# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_p1 #TrackingRef 'web_deposit_cif_file_0_DiSun_1365081280.p1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 N3 O3 Zn0.50' _chemical_formula_weight 258.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M c2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.453(2) _cell_length_b 11.1544(17) _cell_length_c 16.508(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.666(3) _cell_angle_gamma 90.00 _cell_volume 2442.1(7) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2267 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 25.39 _exptl_crystal_description block _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 1.052 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8841 _exptl_absorpt_correction_T_max 0.9300 _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 APEX II CCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5901 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2140 _reflns_number_gt 1764 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT+ ver. (Bruker, 2001)' _computing_data_reduction 'SAINT+ ver. (Bruker, 2001)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0476P)^2^+0.9372P] 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 2140 _refine_ls_number_parameters 186 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0865 _refine_ls_wR_factor_gt 0.0797 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.002 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 0.5000 0.82332(3) 0.7500 0.05229(17) Uani 1 2 d S . . C1 C 0.70179(16) 0.74973(19) 0.71861(16) 0.0543(6) Uani 1 1 d . . . H1 H 0.6992 0.8067 0.6772 0.065 Uiso 1 1 calc R . . C2 C 0.66264(17) 0.6399(2) 0.81536(16) 0.0581(6) Uani 1 1 d . . . H2 H 0.6272 0.6068 0.8537 0.070 Uiso 1 1 calc R . . C3 C 0.75569(17) 0.6063(2) 0.80383(18) 0.0651(7) Uani 1 1 d . . . H3 H 0.7957 0.5468 0.8322 0.078 Uiso 1 1 calc R . . C4 C 0.87716(19) 0.6792(2) 0.7129(2) 0.0752(9) Uani 1 1 d . . . H4A H 0.8663 0.7005 0.6552 0.090 Uiso 1 1 calc R . . H4B H 0.9078 0.6003 0.7188 0.090 Uiso 1 1 calc R . . C5 C 0.94691(19) 0.7693(3) 0.7614(2) 0.0869(10) Uani 1 1 d . . . H5A H 0.9522 0.7517 0.8195 0.104 Uiso 1 1 calc R . . H5B H 0.9179 0.8487 0.7519 0.104 Uiso 1 1 calc R . . C6A C 0.5011(9) 0.9149(11) 0.6058(6) 0.040(3) Uani 0.50 1 d PD . . C6B C 0.4972(6) 0.8664(9) 0.5790(7) 0.043(3) Uani 0.50 1 d PD . . C7A C 0.5016(4) 1.0189(5) 0.5444(2) 0.0580(13) Uani 0.50 1 d PD . . H7AA H 0.5542 1.0820 0.5525 0.070 Uiso 0.50 1 d PR . . H7AB H 0.4431 1.0676 0.5460 0.070 Uiso 0.50 1 d PR . . C7B C 0.5048(4) 0.9318(3) 0.4985(4) 0.0527(12) Uani 0.50 1 d PD . . H7BA H 0.4526 0.9015 0.4566 0.063 Uiso 0.50 1 d PR . . H7BB H 0.5685 0.9121 0.4830 0.063 Uiso 0.50 1 d PR . . C8 C 0.8202(2) 0.8962(3) 0.50870(19) 0.0752(8) Uani 1 1 d . . . H8 H 0.8606 0.8291 0.5058 0.090 Uiso 1 1 calc R . . C9 C 0.7731(3) 1.0935(3) 0.4581(2) 0.0986(11) Uani 1 1 d . . . H9A H 0.7259 1.0854 0.4953 0.148 Uiso 1 1 calc R . . H9B H 0.7372 1.1068 0.4034 0.148 Uiso 1 1 calc R . . H9C H 0.8169 1.1603 0.4744 0.148 Uiso 1 1 calc R . . C10 C 0.9067(3) 0.9824(3) 0.4052(2) 0.1043(12) Uani 1 1 d . . . H10A H 0.9406 0.9064 0.4107 0.156 Uiso 1 1 calc R . . H10B H 0.9549 1.0455 0.4198 0.156 Uiso 1 1 calc R . . H10C H 0.8738 0.9929 0.3494 0.156 Uiso 1 1 calc R . . N1 N 0.62882(12) 0.73027(16) 0.76192(12) 0.0493(5) Uani 1 1 d . . . N2 N 0.77942(14) 0.67643(16) 0.74258(15) 0.0594(6) Uani 1 1 d . . . N3 N 0.83193(17) 0.9859(2) 0.45950(14) 0.0681(6) Uani 1 1 d . . . O1A O 0.4829(7) 0.8127(6) 0.5800(5) 0.066(3) Uani 0.50 1 d P . . O1B O 0.4800(7) 0.7579(5) 0.5734(5) 0.0623(16) Uani 0.50 1 d P . . O2B O 0.5096(6) 0.9289(7) 0.6442(4) 0.051(4) Uani 0.50 1 d P . . O2A O 0.5133(8) 0.9488(7) 0.6795(4) 0.0501(17) Uani 0.50 1 d P . . O3 O 0.76217(18) 0.8921(2) 0.55740(14) 0.0968(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0315(2) 0.0348(2) 0.0954(3) 0.000 0.02466(18) 0.000 C1 0.0412(12) 0.0398(12) 0.0878(18) 0.0028(11) 0.0277(12) 0.0047(10) C2 0.0449(13) 0.0536(14) 0.0786(17) 0.0099(12) 0.0190(12) 0.0014(11) C3 0.0433(13) 0.0514(14) 0.103(2) 0.0151(14) 0.0186(13) 0.0106(11) C4 0.0432(14) 0.0553(15) 0.139(3) -0.0014(15) 0.0503(16) 0.0079(11) C5 0.0452(16) 0.0702(18) 0.155(3) -0.0072(19) 0.0453(18) 0.0013(14) C6A 0.042(3) 0.026(5) 0.058(11) -0.007(6) 0.024(7) 0.001(4) C6B 0.029(3) 0.041(10) 0.063(5) -0.017(6) 0.016(3) -0.005(5) C7A 0.067(3) 0.040(3) 0.072(4) 0.002(3) 0.024(3) 0.001(2) C7B 0.059(3) 0.043(3) 0.060(4) -0.008(3) 0.024(3) -0.003(2) C8 0.082(2) 0.0609(17) 0.088(2) -0.0184(15) 0.0283(16) -0.0162(14) C9 0.101(3) 0.093(3) 0.108(3) 0.000(2) 0.034(2) 0.007(2) C10 0.115(3) 0.100(3) 0.115(3) -0.023(2) 0.070(2) -0.028(2) N1 0.0333(9) 0.0425(10) 0.0760(13) 0.0001(9) 0.0208(9) 0.0031(8) N2 0.0361(10) 0.0423(10) 0.1064(17) 0.0019(10) 0.0309(10) 0.0056(8) N3 0.0703(14) 0.0641(14) 0.0767(15) -0.0189(12) 0.0324(11) -0.0173(11) O1A 0.082(4) 0.043(8) 0.076(3) -0.015(5) 0.022(3) -0.011(5) O1B 0.071(3) 0.039(4) 0.082(3) -0.004(3) 0.029(2) -0.008(3) O2B 0.061(4) 0.045(4) 0.058(9) -0.009(6) 0.040(8) 0.002(3) O2A 0.059(2) 0.042(3) 0.057(5) 0.003(3) 0.033(4) 0.006(2) O3 0.1066(17) 0.0956(17) 0.1027(16) -0.0061(13) 0.0593(14) -0.0178(13) _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 O2A 1.849(9) . Y Zn1 N1 2.0012(17) . Y C1 N1 1.326(3) . ? C1 N2 1.333(3) . ? C1 H1 0.9300 . ? C2 C3 1.351(3) . ? C2 N1 1.366(3) . ? C2 H2 0.9300 . ? C3 N2 1.358(3) . ? C3 H3 0.9300 . ? C4 N2 1.478(3) . ? C4 C5 1.509(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C5 1.537(5) 2_756 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C8 O3 1.212(3) . ? C8 N3 1.315(4) . ? C8 H8 0.9300 . ? C9 N3 1.436(4) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 N3 1.456(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 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 O2A Zn1 O2A 81.6(4) 2_656 . Y O2A Zn1 N1 106.3(3) 2_656 2_656 Y O2A Zn1 N1 120.3(3) . 2_656 Y N1 Zn1 N1 117.51(10) 2_656 . Y N1 C1 N2 110.7(2) . . ? N1 C1 H1 124.6 . . ? N2 C1 H1 124.6 . . ? C3 C2 N1 109.3(2) . . ? C3 C2 H2 125.4 . . ? N1 C2 H2 125.4 . . ? C2 C3 N2 106.5(2) . . ? C2 C3 H3 126.8 . . ? N2 C3 H3 126.8 . . ? N2 C4 C5 110.3(2) . . ? N2 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? N2 C4 H4B 109.6 . . ? C5 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C4 C5 C5 113.0(3) . 2_756 ? C4 C5 H5A 109.0 . . ? C5 C5 H5A 109.0 2_756 . ? C4 C5 H5B 109.0 . . ? C5 C5 H5B 109.0 2_756 . ? O3 C8 N3 126.6(3) . . ? O3 C8 H8 116.7 . . ? N3 C8 H8 116.7 . . ? N3 C9 H9A 109.5 . . ? N3 C9 H9B 109.5 . . ? N3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 H10A 109.5 . . ? N3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C1 N1 C2 105.81(18) . . ? C1 N1 Zn1 124.71(16) . . ? C2 N1 Zn1 129.43(15) . . ? C1 N2 C3 107.69(18) . . ? C1 N2 C4 125.8(2) . . ? C3 N2 C4 126.3(2) . . ? C8 N3 C9 121.6(2) . . ? C8 N3 C10 121.8(3) . . ? C9 N3 C10 116.7(3) . . ? Zn1 O2A C6B 100.2(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.275 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 932564' ####################################################################### # # 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_p2 #TrackingRef 'web_deposit_cif_file_0_DiSun_1365081280.p1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H28 N4 O7 Zn' _chemical_formula_weight 501.83 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 7.3767(12) _cell_length_b 9.6740(16) _cell_length_c 16.395(3) _cell_angle_alpha 86.541(3) _cell_angle_beta 84.230(3) _cell_angle_gamma 83.400(3) _cell_volume 1154.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3390 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 27.24 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 1.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8783 _exptl_absorpt_correction_T_max 0.8970 _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 APEX II CCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5771 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4034 _reflns_number_gt 3600 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT+ ver. (Bruker, 2001)' _computing_data_reduction 'SAINT+ ver. (Bruker, 2001)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0424P)^2^+0.5736P] 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 4034 _refine_ls_number_parameters 312 _refine_ls_number_restraints 38 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0881 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.063 _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 0.82950(4) 0.21470(3) 0.307325(16) 0.03423(11) Uani 1 1 d . . . C1 C 1.1347(3) 0.0843(3) 0.19667(15) 0.0381(5) Uani 1 1 d . . . H1 H 1.2178 0.1328 0.2192 0.046 Uiso 1 1 calc R . . C2 C 0.8870(3) 0.0085(3) 0.17075(16) 0.0430(6) Uani 1 1 d . . . H2 H 0.7639 -0.0052 0.1723 0.052 Uiso 1 1 calc R . . C3 C 1.0230(4) -0.0561(3) 0.12173(16) 0.0457(6) Uani 1 1 d . . . H3 H 1.0123 -0.1214 0.0836 0.055 Uiso 1 1 calc R . . C4 C 1.3660(3) -0.0467(3) 0.10189(16) 0.0486(7) Uani 1 1 d D . . H4A H 1.3860 -0.1474 0.0997 0.058 Uiso 1 1 calc R . . H4B H 1.4532 -0.0184 0.1364 0.058 Uiso 1 1 calc R . . C5 C 1.4009(3) 0.0172(3) 0.01707(15) 0.0403(6) Uani 1 1 d . . . H5A H 1.3726 0.1176 0.0183 0.048 Uiso 1 1 calc R . . H5B H 1.3208 -0.0169 -0.0187 0.048 Uiso 1 1 calc R . . C6 C 1.1458(4) 0.3244(3) 0.37571(17) 0.0511(7) Uani 1 1 d . . . H6 H 1.1813 0.3691 0.3258 0.061 Uiso 1 1 calc R . . C7 C 1.0019(4) 0.2031(4) 0.46779(17) 0.0555(7) Uani 1 1 d . . . H7 H 0.9170 0.1473 0.4940 0.067 Uiso 1 1 calc R . . C8 C 1.1383(5) 0.2492(5) 0.50266(19) 0.0850(13) Uani 1 1 d . . . H8 H 1.1660 0.2316 0.5567 0.102 Uiso 1 1 calc R . . C9 C 1.4089(8) 0.3715(7) 0.4515(4) 0.0574(14) Uani 0.60 1 d PU . . H9A H 1.4869 0.3008 0.4786 0.069 Uiso 0.60 1 d PR . . H9B H 1.4685 0.3954 0.3986 0.069 Uiso 0.60 1 d PR . . C9A C 1.3502(13) 0.4504(11) 0.4483(7) 0.066(2) Uani 0.40 1 d PDU . . H9C H 1.3935 