# Electronic Supplementary Material (ESI) for CrystEngComm # 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_09ssg003 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H28 N8 O10 Zn2' _chemical_formula_weight 791.34 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.3395(2) _cell_length_b 15.7388(4) _cell_length_c 12.6940(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.5650(10) _cell_angle_gamma 90.00 _cell_volume 1605.03(8) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7002 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 26.60 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.637 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 1.566 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.833870 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0537 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 20916 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 26.72 _reflns_number_total 6182 _reflns_number_gt 5590 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The Flack parameter value obatined from the crystal structure refinement is 0.365(11). This value may be arised from the presence of 'Noncrystallographic Inversion', as detected in the Addsym check in the Platon softwarre. ; _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^)+(0.0367P)^2^+1.0268P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.365(11) _refine_ls_number_reflns 6182 _refine_ls_number_parameters 535 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0813 _refine_ls_wR_factor_gt 0.0782 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.59726(5) 0.04662(3) 0.49430(3) 0.03370(12) Uani 1 1 d . . . O1 O 0.6653(3) 0.0545(2) 0.35795(19) 0.0402(7) Uani 1 1 d . . . N1 N 0.4963(4) 0.1541(2) 0.5335(2) 0.0352(8) Uani 1 1 d . . . C1 C 0.4821(5) 0.1887(3) 0.6266(3) 0.0357(9) Uani 1 1 d . . . H1B H 0.5246 0.1648 0.6954 0.043 Uiso 1 1 calc R . . O1W O 0.4243(5) 0.3555(4) 0.1554(3) 0.122(3) Uani 1 1 d D . . H1WB H 0.3480 0.3482 0.1999 0.183 Uiso 1 1 d D . . H1WA H 0.4653 0.3006 0.1483 0.183 Uiso 1 1 d D . . N2 N 0.4184(4) 0.2081(3) 0.4548(3) 0.0382(9) Uani 1 1 d . . . H222 H 0.413(5) 0.199(3) 0.396(3) 0.040(13) Uiso 1 1 d . . . C2 C 0.3955(5) 0.2651(3) 0.6074(3) 0.0352(9) Uani 1 1 d . . . O2 O 0.4591(4) 0.1380(3) 0.2703(2) 0.0732(13) Uani 1 1 d . . . O2W O 0.1003(4) 0.0505(3) 0.3708(3) 0.0690(10) Uani 1 1 d D . . H2WB H 0.1431 0.0144 0.3216 0.103 Uiso 1 1 d D . . H2WA H 0.0973 0.1057 0.3407 0.103 Uiso 1 1 d D . . C3 C 0.3570(5) 0.2746(3) 0.4957(3) 0.0380(10) Uani 1 1 d . . . H3 H 0.297(5) 0.312(4) 0.452(3) 0.042(12) Uiso 1 1 d . . . N3 N 0.7005(4) 0.3392(2) 0.9368(2) 0.0364(9) Uani 1 1 d . . . O3 O 0.9172(4) -0.0812(2) -0.0414(2) 0.0456(8) Uani 1 1 d . . . C4 C 0.6382(5) 0.3365(3) 0.8280(3) 0.0373(10) Uani 1 1 d D . . H4 H 0.711(4) 0.345(3) 0.785(3) 0.043(12) Uiso 1 1 d D . . N4 N 0.5666(4) 0.3322(3) 0.9764(3) 0.0358(8) Uani 1 1 d . . . H444 H 0.580(5) 0.331(3) 1.039(3) 0.035(11) Uiso 1 1 d . . . O4 O 0.9782(4) -0.1071(2) 0.1356(3) 0.0551(9) Uani 1 1 d . . . C5 C 0.4667(4) 0.3277(3) 0.7980(3) 0.0341(8) Uani 1 1 d . . . C6 C 0.4267(5) 0.3254(4) 0.8968(3) 0.0367(9) Uani 1 1 d . . . H6 H 0.328(5) 0.318(3) 0.907(3) 0.034(10) Uiso 1 1 d . . . C7 C 0.3478(5) 0.3257(4) 0.6858(3) 0.0438(10) Uani 1 1 d . . . H7B H 0.3396 0.3825 0.6550 0.053 Uiso 1 1 calc R . . H7A H 0.2384 0.3101 0.6925 0.053 Uiso 1 1 calc R . . C8 C 0.6391(5) 0.0829(3) 0.1712(3) 0.0319(8) Uani 1 1 d . . . C9 C 0.5712(5) 0.1351(3) 0.0822(3) 0.0361(9) Uani 1 1 d . . . H9 H 0.505(5) 0.172(3) 0.091(3) 0.038(12) Uiso 1 1 d . . . C10 C 0.6164(6) 0.1233(3) -0.0144(3) 0.0413(10) Uani 1 1 d . . . H10 H 0.577(5) 0.158(3) -0.075(3) 0.037(11) Uiso 1 1 d . . . C11 C 0.7238(5) 0.0591(3) -0.0227(3) 0.0387(10) Uani 1 1 d . . . H11 H 0.748(5) 0.050(3) -0.083(3) 0.044(11) Uiso 1 1 d . . . C12 C 0.7931(5) 0.0070(3) 0.0657(3) 0.0330(9) Uani 1 1 d . . . C13 C 0.7515(5) 0.0206(3) 0.1638(3) 0.0318(9) Uani 1 1 d . . . H13 H 0.797(5) -0.008(3) 0.219(3) 0.024(10) Uiso 1 1 d . . . C14 C 0.5832(5) 0.0934(3) 0.2739(3) 0.0366(9) Uani 1 1 d . . . C15 C 0.9068(5) -0.0653(3) 0.0555(4) 0.0379(10) Uani 1 1 d . . . O1A O 0.4305(4) -0.0441(2) 0.4662(3) 0.0474(8) Uani 1 1 d . . . C14A C 0.4115(6) -0.0680(3) 0.5600(4) 0.0391(10) Uani 1 1 d . . . O2A O 0.4933(4) -0.0372(2) 0.6466(3) 0.0525(9) Uani 1 1 d . . . C12A C 0.2819(5) -0.1346(3) 0.5559(3) 0.0338(9) Uani 1 1 d . . . C11A C 0.2143(5) -0.1807(4) 0.4609(3) 0.0413(9) Uani 1 1 d . . . C13A C 0.2302(5) -0.1514(3) 0.6487(3) 0.0308(9) Uani 1 1 d . . . C8A C 0.1117(4) -0.2136(3) 0.6474(3) 0.0302(8) Uani 1 1 d . . . C10A C 0.0988(6) -0.2438(3) 0.4598(4) 0.0443(11) Uani 1 1 d . . . H11A H 0.257(6) -0.166(4) 0.396(4) 0.066(15) Uiso 1 1 d . . . H13A H 0.278(4) -0.123(3) 0.716(3) 0.023(9) Uiso 1 1 d . . . C9A C 0.0466(5) -0.2592(3) 0.5522(3) 0.0371(9) Uani 1 1 d . . . H10A H 0.058(5) -0.269(3) 0.400(3) 0.038(12) Uiso 1 1 d . . . C15A C 0.0500(5) -0.2297(3) 0.7472(3) 0.0343(9) Uani 1 1 d . . . O3A O 0.1210(3) -0.1871(2) 0.83211(18) 0.0394(7) Uani 1 1 d . . . O4A O -0.0637(4) -0.2821(2) 0.7407(2) 0.0556(9) Uani 1 1 d . . . H9A H -0.035(5) -0.301(3) 0.546(3) 0.045(12) Uiso 1 1 d . . . N3A N 0.8290(4) 0.0274(2) 0.5887(2) 0.0366(8) Uani 1 1 d . . . C4A C 0.8933(5) 0.0255(3) 0.6975(3) 0.0398(11) Uani 1 1 d . . . N4A N 0.9615(4) 0.0414(3) 0.5495(3) 0.0376(8) Uani 1 1 d . . . H4A H 0.816(5) 0.023(3) 0.737(3) 0.048(13) Uiso 1 1 d . . . C5A C 1.0641(4) 0.0395(3) 0.7267(3) 0.0316(8) Uani 1 1 d . . . C6A C 1.1000(4) 0.0500(3) 0.6279(3) 0.0352(8) Uani 1 1 d . . . C7A C 1.1832(5) 0.0402(4) 0.8387(3) 0.0414(10) Uani 1 1 d . . . H6A H 1.208(5) 0.059(3) 0.617(3) 0.049(12) Uiso 1 1 d . . . C2A C 1.1376(5) 0.1011(3) 0.9183(3) 0.0332(9) Uani 1 1 d . . . H7D H 1.285(5) 0.060(3) 0.828(3) 0.045(12) Uiso 1 1 d . . . H7C H 1.186(5) -0.018(3) 0.869(4) 0.047(12) Uiso 1 1 d . . . C1A C 1.0564(5) 0.1790(3) 0.8987(3) 0.0383(10) Uani 1 1 d . . . C3A C 1.1724(5) 0.0900(3) 1.0294(3) 0.0397(10) Uani 1 1 d . . . N1A N 1.0414(4) 0.2130(2) 0.9925(3) 0.0351(8) Uani 1 1 d . . . H1A H 1.013(5) 0.206(3) 0.835(3) 0.031(10) Uiso 1 1 d . . . Zn1A Zn 0.93629(5) 0.32031(3) 1.02836(3) 0.03289(11) Uani 1 1 d . . . N2A N 1.1136(4) 0.1575(3) 1.0713(3) 0.0374(8) Uani 1 1 d . . . H22A H 1.102(7) 0.175(4) 1.134(5) 0.09(2) Uiso 1 1 d . . . H3A H 1.224(5) 0.044(4) 1.071(3) 0.051(12) Uiso 1 1 d . . . H44A H 0.950(5) 0.038(3) 0.494(3) 0.030(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0366(2) 0.0370(3) 0.03113(19) -0.0046(2) 0.01531(17) -0.0014(2) O1 0.0465(14) 0.0478(19) 0.0313(12) 0.0038(14) 0.0194(11) -0.0006(15) N1 0.0397(18) 0.034(2) 0.0335(16) -0.0042(14) 0.0136(14) -0.0022(16) C1 0.040(2) 0.039(3) 0.0303(18) -0.0035(17) 0.0123(17) 0.0029(19) O1W 0.061(2) 0.258(9) 0.047(2) -0.002(3) 0.0159(18) 0.042(3) N2 0.041(2) 0.047(3) 0.0296(17) -0.0062(16) 0.0146(15) -0.0018(17) C2 0.035(2) 0.039(3) 0.0315(18) -0.0067(17) 0.0091(16) -0.0019(18) O2 0.061(2) 0.127(4) 0.0344(15) -0.0079(19) 0.0175(15) 0.047(2) O2W 0.069(2) 0.086(3) 0.0623(18) 0.018(2) 0.0352(16) 0.014(2) C3 0.035(2) 0.041(3) 0.037(2) -0.0028(19) 0.0089(18) 0.002(2) N3 0.0375(17) 0.045(3) 0.0299(14) -0.0036(14) 0.0143(13) -0.0062(15) O3 0.0505(18) 0.043(2) 0.0509(17) -0.0063(15) 0.0269(15) 0.0099(15) C4 0.039(2) 0.045(3) 0.0320(17) -0.0045(17) 0.0177(16) -0.0063(19) N4 0.0395(16) 0.044(2) 0.0276(15) -0.0039(15) 0.0160(13) 0.0017(17) O4 0.0531(19) 0.062(3) 0.0575(19) 0.0123(17) 0.0268(16) 0.0233(17) C5 0.0368(18) 0.032(2) 0.0340(16) -0.0036(18) 0.0101(14) 0.0061(19) C6 0.0301(18) 0.041(3) 0.0437(19) -0.011(2) 0.0176(16) 0.003(2) C7 0.042(2) 0.051(3) 0.0369(18) -0.010(2) 0.0076(16) 0.016(2) C8 0.0354(19) 0.036(2) 0.0277(17) -0.0022(15) 0.0139(15) -0.0049(17) C9 0.037(2) 0.035(3) 0.042(2) -0.0025(18) 0.0201(17) 0.0062(19) C10 0.050(2) 0.043(3) 0.035(2) 0.0071(18) 0.0176(18) 0.007(2) C11 0.045(2) 0.044(3) 0.0339(18) 0.0004(19) 0.0219(17) -0.003(2) C12 0.0327(19) 0.032(2) 0.0399(19) -0.0037(17) 0.0199(16) -0.0054(17) C13 0.0320(18) 0.036(3) 0.0292(17) 0.0011(16) 0.0121(15) -0.0035(17) C14 0.036(2) 0.046(3) 0.0318(19) -0.0101(18) 0.0144(16) -0.0045(19) C15 0.034(2) 0.038(3) 0.049(2) 0.002(2) 0.0227(19) -0.0024(19) O1A 0.057(2) 0.046(2) 0.0485(17) -0.0016(14) 0.0309(15) -0.0096(15) C14A 0.040(2) 0.033(3) 0.051(2) 0.003(2) 0.024(2) 0.0045(19) O2A 0.0507(18) 0.060(2) 0.0494(18) -0.0023(15) 0.0177(15) -0.0188(16) C12A 0.035(2) 0.035(2) 0.0356(19) 0.0033(17) 0.0170(16) 0.0032(18) C11A 0.049(2) 0.047(3) 0.0363(17) 0.001(2) 0.0252(17) -0.002(2) C13A 0.0325(19) 0.029(2) 0.0319(18) 0.0011(15) 0.0112(15) 0.0063(15) C8A 0.0284(18) 0.034(2) 0.0314(17) -0.0002(15) 0.0139(14) 0.0000(16) C10A 0.047(2) 0.056(3) 0.035(2) -0.016(2) 0.0202(19) -0.011(2) C9A 0.039(2) 0.038(3) 0.038(2) -0.0015(17) 0.0163(17) -0.0047(19) C15A 0.0342(19) 0.041(3) 0.0302(18) 0.0056(17) 0.0133(15) 0.0055(18) O3A 0.0493(15) 0.0437(18) 0.0323(12) -0.0043(14) 0.0232(11) -0.0071(15) O4A 0.0557(18) 0.080(3) 0.0353(14) -0.0027(15) 0.0194(14) -0.0316(17) N3A 0.0365(16) 0.046(3) 0.0316(14) -0.0029(14) 0.0160(13) -0.0008(15) C4A 0.038(2) 0.052(3) 0.0320(17) -0.0054(18) 0.0143(16) -0.0012(19) N4A 0.0436(18) 0.046(2) 0.0286(16) 0.0069(18) 0.0185(14) 0.0055(19) C5A 0.0328(16) 0.027(2) 0.0371(17) -0.0057(18) 0.0133(14) 0.0049(18) C6A 0.0330(18) 0.034(2) 0.0422(18) 0.004(2) 0.0168(16) 0.003(2) C7A 0.037(2) 0.045(3) 0.0413(19) -0.008(2) 0.0107(17) 0.009(2) C2A 0.0282(18) 0.038(3) 0.0349(19) -0.0057(17) 0.0110(15) -0.0005(17) C1A 0.043(2) 0.042(3) 0.0305(19) -0.0007(18) 0.0118(18) 0.000(2) C3A 0.039(2) 0.042(3) 0.039(2) 0.000(2) 0.0120(18) 0.000(2) N1A 0.0436(19) 0.032(2) 0.0341(16) -0.0038(14) 0.0178(15) -0.0007(16) Zn1A 0.0363(2) 0.0356(3) 0.03104(19) -0.0032(2) 0.01631(16) -0.0029(2) N2A 0.0411(19) 0.041(2) 0.0320(16) -0.0053(15) 0.0138(15) 0.0004(17) _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 O1A 1.958(3) . ? Zn1 O1 1.965(2) . ? Zn1 N3A 2.005(3) . ? Zn1 N1 2.011(4) . ? O1 C14 1.261(5) . ? N1 C1 1.335(5) . ? N1 N2 1.339(5) . ? C1 C2 1.390(6) . ? C1 H1B 0.9300 . ? O1W H1WB 0.9645 . ? O1W H1WA 0.9434 . ? N2 C3 1.330(6) . ? N2 H222 0.74(4) . ? C2 C3 1.376(5) . ? C2 C7 1.506(6) . ? O2 C14 1.241(5) . ? O2W H2WB 0.9789 . ? O2W H2WA 0.9476 . ? C3 H3 0.88(5) . ? N3 C4 1.340(5) . ? N3 N4 1.347(4) . ? N3 Zn1A 2.020(3) . ? O3 C15 1.280(5) . ? O3 Zn1A 1.953(3) 2_746 ? C4 C5 1.385(5) . ? C4 H4 0.932(19) . ? N4 C6 1.327(5) . ? N4 H444 0.77(4) . ? O4 C15 1.223(5) . ? C5 C6 1.382(5) . ? C5 C7 1.502(5) . ? C6 H6 0.88(4) . ? C7 H7B 0.9700 . ? C7 H7A 0.9700 . ? C8 C13 1.377(6) . ? C8 C9 1.390(6) . ? C8 C14 1.506(5) . ? C9 C10 1.389(6) . ? C9 H9 0.83(4) . ? C10 C11 1.373(7) . ? C10 H10 0.93(4) . ? C11 C12 1.386(6) . ? C11 H11 0.86(4) . ? C12 C13 1.395(5) . ? C12 C15 1.509(6) . ? C13 H13 0.83(4) . ? O1A C14A 1.298(5) . ? C14A O2A 1.228(5) . ? C14A C12A 1.497(6) . ? C12A C13A 1.385(5) . ? C12A C11A 1.391(6) . ? C11A C10A 1.381(7) . ? C11A H11A 1.01(5) . ? C13A C8A 1.388(5) . ? C13A H13A 0.95(4) . ? C8A C9A 1.385(6) . ? C8A C15A 1.511(5) . ? C10A C9A 1.377(6) . ? C10A H10A 0.85(4) . ? C9A H9A 0.94(5) . ? C15A O4A 1.242(5) . ? C15A O3A 1.272(5) . ? O3A Zn1A 1.958(2) 2_647 ? N3A C4A 1.341(5) . ? N3A N4A 1.346(5) . ? C4A C5A 1.389(5) . ? C4A H4A 0.92(4) . ? N4A C6A 1.314(5) . ? N4A H44A 0.69(4) . ? C5A C6A 1.375(5) . ? C5A C7A 1.501(5) . ? C6A H6A 0.96(4) . ? C7A C2A 1.513(6) . ? C7A H7D 0.94(4) . ? C7A H7C 0.99(5) . ? C2A C3A 1.373(6) . ? C2A C1A 1.389(6) . ? C1A N1A 1.343(5) . ? C1A H1A 0.91(4) . ? C3A N2A 1.339(6) . ? C3A H3A 0.93(5) . ? N1A N2A 1.342(5) . ? N1A Zn1A 2.010(4) . ? Zn1A O3 1.953(3) 2_756 ? Zn1A O3A 1.958(2) 2_657 ? N2A H22A 0.88(6) . ? 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 O1A Zn1 O1 104.16(13) . . ? O1A Zn1 N3A 121.51(15) . . ? O1 Zn1 N3A 94.35(11) . . ? O1A Zn1 N1 109.52(14) . . ? O1 Zn1 N1 113.83(14) . . ? N3A Zn1 N1 112.32(14) . . ? C14 O1 Zn1 123.8(2) . . ? C1 N1 N2 105.2(3) . . ? C1 N1 Zn1 134.8(3) . . ? N2 N1 Zn1 120.0(2) . . ? N1 C1 C2 111.3(4) . . ? N1 C1 H1B 124.3 . . ? C2 C1 H1B 124.3 . . ? H1WB O1W H1WA 105.1 . . ? C3 N2 N1 111.6(3) . . ? C3 N2 H222 128(4) . . ? N1 N2 H222 121(4) . . ? C3 C2 C1 103.9(4) . . ? C3 C2 C7 125.6(4) . . ? C1 C2 C7 130.5(4) . . ? H2WB O2W H2WA 104.4 . . ? N2 C3 C2 108.0(4) . . ? N2 C3 H3 120(3) . . ? C2 C3 H3 132(3) . . ? C4 N3 N4 104.6(3) . . ? C4 N3 Zn1A 129.6(3) . . ? N4 N3 Zn1A 123.3(2) . . ? C15 O3 Zn1A 106.0(3) . 