# Electronic Supplementary Material (ESI) for Chemical Communications # 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_cmpd1_k12mfm1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 N2 O7 Zn1.50' _chemical_formula_weight 473.41 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7750(1) _cell_length_b 18.9580(2) _cell_length_c 11.4690(1) _cell_angle_alpha 90.00 _cell_angle_beta 111.3540(10) _cell_angle_gamma 90.00 _cell_volume 1979.46(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 23681 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description tabloid _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 1.874 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.576 _exptl_absorpt_correction_T_max 0.693 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36699 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4533 _reflns_number_gt 4079 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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 asymmetric unit comprises 1 full zinc centre (Zn2), half of a zinc centre (Zn1,located at a crystallographic inversion centre), one bdc ligand, one deferiprone ligand and one molecule of DMF. ; _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^)+(0.0267P)^2^+1.2008P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0043(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4533 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0248 _refine_ls_wR_factor_ref 0.0618 _refine_ls_wR_factor_gt 0.0593 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.0000 0.0000 0.5000 0.01063(7) Uani 1 2 d S . . Zn2 Zn 0.364991(18) -0.005567(8) 0.546540(15) 0.01086(7) Uani 1 1 d . . . O1 O 0.36148(12) 0.07760(6) 0.65014(10) 0.0194(2) Uani 1 1 d . . . O2 O 0.13669(12) 0.05859(6) 0.65517(10) 0.0183(2) Uani 1 1 d . . . O3 O 0.16235(12) 0.39950(5) 0.89576(11) 0.0195(2) Uani 1 1 d . . . O4 O 0.40361(12) 0.40315(5) 0.92753(11) 0.0199(2) Uani 1 1 d . . . O5 O 0.40641(11) 0.00979(5) 0.38635(10) 0.0149(2) Uani 1 1 d . . . O6 O 0.15512(11) 0.01280(5) 0.41942(10) 0.0144(2) Uani 1 1 d . . . O7 O -0.18857(18) 0.13998(8) -0.15288(14) 0.0505(4) Uani 1 1 d . . . N1 N 0.16225(14) 0.06785(7) 0.07934(11) 0.0185(3) Uani 1 1 d . . . N2 N -0.32485(17) 0.21428(8) -0.30525(14) 0.0279(3) Uani 1 1 d . . . C1 C 0.24942(16) 0.09492(7) 0.67498(13) 0.0146(3) Uani 1 1 d . . . C2 C 0.25741(17) 0.16627(8) 0.73526(14) 0.0156(3) Uani 1 1 d . . . C3 C 0.39257(17) 0.19526(8) 0.80759(16) 0.0212(3) Uani 1 1 d . . . H3 H 0.4802 0.1694 0.8209 0.025 Uiso 1 1 calc R . . C4 C 0.40009(17) 0.26172(8) 0.86040(16) 0.0214(3) Uani 1 1 d . . . H4 H 0.4927 0.2811 0.9099 0.026 Uiso 1 1 calc R . . C5 C 0.27176(17) 0.30006(8) 0.84077(14) 0.0167(3) Uani 1 1 d . . . C6 C 0.13642(17) 0.27034(8) 0.77029(15) 0.0195(3) Uani 1 1 d . . . H6 H 0.0487 0.2959 0.7580 0.023 Uiso 1 1 calc