0.4858 0.3948 0.079 Uiso 0.40 1 d PR . . H9AA H 1.2555 0.5356 0.4781 0.079 Uiso 0.40 1 d PR . . C10 C 1.3643(9) 0.4991(7) 0.5014(4) 0.0716(16) Uani 0.60 1 d PU . . H10A H 1.3318 0.4656 0.5567 0.086 Uiso 0.60 1 d PR . . H9AB H 1.2531 0.5492 0.4800 0.086 Uiso 0.60 1 d PR . . C10A C 1.5008(12) 0.3989(9) 0.4950(5) 0.063(2) Uani 0.40 1 d PU . . H9D H 1.5607 0.3195 0.4669 0.076 Uiso 0.40 1 d PR . . H10B H 1.4547 0.3681 0.5491 0.076 Uiso 0.40 1 d PR . . C11 C 0.5428(3) 0.0686(2) 0.34306(15) 0.0355(5) Uani 1 1 d . . . C12 C 0.4194(4) -0.0344(3) 0.38512(16) 0.0453(6) Uani 1 1 d . . . H12A H 0.4679 -0.0712 0.4358 0.054 Uiso 1 1 calc R . . H12B H 0.2983 0.0136 0.3989 0.054 Uiso 1 1 calc R . . C13 C 0.4035(3) -0.1534(2) 0.33194(15) 0.0364(5) Uani 1 1 d . . . C14 C 0.2347(4) -0.1962(3) 0.32270(18) 0.0468(6) Uani 1 1 d . . . H14 H 0.1290 -0.1512 0.3493 0.056 Uiso 1 1 calc R . . C15 C 0.2228(4) -0.3057(3) 0.2739(2) 0.0605(8) Uani 1 1 d . . . H15 H 0.1089 -0.3351 0.2688 0.073 Uiso 1 1 calc R . . C16 C 0.3769(5) -0.3717(3) 0.23283(19) 0.0570(8) Uani 1 1 d . . . H16 H 0.3663 -0.4448 0.1999 0.068 Uiso 1 1 calc R . . C17 C 0.5474(4) -0.3303(2) 0.23990(15) 0.0415(6) Uani 1 1 d . . . C18 C 0.5577(3) -0.2226(2) 0.29027(15) 0.0369(5) Uani 1 1 d . . . H18 H 0.6721 -0.1953 0.2966 0.044 Uiso 1 1 calc R . . C19 C 0.7176(4) -0.3977(3) 0.19327(18) 0.0540(7) Uani 1 1 d . . . H19A H 0.8081 -0.3317 0.1863 0.065 Uiso 1 1 calc R . . H19B H 0.6877 -0.4165 0.1390 0.065 Uiso 1 1 calc R . . C20 C 0.8029(4) -0.5311(3) 0.23223(15) 0.0411(6) Uani 1 1 d . . . N1 N 0.9570(3) 0.0978(2) 0.21833(12) 0.0340(4) Uani 1 1 d . . . N2 N 1.1805(3) -0.0069(2) 0.13885(12) 0.0381(5) Uani 1 1 d D . . N3 N 1.0072(3) 0.2508(2) 0.38793(12) 0.0398(5) Uani 1 1 d . . . N4 N 1.2291(4) 0.3277(4) 0.44288(15) 0.0754(9) Uani 1 1 d D . . O1 O 0.6771(2) 0.0931(2) 0.38031(11) 0.0472(4) Uani 1 1 d . . . O1W O 0.8603(4) 0.3267(3) 0.01096(16) 0.0841(7) Uani 1 1 d . . . H1WA H 0.7739 0.3169 0.0486 0.101 Uiso 1 1 d R . . H1WB H 0.9593 0.3394 0.0305 0.120(19) Uiso 1 1 d R . . O2 O 0.5105(2) 0.12290(19) 0.27582(12) 0.0475(4) Uani 1 1 d . . . O2W O 0.5372(4) 0.2898(3) 0.11555(15) 0.0743(7) Uani 1 1 d . . . H2WA H 0.4370 0.3424 0.1137 0.34(6) Uiso 1 1 d R . . H2WB H 0.5500 0.2764 0.1665 0.107(16) Uiso 1 1 d R . . O3 O 0.9699(3) -0.5653(2) 0.21923(13) 0.0582(5) Uani 1 1 d . . . O3W O 0.1918(3) 0.4124(3) 0.07558(15) 0.0768(7) Uani 1 1 d . . . H3WA H 0.1693 0.4965 0.0580 0.25(4) Uiso 1 1 d R . . H3WB H 0.1324 0.4332 0.1212 0.086(13) Uiso 1 1 d R . . O4 O 0.6969(3) -0.60553(18) 0.27688(12) 0.0485(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.03549(17) 0.03285(16) 0.03499(17) -0.00317(11) -0.00399(11) -0.00514(11) C1 0.0327(13) 0.0459(14) 0.0370(13) -0.0026(11) -0.0031(10) -0.0096(10) C2 0.0319(13) 0.0557(16) 0.0439(14) -0.0125(12) -0.0027(11) -0.0107(11) C3 0.0434(15) 0.0536(16) 0.0425(14) -0.0162(12) -0.0031(11) -0.0090(12) C4 0.0328(13) 0.0680(18) 0.0400(14) 0.0045(13) 0.0031(11) 0.0059(12) C5 0.0323(13) 0.0522(15) 0.0350(13) -0.0026(11) -0.0008(10) 0.0000(11) C6 0.0462(15) 0.0713(19) 0.0401(15) -0.0025(13) -0.0086(12) -0.0205(14) C7 0.0442(16) 0.083(2) 0.0411(15) 0.0036(14) -0.0033(12) -0.0204(15) C8 0.057(2) 0.167(4) 0.0379(17) 0.006(2) -0.0091(15) -0.044(2) C9 0.037(3) 0.076(4) 0.063(3) 0.000(3) -0.016(3) -0.014(3) C9A 0.049(5) 0.095(7) 0.063(5) 0.013(6) -0.033(4) -0.026(5) C10 0.081(4) 0.073(4) 0.072(4) -0.007(3) -0.021(3) -0.041(3) C10A 0.070(5) 0.060(4) 0.068(5) -0.005(4) -0.022(4) -0.029(4) C11 0.0367(13) 0.0302(12) 0.0400(14) -0.0087(10) 0.0027(10) -0.0073(10) C12 0.0503(15) 0.0441(14) 0.0426(14) -0.0041(11) 0.0074(12) -0.0189(12) C13 0.0410(13) 0.0323(12) 0.0370(13) 0.0070(10) -0.0061(10) -0.0121(10) C14 0.0378(14) 0.0454(15) 0.0582(17) 0.0092(13) -0.0064(12) -0.0133(11) C15 0.0547(18) 0.0497(17) 0.085(2) 0.0051(16) -0.0266(17) -0.0253(14) C16 0.077(2) 0.0366(14) 0.0639(19) -0.0041(13) -0.0233(16) -0.0193(14) C17 0.0563(16) 0.0266(12) 0.0419(14) 0.0066(10) -0.0081(12) -0.0073(11) C18 0.0397(13) 0.0325(12) 0.0406(13) 0.0049(10) -0.0085(11) -0.0119(10) C19 0.078(2) 0.0347(14) 0.0471(16) 0.0025(12) 0.0044(14) -0.0086(13) C20 0.0513(16) 0.0354(13) 0.0385(13) -0.0069(10) -0.0033(11) -0.0113(11) N1 0.0296(10) 0.0384(11) 0.0348(10) -0.0046(8) -0.0024(8) -0.0061(8) N2 0.0316(10) 0.0497(12) 0.0317(10) 0.0000(9) 0.0008(8) -0.0028(9) N3 0.0363(11) 0.0471(12) 0.0379(11) -0.0066(9) -0.0055(9) -0.0088(9) N4 0.0514(15) 0.142(3) 0.0423(14) -0.0080(16) -0.0082(12) -0.0484(17) O1 0.0442(10) 0.0558(11) 0.0453(10) 0.0008(8) -0.0077(8) -0.0196(9) O1W 0.0868(19) 0.0939(19) 0.0759(17) -0.0079(14) -0.0084(14) -0.0261(15) O2 0.0468(10) 0.0491(11) 0.0491(11) 0.0077(9) -0.0087(8) -0.0167(8) O2W 0.0755(16) 0.0879(18) 0.0606(15) 0.0014(12) -0.0158(12) -0.0083(13) O3 0.0503(12) 0.0641(13) 0.0600(13) 0.0042(10) -0.0006(10) -0.0123(10) O3W 0.0713(16) 0.098(2) 0.0575(15) -0.0002(13) -0.0016(12) -0.0010(13) O4 0.0480(11) 0.0341(9) 0.0608(12) 0.0086(8) 0.0027(9) -0.0062(8) _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 O4 1.9577(18) 1_565 ? Zn1 O1 1.9855(17) . ? Zn1 N1 1.9925(19) . ? Zn1 N3 2.024(2) . ? C1 N1 1.317(3) . ? C1 N2 1.326(3) . ? C1 H1 0.9300 . ? C2 C3 1.341(4) . ? C2 N1 1.374(3) . ? C2 H2 0.9300 . ? C3 N2 1.365(3) . ? C3 H3 0.9300 . ? C4 N2 1.459(3) . ? C4 C5 1.498(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C5 1.519(5) 2_855 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N3 1.305(3) . ? C6 N4 1.318(4) . ? C6 H6 0.9300 . ? C7 C8 1.337(4) . ? C7 N3 1.360(3) . ? C7 H7 0.9300 . ? C8 N4 1.372(4) . ? C8 H8 0.9300 . ? C11 O2 1.226(3) . ? C11 O1 1.267(3) . ? C11 C12 1.516(3) . ? C12 C13 1.507(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.382(3) . ? C13 C18 1.390(4) . ? C14 C15 1.381(4) . ? C14 H14 0.9300 . ? C15 C16 1.373(5) . ? C15 H15 0.9300 . ? C16 C17 1.381(4) . ? C16 H16 0.9300 . ? C17 C18 1.381(3) . ? C17 C19 1.504(4) . ? C18 H18 0.9300 . ? C19 C20 1.505(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 O3 1.239(3) . ? C20 O4 1.271(3) . ? O1W H1WA 0.8500 . ? O1W H1WB 0.8502 . ? O2W H2WA 0.8500 . ? O2W H2WB 0.8499 . ? O3W H3WA 0.8500 . ? O3W H3WB 0.8500 . ? O4 Zn1 1.9577(18) 1_545 ? 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 O4 Zn1 O1 113.28(8) 1_565 . ? O4 Zn1 N1 118.57(8) 1_565 . ? O1 Zn1 N1 106.96(8) . . ? O4 Zn1 N3 107.32(9) 1_565 . ? O1 Zn1 N3 98.37(8) . . ? N1 Zn1 N3 110.49(8) . . ? N1 C1 N2 111.7(2) . . ? N1 C1 H1 124.1 . . ? N2 C1 H1 124.1 . . ? C3 C2 N1 109.7(2) . . ? C3 C2 H2 125.2 . . ? N1 C2 H2 125.2 . . ? C2 C3 N2 106.3(2) . . ? C2 C3 H3 126.8 . . ? N2 C3 H3 126.8 . . ? N2 C4 C5 112.7(2) . . ? N2 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? N2 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C4 C5 C5 111.4(3) . 2_855 ? C4 C5 H5A 109.3 . . ? C5 C5 H5A 109.3 2_855 . ? C4 C5 H5B 109.3 . . ? C5 C5 H5B 109.3 2_855 . ? H5A C5 H5B 108.0 . . ? N3 C6 N4 111.6(3) . . ? N3 C6 H6 124.2 . . ? N4 C6 H6 124.2 . . ? C8 C7 N3 109.2(3) . . ? C8 C7 H7 125.4 . . ? N3 C7 H7 125.4 . . ? C7 C8 N4 106.3(3) . . ? C7 C8 H8 126.9 . . ? N4 C8 H8 126.9 . . ? O2 C11 O1 123.3(2) . . ? O2 C11 C12 119.8(2) . . ? O1 C11 C12 116.9(2) . . ? C13 C12 C11 112.2(2) . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C18 118.0(2) . . ? C14 C13 C12 120.9(2) . . ? C18 C13 C12 121.1(2) . . ? C13 C14 C15 120.1(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 120.8(3) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 120.6(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C18 118.0(3) . . ? C16 C17 C19 121.6(3) . . ? C18 C17 C19 120.5(2) . . ? C17 C18 C13 122.5(2) . . ? C17 C18 H18 118.7 . . ? C13 C18 H18 118.7 . . ? C17 C19 C20 115.5(2) . . ? C17 C19 H19A 108.4 . . ? C20 C19 H19A 108.4 . . ? C17 C19 H19B 108.4 . . ? C20 C19 H19B 108.4 . . ? H19A C19 H19B 107.5 . . ? O3 C20 O4 122.7(2) . . ? O3 C20 C19 119.9(2) . . ? O4 C20 C19 117.4(2) . . ? C1 N1 C2 105.0(2) . . ? C1 N1 Zn1 125.49(16) . . ? C2 N1 Zn1 129.35(16) . . ? C1 N2 C3 107.2(2) . . ? C1 N2 C4 125.6(2) . . ? C3 N2 C4 127.2(2) . . ? C6 N3 C7 106.1(2) . . ? C6 N3 Zn1 128.24(18) . . ? C7 N3 Zn1 125.70(18) . . ? C6 N4 C8 106.9(2) . . ? C6 N4 C9 128.7(3) . . ? C8 N4 C9 122.7(4) . . ? C6 N4 C9A 117.4(4) . . ? C8 N4 C9A 131.5(5) . . ? C9 N4 C9A 31.6(4) . . ? C11 O1 Zn1 108.62(15) . . ? H1WA O1W H1WB 111.9 . . ? H2WA O2W H2WB 104.5 . . ? H3WA O3W H3WB 89.3 . . ? C20 O4 Zn1 110.28(17) . 1_545 ? 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 O1W H1WA O2W 0.85 2.00 2.837(4) 166.9 . O1W H1WB O3W 0.85 2.14 2.980(4) 169.1 1_655 O2W H2WA O3W 0.85 2.00 2.807(4) 157.1 . O2W H2WB O2 0.85 2.28 3.001(3) 143.4 . O3W H3WA O1W 0.85 2.00 2.826(4) 165.3 2_665 O3W H3WB O3 0.85 1.91 2.735(3) 164.4 1_465 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.430 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 932565' ####################################################################### # # 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_p3 #TrackingRef 'web_deposit_cif_file_0_DiSun_1365081280.p1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H33 N5 O7 Zn' _chemical_formula_weight 508.87 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' Zn Zn 0.2839 1.4301 '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 9.1919(12) _cell_length_b 11.4363(14) _cell_length_c 13.0821(16) _cell_angle_alpha 66.308(2) _cell_angle_beta 78.744(2) _cell_angle_gamma 80.613(2) _cell_volume 1229.