2_746 ? N3 C4 C5 111.9(3) . . ? N3 C4 H4 118(3) . . ? C5 C4 H4 130(2) . . ? C6 N4 N3 111.7(3) . . ? C6 N4 H444 129(3) . . ? N3 N4 H444 119(3) . . ? C6 C5 C4 103.6(3) . . ? C6 C5 C7 127.0(3) . . ? C4 C5 C7 129.3(3) . . ? N4 C6 C5 108.2(3) . . ? N4 C6 H6 125(2) . . ? C5 C6 H6 127(2) . . ? C5 C7 C2 114.6(3) . . ? C5 C7 H7B 108.6 . . ? C2 C7 H7B 108.6 . . ? C5 C7 H7A 108.6 . . ? C2 C7 H7A 108.6 . . ? H7B C7 H7A 107.6 . . ? C13 C8 C9 120.1(3) . . ? C13 C8 C14 120.8(4) . . ? C9 C8 C14 119.1(4) . . ? C8 C9 C10 119.4(4) . . ? C8 C9 H9 117(3) . . ? C10 C9 H9 124(3) . . ? C11 C10 C9 120.3(4) . . ? C11 C10 H10 117(3) . . ? C9 C10 H10 122(3) . . ? C10 C11 C12 120.8(4) . . ? C10 C11 H11 120(3) . . ? C12 C11 H11 119(3) . . ? C11 C12 C13 118.9(4) . . ? C11 C12 C15 120.8(4) . . ? C13 C12 C15 120.3(4) . . ? C8 C13 C12 120.5(4) . . ? C8 C13 H13 120(3) . . ? C12 C13 H13 120(3) . . ? O2 C14 O1 124.3(3) . . ? O2 C14 C8 118.6(4) . . ? O1 C14 C8 117.1(4) . . ? O4 C15 O3 123.3(4) . . ? O4 C15 C12 120.8(4) . . ? O3 C15 C12 115.9(4) . . ? C14A O1A Zn1 107.5(3) . . ? O2A C14A O1A 122.1(4) . . ? O2A C14A C12A 122.0(4) . . ? O1A C14A C12A 115.9(4) . . ? C13A C12A C11A 119.5(4) . . ? C13A C12A C14A 119.5(4) . . ? C11A C12A C14A 121.1(4) . . ? C10A C11A C12A 120.2(4) . . ? C10A C11A H11A 124(3) . . ? C12A C11A H11A 116(3) . . ? C12A C13A C8A 120.5(4) . . ? C12A C13A H13A 122(2) . . ? C8A C13A H13A 118(2) . . ? C9A C8A C13A 119.2(3) . . ? C9A C8A C15A 120.2(4) . . ? C13A C8A C15A 120.6(3) . . ? C9A C10A C11A 119.8(4) . . ? C9A C10A H10A 123(3) . . ? C11A C10A H10A 117(3) . . ? C10A C9A C8A 120.8(4) . . ? C10A C9A H9A 116(3) . . ? C8A C9A H9A 123(3) . . ? O4A C15A O3A 125.4(3) . . ? O4A C15A C8A 118.7(3) . . ? O3A C15A C8A 115.9(3) . . ? C15A O3A Zn1A 128.9(2) . 2_647 ? C4A N3A N4A 104.1(3) . . ? C4A N3A Zn1 132.3(3) . . ? N4A N3A Zn1 120.6(2) . . ? N3A C4A C5A 111.6(4) . . ? N3A C4A H4A 115(3) . . ? C5A C4A H4A 133(3) . . ? C6A N4A N3A 112.2(3) . . ? C6A N4A H44A 129(3) . . ? N3A N4A H44A 118(3) . . ? C6A C5A C4A 103.6(3) . . ? C6A C5A C7A 127.8(3) . . ? C4A C5A C7A 128.6(3) . . ? N4A C6A C5A 108.4(3) . . ? N4A C6A H6A 125(2) . . ? C5A C6A H6A 126(2) . . ? C5A C7A C2A 114.6(3) . . ? C5A C7A H7D 105(2) . . ? C2A C7A H7D 107(3) . . ? C5A C7A H7C 108(3) . . ? C2A C7A H7C 108(3) . . ? H7D C7A H7C 116(4) . . ? C3A C2A C1A 104.7(4) . . ? C3A C2A C7A 125.7(4) . . ? C1A C2A C7A 129.6(4) . . ? N1A C1A C2A 110.5(4) . . ? N1A C1A H1A 120(3) . . ? C2A C1A H1A 130(3) . . ? N2A C3A C2A 108.0(4) . . ? N2A C3A H3A 123(3) . . ? C2A C3A H3A 129(3) . . ? N2A N1A C1A 105.7(4) . . ? N2A N1A Zn1A 120.9(3) . . ? C1A N1A Zn1A 133.3(3) . . ? O3 Zn1A O3A 105.67(14) 2_756 2_657 ? O3 Zn1A N1A 112.62(14) 2_756 . ? O3A Zn1A N1A 112.42(14) 2_657 . ? O3 Zn1A N3 114.99(14) 2_756 . ? O3A Zn1A N3 95.36(11) 2_657 . ? N1A Zn1A N3 114.20(14) . . ? C3A N2A N1A 111.1(3) . . ? C3A N2A H22A 139(4) . . ? N1A N2A H22A 110(4) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 26.72 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.384 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 873736' ####################################################################### # # 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_10sg003_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 N5 O6 Zn' _chemical_formula_weight 466.75 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' 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 9.4798(12) _cell_length_b 10.1009(12) _cell_length_c 11.1659(14) _cell_angle_alpha 96.353(6) _cell_angle_beta 111.398(5) _cell_angle_gamma 99.654(5) _cell_volume 964.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3304 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 27.02 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 1.322 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.746581 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0594 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14836 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.61 _reflns_number_total 4410 _reflns_number_gt 3263 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0973P)^2^+0.6525P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4410 _refine_ls_number_parameters 254 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0827 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1690 _refine_ls_wR_factor_gt 0.1523 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.41113(5) 0.00913(4) 0.28171(5) 0.03488(18) Uani 1 1 d . . . O1 O 0.5238(3) -0.1280(3) 0.3597(3) 0.0435(7) Uani 1 1 d . . . N1 N 0.2145(4) -0.0261(3) 0.3163(3) 0.0387(8) Uani 1 1 d . . . C1 C 0.0835(5) 0.0146(5) 0.2582(4) 0.0430(10) Uani 1 1 d . . . H1A H 0.0706 0.0728 0.1980 0.052 Uiso 1 1 calc R . . N2 N 0.1843(4) -0.1067(4) 0.3966(4) 0.0424(8) Uani 1 1 d D . . O2 O 0.3417(4) -0.3010(3) 0.2173(4) 0.0688(11) Uani 1 1 d . . . C2 C -0.0308(5) -0.0406(5) 0.2990(4) 0.0447(10) Uani 1 1 d . . . C3 C 0.0396(5) -0.1178(5) 0.3879(4) 0.0462(10) Uani 1 1 d . . . H3A H -0.0066 -0.1688 0.4337 0.055 Uiso 1 1 calc R . . O3 O 0.5856(3) -0.8217(3) 0.3902(3) 0.0431(7) Uani 1 1 d . . . N3 N -0.3453(4) 0.0354(4) -0.0841(3) 0.0414(8) Uani 1 1 d . . . O4 O 0.3794(4) -0.7718(3) 0.2520(3) 0.0544(8) Uani 1 1 d . . . C4 C -0.3124(5) -0.0440(5) 0.0057(5) 0.0498(11) Uani 1 1 d . . . H4A H -0.3289 -0.1386 -0.0134 0.060 Uiso 1 1 calc R . . N4 N -0.3080(5) 0.1617(4) -0.0147(4) 0.0555(10) Uani 1 1 d D . . O5 O 0.9498(4) -0.3452(4) 0.6047(4) 0.0774(13) Uani 1 1 d . . . H5 H 0.9879 -0.3899 0.6489 0.116 Uiso 1 1 d . . . C5 C -0.2501(5) 0.0335(6) 0.1317(5) 0.0498(11) Uani 1 1 d . . . C6 C -0.2518(6) 0.1617(6) 0.1125(5) 0.0664(15) Uani 1 1 d . . . H6A H -0.2186 0.2387 0.1781 0.080 Uiso 1 1 calc R . . C7 C -0.1942(6) -0.0177(7) 0.2597(5) 0.0684(17) Uani 1 1 d . . . H7A H -0.2645 -0.1029 0.2516 0.082 Uiso 1 1 calc R . . H7B H -0.1973 0.0483 0.3283 0.082 Uiso 1 1 calc R . . C8 C 0.5616(5) -0.3530(4) 0.3725(4) 0.0357(8) Uani 1 1 d . . . C9 C 0.4990(5) -0.4921(4) 0.3331(4) 0.0367(9) Uani 1 1 d . . . H9A H 0.3980 -0.5236 0.2709 0.044 Uiso 1 1 calc R . . C10 C 0.5846(5) -0.5842(4) 0.3852(4) 0.0350(8) Uani 1 1 d . . . C11 C 0.7371(5) -0.5369(4) 0.4781(4) 0.0433(10) Uani 1 1 d . . . H11A H 0.7962 -0.5985 0.5130 0.052 Uiso 1 1 calc R . . C12 C 0.7996(5) -0.3968(5) 0.5179(5) 0.0468(10) Uani 1 1 d . . . C13 C 0.7128(5) -0.3054(4) 0.4662(4) 0.0406(9) Uani 1 1 d . . . H13A H 0.7550 -0.2119 0.4936 0.049 Uiso 1 1 calc R . . C14 C 0.4675(5) -0.2542(4) 0.3121(5) 0.0414(10) Uani 1 1 d . . . C15 C 0.5127(5) -0.7336(4) 0.3397(4) 0.0357(8) Uani 1 1 d . . . H444 H -0.309(7) 0.230(5) -0.057(6) 0.08(2) Uiso 1 1 d D . . H222 H 0.265(5) -0.128(6) 0.457(4) 0.080(19) Uiso 1 1 d D . . O1S O 0.9070(7) -0.4880(6) 1.2559(6) 0.123(2) Uiso 1 1 d . . . N1S N 0.8665(13) -0.3855(10) 1.0818(10) 0.158(3) Uiso 1 1 d . . . C3S C 0.9792(16) -0.4334(12) 1.1878(13) 0.161(4) Uiso 1 1 d . . . H3SA H 1.0838 -0.4261 1.2035 0.193 Uiso 1 1 calc R . . C2S C 0.9175(14) -0.3138(12) 0.9889(12) 0.157(4) Uiso 1 1 d . . . H2SA H 1.0290 -0.2886 1.0232 0.236 Uiso 1 1 calc R . . H2SB H 0.8766 -0.2332 0.9785 0.236 Uiso 1 1 calc R . . H2SC H 0.8796 -0.3738 0.9055 0.236 Uiso 1 1 calc R . . C1S C 0.6892(18) -0.4301(15) 1.0539(15) 0.191(6) Uiso 1 1 d . . . H1SB H 0.6772 -0.4705 1.1246 0.286 Uiso 1 1 calc R . . H1SC H 0.6377 -0.4957 0.9736 0.286 Uiso 1 1 calc R . . H1SD H 0.6441 -0.3516 1.0466 0.286 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0333(3) 0.0243(3) 0.0424(3) 0.00646(18) 0.0093(2) 0.00690(18) O1 0.0443(16) 0.0249(14) 0.0609(19) 0.0151(13) 0.0163(14) 0.0119(12) N1 0.0385(18) 0.0358(18) 0.0419(19) 0.0128(15) 0.0136(15) 0.0098(15) C1 0.037(2) 0.052(3) 0.043(2) 0.018(2) 0.0141(18) 0.0169(19) N2 0.043(2) 0.0377(19) 0.047(2) 0.0138(16) 0.0146(17) 0.0125(16) O2 0.054(2) 0.0355(18) 0.088(3) 0.0197(18) -0.0068(19) 0.0093(15) C2 0.036(2) 0.061(3) 0.035(2) 0.008(2) 0.0103(18) 0.012(2) C3 0.048(3) 0.050(3) 0.044(2) 0.014(2) 0.022(2) 0.008(2) O3 0.0514(17) 0.0222(13) 0.0523(18) 0.0110(12) 0.0146(14) 0.0095(12) N3 0.0402(19) 0.0369(18) 0.042(2) 0.0057(15) 0.0105(16) 0.0079(15) O4 0.0535(19) 0.0263(15) 0.062(2) 0.0055(14) 0.0027(16) 0.0016(13) C4 0.050(3) 0.055(3) 0.046(3) 0.016(2) 0.017(2) 0.016(2) N4 0.059(2) 0.041(2) 0.049(2) 0.0008(19) 0.005(2) 0.0079(19) O5 0.045(2) 0.044(2) 0.101(3) 0.008(2) -0.015(2) 0.0034(16) C5 0.030(2) 0.075(3) 0.046(3) 0.012(2) 0.0131(19) 0.017(2) C6 0.059(3) 0.064(3) 0.052(3) -0.010(3) 0.003(3) 0.011(3) C7 0.040(3) 0.130(5) 0.045(3) 0.025(3) 0.020(2) 0.029(3) C8 0.040(2) 0.0262(18) 0.043(2) 0.0101(16) 0.0163(18) 0.0085(16) C9 0.037(2) 0.0296(19) 0.039(2) 0.0072(16) 0.0102(17) 0.0063(16) C10 0.040(2) 0.0209(17) 0.042(2) 0.0067(16) 0.0148(18) 0.0045(15) C11 0.045(2) 0.028(2) 0.054(3) 0.0118(18) 0.011(2) 0.0148(18) C12 0.035(2) 0.039(2) 0.053(3) 0.004(2) 0.0047(19) 0.0047(18) C13 0.043(2) 0.0238(18) 0.051(3) 0.0039(17) 0.016(2) 0.0043(16) C14 0.039(2) 0.030(2) 0.057(3) 0.0152(19) 0.017(2) 0.0098(17) C15 0.045(2) 0.0241(18) 0.038(2) 0.0084(16) 0.0165(18) 0.0074(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.976(3) . ? Zn1 N1 2.020(3) . ? Zn1 N3 2.036(4) 2 ? Zn1 O3 2.063(3) 1_565 ? Zn1 O4 2.325(3) 1_565 ? Zn1 C15 2.537(4) 1_565 ? O1 C14 1.268(5) . ? N1 C1 1.333(5) . ? N1 N2 1.349(5) . ? C1 C2 1.380(6) . ? C1 H1A 0.9300 . ? N2 C3 1.324(6) . ? N2 H222 0.89(2) . ? O2 C14 1.243(5) . ? C2 C3 1.379(6) . ? C2 C7 1.514(6) . ? C3 H3A 0.9300 . ? O3 C15 1.274(5) . ? O3 Zn1 2.063(3) 1_545 ? N3 C4 1.333(5) . ? N3 N4 1.335(5) . ? N3 Zn1 2.036(4) 2 ? O4 C15 1.247(5) . ? O4 Zn1 2.325(3) 1_545 ? C4 C5 1.392(7) . ? C4 H4A 0.9300 . ? N4 C6 1.322(7) . ? N4 H444 0.88(2) . ? O5 C12 1.367(5) . ? O5 H5 0.7427 . ? C5 C6 1.338(8) . ? C5 C7 1.514(7) . ? C6 H6A 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.383(5) . ? C8 C13 1.394(6) . ? C8 C14 1.502(5) . ? C9 C10 1.375(5) . ? C9 H9A 0.9300 . ? C10 C11 1.400(6) . ? C10 C15 1.494(5) . ? C11 C12 1.392(6) . ? C11 H11A 0.9300 . ? C12 C13 1.374(6) . ? C13 H13A 0.9300 . ? C15 Zn1 2.537(4) 1_545 ? O1S C3S 1.303(12) . ? N1S C3S 1.467(14) . ? N1S C2S 1.499(13) . ? N1S C1S 1.568(15) . ? C3S H3SA 0.9300 . ? C2S H2SA 0.9600 . ? C2S H2SB 0.9600 . ? C2S H2SC 0.9600 . ? C1S H1SB 0.9600 . ? C1S H1SC 0.9600 . ? C1S H1SD 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 O1 Zn1 N1 104.45(13) . . ? O1 Zn1 N3 108.36(14) . 2 ? N1 Zn1 N3 106.76(14) . 2 ? O1 Zn1 O3 96.24(12) . 1_565 ? N1 Zn1 O3 119.08(14) . 1_565 ? N3 Zn1 O3 119.79(13) 2 1_565 ? O1 Zn1 O4 155.49(13) . 1_565 ? N1 Zn1 O4 89.66(13) . 1_565 ? N3 Zn1 O4 85.90(13) 2 1_565 ? O3 Zn1 O4 59.25(11) 1_565 1_565 ? O1 Zn1 C15 126.19(13) . 1_565 ? N1 Zn1 C15 105.64(14) . 1_565 ? N3 Zn1 C15 104.17(13) 2 1_565 ? O3 Zn1 C15 29.95(12) 1_565 1_565 ? O4 Zn1 C15 29.30(12) 1_565 1_565 ? C14 O1 Zn1 120.0(3) . . ? C1 N1 N2 105.2(3) . . ? C1 N1 Zn1 128.2(3) . . ? N2 N1 Zn1 126.4(3) . . ? N1 C1 C2 111.4(4) . . ? N1 C1 H1A 124.3 . . ? C2 C1 H1A 124.3 . . ? C3 N2 N1 111.2(3) . . ? C3 N2 H222 130(4) . . ? N1 N2 H222 118(4) . . ? C3 C2 C1 104.2(4) . . ? C3 C2 C7 127.6(4) . . ? C1 C2 C7 128.2(4) . . ? N2 C3 C2 108.1(4) . . ? N2 C3 H3A 126.0 . . ? C2 C3 H3A 126.0 . . ? C15 O3 Zn1 96.1(2) . 1_545 ? C4 N3 N4 104.5(4) . . ? C4 N3 Zn1 130.8(3) . 2 ? N4 N3 Zn1 124.3(3) . 2 ? C15 O4 Zn1 84.8(2) . 1_545 ? N3 C4 C5 111.1(4) . . ? N3 C4 H4A 124.5 . . ? C5 C4 H4A 124.5 . . ? C6 N4 N3 111.2(4) . . ? C6 N4 H444 130(4) . . ? N3 N4 H444 118(4) . . ? C12 O5 H5 117.6 . . ? C6 C5 C4 103.9(4) . . ? C6 C5 C7 128.8(5) . . ? C4 C5 C7 127.3(5) . . ? N4 C6 C5 109.3(5) . . ? N4 C6 H6A 125.4 . . ? C5 C6 H6A 125.4 . . ? C5 C7 C2 112.9(4) . . ? C5 C7 H7A 109.0 . . ? C2 C7 H7A 109.0 . . ? C5 C7 H7B 109.0 . . ? C2 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C13 119.8(3) . . ? C9 C8 C14 119.8(4) . . ? C13 C8 C14 120.4(4) . . ? C10 C9 C8 120.7(4) . . ? C10 C9 H9A 119.7 . . ? C8 C9 H9A 119.7 . . ? C9 C10 C11 119.7(3) . . ? C9 C10 C15 119.0(4) . . ? C11 C10 C15 121.4(3) . . ? C12 C11 C10 119.5(4) . . ? C12 C11 H11A 120.2 . . ? C10 C11 H11A 120.2 . . ? O5 C12 C13 117.7(4) . . ? O5 C12 C11 121.8(4) . . ? C13 C12 C11 120.4(4) . . ? C12 C13 C8 119.9(4) . . ? C12 C13 H13A 120.0 . . ? C8 C13 H13A 120.0 . . ? O2 C14 O1 124.4(4) . . ? O2 C14 C8 118.1(4) . . ? O1 C14 C8 117.5(4) . . ? O4 C15 O3 119.9(4) . . ? O4 C15 C10 119.4(3) . . ? O3 C15 C10 120.7(4) . . ? O4 C15 Zn1 65.9(2) . 1_545 ? O3 C15 Zn1 53.96(19) . 1_545 ? C10 C15 Zn1 174.5(3) . 