Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Parthasarathi Dastidar' _publ_contact_author_address ; Analytical Science Discipline Central Salt & Marine Chemicals Research Institute G B Marg Bhavnagar Gujarat 364002 INDIA ; _publ_contact_author_email PARTHOD123@REDIFFMAIL.COM _publ_section_title ; Supramolecular Structural Diversities in the MOFs Derived from Pyridylamide Ligands: Studying the Effects of Ligating Topologies, Hydrogen Bonding Backbone of the Ligands and Counter Anions ; loop_ _publ_author_name 'Parthasarathi Dastidar' 'Amitava Das' 'D. Krishna Kumar' data_kkb56c1m _database_code_depnum_ccdc_archive 'CCDC 625903' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 N3 O5 Zn' _chemical_formula_weight 382.67 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 TRICLINIC _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9642(10) _cell_length_b 9.1534(12) _cell_length_c 10.9628(14) _cell_angle_alpha 84.746(2) _cell_angle_beta 79.247(2) _cell_angle_gamma 79.584(2) _cell_volume 770.83(17) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 1.625 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6244 _exptl_absorpt_correction_T_max 0.8810 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4575 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3363 _reflns_number_gt 2819 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0743P)^2^+0.3428P] 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 3363 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1380 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _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 Zn1 Zn 0.37260(5) 0.38746(4) 0.42092(4) 0.03498(17) Uani 1 1 d . . . N1 N 0.2598(4) 0.2902(3) 0.5993(3) 0.0364(7) Uani 1 1 d . . . C2 C 0.3246(5) 0.1460(4) 0.6263(4) 0.0431(9) Uani 1 1 d . . . H2 H 0.4160 0.0981 0.5704 0.052 Uiso 1 1 calc R . . C3 C 0.2616(5) 0.0682(5) 0.7318(4) 0.0488(10) Uani 1 1 d . . . H3 H 0.3087 -0.0311 0.7463 0.059 Uiso 1 1 calc R . . C4 C 0.1260(5) 0.1382(4) 0.8180(4) 0.0432(9) Uani 1 1 d . . . H4 H 0.0807 0.0868 0.8902 0.052 Uiso 1 1 calc R . . C5 C 0.0608(4) 0.2875(4) 0.7926(3) 0.0327(7) Uani 1 1 d . . . C6 C 0.1301(4) 0.3580(4) 0.6819(3) 0.0339(7) Uani 1 1 d . . . H6 H 0.0842 0.4569 0.6643 0.041 Uiso 1 1 calc R . . N7 N -0.0702(4) 0.3729(3) 0.8733(3) 0.0359(7) Uani 1 1 d . . . H7 H -0.1053 0.4625 0.8466 0.043 Uiso 1 1 calc R . . C8 C -0.1474(5) 0.3298(4) 0.9885(4) 0.0416(9) Uani 1 1 d . . . O9 O -0.1177(5) 0.2039(4) 1.0332(3) 0.0758(12) Uani 1 1 d . . . C10 C -0.2777(4) 0.4465(4) 1.0596(3) 0.0342(7) Uani 1 1 d . . . C11 C -0.3704(5) 0.3972(4) 1.1711(3) 0.0395(8) Uani 1 1 d . . . H11 H -0.3449 0.2974 1.1973 0.047 Uiso 1 1 calc R . . N12 N -0.4940(4) 0.4855(4) 1.2427(3) 0.0392(7) Uani 1 1 d . . . C13 C -0.5278(5) 0.6280(4) 1.2037(4) 0.0418(9) Uani 1 1 d . . . H13 H -0.6157 0.6907 1.2513 0.050 Uiso 1 1 calc R . . C14 C -0.4391(6) 0.6866(4) 1.0969(4) 0.0458(9) Uani 1 1 d . . . H14 H -0.4655 0.7873 1.0741 0.055 Uiso 1 1 calc R . . C15 C -0.3109(5) 0.5958(4) 1.0235(4) 0.0422(9) Uani 1 1 d . . . H15 H -0.2481 0.6341 0.9513 0.051 Uiso 1 1 calc R . . O16 O 0.6103(4) 0.3164(5) 0.4625(4) 0.0868(13) Uani 1 1 d . . . C17 C 0.7464(5) 0.3154(5) 0.5008(3) 0.0404(9) Uani 1 1 d . . . O18 O 0.7861(4) 0.4193(3) 0.5506(3) 0.0537(7) Uani 1 1 d . . . C19 C 0.8740(6) 0.1741(5) 0.4913(5) 0.0632(13) Uani 1 1 d . . . H19A H 0.8226 0.0953 0.5393 0.095 Uiso 1 1 calc R . . H19B H 0.9751 0.1863 0.5227 0.095 Uiso 1 1 calc R . . H19C H 0.9065 0.1497 0.4058 0.095 Uiso 1 1 calc R . . O20 O 0.3679(4) 0.2015(3) 0.3382(3) 0.0516(7) Uani 1 1 d . . . C21 C 0.2513(5) 0.2197(4) 0.2713(3) 0.0421(9) Uani 1 1 d . . . O22 O 0.1518(4) 0.3380(3) 0.2603(3) 0.0616(9) Uani 1 1 d . . . C23 C 0.2420(7) 0.0879(5) 0.2032(5) 0.0627(12) Uani 1 1 d . . . H23A H 0.1344 0.1036 0.1725 0.094 Uiso 1 1 calc R . . H23B H 0.2486 0.0005 0.2587 0.094 Uiso 1 1 calc R . . H23C H 0.3368 0.0752 0.1347 0.094 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0323(2) 0.0324(2) 0.0358(3) -0.00726(16) 0.00062(16) 0.00208(16) N1 0.0324(15) 0.0369(16) 0.0356(16) -0.0049(13) 0.0001(12) 0.0004(12) C2 0.0389(19) 0.039(2) 0.045(2) -0.0057(16) 0.0010(16) 0.0031(16) C3 0.051(2) 0.033(2) 0.055(3) 0.0015(17) -0.0022(19) 0.0031(17) C4 0.048(2) 0.037(2) 0.041(2) 0.0026(16) -0.0009(17) -0.0040(17) C5 0.0267(15) 0.0260(16) 0.0416(19) -0.0104(14) 0.0014(13) 0.0024(13) C6 0.0307(16) 0.0250(16) 0.0421(19) -0.0080(14) -0.0012(14) 0.0028(13) N7 0.0355(15) 0.0294(15) 0.0352(16) -0.0024(12) 0.0044(12) 0.0041(12) C8 0.0368(18) 0.044(2) 0.037(2) 0.0004(16) 0.0029(15) 0.0005(16) O9 0.089(2) 0.053(2) 0.054(2) 0.0152(16) 0.0264(18) 0.0198(18) C10 0.0329(17) 0.0352(18) 0.0315(17) -0.0063(14) -0.0022(13) 0.0008(14) C11 0.0432(19) 0.0294(18) 0.040(2) -0.0043(15) 0.0027(16) 0.0014(15) N12 0.0380(15) 0.0395(17) 0.0350(16) -0.0042(13) 0.0035(13) -0.0020(13) C13 0.0403(19) 0.041(2) 0.039(2) -0.0045(16) -0.0027(16) 0.0018(16) C14 0.058(2) 0.0309(19) 0.042(2) -0.0004(16) -0.0013(18) 0.0035(17) C15 0.047(2) 0.035(2) 0.039(2) -0.0065(15) 0.0055(16) -0.0040(16) O16 0.0379(17) 0.138(4) 0.080(3) 0.020(3) -0.0157(17) -0.012(2) C17 0.0312(17) 0.055(2) 0.0281(17) 0.0071(16) 0.0044(14) -0.0041(16) O18 0.0504(16) 0.0431(16) 0.0574(18) -0.0074(14) 0.0063(14) 0.0051(13) C19 0.060(3) 0.032(2) 0.091(4) -0.025(2) 0.004(3) 0.0026(19) O20 0.0706(19) 0.0435(16) 0.0402(15) -0.0064(12) -0.0076(14) -0.0080(14) C21 0.055(2) 0.0327(19) 0.0327(19) -0.0037(15) 0.0084(17) -0.0071(17) O22 0.068(2) 0.0364(16) 0.065(2) -0.0023(14) 0.0124(16) 0.0059(14) C23 0.084(4) 0.052(3) 0.056(3) -0.006(2) -0.017(3) -0.014(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 Zn1 O18 1.992(3) 2_666 ? Zn1 O16 2.009(3) . ? Zn1 O20 2.010(3) . ? Zn1 N1 2.177(3) . ? Zn1 N12 2.236(3) 1_654 ? N1 C6 1.340(4) . ? N1 C2 1.355(5) . ? C2 C3 1.363(6) . ? C2 H2 0.9300 . ? C3 C4 1.396(6) . ? C3 H3 0.9300 . ? C4 C5 1.393(5) . ? C4 H4 0.9300 . ? C5 C6 1.389(5) . ? C5 N7 1.403(4) . ? C6 H6 0.9300 . ? N7 C8 1.355(5) . ? N7 H7 0.8600 . ? C8 O9 1.211(5) . ? C8 C10 1.509(5) . ? C10 C15 1.379(5) . ? C10 C11 1.388(5) . ? C11 N12 1.334(4) . ? C11 H11 0.9300 . ? N12 C13 1.331(5) . ? N12 Zn1 2.236(3) 1_456 ? C13 C14 1.368(5) . ? C13 H13 0.9300 . ? C14 C15 1.375(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O16 C17 1.231(5) . ? C17 O18 1.254(5) . ? C17 C19 1.492(6) . ? O18 Zn1 1.992(3) 2_666 ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? O20 C21 1.267(5) . ? C21 O22 1.231(5) . ? C21 C23 1.495(6) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O18 Zn1 O16 130.30(17) 2_666 . ? O18 Zn1 O20 135.45(14) 2_666 . ? O16 Zn1 O20 94.20(17) . . ? O18 Zn1 N1 91.77(11) 2_666 . ? O16 Zn1 N1 89.59(13) . . ? O20 Zn1 N1 90.46(12) . . ? O18 Zn1 N12 89.99(12) 2_666 1_654 ? O16 Zn1 N12 86.52(13) . 