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1692 _cell_measurement_theta_min 5.440 _cell_measurement_theta_max 45.082 _exptl_crystal_description block _exptl_crystal_colour Pale-yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 1.045 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8590 _exptl_absorpt_correction_T_max 0.9693 _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 APEX II CCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6026 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0603 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4255 _reflns_number_gt 3440 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT+ ver. (Bruker, 2001)' _computing_data_reduction 'SAINT+ ver. (Bruker, 2001)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0497P)^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 4255 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.99746(4) 0.21291(3) 0.79485(3) 0.02880(14) Uani 1 1 d . . . C1 C 0.9603(3) 0.3295(3) 0.5501(3) 0.0349(8) Uani 1 1 d . . . H1 H 0.8594 0.3176 0.5663 0.042 Uiso 1 1 calc R . . C2 C 1.1862(4) 0.3368(3) 0.5677(3) 0.0388(8) Uani 1 1 d . . . H2 H 1.2708 0.3303 0.5994 0.047 Uiso 1 1 calc R . . C3 C 1.1807(4) 0.3769(3) 0.4557(3) 0.0428(8) Uani 1 1 d . . . H3 H 1.2593 0.4029 0.3974 0.051 Uiso 1 1 calc R . . C4 C 0.9758(4) 0.4045(3) 0.3395(3) 0.0419(8) Uani 1 1 d . . . H4A H 0.9830 0.4948 0.2933 0.050 Uiso 1 1 calc R . . H4B H 0.8713 0.3894 0.3568 0.050 Uiso 1 1 calc R . . C5 C 1.0597(4) 0.3253(3) 0.2746(3) 0.0428(8) Uani 1 1 d . . . H5A H 1.0590 0.2351 0.3230 0.051 Uiso 1 1 calc R . . H5B H 1.1625 0.3454 0.2527 0.051 Uiso 1 1 calc R . . C6 C 0.9919(4) 0.3500(3) 0.1691(3) 0.0479(9) Uani 1 1 d . . . H6A H 0.8958 0.3155 0.1920 0.057 Uiso 1 1 calc R . . H6B H 0.9753 0.4418 0.1281 0.057 Uiso 1 1 calc R . . C7 C 1.0892(5) 0.2907(3) 0.0908(3) 0.0491(9) Uani 1 1 d . . . H7A H 1.0421 0.3134 0.0243 0.059 Uiso 1 1 calc R . . H7B H 1.1845 0.3266 0.0666 0.059 Uiso 1 1 calc R . . C8 C 1.0390(4) 0.0657(3) 0.1337(3) 0.0366(8) Uani 1 1 d . . . H8 H 0.9621 0.0879 0.0905 0.044 Uiso 1 1 calc R . . C9 C 1.2019(4) -0.0436(3) 0.2429(3) 0.0424(8) Uani 1 1 d . . . H9 H 1.2578 -0.1126 0.2899 0.051 Uiso 1 1 calc R . . C10 C 1.2202(4) 0.0798(3) 0.2133(3) 0.0443(9) Uani 1 1 d . . . H10 H 1.2900 0.1121 0.2352 0.053 Uiso 1 1 calc R . . C11 C 0.7575(3) 0.3456(3) 0.8821(3) 0.0341(7) Uani 1 1 d . . . C12 C 0.6698(4) 0.3835(4) 0.9775(3) 0.0458(9) Uani 1 1 d . . . H12A H 0.6364 0.3063 1.0388 0.055 Uiso 1 1 calc R . . H12B H 0.7376 0.4171 1.0049 0.055 Uiso 1 1 calc R . . C13 C 0.5359(4) 0.4806(3) 0.9508(3) 0.0434(9) Uani 1 1 d . . . H13A H 0.4627 0.4450 0.9302 0.052 Uiso 1 1 calc R . . H13B H 0.5662 0.5565 0.8864 0.052 Uiso 1 1 calc R . . C14 C 1.2635(3) 0.2132(3) 0.8565(3) 0.0342(7) Uani 1 1 d . . . C15 C 1.4056(4) 0.1637(3) 0.9092(3) 0.0431(9) Uani 1 1 d . . . H15A H 1.4891 0.1940 0.8505 0.052 Uiso 1 1 calc R . . H15B H 1.4040 0.2017 0.9637 0.052 Uiso 1 1 calc R . . C16 C 1.4337(3) 0.0198(3) 0.9674(3) 0.0387(8) Uani 1 1 d . . . H16A H 1.4519 -0.0184 0.9114 0.046 Uiso 1 1 calc R . . H16B H 1.3452 -0.0132 1.0190 0.046 Uiso 1 1 calc R . . C17 C 0.4545(7) 0.8145(5) 0.6505(5) 0.0977(18) Uani 1 1 d . . . H17 H 0.4502 0.7549 0.6197 0.117 Uiso 1 1 calc R . . C18 C 0.2471(7) 0.9395(7) 0.5538(6) 0.152(3) Uani 1 1 d . . . H18A H 0.2689 1.0128 0.4858 0.227 Uiso 1 1 calc R . . H18B H 0.1502 0.9556 0.5919 0.227 Uiso 1 1 calc R . . H18C H 0.2488 0.8658 0.5357 0.227 Uiso 1 1 calc R . . C19 C 0.3593(8) 1.0036(7) 0.6730(6) 0.156(3) Uani 1 1 d . . . H19A H 0.3884 0.9587 0.7467 0.233 Uiso 1 1 calc R . . H19B H 0.2624 1.0487 0.6793 0.233 Uiso 1 1 calc R . . H19C H 0.4300 1.0637 0.6265 0.233 Uiso 1 1 calc R . . N1 N 1.0465(3) 0.3068(2) 0.6273(2) 0.0315(6) Uani 1 1 d . . . N2 N 1.0362(3) 0.3718(2) 0.4452(2) 0.0330(6) Uani 1 1 d . . . N3 N 1.0874(3) -0.0531(3) 0.1931(2) 0.0345(6) Uani 1 1 d . . . N4 N 1.1149(3) 0.1503(3) 0.1437(2) 0.0375(6) Uani 1 1 d . . . N5 N 0.3550(4) 0.9164(4) 0.6248(3) 0.0710(10) Uani 1 1 d . . . O1 O 0.8794(2) 0.2771(2) 0.90522(19) 0.0452(6) Uani 1 1 d . . . O1W O 0.4593(3) 0.4774(3) 0.6812(2) 0.0649(8) Uani 1 1 d . . . H1WA H 0.5459 0.4649 0.6997 0.078 Uiso 1 1 d R . . H1WB H 0.3910 0.4361 0.7299 0.078 Uiso 1 1 d R . . O2 O 0.7120(3) 0.3793(3) 0.7907(2) 0.0525(7) Uani 1 1 d . . . O2W O 0.4029(3) 0.6652(3) 0.4611(3) 0.0710(8) Uani 1 1 d . . . H2WA H 0.4289 0.6151 0.5244 0.085 Uiso 1 1 d R . . H2WB H 0.4332 0.6350 0.4101 0.085 Uiso 1 1 d R . . O3 O 1.1818(2) 0.1306(2) 0.86218(19) 0.0394(5) Uani 1 1 d . . . O4 O 1.2313(3) 0.3309(2) 0.8104(2) 0.0481(6) Uani 1 1 d . . . O5 O 0.5508(5) 0.7907(4) 0.7102(4) 0.1171(15) 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 Zn1 0.0297(2) 0.0316(2) 0.0259(2) -0.01250(16) -0.00850(14) 0.00426(15) C1 0.0365(17) 0.0350(19) 0.0311(18) -0.0126(15) -0.0062(15) 0.0043(14) C2 0.0363(18) 0.048(2) 0.0356(19) -0.0171(17) -0.0093(15) -0.0049(16) C3 0.043(2) 0.051(2) 0.0325(19) -0.0149(17) -0.0007(15) -0.0075(17) C4 0.063(2) 0.0337(19) 0.0290(18) -0.0105(15) -0.0190(16) 0.0058(17) C5 0.058(2) 0.040(2) 0.0347(19) -0.0176(16) -0.0140(16) 0.0016(17) C6 0.076(3) 0.035(2) 0.036(2) -0.0130(16) -0.0225(18) 0.0016(18) C7 0.078(3) 0.038(2) 0.0333(19) -0.0126(17) -0.0144(18) -0.0070(19) C8 0.0421(19) 0.041(2) 0.0303(18) -0.0162(16) -0.0091(15) -0.0020(16) C9 0.0419(19) 0.044(2) 0.043(2) -0.0160(17) -0.0161(16) 0.0028(16) C10 0.047(2) 0.045(2) 0.048(2) -0.0194(18) -0.0193(17) -0.0058(17) C11 0.0357(18) 0.0349(18) 0.0323(18) -0.0150(15) -0.0054(15) 0.0015(15) C12 0.0432(19) 0.055(2) 0.039(2) -0.0256(18) -0.0053(16) 0.0144(17) C13 0.0382(19) 0.047(2) 0.044(2) -0.0225(18) -0.0033(15) 0.0086(16) C14 0.0294(17) 0.043(2) 0.0277(17) -0.0125(16) -0.0085(13) 0.0073(15) C15 0.0370(18) 0.042(2) 0.048(2) -0.0110(17) -0.0193(16) 0.0027(16) C16 0.0305(17) 0.045(2) 0.0376(19) -0.0115(16) -0.0141(14) 0.0034(15) C17 0.108(4) 0.074(4) 0.140(5) -0.062(4) -0.047(4) 0.004(3) C18 0.118(5) 0.173(7) 0.145(7) -0.010(6) -0.070(5) -0.036(5) C19 0.192(8) 0.154(7) 0.170(7) -0.124(6) -0.067(6) 0.064(6) N1 0.0337(14) 0.0346(15) 0.0248(14) -0.0099(12) -0.0078(11) 0.0007(12) N2 0.0436(16) 0.0306(15) 0.0258(14) -0.0113(12) -0.0106(12) 0.0022(12) N3 0.0375(15) 0.0358(16) 0.0310(15) -0.0128(13) -0.0095(12) -0.0004(12) N4 0.0514(17) 0.0329(15) 0.0323(15) -0.0137(13) -0.0122(13) -0.0042(13) N5 0.075(2) 0.066(3) 0.074(3) -0.029(2) -0.017(2) 0.004(2) O1 0.0414(13) 0.0590(16) 0.0414(14) -0.0296(12) -0.0141(11) 0.0160(12) O1W 0.0552(16) 0.079(2) 0.0504(17) -0.0089(15) -0.0134(13) -0.0150(15) O2 0.0456(14) 0.0700(18) 0.0409(15) -0.0251(14) -0.0113(12) 0.0136(13) O2W 0.0705(19) 0.068(2) 0.074(2) -0.0281(17) -0.0210(16) 0.0078(16) O3 0.0341(12) 0.0418(14) 0.0442(14) -0.0167(11) -0.0181(10) 0.0069(11) O4 0.0444(14) 0.0412(15) 0.0521(16) -0.0095(12) -0.0208(12) 0.0091(11) O5 0.110(3) 0.093(3) 0.167(4) -0.046(3) -0.080(3) 0.003(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 O1 1.945(2) . Y Zn1 O3 1.982(2) . Y Zn1 N1 2.010(2) . Y Zn1 N3 2.040(3) 2_756 Y C1 N1 1.324(4) . ? C1 N2 1.344(4) . ? C1 H1 0.9300 . ? C2 C3 1.356(4) . ? C2 N1 1.383(4) . ? C2 H2 0.9300 . ? C3 N2 1.374(4) . ? C3 H3 0.9300 . ? C4 N2 1.477(4) . ? C4 C5 1.506(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.528(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.520(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N4 1.469(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N3 1.318(4) . ? C8 N4 1.341(4) . ? C8 H8 0.9300 . ? C9 C10 1.335(5) . ? C9 N3 1.381(4) . ? C9 H9 0.9300 . ? C10 N4 1.384(4) . ? C10 H10 0.9300 . ? C11 O2 1.235(4) . ? C11 O1 1.271(4) . ? C11 C12 1.524(4) . ? C12 C13 1.510(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C13 1.523(6) 2_667 ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 O4 1.245(4) . ? C14 O3 1.271(4) . ? C14 C15 1.516(4) . ? C15 C16 1.512(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C16 1.529(6) 2_857 ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 O5 1.220(6) . ? C17 N5 1.328(6) . ? C17 H17 0.9300 . ? C18 N5 1.410(6) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 N5 1.387(7) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N3 Zn1 2.040(3) 2_756 ? O1W H1WA 0.8500 . ? O1W H1WB 0.8500 . ? O2W H2WA 0.8500 . ? O2W H2WB 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O3 103.26(9) . . Y O1 Zn1 N1 128.50(10) . . Y O3 Zn1 N1 110.39(10) . . Y O1 Zn1 N3 109.18(11) . 2_756 Y O3 Zn1 N3 99.06(10) . 2_756 Y N1 Zn1 N3 102.79(10) . 2_756 Y N1 C1 N2 111.8(3) . . ? N1 C1 H1 124.1 . . ? N2 C1 H1 124.1 . . ? C3 C2 N1 109.4(3) . . ? C3 C2 H2 125.3 . . ? N1 C2 H2 125.3 . . ? C2 C3 N2 106.6(3) . . ? C2 C3 H3 126.7 . . ? N2 C3 H3 126.7 . . ? N2 C4 C5 111.0(3) . . ? N2 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? N2 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 112.0(3) . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 113.3(3) . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6B 108.9 . . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? N4 C7 C6 113.1(3) . . ? N4 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? N4 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? N3 C8 N4 111.2(3) . . ? N3 C8 H8 124.4 . . ? N4 C8 H8 124.4 . . ? C10 C9 N3 109.6(3) . . ? C10 C9 H9 125.2 . . ? N3 C9 H9 125.2 . . ? C9 C10 N4 106.6(3) . . ? C9 C10 H10 126.7 . . ? N4 C10 H10 126.7 . . ? O2 C11 O1 123.7(3) . . ? O2 C11 C12 122.0(3) . . ? O1 C11 C12 114.3(3) . . ? C13 C12 C11 117.3(3) . . ? C13 C12 H12A 108.0 . . ? C11 C12 H12A 108.0 . . ? C13 C12 H12B 108.0 . . ? C11 C12 H12B 108.0 . . ? H12A C12 H12B 107.2 . . ? C12 C13 C13 112.9(4) . 2_667 ? C12 C13 H13A 109.0 . . ? C13 C13 H13A 109.0 2_667 . ? C12 C13 H13B 109.0 . . ? C13 C13 H13B 109.0 2_667 . ? H13A C13 H13B 107.8 . . ? O4 C14 O3 122.9(3) . . ? O4 C14 C15 119.6(3) . . ? O3 C14 C15 117.4(3) . . ? C16 C15 C14 116.4(3) . . ? C16 C15 H15A 108.2 . . ? C14 C15 H15A 108.2 . . ? C16 C15 H15B 108.2 . . ? C14 C15 H15B 108.2 . . ? H15A C15 H15B 107.3 . . ? C15 C16 C16 112.5(4) . 2_857 ? C15 C16 H16A 109.1 . . ? C16 C16 H16A 109.1 2_857 . ? C15 C16 H16B 109.1 . . ? C16 C16 H16B 109.1 2_857 . ? H16A C16 H16B 107.8 . . ? O5 C17 N5 127.1(5) . . ? O5 C17 H17 116.5 . . ? N5 C17 H17 116.5 . . ? N5 C18 H18A 109.5 . . ? N5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N5 C19 H19A 109.5 . . ? N5 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N5 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C1 N1 C2 105.3(3) . . ? C1 N1 Zn1 127.0(2) . . ? C2 N1 Zn1 126.4(2) . . ? C1 N2 C3 106.9(3) . . ? C1 N2 C4 126.3(3) . . ? C3 N2 C4 126.8(3) . . ? C8 N3 C9 105.9(3) . . ? C8 N3 Zn1 124.9(2) . 