1_545 ? C3S N1S C2S 120.2(11) . . ? C3S N1S C1S 118.9(11) . . ? C2S N1S C1S 120.2(11) . . ? O1S C3S N1S 108.0(11) . . ? O1S C3S H3SA 126.0 . . ? N1S C3S H3SA 126.0 . . ? N1S C2S H2SA 109.5 . . ? N1S C2S H2SB 109.5 . . ? H2SA C2S H2SB 109.5 . . ? N1S C2S H2SC 109.5 . . ? H2SA C2S H2SC 109.5 . . ? H2SB C2S H2SC 109.5 . . ? N1S C1S H1SB 109.5 . . ? N1S C1S H1SC 109.5 . . ? H1SB C1S H1SC 109.5 . . ? N1S C1S H1SD 109.5 . . ? H1SB C1S H1SD 109.5 . . ? H1SC C1S H1SD 109.5 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.61 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.817 _refine_diff_density_min -0.782 _refine_diff_density_rms 0.100 _database_code_depnum_ccdc_archive 'CCDC 873737' ####################################################################### # # 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_10AG041_1_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 N4 O6 Zn' _chemical_formula_weight 425.70 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.3228(4) _cell_length_b 14.8745(6) _cell_length_c 12.8792(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.712(2) _cell_angle_gamma 90.00 _cell_volume 1742.21(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10409 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 29.89 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 1.453 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.822064 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0590 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 34959 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 34.83 _reflns_number_total 7327 _reflns_number_gt 5031 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0565P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7327 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1052 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.716534(18) 0.189345(9) 0.347532(14) 0.03300(7) Uani 1 1 d . . . O1 O 0.65444(14) 0.31430(6) 0.35811(9) 0.0396(3) Uani 1 1 d . . . O1W O 0.6781(4) 0.66825(19) 0.8192(3) 0.1405(10) Uani 1 1 d . . . H1WB H 0.6558 0.7191 0.7967 0.169 Uiso 1 1 calc R . . H1WA H 0.6503 0.6579 0.7466 0.169 Uiso 1 1 d R . . C1 C 0.95936(17) -0.15804(11) 0.61016(12) 0.0386(3) Uani 1 1 d . . . H1A H 0.9542 -0.1533 0.5374 0.046 Uiso 1 1 calc R . . N1 N 1.08044(15) -0.17988(8) 0.68167(11) 0.0381(3) Uani 1 1 d . . . O2 O 0.82854(15) 0.30618(6) 0.50486(10) 0.0481(3) Uani 1 1 d . . . C2 C 0.84212(16) -0.14333(9) 0.65778(12) 0.0340(3) Uani 1 1 d . . . N2 N 1.04098(17) -0.18033(8) 0.77590(11) 0.0395(3) Uani 1 1 d . . . H222 H 1.109(2) -0.1874(12) 0.8341(17) 0.045(6) Uiso 1 1 d . . . N3 N 0.70910(14) 0.10725(8) 0.47185(10) 0.0368(3) Uani 1 1 d . . . O3 O 0.41341(14) 0.60969(8) 0.25294(9) 0.0509(3) Uani 1 1 d . . . C3 C 0.89858(18) -0.15855(10) 0.76354(13) 0.0403(3) Uani 1 1 d . . . H3A H 0.8472 -0.1545 0.8176 0.048 Uiso 1 1 calc R . . C4 C 0.71582(18) 0.01735(9) 0.47442(13) 0.0386(3) Uani 1 1 d . . . H4A H 0.7356 -0.0182 0.4198 0.046 Uiso 1 1 calc R . . N4 N 0.67788(16) 0.13108(9) 0.56471(11) 0.0418(3) Uani 1 1 d . . . H444 H 0.664(3) 0.1830(14) 0.5802(19) 0.057(6) Uiso 1 1 d . . . O4 O 0.4245(3) 0.71278(11) 0.37306(13) 0.0923(7) Uani 1 1 d . . . O5 O 0.85684(18) 0.62365(8) 0.65778(11) 0.0651(4) Uani 1 1 d . . . C6A C 0.68932(15) -0.01598(9) 0.56939(12) 0.0346(3) Uani 1 1 d . . . C6 C 0.66438(19) 0.05943(12) 0.62379(13) 0.0444(4) Uani 1 1 d . . . H6A H 0.6418 0.0604 0.6906 0.053 Uiso 1 1 calc R . . C7 C 0.68970(16) -0.11221(11) 0.60433(15) 0.0438(4) Uani 1 1 d . . . H7A H 0.6520 -0.1499 0.5429 0.053 Uiso 1 1 calc R . . H7B H 0.6250 -0.1187 0.6534 0.053 Uiso 1 1 calc R . . C8 C 0.71149(16) 0.44789(8) 0.45992(11) 0.0320(3) Uani 1 1 d . . . C9 C 0.60108(16) 0.49622(8) 0.39415(11) 0.0313(3) Uani 1 1 d . . . H9A H 0.5411 0.4687 0.3355 0.038 Uiso 1 1 calc R . . C10 C 0.58012(16) 0.58655(8) 0.41618(11) 0.0331(3) Uani 1 1 d . . . C11 C 0.6671(2) 0.62669(9) 0.50453(13) 0.0427(4) Uani 1 1 d . . . H11A H 0.6511 0.6865 0.5199 0.051 Uiso 1 1 calc R . . C12 C 0.7782(2) 0.57844(9) 0.57050(13) 0.0428(3) Uani 1 1 d . . . C13 C 0.80211(18) 0.48941(9) 0.54780(12) 0.0389(3) Uani 1 1 d . . . H13A H 0.8782 0.4573 0.5909 0.047 Uiso 1 1 calc R . . C14 C 0.73500(17) 0.34948(9) 0.44141(11) 0.0334(3) Uani 1 1 d . . . C15 C 0.46377(18) 0.64076(10) 0.34414(12) 0.0382(3) Uani 1 1 d . . . C16 C 0.9740(3) 0.57839(15) 0.72496(19) 0.0747(7) Uani 1 1 d . . . H16A H 1.0193 0.6174 0.7822 0.112 Uiso 1 1 calc R . . H16B H 1.0453 0.5612 0.6850 0.112 Uiso 1 1 calc R . . H16C H 0.9375 0.5256 0.7535 0.112 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.03261(10) 0.02159(8) 0.04167(11) -0.00341(6) 0.00144(7) 0.00279(5) O1 0.0496(6) 0.0249(5) 0.0380(6) -0.0073(4) -0.0038(5) 0.0091(4) O1W 0.178(3) 0.1001(17) 0.169(3) 0.0207(17) 0.093(2) 0.0094(17) C1 0.0360(7) 0.0444(8) 0.0336(7) 0.0027(6) 0.0034(6) 0.0055(6) N1 0.0345(6) 0.0374(6) 0.0395(7) -0.0009(5) 0.0022(5) 0.0061(5) O2 0.0615(8) 0.0276(5) 0.0445(6) -0.0055(4) -0.0113(6) 0.0144(4) C2 0.0334(7) 0.0278(6) 0.0405(7) 0.0055(5) 0.0074(6) 0.0007(5) N2 0.0465(8) 0.0348(6) 0.0330(6) 0.0018(5) -0.0002(6) 0.0028(5) N3 0.0455(7) 0.0266(5) 0.0368(6) -0.0034(5) 0.0057(5) 0.0054(5) O3 0.0609(8) 0.0399(6) 0.0440(6) 0.0013(5) -0.0052(6) 0.0165(5) C3 0.0458(8) 0.0364(7) 0.0401(8) 0.0022(6) 0.0128(7) 0.0004(6) C4 0.0483(8) 0.0252(6) 0.0430(8) -0.0042(5) 0.0113(7) 0.0057(6) N4 0.0504(8) 0.0314(6) 0.0413(7) -0.0081(5) 0.0049(6) 0.0125(5) O4 0.1500(18) 0.0600(8) 0.0590(9) -0.0065(7) 0.0062(10) 0.0708(11) O5 0.0857(10) 0.0333(6) 0.0594(8) -0.0159(5) -0.0207(7) 0.0038(6) C6A 0.0248(6) 0.0327(6) 0.0449(8) 0.0030(6) 0.0043(6) 0.0047(5) C6 0.0479(9) 0.0479(9) 0.0381(8) -0.0005(7) 0.0113(7) 0.0121(7) C7 0.0316(7) 0.0378(7) 0.0610(10) 0.0119(7) 0.0081(7) -0.0004(6) C8 0.0424(7) 0.0218(5) 0.0311(6) -0.0012(5) 0.0063(6) 0.0046(5) C9 0.0418(7) 0.0244(5) 0.0275(6) -0.0014(5) 0.0071(5) 0.0066(5) C10 0.0460(8) 0.0248(5) 0.0301(6) 0.0020(5) 0.0118(6) 0.0094(5) C11 0.0612(10) 0.0218(6) 0.0424(8) -0.0045(6) 0.0060(7) 0.0059(6) C12 0.0592(10) 0.0242(6) 0.0400(8) -0.0063(5) 0.0001(7) 0.0003(6) C13 0.0487(9) 0.0255(6) 0.0374(7) -0.0015(5) -0.0013(7) 0.0061(6) C14 0.0435(8) 0.0235(5) 0.0315(6) -0.0025(5) 0.0047(6) 0.0043(5) C15 0.0509(9) 0.0301(6) 0.0371(7) 0.0070(5) 0.0172(7) 0.0134(6) C16 0.0828(15) 0.0521(11) 0.0684(13) -0.0170(10) -0.0282(12) 0.0027(10) _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 1.9603(9) . ? Zn1 O3 1.9637(11) 2_645 ? Zn1 N1 2.0143(14) 3_756 ? Zn1 N3 2.0269(13) . ? O1 C14 1.2784(17) . ? O1W H1WB 0.8200 . ? O1W H1WA 0.9262 . ? C1 N1 1.331(2) . ? C1 C2 1.383(2) . ? C1 H1A 0.9300 . ? N1 N2 1.343(2) . ? N1 Zn1 2.0143(14) 3_756 ? O2 C14 1.2367(18) . ? C2 C3 1.367(2) . ? C2 C7 1.509(2) . ? N2 C3 1.341(2) . ? N2 H222 0.87(2) . ? N3 C4 1.3388(17) . ? N3 N4 1.3393(18) . ? O3 C15 1.2534(19) . ? O3 Zn1 1.9637(11) 2_655 ? C3 H3A 0.9300 . ? C4 C6A 1.391(2) . ? C4 H4A 0.9300 . ? N4 C6 1.331(2) . ? N4 H444 0.82(2) . ? O4 C15 1.2167(19) . ? O5 C12 1.3749(19) . ? O5 C16 1.407(3) . ? C6A C6 1.369(2) . ? C6A C7 1.500(2) . ? C6 H6A 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.3821(19) . ? C8 C13 1.398(2) . ? C8 C14 1.5068(17) . ? C9 C10 1.3958(17) . ? C9 H9A 0.9300 . ? C10 C11 1.379(2) . ? C10 C15 1.498(2) . ? C11 C12 1.387(2) . ? C11 H11A 0.9300 . ? C12 C13 1.3847(19) . ? C13 H13A 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 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 O1 Zn1 O3 117.98(5) . 2_645 ? O1 Zn1 N1 112.53(5) . 3_756 ? O3 Zn1 N1 107.68(5) 2_645 3_756 ? O1 Zn1 N3 117.02(5) . . ? O3 Zn1 N3 91.93(5) 2_645 . ? N1 Zn1 N3 107.59(5) 3_756 . ? C14 O1 Zn1 108.58(9) . . ? H1WB O1W H1WA 78.7 . . ? N1 C1 C2 111.37(14) . . ? N1 C1 H1A 124.3 . . ? C2 C1 H1A 124.3 . . ? C1 N1 N2 105.50(13) . . ? C1 N1 Zn1 125.23(11) . 3_756 ? N2 N1 Zn1 128.59(11) . 3_756 ? C3 C2 C1 104.30(13) . . ? C3 C2 C7 128.53(14) . . ? C1 C2 C7 127.08(14) . . ? C3 N2 N1 110.62(13) . . ? C3 N2 H222 129.7(14) . . ? N1 N2 H222 119.2(14) . . ? C4 N3 N4 105.09(13) . . ? C4 N3 Zn1 127.72(10) . . ? N4 N3 Zn1 126.72(9) . . ? C15 O3 Zn1 116.40(10) . 2_655 ? N2 C3 C2 108.20(14) . . ? N2 C3 H3A 125.9 . . ? C2 C3 H3A 125.9 . . ? N3 C4 C6A 111.18(13) . . ? N3 C4 H4A 124.4 . . ? C6A C4 H4A 124.4 . . ? C6 N4 N3 111.41(13) . . ? C6 N4 H444 125.2(16) . . ? N3 N4 H444 123.2(17) . . ? C12 O5 C16 118.09(13) . . ? C6 C6A C4 103.94(13) . . ? C6 C6A C7 128.14(15) . . ? C4 C6A C7 127.92(14) . . ? N4 C6 C6A 108.37(14) . . ? N4 C6 H6A 125.8 . . ? C6A C6 H6A 125.8 . . ? C6A C7 C2 111.67(12) . . ? C6A C7 H7A 109.3 . . ? C2 C7 H7A 109.3 . . ? C6A C7 H7B 109.3 . . ? C2 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C9 C8 C13 120.15(12) . . ? C9 C8 C14 121.53(12) . . ? C13 C8 C14 118.30(12) . . ? C8 C9 C10 119.65(13) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? C11 C10 C9 120.08(13) . . ? C11 C10 C15 119.47(12) . . ? C9 C10 C15 120.45(13) . . ? C10 C11 C12 120.38(13) . . ? C10 C11 H11A 119.8 . . ? C12 C11 H11A 119.8 . . ? O5 C12 C13 123.97(15) . . ? O5 C12 C11 116.09(13) . . ? C13 C12 C11 119.92(14) . . ? C12 C13 C8 119.78(14) . . ? C12 C13 H13A 120.1 . . ? C8 C13 H13A 120.1 . . ? O2 C14 O1 122.67(12) . . ? O2 C14 C8 120.49(12) . . ? O1 C14 C8 116.84(12) . . ? O4 C15 O3 122.39(15) . . ? O4 C15 C10 120.65(15) . . ? O3 C15 C10 116.92(12) . . ? O5 C16 H16A 109.5 . . ? O5 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O5 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 34.83 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.452 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 873738' ####################################################################### # # 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_10ag050_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 N4 O5 Zn' _chemical_formula_weight 423.72 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 8.4157(5) _cell_length_b 16.7161(10) _cell_length_c 13.1197(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.980(2) _cell_angle_gamma 90.00 _cell_volume 1845.38(18) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9407 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 29.37 _exptl_crystal_description Block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 1.367 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.831342 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0678 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 35041 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 32.94 _reflns_number_total 6810 _reflns_number_gt 4576 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0774P)^2^+0.1255P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6810 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1346 _refine_ls_wR_factor_gt 0.1217 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.002 _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 0.10398(3) 0.117121(13) 0.747798(16) 0.03794(9) Uani 1 1 d . . . O1 O 0.0324(2) 0.10860(9) 0.88775(11) 0.0488(4) Uani 1 1 d . . . C8 C 0.0695(2) 0.11766(11) 1.06535(15) 0.0387(4) Uani 1 1 d . . . N1 N 0.2194(2) 0.01773(10) 0.70401(12) 0.0419(4) Uani 1 1 d . . . C10 C -0.0812(2) 0.21147(11) 1.16334(15) 0.0408(4) Uani 1 1 d . . . C2 C 0.3344(2) -0.08475(13) 0.62375(15) 0.0423(4) Uani 1 1 d . . . O2 O 0.2111(2) 0.02804(10) 0.95984(11) 0.0569(4) Uani 1 1 d . . . C9 C -0.0453(2) 0.17717(11) 1.07033(15) 0.0394(4) Uani 1 1 d . . . H9A H -0.0981 0.1940 1.0113 0.047 Uiso 1 1 calc R . . C11 C -0.0019(3) 0.18495(13) 1.25136(15) 0.0447(4) Uani 1 1 d . . . H11A H -0.0266 0.2078 1.3137 0.054 Uiso 1 1 calc R . . C15 C 0.1090(2) 0.08079(12) 0.96445(14) 0.0404(4) Uani 1 1 d . . . N2 N 0.2887(2) -0.03087(10) 0.77243(13) 0.0449(4) Uani 1 1 d . . . C13 C 0.1472(3) 0.09287(14) 1.15412(15) 0.0447(4) Uani 1 1 d . . . H13A H 0.2246 0.0533 1.1505 0.054 Uiso 1 1 calc R . . C1 C 0.2476(3) -0.01499(14) 0.61353(15) 0.0483(5) Uani 1 1 d . . . H1A H 0.2133 0.0064 0.5515 0.058 Uiso 1 1 calc R . . C12 C 0.1116(3) 0.12594(14) 1.24843(15) 0.0466(5) Uani 1 1 d . . . C3 C 0.3584(3) -0.09230(13) 0.72672(16) 0.0465(5) Uani 1 1 d . . . H3A H 0.4140 -0.1334 0.7592 0.056 Uiso 1 1 calc R . . C7 C 0.3892(3) -0.14196(18) 0.54310(18) 0.0601(7) Uani 1 1 d . . . H7A H 0.5017 -0.1336 0.5322 0.072 Uiso 1 1 calc R . . H7B H 0.3755 -0.1963 0.5674 0.072 Uiso 1 1 calc R . . C14 C 0.1929(4) 0.09698(19) 1.3448(2) 0.0697(8) Uani 1 1 d . . . H14A H 0.1541 0.1266 1.4019 0.105 Uiso 1 1 calc R . . H14B H 0.3055 0.1047 1.3397 0.105 Uiso 1 1 calc R . . H14C H 0.1709 0.0411 1.3541 0.105 Uiso 1 1 calc R . . O1S O -0.3639(3) 0.07687(17) 0.90819(15) 0.0882(7) Uani 1 1 d . . . C1S C -0.4521(5) 0.1321(2) 0.9632(3) 0.0927(11) Uani 1 1 d . . . H1SC H -0.4240 0.1282 1.0342 0.139 Uiso 1 1 calc R . . H1SB H -0.5634 0.1209 0.9539 0.139 Uiso 1 1 calc R . . H1SA H -0.4299 0.1851 0.9392 0.139 Uiso 1 1 calc R . . H222 H 0.279(3) -0.0224(15) 0.8386(19) 0.057(7) Uiso 1 1 d . . . H1S H -0.285(4) 0.039(2) 0.950(3) 0.112(13) Uiso 1 1 d . . . C16 C -0.2064(3) 0.27473(12) 1.16935(17) 0.0454(4) Uani 1 1 d . . . O3 O -0.2627(2) 0.30646(11) 1.09224(14) 0.0627(4) Uani 1 1 d . . . O4 O -0.2477(2) 0.29451(10) 1.25893(13) 0.0590(4) Uani 1 1 d . . . C5 C 0.3012(3) -0.13261(13) 0.44318(16) 0.0458(5) Uani 1 1 d . . . C4 C 0.1411(3) -0.14267(15) 0.42208(15) 0.0474(5) Uani 1 1 d . . . H4A H 0.0664 -0.1568 0.4703 0.057 Uiso 1 1 calc R . . C6 C 0.3652(3) -0.11328(13) 0.35010(19) 0.0499(5) Uani 1 1 d . . . H6A H 0.4716 -0.1029 0.3376 0.060 Uiso 1 1 calc R . . N3 N 0.1071(2) -0.12955(11) 0.32347(13) 0.0441(4) Uani 1 1 d . . . N4 N 0.2456(2) -0.11222(11) 0.28073(15) 0.0464(4) Uani 1 1 d . . . H444 H 0.262(3) -0.1069(14) 0.212(2) 0.056(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.04561(15) 0.04040(14) 0.02768(13) -0.00250(8) -0.00285(9) -0.00027(8) O1 