1_654 ? O20 Zn1 N12 90.81(12) . 1_654 ? N1 Zn1 N12 175.99(11) . 1_654 ? C6 N1 C2 117.7(3) . . ? C6 N1 Zn1 126.2(2) . . ? C2 N1 Zn1 116.1(2) . . ? N1 C2 C3 122.8(4) . . ? N1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C2 C3 C4 119.7(4) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 118.0(3) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? C6 C5 C4 118.7(3) . . ? C6 C5 N7 117.3(3) . . ? C4 C5 N7 124.0(3) . . ? N1 C6 C5 123.1(3) . . ? N1 C6 H6 118.5 . . ? C5 C6 H6 118.5 . . ? C8 N7 C5 127.2(3) . . ? C8 N7 H7 116.4 . . ? C5 N7 H7 116.4 . . ? O9 C8 N7 122.7(4) . . ? O9 C8 C10 120.5(3) . . ? N7 C8 C10 116.7(3) . . ? C15 C10 C11 118.2(3) . . ? C15 C10 C8 125.7(3) . . ? C11 C10 C8 116.1(3) . . ? N12 C11 C10 123.4(3) . . ? N12 C11 H11 118.3 . . ? C10 C11 H11 118.3 . . ? C13 N12 C11 117.3(3) . . ? C13 N12 Zn1 124.2(2) . 1_456 ? C11 N12 Zn1 118.5(2) . 1_456 ? N12 C13 C14 123.0(3) . . ? N12 C13 H13 118.5 . . ? C14 C13 H13 118.5 . . ? C13 C14 C15 119.7(4) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C10 118.4(3) . . ? C14 C15 H15 120.8 . . ? C10 C15 H15 120.8 . . ? C17 O16 Zn1 160.6(4) . . ? O16 C17 O18 126.6(4) . . ? O16 C17 C19 116.6(5) . . ? O18 C17 C19 116.7(4) . . ? C17 O18 Zn1 122.5(3) . 2_666 ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 O20 Zn1 112.2(3) . . ? O22 C21 O20 123.2(4) . . ? O22 C21 C23 121.0(4) . . ? O20 C21 C23 115.8(4) . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7 O22 0.86 2.09 2.931(4) 165.5 2_566 C6 H6 O22 0.93 2.48 3.274(4) 142.9 2_566 C13 H13 O18 0.93 2.56 3.117(5) 118.6 2_567 C15 H15 O22 0.93 2.31 3.180(5) 155.8 2_566 _diffrn_measured_fraction_theta_max 0.876 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.876 _refine_diff_density_max 0.746 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.092 # Attachment '2_kb375lm_FINAL.cif' data_kb375lm _database_code_depnum_ccdc_archive 'CCDC 625904' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 B F4.17 N3 O2 Zn0.50' _chemical_formula_weight 340.00 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.486(4) _cell_length_b 9.551(4) _cell_length_c 16.351(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.79(2) _cell_angle_gamma 90.00 _cell_volume 1313.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 686 _exptl_absorpt_coefficient_mu 1.038 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7191 _exptl_absorpt_correction_T_max 0.9499 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4162 _diffrn_reflns_av_R_equivalents 0.0844 _diffrn_reflns_av_sigmaI/netI 0.1227 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 22.49 _reflns_number_total 1703 _reflns_number_gt 1030 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0943P)^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 1703 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1225 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.1757 _refine_ls_wR_factor_gt 0.1511 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 1.0000 0.5000 0.0000 0.0171(5) Uani 1 2 d S . . N1 N 0.9146(8) 0.7857(7) 0.4757(4) 0.0177(17) Uani 1 1 d . . . C2 C 0.8693(10) 0.7104(8) 0.5305(5) 0.018(2) Uani 1 1 d . . . H2 H 0.8812 0.7435 0.5845 0.022 Uiso 1 1 calc R . . C3 C 0.8007(11) 0.5767(9) 0.5137(6) 0.025(2) Uani 1 1 d . . . H3 H 0.7681 0.5267 0.5573 0.030 Uiso 1 1 calc R . . C4 C 0.7798(11) 0.5174(10) 0.4380(6) 0.032(2) Uani 1 1 d . . . H4 H 0.7352 0.4291 0.4278 0.038 Uiso 1 1 calc R . . C5 C 0.8272(11) 0.5942(10) 0.3808(6) 0.027(2) Uani 1 1 d . . . C6 C 0.8931(10) 0.7238(9) 0.4028(6) 0.023(2) Uani 1 1 d . . . H6 H 0.9271 0.7746 0.3599 0.027 Uiso 1 1 calc R . . N7 N 0.8051(10) 0.5462(7) 0.2997(5) 0.032(2) Uani 1 1 d . . . H7 H 0.8097 0.6089 0.2623 0.039 Uiso 1 1 calc R . . C8 C 0.7769(11) 0.4123(11) 0.2714(6) 0.031(3) Uani 1 1 d . . . O9 O 0.7783(7) 0.3155(6) 0.3171(4) 0.0270(16) Uani 1 1 d . . . C10 C 0.7417(11) 0.3975(10) 0.1811(6) 0.026(2) Uani 1 1 d . . . C11 C 0.6232(11) 0.3070(10) 0.1372(6) 0.030(2) Uani 1 1 d . . . H11 H 0.5617 0.2561 0.1696 0.036 Uiso 1 1 calc R . . C12 C 0.5901(11) 0.2866(11) 0.0540(6) 0.035(3) Uani 1 1 d . . . H12 H 0.5101 0.2291 0.0280 0.042 Uiso 1 1 calc R . . C13 C 0.6866(10) 0.3593(9) 0.0174(6) 0.026(2) Uani 1 1 d . . . H13 H 0.6759 0.3549 -0.0399 0.031 Uiso 1 1 calc R . . N14 N 0.8113(9) 0.4480(7) 0.0592(4) 0.0223(19) Uani 1 1 d . . . C15 C 0.8352(11) 0.4675(8) 0.1393(6) 0.023(2) Uani 1 1 d . . . H15 H 0.9137 0.5274 0.1645 0.028 Uiso 1 1 calc R . . O16 O 1.1759(7) 0.5559(6) 0.1184(4) 0.0226(15) Uani 1 1 d . . . B17 B 0.3287(15) 0.3713(11) 0.3078(7) 0.033(3) Uani 1 1 d . . . F18 F 0.3763(6) 0.3813(5) 0.2392(3) 0.0325(14) Uani 1 1 d . . . F19 F 0.1674(8) 0.3098(8) 0.2848(5) 0.050(2) Uiso 0.83 1 d P . . F20 F 0.293(3) 0.5159(18) 0.3240(12) 0.042(5) Uiso 0.36 1 d P . . F21 F 0.4297(19) 0.4417(19) 0.3787(11) 0.060(5) Uiso 0.45 1 d P . . F22 F 0.432(2) 0.2446(18) 0.3471(11) 0.025(4) Uiso 0.32 1 d P . . F23 F 0.333(3) 0.239(3) 0.3370(16) 0.030(7) Uiso 0.20 1 d P . . F24 F 0.4331(15) 0.3121(17) 0.3728(9) 0.032(4) Uiso 0.40 1 d P . . F25 F 0.197(4) 0.504(3) 0.3005(17) 0.029(7) Uiso 0.19 1 d P . . F26 F 0.375(4) 0.491(3) 0.3489(17) 0.022(5) Uiso 0.23 1 d P . . F27 F 0.166(2) 0.405(3) 0.2857(13) 0.018(6) Uiso 0.20 1 d P . . H16A H 1.2491 0.4977 0.1576 0.006(18) Uiso 1 1 d R . . H16B H 1.1824 0.6377 0.1436 0.02(2) 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 Zn1 0.0308(9) 0.0150(7) 0.0064(8) -0.0018(7) 0.0056(6) 0.0010(8) N1 0.027(4) 0.019(4) 0.008(4) 0.006(4) 0.005(3) 0.007(3) C2 0.036(6) 0.015(5) 0.005(5) -0.002(4) 0.007(4) 0.005(4) C3 0.048(7) 0.016(5) 0.013(6) 0.007(4) 0.012(5) 0.006(4) C4 0.041(6) 0.017(5) 0.041(7) -0.006(5) 0.020(5) 0.010(5) C5 0.025(6) 0.035(6) 0.024(7) -0.002(5) 0.015(5) 0.008(4) C6 0.035(6) 0.021(5) 0.014(6) -0.003(4) 0.012(4) 0.005(4) N7 0.063(6) 0.010(4) 0.029(6) 0.002(4) 0.022(5) 0.004(4) C8 0.029(6) 0.044(7) 0.022(7) -0.011(6) 0.009(5) 0.009(5) O9 0.053(4) 0.016(4) 0.015(4) 0.011(3) 0.017(3) -0.002(3) C10 0.037(6) 0.034(6) 0.009(6) 0.000(5) 