2_756 ? C9 N3 Zn1 129.3(2) . 2_756 ? C8 N4 C10 106.8(3) . . ? C8 N4 C7 126.0(3) . . ? C10 N4 C7 127.2(3) . . ? C17 N5 C19 116.3(5) . . ? C17 N5 C18 124.5(5) . . ? C19 N5 C18 119.2(5) . . ? C11 O1 Zn1 118.9(2) . . ? H1WA O1W H1WB 118.0 . . ? H2WA O2W H2WB 112.4 . . ? C14 O3 Zn1 111.7(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 O1W H1WA O2 0.85 2.00 2.803(3) 157.9 . O1W H1WB O4 0.85 1.91 2.747(4) 166.0 1_455 O2W H2WA O1W 0.85 2.06 2.902(4) 169.9 . O2W H2WB O1W 0.85 2.10 2.928(4) 164.1 2_666 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.333 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 932566' ####################################################################### # # 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_p4 #TrackingRef 'web_deposit_cif_file_0_DiSun_1365081280.p1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H29 N4 O6.50 Zn' _chemical_formula_weight 458.81 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 8.2532(11) _cell_length_b 9.6073(12) _cell_length_c 14.1941(19) _cell_angle_alpha 96.513(2) _cell_angle_beta 96.661(2) _cell_angle_gamma 104.406(2) _cell_volume 1070.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1478 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 21.56 _exptl_crystal_description block _exptl_crystal_colour Pale-yellow _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 482 _exptl_absorpt_coefficient_mu 1.188 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8804 _exptl_absorpt_correction_T_max 0.9109 _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 APEX II CCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5363 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3724 _reflns_number_gt 2936 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT+ ver. (Bruker, 2001)' _computing_data_reduction 'SAINT+ ver. (Bruker, 2001)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0448P)^2^+0.4661P] 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 3724 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1055 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.75456(5) 0.77614(4) 0.76749(3) 0.03738(15) Uani 1 1 d . . . C1 C 0.8857(5) 1.0762(4) 0.8705(3) 0.0517(10) Uani 1 1 d . . . H1 H 0.9532 1.1023 0.8239 0.062 Uiso 1 1 calc R . . C2 C 0.7017(6) 0.9575(4) 0.9455(3) 0.0644(12) Uani 1 1 d . . . H2 H 0.6174 0.8841 0.9618 0.077 Uiso 1 1 calc R . . C3 C 0.7739(6) 1.0878(5) 0.9992(3) 0.0723(14) Uani 1 1 d . . . H3 H 0.7473 1.1211 1.0580 0.087 Uiso 1 1 calc R . . C4 C 1.0122(5) 1.3048(4) 0.9852(3) 0.0634(12) Uani 1 1 d . . . H4A H 1.1024 1.3177 0.9462 0.076 Uiso 1 1 calc R . . H4B H 1.0626 1.3073 1.0509 0.076 Uiso 1 1 calc R . . C5 C 0.9340(4) 1.4275(4) 0.9812(3) 0.0453(9) Uani 1 1 d . . . H5A H 0.8431 1.4155 1.0197 0.054 Uiso 1 1 calc R . . H5B H 0.8861 1.4278 0.9156 0.054 Uiso 1 1 calc R . . C6 C 0.4718(4) 0.6273(4) 0.6151(2) 0.0416(8) Uani 1 1 d . . . H6 H 0.4407 0.5534 0.6517 0.050 Uiso 1 1 calc R . . C7 C 0.6024(5) 0.8228(4) 0.5688(3) 0.0513(10) Uani 1 1 d . . . H7 H 0.6805 0.9106 0.5672 0.062 Uiso 1 1 calc R . . C8 C 0.4704(5) 0.7559(4) 0.4993(3) 0.0548(10) Uani 1 1 d . . . H8 H 0.4408 0.7887 0.4422 0.066 Uiso 1 1 calc R . . C9 C 0.2307(4) 0.5254(4) 0.4827(3) 0.0493(10) Uani 1 1 d . . . H9A H 0.2368 0.4282 0.4920 0.059 Uiso 1 1 calc R . . H9B H 0.2165 0.5291 0.4144 0.059 Uiso 1 1 calc R . . C10 C 0.0811(4) 0.5563(4) 0.5232(2) 0.0437(9) Uani 1 1 d . . . H10A H 0.0726 0.6522 0.5121 0.052 Uiso 1 1 calc R . . H10B H 0.0966 0.5554 0.5919 0.052 Uiso 1 1 calc R . . C11 C 1.0679(4) 0.8707(4) 0.7162(3) 0.0430(9) Uani 1 1 d . . . C12 C 1.2538(4) 0.8854(4) 0.7121(3) 0.0511(10) Uani 1 1 d . . . H12A H 1.3022 0.8544 0.7691 0.061 Uiso 1 1 calc R . . H12B H 1.2637 0.8198 0.6572 0.061 Uiso 1 1 calc R . . C13 C 1.3570(5) 1.0368(4) 0.7052(3) 0.0544(10) Uani 1 1 d . . . H13A H 1.4683 1.0322 0.6918 0.065 Uiso 1 1 calc R . . H13B H 1.3030 1.0718 0.6517 0.065 Uiso 1 1 calc R . . C14 C 1.3768(5) 1.1434(4) 0.7947(3) 0.0515(10) Uani 1 1 d . . . H14A H 1.4448 1.1161 0.8462 0.062 Uiso 1 1 calc R . . H14B H 1.2662 1.1383 0.8132 0.062 Uiso 1 1 calc R . . C15 C 1.4588(5) 1.2976(4) 0.7819(3) 0.0582(11) Uani 1 1 d . . . H15A H 1.3925 1.3228 0.7287 0.070 Uiso 1 1 calc R . . H15B H 1.5703 1.3023 0.7649 0.070 Uiso 1 1 calc R . . C16 C 1.4766(5) 1.4095(4) 0.8690(3) 0.0475(9) Uani 1 1 d . . . H16A H 1.5556 1.3935 0.9201 0.057 Uiso 1 1 calc R . . H16B H 1.3679 1.3983 0.8912 0.057 Uiso 1 1 calc R . . C17 C 1.5388(5) 1.5623(4) 0.8466(2) 0.0443(9) Uani 1 1 d . . . N1 N 0.7717(3) 0.9500(3) 0.8633(2) 0.0406(7) Uani 1 1 d . . . N2 N 0.8922(4) 1.1609(3) 0.9518(2) 0.0470(8) Uani 1 1 d . . . N3 N 0.6031(3) 0.7418(3) 0.6411(2) 0.0398(7) Uani 1 1 d . . . N4 N 0.3899(3) 0.6315(3) 0.5294(2) 0.0427(7) Uani 1 1 d . . . O1 O 0.9917(3) 0.7699(3) 0.75909(18) 0.0473(6) Uani 1 1 d . . . O1W O 1.1064(4) 0.5149(3) 0.7751(2) 0.0766(9) Uani 1 1 d . . . H1WA H 1.0674 0.5889 0.7799 0.092 Uiso 1 1 d R . . H1WB H 1.2084 0.5465 0.8026 0.092 Uiso 1 1 d R . . O2 O 0.9947(3) 0.9516(3) 0.6779(2) 0.0611(7) Uani 1 1 d . . . O2W O 0.8856(7) 0.2515(5) 0.6741(4) 0.181(3) Uani 1 1 d . . . H2WA H 0.9576 0.3292 0.7017 0.217 Uiso 1 1 d R . . H2WB H 0.9339 0.2375 0.6255 0.217 Uiso 1 1 d R . . O3 O 1.4473(4) 1.6458(3) 0.8506(2) 0.0670(8) Uani 1 1 d . . . O3W O 0.9996(13) 0.1142(9) 0.5352(6) 0.136(3) Uani 0.50 1 d P . . H3WA H 0.9995 0.0492 0.5711 0.163 Uiso 0.50 1 d PR . . H3WB H 1.0022 0.0781 0.4780 0.163 Uiso 0.50 1 d PR . . O4 O 1.6838(3) 1.5935(3) 0.81995(19) 0.0519(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0309(2) 0.0334(2) 0.0422(2) -0.00096(17) 0.00103(16) 0.00301(16) C1 0.052(2) 0.038(2) 0.062(3) -0.0019(19) 0.021(2) 0.0048(18) C2 0.082(3) 0.047(2) 0.054(2) 0.000(2) 0.029(2) -0.008(2) C3 0.108(4) 0.048(3) 0.047(2) -0.009(2) 0.026(3) -0.005(2) C4 0.051(2) 0.037(2) 0.088(3) -0.009(2) -0.008(2) 0.0018(18) C5 0.046(2) 0.035(2) 0.048(2) -0.0002(16) 0.0019(17) 0.0046(16) C6 0.037(2) 0.044(2) 0.040(2) 0.0025(16) 0.0029(16) 0.0072(16) C7 0.042(2) 0.056(2) 0.051(2) 0.011(2) 0.0079(18) 0.0016(18) C8 0.049(2) 0.068(3) 0.044(2) 0.015(2) 0.0087(19) 0.007(2) C9 0.0341(19) 0.055(2) 0.048(2) -0.0101(18) -0.0017(17) 0.0025(17) C10 0.0354(19) 0.047(2) 0.038(2) -0.0052(16) -0.0017(16) -0.0008(16) C11 0.038(2) 0.039(2) 0.044(2) -0.0050(17) 0.0048(17) 0.0002(17) C12 0.038(2) 0.037(2) 0.071(3) -0.0069(18) 0.0178(19) -0.0001(16) C13 0.044(2) 0.044(2) 0.068(3) -0.0031(19) 0.022(2) -0.0032(18) C14 0.053(2) 0.035(2) 0.060(2) 0.0034(18) 0.0125(19) -0.0011(17) C15 0.065(3) 0.041(2) 0.061(3) 0.0009(19) 0.018(2) -0.0024(19) C16 0.043(2) 0.039(2) 0.055(2) 0.0049(17) 0.0087(18) 0.0001(16) C17 0.039(2) 0.041(2) 0.041(2) 0.0004(16) -0.0016(16) -0.0047(17) N1 0.0406(16) 0.0297(15) 0.0454(17) 0.0004(13) 0.0056(13) 0.0006(13) N2 0.0469(18) 0.0307(16) 0.0543(19) -0.0059(14) -0.0011(15) 0.0028(14) N3 0.0326(15) 0.0411(17) 0.0411(16) -0.0009(14) 0.0033(13) 0.0056(13) N4 0.0323(15) 0.0498(19) 0.0395(17) -0.0023(14) 0.0017(13) 0.0046(13) O1 0.0340(13) 0.0436(15) 0.0614(16) 0.0076(13) 0.0106(12) 0.0037(11) O1W 0.072(2) 0.076(2) 0.084(2) 0.0115(18) 0.0056(17) 0.0257(17) O2 0.0474(16) 0.0660(19) 0.0695(18) 0.0193(16) 0.0059(14) 0.0115(14) O2W 0.220(6) 0.128(4) 0.155(4) 0.058(4) -0.052(4) -0.005(4) O3 0.0533(17) 0.0484(17) 0.099(2) 0.0107(16) 0.0131(16) 0.0121(14) O3W 0.220(10) 0.122(7) 0.105(6) 0.056(6) 0.058(6) 0.085(7) O4 0.0379(14) 0.0407(14) 0.0711(18) 0.0134(13) 0.0067(13) -0.0022(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O4 1.965(2) 1_445 Y Zn1 O1 1.990(2) . Y Zn1 N1 1.995(3) . Y Zn1 N3 2.007(3) . Y C1 N2 1.321(4) . ? C1 N1 1.322(4) . ? C1 H1 0.9300 . ? C2 C3 1.346(5) . ? C2 N1 1.363(5) . ? C2 H2 0.9300 . ? C3 N2 1.348(5) . ? C3 H3 0.9300 . ? C4 N2 1.476(4) . ? C4 C5 1.481(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C5 1.533(6) 2_787 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N3 1.321(4) . ? C6 N4 1.331(4) . ? C6 H6 0.9300 . ? C7 C8 1.354(5) . ? C7 N3 1.357(5) . ? C7 H7 0.9300 . ? C8 N4 1.356(5) . ? C8 H8 0.9300 . ? C9 N4 1.477(4) . ? C9 C10 1.500(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C10 1.520(6) 2_566 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O2 1.232(4) . ? C11 O1 1.275(4) . ? C11 C12 1.515(5) . ? C12 C13 1.512(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.504(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.509(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.511(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.512(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 O3 1.232(4) . ? C17 O4 1.272(4) . ? O1W H1WA 0.8500 . ? O1W H1WB 0.8500 . ? O2W H2WA 0.8500 . ? O2W H2WB 0.8500 . ? O3W H3WA 0.8500 . ? O3W H3WB 0.8499 . ? O4 Zn1 1.965(2) 1_665 ? 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 O4 Zn1 O1 96.99(10) 1_445 . Y O4 Zn1 N1 112.27(11) 1_445 . Y O1 Zn1 N1 105.66(11) . . Y O4 Zn1 N3 104.14(11) 1_445 . Y O1 Zn1 N3 115.15(11) . . Y N1 Zn1 N3 120.27(12) . . Y N2 C1 N1 112.0(3) . . ? N2 C1 H1 124.0 . . ? N1 C1 H1 124.0 . . ? C3 C2 N1 109.2(4) . . ? C3 C2 H2 125.4 . . ? N1 C2 H2 125.4 . . ? C2 C3 N2 107.1(4) . . ? C2 C3 H3 126.4 . . ? N2 C3 H3 126.4 . . ? N2 C4 C5 113.8(3) . . ? N2 C4 H4A 108.8 . . ? C5 C4 H4A 108.8 . . ? N2 C4 H4B 108.8 . . ? C5 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C4 C5 C5 110.6(4) . 2_787 ? C4 C5 H5A 109.5 . . ? C5 C5 H5A 109.5 2_787 . ? C4 C5 H5B 109.5 . . ? C5 C5 H5B 109.5 2_787 . ? H5A C5 H5B 108.1 . . ? N3 C6 N4 111.1(3) . . ? N3 C6 H6 124.5 . . ? N4 C6 H6 124.5 . . ? C8 C7 N3 109.4(3) . . ? C8 C7 H7 125.3 . . ? N3 C7 H7 125.3 . . ? C7 C8 N4 106.3(3) . . ? C7 C8 H8 126.8 . . ? N4 C8 H8 126.8 . . ? N4 C9 C10 111.3(3) . . ? N4 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? N4 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C9 C10 C10 110.7(4) . 