# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H6 N8 Zn, 0.5(C6 H12 N2 O), 0.5(C2 H6 O)' _chemical_formula_sum 'C8 H15 N9 O Zn' _chemical_formula_weight 318.65 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 orthorhombic _symmetry_space_group_name_H-M Ama2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y, z' '-x+1/2, y, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 15.1635(4) _cell_length_b 17.9739(4) _cell_length_c 10.0176(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2730.27(12) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2540 _cell_measurement_theta_min 2.3830 _cell_measurement_theta_max 27.0425 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1300 _exptl_absorpt_coefficient_mu 1.808 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7138 _exptl_absorpt_correction_T_max 0.7732 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2083 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 10046 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2459 _reflns_number_gt 2236 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0485P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.000(18) _refine_ls_number_reflns 2459 _refine_ls_number_parameters 177 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0918 _refine_ls_wR_factor_gt 0.0890 _refine_ls_goodness_of_fit_ref 1.213 _refine_ls_restrained_S_all 1.213 _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 -0.04841(2) 0.337131(17) 0.83780(6) 0.03661(15) Uani 1 1 d . . . N1 N -0.1788(2) 0.34513(16) 0.8045(3) 0.0396(9) Uani 1 1 d . . . C1 C -0.2500 0.3421(3) 0.8824(6) 0.0416(15) Uani 1 2 d S . . N3 N -0.0118(2) 0.44081(17) 0.8785(3) 0.0371(8) Uani 1 1 d . . . N5 N -0.0003(2) 0.20417(17) 1.1678(3) 0.0360(8) Uani 1 1 d . . . N8 N -0.0295(2) 0.26874(17) 0.9922(4) 0.0360(7) Uani 1 1 d . . . C6 C 0.0959(3) 0.3137(3) 1.1318(6) 0.0609(15) Uani 1 1 d . . . H6A H 0.0999 0.3526 1.0664 0.091 Uiso 1 1 calc R . . H6B H 0.1502 0.2862 1.1334 0.091 Uiso 1 1 calc R . . H6C H 0.0854 0.3351 1.2182 0.091 Uiso 1 1 calc R . . C5 C 0.0221(2) 0.2630(2) 1.0968(4) 0.0341(9) Uani 1 1 d . . . N2 N -0.2071(2) 0.3513(2) 0.6759(4) 0.0521(10) Uani 1 1 d . . . O1 O 0.2500 0.1800(3) -0.1612(10) 0.1055(19) Uani 1 2 d S . . N9 N 0.1737(2) 0.0726(2) -0.1580(6) 0.0699(10) Uani 1 1 d . . . C7 C 0.2500 0.1121(3) -0.1595(10) 0.0642(16) Uani 1 2 d S . . N7 N -0.0863(2) 0.20911(19) 0.9971(4) 0.0456(8) Uani 1 1 d . . . C9 C 0.2500 -0.0429(5) -0.160(3) 0.231(10) Uani 1 2 d S . . H9A H 0.2500 -0.0944 -0.1680 0.277 Uiso 1 2 calc SR . . C8 C 0.1710(4) -0.0066(4) -0.1552(11) 0.110(2) Uani 1 1 d . . . H8A H 0.1180 -0.0324 -0.1500 0.132 Uiso 1 1 calc R . . C10 C 0.0915(4) 0.1132(4) -0.1545(10) 0.117(2) Uani 1 1 d . . . H10A H 0.1035 0.1656 -0.1503 0.176 Uiso 1 1 calc R . . H10B H 0.0583 0.0986 -0.0772 0.176 Uiso 1 1 calc R . . H10C H 0.0580 0.1025 -0.2335 0.176 Uiso 1 1 calc R . . N6 N -0.0686(3) 0.17162(19) 1.1025(5) 0.0468(9) Uani 1 1 d . . . N4 N -0.0070(3) 0.46453(19) 1.0068(4) 0.0677(12) Uani 1 1 d . . . C4 C 0.0000 0.5000 0.6579(9) 0.156(6) Uani 1 2 d S . . H4A H 0.0093 0.5497 0.6259 0.234 Uiso 0.50 1 calc PR . . H4B H -0.0557 0.4819 0.6259 0.234 Uiso 0.50 1 calc PR . . H4C H 0.0464 0.4683 0.6259 0.234 Uiso 0.50 1 calc PR . . C3 C 0.0000 