . . C6 C 1.2322(3) 0.8673(4) 0.14807(16) 0.0373(9) Uani 1 1 d . . . C7 C 1.3184(3) 0.9193(5) 0.18174(18) 0.0488(11) Uani 1 1 d . . . H7 H 1.3570 0.8611 0.2106 0.059 Uiso 1 1 calc R . . C8 C 1.3463(3) 1.0557(5) 0.1723(2) 0.0592(13) Uani 1 1 d . . . H8 H 1.4040 1.0915 0.1948 0.071 Uiso 1 1 calc R . . C9 C 1.2891(3) 1.1398(5) 0.1296(2) 0.0570(12) Uani 1 1 d . . . H9 H 1.3076 1.2328 0.1221 0.068 Uiso 1 1 calc R . . C10 C 1.2028(3) 1.0836(4) 0.09772(19) 0.0468(10) Uani 1 1 d . . . H10 H 1.1637 1.1406 0.0686 0.056 Uiso 1 1 calc R . . C11 C 1.0893(3) 0.8351(4) -0.09794(15) 0.0342(9) Uani 1 1 d . . . C12 C 1.1222(3) 0.8895(4) -0.15380(16) 0.0422(10) Uani 1 1 d . . . H12A H 1.1441 0.8088 -0.1753 0.051 Uiso 1 1 calc R . . H12B H 1.1773 0.9519 -0.1407 0.051 Uiso 1 1 calc R . . C13 C 1.0483(3) 0.9693(4) -0.19817(15) 0.0324(8) Uani 1 1 d . . . C14 C 0.8410(3) 0.6892(4) 0.13628(15) 0.0310(8) Uani 1 1 d . . . C15 C 0.8993(3) 0.6458(4) 0.19788(16) 0.0411(9) Uani 1 1 d . . . H15A H 0.9639 0.6208 0.1923 0.049 Uiso 1 1 calc R . . H15B H 0.9049 0.7280 0.2253 0.049 Uiso 1 1 calc R . . C16 C 0.8591(3) 0.5228(4) 0.22887(15) 0.0323(8) Uani 1 1 d . . . C17 C 0.6409(3) 0.2740(4) 0.13725(16) 0.0433(10) Uani 1 1 d . . . H17 H 0.6995 0.2743 0.1650 0.052 Uiso 1 1 calc R . . C18 C 0.6066(3) 0.1457(4) 0.11042(18) 0.0480(10) Uani 1 1 d . . . H18 H 0.6405 0.0609 0.1205 0.058 Uiso 1 1 calc R . . C19 C 0.5217(3) 0.1468(4) 0.06882(18) 0.0480(10) Uani 1 1 d . . . H19 H 0.4976 0.0620 0.0498 0.058 Uiso 1 1 calc R . . C20 C 0.4724(3) 0.2705(4) 0.05510(16) 0.0411(9) Uani 1 1 d . . . H20 H 0.4145 0.2712 0.0266 0.049 Uiso 1 1 calc R . . C21 C 0.5086(2) 0.3957(4) 0.08376(14) 0.0295(8) Uani 1 1 d . . . C22 C 0.4589(2) 0.5346(4) 0.07238(14) 0.0307(8) Uani 1 1 d . . . C23 C 0.3704(3) 0.5482(4) 0.03231(16) 0.0429(10) Uani 1 1 d . . . H23 H 0.3402 0.4685 0.0119 0.051 Uiso 1 1 calc R . . C24 C 0.3282(3) 0.6818(5) 0.02337(17) 0.0470(10) Uani 1 1 d . . . H24 H 0.2693 0.6933 -0.0035 0.056 Uiso 1 1 calc R . . C25 C 0.3736(3) 0.7966(4) 0.05425(16) 0.0437(10) Uani 1 1 d . . . H25 H 0.3466 0.8877 0.0486 0.052 Uiso 1 1 calc R . . C26 C 0.4595(3) 0.7750(4) 0.09361(15) 0.0374(9) Uani 1 1 d . . . H26 H 0.4899 0.8537 0.1148 0.045 Uiso 1 1 calc R . . Mn1 Mn 0.63584(4) 0.60887(5) 0.17627(2) 0.02741(14) Uani 1 1 d . . . Mn2 Mn 1.01582(4) 0.86942(5) 0.08280(2) 0.02973(15) Uani 1 1 d . . . N1 N 1.1104(2) 0.6876(3) 0.11938(13) 0.0374(7) Uani 1 1 d . . . N2 N 1.1739(2) 0.9506(3) 0.10728(13) 0.0353(7) Uani 1 1 d . . . N3 N 1.0485(2) 0.9164(3) -0.05951(13) 0.0343(7) Uani 1 1 d . . . N4 N 1.0335(2) 0.8253(3) -0.01470(13) 