2_566 ? C9 C10 H10A 109.5 . . ? C10 C10 H10A 109.5 2_566 . ? C9 C10 H10B 109.5 . . ? C10 C10 H10B 109.5 2_566 . ? H10A C10 H10B 108.1 . . ? O2 C11 O1 122.3(3) . . ? O2 C11 C12 120.8(3) . . ? O1 C11 C12 116.9(3) . . ? C13 C12 C11 114.9(3) . . ? C13 C12 H12A 108.5 . . ? C11 C12 H12A 108.5 . . ? C13 C12 H12B 108.5 . . ? C11 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? C14 C13 C12 113.5(3) . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C13 C14 C15 112.7(3) . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C14 C15 C16 114.8(3) . . ? C14 C15 H15A 108.6 . . ? C16 C15 H15A 108.6 . . ? C14 C15 H15B 108.6 . . ? C16 C15 H15B 108.6 . . ? H15A C15 H15B 107.6 . . ? C15 C16 C17 111.4(3) . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? O3 C17 O4 123.9(4) . . ? O3 C17 C16 120.1(3) . . ? O4 C17 C16 115.9(3) . . ? C1 N1 C2 104.8(3) . . ? C1 N1 Zn1 124.9(3) . . ? C2 N1 Zn1 128.8(2) . . ? C1 N2 C3 106.8(3) . . ? C1 N2 C4 126.0(4) . . ? C3 N2 C4 127.1(3) . . ? C6 N3 C7 105.8(3) . . ? C6 N3 Zn1 122.7(3) . . ? C7 N3 Zn1 131.5(2) . . ? C6 N4 C8 107.4(3) . . ? C6 N4 C9 124.7(3) . . ? C8 N4 C9 127.6(3) . . ? C11 O1 Zn1 111.7(2) . . ? H1WA O1W H1WB 104.4 . . ? H2WA O2W H2WB 97.5 . . ? H3WA O3W H3WB 108.8 . . ? C17 O4 Zn1 117.9(2) . 1_665 ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.522 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 932567' ####################################################################### # # 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_p5 #TrackingRef 'web_deposit_cif_file_0_DiSun_1365081280.p1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 N2 O5 S Zn' _chemical_formula_weight 348.65 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbcn ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.664(5) _cell_length_b 11.683(5) _cell_length_c 19.847(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2704.7(19) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2648 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 27.12 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.712 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 1.990 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7545 _exptl_absorpt_correction_T_max 0.8258 _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 APEX II CCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10054 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2373 _reflns_number_gt 1867 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT+ ver. (Bruker, 2001)' _computing_data_reduction 'SAINT+ ver. (Bruker, 2001)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0784P)^2^+0.3742P] 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 2373 _refine_ls_number_parameters 199 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1196 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.014 _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 0.06721(4) 0.31231(3) 0.407370(19) 0.0330(2) Uani 1 1 d . . . S1 S -0.18304(8) 0.51354(8) 0.26177(4) 0.0376(3) Uani 1 1 d . . . C1 C -0.0234(3) 0.2557(4) 0.54374(18) 0.0463(10) Uani 1 1 d . . . H1 H -0.0694 0.3206 0.5458 0.056 Uiso 1 1 calc R . . C2 C 0.0652(11) 0.1156(13) 0.5056(8) 0.059(3) Uani 0.50 1 d PU . . H2A H 0.1048 0.0654 0.4752 0.071 Uiso 0.50 1 d PR . . C2A C 0.1126(12) 0.1459(13) 0.5133(8) 0.056(3) Uani 0.50 1 d PU . . H2AA H 0.1751 0.1152 0.4874 0.067 Uiso 0.50 1 d PR . . C3 C 0.0308(11) 0.0892(12) 0.5677(7) 0.062(3) Uani 0.50 1 d PU . . H3A H 0.0369 0.0159 0.5893 0.075 Uiso 0.50 1 d PR . . C3A C 0.0869(10) 0.1162(12) 0.5752(7) 0.057(3) Uani 0.50 1 d PU . . H3AA H 0.1264 0.0620 0.6032 0.068 Uiso 0.50 1 d PR . . C4 C -0.0618(4) 0.1892(5) 0.6612(2) 0.0649(15) Uani 1 1 d . . . H4A H -0.1137 0.1251 0.6672 0.078 Uiso 1 1 calc R . . H4B H -0.1063 0.2590 0.6649 0.078 Uiso 1 1 calc R . . C5 C 0.0246(4) 0.1871(4) 0.7152(2) 0.0513(11) Uani 1 1 d . . . H5A H 0.0740 0.2533 0.7103 0.062 Uiso 1 1 calc R . . H5B H 0.0717 0.1193 0.7098 0.062 Uiso 1 1 calc R . . C6 C -0.1163(3) 0.4696(3) 0.39262(18) 0.0352(8) Uani 1 1 d . . . C7 C -0.1896(3) 0.5382(3) 0.34675(16) 0.0333(8) Uani 1 1 d . . . C8 C -0.2639(3) 0.6236(3) 0.36224(17) 0.0422(9) Uani 1 1 d . . . H8 H -0.2776 0.6490 0.4059 0.051 Uiso 1 1 calc R . . C9 C -0.3178(3) 0.6692(3) 0.30494(18) 0.0401(9) Uani 1 1 d . . . H9 H -0.3716 0.7279 0.3066 0.048 Uiso 1 1 calc R . . C10 C -0.2827(3) 0.6184(3) 0.24667(17) 0.0328(8) Uani 1 1 d . . . C11 C -0.3164(3) 0.6483(3) 0.17732(18) 0.0370(8) Uani 1 1 d . . . N1 N 0.0360(3) 0.2273(3) 0.49089(15) 0.0400(8) Uani 1 1 d . . . N2 N -0.0118(3) 0.1832(3) 0.59388(15) 0.0474(9) Uani 1 1 d . . . O1 O -0.0475(2) 0.4026(2) 0.36271(13) 0.0463(7) Uani 1 1 d . . . O1W O 0.1944(2) 0.4149(2) 0.43653(13) 0.0478(7) Uani 1 1 d . . . H1WB H 0.1842 0.4329 0.4776 0.057 Uiso 1 1 d R . . H1WA H 0.1945 0.4762 0.4122 0.072 Uiso 1 1 d R . . O2 O -0.1247(3) 0.4770(2) 0.45402(12) 0.0523(8) Uani 1 1 d . . . O3 O -0.2770(3) 0.5941(3) 0.12937(14) 0.0732(10) Uani 1 1 d . . . O4 O -0.3820(3) 0.7332(2) 0.17212(12) 0.0482(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0386(3) 0.0333(3) 0.0270(3) 0.00078(16) 0.00037(16) 0.00806(18) S1 0.0462(6) 0.0362(5) 0.0306(5) -0.0027(4) -0.0050(4) 0.0152(4) C1 0.049(2) 0.058(3) 0.032(2) 0.0090(19) 0.0013(17) 0.021(2) C2 0.083(8) 0.044(6) 0.050(5) 0.009(5) 0.021(6) 0.022(6) C2A 0.069(8) 0.053(7) 0.046(5) 0.007(5) 0.015(6) 0.023(6) C3 0.086(8) 0.050(6) 0.051(5) 0.014(4) 0.021(6) 0.017(6) C3A 0.071(8) 0.057(6) 0.042(4) 0.014(4) 0.008(6) 0.032(6) C4 0.048(3) 0.114(5) 0.032(2) 0.015(2) 0.0084(18) 0.010(3) C5 0.047(2) 0.068(3) 0.038(2) -0.0044(19) 0.0062(19) -0.008(2) C6 0.038(2) 0.031(2) 0.036(2) -0.0005(15) -0.0066(16) 0.0037(17) C7 0.039(2) 0.0310(19) 0.0304(18) 0.0023(14) 0.0018(15) 0.0033(16) C8 0.056(2) 0.042(2) 0.0282(19) 0.0020(16) 0.0051(17) 0.0151(19) C9 0.047(2) 0.035(2) 0.039(2) 0.0052(16) 0.0058(16) 0.0168(17) C10 0.034(2) 0.029(2) 0.0354(19) 0.0036(15) -0.0039(14) 0.0061(15) C11 0.037(2) 0.035(2) 0.039(2) 0.0025(16) -0.0037(16) 0.0020(17) N1 0.048(2) 0.0376(18) 0.0339(17) 0.0034(14) 0.0037(14) 0.0105(16) N2 0.052(2) 0.057(2) 0.0327(19) 0.0055(15) 0.0057(14) 0.0084(18) O1 0.0553(17) 0.0503(17) 0.0331(15) -0.0016(12) -0.0043(11) 0.0241(14) O1W 0.0567(17) 0.0485(16) 0.0383(15) -0.0034(12) 0.0024(12) -0.0085(14) O2 0.072(2) 0.0569(18) 0.0282(15) 0.0002(12) -0.0034(13) 0.0185(16) O3 0.107(3) 0.076(2) 0.0367(17) -0.0117(15) -0.0150(16) 0.050(2) O4 0.0585(18) 0.0481(16) 0.0380(15) 0.0070(12) -0.0023(12) 0.0219(15) _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 O1 1.920(2) . ? Zn1 O4 1.922(3) 6_656 ? Zn1 N1 1.966(3) . ? Zn1 O1W 1.993(3) . ? S1 C7 1.713(3) . ? S1 C10 1.715(3) . ? C1 N1 1.300(5) . ? C1 N2 1.314(5) . ? C2 C2A 0.674(17) . ? C2 C3 1.334(16) . ? C2 N1 1.380(15) . ? C2 C3A 1.40(2) . ? C2A C3A 1.312(15) . ? C2A N1 1.379(16) . ? C2A C3 1.59(2) . ? C3 C3A 0.741(15) . ? C3 N2 1.312(15) . ? C3A N2 1.440(13) . ? C4 N2 1.459(5) . ? C4 C5 1.472(6) . ? C5 C5 1.495(8) 3_556 ? C6 O2 1.226(4) . ? C6 O1 1.269(4) . ? C6 C7 1.484(5) . ? C7 C8 1.357(5) . ? C8 C9 1.405(5) . ? C9 C10 1.363(5) . ? C10 C11 1.474(5) . ? C11 O3 1.232(4) . ? C11 O4 1.257(4) . ? O4 Zn1 1.922(3) 6_566 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O4 95.74(11) . 6_656 ? O1 Zn1 N1 122.52(12) . . ? O4 Zn1 N1 120.40(13) 6_656 . ? O1 Zn1 O1W 108.81(12) . . ? O4 Zn1 O1W 107.34(12) 6_656 . ? N1 Zn1 O1W 101.34(13) . . ? C7 S1 C10 91.26(17) . . ? N1 C1 N2 113.0(4) . . ? C2A C2 C3 99(3) . . ? C2A C2 N1 76(2) . . ? C3 C2 N1 109.9(11) . . ? C2A C2 C3A 68(2) . . ? C3 C2 C3A 31.3(7) . . ? N1 C2 C3A 104.3(13) . . ? C2 C2A C3A 83(3) . . ? C2 C2A N1 76(2) . . ? C3A C2A N1 109.6(11) . . ? C2 C2A C3 56(2) . . ? C3A C2A C3 27.6(8) . . ? N1 C2A C3 96.8(11) . . ? C3A C3 N2 84(2) . . ? C3A C3 C2 80(2) . . ? N2 C3 C2 106.6(10) . . ? C3A C3 C2A 55.1(16) . . ? N2 C3 C2A 98.5(11) . . ? C2 C3 C2A 24.8(8) . . ? C3 C3A C2A 97(2) . . ? C3 C3A C2 69.1(18) . . ? C2A C3A C2 28.5(8) . . ? C3 C3A N2 65.0(18) . . ? C2A C3A N2 106.3(9) . . ? C2 C3A N2 96.4(11) . . ? N2 C4 C5 113.1(3) . . ? C4 C5 C5 114.2(5) . 3_556 ? O2 C6 O1 124.0(3) . . ? O2 C6 C7 121.7(3) . . ? O1 C6 C7 114.3(3) . . ? C8 C7 C6 128.8(3) . . ? C8 C7 S1 112.0(3) . . ? C6 C7 S1 119.2(3) . . ? C7 C8 C9 112.4(3) . . ? C10 C9 C8 112.8(3) . . ? C9 C10 C11 127.5(3) . . ? C9 C10 S1 111.5(3) . . ? C11 C10 S1 120.9(3) . . ? O3 C11 O4 124.7(3) . . ? O3 C11 C10 120.0(3) . . ? O4 C11 C10 115.2(3) . . ? C1 N1 C2A 105.2(7) . . ? C1 N1 C2 101.7(7) . . ? C2A N1 C2 28.3(7) . . ? C1 N1 Zn1 130.5(3) . . ? C2A N1 Zn1 120.0(7) . . ? C2 N1 Zn1 127.6(7) . . ? C3 N2 C1 106.2(7) . . ? C3 N2 C3A 30.8(7) . . ? C1 N2 C3A 103.8(6) . . ? C3 N2 C4 123.6(7) . . ? C1 N2 C4 128.4(4) . . ? C3A N2 C4 125.5(6) . . ? C6 O1 Zn1 124.3(2) . . ? C11 O4 Zn1 129.4(2) . 6_566 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.476 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.101 _database_code_depnum_ccdc_archive 'CCDC 932568' ####################################################################### # # 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_p6 #TrackingRef 'web_deposit_cif_file_0_DiSun_1365081280.p1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H28 N4 O6 Zn' _chemical_formula_weight 461.81 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 '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 9.8348(10) _cell_length_b 15.2564(17) _cell_length_c 13.8403(15) _cell_angle_alpha 90.00 _cell_angle_beta 95.714(2) _cell_angle_gamma 90.00 _cell_volume 2066.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2090 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 22.79 _exptl_crystal_description needle _exptl_crystal_colour Pale-yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 1.