0.5000 0.8047(5) 0.0412(14) Uani 1 2 d S . . C2 C -0.2500 0.3381(5) 1.0282(8) 0.073(3) Uani 1 2 d S . . H2A H -0.3097 0.3374 1.0601 0.109 Uiso 0.50 1 calc PR . . H2B H -0.2200 0.3806 1.0639 0.109 Uiso 0.50 1 calc PR . . H2C H -0.2204 0.2935 1.0562 0.109 Uiso 0.50 1 calc PR . . C11 C 0.2500 0.3712(7) -0.1941(14) 0.123(4) Uiso 1 2 d S . . C12 C 0.2500 0.4465(6) -0.1401(15) 0.129(4) Uiso 1 2 d S . . O2 O 0.1986(8) 0.3222(7) -0.1236(14) 0.146(5) Uiso 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0517(3) 0.0243(2) 0.0339(2) -0.0009(3) -0.0002(3) -0.00121(16) N1 0.0486(18) 0.0371(17) 0.033(3) -0.0008(13) -0.0008(14) -0.0001(13) C1 0.057(4) 0.034(3) 0.034(3) -0.008(2) 0.000 0.000 N3 0.0502(17) 0.0227(15) 0.038(2) -0.0008(12) -0.0010(14) 0.0017(13) N5 0.0381(17) 0.0301(17) 0.0398(19) 0.0011(15) 0.0018(15) -0.0013(14) N8 0.0422(15) 0.0267(16) 0.039(2) -0.0005(15) 0.0010(15) -0.0022(13) C6 0.064(3) 0.046(3) 0.073(4) 0.018(3) -0.019(3) -0.021(2) C5 0.041(2) 0.027(2) 0.034(2) 0.0028(18) 0.000(2) 0.0008(17) N2 0.053(2) 0.069(2) 0.035(2) 0.0148(19) 0.0000(18) 0.0021(19) O1 0.198(6) 0.059(3) 0.059(3) 0.006(5) 0.000 0.000 N9 0.0602(19) 0.086(3) 0.064(3) -0.007(3) 0.005(3) 0.0131(19) C7 0.101(5) 0.059(4) 0.033(3) -0.011(5) 0.000 0.000 N7 0.0519(19) 0.0336(18) 0.051(2) 0.0079(17) -0.0067(19) -0.0046(17) C9 0.091(7) 0.061(5) 0.54(3) 0.038(19) 0.000 0.000 C8 0.078(3) 0.092(4) 0.161(7) -0.002(7) 0.014(7) -0.027(3) C10 0.089(4) 0.167(6) 0.095(5) 0.002(7) 0.004(5) 0.058(4) N6 0.0467(19) 0.040(2) 0.054(3) 0.0090(18) -0.0047(19) -0.0090(16) N4 0.140(4) 0.0240(16) 0.039(2) -0.0012(18) 0.012(3) 0.001(3) C4 0.41(2) 0.026(4) 0.034(5) 0.000 0.000 0.025(9) C3 0.065(3) 0.029(3) 0.030(4) 0.000 0.000 0.000(2) C2 0.065(5) 0.119(8) 0.035(4) -0.002(4) 0.000 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 Zn1 N3 1.987(3) . ? Zn1 N8 1.996(4) . ? Zn1 N5 2.000(3) 6_554 ? Zn1 N1 2.010(4) . ? N1 C1 1.334(5) . ? N1 N2 1.362(5) . ? C1 N1 1.334(5) 4_455 ? C1 C2 1.462(10) . ? N3 C3 1.308(4) . ? N3 N4 1.355(5) . ? N5 C5 1.318(5) . ? N5 N6 1.357(5) . ? N5 Zn1 2.000(3) 6 ? N8 C5 1.312(5) . ? N8 N7 1.376(5) . ? C6 C5 1.486(6) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? N2 N2 1.302(7) 4_455 ? O1 C7 1.221(7) . ? N9 C7 1.358(5) . ? N9 C8 1.424(7) . ? N9 C10 1.445(6) . ? C7 N9 1.358(5) 4 ? N7 N6 1.281(5) . ? C9 C8 1.365(7) 4 ? C9 C8 1.365(7) . ? C9 H9A 0.9300 . ? C8 H8A 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? N4 N4 1.293(7) 2_565 ? C4 C3 1.471(10) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C3 N3 1.308(4) 2_565 ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C11 O2 1.371(14) . ? C11 O2 1.371(14) 4 ? C11 C12 1.457(15) . ? O2 O2 1.56(2) 4 ? 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 N3 Zn1 N8 112.24(13) . . ? N3 Zn1 N5 114.84(13) . 6_554 ? N8 Zn1 N5 112.23(12) . 6_554 ? N3 Zn1 N1 103.97(12) . . ? N8 Zn1 N1 108.28(13) . . ? N5 Zn1 N1 104.39(13) 6_554 . ? C1 N1 N2 107.5(4) . . ? C1 N1 Zn1 134.2(3) . . ? N2 N1 Zn1 118.2(3) . . ? N1 C1 N1 108.2(5) 4_455 . ? N1 C1 C2 125.9(3) 4_455 . ? N1 C1 C2 125.9(3) . . ? C3 N3 N4 105.8(3) . . ? C3 N3 Zn1 133.2(3) . . ? N4 N3 Zn1 120.3(2) . . ? C5 N5 N6 106.4(3) . . ? C5 N5 Zn1 131.4(3) . 6 ? N6 N5 Zn1 122.2(3) . 