0.0526(9) 0.0667(10) 0.0271(7) 0.0034(6) 0.0009(6) 0.0044(7) C8 0.0427(10) 0.0442(10) 0.0293(9) -0.0013(7) 0.0022(7) -0.0038(7) N1 0.0519(9) 0.0445(8) 0.0294(7) -0.0022(6) -0.0010(7) 0.0034(7) C10 0.0446(10) 0.0399(9) 0.0381(10) -0.0019(7) 0.0018(8) -0.0036(8) C2 0.0398(10) 0.0523(11) 0.0347(10) -0.0091(8) -0.0041(7) 0.0047(8) O2 0.0692(10) 0.0697(10) 0.0316(7) -0.0055(7) 0.0012(7) 0.0210(8) C9 0.0451(10) 0.0409(9) 0.0323(9) 0.0032(7) 0.0000(7) -0.0030(7) C11 0.0480(11) 0.0519(11) 0.0341(10) -0.0086(8) 0.0003(8) 0.0007(9) C15 0.0459(10) 0.0466(10) 0.0286(9) -0.0001(7) 0.0019(7) -0.0045(8) N2 0.0585(11) 0.0466(9) 0.0297(8) -0.0008(7) 0.0012(7) 0.0056(8) C13 0.0454(11) 0.0577(11) 0.0311(9) -0.0046(8) -0.0009(8) 0.0070(9) C1 0.0563(12) 0.0586(12) 0.0298(9) -0.0036(8) -0.0055(8) 0.0121(10) C12 0.0502(12) 0.0591(13) 0.0301(10) -0.0060(8) -0.0045(8) 0.0034(9) C3 0.0555(12) 0.0488(11) 0.0352(10) -0.0002(8) 0.0002(9) 0.0083(9) C7 0.0575(13) 0.0822(16) 0.0400(12) -0.0236(11) -0.0150(10) 0.0316(12) C14 0.0752(18) 0.0943(19) 0.0389(12) -0.0092(12) -0.0159(12) 0.0283(15) O1S 0.0991(16) 0.1179(18) 0.0480(11) 0.0225(11) 0.0132(10) 0.0424(15) C1S 0.073(2) 0.108(3) 0.097(3) -0.006(2) 0.0000(19) 0.0088(19) C16 0.0488(11) 0.0404(10) 0.0472(11) -0.0020(8) 0.0035(9) -0.0006(8) O3 0.0721(11) 0.0638(10) 0.0519(10) 0.0002(8) -0.0074(8) 0.0207(9) O4 0.0735(11) 0.0546(9) 0.0491(9) 0.0019(7) 0.0098(8) 0.0215(8) C5 0.0482(11) 0.0548(11) 0.0343(10) -0.0124(8) -0.0063(8) 0.0152(9) C4 0.0472(11) 0.0671(13) 0.0277(9) -0.0019(9) -0.0020(8) 0.0068(10) C6 0.0430(11) 0.0591(13) 0.0477(12) -0.0042(9) 0.0032(9) 0.0084(9) N3 0.0462(9) 0.0559(10) 0.0301(8) -0.0008(7) -0.0025(7) 0.0034(7) N4 0.0466(10) 0.0600(11) 0.0329(9) 0.0010(7) 0.0032(7) 0.0089(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 1.9380(16) 4_665 y Zn1 O1 1.9475(15) . y Zn1 N3 2.0037(18) 3_556 y Zn1 N1 2.0130(17) . y O1 C15 1.274(2) . ? C8 C13 1.389(3) . ? C8 C9 1.389(3) . ? C8 C15 1.503(3) . ? N1 C1 1.332(2) . ? N1 N2 1.337(2) . ? C10 C9 1.386(3) . ? C10 C11 1.396(3) . ? C10 C16 1.496(3) . ? C2 C3 1.368(3) . ? C2 C1 1.381(3) . ? C2 C7 1.505(3) . ? O2 C15 1.233(2) . ? C9 H9A 0.9300 . ? C11 C12 1.374(3) . ? C11 H11A 0.9300 . ? N2 C3 1.330(3) . ? N2 H222 0.88(3) . ? C13 C12 1.392(3) . ? C13 H13A 0.9300 . ? C1 H1A 0.9300 . ? C12 C14 1.507(3) . ? C3 H3A 0.9300 . ? C7 C5 1.503(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? O1S C1S 1.393(4) . ? O1S H1S 1.06(4) . ? C1S H1SC 0.9600 . ? C1S H1SB 0.9600 . ? C1S H1SA 0.9600 . ? C16 O3 1.230(3) . ? C16 O4 1.275(3) . ? O4 Zn1 1.9380(16) 4_566 ? C5 C6 1.381(3) . ? C5 C4 1.381(3) . ? C4 N3 1.338(3) . ? C4 H4A 0.9300 . ? C6 N4 1.346(3) . ? C6 H6A 0.9300 . ? N3 N4 1.334(3) . ? N3 Zn1 2.0037(18) 3_556 ? N4 H444 0.92(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Zn1 O1 101.19(7) 4_665 . y O4 Zn1 N3 121.39(8) 4_665 3_556 y O1 Zn1 N3 99.29(7) . 3_556 y O4 Zn1 N1 109.71(8) 4_665 . y O1 Zn1 N1 111.54(7) . . y N3 Zn1 N1 112.36(7) 3_556 . y C15 O1 Zn1 127.64(14) . . ? C13 C8 C9 119.47(18) . . ? C13 C8 C15 120.53(18) . . ? C9 C8 C15 119.99(18) . . ? C1 N1 N2 105.44(16) . . ? C1 N1 Zn1 133.43(14) . . ? N2 N1 Zn1 121.13(12) . . ? C9 C10 C11 119.24(18) . . ? C9 C10 C16 120.20(18) . . ? C11 C10 C16 120.54(18) . . ? C3 C2 C1 104.05(18) . . ? C3 C2 C7 126.4(2) . . ? C1 C2 C7 129.52(19) . . ? C10 C9 C8 119.99(18) . . ? C10 C9 H9A 120.0 . . ? C8 C9 H9A 120.0 . . ? C12 C11 C10 121.84(18) . . ? C12 C11 H11A 119.1 . . ? C10 C11 H11A 119.1 . . ? O2 C15 O1 124.47(18) . . ? O2 C15 C8 120.10(17) . . ? O1 C15 C8 115.43(18) . . ? C3 N2 N1 110.92(17) . . ? C3 N2 H222 128.1(16) . . ? N1 N2 H222 120.8(16) . . ? C8 C13 C12 121.4(2) . . ? C8 C13 H13A 119.3 . . ? C12 C13 H13A 119.3 . . ? N1 C1 C2 111.23(18) . . ? N1 C1 H1A 124.4 . . ? C2 C1 H1A 124.4 . . ? C11 C12 C13 118.02(18) . . ? C11 C12 C14 120.87(19) . . ? C13 C12 C14 121.1(2) . . ? N2 C3 C2 108.35(19) . . ? N2 C3 H3A 125.8 . . ? C2 C3 H3A 125.8 . . ? C5 C7 C2 113.26(18) . . ? C5 C7 H7A 108.9 . . ? C2 C7 H7A 108.9 . . ? C5 C7 H7B 108.9 . . ? C2 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C1S O1S H1S 118(2) . . ? O1S C1S H1SC 109.5 . . ? O1S C1S H1SB 109.5 . . ? H1SC C1S H1SB 109.5 . . ? O1S C1S H1SA 109.5 . . ? H1SC C1S H1SA 109.5 . . ? H1SB C1S H1SA 109.5 . . ? O3 C16 O4 122.6(2) . . ? O3 C16 C10 121.55(19) . . ? O4 C16 C10 115.79(19) . . ? C16 O4 Zn1 108.27(14) . 4_566 ? C6 C5 C4 104.17(19) . . ? C6 C5 C7 127.0(2) . . ? C4 C5 C7 128.8(2) . . ? N3 C4 C5 111.5(2) . . ? N3 C4 H4A 124.3 . . ? C5 C4 H4A 124.3 . . ? N4 C6 C5 107.6(2) . . ? N4 C6 H6A 126.2 . . ? C5 C6 H6A 126.2 . . ? N4 N3 C4 105.52(18) . . ? N4 N3 Zn1 123.73(14) . 3_556 ? C4 N3 Zn1 129.90(16) . 3_556 ? N3 N4 C6 111.21(19) . . ? N3 N4 H444 125.3(18) . . ? C6 N4 H444 123.0(18) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 32.94 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.480 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 873739' ####################################################################### # # 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_11ag065_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H27 N4 O6 Zn' _chemical_formula_weight 544.88 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 14.8499(6) _cell_length_b 9.3390(4) _cell_length_c 35.7679(15) _cell_angle_alpha 90.00 _cell_angle_beta 99.9050(10) _cell_angle_gamma 90.00 _cell_volume 4886.5(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6703 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 28.12 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2264 _exptl_absorpt_coefficient_mu 1.054 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.739999 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0733 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 31893 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 1.16 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5712 _reflns_number_gt 4517 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+13.8113P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5712 _refine_ls_number_parameters 341 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1310 _refine_ls_wR_factor_gt 0.1247 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 0.18892(2) 0.33512(4) 0.137605(10) 0.02348(12) Uani 1 1 d . . . O1 O 0.08222(15) 0.3503(3) 0.09716(6) 0.0294(5) Uani 1 1 d . . . N1 N 0.27770(17) 0.4883(3) 0.12866(7) 0.0236(5) Uani 1 1 d . . . C1 C 0.3114(2) 0.5953(3) 0.15156(9) 0.0257(7) Uani 1 1 d . . . H1A H 0.3050 0.6027 0.1769 0.031 Uiso 1 1 calc R . . O2 O 0.17446(15) 0.2823(2) 0.05806(6) 0.0290(5) Uani 1 1 d . . . N2 N 0.30233(18) 0.5186(3) 0.09507(8) 0.0241(6) Uani 1 1 d . . . H222 H 0.281(2) 0.471(4) 0.0764(10) 0.028(10) Uiso 1 1 d . . . C2 C 0.3572(2) 0.6945(3) 0.13277(9) 0.0230(6) Uani 1 1 d . . . O3 O -0.28493(16) 0.5034(3) -0.01433(6) 0.0350(6) Uani 1 1 d . . . C3 C 0.3503(2) 0.6394(3) 0.09668(9) 0.0256(7) Uani 1 1 d . . . H3A H 0.3749 0.6797 0.0769 0.031 Uiso 1 1 calc R . . N3 N 0.24963(19) 1.1448(3) 0.15012(7) 0.0261(6) Uani 1 1 d . . . O4 O -0.20974(18) 0.5739(3) 0.04194(7) 0.0385(7) Uani 1 1 d . . . H44 H -0.250(3) 0.625(5) 0.0428(13) 0.054(14) Uiso 1 1 d . . . N4 N 0.2374(2) 1.0713(3) 0.18131(8) 0.0306(6) Uani 1 1 d . . . H444 H 0.205(3) 1.111(4) 0.1964(12) 0.042(11) Uiso 1 1 d . . . C4 C 0.3101(2) 1.0692(3) 0.13478(9) 0.0270(7) Uani 1 1 d . . . H4A H 0.3320 1.0951 0.1129 0.032 Uiso 1 1 calc R . . O5 O 0.14642(17) 0.4202(3) 0.18138(6) 0.0351(6) Uani 1 1 d . . . C5 C 0.3364(2) 0.9461(3) 0.15587(9) 0.0247(7) Uani 1 1 d . . . C6 C 0.2884(2) 0.9532(4) 0.18531(10) 0.0309(7) Uani 1 1 d . . . H6A H 0.2910 0.8867 0.2048 0.037 Uiso 1 1 calc R . . O6 O 0.1274(3) 0.2277(3) 0.21541(11) 0.0743(12) Uani 1 1 d . . . C7 C 0.4026(2) 0.8323(3) 0.14825(10) 0.0293(7) Uani 1 1 d . . . H7A H 0.4441 0.8114 0.1717 0.035 Uiso 1 1 calc R . . H7B H 0.4388 0.8692 0.1302 0.035 Uiso 1 1 calc R . . C8 C 0.0175(2) 0.3280(3) 0.03237(8) 0.0218(6) Uani 1 1 d . . . C9 C 0.0206(2) 0.2621(3) -0.00216(8) 0.0225(6) Uani 1 1 d . . . H9A H 0.0741 0.2164 -0.0057 0.027 Uiso 1 1 calc R . . C10 C -0.0545(2) 0.2623(3) -0.03175(8) 0.0210(6) Uani 1 1 d . . . C11 C -0.1319(2) 0.3360(3) -0.02590(9) 0.0240(6) Uani 1 1 d . . . H11A H -0.1832 0.3362 -0.0449 0.029 Uiso 1 1 calc R . . C12 C -0.1351(2) 0.4099(3) 0.00769(8) 0.0223(6) Uani 1 1 d . . . C13 C -0.0609(2) 0.4041(3) 0.03716(8) 0.0220(6) Uani 1 1 d . . . H13A H -0.0633 0.4505 0.0600 0.026 Uiso 1 1 calc R . . C14 C 0.0984(2) 0.3186(3) 0.06428(9) 0.0230(6) Uani 1 1 d . . . C15 C -0.2176(2) 0.4979(3) 0.01005(8) 0.0248(6) Uani 1 1 d . . . C16 C -0.0497(2) 0.1801(3) -0.06831(9) 0.0248(6) Uani 1 1 d . . . C17 C 0.0278(3) 0.2382(4) -0.08730(11) 0.0412(9) Uani 1 1 d . . . H17A H 0.0298 0.1856 -0.1102 0.062 Uiso 1 1 calc R . . H17B H 0.0849 0.2278 -0.0703 0.062 Uiso 1 1 calc R . . H17C H 0.0170 0.3377 -0.0933 0.062 Uiso 1 1 calc R . . C18 C -0.1379(3) 0.1883(4) -0.09659(10) 0.0429(10) Uani 1 1 d . . . H18A H -0.1315 0.1353 -0.1190 0.064 Uiso 1 1 calc R . . H18B H -0.1514 0.2865 -0.1032 0.064 Uiso 1 1 calc R . . H18C H -0.1867 0.1483 -0.0855 0.064 Uiso 1 1 calc R . . C19 C -0.0311(3) 0.0223(4) -0.05813(11) 0.0390(9) Uani 1 1 d . . . H19A H -0.0795 -0.0147 -0.0462 0.058 Uiso 1 1 calc R . . H19B H 0.0260 0.0139 -0.0410 0.058 Uiso 1 1 calc R . . H19C H -0.0282 -0.0313 -0.0808 0.058 Uiso 1 1 calc R . . C20 C 0.1147(2) 0.3557(4) 0.20726(10) 0.0312(7) Uani 1 1 d . . . C21 C 0.0558(2) 0.4396(4) 0.22942(9) 0.0267(7) Uani 1 1 d . . . C22 C 0.0000 0.3654(5) 0.2500 0.0239(9) Uani 1 2 d S . . H22 H 0.0000 0.2659 0.2500 0.036 Uiso 1 2 calc SR . . C23 C 0.0540(3) 0.5875(4) 0.22909(10) 0.0337(8) Uani 1 1 d . . . H23A H 0.0899 0.6370 0.2145 0.040 Uiso 1 1 calc R . . C24 C 0.0000 0.6633(5) 0.2500 0.0380(12) Uani 1 2 d S . . C25 C 0.0000 0.8288(6) 0.2500 0.0607(18) Uani 1 2 d S . . C26 C -0.0057(7) 0.8812(11) 0.2056(3) 0.061(2) Uiso 0.50 1 d P A 1 H26A H 0.0519 0.8635 0.1977 0.092 Uiso 0.50 1 calc PR A 1 H26B H -0.0191 0.9818 0.2037 0.092 Uiso 0.50 1 calc PR A 1 H26C H -0.0530 0.8289 0.1896 0.092 Uiso 0.50 1 calc PR A 1 C27 C -0.1055(7) 0.8828(12) 0.2424(3) 0.064(3) Uiso 0.50 1 d P A 4 H27A H -0.1313 0.8695 0.2650 0.096 Uiso 0.50 1 calc PR A 4 H27B H -0.1398 0.8285 0.2220 0.096 Uiso 0.50 1 calc PR A 4 H27C H -0.1077 0.9825 0.2358 0.096 Uiso 0.50 1 calc PR A 4 C28 C -0.0588(17) 0.902(3) 0.2697(7) 0.079(6) Uiso 0.25 1 d P A 2 H28A H -0.1073 0.8401 0.2739 0.119 Uiso 0.25 1 calc PR A 2 H28B H -0.0839 0.9837 0.2550 0.119 Uiso 0.25 1 calc PR A 2 H28C H -0.0255 0.9345 0.2936 0.119 Uiso 0.25 1 calc PR A 2 C29 C -0.0651(19) 0.887(3) 0.2238(8) 0.086(7) Uiso 0.25 1 d P A 3 H29A H -0.1197 0.9003 0.2344 0.129 Uiso 0.25 1 calc PR A 3 H29B H -0.0779 0.8243 0.2023 0.129 Uiso 0.25 1 calc PR A 3 H29C H -0.0445 0.9777 0.2160 0.129 Uiso 0.25 1 calc PR A 3 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 0.0260(2) 0.02139(19) 0.02313(19) 0.00161(14) 0.00444(13) 0.00017(15) O1 0.0279(12) 0.0372(13) 0.0227(11) -0.0034(9) 0.0034(9) 0.0020(10) N1 0.0255(13) 0.0214(13) 0.0245(13) 0.0012(10) 0.0064(10) 0.0013(10) C1 0.0294(17) 0.0285(17) 0.0186(14) -0.0013(12) 0.0025(12) 0.0022(13) O2 0.0229(11) 0.0304(12) 0.0333(12) -0.0065(10) 0.0039(9) 0.0036(9) N2 0.0273(14) 0.0233(14) 0.0224(13) -0.0026(11) 0.0059(11) -0.0003(11) C2 0.0221(15) 0.0188(15) 0.0279(16) 0.0005(11) 0.0040(12) 0.0023(11) O3 0.0281(12) 0.0479(15) 0.0281(12) -0.0066(11) 0.0029(10) 0.0097(11) C3 0.0278(16) 0.0200(16) 0.0313(17) 0.0029(12) 0.0116(13) 0.0027(12) N3 0.0323(14) 0.0224(14) 0.0246(13) 0.0026(10) 0.0076(11) 0.0001(11) O4 0.0310(14) 0.0474(16) 0.0350(14) -0.0166(11) 0.0000(11) 0.0172(12) N4 0.0395(17) 0.0263(15) 0.0288(15) 0.0031(12) 0.0141(13) 0.0077(12) C4 0.0311(17) 0.0252(16) 0.0263(16) -0.0015(13) 0.0096(13) -0.0024(13) O5 0.0449(15) 0.0356(14) 0.0288(12) -0.0031(10) 0.0179(11) -0.0048(11) C5 0.0248(16) 0.0214(15) 0.0270(16) -0.0040(12) 0.0025(12) -0.0026(12) C6 0.0371(19) 0.0260(17) 0.0312(17) 0.0059(13) 0.0106(14) 0.0067(14) O6 0.104(3) 0.0368(17) 0.105(3) 0.0184(17) 0.082(2) 0.0245(18) C7 0.0252(16) 0.0250(16) 0.0387(18) -0.0056(14) 0.0082(13) -0.0011(13) C8 0.0251(15) 0.0167(14) 0.0237(14) 0.0008(12) 0.0041(12) -0.0016(12) C9 0.0201(15) 0.0230(15) 0.0257(15) 0.0005(12) 0.0074(12) 0.0014(12) C10 0.0235(15) 0.0173(14) 0.0226(14) -0.0001(11) 0.0050(12) 0.0003(11) C11 0.0231(15) 0.0225(15) 0.0263(15) 0.0012(12) 0.0036(12) 0.0006(12) C12 0.0226(15) 0.0219(15) 0.0239(15) 0.0010(12) 0.0080(12) 0.0011(12) C13 0.0260(16) 0.0202(15) 0.0208(14) 0.0000(11) 0.0069(12) -0.0005(12) C14 0.0253(16) 0.0167(14) 0.0266(15) 0.0003(11) 0.0039(12) -0.0027(12) C15 0.0253(16) 0.0277(16) 0.0222(15) -0.0013(12) 0.0066(12) 0.0019(13) C16 0.0262(15) 0.0228(16) 0.0252(15) -0.0031(12) 0.0042(12) 0.0029(12) C17 0.049(2) 0.042(2) 0.036(2) -0.0084(16) 0.0178(17) -0.0087(18) C18 0.038(2) 0.053(2) 