0.011(5) 0.008(5) C11 0.030(6) 0.047(7) 0.013(7) 0.008(5) 0.009(5) 0.005(5) C12 0.030(6) 0.052(7) 0.028(7) 0.000(5) 0.019(5) -0.009(5) C13 0.034(6) 0.035(6) 0.011(6) -0.005(5) 0.010(5) 0.001(5) N14 0.047(5) 0.014(4) 0.005(5) -0.006(3) 0.003(4) 0.000(3) C15 0.037(6) 0.010(5) 0.024(6) 0.000(4) 0.006(5) 0.004(4) O16 0.038(4) 0.016(3) 0.015(4) -0.005(3) 0.003(3) 0.002(3) B17 0.061(9) 0.019(6) 0.020(8) -0.004(5) 0.011(7) -0.015(6) F18 0.044(3) 0.044(3) 0.013(3) 0.012(3) 0.016(3) 0.010(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 Zn1 N14 2.042(7) . ? Zn1 N14 2.042(7) 3_765 ? Zn1 N1 2.189(7) 2_745 ? Zn1 N1 2.189(7) 4_575 ? Zn1 O16 2.341(6) . ? Zn1 O16 2.341(6) 3_765 ? N1 C2 1.250(10) . ? N1 C6 1.322(10) . ? N1 Zn1 2.189(7) 2_755 ? C2 C3 1.415(12) . ? C2 H2 0.9300 . ? C3 C4 1.352(12) . ? C3 H3 0.9300 . ? C4 C5 1.295(12) . ? C4 H4 0.9300 . ? C5 C6 1.386(12) . ? C5 N7 1.391(12) . ? C6 H6 0.9300 . ? N7 C8 1.370(12) . ? N7 H7 0.8600 . ? C8 O9 1.187(11) . ? C8 C10 1.474(13) . ? C10 C15 1.300(11) . ? C10 C11 1.441(13) . ? C11 C12 1.364(12) . ? C11 H11 0.9300 . ? C12 C13 1.282(11) . ? C12 H12 0.9300 . ? C13 N14 1.452(11) . ? C13 H13 0.9300 . ? N14 C15 1.311(11) . ? C15 H15 0.9300 . ? O16 H16A 0.9988 . ? O16 H16B 0.8812 . ? B17 F18 1.246(12) . ? B17 F23 1.35(3) . ? B17 F26 1.35(3) . ? B17 F24 1.407(18) . ? B17 F27 1.42(2) . ? B17 F20 1.45(2) . ? B17 F19 1.490(14) . ? B17 F21 1.50(2) . ? B17 F22 1.58(2) . ? B17 F25 1.68(3) . ? 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 N14 Zn1 N14 179.998(1) . 3_765 ? N14 Zn1 N1 87.0(3) . 2_745 ? N14 Zn1 N1 93.0(3) 3_765 2_745 ? N14 Zn1 N1 93.0(3) . 4_575 ? N14 Zn1 N1 87.0(3) 3_765 4_575 ? N1 Zn1 N1 180.0 2_745 4_575 ? N14 Zn1 O16 96.7(3) . . ? N14 Zn1 O16 83.3(3) 3_765 . ? N1 Zn1 O16 84.5(2) 2_745 . ? N1 Zn1 O16 95.5(2) 4_575 . ? N14 Zn1 O16 83.3(3) . 3_765 ? N14 Zn1 O16 96.7(3) 3_765 3_765 ? N1 Zn1 O16 95.5(2) 2_745 3_765 ? N1 Zn1 O16 84.5(2) 4_575 3_765 ? O16 Zn1 O16 180.0 . 3_765 ? C2 N1 C6 111.8(8) . . ? C2 N1 Zn1 122.3(6) . 2_755 ? C6 N1 Zn1 125.7(6) . 2_755 ? N1 C2 C3 122.6(8) . . ? N1 C2 H2 118.7 . . ? C3 C2 H2 118.7 . . ? C4 C3 C2 123.7(9) . . ? C4 C3 H3 118.1 . . ? C2 C3 H3 118.1 . . ? C5 C4 C3 114.2(9) . . ? C5 C4 H4 122.9 . . ? C3 C4 H4 122.9 . . ? C4 C5 C6 118.2(10) . . ? C4 C5 N7 119.2(9) . . ? C6 C5 N7 122.6(9) . . ? N1 C6 C5 129.5(8) . . ? N1 C6 H6 115.3 . . ? C5 C6 H6 115.3 . . ? C8 N7 C5 128.6(8) . . ? C8 N7 H7 115.7 . . ? C5 N7 H7 115.7 . . ? O9 C8 N7 121.9(9) . . ? O9 C8 C10 122.7(9) . . ? N7 C8 C10 115.4(9) . . ? C15 C10 C11 118.8(9) . . ? C15 C10 C8 115.0(9) . . ? C11 C10 C8 126.1(9) . . ? C12 C11 C10 128.1(9) . . ? C12 C11 H11 115.9 . . ? C10 C11 H11 115.9 . . ? C13 C12 C11 109.2(10) . . ? C13 C12 H12 125.4 . . ? C11 C12 H12 125.4 . . ? C12 C13 N14 124.6(9) . . ? C12 C13 H13 117.7 . . ? N14 C13 H13 117.7 . . ? C15 N14 C13 123.9(8) . . ? C15 N14 Zn1 114.4(6) . . ? C13 N14 Zn1 119.2(5) . . ? C10 C15 N14 115.3(9) . . ? C10 C15 H15 122.3 . . ? N14 C15 H15 122.3 . . ? Zn1 O16 H16A 132.5 . . ? Zn1 O16 H16B 125.5 . . ? H16A O16 H16B 101.5 . . ? F18 B17 F23 113.3(14) . . ? F18 B17 F26 106.0(12) . . ? F23 B17 F26 128(2) . . ? F18 B17 F24 117.6(11) . . ? F23 B17 F24 51.0(14) . . ? F26 B17 F24 81.7(17) . . ? F18 B17 F27 100.2(12) . . ? F23 B17 F27 106.5(17) . . ? F26 B17 F27 97.9(18) . . ? F24 B17 F27 140.9(13) . . ? F18 B17 F20 101.1(10) . . ? F23 B17 F20 145.6(16) . . ? F26 B17 F20 32.5(11) . . ? F24 B17 F20 111.8(14) . . ? F27 B17 F20 66.9(14) . . ? F18 B17 F19 101.7(9) . . ? F23 B17 F19 72.7(14) . . ? F26 B17 F19 130.5(16) . . ? F24 B17 F19 119.7(10) . . ? F27 B17 F19 36.5(10) . . ? F20 B17 F19 102.5(13) . . ? F18 B17 F21 116.1(11) . . ? F23 B17 F21 99.1(16) . . ? F26 B17 F21 31.3(13) . . ? F24 B17 F21 50.4(9) . . ? F27 B17 F21 121.8(14) . . ? F20 B17 F21 62.7(11) . . ? F19 B17 F21 141.1(11) . . ? F18 B17 F22 101.3(10) . . ? F23 B17 F22 31.9(11) . . ? F26 B17 F22 109.7(19) . . ? F24 B17 F22 29.1(7) . . ? F27 B17 F22 138.4(14) . . ? F20 B17 F22 140.8(15) . . ? F19 B17 F22 104.0(10) . . ? F21 B17 F22 78.5(11) . . ? F18 B17 F25 99.9(12) . . ? F23 B17 F25 135.8(18) . . ? F26 B17 F25 62.8(16) . . ? F24 B17 F25 134.4(14) . . ? F27 B17 F25 36.4(12) . . ? F20 B17 F25 30.8(11) . . ? F19 B17 F25 72.6(13) . . ? F21 B17 F25 91.2(14) . . ? F22 B17 F25 158.8(14) . . ? F27 F19 B17 67.5(15) . . ? F27 F19 F23 113.8(18) . . ? B17 F19 F23 49.7(10) . . ? F26 F20 F25 154(4) . . ? F26 F20 B17 67(2) . . ? F25 F20 B17 90(3) . . ? F26 F20 F21 12(2) . . ? F25 F20 F21 142(3) . . ? B17 F20 F21 60.5(11) . . ? F26 F20 F27 120(3) . . ? F25 F20 F27 35(2) . . ? B17 F20 F27 55.7(11) . . ? F21 F20 F27 110.1(15) . . ? F26 F21 F24 124(3) . . ? F26 F21 B17 64(2) . . ? F24 F21 B17 60.7(10) . . ? F26 F21 F20 12(2) . . ? F24 F21 F20 116.0(14) . . ? B17 F21 F20 56.8(10) . . ? F24 F22 F23 95(3) . . ? F24 F22 B17 62.8(17) . . ? F23 F22 B17 58(2) . . ? F22 F23 F24 40.2(18) . . ? F22 F23 B17 90(3) . . ? F24 F23 B17 67.2(16) . . ? F22 F23 F19 146(3) . . ? F24 F23 F19 121(2) . . ? B17 F23 F19 57.6(12) . . ? F22 F24 F23 44.5(18) . . ? F22 F24 F21 152(2) . . ? F23 F24 F21 127(2) . . ? F22 F24 B17 88(2) . . ? F23 F24 B17 61.9(15) . . ? F21 F24 B17 68.9(11) . . ? F20 F25 F27 116(4) . . ? F20 F25 F26 13(2) . . ? F27 F25 F26 104(3) . . ? F20 F25 B17 59(2) . . ? F27 F25 B17 57.4(19) . . ? F26 F25 B17 48.6(12) . . ? F21 F26 F20 155(4) . . ? F21 F26 B17 85(3) . . ? F20 F26 B17 80(2) . . ? F21 F26 F25 142(3) . . ? F20 F26 F25 14(2) . . ? B17 F26 F25 68.5(16) . . ? F19 F27 F25 160(3) . . ? F19 F27 B17 76.1(16) . . ? F25 F27 B17 86(2) . . ? F19 F27 F20 132(2) . . ? F25 F27 F20 29.2(18) . . ? B17 F27 F20 57.4(12) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7 F19 0.86 2.09 2.896(11) 156.7 2_655 O16 H16A F18 1.00 1.95 2.943(8) 175.1 1_655 O16 H16B O9 0.88 1.83 2.702(8) 169.5 2_755 C2 H2 F19 0.93 2.29 3.084(11) 143.2 3_666 C6 H6 F19 0.93 2.42 3.149(12) 135.6 2_655 C13 H13 O16 0.93 2.10 2.767(11) 128.0 3_765 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 22.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.705 _refine_diff_density_min -0.538 _refine_diff_density_rms 0.115 # Attachment '3_kkb56d3m_FINAL.cif' data_kkb56d3m _database_code_depnum_ccdc_archive 'CCDC 625905' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H9 Cl2 N3 O Zn' _chemical_formula_weight 335.48 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' Cl Cl 0.1484 0.1585 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.805(3) _cell_length_b 13.773(6) _cell_length_c 13.362(4) _cell_angle_alpha 90.00 _cell_angle_beta 119.810(17) _cell_angle_gamma 90.00 _cell_volume 1246.