6 ? C5 N8 N7 106.5(3) . . ? C5 N8 Zn1 138.9(3) . . ? N7 N8 Zn1 114.7(3) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N8 C5 N5 109.9(3) . . ? N8 C5 C6 126.1(4) . . ? N5 C5 C6 124.0(4) . . ? N2 N2 N1 108.4(2) 4_455 . ? C7 N9 C8 123.2(4) . . ? C7 N9 C10 118.1(5) . . ? C8 N9 C10 118.7(5) . . ? O1 C7 N9 121.5(3) . . ? O1 C7 N9 121.5(3) . 4 ? N9 C7 N9 116.9(5) . 4 ? N6 N7 N8 108.0(4) . . ? C8 C9 C8 122.7(9) 4 . ? C8 C9 H9A 118.6 4 . ? C8 C9 H9A 118.6 . . ? C9 C8 N9 116.9(6) . . ? C9 C8 H8A 121.6 . . ? N9 C8 H8A 121.6 . . ? N9 C10 H10A 109.5 . . ? N9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N7 N6 N5 109.3(3) . . ? N4 N4 N3 108.61(19) 2_565 . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C3 N3 111.2(4) 2_565 . ? N3 C3 C4 124.4(2) 2_565 . ? N3 C3 C4 124.4(2) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O2 C11 O2 69.3(12) . 4 ? O2 C11 C12 113.9(11) . . ? O2 C11 C12 113.9(11) 4 . ? C11 O2 O2 55.3(6) . 4 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.730 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 961654' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H6 N8 Zn, (C H4 O)' _chemical_formula_sum 'C5 H10 N8 O Zn' _chemical_formula_weight 263.57 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 orthorhombic _symmetry_space_group_name_H-M Ama2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y, z' '-x+1/2, y, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 15.6799(14) _cell_length_b 18.1616(12) _cell_length_c 9.6615(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2751.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2140 _cell_measurement_theta_min 2.3830 _cell_measurement_theta_max 29.0425 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 940 _exptl_absorpt_coefficient_mu 1.764 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7192 _exptl_absorpt_correction_T_max 0.7778 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.064 0.936 -0.027 1284.8 -14.2 _platon_squeeze_details ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2083 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8178 _diffrn_reflns_av_R_equivalents 0.0735 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2091 _reflns_number_gt 1529 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0870P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.000(18) _refine_ls_number_reflns 2091 _refine_ls_number_parameters 121 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1516 _refine_ls_wR_factor_gt 0.1440 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _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 0.05582(5) 0.15992(3) 0.32759(15) 0.0592(3) Uani 1 1 d . . . N1 N -0.0382(4) 0.2737(3) 0.6595(8) 0.0596(17) Uani 1 1 d . . . N5 N 0.1797(4) 0.1568(3) 0.3629(5) 0.0553(18) Uani 1 1 d . . . N7 N 0.0165(4) 0.0572(3) 0.2918(6) 0.0569(17) Uani 1 1 d . . . N6 N 0.2096(6) 0.1562(4) 0.4947(13) 0.102(3) Uani 1 1 d . . . N4 N 0.0015(4) 0.2070(3) 0.4874(6) 0.0547(16) Uani 1 1 d . . . N3 N -0.0694(7) 0.1799(5) 0.5419(12) 0.100(3) Uani 1 1 d . . . C3 C 0.2500 0.1528(5) 0.2843(9) 0.053(3) Uani 1 2 d S . . C1 C 0.0185(6) 0.2653(4) 0.5658(10) 0.066(2) Uani 1 1 d . . . N2 N -0.0926(6) 0.2162(4) 0.6487(10) 0.094(3) Uani 1 1 d . . . N8 N 0.0117(8) 0.0328(4) 0.1561(9) 0.109(3) Uani 1 1 d . . . C5 C 0.0000 0.0000 0.3638(9) 0.073(4) Uani 