R . . C7 C 0.12848(17) 0.20365(8) 0.71786(14) 0.0180(3) Uani 1 1 d . . . H7 H 0.0358 0.1836 0.6704 0.022 Uiso 1 1 calc R . . C8 C 0.28135(16) 0.37369(8) 0.89317(13) 0.0155(3) Uani 1 1 d . . . C9 C 0.28873(16) 0.02960(7) 0.28915(13) 0.0138(3) Uani 1 1 d . . . C10 C 0.15200(16) 0.03157(7) 0.30963(13) 0.0138(3) Uani 1 1 d . . . C11 C 0.02554(16) 0.05347(8) 0.21095(14) 0.0180(3) Uani 1 1 d . . . H11 H -0.0661 0.0555 0.2221 0.022 Uiso 1 1 calc R . . C12 C 0.03413(17) 0.07199(8) 0.09859(14) 0.0200(3) Uani 1 1 d . . . H12 H -0.0516 0.0880 0.0329 0.024 Uiso 1 1 calc R . . C13 C 0.28995(16) 0.04528(8) 0.17158(13) 0.0160(3) Uani 1 1 d . . . C14 C 0.1643(2) 0.09194(10) -0.04244(15) 0.0262(4) Uani 1 1 d . . . H14A H 0.0653 0.1068 -0.0962 0.039 Uiso 1 1 calc R . . H14B H 0.1967 0.0532 -0.0828 0.039 Uiso 1 1 calc R . . H14C H 0.2321 0.1318 -0.0292 0.039 Uiso 1 1 calc R . . C15 C 0.42422(18) 0.03724(10) 0.13877(15) 0.0257(4) Uani 1 1 d . . . H15A H 0.3993 0.0105 0.0606 0.039 Uiso 1 1 calc R . . H15B H 0.5002 0.0119 0.2061 0.039 Uiso 1 1 calc R . . H15C H 0.4610 0.0840 0.1281 0.039 Uiso 1 1 calc R . . C16 C -0.2822(2) 0.15093(10) -0.25605(18) 0.0317(4) Uani 1 1 d . . . H16 H -0.3280 0.1111 -0.3048 0.038 Uiso 1 1 calc R . . C17 C -0.2646(3) 0.27725(11) -0.2341(2) 0.0513(6) Uani 1 1 d . . . H17A H -0.1903 0.2641 -0.1532 0.077 Uiso 1 1 calc R . . H17B H -0.3434 0.3038 -0.2202 0.077 Uiso 1 1 calc R . . H17C H -0.2194 0.3066 -0.2805 0.077 Uiso 1 1 calc R . . C18 C -0.4440(2) 0.22264(12) -0.42564(18) 0.0404(5) Uani 1 1 d . . . H18A H -0.4776 0.1761 -0.4619 0.061 Uiso 1 1 calc R . . H18B H -0.4091 0.2496 -0.4822 0.061 Uiso 1 1 calc R . . H18C H -0.5257 0.2478 -0.4139 0.061 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 0.00959(12) 0.00985(12) 0.01416(13) 0.00047(8) 0.00636(10) -0.00004(8) Zn2 0.01042(10) 0.01072(10) 0.01320(10) 0.00029(6) 0.00640(7) 0.00013(6) O1 0.0165(5) 0.0169(5) 0.0268(6) -0.0083(4) 0.0103(4) -0.0010(4) O2 0.0205(6) 0.0173(5) 0.0200(5) -0.0057(4) 0.0108(4) -0.0062(4) O3 0.0174(5) 0.0139(5) 0.0284(6) -0.0059(4) 0.0100(5) 0.0009(4) O4 0.0201(6) 0.0135(5) 0.0296(6) -0.0068(4) 0.0132(5) -0.0039(4) O5 0.0110(5) 0.0213(5) 0.0131(5) 0.0025(4) 0.0055(4) 0.0017(4) O6 0.0119(5) 0.0190(5) 0.0136(5) 0.0027(4) 0.0063(4) 0.0003(4) O7 0.0477(9) 0.0408(9) 0.0441(9) 0.0107(7) -0.0058(7) 0.0134(7) N1 0.0203(7) 0.0220(7) 0.0132(6) 0.0022(5) 0.0060(5) -0.0011(5) N2 0.0266(8) 0.0236(7) 0.0309(8) 0.0038(6) 0.0075(6) 0.0021(6) C1 0.0157(7) 0.0141(7) 0.0141(7) -0.0011(5) 0.0055(6) -0.0002(5) C2 0.0188(7) 0.0135(7) 0.0173(7) -0.0013(5) 0.0098(6) -0.0014(5) C3 0.0155(7) 0.0190(8) 0.0309(9) -0.0062(6) 0.0105(7) 0.0005(6) C4 0.0156(7) 0.0204(8) 0.0288(8) -0.0083(6) 0.0089(6) -0.0035(6) C5 0.0186(7) 0.0143(7) 0.0193(7) -0.0023(6) 0.0096(6) -0.0013(6) C6 0.0174(7) 0.0171(7) 0.0246(8) -0.0026(6) 0.0082(6) 