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ROD _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.788 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 2.388 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.4974 _exptl_absorpt_correction_T_max 0.8700 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6632 _diffrn_reflns_av_R_equivalents 0.0687 _diffrn_reflns_av_sigmaI/netI 0.1015 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 28.02 _reflns_number_total 2781 _reflns_number_gt 1701 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^+16.6832P] 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 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1586 _refine_ls_R_factor_gt 0.1014 _refine_ls_wR_factor_ref 0.2040 _refine_ls_wR_factor_gt 0.1876 _refine_ls_goodness_of_fit_ref 1.174 _refine_ls_restrained_S_all 1.174 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn -0.10351(18) 0.61590(10) 0.20264(9) 0.0369(4) Uani 1 1 d . . . N1 N 0.0910(13) 0.5086(6) 0.2973(7) 0.035(2) Uani 1 1 d . . . C2 C 0.0965(15) 0.4717(8) 0.3913(8) 0.035(2) Uani 1 1 d . . . H2 H 0.0010 0.4909 0.4094 0.042 Uiso 1 1 calc R . . C3 C 0.2369(16) 0.4069(8) 0.4614(8) 0.039(3) Uani 1 1 d . . . H3 H 0.2384 0.3845 0.5274 0.046 Uiso 1 1 calc R . . C4 C 0.3761(18) 0.3745(9) 0.4352(10) 0.046(3) Uani 1 1 d . . . H4 H 0.4691 0.3283 0.4811 0.056 Uiso 1 1 calc R . . C5 C 0.3747(18) 0.4114(7) 0.3409(11) 0.040(3) Uani 1 1 d . . . C6 C 0.2284(19) 0.4775(8) 0.2713(9) 0.044(3) Uani 1 1 d . . . H6 H 0.2252 0.5008 0.2051 0.053 Uiso 1 1 calc R . . N7A N 0.5149(18) 0.3671(9) 0.2241(10) 0.023(3) Uiso 0.64 1 d P . . N7B N 0.441(3) 0.3855(18) 0.261(2) 0.032(5) Uiso 0.36 1 d P . . C8A C 0.557(2) 0.3772(10) 0.3351(11) 0.017(3) Uiso 0.62 1 d P . . C8B C 0.631(4) 0.3635(19) 0.317(2) 0.031(6) Uiso 0.38 1 d P . . O9 O 0.7229(9) 0.3583(5) 0.4180(5) 0.0285(15) Uani 1 1 d . . . C10 C 0.6693(19) 0.3378(8) 0.2021(12) 0.051(3) Uani 1 1 d . . . C11 C 0.8078(18) 0.2666(8) 0.2594(10) 0.046(3) Uani 1 1 d . . . H11 H 0.8175 0.2402 0.3260 0.055 Uiso 1 1 calc R . . N12 N 0.9282(12) 0.2342(6) 0.2233(6) 0.0305(19) Uani 1 1 d . . . C13 C 0.9104(15) 0.2749(7) 0.1278(8) 0.031(2) Uani 1 1 d . . . H13 H 0.9925 0.2529 0.1006 0.038 Uiso 1 1 calc R . . C14 C 0.7782(15) 0.3469(7) 0.0677(8) 0.034(2) Uani 1 1 d . . . H14 H 0.7732 0.3744 0.0027 0.041 Uiso 1 1 calc R . . C15 C 0.6537(16) 0.3775(9) 0.1055(11) 0.049(3) Uani 1 1 d . . . H15 H 0.5595 0.4251 0.0653 0.059 Uiso 1 1 calc R . . Cl16 Cl -0.1358(4) 0.6071(2) 0.02713(19) 0.0466(7) Uani 1 1 d . . . Cl17 Cl -0.3589(4) 0.6178(2) 0.2306(2) 0.0413(6) Uani 1 1 d . . . H7 H 0.39(2) 0.389(11) 0.180(12) 0.09(5) Uiso 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 Zn1 0.0397(7) 0.0477(8) 0.0209(5) 0.0003(6) 0.0133(5) -0.0069(7) N1 0.035(5) 0.046(5) 0.026(4) -0.007(4) 0.017(4) -0.019(4) C2 0.031(6) 0.055(7) 0.029(5) 0.002(5) 0.022(4) 0.008(5) C3 0.053(7) 0.035(7) 0.029(5) 0.001(4) 0.022(5) 0.009(5) C4 0.056(7) 0.034(7) 0.059(7) -0.007(5) 0.036(6) -0.005(6) C5 0.063(8) 0.006(5) 0.078(8) -0.013(5) 0.054(7) -0.008(5) C6 0.076(9) 0.036(6) 0.040(6) -0.018(5) 0.044(6) -0.024(6) O9 0.032(4) 0.031(4) 0.024(3) -0.003(3) 0.015(3) 0.010(3) C10 0.068(9) 0.023(6) 0.097(10) -0.022(6) 0.068(8) -0.012(6) C11 0.072(9) 0.035(7) 0.059(7) -0.012(5) 0.053(7) -0.010(6) N12 0.040(5) 0.028(5) 0.023(4) -0.008(3) 0.015(4) 0.001(4) C13 0.033(6) 0.037(6) 0.025(5) -0.007(4) 0.015(4) -0.003(5) C14 0.033(6) 0.027(6) 0.036(5) -0.006(4) 0.013(5) 0.002(5) C15 0.036(6) 0.034(7) 0.074(8) 0.003(6) 0.024(6) 0.009(6) Cl16 0.0472(16) 0.070(2) 0.0207(11) -0.0009(12) 0.0158(11) -0.0026(15) Cl17 0.0421(15) 0.0489(17) 0.0342(12) -0.0011(12) 0.0200(11) -0.0060(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 Zn1 N12 2.039(8) 2_655 ? Zn1 N1 2.044(9) . ? Zn1 Cl17 2.203(3) . ? Zn1 Cl16 2.234(2) . ? N1 C2 1.336(12) . ? N1 C6 1.350(14) . ? C2 C3 1.362(14) . ? C3 C4 1.371(15) . ? C4 C5 1.354(15) . ? C5 C6 1.393(16) . ? C5 N7B 1.44(2) . ? C5 C8A 1.535(17) . ? N7A C8B 1.11(3) . ? N7A C8A 1.358(17) . ? N7A C10 1.434(16) . ? N7B C8A 0.96(2) . ? N7B C8B 1.32(4) . ? C8A O9 1.245(14) . ? C8B O9 1.18(3) . ? C8B C10 1.74(3) . ? C10 C15 1.350(16) . ? C10 C11 1.376(17) . ? C11 N12 1.329(13) . ? N12 C13 1.337(12) . ? N12 Zn1 2.039(8) 2_645 ? C13 C14 1.367(14) . ? C14 C15 1.366(15) . ? 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 N12 Zn1 N1 99.5(3) 2_655 . ? N12 Zn1 Cl17 110.7(3) 2_655 . ? N1 Zn1 Cl17 111.1(2) . . ? N12 Zn1 Cl16 104.5(2) 2_655 . ? N1 Zn1 Cl16 105.7(2) . . ? Cl17 Zn1 Cl16 122.64(11) . . ? C2 N1 C6 117.5(10) . . ? C2 N1 Zn1 121.6(7) . . ? C6 N1 Zn1 120.8(7) . . ? N1 C2 C3 122.3(9) . . ? C2 C3 C4 120.5(10) . . ? C5 C4 C3 118.3(11) . . ? C4 C5 C6 119.4(10) . . ? C4 C5 N7B 139.0(14) . . ? C6 C5 N7B 98.4(13) . . ? C4 C5 C8A 110.6(11) . . ? C6 C5 C8A 129.7(10) . . ? N7B C5 C8A 37.3(10) . . ? N1 C6 C5 121.9(9) . . ? C8B N7A C8A 33.8(14) . . ? C8B N7A C10 85.1(18) . . ? C8A N7A C10 118.9(12) . . ? C8A N7B C8B 34.3(14) . . ? C8A N7B C5 76.5(18) . . ? C8B N7B C5 111(2) . . ? N7B C8A O9 167(2) . . ? N7B C8A N7A 45.0(15) . . ? O9 C8A N7A 121.9(13) . . ? N7B C8A C5 66.1(17) . . ? O9 C8A C5 126.9(11) . . ? N7A C8A C5 111.2(11) . . ? N7A C8B O9 167(3) . . ? N7A C8B N7B 45.6(15) . . ? O9 C8B N7B 122(3) . . ? N7A C8B C10 55.2(14) . . ? O9 C8B C10 137(2) . . ? N7B C8B C10 100.8(19) . . ? C8B O9 C8A 36.2(13) . . ? C15 C10 C11 119.6(10) . . ? C15 C10 N7A 113.4(12) . . ? C11 C10 N7A 126.4(11) . . ? C15 C10 C8B 141.9(13) . . ? C11 C10 C8B 95.0(12) . . ? N7A C10 C8B 39.7(10) . . ? N12 C11 C10 122.6(10) . . ? C11 N12 C13 116.7(9) . . ? C11 N12 Zn1 121.2(7) . 2_645 ? C13 N12 Zn1 121.6(7) . 2_645 ? N12 C13 C14 123.7(10) . . ? C15 C14 C13 118.3(10) . . ? C10 C15 C14 119.1(11) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7A H7 Cl16 0.89(14) 2.48(14) 3.205(12) 138(12) 3_565 _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 28.02 _diffrn_measured_fraction_theta_full 0.921 _refine_diff_density_max 1.079 _refine_diff_density_min -1.123 _refine_diff_density_rms 0.140 # Attachment '6_kkb356hm_FINAL.cif' data_kkb356hm _database_code_depnum_ccdc_archive 'CCDC 625906' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H9 Cd0.50 N4 O4' _chemical_formula_weight 317.