0.0339(19) -0.0133(17) -0.0027(16) 0.0119(17) C19 0.046(2) 0.0268(18) 0.043(2) -0.0056(15) 0.0060(17) 0.0029(16) C20 0.0304(17) 0.0323(19) 0.0335(18) -0.0039(14) 0.0127(14) -0.0041(14) C21 0.0302(17) 0.0291(17) 0.0211(15) -0.0023(12) 0.0055(13) -0.0028(13) C22 0.029(2) 0.018(2) 0.025(2) 0.000 0.0072(18) 0.000 C23 0.044(2) 0.0271(18) 0.0320(18) 0.0038(14) 0.0114(15) -0.0054(15) C24 0.048(3) 0.023(2) 0.045(3) 0.000 0.015(2) 0.000 C25 0.080(5) 0.025(3) 0.081(5) 0.000 0.027(4) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O5 1.955(2) . ? Zn1 O1 1.958(2) . ? Zn1 N1 2.008(3) . ? Zn1 N3 2.008(3) 1_545 ? O1 C14 1.275(4) . ? N1 C1 1.334(4) . ? N1 N2 1.345(4) . ? C1 C2 1.389(4) . ? C1 H1A 0.9300 . ? O2 C14 1.235(4) . ? N2 C3 1.331(4) . ? N2 H222 0.82(4) . ? C2 C3 1.377(4) . ? C2 C7 1.512(4) . ? O3 C15 1.210(4) . ? C3 H3A 0.9300 . ? N3 C4 1.333(4) . ? N3 N4 1.348(4) . ? N3 Zn1 2.008(3) 1_565 ? O4 C15 1.332(4) . ? O4 H44 0.77(5) . ? N4 C6 1.331(4) . ? N4 H444 0.87(4) . ? C4 C5 1.393(4) . ? C4 H4A 0.9300 . ? O5 C20 1.262(4) . ? C5 C6 1.371(5) . ? C5 C7 1.505(4) . ? C6 H6A 0.9300 . ? O6 C20 1.237(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.388(4) . ? C8 C13 1.399(4) . ? C8 C14 1.511(4) . ? C9 C10 1.398(4) . ? C9 H9A 0.9300 . ? C10 C11 1.387(4) . ? C10 C16 1.529(4) . ? C11 C12 1.393(4) . ? C11 H11A 0.9300 . ? C12 C13 1.389(4) . ? C12 C15 1.490(4) . ? C13 H13A 0.9300 . ? C16 C18 1.513(4) . ? C16 C19 1.531(5) . ? C16 C17 1.532(5) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.499(5) . ? C21 C23 1.381(5) . ? C21 C22 1.385(4) . ? C22 C21 1.385(4) 2 ? C22 H22 0.9300 . ? C23 C24 1.382(4) . ? C23 H23A 0.9300 . ? C24 C23 1.382(4) 2 ? C24 C25 1.546(7) . ? C25 C29 1.34(3) 2 ? C25 C29 1.34(3) . ? C25 C28 1.39(2) . ? C25 C28 1.39(2) 2 ? C25 C27 1.624(11) 2 ? C25 C27 1.624(11) . ? C25 C26 1.650(10) 2 ? C25 C26 1.650(10) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 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 O5 Zn1 O1 103.34(10) . . ? O5 Zn1 N1 98.59(10) . . ? O1 Zn1 N1 107.51(10) . . ? O5 Zn1 N3 112.07(11) . 1_545 ? O1 Zn1 N3 120.25(10) . 1_545 ? N1 Zn1 N3 112.58(11) . 1_545 ? C14 O1 Zn1 114.1(2) . . ? C1 N1 N2 105.1(3) . . ? C1 N1 Zn1 128.5(2) . . ? N2 N1 Zn1 125.4(2) . . ? N1 C1 C2 111.4(3) . . ? N1 C1 H1A 124.3 . . ? C2 C1 H1A 124.3 . . ? C3 N2 N1 111.5(3) . . ? C3 N2 H222 129(3) . . ? N1 N2 H222 119(3) . . ? C3 C2 C1 103.9(3) . . ? C3 C2 C7 128.1(3) . . ? C1 C2 C7 127.9(3) . . ? N2 C3 C2 108.1(3) . . ? N2 C3 H3A 126.0 . . ? C2 C3 H3A 126.0 . . ? C4 N3 N4 105.5(3) . . ? C4 N3 Zn1 133.3(2) . 1_565 ? N4 N3 Zn1 121.0(2) . 1_565 ? C15 O4 H44 114(3) . . ? C6 N4 N3 110.8(3) . . ? C6 N4 H444 131(3) . . ? N3 N4 H444 118(3) . . ? N3 C4 C5 111.1(3) . . ? N3 C4 H4A 124.4 . . ? C5 C4 H4A 124.4 . . ? C20 O5 Zn1 127.3(2) . . ? C6 C5 C4 104.0(3) . . ? C6 C5 C7 128.0(3) . . ? C4 C5 C7 128.0(3) . . ? N4 C6 C5 108.6(3) . . ? N4 C6 H6A 125.7 . . ? C5 C6 H6A 125.7 . . ? C5 C7 C2 113.8(3) . . ? C5 C7 H7A 108.8 . . ? C2 C7 H7A 108.8 . . ? C5 C7 H7B 108.8 . . ? C2 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C9 C8 C13 119.3(3) . . ? C9 C8 C14 120.2(3) . . ? C13 C8 C14 120.5(3) . . ? C8 C9 C10 121.9(3) . . ? C8 C9 H9A 119.0 . . ? C10 C9 H9A 119.0 . . ? C11 C10 C9 117.4(3) . . ? C11 C10 C16 122.7(3) . . ? C9 C10 C16 119.9(3) . . ? C10 C11 C12 121.9(3) . . ? C10 C11 H11A 119.1 . . ? C12 C11 H11A 119.1 . . ? C13 C12 C11 119.7(3) . . ? C13 C12 C15 122.1(3) . . ? C11 C12 C15 118.2(3) . . ? C12 C13 C8 119.7(3) . . ? C12 C13 H13A 120.2 . . ? C8 C13 H13A 120.2 . . ? O2 C14 O1 123.6(3) . . ? O2 C14 C8 120.9(3) . . ? O1 C14 C8 115.6(3) . . ? O3 C15 O4 122.3(3) . . ? O3 C15 C12 124.7(3) . . ? O4 C15 C12 113.0(3) . . ? C18 C16 C10 112.6(3) . . ? C18 C16 C19 107.9(3) . . ? C10 C16 C19 108.2(3) . . ? C18 C16 C17 108.4(3) . . ? C10 C16 C17 110.5(3) . . ? C19 C16 C17 109.2(3) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O6 C20 O5 124.9(3) . . ? O6 C20 C21 117.4(3) . . ? O5 C20 C21 117.6(3) . . ? C23 C21 C22 119.5(3) . . ? C23 C21 C20 122.0(3) . . ? C22 C21 C20 118.4(3) . . ? C21 C22 C21 119.9(4) 2 . ? C21 C22 H22 120.0 2 . ? C21 C22 H22 120.0 . . ? C21 C23 C24 121.3(3) . . ? C21 C23 H23A 119.4 . . ? C24 C23 H23A 119.4 . . ? C23 C24 C23 118.4(5) 2 . ? C23 C24 C25 120.8(2) 2 . ? C23 C24 C25 120.8(2) . . ? C29 C25 C29 132(2) 2 . ? C29 C25 C28 83.5(15) 2 . ? C29 C25 C28 73.3(15) . . ? C29 C25 C28 73.3(15) 2 2 ? C29 C25 C28 83.5(15) . 2 ? C28 C25 C28 121(2) . 2 ? C29 C25 C24 113.9(12) 2 . ? C29 C25 C24 113.9(12) . . ? C28 C25 C24 119.6(11) . . ? C28 C25 C24 119.6(11) 2 . ? C29 C25 C27 36.6(12) 2 2 ? C29 C25 C27 123.4(13) . 2 ? C28 C25 C27 115.6(11) . 2 ? C28 C25 C27 42.3(10) 2 2 ? C24 C25 C27 108.1(4) . 2 ? C29 C25 C27 123.4(12) 2 . ? C29 C25 C27 36.6(12) . . ? C28 C25 C27 42.3(10) . . ? C28 C25 C27 115.6(11) 2 . ? C24 C25 C27 108.1(4) . . ? C27 C25 C27 143.8(9) 2 . ? C29 C25 C26 45.3(12) 2 2 ? C29 C25 C26 117.6(13) . 2 ? C28 C25 C26 45.6(10) . 2 ? C28 C25 C26 114.0(11) 2 2 ? C24 C25 C26 107.3(4) . 2 ? C27 C25 C26 81.9(5) 2 2 ? C27 C25 C26 87.5(5) . 2 ? C29 C25 C26 117.6(13) 2 . ? C29 C25 C26 45.3(12) . . ? C28 C25 C26 114.0(11) . . ? C28 C25 C26 45.6(10) 2 . ? C24 C25 C26 107.3(4) . . ? C27 C25 C26 87.5(5) 2 . ? C27 C25 C26 81.9(5) . . ? C26 C25 C26 145.5(8) 2 . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C25 C29 H29A 109.5 . . ? C25 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C25 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.920 _refine_diff_density_min -0.667 _refine_diff_density_rms 0.087 _database_code_depnum_ccdc_archive 'CCDC 873740' ####################################################################### # # 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_11ssg083_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 Br N4 O5 Zn' _chemical_formula_weight 488.60 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.4539(5) _cell_length_b 16.3640(10) _cell_length_c 13.2550(8) _cell_angle_alpha 90.00 _cell_angle_beta 92.011(2) _cell_angle_gamma 90.00 _cell_volume 1832.56(19) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5607 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 29.69 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.771 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 3.557 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.638180 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0899 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 25160 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 28.99 _reflns_number_total 4728 _reflns_number_gt 3233 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The hydrogen atoms for the methanol molecule could not be located in the data and therefore have not been included in the refinement. This has led to a difference in calculated and reported formula and consequent alerts in the cif check. The bromine atom show some positional disorder with a 80% occupency for the major component and two minor components with 10% site occupency. One or two additional minor components are also present in the structure but site occupecy of these components are too small to model. And this caused a little high value for the ratio of max:min residual electron density. ; _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^)+(0.0993P)^2^+0.4960P] 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 4728 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0844 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1709 _refine_ls_wR_factor_gt 0.1600 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 Br1 Br 0.20149(9) 0.10467(6) 0.64018(5) 0.0363(2) Uani 0.80 1 d P B . Zn1 Zn 0.07119(6) 0.11125(3) 1.24900(3) 0.02884(17) Uani 1 1 d . . . O1 O 0.0042(4) 0.10097(17) 1.1071(2) 0.0354(7) Uani 1 1 d . . . N1 N -0.1329(4) 0.1229(2) 1.3183(3) 0.0324(8) Uani 1 1 d . . . C1 C -0.1560(5) 0.1379(3) 1.4153(3) 0.0352(9) Uani 1 1 d . . . H1A H -0.0763 0.1523 1.4622 0.042 Uiso 1 1 calc R . . O1S O -0.3869(5) 0.0611(3) 1.0864(3) 0.0624(11) Uani 1 1 d . . . C1S C -0.4628(11) 0.1345(7) 1.0315(8) 0.111(3) Uani 1 1 d . . . N2 N -0.2767(5) 0.1037(2) 1.2775(3) 0.0363(8) Uani 1 1 d . . . H2A H -0.2943 0.0909 1.2151 0.044 Uiso 1 1 calc R . . O2 O 0.2103(4) 0.0349(2) 1.0440(2) 0.0456(8) Uani 1 1 d . . . C2 C -0.3157(5) 0.1293(3) 1.4378(3) 0.0317(9) Uani 1 1 d . . . C3 C -0.3888(6) 0.1071(2) 1.3469(3) 0.0356(10) Uani 1 1 d . . . H3A H -0.4960 0.0965 1.3358 0.043 Uiso 1 1 calc R . . O3 O -0.2810(4) 0.2977(2) 0.7376(2) 0.0455(8) Uani 1 1 d . . . N3 N -0.1978(4) -0.01442(19) 1.7042(2) 0.0285(7) Uani 1 1 d . . . O4 O -0.2920(5) 0.3064(2) 0.9028(3) 0.0620(11) Uani 1 1 d . . . C4 C -0.2262(5) 0.0200(3) 1.6130(3) 0.0329(9) Uani 1 1 d . . . H4A H -0.1806 0.0030 1.5537 0.039 Uiso 1 1 calc R . . N4 N -0.2886(4) 0.0276(2) 1.7674(2) 0.0321(8) Uani 1 1 d . . . H4B H -0.2936 0.0176 1.8309 0.039 Uiso 1 1 calc R . . C5 C -0.3328(5) 0.0844(3) 1.6194(3) 0.0316(9) Uani 1 1 d . . . C6 C -0.3699(5) 0.0865(3) 1.7197(3) 0.0341(9) Uani 1 1 d . . . H6A H -0.4395 0.1227 1.7490 0.041 Uiso 1 1 calc R . . C7 C -0.3939(6) 0.1412(3) 1.5370(3) 0.0427(11) Uani 1 1 d . . . H7A H -0.5069 0.1329 1.5269 0.051 Uiso 1 1 calc R . . H7B H -0.3776 0.1972 1.5589 0.051 Uiso 1 1 calc R . . C8 C 0.0512(5) 0.1204(2) 0.9344(3) 0.0302(9) Uani 1 1 d . . . C9 C 0.1347(5) 0.0991(2) 0.8501(3) 0.0318(9) Uani 1 1 d . B . H9A H 0.2167 0.0613 0.8547 0.038 Uiso 1 1 calc R . . C10 C 0.0926(5) 0.1361(3) 0.7582(3) 0.0329(9) Uani 1 1 d . . . C11 C -0.0255(5) 0.1925(2) 0.7502(3) 0.0319(9) Uani 1 1 d . . . H11A H -0.0510 0.2166 0.6882 0.038 Uiso 1 1 calc R A 2 C12 C -0.1082(5) 0.2142(2) 0.8357(3) 0.0306(8) Uani 1 1 d . . . C13 C -0.0682(5) 0.1784(2) 0.9276(3) 0.0304(8) Uani 1 1 d . B . H13A H -0.1216 0.1932 0.9850 0.036 Uiso 1 1 calc R . . C14 C 0.0933(5) 0.0819(3) 1.0367(3) 0.0322(9) Uani 1 1 d . . . C15 C -0.2376(6) 0.2772(3) 0.8277(3) 0.0389(10) Uani 1 1 d . B . Br1' Br -0.0469(7) 0.2598(4) 0.6363(4) 0.0584(13) Uiso 0.10 1 d P . 2 Br1" Br 0.2179(8) 0.1323(3) 0.6455(5) 0.0288(17) Uiso 0.10 1 d P B 3 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0367(4) 0.0529(5) 0.0202(3) 0.0001(3) 0.0128(2) 0.0065(3) Zn1 0.0339(3) 0.0337(3) 0.0192(3) 0.00212(16) 0.00386(19) 0.00018(19) O1 0.0382(18) 0.0492(18) 0.0189(13) -0.0009(11) 0.0040(12) 0.0011(13) N1 0.033(2) 0.0419(19) 0.0226(16) 0.0015(14) 0.0025(14) 0.0025(15) C1 0.036(2) 0.049(2) 0.0209(19) 0.0032(17) 0.0017(16) 0.007(2) O1S 0.059(2) 0.089(3) 0.0381(19) -0.0161(19) -0.0064(17) 0.026(2) C1S 0.081(6) 0.141(8) 0.113(8) -0.023(6) 0.016(5) -0.021(6) N2 0.034(2) 0.051(2) 0.0241(17) -0.0066(14) -0.0027(15) 0.0075(16) O2 0.049(2) 0.065(2) 0.0227(15) 0.0034(13) 0.0000(13) 0.0146(17) C2 0.033(2) 0.040(2) 0.0230(19) 0.0081(16) 0.0072(16) 0.0092(18) C3 0.030(2) 0.041(2) 0.037(2) 0.0030(17) 0.0021(18) 0.0026(17) O3 0.055(2) 0.0450(18) 0.0358(16) -0.0044(13) -0.0069(15) 0.0131(15) N3 0.0311(18) 0.0324(16) 0.0222(15) 0.0006(13) 0.0023(13) -0.0008(14) O4 0.075(3) 0.074(2) 0.0386(19) 0.0007(17) 0.0133(17) 0.038(2) C4 0.034(2) 0.043(2) 0.0215(18) 0.0057(16) 0.0046(16) 0.0027(18) N4 0.040(2) 0.0396(19) 0.0165(15) -0.0010(13) 0.0028(13) 0.0013(15) C5 0.028(2) 0.043(2) 0.0233(19) 0.0052(16) 0.0037(16) 0.0008(18) C6 0.036(2) 0.041(2) 0.026(2) -0.0005(17) 0.0033(17) 0.0051(18) C7 0.040(3) 0.063(3) 0.025(2) 0.014(2) 0.0141(18) 0.019(2) C8 0.034(2) 0.037(2) 0.0197(18) 0.0003(15) 0.0009(16) -0.0025(17) C9 0.031(2) 0.043(2) 0.0210(19) -0.0007(15) 0.0006(16) 0.0009(17) C10 0.034(2) 0.044(2) 0.0215(19) -0.0018(16) 0.0080(17) -0.0017(19) C11 0.034(2) 0.039(2) 0.0227(18) 0.0035(15) 0.0027(16) -0.0041(18) C12 0.032(2) 0.0323(19) 0.0273(19) -0.0046(16) 0.0041(16) -0.0071(17) C13 0.034(2) 0.035(2) 0.0230(18) -0.0028(15) 0.0043(15) -0.0019(17) C14 0.034(2) 0.042(2) 0.0213(19) -0.0019(16) 0.0026(16) -0.0021(19) C15 0.053(3) 0.032(2) 0.031(2) 0.0008(17) -0.0022(19) -0.005(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 Br1 C10 1.913(4) . ? Zn1 O1 1.953(3) . ? Zn1 O3 1.954(3) 4_666 ? Zn1 N1 1.992(4) . ? Zn1 N3 1.999(3) 3_558 ? O1 C14 1.259(5) . ? N1 C1 1.330(5) . ? N1 N2 1.351(5) . ? C1 C2 1.400(6) . ? C1 H1A 0.9300 . ? O1S C1S 1.534(12) . ? C1S Br1' 2.344(11) 4_566 ? N2 C3 1.345(6) . ? N2 H2A 0.8600 . ? O2 C14 1.254(5) . ? C2 C3 1.384(6) . ? C2 C7 1.504(6) . ? C3 H3A 0.9300 . ? O3 C15 1.282(5) . ? O3 Zn1 1.954(3) 4_565 ? N3 N4 1.345(4) . ? N3 C4 1.347(5) . ? N3 Zn1 1.999(3) 3_558 ? O4 C15 1.209(5) . ? C4 C5 1.391(6) . ? C4 H4A 0.9300 . ? N4 C6 1.330(5) . ? N4 H4B 0.8600 . ? C5 C6 1.377(6) . ? C5 C7 1.513(6) . ? C6 H6A 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C13 1.386(6) . ? C8 C9 1.388(6) . ? C8 C14 1.525(5) . ? C9 C10 1.394(6) . ? C9 H9A 0.9300 . ? C10 C11 1.362(6) . ? C10 Br1" 1.862(8) . ? C11 C12 1.398(5) . ? C11 Br1' 1.872(7) . ? C11 H11A 0.9300 . ? C12 C13 1.383(6) . ? C12 C15 1.504(6) . ? C13 H13A 0.9300 . ? Br1' C1S 2.344(11) 4_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 O1 Zn1 O3 98.97(13) . 