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8369 _exptl_absorpt_correction_T_max 0.8868 _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 APEX II CCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9921 _diffrn_reflns_av_R_equivalents 0.0609 _diffrn_reflns_av_sigmaI/netI 0.0806 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3630 _reflns_number_gt 2436 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT+ ver. (Bruker, 2001)' _computing_data_reduction 'SAINT+ ver. (Bruker, 2001)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.1053P)^2^+0.5475P] 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 3630 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0933 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.1840 _refine_ls_wR_factor_gt 0.1608 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 0.84968(6) 0.26705(4) 0.25160(4) 0.0383(3) Uani 1 1 d . . . C1 C 0.6100(5) 0.3588(4) 0.3291(4) 0.0434(13) Uani 1 1 d . . . H1 H 0.5764 0.3073 0.3536 0.052 Uiso 1 1 calc R . . C2 C 0.7341(5) 0.4507(4) 0.2620(4) 0.0436(13) Uani 1 1 d . . . H2 H 0.8045 0.4748 0.2305 0.052 Uiso 1 1 calc R . . C3 C 0.6293(6) 0.4943(4) 0.2883(4) 0.0487(14) Uani 1 1 d . . . H3 H 0.6124 0.5539 0.2795 0.058 Uiso 1 1 calc R . . N2 N 0.5497(4) 0.4356(3) 0.3310(3) 0.0430(11) Uani 1 1 d . . . C4 C 0.4259(5) 0.4557(5) 0.3751(4) 0.0586(17) Uani 1 1 d . . . H4A H 0.3859 0.4016 0.3960 0.070 Uiso 1 1 calc R . . H4B H 0.3606 0.4828 0.3271 0.070 Uiso 1 1 calc R . . C5 C 0.4525(6) 0.5165(6) 0.4614(5) 0.080(2) Uani 1 1 d . . . H5A H 0.4872 0.5717 0.4390 0.096 Uiso 1 1 calc R . . H5B H 0.3664 0.5286 0.4873 0.096 Uiso 1 1 calc R . . C6 C 0.6319(5) 0.1762(4) 0.1293(4) 0.0444(13) Uani 1 1 d . . . H6 H 0.5897 0.1597 0.1837 0.053 Uiso 1 1 calc R . . C7 C 0.7736(6) 0.2304(4) 0.0386(4) 0.0502(15) Uani 1 1 d . . . H7 H 0.8489 0.2590 0.0177 0.060 Uiso 1 1 calc R . . C8 C 0.6669(6) 0.1956(5) -0.0190(4) 0.0567(16) Uani 1 1 d . . . H8 H 0.6567 0.1950 -0.0865 0.068 Uiso 1 1 calc R . . C9 C 0.4495(6) 0.1213(4) 0.0090(5) 0.0627(18) Uani 1 1 d . . . H9A H 0.3985 0.1582 -0.0388 0.075 Uiso 1 1 calc R . . H9B H 0.3971 0.1163 0.0645 0.075 Uiso 1 1 calc R . . C10 C 0.4655(7) 0.0327(5) -0.0334(6) 0.075(2) Uani 1 1 d . . . H10A H 0.3756 0.0106 -0.0564 0.090 Uiso 1 1 calc R . . H10B H 0.5170 0.0384 -0.0893 0.090 Uiso 1 1 calc R . . C11 C 0.8090(5) 0.1457(4) 0.3888(3) 0.0368(12) Uani 1 1 d . . . C12 C 0.8445(5) 0.0840(4) 0.4726(4) 0.0386(12) Uani 1 1 d . . . H12 H 0.9108 0.0419 0.4516 0.046 Uiso 1 1 calc R . . C13 C 0.7234(6) 0.0313(4) 0.5007(4) 0.0507(15) Uani 1 1 d . . . H13A H 0.6755 0.0060 0.4427 0.061 Uiso 1 1 calc R . . H13B H 0.7564 -0.0164 0.5431 0.061 Uiso 1 1 calc R . . C14 C 0.6251(5) 0.0866(4) 0.5517(4) 0.0466(14) Uani 1 1 d . . . H14A H 0.5794 0.1272 0.5052 0.056 Uiso 1 1 calc R . . H14B H 0.5560 0.0488 0.5747 0.056 Uiso 1 1 calc R . . C15 C 0.6926(5) 0.1378(4) 0.6361(4) 0.0382(12) Uani 1 1 d . . . H15 H 0.7261 0.0960 0.6867 0.046 Uiso 1 1 calc R . . C16 C 0.8130(5) 0.1889(4) 0.6075(4) 0.0427(13) Uani 1 1 d . . . H16A H 0.8595 0.2164 0.6647 0.051 Uiso 1 1 calc R . . H16B H 0.7808 0.2350 0.5626 0.051 Uiso 1 1 calc R . . C17 C 0.9135(5) 0.1311(4) 0.5600(4) 0.0465(14) Uani 1 1 d . . . H17A H 0.9874 0.1669 0.5402 0.056 Uiso 1 1 calc R . . H17B H 0.9525 0.0884 0.6068 0.056 Uiso 1 1 calc R . . C18 C 0.5858(5) 0.1949(4) 0.6763(4) 0.0458(14) Uani 1 1 d . . . N1 N 0.7251(4) 0.3648(3) 0.2874(3) 0.0420(11) Uani 1 1 d . . . N3 N 0.7491(4) 0.2155(3) 0.1334(3) 0.0410(11) Uani 1 1 d . . . N4 N 0.5793(4) 0.1624(3) 0.0393(3) 0.0455(11) Uani 1 1 d . . . O1 O 0.9085(3) 0.1892(3) 0.3598(3) 0.0454(9) Uani 1 1 d . . . O1W O 0.6613(5) 0.3860(4) 0.8026(5) 0.0979(18) Uani 1 1 d . . . H1WA H 0.5926 0.3735 0.8327 0.117 Uiso 1 1 d R . . H1WB H 0.6554 0.3562 0.7505 0.117 Uiso 1 1 d R . . O2 O 0.6939(4) 0.1526(3) 0.3492(3) 0.0568(11) Uani 1 1 d . . . O2W O 0.9149(7) 0.3070(7) 0.8391(7) 0.197(5) Uani 1 1 d . . . H2WA H 0.8585 0.3479 0.8231 0.236 Uiso 1 1 d R . . H2WB H 0.9907 0.3333 0.8373 0.236 Uiso 1 1 d R . . O3 O 0.5789(5) 0.2746(3) 0.6561(4) 0.0687(13) Uani 1 1 d . . . O4 O 0.5029(4) 0.1578(3) 0.7250(3) 0.0604(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 Zn1 0.0389(4) 0.0450(4) 0.0314(4) -0.0028(3) 0.0060(2) -0.0020(3) C1 0.049(3) 0.044(4) 0.037(3) -0.003(3) 0.008(2) -0.007(3) C2 0.049(3) 0.049(4) 0.034(3) 0.005(3) 0.010(2) -0.007(3) C3 0.061(3) 0.043(4) 0.043(3) 0.009(3) 0.010(3) 0.001(3) N2 0.045(2) 0.049(3) 0.036(2) -0.002(2) 0.0087(19) 0.002(2) C4 0.035(3) 0.090(5) 0.053(4) -0.015(4) 0.014(3) 0.002(3) C5 0.052(4) 0.125(7) 0.065(5) -0.016(5) 0.017(3) 0.018(4) C6 0.046(3) 0.049(4) 0.037(3) 0.003(3) 0.000(2) 0.001(3) C7 0.054(3) 0.062(4) 0.036(3) -0.002(3) 0.013(3) 0.003(3) C8 0.062(4) 0.075(5) 0.031(3) -0.005(3) -0.005(3) 0.012(3) C9 0.053(3) 0.051(4) 0.078(5) -0.007(4) -0.025(3) 0.000(3) C10 0.064(4) 0.058(5) 0.094(6) -0.007(4) -0.034(4) 0.001(3) C11 0.044(3) 0.042(3) 0.027(3) -0.002(2) 0.015(2) 0.001(2) C12 0.043(3) 0.041(3) 0.033(3) 0.002(2) 0.010(2) 0.010(2) C13 0.062(3) 0.045(4) 0.047(3) -0.008(3) 0.017(3) -0.007(3) C14 0.043(3) 0.060(4) 0.039(3) -0.006(3) 0.013(2) -0.015(3) C15 0.036(3) 0.048(4) 0.032(3) 0.001(2) 0.007(2) 0.002(2) C16 0.039(3) 0.054(4) 0.034(3) -0.005(3) 0.000(2) -0.001(2) C17 0.036(3) 0.067(4) 0.036(3) 0.003(3) 0.001(2) 0.000(3) C18 0.047(3) 0.055(4) 0.037(3) -0.004(3) 0.011(2) -0.003(3) N1 0.039(2) 0.051(3) 0.037(2) -0.001(2) 0.0106(18) -0.005(2) N3 0.045(3) 0.046(3) 0.032(2) -0.001(2) 0.0032(19) 0.001(2) N4 0.048(3) 0.042(3) 0.043(3) -0.002(2) -0.008(2) 0.004(2) O1 0.0420(19) 0.054(3) 0.041(2) 0.0031(19) 0.0077(16) -0.0058(18) O1W 0.073(3) 0.094(4) 0.127(5) -0.025(4) 0.011(3) -0.011(3) O2 0.039(2) 0.085(3) 0.045(2) 0.015(2) 0.0005(17) -0.002(2) O2W 0.091(5) 0.243(11) 0.252(11) -0.130(10) -0.009(6) 0.026(6) O3 0.066(3) 0.059(3) 0.082(4) 0.008(3) 0.016(2) 0.008(2) O4 0.052(2) 0.072(3) 0.061(3) 0.004(2) 0.024(2) 0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.954(4) . Y Zn1 O4 1.958(4) 4_665 Y Zn1 N3 1.987(4) . Y Zn1 N1 2.022(4) . Y C1 N2 1.315(7) . ? C1 N1 1.324(6) . ? C1 H1 0.9300 . ? C2 C3 1.310(7) . ? C2 N1 1.362(7) . ? C2 H2 0.9300 . ? C3 N2 1.363(7) . ? C3 H3 0.9300 . ? N2 C4 1.448(6) . ? C4 C5 1.515(9) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C5 1.438(14) 3_666 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N3 1.296(7) . ? C6 N4 1.318(7) . ? C6 H6 0.9300 . ? C7 C8 1.361(8) . ? C7 N3 1.376(7) . ? C7 H7 0.9300 . ? C8 N4 1.337(8) . ? C8 H8 0.9300 . ? C9 N4 1.447(7) . ? C9 C10 1.488(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C10 1.478(13) 3_655 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O2 1.212(6) . ? C11 O1 1.278(6) . ? C11 C12 1.508(7) . ? C12 C17 1.508(7) . ? C12 C13 1.519(7) . ? C12 H12 0.9800 . ? C13 C14 1.510(7) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.504(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.503(7) . ? C15 C18 1.512(7) . ? C15 H15 0.9800 . ? C16 C17 1.522(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 O4 1.245(7) . ? C18 O3 1.248(7) . ? O1W H1WA 0.8500 . ? O1W H1WB 0.8500 . ? O2W H2WA 0.8500 . ? O2W H2WB 0.8500 . ? O4 Zn1 1.958(4) 4_566 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O4 109.02(17) . 4_665 Y O1 Zn1 N3 118.40(18) . . Y O4 Zn1 N3 113.97(18) 4_665 . Y O1 Zn1 N1 113.61(17) . . Y O4 Zn1 N1 96.34(18) 4_665 . Y N3 Zn1 N1 103.26(17) . . Y N2 C1 N1 110.8(5) . . ? N2 C1 H1 124.6 . . ? N1 C1 H1 124.6 . . ? C3 C2 N1 110.1(5) . . ? C3 C2 H2 124.9 . . ? N1 C2 H2 124.9 . . ? C2 C3 N2 106.8(5) . . ? C2 C3 H3 126.6 . . ? N2 C3 H3 126.6 . . ? C1 N2 C3 107.3(4) . . ? C1 N2 C4 126.7(5) . . ? C3 N2 C4 126.0(5) . . ? N2 C4 C5 112.0(5) . . ? N2 C4 H4A 109.2 . . ? C5 C4 H4A 109.2 . . ? N2 C4 H4B 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C5 C5 C4 114.8(9) 3_666 . ? C5 C5 H5A 108.6 3_666 . ? C4 C5 H5A 108.6 . . ? C5 C5 H5B 108.6 3_666 . ? C4 C5 H5B 108.6 . . ? H5A C5 H5B 107.5 . . ? N3 C6 N4 112.3(5) . . ? N3 C6 H6 123.9 . . ? N4 C6 H6 123.9 . . ? C8 C7 N3 107.2(5) . . ? C8 C7 H7 126.4 . . ? N3 C7 H7 126.4 . . ? N4 C8 C7 107.5(5) . . ? N4 C8 H8 126.3 . . ? C7 C8 H8 126.3 . . ? N4 C9 C10 112.6(5) . . ? N4 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? N4 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C10 C10 C9 115.2(8) 3_655 . ? C10 C10 H10A 108.5 3_655 . ? C9 C10 H10A 108.5 . . ? C10 C10 H10B 108.5 3_655 . ? C9 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? O2 C11 O1 121.5(5) . . ? O2 C11 C12 122.4(5) . . ? O1 C11 C12 116.0(4) . . ? C17 C12 C11 111.8(5) . . ? C17 C12 C13 110.4(4) . . ? C11 C12 C13 113.6(4) . . ? C17 C12 H12 106.9 . . ? C11 C12 H12 106.9 . . ? C13 C12 H12 106.9 . . ? C14 C13 C12 112.3(5) . . ? C14 C13 H13A 109.2 . . ? C12 C13 H13A 109.2 . . ? C14 C13 H13B 109.2 . . ? C12 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C15 C14 C13 113.6(4) . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? C13 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C16 C15 C14 111.3(4) . . ? C16 C15 C18 113.1(5) . . ? C14 C15 C18 108.5(4) . . ? C16 C15 H15 108.0 . . ? C14 C15 H15 108.0 . . ? C18 C15 H15 108.0 . . ? C15 C16 C17 112.1(5) . . ? C15 C16 H16A 109.2 . . ? C17 C16 H16A 109.2 . . ? C15 C16 H16B 109.2 . . ? C17 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C12 C17 C16 111.2(4) . . ? C12 C17 H17A 109.4 . . ? C16 C17 H17A 109.4 . . ? C12 C17 H17B 109.4 . . ? C16 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? O4 C18 O3 122.7(5) . . ? O4 C18 C15 117.0(6) . . ? O3 C18 C15 120.2(5) . . ? C1 N1 C2 105.0(5) . . ? C1 N1 Zn1 128.4(4) . . ? C2 N1 Zn1 126.1(3) . . ? C6 N3 C7 105.9(5) . . ? C6 N3 Zn1 125.9(4) . . ? C7 N3 Zn1 126.8(4) . . ? C6 N4 C8 107.1(5) . . ? C6 N4 C9 126.6(5) . . ? C8 N4 C9 126.3(5) . . ? C11 O1 Zn1 112.2(3) . . ? H1WA O1W H1WB 107.8 . . ? H2WA O2W H2WB 101.4 . . ? C18 O4 Zn1 113.2(4) . 