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting TRICLINIC _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8782(10) _cell_length_b 8.2339(10) _cell_length_c 9.8945(12) _cell_angle_alpha 93.223(2) _cell_angle_beta 98.037(2) _cell_angle_gamma 112.535(2) _cell_volume 582.76(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour PALE-YELLOW _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.809 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 1.006 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6891 _exptl_absorpt_correction_T_max 0.8888 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3373 _diffrn_reflns_av_R_equivalents 0.0131 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 28.22 _reflns_number_total 2510 _reflns_number_gt 2493 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0557P)^2^+0.1794P] 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 2510 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0810 _refine_ls_wR_factor_gt 0.0807 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.151 _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 0.5000 0.5000 1.0000 0.02855(10) Uani 1 2 d S . . N1 N 0.4433(3) 0.3269(3) 0.78438(19) 0.0328(4) Uani 1 1 d . . . C2 C 0.4582(4) 0.1709(3) 0.7719(2) 0.0360(5) Uani 1 1 d . . . C3 C 0.3977(4) 0.0610(3) 0.6490(3) 0.0396(5) Uani 1 1 d . . . C4 C 0.3186(4) 0.1130(3) 0.5359(3) 0.0383(5) Uani 1 1 d . . . C5 C 0.3052(3) 0.2774(3) 0.5463(2) 0.0294(4) Uani 1 1 d . . . C6 C 0.3719(3) 0.3815(3) 0.6731(2) 0.0308(4) Uani 1 1 d . . . N7 N 0.2204(3) 0.3245(3) 0.4301(2) 0.0344(4) Uani 1 1 d . . . C8 C 0.1896(3) 0.4752(3) 0.4179(2) 0.0304(4) Uani 1 1 d . . . O9 O 0.2531(3) 0.6045(2) 0.50375(19) 0.0401(4) Uani 1 1 d . . . C10 C 0.0590(3) 0.4699(3) 0.2897(2) 0.0293(4) Uani 1 1 d . . . C11 C -0.0819(4) 0.3138(3) 0.2233(3) 0.0367(5) Uani 1 1 d . . . C12 C -0.2181(4) 0.3226(3) 0.1244(3) 0.0377(5) Uani 1 1 d . . . N13 N -0.2190(3) 0.4754(3) 0.0848(2) 0.0334(4) Uani 1 1 d . . . C14 C -0.0739(3) 0.6252(3) 0.1415(3) 0.0362(5) Uani 1 1 d . . . C15 C 0.0642(3) 0.6276(3) 0.2446(3) 0.0338(4) Uani 1 1 d . . . O16 O 0.3232(4) 0.2933(3) 1.1341(2) 0.0548(5) Uani 1 1 d . . . N17 N 0.2628(3) 0.1280(3) 1.1211(2) 0.0362(4) Uani 1 1 d . . . O18 O 0.1652(4) 0.0486(3) 1.2031(2) 0.0556(6) Uani 1 1 d . . . O19 O 0.3064(6) 0.0524(4) 1.0323(4) 0.0992(13) Uani 1 1 d . . . H2 H 0.505(5) 0.141(4) 0.851(4) 0.039(8) Uiso 1 1 d . . . H3 H 0.418(5) -0.039(5) 0.647(4) 0.044(9) Uiso 1 1 d . . . H4 H 0.284(4) 0.047(4) 0.446(3) 0.037(8) Uiso 1 1 d . . . H6 H 0.370(4) 0.498(4) 0.678(3) 0.040(8) Uiso 1 1 d . . . H7 H 0.202(5) 0.264(5) 0.361(4) 0.043(9) Uiso 1 1 d . . . H11 H -0.090(5) 0.208(5) 0.245(4) 0.045(9) Uiso 1 1 d . . . H12 H -0.314(5) 0.224(5) 0.086(4) 0.044(8) Uiso 1 1 d . . . H14 H -0.075(4) 0.734(4) 0.117(3) 0.037(7) Uiso 1 1 d . . . H15 H 0.162(6) 0.725(5) 0.289(4) 0.055(10) Uiso 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 0.03312(15) 0.03143(14) 0.02113(14) 0.00022(8) -0.00016(9) 0.01487(10) N1 0.0401(10) 0.0338(9) 0.0240(9) -0.0003(7) 0.0012(8) 0.0160(8) C2 0.0443(13) 0.0398(12) 0.0281(11) 0.0058(9) 0.0042(9) 0.0217(10) C3 0.0536(14) 0.0355(11) 0.0359(12) 0.0018(9) 0.0083(11) 0.0247(11) C4 0.0506(14) 0.0362(11) 0.0289(11) -0.0042(9) 0.0027(10) 0.0207(10) C5 0.0321(10) 0.0341(10) 0.0230(10) 0.0003(8) 0.0041(8) 0.0148(8) C6 0.0367(11) 0.0311(10) 0.0247(10) -0.0005(8) 0.0029(8) 0.0148(8) N7 0.0452(11) 0.0386(10) 0.0212(9) -0.0047(7) -0.0009(8) 0.0220(9) C8 0.0310(10) 0.0352(10) 0.0249(10) 0.0024(8) 0.0040(8) 0.0136(8) O9 0.0490(10) 0.0354(8) 0.0315(8) -0.0047(7) -0.0053(7) 0.0172(7) C10 0.0297(10) 0.0349(10) 0.0243(9) 0.0008(8) 0.0041(8) 0.0146(8) C11 0.0405(12) 0.0296(11) 0.0376(12) -0.0016(9) -0.0025(10) 0.0150(9) C12 0.0388(12) 0.0325(11) 0.0378(12) -0.0061(9) -0.0051(10) 0.0153(10) N13 0.0362(10) 0.0368(10) 0.0285(9) 0.0002(7) 0.0004(8) 0.0181(8) C14 0.0365(11) 0.0341(11) 0.0376(12) 0.0087(9) 0.0042(10) 0.0139(9) C15 0.0303(10) 0.0319(10) 0.0345(11) 0.0027(9) 0.0025(9) 0.0084(9) O16 0.0782(15) 0.0330(9) 0.0480(11) 0.0056(8) 0.0218(11) 0.0125(9) N17 0.0501(12) 0.0335(9) 0.0283(9) 0.0022(7) 0.0057(8) 0.0205(9) O18 0.0809(16) 0.0345(9) 0.0425(11) 0.0075(8) 0.0200(11) 0.0095(10) O19 0.164(4) 0.0653(17) 0.086(2) -0.0041(15) 0.069(2) 0.050(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 N13 2.343(2) 1_656 ? Cd1 N13 2.343(2) 2_566 ? Cd1 O16 2.356(2) 2_667 ? Cd1 O16 2.356(2) . ? Cd1 N1 2.3844(19) . ? Cd1 N1 2.3844(19) 2_667 ? N1 C2 1.335(3) . ? N1 C6 1.344(3) . ? C2 C3 1.382(3) . ? C2 H2 0.91(4) . ? C3 C4 1.373(4) . ? C3 H3 0.90(4) . ? C4 C5 1.397(3) . ? C4 H4 0.97(3) . ? C5 C6 1.391(3) . ? C5 N7 1.397(3) . ? C6 H6 0.96(3) . ? N7 C8 1.361(3) . ? N7 H7 0.78(4) . ? C8 O9 1.215(3) . ? C8 C10 1.504(3) . ? C10 C15 1.384(3) . ? C10 C11 1.387(3) . ? C11 C12 1.374(4) . ? C11 H11 0.89(4) . ? C12 N13 1.341(3) . ? C12 H12 0.89(4) . ? N13 C14 1.344(3) . ? N13 Cd1 2.343(2) 1_454 ? C14 C15 1.377(3) . ? C14 H14 0.95(3) . ? C15 H15 0.91(4) . ? O16 N17 1.249(3) . ? N17 O19 1.210(3) . ? N17 O18 1.236(3) . ? 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 N13 Cd1 N13 179.999(1) 1_656 2_566 ? N13 Cd1 O16 85.41(8) 1_656 2_667 ? N13 Cd1 O16 94.59(8) 2_566 2_667 ? N13 Cd1 O16 94.59(8) 1_656 . ? N13 Cd1 O16 85.41(8) 2_566 . ? O16 Cd1 O16 180.0 2_667 . ? N13 Cd1 N1 95.76(7) 1_656 . ? N13 Cd1 N1 84.24(7) 2_566 . ? O16 Cd1 N1 76.99(7) 2_667 . ? O16 Cd1 N1 103.01(7) . . ? N13 Cd1 N1 84.24(7) 1_656 2_667 ? N13 Cd1 N1 95.76(7) 2_566 2_667 ? O16 Cd1 N1 103.01(7) 2_667 2_667 ? O16 Cd1 N1 76.99(7) . 2_667 ? N1 Cd1 N1 180.00(11) . 2_667 ? C2 N1 C6 119.1(2) . . ? C2 N1 Cd1 123.31(16) . . ? C6 N1 Cd1 117.08(15) . . ? N1 C2 C3 122.1(2) . . ? N1 C2 H2 115(2) . . ? C3 C2 H2 123(2) . . ? C4 C3 C2 119.2(2) . . ? C4 C3 H3 123(2) . . ? C2 C3 H3 117(2) . . ? C3 C4 C5 119.6(2) . . ? C3 C4 H4 122.8(19) . . ? C5 C4 H4 117.2(19) . . ? C6 C5 C4 117.8(2) . . ? C6 C5 N7 124.1(2) . . ? C4 C5 N7 118.0(2) . . ? N1 C6 C5 122.2(2) . . ? N1 C6 H6 120(2) . . ? C5 C6 H6 118(2) . . ? C8 N7 C5 127.9(2) . . ? C8 N7 H7 115(3) . . ? C5 N7 H7 116(3) . . ? O9 C8 N7 124.8(2) . . ? O9 C8 C10 120.3(2) . . ? N7 C8 C10 114.88(19) . . ? C15 C10 C11 117.9(2) . . ? C15 C10 C8 119.2(2) . . ? C11 C10 C8 122.5(2) . . ? C12 C11 C10 119.0(2) . . ? C12 C11 H11 119(2) . . ? C10 C11 H11 122(2) . . ? N13 C12 C11 123.3(2) . . ? N13 C12 H12 117(2) . . ? C11 C12 H12 119(2) . . ? C12 N13 C14 117.3(2) . . ? C12 N13 Cd1 120.79(17) . 