1 2 d S . . C4 C 0.2500 0.1477(11) 0.1426(16) 0.144(9) Uani 1 2 d S . . H4A H 0.3077 0.1458 0.1097 0.216 Uiso 0.50 1 calc PR . . H4B H 0.2218 0.1899 0.1041 0.216 Uiso 0.50 1 calc PR . . H4C H 0.2204 0.1038 0.1150 0.216 Uiso 0.50 1 calc PR . . C2 C 0.0889(11) 0.3165(6) 0.5419(18) 0.135(6) Uani 1 1 d . . . H2A H 0.0884 0.3540 0.6119 0.203 Uiso 1 1 calc R . . H2C H 0.0826 0.3389 0.4524 0.203 Uiso 1 1 calc R . . H2B H 0.1420 0.2902 0.5456 0.203 Uiso 1 1 calc R . . C6 C 0.0322(9) -0.0019(9) 0.5196(16) 0.052(4) Uiso 0.50 1 d P . . H6A H 0.0020 -0.0426 0.5662 0.078 Uiso 0.50 1 d PR . . H6B H 0.0933 0.0021 0.5201 0.078 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 0.0623(5) 0.0424(4) 0.0730(6) 0.0003(6) -0.0008(6) 0.0002(3) N1 0.049(4) 0.043(3) 0.087(5) -0.002(3) -0.012(4) -0.002(3) N5 0.051(4) 0.078(4) 0.037(5) 0.007(3) 0.005(3) 0.000(3) N7 0.080(4) 0.035(3) 0.056(5) -0.007(2) 0.006(3) -0.007(2) N6 0.084(7) 0.097(7) 0.126(10) 0.031(5) 0.021(6) -0.004(4) N4 0.064(5) 0.039(3) 0.061(4) -0.004(3) -0.007(4) -0.004(3) N3 0.104(9) 0.079(5) 0.116(8) -0.039(6) 0.015(6) -0.026(5) C3 0.055(8) 0.079(7) 0.025(6) -0.007(4) 0.000 0.000 C1 0.071(6) 0.028(4) 0.098(6) -0.009(4) 0.022(5) -0.009(3) N2 0.097(6) 0.048(4) 0.136(8) -0.021(4) 0.021(6) -0.017(4) N8 0.190(11) 0.051(4) 0.088(6) -0.002(4) 0.015(7) -0.005(6) C5 0.143(13) 0.033(5) 0.044(8) 0.000 0.000 0.006(5) C4 0.23(3) 0.173(18) 0.024(8) -0.040(9) 0.000 0.000 C2 0.142(11) 0.067(7) 0.198(17) -0.027(9) 0.039(12) -0.060(7) _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 N4 1.960(6) . ? Zn1 N5 1.972(6) . ? Zn1 N7 1.995(5) . ? Zn1 N1 2.042(7) 6_554 ? N1 C1 1.278(11) . ? N1 N2 1.351(10) . ? N1 Zn1 2.042(7) 6 ? N5 C3 1.341(8) . ? N5 N6 1.357(14) . ? N7 C5 1.277(7) . ? N7 N8 1.386(10) . ? N6 N6 1.267(19) 4 ? N4 N3 1.324(12) . ? N4 C1 1.328(9) . ? N3 N2 1.277(12) . ? C3 N5 1.341(8) 4 ? C3 C4 1.372(19) . ? C1 C2 1.462(14) . ? N8 N8 1.247(15) 2 ? C5 N7 1.277(7) 2 ? C5 C6 1.589(18) 2 ? C5 C6 1.589(18) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2C 0.9600 . ? C2 H2B 0.9600 . ? C6 C6 1.01(3) 2 ? C6 H6A 0.9863 . ? C6 H6B 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 N4 Zn1 N5 107.7(3) . . ? N4 Zn1 N7 114.2(3) . . ? N5 Zn1 N7 107.9(2) . . ? N4 Zn1 N1 108.1(2) . 6_554 ? N5 Zn1 N1 106.7(2) . 6_554 ? N7 Zn1 N1 111.9(3) . 6_554 ? C1 N1 N2 107.0(7) . . ? C1 N1 Zn1 136.7(6) . 6 ? N2 N1 Zn1 115.6(6) . 6 ? C3 N5 N6 104.3(7) . . ? C3 N5 Zn1 135.5(5) . . ? N6 N5 Zn1 120.2(5) . . ? C5 N7 N8 104.1(6) . . ? C5 N7 Zn1 136.8(5) . . ? N8 N7 Zn1 118.7(5) . . ? N6 N6 N5 110.2(5) 4 . ? N3 N4 C1 103.7(7) . . ? N3 N4 Zn1 121.1(5) . . ? C1 N4 Zn1 135.2(6) . . ? N2 N3 N4 111.6(8) . . ? N5 C3 N5 110.7(8) 4 . ? N5 C3 C4 124.6(4) 4 . ? N5 C3 C4 124.6(4) . . ? N1 C1 N4 111.1(6) . . ? N1 C1 C2 124.2(9) . . ? N4 C1 C2 124.6(10) . . ? N3 N2 N1 106.3(8) . . ? N8 N8 N7 108.8(4) 2 . ? N7 C5 N7 114.0(8) 2 . ? N7 C5 C6 118.0(7) 2 2 ? N7 C5 C6 124.3(7) . 2 ? N7 C5 C6 124.3(7) 2 . ? N7 C5 C6 118.0(7) . . ? C6 C5 C6 37.2(11) 2 . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? H2C C2 H2B 109.5 . . ? C6 C6 C5 71.4(5) 2 . ? C6 C6 H6A 64.6 2 . ? C5 C6 H6A 107.2 . . ? C6 C6 H6B 171.8 2 . ? C5 C6 H6B 108.7 . . ? H6A C6 H6B 122.2 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.661 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.097 _database_code_depnum_ccdc_archive 'CCDC 961655' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H6 N8 Zn, C4 H9 N O' _chemical_formula_sum 'C8 H15 N9 O Zn' _chemical_formula_weight 318.66 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 Cc 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' _cell_length_a 13.2925(11) _cell_length_b 13.6600(7) _cell_length_c 9.5631(9) _cell_angle_alpha 90.00 _cell_angle_beta 126.840(13) _cell_angle_gamma 90.00 _cell_volume 1389.68(30) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1418 _cell_measurement_theta_min 2.6141 _cell_measurement_theta_max 29.0710 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 1.776 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7177 _exptl_absorpt_correction_T_max 0.7177 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2083 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2455 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1618 _reflns_number_gt 1569 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1051P)^2^+6.0103P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0100(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(4) _refine_ls_number_reflns 1618 _refine_ls_number_parameters 143 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1482 _refine_ls_wR_factor_gt 0.1460 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.056 _refine_ls_shift/su_mean 0.027 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 0.1664(10) 0.35645(5) 0.8701(13) 0.0280(3) Uani 1 1 d . . . N4 N 0.4941(12) 0.2004(5) 1.2089(16) 0.0287(16) Uani 1 1 d . . . N1 N 0.3125(13) 0.2682(5) 1.0207(17) 0.0310(17) Uani 1 1 d . . . N8 N 0.1807(12) 0.4650(5) 0.7382(16) 0.0290(16) Uani 1 1 d . . . N7 N 0.1763(12) 0.5677(5) 0.5622(16) 0.0285(16) Uani 1 1 d . . . N6 N 0.2610(13) 0.5983(6) 0.7296(17) 0.0418(19) Uani 1 1 d . . . N3 N 0.4023(13) 0.1303(5) 1.1369(18) 0.0368(18) Uani 1 1 d . . . N5 N 0.2629(13) 0.5378(5) 0.8348(15) 0.0397(18) Uani 1 1 d . . . C4 C 0.0330(14) 0.4232(7) 0.4223(19) 0.045(3) Uani 1 1 d . . . H4A H 0.0143 0.3673 0.4639 0.068 Uiso 1 1 calc R . . H4B H 0.0652 0.4017 0.3606 0.068 Uiso 1 1 calc R . . H4C H -0.0423 0.4606 0.3451 0.068 Uiso 1 1 calc R . . C1 C 0.4356(12) 0.2833(6) 1.1323(16) 0.0276(17) Uani 1 1 d . . . C3 C 0.1277(13) 0.4845(6) 0.5718(16) 0.0286(17) Uani 1 1 d . . . N2 N 0.2957(13) 0.1707(7) 1.0261(17) 0.0390(18) Uani 1 1 d . . . C2 C 0.4983(16) 0.3816(8) 1.172(2) 0.048(3) Uani 1 1 d . . . H2A H 0.4359 0.4308 1.1025 0.072 Uiso 1 1 calc R . . H2B H 0.5572 0.3802 1.1451 0.072 Uiso 1 1 calc R . . H2C H 0.5418 0.3964 1.2936 0.072 Uiso 1 1 calc R . . C6 C 0.3918(12) 0.6812(9) 1.2043(16) 0.065(3) Uiso 1 1 d D . . H6A H 0.4434 0.6893 1.1659 0.098 Uiso 1 1 calc R . . H6B H 0.3548 0.6171 1.1728 0.098 Uiso 1 1 calc R . . H6C H 0.4424 0.6888 1.3289 0.098 Uiso 1 1 calc R . . N9 N 0.3027(11) 0.8272(12) 1.0201(18) 0.126(6) Uiso 1 1 d D . . C5 C 0.2931(9) 0.7545(9) 1.1219(11) 0.151(9) Uiso 1 1 d D . . C8 C 0.2180(16) 0.9098(15) 0.935(3) 0.172(12) Uiso 1 1 d D . . H8A H 0.1567 0.9080 0.9575 0.258 Uiso 1 1 calc R . . H8B H 0.1763 0.9063 0.8113 0.258 Uiso 1 1 calc R . . H8C H 0.2650 0.9696 0.9798 0.258 Uiso 1 1 calc R . . O1 O 0.1979(10) 0.7767(10) 