4_666 ? O1 Zn1 N1 103.08(14) . . ? O3 Zn1 N1 121.96(15) 4_666 . ? O1 Zn1 N3 111.40(12) . 3_558 ? O3 Zn1 N3 106.97(14) 4_666 3_558 ? N1 Zn1 N3 113.28(14) . 3_558 ? C14 O1 Zn1 125.1(3) . . ? C1 N1 N2 105.7(4) . . ? C1 N1 Zn1 128.5(3) . . ? N2 N1 Zn1 125.1(3) . . ? N1 C1 C2 111.3(4) . . ? N1 C1 H1A 124.4 . . ? C2 C1 H1A 124.4 . . ? O1S C1S Br1' 115.3(6) . 4_566 ? C3 N2 N1 111.2(4) . . ? C3 N2 H2A 124.4 . . ? N1 N2 H2A 124.4 . . ? C3 C2 C1 104.2(4) . . ? C3 C2 C7 126.8(4) . . ? C1 C2 C7 129.0(4) . . ? N2 C3 C2 107.7(4) . . ? N2 C3 H3A 126.2 . . ? C2 C3 H3A 126.2 . . ? C15 O3 Zn1 106.9(3) . 4_565 ? N4 N3 C4 104.9(3) . . ? N4 N3 Zn1 121.5(2) . 3_558 ? C4 N3 Zn1 133.4(3) . 3_558 ? N3 C4 C5 111.0(4) . . ? N3 C4 H4A 124.5 . . ? C5 C4 H4A 124.5 . . ? C6 N4 N3 111.7(3) . . ? C6 N4 H4B 124.1 . . ? N3 N4 H4B 124.1 . . ? C6 C5 C4 104.3(4) . . ? C6 C5 C7 126.8(4) . . ? C4 C5 C7 128.9(4) . . ? N4 C6 C5 108.0(4) . . ? N4 C6 H6A 126.0 . . ? C5 C6 H6A 126.0 . . ? C2 C7 C5 113.7(4) . . ? C2 C7 H7A 108.8 . . ? C5 C7 H7A 108.8 . . ? C2 C7 H7B 108.8 . . ? C5 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C13 C8 C9 120.6(4) . . ? C13 C8 C14 119.2(4) . . ? C9 C8 C14 120.2(4) . . ? C8 C9 C10 118.3(4) . . ? C8 C9 H9A 120.9 . . ? C10 C9 H9A 120.9 . . ? C11 C10 C9 121.7(4) . . ? C11 C10 Br1" 113.3(4) . . ? C9 C10 Br1" 123.5(4) . . ? C11 C10 Br1 119.4(3) . . ? C9 C10 Br1 118.8(3) . . ? Br1" C10 Br1 14.46(16) . . ? C10 C11 C12 119.7(4) . . ? C10 C11 Br1' 120.8(3) . . ? C12 C11 Br1' 117.9(4) . . ? C10 C11 H11A 120.2 . . ? C12 C11 H11A 120.2 . . ? Br1' C11 H11A 12.9 . . ? C13 C12 C11 119.5(4) . . ? C13 C12 C15 120.5(4) . . ? C11 C12 C15 120.0(4) . . ? C12 C13 C8 120.2(4) . . ? C12 C13 H13A 119.9 . . ? C8 C13 H13A 119.9 . . ? O2 C14 O1 125.8(4) . . ? O2 C14 C8 118.8(4) . . ? O1 C14 C8 115.4(4) . . ? O4 C15 O3 124.0(4) . . ? O4 C15 C12 120.6(4) . . ? O3 C15 C12 115.4(4) . . ? C11 Br1' C1S 152.7(4) . 4_665 ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 28.99 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 1.842 _refine_diff_density_min -0.859 _refine_diff_density_rms 0.123 _database_code_depnum_ccdc_archive 'CCDC 873741' ####################################################################### # # 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_11sb068_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H17 I N4 O7 Zn' _chemical_formula_weight 557.60 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' I I -0.4742 1.8119 '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 9.5734(4) _cell_length_b 10.1279(4) _cell_length_c 11.3140(5) _cell_angle_alpha 80.5030(10) _cell_angle_beta 66.3940(10) _cell_angle_gamma 80.4300(10) _cell_volume 985.31(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4990 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.01 _exptl_crystal_description Block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.879 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 2.858 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.755931 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0773 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12882 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4151 _reflns_number_gt 3463 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The hydrogen atoms for one water molecule (O3W) could not be located in the data and therefore have not been included in the refinement. This has led to a difference in calculated and reported formula and consequent alerts in the cif check. ; _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^)+(0.0493P)^2^+1.5786P] 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 4151 _refine_ls_number_parameters 253 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0923 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.50580(3) 0.41078(3) 0.32250(3) 0.03821(11) Uani 1 1 d . . . Zn1 Zn -0.08622(5) 0.93913(4) 0.71092(4) 0.02162(12) Uani 1 1 d . . . O1 O 0.0697(3) 0.7913(3) 0.6212(3) 0.0256(6) Uani 1 1 d . . . C1 C -0.4174(4) 0.9328(4) 0.7489(4) 0.0248(8) Uani 1 1 d . . . H1A H -0.4352 0.8652 0.8181 0.030 Uiso 1 1 calc R . . N1 N -0.2815(4) 0.9760(3) 0.6789(3) 0.0233(7) Uani 1 1 d . . . O1W O 0.1330(9) 0.5805(8) -0.0949(6) 0.166(4) Uani 1 1 d . . . H1WA H 0.1336 0.5145 -0.0797 0.249 Uiso 1 1 d . . . H1WB H 0.1806 0.6291 -0.0741 0.249 Uiso 1 1 d . . . O2 O -0.1294(3) 0.6918(3) 0.7579(3) 0.0321(7) Uani 1 1 d . . . N2 N -0.3054(4) 1.0731(3) 0.5903(3) 0.0270(7) Uani 1 1 d . . . H2A H -0.2352 1.1183 0.5326 0.032 Uiso 1 1 calc R . . C2 C -0.5297(4) 1.0011(4) 0.7061(4) 0.0252(8) Uani 1 1 d . . . C3 C -0.4522(5) 1.0903(4) 0.6033(4) 0.0293(9) Uani 1 1 d . . . H3A H -0.4945 1.1513 0.5522 0.035 Uiso 1 1 calc R . . O3 O 0.0389(3) 0.0891(3) 0.6191(3) 0.0254(6) Uani 1 1 d . . . N3 N -0.8735(4) 1.0772(3) 1.0986(3) 0.0260(7) Uani 1 1 d . . . O3W O 0.3096(7) 0.4570(6) 0.0205(6) 0.112(2) Uani 1 1 d . . . O4 O -0.1647(3) 0.2156(3) 0.7391(3) 0.0336(7) Uani 1 1 d . . . C4 C -0.7866(5) 0.9952(4) 1.0092(4) 0.0296(9) Uani 1 1 d . . . H4A H -0.7337 0.9136 1.0266 0.036 Uiso 1 1 calc R . . N4 N -0.9296(5) 1.1810(4) 1.0343(4) 0.0388(9) Uani 1 1 d . . . H4B H -0.9896 1.2493 1.0691 0.047 Uiso 1 1 calc R . . C5 C -0.7847(4) 1.0461(4) 0.8870(4) 0.0268(8) Uani 1 1 d . . . C6 C -0.8795(6) 1.1641(5) 0.9086(5) 0.0430(12) Uani 1 1 d . . . H6A H -0.9051 1.2229 0.8461 0.052 Uiso 1 1 calc R . . C7 C -0.6978(5) 0.9841(5) 0.7616(4) 0.0313(9) Uani 1 1 d . . . H7A H -0.7098 0.8887 0.7768 0.038 Uiso 1 1 calc R . . H7B H -0.7418 1.0252 0.6988 0.038 Uiso 1 1 calc R . . C8 C 0.0752(4) 0.5551(4) 0.6166(3) 0.0210(7) Uani 1 1 d . . . C9 C -0.0043(4) 0.4423(4) 0.6621(4) 0.0204(7) Uani 1 1 d . . . H9A H -0.1020 0.4485 0.7271 0.024 Uiso 1 1 calc R . . C10 C 0.0605(4) 0.3204(4) 0.6114(3) 0.0207(7) Uani 1 1 d . . . C11 C 0.2081(4) 0.3104(4) 0.5156(4) 0.0222(8) Uani 1 1 d . . . H11A H 0.2536 0.2288 0.4825 0.027 Uiso 1 1 calc R . . C12 C 0.2863(4) 0.4235(4) 0.4703(4) 0.0224(8) Uani 1 1 d . . . C13 C 0.2228(4) 0.5456(4) 0.5189(4) 0.0216(8) Uani 1 1 d . . . H13A H 0.2771 0.6204 0.4872 0.026 Uiso 1 1 calc R . . C14 C -0.0006(4) 0.6859(4) 0.6690(4) 0.0231(8) Uani 1 1 d . . . C15 C -0.0299(4) 0.2000(4) 0.6606(4) 0.0225(8) Uani 1 1 d . . . O2W O 0.3943(6) 0.6788(5) 0.0545(5) 0.100(2) Uani 1 1 d D . . H2WB H 0.3308 0.6551 0.0365 0.150 Uiso 1 1 d D . . H2WA H 0.4831 0.6927 0.0387 0.150 Uiso 1 1 d 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 I1 0.02678(16) 0.03423(19) 0.04116(19) -0.00932(13) 0.00213(12) -0.00409(12) Zn1 0.0204(2) 0.0182(2) 0.0236(2) -0.00378(17) -0.00547(17) -0.00137(17) O1 0.0286(14) 0.0146(13) 0.0294(15) -0.0018(11) -0.0070(12) -0.0022(11) C1 0.0240(18) 0.023(2) 0.025(2) -0.0042(15) -0.0063(15) -0.0040(16) N1 0.0224(15) 0.0195(17) 0.0257(17) -0.0024(13) -0.0074(13) -0.0008(13) O1W 0.171(7) 0.164(7) 0.080(4) -0.012(4) -0.018(4) 0.125(6) O2 0.0316(15) 0.0219(15) 0.0328(16) -0.0073(12) -0.0003(12) -0.0033(12) N2 0.0243(16) 0.0274(19) 0.0244(17) 0.0000(14) -0.0048(13) -0.0045(14) C2 0.0230(18) 0.031(2) 0.0209(19) -0.0083(16) -0.0066(15) -0.0008(16) C3 0.028(2) 0.030(2) 0.029(2) -0.0049(17) -0.0115(17) 0.0025(17) O3 0.0279(14) 0.0148(14) 0.0314(15) -0.0029(11) -0.0086(12) -0.0038(11) N3 0.0263(16) 0.0246(18) 0.0241(17) -0.0035(13) -0.0070(13) -0.0008(14) O3W 0.113(5) 0.096(4) 0.087(4) 0.007(3) -0.006(3) -0.008(4) O4 0.0280(15) 0.0244(16) 0.0390(17) -0.0092(13) 0.0002(13) -0.0058(12) C4 0.032(2) 0.026(2) 0.026(2) -0.0058(16) -0.0075(17) 0.0033(17) N4 0.046(2) 0.034(2) 0.033(2) -0.0088(16) -0.0178(17) 0.0160(17) C5 0.0197(17) 0.034(2) 0.025(2) -0.0059(17) -0.0071(15) -0.0010(16) C6 0.047(3) 0.049(3) 0.033(2) -0.007(2) -0.021(2) 0.013(2) C7 0.0241(19) 0.043(3) 0.028(2) -0.0108(18) -0.0086(16) -0.0032(18) C8 0.0272(18) 0.0165(19) 0.0203(18) -0.0026(14) -0.0106(15) -0.0002(15) C9 0.0234(17) 0.0167(19) 0.0208(18) -0.0026(14) -0.0090(14) 0.0002(15) C10 0.0242(18) 0.0179(19) 0.0208(18) -0.0005(14) -0.0104(15) -0.0014(15) C11 0.0249(18) 0.0192(19) 0.0241(19) -0.0063(15) -0.0120(15) 0.0038(15) C12 0.0191(17) 0.022(2) 0.0222(19) -0.0037(15) -0.0050(14) 0.0007(15) C13 0.0239(18) 0.0148(18) 0.0251(19) -0.0003(14) -0.0085(15) -0.0036(15) C14 0.0274(19) 0.022(2) 0.0214(19) -0.0032(15) -0.0114(16) -0.0004(16) C15 0.0279(19) 0.020(2) 0.0206(18) -0.0002(15) -0.0112(15) -0.0021(16) O2W 0.093(4) 0.060(3) 0.084(4) -0.002(3) 0.017(3) 0.024(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C12 2.097(4) . ? Zn1 O3 1.977(3) 1_565 ? Zn1 N1 2.008(3) . ? Zn1 O1 2.011(3) . ? Zn1 N3 2.014(3) 2_477 ? O1 C14 1.281(5) . ? C1 N1 1.327(5) . ? C1 C2 1.389(6) . ? C1 H1A 0.9300 . ? N1 N2 1.344(4) . ? O1W H1WA 0.6616 . ? O1W H1WB 0.8390 . ? O2 C14 1.240(5) . ? N2 C3 1.338(5) . ? N2 H2A 0.8600 . ? C2 C3 1.380(6) . ? C2 C7 1.503(5) . ? C3 H3A 0.9300 . ? O3 C15 1.264(5) . ? O3 Zn1 1.977(3) 1_545 ? N3 C4 1.334(5) . ? N3 N4 1.340(5) . ? N3 Zn1 2.014(3) 2_477 ? O4 C15 1.240(5) . ? C4 C5 1.387(6) . ? C4 H4A 0.9300 . ? N4 C6 1.337(6) . ? N4 H4B 0.8600 . ? C5 C6 1.367(6) . ? C5 C7 1.508(6) . ? C6 H6A 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.389(5) . ? C8 C13 1.402(5) . ? C8 C14 1.493(5) . ? C9 C10 1.390(5) . ? C9 H9A 0.9300 . ? C10 C11 1.395(5) . ? C10 C15 1.512(5) . ? C11 C12 1.386(5) . ? C11 H11A 0.9300 . ? C12 C13 1.381(5) . ? C13 H13A 0.9300 . ? O2W H2WB 0.7959 . ? O2W H2WA 0.8275 . ? 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 N1 108.28(12) 1_565 . ? O3 Zn1 O1 96.61(11) 1_565 . ? N1 Zn1 O1 117.33(12) . . ? O3 Zn1 N3 109.33(12) 1_565 2_477 ? N1 Zn1 N3 111.92(13) . 2_477 ? O1 Zn1 N3 112.03(12) . 2_477 ? C14 O1 Zn1 103.2(2) . . ? N1 C1 C2 111.6(4) . . ? N1 C1 H1A 124.2 . . ? C2 C1 H1A 124.2 . . ? C1 N1 N2 105.3(3) . . ? C1 N1 Zn1 129.9(3) . . ? N2 N1 Zn1 123.8(2) . . ? H1WA O1W H1WB 124.7 . . ? C3 N2 N1 111.4(3) . . ? C3 N2 H2A 124.3 . . ? N1 N2 H2A 124.3 . . ? C3 C2 C1 104.1(3) . . ? C3 C2 C7 128.1(4) . . ? C1 C2 C7 127.8(4) . . ? N2 C3 C2 107.6(4) . . ? N2 C3 H3A 126.2 . . ? C2 C3 H3A 126.2 . . ? C15 O3 Zn1 111.4(2) . 1_545 ? C4 N3 N4 105.1(3) . . ? C4 N3 Zn1 130.0(3) . 2_477 ? N4 N3 Zn1 124.9(3) . 2_477 ? N3 C4 C5 111.9(4) . . ? N3 C4 H4A 124.1 . . ? C5 C4 H4A 124.1 . . ? C6 N4 N3 110.8(4) . . ? C6 N4 H4B 124.6 . . ? N3 N4 H4B 124.6 . . ? C6 C5 C4 103.4(4) . . ? C6 C5 C7 129.1(4) . . ? C4 C5 C7 127.5(4) . . ? N4 C6 C5 108.8(4) . . ? N4 C6 H6A 125.6 . . ? C5 C6 H6A 125.6 . . ? C2 C7 C5 112.8(3) . . ? C2 C7 H7A 109.0 . . ? C5 C7 H7A 109.0 . . ? C2 C7 H7B 109.0 . . ? C5 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C13 119.6(3) . . ? C9 C8 C14 119.3(3) . . ? C13 C8 C14 121.1(3) . . ? C8 C9 C10 120.8(3) . . ? C8 C9 H9A 119.6 . . ? C10 C9 H9A 119.6 . . ? C9 C10 C11 119.7(3) . . ? C9 C10 C15 119.7(3) . . ? C11 C10 C15 120.7(3) . . ? C12 C11 C10 119.2(3) . . ? C12 C11 H11A 120.4 . . ? C10 C11 H11A 120.4 . . ? C13 C12 C11 121.8(3) . . ? C13 C12 I1 118.8(3) . . ? C11 C12 I1 119.4(3) . . ? C12 C13 C8 119.0(3) . . ? C12 C13 H13A 120.5 . . ? C8 C13 H13A 120.5 . . ? O2 C14 O1 120.8(4) . . ? O2 C14 C8 120.2(3) . . ? O1 C14 C8 119.0(3) . . ? O4 C15 O3 124.4(3) . . ? O4 C15 C10 118.6(3) . . ? O3 C15 C10 117.0(3) . . ? H2WB O2W H2WA 152.9 . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 1.827 _refine_diff_density_min -1.143 _refine_diff_density_rms 0.112 _database_code_depnum_ccdc_archive 'CCDC 873742' ####################################################################### # # 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_10ssg062_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H26 N6 O12 Zn2' _chemical_formula_weight 709.24 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 12.5177(5) _cell_length_b 7.5794(3) _cell_length_c 15.9998(6) _cell_angle_alpha 90.00 _cell_angle_beta 111.745(2) _cell_angle_gamma 90.00 _cell_volume 1409.99(10) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5330 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 31.02 _exptl_crystal_description Block _exptl_crystal_colour Brown _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 1.774 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.773375 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0773 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 25017 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 31.78 _reflns_number_total 4731 _reflns_number_gt 3308 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The bis-pyrazole ligand molecule shows considerable amount of positional disorder, which could be attributed to the relatively large void space within the structure. Three cabon atoms (C1, C2 and C3) and one nitrogen atom (N2) of the pyrazole ring show disorder with 50% site occupency for both the components. While one of the oxygen atoms (O1) of the carboxylate group shows some a disorder with 50% site occupency. The hydrogen atoms for the ligand molecule and one water molecule (O1W) could not be located in the data and therefore have not been included in the refinement. This has led to a difference in calculated and reported formula and consequent alerts in the cif check. ; _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^)+(0.0831P)^2^+0.2389P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4731 _refine_ls_number_parameters 252 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1430 _refine_ls_wR_factor_gt 0.1289 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.056 _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 0.85765(3) 0.01358(3) 0.177036(19) 0.03215(12) Uani 1 1 d . . . N3 N 0.70080(19) 0.1248(2) 0.16226(14) 0.0312(4) Uani 1 1 d . . . C13 C 0.5951(2) 0.2338(3) 0.00796(15) 0.0288(5) Uani 1 1 d . . . H13A H 0.5586 0.1252 -0.0080 0.035 Uiso 1 1 calc R . . C12 C 0.5733(2) 0.3679(3) -0.05570(15) 0.0282(5) Uani 1 1 d . . . C11 C 0.6282(2) 0.5299(3) -0.03153(17) 0.0307(5) Uani 1 1 d . . . H11 H 0.6137 0.6195 -0.0740 0.037 Uiso 1 1 calc R . . C9 C 0.7268(2) 0.4241(3) 0.11938(15) 0.0289(5) Uani 1 1 d . . . H8A H 0.7787 0.4424 0.1778 0.035 Uiso 1 1 calc R . . C8 C 0.6714(2) 0.2628(3) 0.09536(15) 0.0277(5) Uani 1 1 d . . . C10 C 0.7046(2) 0.5583(3) 0.05595(16) 0.0307(5) Uani 1 1 d . . . O2W O 0.6448(10) -0.0596(11) -0.1583(6) 0.297(7) Uani 1 1 d D . . H2WB H 0.7158 -0.1326 -0.1590 0.446 Uiso 1 1 d D . . H2WA H 0.6641 0.0591 -0.1712 0.446 Uiso 1 1 d D . . O1W O 1.2002(10) -0.0565(17) 0.2540(7) 0.353(8) Uani 1 1 d . . . C14 C 0.7588(2) 0.7356(3) 0.08293(17) 0.0370(6) Uani 1 1 d . A . O2 O 0.82394(17) 0.7581(2) 0.16507(12) 0.0367(4) Uani 1 1 d . . . O1 O 0.7281(15) 0.862(2) 0.0311(9) 0.038(2) Uani 0.50 1 d P . . C15 C 0.4871(2) 0.3402(3) -0.14942(16) 0.0316(5) Uani 1 1 d . . . O4 O 0.47221(18) 0.4730(2) -0.20193(13) 0.0402(5) Uani 1 1 d . . . O3 O 0.43593(19) 0.1985(2) -0.17129(13) 0.0488(5) Uani 1 1 d . . . H3AB H 0.649(4) 0.024(5) 0.146(3) 0.064(12) Uiso 1 1 d . . . H3AA H 0.715(3) 0.164(4) 0.217(2) 0.044(8) Uiso 1 1 d . . . C7 C 0.9470(9) 0.4001(14) -0.0838(6) 0.101(4) Uani 0.50 1 d P A 1 N1 N 0.9300(2) 0.1473(4) 0.10409(17) 0.0532(7) Uani 1 1 d . A 1 N2 N 1.0462(5) 0.1563(10) 0.1276(4) 0.0686(18) Uani 0.50 1 d P A 1 C1 C 1.0702(8) 0.2560(18) 0.0682(7) 0.108(5) Uani 0.50 1 d P A 1 C2 C 0.9661(15) 0.307(2) 0.0013(11) 0.069(4) Uani 0.50 1 d P A 1 C3 C 0.8871(10) 0.2117(13) 0.0231(9) 0.0329(17) Uani 0.50 1 d P A 1 N2' N 0.9879(5) 0.3117(8) 0.1392(4) 0.0640(16) Uani 0.50 1 d P B 2 C1' C 0.9977(7) 0.4154(11) 0.0695(5) 0.0604(19) Uani 0.50 1 d P B 2 C2' C 0.937(2) 0.307(3) -0.0066(12) 0.116(9) Uani 0.50 1 d P B 2 C3' C 0.8941(17) 0.1625(16) 0.0163(12) 0.065(4) Uani 0.50 1 d P B 2 O1' O 0.7498(18) 0.849(3) 0.0211(11) 0.061(5) Uani 0.50 1 d P A 3 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 0.0411(2) 0.02080(15) 0.02358(17) 0.00250(9) -0.00072(12) -0.00643(10) N3 0.0433(12) 0.0199(8) 0.0211(10) 0.0015(7) 0.0009(8) -0.0043(8) C13 0.0331(12) 0.0206(9) 0.0251(11) -0.0010(8) 0.0019(9) -0.0015(8) C12 0.0317(11) 0.0235(9) 0.0214(10) -0.0014(8) 0.0005(9) 0.0009(8) C11 0.0383(13) 0.0217(9) 0.0239(11) 0.0005(8) 0.0020(10) 0.0013(8) C9 0.0396(12) 0.0200(9) 0.0188(10) -0.0037(8) 0.0013(9) -0.0010(8) C8 0.0347(12) 0.0195(9) 0.0213(10) 0.0012(7) 0.0016(9) 0.0014(8) C10 0.0419(13) 0.0160(8) 0.0258(11) -0.0022(8) 0.0027(10) -0.0002(8) O2W 0.53(2) 0.196(7) 0.155(8) 0.046(6) 0.108(10) 0.012(9) O1W 0.334(14) 0.499(16) 0.184(9) 0.080(10) 0.049(9) 0.282(13) C14 0.0504(15) 0.0202(10) 0.0304(13) -0.0017(9) 0.0033(11) -0.0042(9) O2 0.0463(10) 0.0209(7) 0.0305(9) -0.0034(6) -0.0003(8) -0.0058(7) O1 0.067(4) 0.018(2) 0.022(3) 0.002(2) 0.008(3) -0.002(2) C15 0.0326(12) 0.0289(10) 0.0241(11) 0.0004(8) -0.0002(9) 0.0017(9) O4 0.0473(11) 0.0332(9) 0.0244(9) 0.0051(7) -0.0050(8) -0.0009(7) O3 0.0590(13) 0.0365(10) 0.0307(10) -0.0015(8) -0.0067(9) -0.0134(9) C7 0.115(8) 0.111(8) 0.056(5) 0.027(5) 0.008(5) -0.074(7) N1 0.0445(14) 0.0684(17) 0.0384(14) 0.0165(12) 0.0056(11) -0.0113(12) N2 0.044(3) 0.097(5) 0.054(4) 0.026(3) 0.006(3) -0.014(3) C1 0.061(5) 0.183(12) 0.069(6) 0.050(7) 0.011(4) -0.045(7) C2 0.066(6) 0.091(7) 0.045(7) 0.030(5) 0.015(5) -0.047(5) C3 0.044(4) 0.027(4) 0.026(4) -0.002(3) 0.010(3) -0.013(3) N2' 0.062(4) 0.062(3) 0.059(4) 0.017(3) 0.012(3) -0.022(3) C1' 0.056(4) 0.074(5) 0.053(4) 0.015(4) 0.022(3) -0.024(4) C2' 0.135(18) 0.166(16) 0.034(6) -0.027(7) 0.018(8) -0.066(12) C3' 0.114(9) 0.045(7) 0.042(5) -0.012(5) 0.036(5) -0.024(6) O1' 0.113(11) 0.026(4) 0.042(5) -0.003(3) 0.026(4) -0.019(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O4 1.9389(19) 4_666 ? Zn1 O2 1.9762(16) 1_545 ? Zn1 N1 1.998(3) . ? Zn1 N3 2.068(2) . ? N3 C8 1.443(3) . ? N3 H3AB 0.97(4) . ? N3 H3AA 0.88(3) . ? C13 C8 1.388(3) . ? C13 C12 1.392(3) . ? C13 H13A 0.9300 . ? C12 C11 1.391(3) . ? C12 C15 1.503(3) . ? C11 C10 1.388(3) . ? C11 H11 0.9300 . ? C9 C8 1.388(3) . ? C9 C10 1.390(3) . ? C9 H8A 0.9300 . ? C10 C14 1.496(3) . ? O2W H2WB 1.0507 . ? O2W H2WA 0.9732 . ? C14 O1 1.231(15) . ? C14 O2 1.275(3) . ? C14 O1' 1.281(19) . ? O2 Zn1 1.9762(16) 1_565 ? C15 O3 1.233(3) . ? C15 O4 1.280(3) . ? O4 Zn1 1.9389(19) 4_565 ? C7 C2 1.474(14) . ? N1 C3 1.300(14) . ? N1 N2 1.362(6) . ? N2 C1 1.332(10) . ? C1 C2 1.40(2) . ? C2 C3 1.368(16) . ? N2' C1' 1.405(8) . ? C1' C2' 1.43(2) . ? C2' C3' 1.33(2) . ? 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 O2 101.57(7) 4_666 1_545 ? O4 Zn1 N1 103.25(10) 4_666 . ? O2 Zn1 N1 124.55(11) 1_545 . ? O4 Zn1 N3 114.35(9) 4_666 . ? O2 Zn1 N3 103.22(8) 1_545 . ? N1 Zn1 N3 110.07(10) . . ? C8 N3 Zn1 110.51(16) . . ? C8 N3 H3AB 114(3) . . ? Zn1 N3 H3AB 103(2) . . ? C8 N3 H3AA 113(2) . . ? Zn1 N3 H3AA 101(2) . . ? H3AB N3 H3AA 114(3) . . ? C8 C13 C12 119.8(2) . . ? C8 C13 H13A 120.1 . . ? C12 C13 H13A 120.1 . . ? C11 C12 C13 119.9(2) . . ? C11 C12 C15 119.9(2) . . ? C13 C12 C15 120.12(19) . . ? C10 C11 C12 120.1(2) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C8 C9 C10 119.9(2) . . ? C8 C9 H8A 120.1 . . ? C10 C9 H8A 120.1 . . ? C13 C8 C9 120.3(2) . . ? C13 C8 N3 121.59(19) . . ? C9 C8 N3 117.99(19) . . ? C11 C10 C9 120.0(2) . . ? C11 C10 C14 120.0(2) . . ? C9 C10 C14 120.0(2) . . ? H2WB O2W H2WA 101.9 . . ? O1 C14 O2 120.8(8) . . ? O1 C14 O1' 17.1(14) . . ? O2 C14 O1' 123.1(9) . . ? O1 C14 C10 120.6(8) . . ? O2 C14 C10 117.8(2) . . ? O1' C14 C10 118.5(9) . . ? C14 O2 Zn1 105.23(14) . 1_565 ? O3 C15 O4 124.4(2) . . ? O3 C15 C12 120.7(2) . . ? O4 C15 C12 114.9(2) . . ? C15 O4 Zn1 124.81(16) . 4_565 ? C3 N1 N2 105.1(6) . . ? C3 N1 Zn1 131.5(5) . . ? N2 N1 Zn1 122.2(3) . . ? C1 N2 N1 109.3(6) . . ? N2 C1 C2 108.0(8) . . ? C3 C2 C1 102.5(9) . . ? C3 C2 C7 127.1(14) . . ? C1 C2 C7 128.7(12) . . ? N1 C3 C2 112.4(10) . . ? N2' C1' C2' 100.3(9) . . ? C3' C2' C1' 112.3(14) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 31.78 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.884 _refine_diff_density_min -0.566 _refine_diff_density_rms 0.100 _database_code_depnum_ccdc_archive 'CCDC 873743' ####################################################################### # # 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_12ssg003 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H34 N14 O11 Zn2' _chemical_formula_weight 933.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.361(3) _cell_length_b 10.108(3) _cell_length_c 11.470(4) _cell_angle_alpha 95.845(12) _cell_angle_beta 112.739(10) _cell_angle_gamma 97.487(12) _cell_volume 978.5(5) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2224 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 31.12 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 478 _exptl_absorpt_coefficient_mu 1.303 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.323739 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.1948 before correction' _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 APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12402 _diffrn_reflns_av_R_equivalents 0.0633 _diffrn_reflns_av_sigmaI/netI 0.0717 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4122 _reflns_number_gt 2754 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. One of the methanol molecule shows a positional disorder for the carbon atom with 50% site occupency for both the components.The hydrogen atoms for both methanol molecules could not be located in the data and therefore have not been included in the refinement. This has led to a difference in calculated and reported formula and consequent alerts in the cif check. ; _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^)+(0.0912P)^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 4122 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1574 _refine_ls_wR_factor_gt 0.1411 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _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 0.41174(5) 0.50202(4) 0.28759(4) 0.0418(2) Uani 1 1 d . . . O1 O 0.5417(3) 0.3742(3) 0.3757(3) 0.0489(7) Uani 1 1 d . . . N1 N 0.2131(4) 0.4767(3) 0.3183(3) 0.0436(8) Uani 1 1 d . . . C14 C 0.4821(5) 0.2512(4) 0.3295(4) 0.0497(10) Uani 1 1 d . . . N2 N 0.1867(4) 0.4042(3) 0.4021(3) 0.0477(8) Uani 1 1 d . . . H2A H 0.2572 0.3700 0.4576 0.057 Uiso 1 1 calc R . . O2 O 0.3528(4) 0.2133(3) 0.2385(4) 0.0881(13) Uani 1 1 d . . . C8 C 0.5755(5) 0.1460(4) 0.3880(4) 0.0411(9) Uani 1 1 d . . . C1 C 0.0753(5) 0.5097(5) 0.2517(4) 0.0497(10) Uani 1 1 d . . . H1A H 0.0581 0.5609 0.1862 0.060 Uiso 1 1 calc R . . C9 C 0.5056(5) 0.0097(4) 0.3408(4) 0.0453(10) Uani 1 1 d . . . H9A H 0.4041 -0.0125 0.2767 0.054 Uiso 1 1 calc R . . C13 C 0.7206(5) 0.1821(4) 0.4851(4) 0.0506(10) Uani 1 1 d . . . H13A H 0.7650 0.2729 0.5176 0.061 Uiso 1 1 calc R . . C2 C -0.0384(5) 0.4589(5) 0.2911(4) 0.0494(10) Uani 1 1 d . . . C3 C 0.0389(5) 0.3920(5) 0.3883(4) 0.0532(11) Uani 1 1 d . . . H3A H -0.0052 0.3460 0.4361 0.064 Uiso 1 1 calc R . . C12 C 0.8032(6) 0.0798(5) 0.5362(5) 0.0672(14) Uani 1 1 d . . . N6 N 1.0227(6) 0.0300(6) 0.6832(6) 0.109(2) Uani 1 1 d . . . N5 N 0.9550(7) 0.1214(5) 0.6309(6) 0.117(2) Uani 1 1 d . . . N7 N 1.0964(8) -0.0435(7) 0.7306(7) 0.144(3) Uani 1 1 d . . . O1S O 0.5000 1.0000 0.0000 0.258(7) Uani 1 2 d S . . C10 C 0.5842(5) -0.0916(4) 0.3874(4) 0.0442(10) Uani 1 1 d . . . C11 C 0.7345(6) -0.0586(5) 0.4874(5) 0.0654(13) Uani 1 1 d . . . H11A H 0.7884 -0.1262 0.5214 0.078 Uiso 1 1 calc R . . C15 C 0.5027(5) -0.2360(4) 0.3362(4) 0.0432(9) Uani 1 1 d . . . O3 O 0.5770(3) -0.3297(3) 0.3829(3) 0.0483(7) Uani 1 1 d . . . O4 O 0.3670(4) -0.2631(3) 0.2525(3) 0.0582(8) Uani 1 1 d . . . C7 C -0.2111(6) 0.4734(7) 0.2410(5) 0.0826(19) Uani 1 1 d . . . H7A H -0.2759 0.3859 0.2295 0.099 Uiso 1 1 calc R . . H7B H -0.2264 0.5347 0.3042 0.099 Uiso 1 1 calc R . . C5 C -0.2644(5) 0.5263(6) 0.1153(4) 0.0578(12) Uani 1 1 d . . . C4 C -0.3107(5) 0.4550(5) -0.0060(4) 0.0564(12) Uani 1 1 d . . . H4A H -0.3157 0.3622 -0.0239 0.068 Uiso 1 1 calc R . . C6 C -0.2736(7) 0.6546(6) 0.0958(5) 0.0842(18) Uani 1 1 d . . . H6A H -0.2493 0.7289 0.1595 0.101 Uiso 1 1 calc R . . N3 N -0.3475(4) 0.5346(3) -0.0947(3) 0.0471(8) Uani 1 1 d . . . N4 N -0.3230(5) 0.6583(4) -0.0293(4) 0.0686(12) Uani 1 1 d . . . H4B H -0.3371 0.7303 -0.0631 0.082 Uiso 1 1 calc R . . C2S C 0.0250(15) 0.801(2) -0.0048(16) 0.265(9) Uani 1 1 d . . . C1S C 0.627(2) 0.9398(14) -0.0044(16) 0.107(5) Uani 0.50 1 d P . . O2S O 0.1579(19) 0.8575(12) 0.0649(14) 0.382(10) 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 0.0321(3) 0.0432(3) 0.0445(3) 0.00784(19) 0.0087(2) 0.00908(19) O1 0.0512(18) 0.0339(14) 0.0605(18) 0.0114(12) 0.0194(14) 0.0114(12) N1 0.0344(18) 0.0479(19) 0.0470(19) 0.0134(15) 0.0125(15) 0.0114(15) C14 0.043(2) 0.045(2) 0.065(3) 0.016(2) 0.022(2) 0.0128(19) N2 0.042(2) 0.052(2) 0.049(2) 0.0179(16) 0.0147(16) 0.0153(16) O2 0.067(2) 0.055(2) 0.098(3) 0.0234(19) -0.015(2) 0.0079(17) C8 0.045(2) 0.038(2) 0.049(2) 0.0147(17) 0.025(2) 0.0135(17) C1 0.037(2) 0.072(3) 0.043(2) 0.021(2) 0.0136(19) 0.018(2) C9 0.046(2) 0.039(2) 0.048(2) 0.0095(17) 0.016(2) 0.0084(17) C13 0.043(2) 0.047(2) 0.058(3) 0.0103(19) 0.016(2) 0.0094(19) C2 0.036(2) 0.078(3) 0.035(2) 0.011(2) 0.0139(18) 0.014(2) C3 0.047(3) 0.069(3) 0.046(2) 0.014(2) 0.020(2) 0.010(2) C12 0.047(3) 0.073(3) 0.066(3) 0.015(3) 0.006(2) 0.010(2) N6 0.080(4) 0.084(4) 0.109(4) 0.009(3) -0.019(3) 0.023(3) N5 0.093(4) 0.071(3) 0.129(5) -0.002(3) -0.011(4) 0.011(3) N7 0.120(6) 0.119(5) 0.131(6) 0.035(4) -0.023(4) 0.043(4) O1S 0.210(13) 0.38(2) 0.217(14) 0.052(13) 0.109(11) 0.103(15) C10 0.044(2) 0.036(2) 0.052(2) 0.0122(17) 0.017(2) 0.0104(17) C11 0.068(3) 0.049(3) 0.078(3) 0.017(2) 0.025(3) 0.017(2) C15 0.051(3) 0.037(2) 0.047(2) 0.0118(17) 0.024(2) 0.0102(18) O3 0.0499(17) 0.0374(14) 0.0538(17) 0.0139(12) 0.0134(14) 0.0141(12) O4 0.0528(19) 0.0440(16) 0.0617(19) 0.0066(14) 0.0070(16) 0.0081(14) C7 0.046(3) 0.162(6) 0.049(3) 0.038(3) 0.021(2) 0.028(3) C5 0.029(2) 0.098(4) 0.047(3) 0.013(2) 0.0134(19) 0.016(2) C4 0.047(3) 0.074(3) 0.052(3) 0.019(2) 0.017(2) 0.025(2) C6 0.085(4) 0.091(4) 0.049(3) -0.011(3) 0.006(3) 0.008(3) N3 0.0403(19) 0.054(2) 0.0420(19) 0.0055(15) 0.0114(16) 0.0096(16) N4 0.079(3) 0.056(2) 0.051(2) 0.0019(18) 0.009(2) 0.006(2) C2S 0.112(9) 0.35(2) 0.251(17) -0.038(15) 0.036(10) -0.048(11) C1S 0.132(13) 0.080(9) 0.131(12) 0.023(8) 0.070(11) 0.038(9) O2S 0.388(19) 0.176(9) 0.353(17) 0.040(10) -0.085(14) 0.029(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 O1 1.973(3) . ? Zn1 N1 2.012(3) . ? Zn1 O3 2.027(3) 1_565 ? Zn1 N3 2.035(3) 2_565 ? O1 C14 1.263(5) . ? N1 C1 1.327(5) . ? N1 N2 1.342(4) . ? C14 O2 1.234(5) . ? C14 C8 1.510(5) . ? N2 C3 1.318(5) . ? N2 H2A 0.8600 . ? C8 C13 1.355(6) . ? C8 C9 1.400(5) . ? C1 C2 1.370(6) . ? C1 H1A 0.9300 . ? C9 C10 1.371(5) . ? C9 H9A 0.9300 . ? C13 C12 1.412(6) . ? C13 H13A 0.9300 . ? C2 C3 1.372(6) . ? C2 C7 1.525(6) . ? C3 H3A 0.9300 . ? C12 N5 1.391(7) . ? C12 C11 1.418(7) . ? N6 N7 1.118(8) . ? N6 N5 1.260(7) . ? O1S C1S 1.418(16) . ? O1S C1S 1.418(16) 2_675 ? C10 C11 1.400(6) . ? C10 C15 1.498(5) . ? C11 H11A 0.9300 . ? C15 O4 1.234(5) . ? C15 O3 1.287(5) . ? O3 Zn1 2.027(3) 1_545 ? C7 C5 1.511(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C5 C6 1.347(8) . ? C5 C4 1.375(7) . ? C4 N3 1.330(5) . ? C4 H4A 0.9300 . ? C6 N4 1.333(6) . ? C6 H6A 0.9300 . ? N3 N4 1.334(5) . ? N3 Zn1 2.035(3) 2_565 ? N4 H4B 0.8600 . ? C2S O2S 1.211(14) . ? 