4_566 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.294 _refine_diff_density_min -0.850 _refine_diff_density_rms 0.101 _database_code_depnum_ccdc_archive 'CCDC 932569' ####################################################################### # # 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_p7 #TrackingRef 'web_deposit_cif_file_0_DiSun_1365081280.p1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 N4 O4 Zn' _chemical_formula_weight 447.79 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 7.984(2) _cell_length_b 8.729(2) _cell_length_c 16.898(4) _cell_angle_alpha 93.577(4) _cell_angle_beta 95.508(5) _cell_angle_gamma 103.030(4) _cell_volume 1137.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 1319 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 23.04 _exptl_crystal_description block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 1.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8512 _exptl_absorpt_correction_T_max 0.9165 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 APEX II CCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5658 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0802 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3972 _reflns_number_gt 2928 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT+ ver. (Bruker, 2001)' _computing_data_reduction 'SAINT+ ver. (Bruker, 2001)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0523P)^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 3972 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0659 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 0.946 _refine_ls_restrained_S_all 0.946 _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 0.82609(6) 0.74709(5) 0.69778(3) 0.02602(16) Uani 1 1 d . . . C1 C 1.1152(4) 0.6237(4) 0.6377(2) 0.0253(8) Uani 1 1 d . . . H1 H 1.1404 0.5832 0.6872 0.030 Uiso 1 1 calc R . . C2 C 0.9972(5) 0.7344(4) 0.5458(2) 0.0265(8) Uani 1 1 d . . . H2 H 0.9228 0.7886 0.5177 0.032 Uiso 1 1 calc R . . C3 C 1.1264(5) 0.6820(4) 0.5155(2) 0.0280(9) Uani 1 1 d . . . H3 H 1.1585 0.6912 0.4630 0.034 Uiso 1 1 calc R . . C4 C 1.3427(5) 0.5298(5) 0.5735(2) 0.0292(9) Uani 1 1 d . . . H4A H 1.2949 0.4160 0.5778 0.035 Uiso 1 1 calc R . . H4B H 1.4289 0.5702 0.6205 0.035 Uiso 1 1 calc R . . C5 C 1.4315(4) 0.5485(4) 0.4996(2) 0.0261(8) Uani 1 1 d . . . H5A H 1.4868 0.6612 0.4966 0.031 Uiso 1 1 calc R . . H5B H 1.3456 0.5129 0.4521 0.031 Uiso 1 1 calc R . . C6 C 1.1368(5) 0.9044(4) 0.8073(2) 0.0336(10) Uani 1 1 d . . . H6 H 1.2091 0.8597 0.7758 0.040 Uiso 1 1 calc R . . C7 C 0.9145(6) 0.9654(5) 0.8500(2) 0.0426(11) Uani 1 1 d . . . H7 H 0.7986 0.9724 0.8541 0.051 Uiso 1 1 calc R . . C8 C 1.0544(6) 1.0409(5) 0.9005(2) 0.0482(12) Uani 1 1 d . . . H8 H 1.0545 1.1081 0.9469 0.058 Uiso 1 1 calc R . . C9 C 1.3718(5) 1.0532(5) 0.9081(2) 0.0444(11) Uani 1 1 d . . . H9A H 1.4006 1.1690 0.9208 0.053 Uiso 1 1 calc R . . H9B H 1.4487 1.0286 0.8689 0.053 Uiso 1 1 calc R . . C10 C 1.4054(5) 0.9748(5) 0.9830(2) 0.0404(11) Uani 1 1 d . . . H10A H 1.3729 0.8587 0.9710 0.048 Uiso 1 1 calc R . . H10B H 1.3327 1.0030 1.0233 0.048 Uiso 1 1 calc R . . C11 C 0.6126(5) 0.9519(4) 0.6718(2) 0.0313(9) Uani 1 1 d . . . C12 C 0.5742(5) 1.0948(4) 0.6338(2) 0.0309(9) Uani 1 1 d . . . H12A H 0.6790 1.1822 0.6439 0.037 Uiso 1 1 calc R . . H12B H 0.5498 1.0689 0.5754 0.037 Uiso 1 1 calc R . . C13 C 0.4255(5) 1.1512(4) 0.6630(2) 0.0269(9) Uani 1 1 d . . . C14 C 0.2634(5) 1.0949(4) 0.6213(2) 0.0352(10) Uani 1 1 d . . . H14 H 0.2515 1.0263 0.5742 0.042 Uiso 1 1 calc R . . C15 C 0.1191(5) 1.1353(5) 0.6460(3) 0.0431(11) Uani 1 1 d . . . H15 H 0.0086 1.0931 0.6170 0.052 Uiso 1 1 calc R . . C16 C 0.1358(6) 1.2359(5) 0.7121(3) 0.0498(13) Uani 1 1 d . . . H16 H 0.0368 1.2654 0.7295 0.060 Uiso 1 1 calc R . . C17 C 0.2961(6) 1.2954(5) 0.7543(3) 0.0417(11) Uani 1 1 d . . . H17 H 0.3064 1.3673 0.8000 0.050 Uiso 1 1 calc R . . C18 C 0.4437(5) 1.2530(4) 0.7316(2) 0.0303(9) Uani 1 1 d . . . C19 C 0.6149(5) 1.3156(4) 0.7801(2) 0.0387(10) Uani 1 1 d . . . H19A H 0.6781 1.2302 0.7814 0.046 Uiso 1 1 calc R . . H19B H 0.5942 1.3424 0.8355 0.046 Uiso 1 1 calc R . . C20 C 0.7310(5) 1.4597(4) 0.7515(2) 0.0308(9) Uani 1 1 d . . . N1 N 0.9898(4) 0.6974(3) 0.62265(16) 0.0239(7) Uani 1 1 d . . . N2 N 1.2016(4) 0.6133(3) 0.57500(16) 0.0225(7) Uani 1 1 d . . . N3 N 0.9679(4) 0.8771(3) 0.79164(17) 0.0289(7) Uani 1 1 d . . . N4 N 1.1942(4) 1.0026(4) 0.87266(18) 0.0334(8) Uani 1 1 d . . . O1 O 0.7096(3) 0.8820(3) 0.63461(15) 0.0335(6) Uani 1 1 d . . . O2 O 0.5561(4) 0.9144(4) 0.73390(18) 0.0565(9) Uani 1 1 d . . . O3 O 0.6584(3) 1.5601(3) 0.72144(16) 0.0357(7) Uani 1 1 d . . . O4 O 0.8889(4) 1.4784(3) 0.76197(18) 0.0500(8) 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 Zn1 0.0203(3) 0.0218(2) 0.0381(3) 0.00100(18) 0.00948(19) 0.00713(17) C1 0.021(2) 0.029(2) 0.029(2) 0.0012(16) 0.0052(16) 0.0136(17) C2 0.022(2) 0.029(2) 0.031(2) 0.0031(17) 0.0025(16) 0.0105(17) C3 0.031(2) 0.033(2) 0.023(2) 0.0097(17) 0.0081(17) 0.0108(18) C4 0.025(2) 0.038(2) 0.032(2) 0.0067(18) 0.0128(17) 0.0187(18) C5 0.019(2) 0.028(2) 0.034(2) 0.0042(17) 0.0102(17) 0.0091(16) C6 0.035(3) 0.033(2) 0.033(2) -0.0061(18) 0.0073(19) 0.0062(19) C7 0.042(3) 0.049(3) 0.039(3) -0.005(2) 0.020(2) 0.011(2) C8 0.057(3) 0.051(3) 0.032(2) -0.016(2) 0.018(2) 0.004(2) C9 0.038(3) 0.045(3) 0.037(2) -0.008(2) 0.008(2) -0.015(2) C10 0.044(3) 0.041(2) 0.030(2) -0.0030(19) 0.0047(19) -0.002(2) C11 0.024(2) 0.029(2) 0.043(3) 0.0045(19) 0.0077(19) 0.0093(17) C12 0.032(2) 0.029(2) 0.038(2) 0.0091(18) 0.0148(18) 0.0138(18) C13 0.025(2) 0.0196(19) 0.040(2) 0.0105(17) 0.0094(18) 0.0085(16) C14 0.033(3) 0.027(2) 0.047(3) 0.0098(19) 0.003(2) 0.0093(19) C15 0.024(2) 0.034(2) 0.072(3) 0.020(2) 0.005(2) 0.0029(19) C16 0.027(3) 0.036(3) 0.099(4) 0.032(3) 0.032(3) 0.018(2) C17 0.053(3) 0.025(2) 0.054(3) 0.007(2) 0.030(2) 0.012(2) C18 0.032(2) 0.0186(19) 0.043(2) 0.0079(17) 0.0121(19) 0.0066(17) C19 0.042(3) 0.027(2) 0.043(2) 0.0054(19) 0.002(2) 0.0013(19) C20 0.031(2) 0.025(2) 0.038(2) 0.0010(17) 0.0076(18) 0.0095(18) N1 0.0215(18) 0.0228(16) 0.0290(18) 0.0039(13) 0.0046(13) 0.0074(13) N2 0.0181(17) 0.0239(16) 0.0268(17) -0.0014(13) 0.0046(13) 0.0075(13) N3 0.027(2) 0.0278(17) 0.0329(18) 0.0040(14) 0.0110(15) 0.0056(15) N4 0.036(2) 0.0317(18) 0.0273(18) -0.0011(15) 0.0088(16) -0.0045(15) O1 0.0264(16) 0.0298(15) 0.0496(17) 0.0037(12) 0.0115(13) 0.0146(12) O2 0.066(2) 0.063(2) 0.064(2) 0.0374(18) 0.0368(18) 0.0446(18) O3 0.0268(16) 0.0249(14) 0.0558(18) 0.0150(13) 0.0057(13) 0.0036(12) O4 0.0317(19) 0.0465(18) 0.080(2) 0.0236(16) 0.0216(16) 0.0161(15) _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 O3 1.953(2) 1_545 y Zn1 O1 1.962(2) . y Zn1 N3 1.984(3) . y Zn1 N1 2.004(3) . y C1 N1 1.320(4) . ? C1 N2 1.328(4) . ? C2 C3 1.349(5) . ? C2 N1 1.362(4) . ? C3 N2 1.361(4) . ? C4 N2 1.475(4) . ? C4 C5 1.493(5) . ? C5 C5 1.526(6) 2_866 ? C6 N3 1.313(5) . ? C6 N4 1.332(4) . ? C7 C8 1.351(6) . ? C7 N3 1.372(4) . ? C8 N4 1.352(5) . ? C9 N4 1.444(5) . ? C9 C10 1.507(6) . ? C10 C10 1.518(8) 2_877 ? C11 O2 1.217(4) . ? C11 O1 1.275(4) . ? C11 C12 1.515(5) . ? C12 C13 1.497(5) . ? C13 C14 1.381(5) . ? C13 C18 1.391(5) . ? C14 C15 1.372(5) . ? C15 C16 1.354(6) . ? C16 C17 1.377(6) . ? C17 C18 1.392(5) . ? C18 C19 1.494(5) . ? C19 C20 1.519(5) . ? C20 O4 1.228(4) . ? C20 O3 1.261(4) . ? O3 Zn1 1.953(2) 1_565 ? 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 O3 Zn1 O1 110.30(11) 1_545 . y O3 Zn1 N3 115.72(12) 1_545 . y O1 Zn1 N3 108.82(12) . . y O3 Zn1 N1 113.04(11) 1_545 . y O1 Zn1 N1 100.62(11) . . y N3 Zn1 N1 107.22(12) . . y N1 C1 N2 111.6(3) . . ? C3 C2 N1 109.5(3) . . ? C2 C3 N2 106.5(3) . . ? N2 C4 C5 113.2(3) . . ? C4 C5 C5 110.0(4) . 2_866 ? N3 C6 N4 111.6(3) . . ? C8 C7 N3 108.6(4) . . ? C7 C8 N4 107.2(4) . . ? N4 C9 C10 112.5(3) . . ? C9 C10 C10 111.2(4) . 2_877 ? O2 C11 O1 125.1(4) . . ? O2 C11 C12 120.3(3) . . ? O1 C11 C12 114.6(3) . . ? C13 C12 C11 114.8(3) . . ? C14 C13 C18 119.2(3) . . ? C14 C13 C12 118.2(3) . . ? C18 C13 C12 122.5(3) . . ? C15 C14 C13 121.9(4) . . ? C16 C15 C14 119.3(4) . . ? C15 C16 C17 120.0(4) . . ? C16 C17 C18 121.7(4) . . ? C13 C18 C17 117.8(4) . . ? C13 C18 C19 121.8(3) . . ? C17 C18 C19 120.4(4) . . ? C18 C19 C20 116.1(3) . . ? O4 C20 O3 122.7(4) . . ? O4 C20 C19 119.9(4) . . ? O3 C20 C19 117.2(4) . . ? C1 N1 C2 105.4(3) . . ? C1 N1 Zn1 127.2(2) . . ? C2 N1 Zn1 127.4(2) . . ? C1 N2 C3 107.0(3) . . ? C1 N2 C4 123.3(3) . . ? C3 N2 C4 129.5(3) . . ? C6 N3 C7 105.7(3) . . ? C6 N3 Zn1 126.1(3) . . ? C7 N3 Zn1 128.1(3) . . ? C6 N4 C8 107.0(4) . . ? C6 N4 C9 126.0(3) . . ? C8 N4 C9 127.0(3) . . ? C11 O1 Zn1 115.4(2) . . ? C20 O3 Zn1 112.0(2) . 