0.0348(7) Uani 1 1 d . . . N5 N 1.0648(2) 0.6982(3) -0.02634(14) 0.0476(9) Uani 1 1 d . . . N6 N 1.1004(2) 0.7011(3) -0.07823(14) 0.0454(8) Uani 1 1 d . . . N7 N 0.9840(2) 1.0540(3) -0.18074(12) 0.0313(7) Uani 1 1 d . . . N8 N 0.9323(2) 1.1091(3) -0.23366(14) 0.0422(8) Uani 1 1 d . . . N9 N 0.9667(2) 1.0573(3) -0.28042(14) 0.0424(8) Uani 1 1 d . . . N10 N 1.0417(2) 0.9659(3) -0.25872(12) 0.0322(7) Uani 1 1 d . . . N11 N 0.8778(2) 0.7547(3) 0.09196(12) 0.0355(7) Uani 1 1 d . . . N12 N 0.8005(2) 0.7837(4) 0.04658(13) 0.0470(9) Uani 1 1 d . . . N13 N 0.7221(2) 0.7368(4) 0.06379(13) 0.0472(9) Uani 1 1 d . . . N14 N 0.7461(2) 0.6757(3) 0.12073(12) 0.0321(7) Uani 1 1 d . . . N15 N 0.7672(2) 0.5115(3) 0.23540(12) 0.0315(7) Uani 1 1 d . . . N16 N 0.7642(2) 0.3918(3) 0.26970(13) 0.0362(7) Uani 1 1 d . . . N17 N 0.8506(2) 0.3372(3) 0.28305(13) 0.0347(7) Uani 1 1 d . . . N18 N 0.9138(2) 0.4187(3) 0.25782(13) 0.0379(7) Uani 1 1 d . . . N19 N 0.5936(2) 0.3970(3) 0.12490(12) 0.0330(7) Uani 1 1 d . . . N20 N 0.5026(2) 0.6477(3) 0.10347(12) 0.0303(7) 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 C1 0.050(3) 0.043(2) 0.053(3) -0.003(2) 0.010(2) 0.005(2) C2 0.070(3) 0.043(3) 0.071(3) 0.007(2) 0.016(3) 0.011(2) C3 0.073(3) 0.052(3) 0.058(3) 0.014(2) 0.012(3) 0.024(3) C4 0.048(3) 0.058(3) 0.049(2) 0.002(2) 0.005(2) 0.014(2) C5 0.038(2) 0.047(2) 0.0246(18) -0.0004(17) 0.0108(16) 0.0083(18) C6 0.0295(19) 0.054(2) 0.0295(19) -0.0048(18) 0.0096(16) 0.0060(19) C7 0.039(2) 0.069(3) 0.036(2) -0.005(2) 0.0014(18) 0.007(2) C8 0.036(2) 0.079(3) 0.063(3) -0.028(3) 0.007(2) -0.009(2) C9 0.047(3) 0.051(3) 0.077(3) -0.016(2) 0.022(2) -0.012(2) C10 0.042(2) 0.048(3) 0.055(3) 0.005(2) 0.021(2) -0.001(2) C11 0.036(2) 0.041(2) 0.0247(17) 0.0017(16) 0.0049(16) 0.0079(17) C12 0.049(2) 0.052(2) 0.0293(19) 0.0050(18) 0.0174(18) 0.015(2) C13 0.034(2) 0.036(2) 0.0288(19) 0.0015(16) 0.0095(16) -0.0010(17) C14 0.032(2) 0.034(2) 0.0259(18) 0.0014(15) 0.0016(15) -0.0046(16) C15 0.033(2) 0.051(2) 0.037(2) 0.0107(18) 0.0008(17) -0.0074(19) C16 0.034(2) 0.035(2) 0.0276(18) 0.0031(16) 0.0051(16) -0.0014(17) C17 0.044(2) 0.045(2) 0.037(2) -0.0069(19) -0.0034(18) 0.005(2) C18 0.058(3) 0.039(2) 0.045(2) 0.0008(19) 0.006(2) 0.007(2) C19 0.057(3) 0.044(3) 0.042(2) -0.005(2) 0.008(2) -0.009(2) C20 0.042(2) 0.046(2) 0.034(2) -0.0036(18) 0.0040(18) -0.010(2) C21 0.0284(18) 0.039(2) 0.0224(16) -0.0034(16) 0.0073(14) -0.0066(17) C22 0.0288(19) 0.042(2) 0.0215(17) -0.0012(16) 0.0050(15) -0.0021(17) C23 0.038(2) 0.053(3) 0.035(2) -0.0035(19) 0.0002(18) -0.005(2) C24 0.036(2) 0.071(3) 0.032(2) 