1_454 ? C14 N13 Cd1 117.12(16) . 1_454 ? N13 C14 C15 122.7(2) . . ? N13 C14 H14 117.9(19) . . ? C15 C14 H14 119(2) . . ? C14 C15 C10 119.5(2) . . ? C14 C15 H15 126(2) . . ? C10 C15 H15 114(2) . . ? N17 O16 Cd1 130.83(17) . . ? O19 N17 O18 122.5(3) . . ? O19 N17 O16 119.2(3) . . ? O18 N17 O16 118.2(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7 O16 0.78(4) 2.55(4) 3.168(3) 137(3) 1_554 N7 H7 O18 0.78(4) 2.20(4) 2.965(3) 165(3) 1_554 C4 H4 O18 0.97(3) 2.45(3) 3.284(3) 144(3) 1_554 C12 H12 O19 0.89(4) 2.52(4) 3.153(4) 128(3) 2_556 C14 H14 O18 0.95(3) 2.56(3) 3.237(3) 128(2) 1_564 _diffrn_measured_fraction_theta_max 0.874 _diffrn_reflns_theta_full 28.22 _diffrn_measured_fraction_theta_full 0.874 _refine_diff_density_max 0.837 _refine_diff_density_min -1.309 _refine_diff_density_rms 0.104 # Attachment '4_kb540c1m_FINAL.cif' data_kb540c1m _database_code_depnum_ccdc_archive 'CCDC 635726' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 Cd N8 O8' _chemical_formula_weight 634.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.2806(10) _cell_length_b 22.399(2) _cell_length_c 15.2443(11) _cell_angle_alpha 90.00 _cell_angle_beta 124.862(4) _cell_angle_gamma 90.00 _cell_volume 2880.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 0.814 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7923 _exptl_absorpt_correction_T_max 0.9682 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17290 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 28.27 _reflns_number_total 6754 _reflns_number_gt 5811 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0308P)^2^+40.5415P] 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 6754 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0982 _refine_ls_R_factor_gt 0.0871 _refine_ls_wR_factor_ref 0.1996 _refine_ls_wR_factor_gt 0.1957 _refine_ls_goodness_of_fit_ref 1.289 _refine_ls_restrained_S_all 1.289 _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 0.57747(6) 0.19124(2) -0.04825(4) 0.01237(15) Uani 1 1 d . . . N1 N 1.3184(7) 0.1768(3) 0.7918(5) 0.0130(12) Uani 1 1 d . . . C2 C 1.2024(9) 0.1582(4) 0.8020(6) 0.0186(16) Uani 1 1 d . . . H2 H 1.2279 0.1532 0.8720 0.022 Uiso 1 1 calc R . . C3 C 1.0498(9) 0.1461(4) 0.7168(6) 0.0229(17) Uani 1 1 d . . . H3 H 0.9714 0.1338 0.7275 0.028 Uiso 1 1 calc R . . C4 C 1.0140(9) 0.1526(3) 0.6147(6) 0.0179(15) Uani 1 1 d . . . H4 H 0.9100 0.1444 0.5539 0.021 Uiso 1 1 calc R . . C5 C 1.1292(9) 0.1709(3) 0.6019(6) 0.0149(14) Uani 1 1 d . . . C6 C 1.2805(9) 0.1828(3) 0.6933(6) 0.0161(14) Uani 1 1 d . . . H6A H 1.3602 0.1958 0.6844 0.019 Uiso 1 1 calc R . . N7 N 1.1096(7) 0.1795(3) 0.5030(5) 0.0147(12) Uani 1 1 d . . . H7 H 1.1881 0.1967 0.5047 0.018 Uiso 1 1 calc R . . C8 C 0.9787(8) 0.1633(3) 0.4045(5) 0.0125(13) Uani 1 1 d . . . O9 O 0.8602(6) 0.1409(3) 0.3917(4) 0.0207(12) Uani 1 1 d . . . C10 C 0.9885(8) 0.1741(3) 0.3112(5) 0.0104(13) Uani 1 1 d . . . C11 C 0.8429(9) 0.1802(3) 0.2124(6) 0.0138(14) Uani 1 1 d . . . H11 H 0.7483 0.1770 0.2094 0.017 Uiso 1 1 calc R . . N12 N 0.8317(7) 0.1903(3) 0.1220(5) 0.0158(12) Uani 1 1 d . . . C13 C 0.9669(9) 0.1941(4) 0.1280(6) 0.0174(14) Uani 1 1 d . . . H13 H 0.9598 0.2013 0.0640 0.021 Uiso 1 1 calc R . . C14 C 1.1159(10) 0.1880(4) 0.2222(7) 0.0261(18) Uani 1 1 d . . . H14 H 1.2090 0.1911 0.2234 0.031 Uiso 1 1 calc R . . C15 C 1.1243(9) 0.1772(3) 0.3144(6) 0.0162(15) Uani 1 1 d . . . H15 H 1.2246 0.1718 0.3803 0.019 Uiso 1 1 calc R . . N16 N 0.4233(8) -0.2056(3) -0.4549(5) 0.0139(12) Uani 1 1 d . . . C17 C 0.3884(9) -0.1788(3) -0.5453(6) 0.0151(15) Uani 1 1 d . . . H17 H 0.3541 -0.2024 -0.6067 0.018 Uiso 1 1 calc R . . C18 C 0.4017(10) -0.1178(3) -0.5502(6) 0.0203(16) Uani 1 1 d . . . H18 H 0.3759 -0.0992 -0.6143 0.024 Uiso 1 1 calc R . . C19 C 0.4537(12) -0.0840(4) -0.4593(8) 0.027(2) Uani 1 1 d . . . H19A H 0.4739 -0.0426 -0.4589 0.033 Uiso 1 1 calc R . . C20 C 0.4764(10) -0.1104(4) -0.3687(6) 0.0200(16) Uani 1 1 d . . . C21 C 0.4644(9) -0.1718(3) -0.3708(6) 0.0154(14) Uani 1 1 d . . . H21 H 0.4868 -0.1912 -0.3082 0.018 Uiso 1 1 calc R . . N22 N 0.5200(10) -0.0808(3) -0.2746(5) 0.0258(16) Uani 1 1 d . . . H22 H 0.5392 -0.1031 -0.2209 0.031 Uiso 1 1 calc R . . C23 C 0.5354(14) -0.0208(4) -0.2585(7) 0.034(2) Uani 1 1 d . . . O24 O 0.5139(12) 0.0158(3) -0.3250(6) 0.050(2) Uani 1 1 d . . . C25 C 0.5881(13) -0.0004(4) -0.1488(7) 0.032(2) Uani 1 1 d . . . C26 C 0.5645(11) 0.0597(4) -0.1401(7) 0.0240(18) Uani 1 1 d . . . H26 H 0.5179 0.0838 -0.2024 0.029 Uiso 1 1 calc R . . N27 N 0.6039(8) 0.0856(3) -0.0486(5) 0.0163(13) Uani 1 1 d . . . C28 C 0.6673(11) 0.0506(3) 0.0392(6) 0.0238(18) Uani 1 1 d . . . H28 H 0.6934 0.0681 0.1042 0.029 Uiso 1 1 calc R . . C29 C 0.6951(13) -0.0092(4) 0.0375(8) 0.032(2) Uani 1 1 d . . . H29 H 0.7446 -0.0323 0.1011 0.039 Uiso 1 1 calc R . . C30 C 0.6494(15) -0.0353(4) -0.0592(8) 0.038(3) Uani 1 1 d . . . H30 H 0.6606 -0.0772 -0.0632 0.046 Uiso 1 1 calc R . . O31 O 0.7358(7) 0.1771(2) -0.1104(4) 0.0223(12) Uani 1 1 d . . . N32 N 0.7322(8) 0.2055(3) -0.1845(5) 0.0166(13) Uani 1 1 d . . . O33 O 0.6142(6) 0.2344(3) -0.2513(4) 0.0206(11) Uani 1 1 d . . . O34 O 0.8497(7) 0.2023(2) -0.1869(5) 0.0251(13) Uani 1 1 d . . . O35 O 0.4850(6) 0.1643(2) 0.0595(4) 0.0148(10) Uani 1 1 d . . . N36 N 0.3876(7) 0.1981(3) 0.0623(5) 0.0123(12) Uani 1 1 d . . . O37 O 0.3462(6) 0.2457(2) 0.0107(4) 0.0177(11) Uani 1 1 d . . . O38 O 0.3341(7) 0.1811(2) 0.1141(4) 0.0190(11) 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 0.0162(3) 0.0097(2) 0.0096(2) 0.0003(2) 0.00645(19) 0.0015(2) N1 0.010(3) 0.012(3) 0.009(3) -0.001(2) 0.001(2) -0.003(2) C2 0.019(4) 0.027(4) 0.014(4) -0.003(3) 0.011(3) -0.012(3) C3 0.012(4) 0.041(5) 0.018(4) -0.006(3) 0.010(3) -0.007(3) C4 0.018(4) 0.020(4) 0.018(4) -0.003(3) 0.012(3) -0.004(3) C5 0.013(3) 0.019(3) 0.017(4) 0.000(3) 0.011(3) 0.002(3) C6 0.020(4) 0.013(3) 0.021(4) 0.004(3) 0.014(3) 0.005(3) N7 0.007(3) 0.024(3) 0.015(3) -0.001(2) 0.007(2) -0.005(2) C8 0.004(3) 0.020(3) 0.009(3) 0.002(3) 0.001(3) 0.003(3) O9 0.004(2) 0.044(3) 0.013(3) 0.000(2) 0.004(2) -0.006(2) C10 0.010(3) 0.010(3) 0.009(3) 0.000(2) 0.004(3) 0.001(2) C11 0.016(3) 0.015(3) 0.012(3) 0.003(3) 0.009(3) 0.004(3) N12 0.022(3) 0.011(3) 0.014(3) -0.003(2) 0.011(3) 0.004(3) C13 0.018(3) 0.023(4) 