1_565 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.449 _refine_diff_density_min -0.473 _refine_diff_density_rms 0.078 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 _platon_squeeze_void_content 1 0.016 0.500 0.000 222 78 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 932570' ####################################################################### # # 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_p8 #TrackingRef 'web_deposit_cif_file_0_DiSun_1365081280.p1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 N4 O4 S Zn' _chemical_formula_weight 403.75 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M c2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 35.840(3) _cell_length_b 9.0465(8) _cell_length_c 12.2671(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.468(2) _cell_angle_gamma 90.00 _cell_volume 3977.2(6) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3116 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 24.63 _exptl_crystal_description block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 1.362 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8217 _exptl_absorpt_correction_T_max 0.8758 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9304 _diffrn_reflns_av_R_equivalents 0.1032 _diffrn_reflns_av_sigmaI/netI 0.0794 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3496 _reflns_number_gt 2385 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT+ ver. (Bruker, 2001)' _computing_data_reduction 'SAINT+ ver. (Bruker, 2001)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.1361P)^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 3496 _refine_ls_number_parameters 253 _refine_ls_number_restraints 66 _refine_ls_R_factor_all 0.1018 _refine_ls_R_factor_gt 0.0776 _refine_ls_wR_factor_ref 0.2452 _refine_ls_wR_factor_gt 0.2323 _refine_ls_goodness_of_fit_ref 1.158 _refine_ls_restrained_S_all 1.153 _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 0.13914(2) -0.09687(9) 1.09453(6) 0.0521(3) Uani 1 1 d . . . S1 S 0.15825(6) 0.3937(2) 0.9081(2) 0.0814(7) Uani 1 1 d . . . C1 C 0.1946(2) -0.0668(8) 1.2821(6) 0.0610(18) Uani 1 1 d . . . H1 H 0.1776 -0.0138 1.3235 0.073 Uiso 1 1 calc R . . C2 C 0.2195(2) -0.1893(9) 1.1501(6) 0.072(2) Uani 1 1 d . . . H2 H 0.2232 -0.2340 1.0827 0.086 Uiso 1 1 calc R . . C3 C 0.2456(2) -0.1816(12) 1.2361(7) 0.089(3) Uani 1 1 d . . . H3 H 0.2692 -0.2244 1.2378 0.106 Uiso 1 1 calc R . . C4 C 0.2471(3) -0.0617(8) 1.4239(7) 0.080(3) Uani 1 1 d . . . H4A H 0.2368 0.0316 1.4484 0.095 Uiso 1 1 calc R . . H4B H 0.2737 -0.0475 1.4136 0.095 Uiso 1 1 calc R . . C5 C 0.24171(18) -0.1739(7) 1.5114(6) 0.0610(18) Uani 1 1 d . . . H5A H 0.2527 -0.1363 1.5784 0.073 Uiso 1 1 calc R . . H5B H 0.2152 -0.1853 1.5235 0.073 Uiso 1 1 calc R . . C6 C 0.0866(2) -0.0550(10) 1.2826(7) 0.076(2) Uani 1 1 d . . . H6 H 0.0968 0.0371 1.2987 0.092 Uiso 1 1 calc R . . C7 C 0.0753(2) -0.2590(8) 1.2055(6) 0.0644(18) Uani 1 1 d . . . H7 H 0.0773 -0.3388 1.1581 0.077 Uiso 1 1 calc R . . C8 C 0.0511(2) -0.2553(9) 1.2915(6) 0.071(2) Uani 1 1 d . . . H8 H 0.0330 -0.3239 1.3103 0.085 Uiso 1 1 calc R . . C9 C 0.0458(3) -0.0728(14) 1.4477(8) 0.117(4) Uani 1 1 d . . . H9A H 0.0481 -0.1513 1.5012 0.140 Uiso 1 1 calc R . . H9B H 0.0607 0.0101 1.4730 0.140 Uiso 1 1 calc R . . C10 C 0.0074(3) -0.0278(13) 1.4400(9) 0.105(3) Uani 1 1 d . . . H10A H -0.0077 -0.1101 1.4147 0.127 Uiso 1 1 calc R . . H10B H 0.0050 0.0520 1.3876 0.127 Uiso 1 1 calc R . . C11 C 0.1317(3) 0.2060(9) 1.0700(7) 0.080(2) Uani 1 1 d . . . C12 C 0.1263(3) 0.3582(10) 1.0157(7) 0.084(2) Uani 1 1 d . . . H12A H 0.1291 0.4345 1.0708 0.101 Uiso 1 1 calc R . . H12B H 0.1011 0.3645 0.9870 0.101 Uiso 1 1 calc R . . C13 C 0.1407(3) 0.5657(8) 0.8509(6) 0.076(2) Uani 1 1 d . . . H13A H 0.1140 0.5602 0.8440 0.091 Uiso 1 1 d R . . H13B H 0.1508 0.5813 0.7796 0.091 Uiso 1 1 d R . . C14 C 0.1513(6) 0.6957(19) 0.9252(12) 0.056(4) Uani 0.50 1 d PU . . C14A C 0.1231(8) 0.695(3) 0.9402(19) 0.077(5) Uani 0.50 1 d PU . . N1 N 0.18724(15) -0.1180(6) 1.1836(4) 0.0533(14) Uani 1 1 d . . . N2 N 0.22978(16) -0.0998(6) 1.3165(5) 0.0594(15) Uani 1 1 d . . . N3 N 0.09562(14) -0.1369(6) 1.1970(4) 0.0521(13) Uani 1 1 d . . . N4 N 0.06036(19) -0.1248(9) 1.3433(6) 0.086(2) Uani 1 1 d . . . O1 O 0.13688(15) 0.0941(5) 1.0110(4) 0.0677(14) Uani 1 1 d . . . O2 O 0.1430(8) 0.193(3) 1.169(2) 0.122(10) Uani 0.50 1 d PU . . O2A O 0.1198(7) 0.206(2) 1.1627(17) 0.105(7) Uani 0.50 1 d PU . . O3 O 0.1259(5) 0.7342(16) 0.9920(13) 0.064(3) Uani 0.50 1 d PU . . O3A O 0.0893(5) 0.7191(17) 0.9449(11) 0.119(5) Uani 0.50 1 d PU . . O4A O 0.1487(6) 0.762(2) 0.9818(16) 0.102(5) Uani 0.50 1 d PU . . O4 O 0.1835(3) 0.7589(13) 0.9192(8) 0.074(3) Uani 0.50 1 d PU . . 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 0.0652(6) 0.0524(5) 0.0387(5) 0.0050(3) -0.0022(3) 0.0038(3) S1 0.0883(14) 0.0656(13) 0.0905(15) 0.0266(11) 0.0088(12) 0.0126(10) C1 0.074(4) 0.059(4) 0.050(4) -0.007(3) -0.002(3) 0.021(3) C2 0.088(5) 0.081(6) 0.047(4) 0.003(4) 0.003(4) 0.034(4) C3 0.068(5) 0.126(8) 0.071(5) 0.023(5) 0.008(4) 0.039(5) C4 0.116(7) 0.046(4) 0.076(5) 0.010(4) -0.043(5) -0.016(4) C5 0.062(4) 0.056(4) 0.065(4) -0.013(4) -0.023(3) 0.009(3) C6 0.082(5) 0.085(6) 0.062(5) -0.012(4) 0.008(4) -0.011(4) C7 0.075(4) 0.051(4) 0.067(4) -0.004(4) 0.002(4) 0.006(4) C8 0.074(5) 0.073(5) 0.065(5) -0.004(4) 0.013(4) -0.010(4) C9 0.118(9) 0.159(11) 0.074(6) -0.031(7) 0.026(6) -0.006(7) C10 0.099(7) 0.106(8) 0.112(8) -0.034(7) 0.014(6) -0.017(6) C11 0.131(7) 0.050(5) 0.059(5) -0.002(4) -0.004(5) -0.021(5) C12 0.118(7) 0.074(5) 0.060(5) -0.003(4) 0.015(5) 0.027(5) C13 0.129(7) 0.048(4) 0.050(4) 0.001(3) -0.014(4) 0.010(4) C14 0.089(11) 0.057(9) 0.020(6) 0.009(6) -0.006(7) -0.001(9) C14A 0.095(14) 0.087(13) 0.048(10) 0.009(9) -0.020(12) 0.009(12) N1 0.064(3) 0.049(3) 0.046(3) 0.009(2) -0.005(3) 0.003(2) N2 0.068(3) 0.049(3) 0.062(3) 0.011(3) -0.014(3) -0.003(3) N3 0.057(3) 0.055(3) 0.044(3) -0.003(3) 0.004(2) 0.003(3) N4 0.076(4) 0.110(6) 0.071(4) -0.025(4) 0.025(4) -0.021(4) O1 0.097(4) 0.053(3) 0.053(3) 0.017(2) -0.005(3) 0.009(3) O2 0.25(3) 0.059(9) 0.061(9) -0.004(7) -0.035(16) 0.049(16) O2A 0.23(2) 0.050(10) 0.040(8) 0.000(6) 0.016(13) -0.011(14) O3 0.070(8) 0.075(8) 0.047(7) -0.019(6) 0.004(8) -0.012(6) O3A 0.150(11) 0.129(11) 0.077(8) -0.016(8) -0.027(8) 0.062(10) O4A 0.133(12) 0.106(10) 0.068(9) -0.015(9) -0.029(10) -0.025(11) O4 0.073(6) 0.088(7) 0.061(6) -0.024(6) 0.017(5) -0.020(6) _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 O1 2.010(4) . y Zn1 O3 2.033(16) 1_545 y Zn1 N3 2.043(5) . y Zn1 N1 2.043(5) . y S1 C12 1.784(9) . ? S1 C13 1.817(7) . ? C1 N1 1.318(8) . ? C1 N2 1.360(9) . ? C1 H1 0.9300 . ? C2 C3 1.407(10) . ? C2 N1 1.390(9) . ? C2 H2 0.9300 . ? C3 N2 1.361(10) . ? C3 H3 0.9300 . ? C4 N2 1.492(9) . ? C4 C5 1.492(11) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C5 1.526(13) 7_548 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N3 1.327(10) . ? C6 N4 1.360(11) . ? C6 H6 0.9300 . ? C7 N3 1.328(9) . ? C7 C8 1.371(10) . ? C7 H7 0.9300 . ? C8 N4 1.379(10) . ? C8 H8 0.9300 . ? C9 C10 1.435(14) . ? C9 N4 1.465(11) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C10 1.65(2) 5_558 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O2A 1.22(2) . ? C11 O1 1.259(9) . ? C11 O2 1.28(2) . ? C11 C12 1.541(12) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.53(2) . ? C13 C14A 1.72(3) . ? C13 H13A 0.9602 . ? C13 H13B 0.9600 . ? C14 O4A 0.920(19) . ? C14 C14A 1.03(3) . ? C14 O4 1.29(2) . ? C14 O3 1.28(3) . ? C14A O3 0.735(19) . ? C14A O3A 1.23(3) . ? C14A O4A 1.21(3) . ? O2 O2A 0.84(3) . ? O3 O4A 0.862(17) . ? O3 O3A 1.43(2) . ? O3 Zn1 2.033(16) 1_565 ? O4A O4 1.47(3) . ? O4A Zn1 1.92(2) 1_565 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O3 108.8(5) . 1_545 y O1 Zn1 N3 116.0(2) . . y O3 Zn1 N3 94.1(5) 1_545 . y O1 Zn1 N1 112.6(2) . . y O3 Zn1 N1 116.9(5) 1_545 . y N3 Zn1 N1 107.4(2) . . y C12 S1 C13 102.5(4) . . ? N1 C1 N2 112.6(6) . . ? N1 C1 H1 123.7 . . ? N2 C1 H1 123.7 . . ? C3 C2 N1 107.8(6) . . ? C3 C2 H2 126.1 . . ? N1 C2 H2 126.1 . . ? N2 C3 C2 107.0(6) . . ? N2 C3 H3 126.5 . . ? C2 C3 H3 126.5 . . ? N2 C4 C5 115.0(6) . . ? N2 C4 H4A 108.5 . . ? C5 C4 H4A 108.5 . . ? N2 C4 H4B 108.5 . . ? C5 C4 H4B 108.5 . . ? H4A C4 H4B 107.5 . . ? C5 C5 C4 115.4(8) 7_548 . ? C5 C5 H5A 108.4 7_548 . ? C4 C5 H5A 108.4 . . ? C5 C5 H5B 108.4 7_548 . ? C4 C5 H5B 108.4 . . ? H5A C5 H5B 107.5 . . ? N3 C6 N4 110.4(7) . . ? N3 C6 H6 124.8 . . ? N4 C6 H6 124.8 . . ? N3 C7 C8 113.0(7) . . ? N3 C7 H7 123.5 . . ? C8 C7 H7 123.5 . . ? N4 C8 C7 103.0(7) . . ? N4 C8 H8 128.5 . . ? C7 C8 H8 128.5 . . ? C10 C9 N4 112.4(10) . . ? C10 C9 H9A 109.1 . . ? N4 C9 H9A 109.1 . . ? C10 C9 H9B 109.1 . . ? N4 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C9 C10 C10 110.1(11) . 5_558 ? C9 C10 H10A 109.6 . . ? C10 C10 H10A 109.6 5_558 . ? C9 C10 H10B 109.6 . . ? C10 C10 H10B 109.6 5_558 . ? H10A C10 H10B 108.2 . . ? O2A C11 O1 126.2(13) . . ? O2A C11 O2 39.3(16) . . ? O1 C11 O2 114.9(13) . . ? O2A C11 C12 111.2(13) . . ? O1 C11 C12 119.2(7) . . ? O2 C11 C12 122.1(14) . . ? C11 C12 S1 113.7(6) . . ? C11 C12 H12A 108.8 . . ? S1 C12 H12A 108.8 . . ? C11 C12 H12B 108.8 . . ? S1 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C14 C13 S1 110.1(7) . . ? C14 C13 C14A 36.3(9) . . ? S1 C13 C14A 117.5(8) . . ? C14 C13 H13A 109.6 . . ? S1 C13 H13A 109.4 . . ? C14A C13 H13A 73.9 . . ? C14 C13 H13B 109.6 . . ? S1 C13 H13B 110.2 . . ? C14A C13 H13B 128.5 . . ? H13A C13 H13B 108.0 . . ? O4A C14 C14A 76(2) . . ? O4A C14 O4 82(3) . . ? C14A C14 O4 153(3) . . ? O4A C14 O3 42.4(14) . . ? C14A C14 O3 35.1(13) . . ? O4 C14 O3 124(2) . . ? O4A C14 C13 157(3) . . ? C14A C14 C13 82(2) . . ? O4 C14 C13 121.6(14) . . ? O3 C14 C13 114(2) . . ? O3 C14A C14 91(3) . . ? O3 C14A O3A 90(4) . . ? C14 C14A O3A 167(3) . . ? O3 C14A O4A 45(2) . . ? C14 C14A O4A 47.8(16) . . ? O3A C14A O4A 129(3) . . ? O3 C14A C13 146(4) . . ? C14 C14A C13 62(2) . . ? O3A C14A C13 121.0(19) . . ? O4A C14A C13 109(3) . . ? C1 N1 C2 105.9(6) . . ? C1 N1 Zn1 128.2(5) . . ? C2 N1 Zn1 125.9(5) . . ? C1 N2 C3 106.6(6) . . ? C1 N2 C4 127.0(7) . . ? C3 N2 C4 126.3(7) . . ? C6 N3 C7 105.4(6) . . ? C6 N3 Zn1 125.4(5) . . ? C7 N3 Zn1 128.1(5) . . ? C6 N4 C8 108.0(7) . . ? C6 N4 C9 125.6(8) . . ? C8 N4 C9 126.3(8) . . ? C11 O1 Zn1 113.8(5) . . ? O2A O2 C11 66(3) . . ? O2 O2A C11 74(3) . . ? C14A O3 O4A 98(4) . . ? C14A O3 C14 54(3) . . ? O4A O3 C14 46.0(16) . . ? C14A O3 O3A 59(3) . . ? O4A O3 O3A 146(2) . . ? C14 O3 O3A 111.7(18) . . ? C14A O3 Zn1 158(3) . 1_565 ? O4A O3 Zn1 70(2) . 1_565 ? C14 O3 Zn1 116.0(17) . 1_565 ? O3A O3 Zn1 121.9(10) . 1_565 ? C14A O3A O3 30.8(11) . . ? C14 O4A O3 92(2) . . ? C14 O4A C14A 55.9(16) . . ? O3 O4A C14A 37.1(17) . . ? C14 O4A O4 60(2) . . ? O3 O4A O4 151(3) . . ? C14A O4A O4 115(3) . . ? C14 O4A Zn1 175(3) . 1_565 ? O3 O4A Zn1 85(2) . 1_565 ? C14A O4A Zn1 120(3) . 1_565 ? O4 O4A Zn1 123.0(11) . 1_565 ? C14 O4 O4A 38.2(8) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.796 _refine_diff_density_min -0.727 _refine_diff_density_rms 0.104 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 _platon_squeeze_void_content 1 0.500 0.000 -0.006 265 64 ' ' 2 0.000 0.500 0.239 265 64 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 932571'