0.0016(6) C7 0.0155(7) 0.0175(7) 0.0206(7) -0.0034(6) 0.0061(6) -0.0015(6) C8 0.0193(7) 0.0127(7) 0.0161(7) -0.0010(5) 0.0084(6) -0.0010(6) C9 0.0136(7) 0.0127(7) 0.0153(7) -0.0008(5) 0.0056(6) -0.0002(5) C10 0.0154(7) 0.0118(7) 0.0159(7) -0.0009(5) 0.0077(6) -0.0007(5) C11 0.0129(7) 0.0217(8) 0.0192(7) 0.0013(6) 0.0058(6) 0.0011(6) C12 0.0166(7) 0.0232(8) 0.0178(7) 0.0031(6) 0.0036(6) 0.0016(6) C13 0.0150(7) 0.0177(7) 0.0158(7) 0.0004(6) 0.0063(6) -0.0008(6) C14 0.0278(9) 0.0363(10) 0.0148(8) 0.0064(7) 0.0081(7) -0.0013(7) C15 0.0202(8) 0.0431(10) 0.0176(8) 0.0034(7) 0.0113(6) 0.0017(7) C16 0.0312(10) 0.0249(9) 0.0367(10) 0.0021(7) 0.0095(8) 0.0046(7) C17 0.0413(13) 0.0264(10) 0.0698(16) 0.0004(10) 0.0005(11) -0.0040(9) C18 0.0442(12) 0.0433(12) 0.0280(10) 0.0082(8) 0.0062(9) 0.0099(9) _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 O6 2.0574(10) . ? Zn1 O6 2.0575(10) 3_556 ? Zn1 O4 2.0927(10) 4_565 ? Zn1 O4 2.0927(10) 2_546 ? Zn1 O2 2.1105(10) 3_556 ? Zn1 O2 2.1105(10) . ? Zn2 O3 1.9692(10) 2_546 ? Zn2 O1 1.9820(10) . ? Zn2 O5 2.0410(10) . ? Zn2 O6 2.0681(10) . ? Zn2 O5 2.0832(10) 3_656 ? O1 C1 1.2712(18) . ? O2 C1 1.2482(18) . ? O3 C8 1.2721(18) . ? O3 Zn2 1.9691(10) 2_556 ? O4 C8 1.2459(18) . ? O4 Zn1 2.0927(10) 2_556 ? O5 C9 1.3316(18) . ? O5 Zn2 2.0832(10) 3_656 ? O6 C10 1.2981(17) . ? O7 C16 1.222(2) . ? N1 C12 1.351(2) . ? N1 C13 1.378(2) . ? N1 C14 1.4765(19) . ? N2 C16 1.328(2) . ? N2 C17 1.445(3) . ? N2 C18 1.455(2) . ? C1 C2 1.508(2) . ? C2 C3 1.392(2) . ? C2 C7 1.395(2) . ? C3 C4 1.388(2) . ? C3 H3 0.9500 . ? C4 C5 1.395(2) . ? C4 H4 0.9500 . ? C5 C6 1.394(2) . ? C5 C8 1.509(2) . ? C6 C7 1.390(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C9 C13 1.385(2) . ? C9 C10 1.439(2) . ? C10 C11 1.401(2) . ? C11 C12 1.367(2) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C15 1.499(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 O6 Zn1 O6 180.0 . 3_556 ? O6 Zn1 O4 90.97(4) . 4_565 ? O6 Zn1 O4 89.03(4) 3_556 4_565 ? O6 Zn1 O4 89.02(4) . 2_546 ? O6 Zn1 O4 90.97(4) 3_556 2_546 ? O4 Zn1 O4 180.0 4_565 2_546 ? O6 Zn1 O2 91.56(4) . 3_556 ? O6 Zn1 O2 88.44(4) 3_556 3_556 ? O4 Zn1 O2 94.10(4) 4_565 3_556 ? O4 Zn1 O2 85.90(4) 2_546 3_556 ? O6 Zn1 O2 88.44(4) . . ? O6 Zn1 O2 91.56(4) 3_556 . ? O4 Zn1 O2 85.90(4) 4_565 . ? O4 Zn1 O2 94.11(4) 2_546 . ? O2 Zn1 O2 180.0 3_556 . ? O3 Zn2 O1 119.44(5) 2_546 . ? O3 Zn2 O5 121.91(4) 2_546 . ? O1 Zn2 O5 118.59(4) . . ? O3 Zn2 O6 99.77(4) 2_546 . ? O1 Zn2 O6 93.41(4) . . ? O5 Zn2 O6 79.18(4) . . ? O3 Zn2 O5 95.70(4) 2_546 3_656 ? O1 Zn2 O5 93.41(4) . 3_656 ? O5 Zn2 O5 78.48(4) . 3_656 ? O6 Zn2 O5 157.24(4) . 3_656 ? C1 O1 Zn2 122.97(9) . . ? C1 O2 Zn1 133.61(9) . . ? C8 O3 Zn2 126.62(10) . 2_556 ? C8 O4 Zn1 139.48(10) . 2_556 ? C9 O5 Zn2 113.57(9) . . ? C9 O5 Zn2 143.48(9) . 3_656 ? Zn2 O5 Zn2 101.51(4) . 