0.009(2) 0.0009(17) 0.009(2) C25 0.040(2) 0.053(3) 0.038(2) 0.0001(19) 0.0056(18) 0.013(2) C26 0.041(2) 0.040(2) 0.0301(19) -0.0002(17) 0.0043(17) 0.0024(18) Mn1 0.0262(3) 0.0338(3) 0.0215(3) 0.0009(2) 0.0025(2) -0.0019(2) Mn2 0.0297(3) 0.0361(3) 0.0246(3) 0.0005(2) 0.0083(2) 0.0011(2) N1 0.0369(18) 0.0388(18) 0.0376(17) 0.0015(14) 0.0101(14) 0.0041(15) N2 0.0273(16) 0.0451(19) 0.0345(16) -0.0003(15) 0.0084(13) 0.0020(14) N3 0.0395(18) 0.0387(18) 0.0256(15) 0.0054(13) 0.0088(13) 0.0048(14) N4 0.0415(18) 0.0372(18) 0.0272(15) 0.0032(14) 0.0100(14) 0.0012(15) N5 0.064(2) 0.042(2) 0.0375(19) 0.0004(16) 0.0108(17) 0.0050(17) N6 0.063(2) 0.043(2) 0.0330(17) 0.0014(15) 0.0151(16) 0.0146(17) N7 0.0313(16) 0.0424(18) 0.0204(14) -0.0005(13) 0.0056(12) 0.0044(14) N8 0.0360(18) 0.058(2) 0.0343(17) -0.0025(16) 0.0103(14) 0.0054(16) N9 0.0385(19) 0.055(2) 0.0344(17) -0.0038(16) 0.0071(15) -0.0009(16) N10 0.0324(17) 0.0423(17) 0.0227(15) 0.0021(14) 0.0074(13) 0.0068(14) N11 0.0364(18) 0.0447(18) 0.0257(15) 0.0040(14) 0.0066(13) -0.0079(15) N12 0.042(2) 0.067(2) 0.0303(17) 0.0144(16) 0.0022(15) -0.0142(17) N13 0.0387(19) 0.069(2) 0.0315(17) 0.0083(17) 0.0015(15) -0.0121(18) N14 0.0318(17) 0.0397(17) 0.0236(15) 0.0029(13) 0.0017(13) -0.0054(14) N15 0.0309(16) 0.0343(17) 0.0283(15) 0.0055(13) 0.0029(13) -0.0018(13) N16 0.0383(18) 0.0365(18) 0.0335(16) 0.0063(14) 0.0057(14) 0.0006(15) N17 0.0346(17) 0.0383(17) 0.0311(16) 0.0018(14) 0.0057(14) 0.0017(15) N18 0.0368(18) 0.0449(19) 0.0317(16) 0.0091(14) 0.0057(14) 0.0039(15) N19 0.0354(17) 0.0373(18) 0.0258(15) -0.0015(13) 0.0042(13) 0.0010(14) N20 0.0309(16) 0.0364(17) 0.0235(14) 0.0006(13) 0.0051(12) -0.0025(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 C1 N1 1.334(5) . ? C1 C2 1.369(5) . ? C1 H1 0.9300 . ? C2 C3 1.351(6) . ? C2 H2 0.9300 . ? C3 C4 1.376(6) . ? C3 H3 0.9300 . ? C4 C5 1.372(5) . ? C4 H4 0.9300 . ? C5 N1 1.346(4) . ? C5 C6 1.488(5) . ? C6 N2 1.345(4) . ? C6 C7 1.386(5) . ? C7 C8 1.360(6) . ? C7 H7 0.9300 . ? C8 C9 1.366(6) . ? C8 H8 0.9300 . ? C9 C10 1.388(5) . ? C9 H9 0.9300 . ? C10 N2 1.335(4) . ? C10 H10 0.9300 . ? C11 N6 1.324(4) . ? C11 N3 1.344(4) . ? C11 C12 1.483(5) . ? C12 C13 1.487(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N7 1.313(4) . ? C13 N10 1.320(4) . ? C14 N14 1.321(4) . ? C14 N11 1.336(4) . ? C14 C15 1.504(5) . ? C15 C16 1.500(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N18 1.326(4) . ? C16 N15 1.333(4) . ? C17 N19 1.330(4) . ? C17 C18 1.382(5) . ? C17 H17 0.9300 . ? C18 C19 1.363(5) . ? C18 H18 0.9300 . ? C19 C20 1.353(5) . ? C19 H19 0.9300 . ? C20 C21 