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 N1 107.78(13) . . ? O1 Zn1 O3 95.29(11) . 1_565 ? N1 Zn1 O3 118.11(13) . 1_565 ? O1 Zn1 N3 112.09(13) . 2_565 ? N1 Zn1 N3 107.49(13) . 2_565 ? O3 Zn1 N3 115.38(13) 1_565 2_565 ? C14 O1 Zn1 114.2(3) . . ? C1 N1 N2 104.9(3) . . ? C1 N1 Zn1 128.8(3) . . ? N2 N1 Zn1 125.7(2) . . ? O2 C14 O1 123.3(4) . . ? O2 C14 C8 118.7(4) . . ? O1 C14 C8 118.0(4) . . ? C3 N2 N1 111.3(3) . . ? C3 N2 H2A 124.3 . . ? N1 N2 H2A 124.3 . . ? C13 C8 C9 121.0(4) . . ? C13 C8 C14 121.2(4) . . ? C9 C8 C14 117.8(4) . . ? N1 C1 C2 111.7(4) . . ? N1 C1 H1A 124.2 . . ? C2 C1 H1A 124.2 . . ? C10 C9 C8 121.2(4) . . ? C10 C9 H9A 119.4 . . ? C8 C9 H9A 119.4 . . ? C8 C13 C12 119.0(4) . . ? C8 C13 H13A 120.5 . . ? C12 C13 H13A 120.5 . . ? C1 C2 C3 104.1(4) . . ? C1 C2 C7 128.8(4) . . ? C3 C2 C7 127.2(4) . . ? N2 C3 C2 108.1(4) . . ? N2 C3 H3A 126.0 . . ? C2 C3 H3A 126.0 . . ? N5 C12 C13 117.0(5) . . ? N5 C12 C11 122.5(5) . . ? C13 C12 C11 120.4(4) . . ? N7 N6 N5 173.0(9) . . ? N6 N5 C12 116.5(5) . . ? C1S O1S C1S 180.0(14) . 2_675 ? C9 C10 C11 119.5(4) . . ? C9 C10 C15 119.2(4) . . ? C11 C10 C15 121.2(4) . . ? C10 C11 C12 118.8(4) . . ? C10 C11 H11A 120.6 . . ? C12 C11 H11A 120.6 . . ? O4 C15 O3 121.4(4) . . ? O4 C15 C10 120.3(4) . . ? O3 C15 C10 118.3(4) . . ? C15 O3 Zn1 101.4(2) . 1_545 ? C5 C7 C2 112.3(4) . . ? C5 C7 H7A 109.1 . . ? C2 C7 H7A 109.1 . . ? C5 C7 H7B 109.1 . . ? C2 C7 H7B 109.1 . . ? H7A C7 H7B 107.9 . . ? C6 C5 C4 103.6(4) . . ? C6 C5 C7 128.3(5) . . ? C4 C5 C7 128.0(5) . . ? N3 C4 C5 111.9(5) . . ? N3 C4 H4A 124.1 . . ? C5 C4 H4A 124.1 . . ? N4 C6 C5 109.2(5) . . ? N4 C6 H6A 125.4 . . ? C5 C6 H6A 125.4 . . ? C4 N3 N4 104.9(4) . . ? C4 N3 Zn1 132.2(3) . 2_565 ? N4 N3 Zn1 122.8(3) . 2_565 ? C6 N4 N3 110.4(4) . . ? C6 N4 H4B 124.8 . . ? N3 N4 H4B 124.8 . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.703 _refine_diff_density_min -0.522 _refine_diff_density_rms 0.089 _database_code_depnum_ccdc_archive 'CCDC 873744' ####################################################################### # # 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_12ssg006_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H13 N7 O5 Zn' _chemical_formula_weight 436.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.446(2) _cell_length_b 14.595(4) _cell_length_c 13.058(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.624(8) _cell_angle_gamma 90.00 _cell_volume 1775.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2609 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 30.08 _exptl_crystal_description Block _exptl_crystal_colour Violet _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 1.429 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.799783 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0582 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 25315 _diffrn_reflns_av_R_equivalents 0.0708 _diffrn_reflns_av_sigmaI/netI 0.0808 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 30.09 _reflns_number_total 5050 _reflns_number_gt 2097 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Two nitrogen atoms (N6 and N7) of the azide group show some positional disorder with 70% occupency for the major components and minor components with 30% site occupency. The tharmal ellipsoids of the non coordinating water molecule is relatively large in size, but we could not find any satisfactory disorder model. ; _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^)+(0.1000P)^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 5050 _refine_ls_number_parameters 261 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1824 _refine_ls_R_factor_gt 0.0773 _refine_ls_wR_factor_ref 0.2444 _refine_ls_wR_factor_gt 0.2065 _refine_ls_goodness_of_fit_ref 1.172 _refine_ls_restrained_S_all 1.192 _refine_ls_shift/su_max 0.003 _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 0.27500(7) 0.18614(5) 0.65980(4) 0.0759(3) Uani 1 1 d . . . O2 O 0.1557(6) 0.3176(3) 0.4981(3) 0.0972(14) Uani 1 1 d . . . O1 O 0.3237(5) 0.3132(3) 0.6379(3) 0.0885(12) Uani 1 1 d . . . N2 N 0.0337(5) 0.1639(3) 0.7832(3) 0.0730(12) Uani 1 1 d . . . H2A H 0.0881 0.1751 0.8415 0.088 Uiso 1 1 calc R . . N1 N 0.0766(5) 0.1671(3) 0.6903(3) 0.0747(12) Uani 1 1 d . . . C8 C 0.2877(6) 0.4529(4) 0.5480(4) 0.0715(15) Uani 1 1 d . . . C2 C -0.1579(6) 0.1284(4) 0.6698(4) 0.0682(13) Uani 1 1 d . . . C14 C 0.2533(7) 0.3545(4) 0.5613(4) 0.0740(15) Uani 1 1 d . . . C1 C -0.0385(6) 0.1472(4) 0.6242(4) 0.0798(16) Uani 1 1 d . . . H1A H -0.0404 0.1457 0.5528 0.096 Uiso 1 1 calc R . . C7 C -0.3048(6) 0.1003(4) 0.6195(5) 0.0826(17) Uani 1 1 d . . . H7A H -0.3399 0.1430 0.5641 0.099 Uiso 1 1 calc R . . H7B H -0.3689 0.1031 0.6702 0.099 Uiso 1 1 calc R . . C12 C 0.2575(9) 0.5913(5) 0.4498(6) 0.103(2) Uani 1 1 d . A . C9 C 0.4012(6) 0.4937(4) 0.6126(4) 0.0792(16) Uani 1 1 d . . . H9A H 0.4514 0.4605 0.6678 0.095 Uiso 1 1 calc R . . C13 C 0.2142(6) 0.5037(4) 0.4675(4) 0.0812(16) Uani 1 1 d . . . H13A H 0.1349 0.4787 0.4249 0.097 Uiso 1 1 calc R . . C3 C -0.1043(7) 0.1412(5) 0.7726(4) 0.0845(17) Uani 1 1 d . . . H3A H -0.1562 0.1350 0.8268 0.101 Uiso 1 1 calc R . . C11 C 0.3735(7) 0.6322(5) 0.5127(6) 0.0964(19) Uani 1 1 d . . . H11A H 0.4038 0.6908 0.4983 0.116 Uiso 1 1 calc R . . C10 C 0.4416(7) 0.5839(4) 0.5964(5) 0.0845(19) Uani 1 1 d . . . N5 N 0.1927(11) 0.6467(5) 0.3655(8) 0.153(3) Uani 1 1 d . . . C5 C -0.3070(5) 0.0057(5) 0.5759(4) 0.0752(16) Uani 1 1 d . . . C4 C -0.2873(6) -0.0210(5) 0.4784(4) 0.0778(16) Uani 1 1 d . . . H4A H -0.2732 0.0200 0.4265 0.093 Uiso 1 1 calc R . . C6 C -0.3250(6) -0.0763(5) 0.6234(5) 0.0867(17) Uani 1 1 d . . . H6A H -0.3416 -0.0832 0.6912 0.104 Uiso 1 1 calc R . . N4 N -0.3150(5) -0.1435(4) 0.5580(4) 0.0792(13) Uani 1 1 d . . . H4B H -0.3231 -0.2006 0.5718 0.095 Uiso 1 1 calc R . . N3 N -0.2903(5) -0.1105(4) 0.4660(3) 0.0758(12) Uani 1 1 d . . . C15 C 0.5614(7) 0.6276(6) 0.6694(6) 0.097(2) Uani 1 1 d . . . O3 O 0.5930(7) 0.5940(5) 0.7509(4) 0.160(3) Uani 1 1 d . . . O4 O 0.6147(7) 0.6975(4) 0.6464(6) 0.160(3) Uani 1 1 d . . . N6 N 0.090(2) 0.6184(9) 0.3083(17) 0.148(7) Uani 0.70 1 d P A 1 N7 N 0.023(3) 0.5865(13) 0.2222(17) 0.228(12) Uani 0.70 1 d P A 1 N7' N -0.012(4) 0.610(2) 0.289(3) 0.123(10) Uani 0.30 1 d P A 2 N6' N 0.124(5) 0.591(3) 0.286(3) 0.131(15) Uiso 0.30 1 d P A 2 O1W O 0.365(5) 0.6416(14) 0.220(2) 0.67(2) Uiso 1 1 d D . . H1WA H 0.3766 0.5766 0.2405 0.802 Uiso 1 1 d D . . H1WB H 0.3575 0.6840 0.1732 0.802 Uiso 1 1 d 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 0.0673(5) 0.0969(6) 0.0590(4) 0.0122(3) -0.0030(3) -0.0124(3) O2 0.129(4) 0.088(3) 0.063(2) 0.002(2) -0.018(2) -0.039(2) O1 0.100(3) 0.105(3) 0.055(2) 0.001(2) -0.004(2) -0.035(2) N2 0.073(3) 0.092(3) 0.053(3) 0.002(2) 0.004(2) 0.013(2) N1 0.066(3) 0.100(3) 0.057(3) 0.007(2) 0.004(2) -0.008(2) C8 0.077(3) 0.091(4) 0.047(3) -0.016(3) 0.014(3) -0.036(3) C2 0.062(3) 0.082(4) 0.061(3) 0.004(3) 0.012(2) 0.018(3) C14 0.081(4) 0.087(4) 0.051(3) -0.008(3) 0.005(3) -0.025(3) C1 0.075(4) 0.114(5) 0.051(3) -0.001(3) 0.013(3) -0.002(3) C7 0.053(3) 0.112(5) 0.082(4) 0.006(3) 0.008(3) 0.019(3) C12 0.110(5) 0.087(5) 0.110(5) -0.007(4) 0.013(4) -0.010(4) C9 0.092(4) 0.099(4) 0.049(3) -0.010(3) 0.020(3) -0.040(3) C13 0.086(4) 0.085(4) 0.071(4) -0.015(3) 0.009(3) -0.029(3) C3 0.077(4) 0.117(5) 0.063(4) 0.009(3) 0.021(3) 0.025(4) C11 0.092(5) 0.090(5) 0.104(5) -0.015(4) 0.008(4) -0.030(4) C10 0.090(4) 0.107(5) 0.065(3) -0.034(3) 0.040(3) -0.052(4) N5 0.139(7) 0.104(5) 0.194(8) 0.019(6) -0.032(6) -0.026(5) C5 0.039(2) 0.123(5) 0.061(3) 0.007(3) 0.002(2) 0.011(3) C4 0.065(3) 0.107(5) 0.062(3) 0.023(3) 0.014(3) 0.012(3) C6 0.075(4) 0.121(5) 0.064(3) 0.010(4) 0.012(3) 0.007(4) N4 0.064(3) 0.104(4) 0.068(3) 0.021(3) 0.007(2) -0.005(3) N3 0.071(3) 0.096(4) 0.059(3) 0.019(2) 0.007(2) 0.001(3) C15 0.087(4) 0.133(6) 0.081(4) -0.028(4) 0.043(4) -0.054(4) O3 0.190(6) 0.199(6) 0.079(3) 0.028(4) -0.015(3) -0.127(5) O4 0.124(4) 0.110(4) 0.233(8) -0.013(4) -0.008(5) -0.061(3) N6 0.097(11) 0.076(8) 0.25(2) 0.033(10) -0.030(11) 0.007(8) N7 0.22(2) 0.156(15) 0.24(2) -0.014(13) -0.154(19) -0.013(13) N7' 0.090(17) 0.085(16) 0.18(3) -0.024(17) -0.02(2) 0.010(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.944(4) . ? Zn1 N1 1.999(5) . ? Zn1 N3 2.005(5) 3_556 ? Zn1 O3 2.059(5) 2_646 ? O2 C14 1.252(7) . ? O1 C14 1.258(7) . ? N2 C3 1.330(8) . ? N2 N1 1.343(6) . ? N2 H2A 0.8600 . ? N1 C1 1.302(7) . ? C8 C13 1.376(8) . ? C8 C9 1.383(7) . ? C8 C14 1.490(8) . ? C2 C3 1.367(7) . ? C2 C1 1.388(7) . ? C2 C7 1.491(8) . ? C1 H1A 0.9300 . ? C7 C5 1.492(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C12 C13 1.373(9) . ? C12 C11 1.390(10) . ? C12 N5 1.419(10) . ? C9 C10 1.398(8) . ? C9 H9A 0.9300 . ? C13 H13A 0.9300 . ? C3 H3A 0.9300 . ? C11 C10 1.368(9) . ? C11 H11A 0.9300 . ? C10 C15 1.495(8) . ? N5 N6 1.193(17) . ? N5 N6' 1.39(4) . ? C5 C6 1.372(8) . ? C5 C4 1.373(7) . ? C4 N3 1.316(7) . ? C4 H4A 0.9300 . ? C6 N4 1.315(8) . ? C6 H6A 0.9300 . ? N4 N3 1.349(6) . ? N4 H4B 0.8600 . ? N3 Zn1 2.005(5) 3_556 ? C15 O3 1.165(8) . ? C15 O4 1.198(8) . ? O3 Zn1 2.059(5) 2_656 ? N6 N7 1.28(3) . ? N7' N6' 1.32(5) . ? O1W H1WA 0.9851 . ? O1W H1WB 0.8681 . ? 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 N1 114.5(2) . . ? O1 Zn1 N3 110.71(19) . 3_556 ? N1 Zn1 N3 106.57(19) . 3_556 ? O1 Zn1 O3 124.8(3) . 2_646 ? N1 Zn1 O3 107.2(3) . 2_646 ? N3 Zn1 O3 89.1(2) 3_556 2_646 ? C14 O1 Zn1 117.8(3) . . ? C3 N2 N1 110.7(5) . . ? C3 N2 H2A 124.6 . . ? N1 N2 H2A 124.6 . . ? C1 N1 N2 104.3(4) . . ? C1 N1 Zn1 127.3(4) . . ? N2 N1 Zn1 128.2(4) . . ? C13 C8 C9 118.4(5) . . ? C13 C8 C14 121.1(5) . . ? C9 C8 C14 120.4(5) . . ? C3 C2 C1 101.6(5) . . ? C3 C2 C7 129.5(5) . . ? C1 C2 C7 129.0(5) . . ? O2 C14 O1 123.5(5) . . ? O2 C14 C8 119.3(5) . . ? O1 C14 C8 117.2(5) . . ? N1 C1 C2 114.1(5) . . ? N1 C1 H1A 123.0 . . ? C2 C1 H1A 123.0 . . ? C2 C7 C5 112.0(4) . . ? C2 C7 H7A 109.2 . . ? C5 C7 H7A 109.2 . . ? C2 C7 H7B 109.2 . . ? C5 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C13 C12 C11 121.9(7) . . ? C13 C12 N5 124.0(7) . . ? C11 C12 N5 114.1(7) . . ? C8 C9 C10 121.1(6) . . ? C8 C9 H9A 119.5 . . ? C10 C9 H9A 119.5 . . ? C12 C13 C8 120.2(6) . . ? C12 C13 H13A 119.9 . . ? C8 C13 H13A 119.9 . . ? N2 C3 C2 109.4(5) . . ? N2 C3 H3A 125.3 . . ? C2 C3 H3A 125.3 . . ? C10 C11 C12 118.0(6) . . ? C10 C11 H11A 121.0 . . ? C12 C11 H11A 121.0 . . ? C11 C10 C9 120.2(5) . . ? C11 C10 C15 119.6(6) . . ? C9 C10 C15 120.2(7) . . ? N6 N5 N6' 26.1(18) . . ? N6 N5 C12 119.2(9) . . ? N6' N5 C12 109.2(17) . . ? C6 C5 C4 102.6(6) . . ? C6 C5 C7 129.0(6) . . ? C4 C5 C7 128.4(6) . . ? N3 C4 C5 113.1(5) . . ? N3 C4 H4A 123.5 . . ? C5 C4 H4A 123.5 . . ? N4 C6 C5 109.2(5) . . ? N4 C6 H6A 125.4 . . ? C5 C6 H6A 125.4 . . ? C6 N4 N3 110.7(5) . . ? C6 N4 H4B 124.6 . . ? N3 N4 H4B 124.6 . . ? C4 N3 N4 104.4(5) . . ? C4 N3 Zn1 130.1(4) . 3_556 ? N4 N3 Zn1 125.4(4) . 3_556 ? O3 C15 O4 122.3(7) . . ? O3 C15 C10 117.0(6) . . ? O4 C15 C10 120.5(8) . . ? C15 O3 Zn1 106.3(5) . 2_656 ? N5 N6 N7 155(3) . . ? N7' N6' N5 101(3) . . ? H1WA O1W H1WB 150.1 . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 30.09 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 1.022 _refine_diff_density_min -0.667 _refine_diff_density_rms 0.086 _database_code_depnum_ccdc_archive 'CCDC 873745'