1.1122(18) 0.121(4) Uiso 1 1 d D . . C7 C 0.4102(15) 0.8038(19) 1.022(3) 0.199(13) Uiso 1 1 d D . . H7A H 0.4480 0.7441 1.0862 0.299 Uiso 1 1 calc R . . H7B H 0.4705 0.8559 1.0779 0.299 Uiso 1 1 calc R . . H7C H 0.3831 0.7958 0.9048 0.299 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 0.0189(5) 0.0255(5) 0.0289(5) 0.0019(4) 0.0086(4) -0.0024(5) N4 0.021(4) 0.030(4) 0.031(3) 0.003(3) 0.013(3) 0.003(3) N1 0.022(4) 0.033(4) 0.032(3) -0.004(3) 0.012(3) 0.000(3) N8 0.031(4) 0.026(4) 0.031(4) -0.006(3) 0.019(3) -0.006(3) N7 0.028(4) 0.025(4) 0.028(4) -0.004(3) 0.014(3) 0.000(3) N6 0.040(5) 0.044(4) 0.030(4) -0.002(4) 0.015(4) -0.014(4) N3 0.024(4) 0.032(4) 0.044(5) -0.001(3) 0.014(4) -0.002(3) N5 0.046(5) 0.035(4) 0.027(3) 0.001(3) 0.015(4) -0.005(4) C4 0.054(7) 0.042(6) 0.039(5) -0.008(4) 0.028(6) -0.018(5) C1 0.018(4) 0.026(4) 0.028(4) 0.001(3) 0.008(4) 0.000(3) C3 0.028(4) 0.030(4) 0.023(4) 0.000(3) 0.013(3) -0.001(3) N2 0.029(4) 0.034(4) 0.039(4) 0.003(4) 0.013(4) -0.003(4) C2 0.032(6) 0.030(5) 0.061(7) 0.004(5) 0.016(5) -0.005(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 Zn1 N4 1.998(8) 4_454 ? Zn1 N1 1.986(8) . ? Zn1 N8 2.028(7) . ? Zn1 N7 2.043(7) 2_565 ? N4 C1 1.319(11) . ? N4 N3 1.368(11) . ? N4 Zn1 1.998(8) 4 ? N1 C1 1.328(11) . ? N1 N2 1.356(11) . ? N8 C3 1.325(10) . ? N8 N5 1.352(10) . ? N7 C3 1.338(11) . ? N7 N6 1.358(10) . ? N7 Zn1 2.043(7) 2_564 ? N6 N5 1.290(10) . ? N3 N2 1.278(12) . ? C4 C3 1.474(12) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C1 C2 1.504(13) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C6 C5 1.4498(11) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? N9 C5 1.4495(11) . ? N9 C7 1.4503(11) . ? N9 C8 1.4501(11) . ? C5 O1 1.2497(11) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 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 N4 Zn1 N1 119.6(3) 4_454 . ? N4 Zn1 N8 107.2(3) 4_454 . ? N1 Zn1 N8 118.6(3) . . ? N4 Zn1 N7 108.5(3) 4_454 2_565 ? N1 Zn1 N7 98.5(3) . 2_565 ? N8 Zn1 N7 102.0(3) . 2_565 ? C1 N4 N3 105.7(7) . . ? C1 N4 Zn1 141.6(6) . 4 ? N3 N4 Zn1 112.3(6) . 4 ? C1 N1 N2 105.8(7) . . ? C1 N1 Zn1 133.4(6) . . ? N2 N1 Zn1 120.8(6) . . ? C3 N8 N5 107.6(6) . . ? C3 N8 Zn1 135.5(6) . . ? N5 N8 Zn1 116.9(5) . . ? C3 N7 N6 105.9(7) . . ? C3 N7 Zn1 136.0(5) . 2_564 ? N6 N7 Zn1 117.7(5) . 2_564 ? N5 N6 N7 109.7(7) . . ? N2 N3 N4 109.0(7) . . ? N6 N5 N8 108.0(6) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C1 N4 110.2(7) . . ? N1 C1 C2 124.8(8) . . ? N4 C1 C2 125.0(8) . . ? N8 C3 N7 108.8(6) . . ? N8 C3 C4 125.5(8) . . ? N7 C3 C4 125.7(7) . . ? N3 N2 N1 109.2(8) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 N9 C7 108.7(14) . . ? C5 N9 C8 123.9(14) . . ? C7 N9 C8 127.2(18) . . ? N9 C5 O1 106.1(12) . . ? N9 C5 C6 115.0(11) . . ? O1 C5 C6 138.9(13) . . ? N9 C8 H8A 109.4 . . ? N9 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N9 C8 H8C 109.6 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N9 C7 H7A 109.6 . . ? N9 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N9 C7 H7C 109.4 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.313 _refine_diff_density_min -0.609 _refine_diff_density_rms 0.108 _database_code_depnum_ccdc_archive 'CCDC 961656' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H15 N9 O Zn' _chemical_formula_sum 'C9 H15 N9 O Zn' _chemical_formula_weight 330.67 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 monoclinic _symmetry_space_group_name_H-M Cc 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' _cell_length_a 12.989(2) _cell_length_b 13.8218(9) _cell_length_c 9.2766(12) _cell_angle_alpha 90.00 _cell_angle_beta 124.43(2) _cell_angle_gamma 90.00 _cell_volume 1373.