1.380(5) . ? C20 H20 0.9300 . ? C21 N19 1.358(4) . ? C21 C22 1.473(5) . ? C22 N20 1.343(4) . ? C22 C23 1.391(5) . ? C23 C24 1.380(5) . ? C23 H23 0.9300 . ? C24 C25 1.363(5) . ? C24 H24 0.9300 . ? C25 C26 1.365(5) . ? C25 H25 0.9300 . ? C26 N20 1.334(4) . ? C26 H26 0.9300 . ? Mn1 N10 2.237(3) 4_576 ? Mn1 N14 2.238(3) . ? Mn1 N15 2.245(3) . ? Mn1 N20 2.257(3) . ? Mn1 N19 2.301(3) . ? Mn1 N17 2.306(3) 2_655 ? Mn2 N1 2.214(3) . ? Mn2 N3 2.215(3) 3_775 ? Mn2 N4 2.246(3) . ? Mn2 N11 2.261(3) . ? Mn2 N7 2.272(3) 3_775 ? Mn2 N2 2.317(3) . ? N3 N4 1.349(4) . ? N3 Mn2 2.215(3) 3_775 ? N4 N5 1.308(4) . ? N5 N6 1.332(4) . ? N7 N8 1.355(4) . ? N7 Mn2 2.272(3) 3_775 ? N8 N9 1.310(4) . ? N9 N10 1.372(4) . ? N10 Mn1 2.237(3) 4_675 ? N11 N12 1.360(4) . ? N12 N13 1.307(4) . ? N13 N14 1.362(4) . ? N15 N16 1.355(4) . ? N16 N17 1.301(4) . ? N17 N18 1.366(4) . ? N17 Mn1 2.306(3) 2_645 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 123.5(4) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 118.1(4) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C2 C3 C4 120.1(4) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 119.0(4) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N1 C5 C4 121.5(4) . . ? N1 C5 C6 115.5(3) . . ? C4 C5 C6 123.0(4) . . ? N2 C6 C7 121.2(4) . . ? N2 C6 C5 115.0(3) . . ? C7 C6 C5 123.6(4) . . ? C8 C7 C6 119.7(4) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 119.5(4) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C8 C9 C10 118.6(4) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? N2 C10 C9 122.4(4) . . ? N2 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? N6 C11 N3 111.4(3) . . ? N6 C11 C12 124.0(3) . . ? N3 C11 C12 124.5(3) . . ? C11 C12 C13 115.4(3) . . ? C11 C12 H12A 108.4 . . ? C13 C12 H12A 108.4 . . ? C11 C12 H12B 108.4 . . ? C13 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? N7 C13 N10 112.9(3) . . ? N7 C13 C12 123.0(3) . . ? N10 C13 C12 124.1(3) . . ? N14 C14 N11 111.5(3) . . ? N14 C14 C15 124.2(3) . . ? N11 C14 C15 124.2(3) . . ? C16 C15 C14 115.4(3) . . ? C16 C15 H15A 108.4 . . ? C14 C15 H15A 108.4 . . ? C16 C15 H15B 108.4 . . ? C14 C15 H15B 108.4 . . ? H15A C15 H15B 107.5 . . ? N18 C16 N15 112.2(3) . . ? N18 C16 C15 123.1(3) . . ? N15 C16 C15 124.5(3) . . ? N19 C17 C18 122.6(4) . . ? N19 C17 H17 118.7 . . ? C18 C17 H17 118.7 . . ? C19 C18 C17 118.3(4) . . ? C19 C18 H18 120.9 . . ? C17 C18 H18 120.9 . . ? C20 C19 C18 120.3(4) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C21 119.4(4) . . ? C19 C20 H20 120.3 . . ? C21 C20 H20 120.3 . . ? N19 C21 C20 121.1(3) . . ? N19 C21 C22 115.9(3) . . ? C20 