0.011(3) -0.004(3) 0.008(3) -0.006(3) C14 0.021(4) 0.035(5) 0.022(4) -0.016(4) 0.012(3) -0.016(4) C15 0.011(3) 0.020(4) 0.011(3) -0.004(3) 0.003(3) 0.002(3) N16 0.015(3) 0.014(3) 0.013(3) 0.002(2) 0.008(2) 0.000(2) C17 0.020(4) 0.017(4) 0.020(4) -0.005(3) 0.018(3) 0.000(3) C18 0.031(4) 0.017(4) 0.021(4) 0.003(3) 0.019(4) -0.002(3) C19 0.051(6) 0.012(4) 0.044(5) 0.004(3) 0.042(5) 0.013(4) C20 0.028(4) 0.021(4) 0.018(4) -0.003(3) 0.018(4) -0.001(3) C21 0.018(4) 0.016(3) 0.009(3) 0.000(3) 0.006(3) 0.000(3) N22 0.053(5) 0.013(3) 0.016(3) -0.001(3) 0.023(3) -0.005(3) C23 0.068(7) 0.016(4) 0.025(5) -0.001(3) 0.031(5) -0.004(4) O24 0.119(7) 0.012(3) 0.032(4) -0.002(3) 0.051(5) -0.006(4) C25 0.060(6) 0.016(4) 0.027(5) -0.006(3) 0.029(5) -0.006(4) C26 0.039(5) 0.018(4) 0.025(4) 0.000(3) 0.024(4) -0.005(3) N27 0.021(3) 0.015(3) 0.022(3) -0.001(3) 0.018(3) -0.002(2) C28 0.050(5) 0.013(3) 0.016(4) -0.003(3) 0.023(4) -0.004(3) C29 0.059(6) 0.017(4) 0.033(5) 0.000(4) 0.033(5) -0.002(4) C30 0.082(8) 0.007(4) 0.037(5) -0.001(3) 0.041(6) 0.000(4) O31 0.028(3) 0.024(3) 0.017(3) 0.003(2) 0.014(3) 0.003(2) N32 0.022(3) 0.010(3) 0.012(3) -0.003(2) 0.006(3) -0.005(2) O33 0.014(3) 0.027(3) 0.016(3) 0.005(2) 0.006(2) 0.005(2) O34 0.022(3) 0.014(3) 0.048(4) 0.004(2) 0.025(3) 0.005(2) O35 0.010(2) 0.019(3) 0.013(3) -0.001(2) 0.005(2) 0.006(2) N36 0.012(3) 0.013(3) 0.012(3) -0.005(2) 0.006(2) -0.011(2) O37 0.015(3) 0.017(3) 0.019(3) 0.006(2) 0.009(2) 0.007(2) O38 0.027(3) 0.016(3) 0.020(3) -0.002(2) 0.016(2) -0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 N16 2.311(6) 2_654 ? Cd1 O31 2.326(6) . ? Cd1 N27 2.382(6) . ? Cd1 N1 2.391(6) 1_454 ? Cd1 O35 2.397(5) . ? Cd1 N12 2.411(6) . ? N1 C6 1.324(9) . ? N1 C2 1.353(9) . ? N1 Cd1 2.391(6) 1_656 ? C2 C3 1.376(11) . ? C2 H2 0.9500 . ? C3 C4 1.388(11) . ? C3 H3 0.9500 . ? C4 C5 1.368(10) . ? C4 H4 0.9500 . ? C5 C6 1.398(11) . ? C5 N7 1.416(9) . ? C6 H6A 0.9500 . ? N7 C8 1.373(9) . ? N7 H7 0.8800 . ? C8 O9 1.225(8) . ? C8 C10 1.502(9) . ? C10 C15 1.372(10) . ? C10 C11 1.396(10) . ? C11 N12 1.336(9) . ? C11 H11 0.9500 . ? N12 C13 1.342(9) . ? C13 C14 1.383(11) . ? C13 H13 0.9500 . ? C14 C15 1.379(11) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? N16 C21 1.334(9) . ? N16 C17 1.350(9) . ? N16 Cd1 2.311(6) 2_644 ? C17 C18 1.381(10) . ? C17 H17 0.9500 . ? C18 C19 1.390(11) . ? C18 H18 0.9500 . ? C19 C20 1.393(11) . ? C19 H19A 0.9500 . ? C20 C21 1.379(10) . ? C20 N22 1.401(10) . ? C21 H21 0.9500 . ? N22 C23 1.360(10) . ? N22 H22 0.8800 . ? C23 O24 1.221(10) . ? C23 C25 1.503(12) . ? C25 C30 1.375(12) . ? C25 C26 1.388(11) . ? C26 N27 1.342(10) . ? C26 H26 0.9500 . ? N27 C28 1.354(10) . ? C28 C29 1.374(11) . ? C28 H28 0.9500 . ? C29 C30 1.395(12) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? O31 N32 1.280(8) . ? N32 O33 1.230(8) . ? N32 O34 1.232(8) . ? O35 N36 1.275(8) . ? N36 O37 1.247(8) . ? N36 O38 1.252(8) . ? 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 N16 Cd1 O31 99.0(2) 2_654 . ? N16 Cd1 N27 174.2(2) 2_654 . ? O31 Cd1 N27 75.89(19) . . ? N16 Cd1 N1 98.2(2) 2_654 1_454 ? O31 Cd1 N1 101.4(2) . 1_454 ? N27 Cd1 N1 85.7(2) . 1_454 ? N16 Cd1 O35 103.3(2) 2_654 . ? O31 Cd1 O35 152.66(18) . . ? N27 Cd1 O35 80.90(18) . . ? N1 Cd1 O35 91.02(19) 1_454 . ? N16 Cd1 N12 90.0(2) 2_654 . ? O31 Cd1 N12 81.8(2) . . ? N27 Cd1 N12 86.5(2) . . ? N1 Cd1 N12 170.6(2) 1_454 . ? O35 Cd1 N12 82.59(19) . . ? C6 N1 C2 116.9(6) . . ? C6 N1 Cd1 125.2(5) . 1_656 ? C2 N1 Cd1 117.8(5) . 1_656 ? N1 C2 C3 123.9(7) . . ? N1 C2 H2 118.1 . . ? C3 C2 H2 118.1 . . ? C2 C3 C4 117.8(7) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? C5 C4 C3 119.7(7) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 118.4(7) . . ? C4 C5 N7 125.8(7) . . ? C6 C5 N7 115.9(6) . . ? N1 C6 C5 123.4(7) . . ? N1 C6 H6A 118.3 . . ? C5 C6 H6A 118.3 . . ? C8 N7 C5 125.6(6) . . ? C8 N7 H7 117.2 . . ? C5 N7 H7 117.2 . . ? O9 C8 N7 123.2(6) . . ? O9 C8 C10 120.9(6) . . ? N7 C8 C10 116.0(6) . . ? C15 C10 C11 118.4(6) . . ? C15 C10 C8 126.4(6) . . ? C11 C10 C8 115.3(6) . . ? N12 C11 C10 122.5(7) . . ? N12 C11 H11 118.8 . . ? C10 C11 H11 118.8 . . ? C11 N12 C13 117.7(6) . . ? C11 N12 Cd1 120.9(5) . . ? C13 N12 Cd1 121.1(5) . . ? N12 C13 C14 123.6(7) . . ? N12 C13 H13 118.2 . . ? C14 C13 H13 118.2 . . ? C15 C14 C13 117.6(7) . . ? C15 C14 H14 121.2 . . ? C13 C14 H14 121.2 . . ? C10 C15 C14 120.2(7) . . ? C10 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C21 N16 C17 118.8(6) . . ? C21 N16 Cd1 123.4(5) . 2_644 ? C17 N16 Cd1 117.6(5) . 2_644 ? N16 C17 C18 121.2(7) . . ? N16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C17 C18 C19 118.6(7) . . ? C17 C18 H18 120.7 . . ? C19 C18 H18 120.7 . . ? C18 C19 C20 120.5(7) . . ? C18 C19 H19A 119.7 . . ? C20 C19 H19A 119.7 . . ? C21 C20 C19 116.0(7) . . ? C21 C20 N22 117.8(7) . . ? C19 C20 N22 126.0(7) . . ? N16 C21 C20 124.3(7) . . ? N16 C21 H21 117.8 . . ? C20 C21 H21 117.8 . . ? C23 N22 C20 126.1(7) . . ? C23 N22 H22 116.9 . . ? C20 N22 H22 116.9 . . ? O24 C23 N22 124.4(8) . . ? O24 C23 C25 120.0(8) . . ? N22 C23 C25 115.6(7) . . ? C30 C25 C26 117.6(8) . . ? C30 C25 C23 127.0(8) . . ? C26 C25 C23 115.4(8) . . ? N27 C26 C25 123.6(8) . . ? N27 C26 H26 118.2 . . ? C25 C26 H26 118.2 . . ? C26 N27 C28 117.8(7) . . ? C26 N27 Cd1 117.7(5) . . ? C28 N27 Cd1 124.3(5) . . ? N27 C28 C29 122.2(7) . . ? N27 C28 H28 118.9 . . ? C29 C28 H28 118.9 . . ? C28 C29 C30 118.8(8) . . ? C28 C29 H29 120.6 . . ? C30 C29 H29 120.6 . . ? C25 C30 C29 119.8(8) . . ? C25 C30 H30 120.1 . . ? C29 C30 H30 120.1 . . ? N32 O31 Cd1 128.2(5) . . ? O33 N32 O34 121.7(6) . . ? O33 N32 O31 120.7(6) . . ? O34 N32 O31 117.6(6) . . ? N36 O35 Cd1 120.0(4) . . ? O37 N36 O38 122.9(6) . . ? O37 N36 O35 118.5(6) . . ? O38 N36 O35 118.5(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7 O37 0.88 2.04 2.900(8) 166.5 4_666 N22 H22 O38 0.88 2.23 3.016(9) 148.4 3_655 C15 H15 O37 0.95 2.47 3.056(9) 120.1 4_666 C17 H17 O33 0.95 2.47 3.326(9) 149.7 3_654 C17 H17 O34 0.95 2.60 3.392(10) 141.3 3_654 C21 H21 O38 0.95 2.44 3.221(9) 139.2 3_655 C30 H30 O35 0.95 2.48 3.202(10) 132.7 3_655 C30 H30 O38 0.95 2.47 3.400(10) 167.6 3_655 _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.983 _refine_diff_density_min -2.854 _refine_diff_density_rms 0.186 # Attachment '5_kkb538em_FINAL.cif' data_kkb538em _database_code_depnum_ccdc_archive 'CCDC 635727' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H9 Cl2 N3 O Zn' _chemical_formula_weight 335.48 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/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 8.738(4) _cell_length_b 9.491(4) _cell_length_c 15.969(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.922(7) _cell_angle_gamma 90.00 _cell_volume 1322.