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2274 _cell_measurement_theta_min 2.4026 _cell_measurement_theta_max 27.4855 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 1.800 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7147 _exptl_absorpt_correction_T_max 0.7147 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn724+ (2x2 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4747 _diffrn_reflns_av_R_equivalents 0.0891 _diffrn_reflns_av_sigmaI/netI 0.1668 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1835 _reflns_number_gt 1338 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0006P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(2) _refine_ls_number_reflns 1835 _refine_ls_number_parameters 141 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.0960 _refine_ls_wR_factor_gt 0.0835 _refine_ls_goodness_of_fit_ref 0.817 _refine_ls_restrained_S_all 0.817 _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 0.72046(7) 0.84978(5) 0.38318(8) 0.0302(2) Uani 1 1 d . . . N4 N 0.3674(6) 0.7336(5) 0.0439(10) 0.0275(17) Uani 1 1 d . . . N1 N 0.5456(6) 0.8006(5) 0.2324(9) 0.0303(18) Uani 1 1 d . . . N7 N 0.8154(6) 0.9665(5) 0.8535(9) 0.0397(19) Uani 1 1 d . . . N5 N 0.7256(6) 0.9282(5) 0.5802(8) 0.0275(17) Uani 1 1 d . . . N6 N 0.8116(6) 0.9023(5) 0.7488(9) 0.0353(18) Uani 1 1 d . . . N9 N 0.8341(8) 0.6650(6) 0.0336(13) 0.063(3) Uiso 1 1 d . . . N3 N 0.3498(6) 0.8323(5) 0.0469(11) 0.0352(19) Uani 1 1 d . . . C1 C 0.4851(7) 0.7167(5) 0.1572(11) 0.0280(19) Uiso 1 1 d . . . C3 C 0.6815(6) 1.0128(6) 0.5915(11) 0.030(2) Uani 1 1 d . . . N8 N 0.7350(6) 1.0395(5) 0.7567(9) 0.0275(17) Uani 1 1 d . . . C2 C 0.5462(8) 0.6198(6) 0.1993(13) 0.045(3) Uani 1 1 d . . . H2A H 0.4849 0.5714 0.1282 0.067 Uiso 1 1 calc R . . H2B H 0.5834 0.6054 0.3205 0.067 Uiso 1 1 calc R . . H2C H 0.6096 0.6202 0.1763 0.067 Uiso 1 1 calc R . . C4 C 0.5823(8) 1.0696(7) 0.4334(11) 0.044(2) Uani 1 1 d . . . H4A H 0.5594 1.0357 0.3289 0.067 Uiso 1 1 calc R . . H4B H 0.6144 1.1323 0.4341 0.067 Uiso 1 1 calc R . . H4C H 0.5103 1.0769 0.4368 0.067 Uiso 1 1 calc R . . N2 N 0.4563(6) 0.8713(5) 0.1612(10) 0.0343(18) Uani 1 1 d . . . C6 C 0.9304(8) 0.8045(7) 0.1834(13) 0.056(3) Uiso 1 1 d . . . H6A H 0.8973 0.8672 0.1296 0.068 Uiso 1 1 calc R . . H6B H 0.9819 0.8125 0.3094 0.068 Uiso 1 1 calc R . . O1 O 0.7444(5) 0.7397(5) 0.1599(9) 0.0531(17) Uiso 1 1 d . . . C5 C 0.8250(8) 0.7334(7) 0.1289(13) 0.047(2) Uiso 1 1 d . . . C9 C 0.7495(11) 0.5847(7) -0.0334(14) 0.086(4) Uiso 1 1 d . . . H9A H 0.6949 0.5894 0.0051 0.129 Uiso 1 1 calc R . . H9B H 0.7959 0.5254 0.0085 0.129 Uiso 1 1 calc R . . H9C H 0.7010 0.5856 -0.1588 0.129 Uiso 1 1 calc R . . C7 C 1.0046(9) 0.7618(8) 0.1219(14) 0.068(3) Uiso 1 1 d . . . H7A H 1.0854 0.7398 0.2198 0.082 Uiso 1 1 calc R . . H7B H 1.0169 0.8085 0.0550 0.082 Uiso 1 1 calc R . . C8 C 0.9271(9) 0.6786(8) 