C21 C22 123.0(3) . . ? N20 C22 C23 121.5(3) . . ? N20 C22 C21 116.6(3) . . ? C23 C22 C21 121.9(3) . . ? C24 C23 C22 118.9(4) . . ? C24 C23 H23 120.5 . . ? C22 C23 H23 120.5 . . ? C25 C24 C23 119.4(4) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C24 C25 C26 118.5(4) . . ? C24 C25 H25 120.7 . . ? C26 C25 H25 120.7 . . ? N20 C26 C25 123.8(4) . . ? N20 C26 H26 118.1 . . ? C25 C26 H26 118.1 . . ? N10 Mn1 N14 172.64(10) 4_576 . ? N10 Mn1 N15 91.42(10) 4_576 . ? N14 Mn1 N15 81.36(10) . . ? N10 Mn1 N20 89.52(10) 4_576 . ? N14 Mn1 N20 97.82(10) . . ? N15 Mn1 N20 164.11(10) . . ? N10 Mn1 N19 85.24(10) 4_576 . ? N14 Mn1 N19 96.47(10) . . ? N15 Mn1 N19 92.64(10) . . ? N20 Mn1 N19 71.63(10) . . ? N10 Mn1 N17 93.18(10) 4_576 2_655 ? N14 Mn1 N17 86.51(10) . 2_655 ? N15 Mn1 N17 98.60(10) . 2_655 ? N20 Mn1 N17 97.18(10) . 2_655 ? N19 Mn1 N17 168.69(11) . 2_655 ? N1 Mn2 N3 165.51(11) . 3_775 ? N1 Mn2 N4 92.33(11) . . ? N3 Mn2 N4 93.31(10) 3_775 . ? N1 Mn2 N11 94.14(11) . . ? N3 Mn2 N11 97.35(11) 3_775 . ? N4 Mn2 N11 104.45(10) . . ? N1 Mn2 N7 90.12(10) . 3_775 ? N3 Mn2 N7 82.15(10) 3_775 3_775 ? N4 Mn2 N7 170.05(11) . 3_775 ? N11 Mn2 N7 84.98(10) . 3_775 ? N1 Mn2 N2 71.37(11) . . ? N3 Mn2 N2 95.24(11) 3_775 . ? N4 Mn2 N2 90.51(10) . . ? N11 Mn2 N2 159.78(10) . . ? N7 Mn2 N2 81.13(10) 3_775 . ? C1 N1 C5 117.8(3) . . ? C1 N1 Mn2 123.5(3) . . ? C5 N1 Mn2 118.5(2) . . ? C10 N2 C6 118.5(3) . . ? C10 N2 Mn2 125.1(2) . . ? C6 N2 Mn2 113.9(2) . . ? C11 N3 N4 104.5(3) . . ? C11 N3 Mn2 124.6(2) . 3_775 ? N4 N3 Mn2 128.7(2) . 3_775 ? N5 N4 N3 108.9(3) . . ? N5 N4 Mn2 117.1(2) . . ? N3 N4 Mn2 130.1(2) . . ? N4 N5 N6 110.1(3) . . ? C11 N6 N5 105.1(3) . . ? C13 N7 N8 105.4(3) . . ? C13 N7 Mn2 126.1(2) . 3_775 ? N8 N7 Mn2 127.0(2) . 3_775 ? N9 N8 N7 108.6(3) . . ? N8 N9 N10 109.2(3) . . ? C13 N10 N9 103.9(3) . . ? C13 N10 Mn1 135.8(2) . 4_675 ? N9 N10 Mn1 118.7(2) . 4_675 ? C14 N11 N12 105.2(3) . . ? C14 N11 Mn2 137.7(2) . . ? N12 N11 Mn2 115.0(2) . . ? N13 N12 N11 108.8(3) . . ? N12 N13 N14 109.3(3) . . ? C14 N14 N13 105.2(3) . . ? C14 N14 Mn1 131.0(2) . . ? N13 N14 Mn1 122.9(2) . . ? C16 N15 N16 104.9(3) . . ? C16 N15 Mn1 128.1(2) . . ? N16 N15 Mn1 123.3(2) . . ? N17 N16 N15 108.9(3) . . ? N16 N17 N18 110.0(3) . . ? N16 N17 Mn1 117.1(2) . 2_645 ? N18 N17 Mn1 131.3(2) . 2_645 ? C16 N18 N17 103.9(3) . . ? C17 N19 C21 118.3(3) . . ? C17 N19 Mn1 124.6(2) . . ? C21 N19 Mn1 116.7(2) . . ? C26 N20 C22 117.9(3) . . ? C26 N20 Mn1 123.4(2) . . ? C22 N20 Mn1 118.4(2) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.774 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.078