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PRISMATIC _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.685 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 2.250 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6618 _exptl_absorpt_correction_T_max 0.9356 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14652 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3173 _reflns_number_gt 2649 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4.1' _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^)+(0.0517P)^2^+1.0860P] 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 3173 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0884 _refine_ls_wR_factor_gt 0.0830 _refine_ls_goodness_of_fit_ref 0.894 _refine_ls_restrained_S_all 0.894 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.86640(3) 1.15358(3) 0.300724(16) 0.02541(10) Uani 1 1 d . . . N1 N 0.8569(2) 1.16410(19) 0.17351(12) 0.0242(4) Uani 1 1 d . . . C2 C 0.9207(3) 1.2717(2) 0.13257(15) 0.0273(5) Uani 1 1 d . . . C3 C 0.9222(3) 1.2735(3) 0.04615(15) 0.0292(5) Uani 1 1 d . . . C4 C 0.8574(3) 1.1642(2) -0.00088(15) 0.0279(5) Uani 1 1 d . . . C5 C 0.7884(3) 1.0544(2) 0.04171(14) 0.0241(4) Uani 1 1 d . . . C6 C 0.7929(3) 1.0586(2) 0.12898(14) 0.0251(5) Uani 1 1 d . . . N7 N 0.7108(3) 0.9405(2) 0.00258(12) 0.0277(4) Uani 1 1 d . . . C8 C 0.7296(3) 0.8934(2) -0.07699(14) 0.0241(5) Uani 1 1 d . . . O9 O 0.8186(2) 0.94701(18) -0.12388(10) 0.0308(4) Uani 1 1 d . . . C10 C 0.6326(3) 0.7692(2) -0.10521(13) 0.0249(5) Uani 1 1 d . . . C11 C 0.6609(3) 0.7100(3) -0.18225(16) 0.0370(6) Uani 1 1 d . . . C12 C 0.5791(3) 0.5937(3) -0.21029(17) 0.0396(6) Uani 1 1 d . . . N13 N 0.4694(2) 0.5344(2) -0.16583(12) 0.0276(4) Uani 1 1 d . . . C14 C 0.4388(3) 0.5936(3) -0.09226(15) 0.0283(5) Uani 1 1 d . . . C15 C 0.5175(3) 0.7090(3) -0.05986(14) 0.0277(5) Uani 1 1 d . . . Cl16 Cl 0.64113(8) 1.15928(7) 0.35873(5) 0.04200(18) Uani 1 1 d . . . Cl17 Cl 1.02778(7) 1.32507(6) 0.34569(4) 0.03212(15) Uani 1 1 d . . . H2 H 0.965(3) 1.343(3) 0.1667(18) 0.035(8) Uiso 1 1 d . . . H3 H 0.965(3) 1.345(3) 0.0177(17) 0.024(7) Uiso 1 1 d . . . H4 H 0.854(3) 1.162(2) -0.0581(18) 0.024(7) Uiso 1 1 d . . . H6 H 0.750(3) 0.989(3) 0.1572(15) 0.021(6) Uiso 1 1 d . . . H7 H 0.660(3) 0.896(3) 0.0302(18) 0.030(7) Uiso 1 1 d . . . H11 H 0.739(3) 0.751(3) -0.2139(18) 0.039(8) Uiso 1 1 d . . . H12 H 0.595(3) 0.548(3) -0.261(2) 0.046(8) Uiso 1 1 d . . . H14 H 0.370(3) 0.551(3) -0.0621(18) 0.035(7) Uiso 1 1 d . . . H15 H 0.491(3) 0.747(3) -0.0049(18) 0.037(7) Uiso 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 Zn1 0.03337(17) 0.02387(16) 0.01891(15) -0.00031(10) 0.00066(11) -0.00038(10) N1 0.0295(10) 0.0243(9) 0.0187(9) 0.0000(7) 0.0002(7) 0.0014(7) C2 0.0327(12) 0.0238(11) 0.0251(11) -0.0013(9) 0.0000(10) -0.0018(9) C3 0.0367(13) 0.0253(12) 0.0257(12) 0.0048(9) 0.0041(10) -0.0048(10) C4 0.0362(13) 0.0291(12) 0.0186(11) 0.0033(9) 0.0031(9) 0.0010(10) C5 0.0284(11) 0.0235(10) 0.0202(10) 0.0015(8) -0.0005(9) -0.0009(9) C6 0.0309(12) 0.0226(11) 0.0218(11) 0.0020(9) 0.0021(9) -0.0025(9) N7 0.0378(11) 0.0272(10) 0.0185(9) 0.0012(8) 0.0042(8) -0.0086(9) C8 0.0290(12) 0.0232(10) 0.0199(10) 0.0010(8) 0.0002(9) 0.0049(9) O9 0.0361(9) 0.0318(9) 0.0252(8) -0.0015(7) 0.0081(7) -0.0027(7) C10 0.0299(12) 0.0266(11) 0.0183(10) -0.0009(9) 0.0017(9) 0.0031(9) C11 0.0458(15) 0.0424(15) 0.0238(12) -0.0069(11) 0.0123(11) -0.0126(12) C12 0.0525(17) 0.0425(15) 0.0252(13) -0.0118(11) 0.0149(12) -0.0106(13) N13 0.0333(11) 0.0269(10) 0.0226(9) -0.0044(8) 0.0025(8) -0.0011(8) C14 0.0328(12) 0.0303(12) 0.0223(11) 0.0000(9) 0.0059(10) -0.0019(10) C15 0.0330(12) 0.0303(12) 0.0201(11) -0.0060(9) 0.0041(9) -0.0013(10) Cl16 0.0401(4) 0.0406(4) 0.0466(4) -0.0013(3) 0.0152(3) 0.0007(3) Cl17 0.0373(3) 0.0341(3) 0.0250(3) -0.0049(2) 0.0014(2) -0.0075(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 Zn1 N1 2.031(2) . ? Zn1 N13 2.056(2) 4_676 ? Zn1 Cl16 2.2186(11) . ? Zn1 Cl17 2.2472(9) . ? N1 C6 1.334(3) . ? N1 C2 1.348(3) . ? C2 C3 1.381(3) . ? C2 H2 0.94(3) . ? C3 C4 1.384(3) . ? C3 H3 0.91(3) . ? C4 C5 1.398(3) . ? C4 H4 0.91(3) . ? C5 C6 1.393(3) . ? C5 N7 1.405(3) . ? C6 H6 0.89(3) . ? N7 C8 1.365(3) . ? N7 H7 0.77(3) . ? C8 O9 1.218(3) . ? C8 C10 1.507(3) . ? C10 C11 1.386(3) . ? C10 C15 1.392(3) . ? C11 C12 1.378(4) . ? C11 H11 0.95(3) . ? C12 N13 1.345(3) . ? C12 H12 0.93(3) . ? N13 C14 1.342(3) . ? N13 Zn1 2.056(2) 4_575 ? C14 C15 1.380(3) . ? C14 H14 0.89(3) . ? C15 H15 0.99(3) . ? 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 Zn1 N13 107.30(8) . 4_676 ? N1 Zn1 Cl16 115.12(6) . . ? N13 Zn1 Cl16 107.39(6) 4_676 . ? N1 Zn1 Cl17 106.07(6) . . ? N13 Zn1 Cl17 106.61(7) 4_676 . ? Cl16 Zn1 Cl17 113.87(3) . . ? C6 N1 C2 118.8(2) . . ? C6 N1 Zn1 119.38(15) . . ? C2 N1 Zn1 121.70(15) . . ? N1 C2 C3 121.3(2) . . ? N1 C2 H2 115.7(18) . . ? C3 C2 H2 123.0(18) . . ? C2 C3 C4 120.6(2) . . ? C2 C3 H3 122.3(17) . . ? C4 C3 H3 117.1(17) . . ? C3 C4 C5 118.0(2) . . ? C3 C4 H4 123.4(16) . . ? C5 C4 H4 118.6(16) . . ? C6 C5 C4 118.3(2) . . ? C6 C5 N7 117.1(2) . . ? C4 C5 N7 124.6(2) . . ? N1 C6 C5 123.0(2) . . ? N1 C6 H6 117.4(16) . . ? C5 C6 H6 119.6(16) . . ? C8 N7 C5 126.0(2) . . ? C8 N7 H7 117(2) . . ? C5 N7 H7 117(2) . . ? O9 C8 N7 123.1(2) . . ? O9 C8 C10 120.6(2) . . ? N7 C8 C10 116.27(19) . . ? C11 C10 C15 117.5(2) . . ? C11 C10 C8 117.3(2) . . ? C15 C10 C8 125.1(2) . . ? C12 C11 C10 120.0(2) . . ? C12 C11 H11 122.0(18) . . ? C10 C11 H11 118.0(18) . . ? N13 C12 C11 122.4(2) . . ? N13 C12 H12 114.0(19) . . ? C11 C12 H12 123.6(19) . . ? C14 N13 C12 117.8(2) . . ? C14 N13 Zn1 119.12(16) . 4_575 ? C12 N13 Zn1 122.73(16) . 4_575 ? N13 C14 C15 122.9(2) . . ? N13 C14 H14 117.2(18) . . ? C15 C14 H14 119.7(18) . . ? C14 C15 C10 119.4(2) . . ? C14 C15 H15 119.5(17) . . ? C10 C15 H15 121.2(17) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7 Cl17 0.77(3) 2.72(3) 3.455(2) 160(3) 2_645 _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.490 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.092