0.0098(14) 0.069(3) Uiso 1 1 d . . . H8A H 0.8922 0.6926 -0.1120 0.083 Uiso 1 1 calc R . . H8B H 0.9779 0.6207 0.0427 0.083 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 0.0197(4) 0.0268(4) 0.0315(5) 0.0032(6) 0.0070(4) -0.0013(5) N4 0.022(4) 0.018(4) 0.028(4) 0.001(3) 0.005(3) 0.003(3) N1 0.020(3) 0.020(4) 0.036(5) 0.002(4) 0.007(4) 0.004(3) N7 0.036(4) 0.039(5) 0.027(4) 0.003(4) 0.007(4) 0.010(4) N5 0.025(4) 0.029(4) 0.022(4) -0.004(4) 0.009(3) 0.000(3) N6 0.040(4) 0.033(5) 0.024(4) 0.011(4) 0.013(4) 0.015(4) N3 0.031(4) 0.031(4) 0.041(5) 0.000(4) 0.019(4) 0.002(3) C3 0.022(4) 0.032(5) 0.037(6) 0.002(4) 0.018(4) -0.003(4) N8 0.028(4) 0.025(4) 0.027(4) 0.000(3) 0.014(3) 0.006(3) C2 0.037(6) 0.026(5) 0.054(7) 0.006(6) 0.015(6) 0.002(5) C4 0.049(6) 0.046(6) 0.024(5) 0.009(5) 0.013(5) 0.012(5) N2 0.027(4) 0.031(4) 0.038(5) -0.004(4) 0.015(4) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N1 1.997(7) . ? Zn1 N4 1.994(7) 4_565 ? Zn1 N8 2.001(7) 2_574 ? Zn1 N5 2.093(7) . ? N4 C1 1.295(9) . ? N4 N3 1.387(9) . ? N4 Zn1 1.994(7) 4_464 ? N1 N2 1.367(9) . ? N1 C1 1.352(10) . ? N7 N6 1.296(9) . ? N7 N8 1.361(9) . ? N5 C3 1.333(10) . ? N5 N6 1.359(9) . ? N9 C5 1.345(12) . ? N9 C9 1.432(12) . ? N9 C8 1.358(13) . ? N3 N2 1.292(9) . ? C1 C2 1.493(10) . ? C3 N8 1.328(10) . ? C3 C4 1.513(11) . ? N8 Zn1 2.001(7) 2_575 ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C6 C7 1.491(12) . ? C6 C5 1.522(12) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? O1 C5 1.236(11) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C7 C8 1.494(13) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? 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 N4 123.8(3) . 4_565 ? N1 Zn1 N8 107.3(3) . 2_574 ? N4 Zn1 N8 120.8(3) 4_565 2_574 ? N1 Zn1 N5 104.5(3) . . ? N4 Zn1 N5 95.8(3) 4_565 . ? N8 Zn1 N5 98.6(3) 2_574 . ? C1 N4 N3 107.0(7) . . ? C1 N4 Zn1 134.0(6) . 4_464 ? N3 N4 Zn1 119.0(5) . 4_464 ? N2 N1 C1 106.1(6) . . ? N2 N1 Zn1 114.4(5) . . ? C1 N1 Zn1 138.8(5) . . ? N6 N7 N8 108.9(7) . . ? C3 N5 N6 104.5(7) . . ? C3 N5 Zn1 136.1(6) . . ? N6 N5 Zn1 117.9(5) . . ? N7 N6 N5 109.9(6) . . ? C5 N9 C9 119.9(10) . . ? C5 N9 C8 115.2(9) . . ? C9 N9 C8 124.9(10) . . ? N2 N3 N4 108.3(7) . . ? N4 C1 N1 109.9(7) . . ? N4 C1 C2 125.6(8) . . ? N1 C1 C2 124.5(7) . . ? N8 C3 N5 111.5(7) . . ? N8 C3 C4 125.3(8) . . ? N5 C3 C4 123.2(8) . . ? C3 N8 N7 105.1(7) . . ? C3 N8 Zn1 136.7(6) . 2_575 ? N7 N8 Zn1 118.1(5) . 2_575 ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 N2 N1 108.7(7) . . ? C7 C6 C5 105.8(9) . . ? C7 C6 H6A 110.6 . . ? C5 C6 H6A 110.6 . . ? C7 C6 H6B 110.6 . . ? C5 C6 H6B 110.6 . . ? H6A C6 H6B 108.7 . . ? O1 C5 N9 127.1(10) . . ? O1 C5 C6 126.8(9) . . ? N9 C5 C6 106.0(8) . . ? N9 C9 H9A 109.5 . . ? N9 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N9 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C6 C7 C8 104.2(7) . . ? C6 C7 H7A 110.9 . . ? C8 C7 H7A 110.9 . . ? C6 C7 H7B 110.9 . . ? C8 C7 H7B 110.9 . . ? H7A C7 H7B 108.9 . . ? N9 C8 C7 107.7(11) . . ? N9 C8 H8A 110.2 . . ? C7 C8 H8A 110.2 . . ? N9 C8 H8B 110.2 . . ? C7 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.692 _refine_diff_density_min -0.644 _refine_diff_density_rms 0.141 #end _database_code_depnum_ccdc_archive 'CCDC 961657'