3_656 ? C10 O6 Zn1 135.01(9) . . ? C10 O6 Zn2 113.39(9) . . ? Zn1 O6 Zn2 111.57(5) . . ? C12 N1 C13 121.82(13) . . ? C12 N1 C14 117.99(13) . . ? C13 N1 C14 120.12(13) . . ? C16 N2 C17 120.45(16) . . ? C16 N2 C18 121.38(16) . . ? C17 N2 C18 117.83(16) . . ? O2 C1 O1 126.32(13) . . ? O2 C1 C2 118.25(13) . . ? O1 C1 C2 115.43(13) . . ? C3 C2 C7 119.77(14) . . ? C3 C2 C1 120.45(13) . . ? C7 C2 C1 119.78(13) . . ? C4 C3 C2 120.42(14) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.05(15) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 119.39(14) . . ? C6 C5 C8 120.87(13) . . ? C4 C5 C8 119.72(14) . . ? C7 C6 C5 120.68(14) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C2 119.66(14) . . ? C6 C7 H7 120.2 . . ? C2 C7 H7 120.2 . . ? O4 C8 O3 126.88(13) . . ? O4 C8 C5 116.99(13) . . ? O3 C8 C5 116.12(13) . . ? O5 C9 C13 124.37(13) . . ? O5 C9 C10 116.18(12) . . ? C13 C9 C10 119.41(13) . . ? O6 C10 C11 124.54(13) . . ? O6 C10 C9 117.13(13) . . ? C11 C10 C9 118.33(13) . . ? C12 C11 C10 119.90(14) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? N1 C12 C11 121.19(14) . . ? N1 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? N1 C13 C9 119.18(13) . . ? N1 C13 C15 118.04(13) . . ? C9 C13 C15 122.77(14) . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O7 C16 N2 125.03(19) . . ? O7 C16 H16 117.5 . . ? N2 C16 H16 117.5 . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Zn2 O1 C1 -62.26(13) 2_546 . . . ? O5 Zn2 O1 C1 120.50(11) . . . . ? O6 Zn2 O1 C1 40.97(12) . . . . ? O5 Zn2 O1 C1 -160.76(12) 3_656 . . . ? O6 Zn1 O2 C1 10.85(14) . . . . ? O6 Zn1 O2 C1 -169.15(14) 3_556 . . . ? O4 Zn1 O2 C1 -80.24(14) 4_565 . . . ? O4 Zn1 O2 C1 99.76(14) 2_546 . . . ? O2 Zn1 O2 C1 -105.5(13) 3_556 . . . ? O3 Zn2 O5 C9 100.82(10) 2_546 . . . ? O1 Zn2 O5 C9 -82.00(10) . . . . ? O6 Zn2 O5 C9 5.98(9) . . . . ? O5 Zn2 O5 C9 -169.60(12) 3_656 . . . ? O3 Zn2 O5 Zn2 -89.57(5) 2_546 . . 3_656 ? O1 Zn2 O5 Zn2 87.60(5) . . . 3_656 ? O6 Zn2 O5 Zn2 175.58(5) . . . 3_656 ? O5 Zn2 O5 Zn2 0.0 3_656 . . 3_656 ? O6 Zn1 O6 C10 98(13) 3_556 . . . ? O4 Zn1 O6 C10 -46.57(13) 4_565 . . . ? O4 Zn1 O6 C10 133.43(13) 2_546 . . . ? O2 Zn1 O6 C10 47.56(13) 3_556 . . . ? O2 Zn1 O6 C10 -132.44(13) . . . . ? O6 Zn1 O6 Zn2 -84(13) 3_556 . . . ? O4 Zn1 O6 Zn2 130.92(5) 4_565 . . . ? O4 Zn1 O6 Zn2 -49.08(5) 2_546 . . . ? O2 Zn1 O6 Zn2 -134.95(5) 3_556 . . . ? O2 Zn1 O6 Zn2 45.05(5) . . . . ? O3 Zn2 O6 C10 -127.53(10) 2_546 . . . ? O1 Zn2 O6 C10 111.81(10) . . . . ? O5 Zn2 O6 C10 -6.66(9) . . . . ? O5 Zn2 O6 C10 4.59(17) 3_656 . . . ? O3 Zn2 O6 Zn1 54.40(6) 2_546 . . . ? O1 Zn2 O6 Zn1 -66.25(5) . . . . ? O5 Zn2 O6 Zn1 175.27(6) . . . . ? O5 Zn2 O6 Zn1 -173.48(8) 3_656 . . . ? Zn1 O2 C1 O1 -46.6(2) . . . . ? Zn1 O2 C1 C2 134.03(12) . . . . ? Zn2 O1 C1 O2 11.0(2) . . . . ? Zn2 O1 C1 C2 -169.63(9) . . . . ? O2 C1 C2 C3 151.91(15) . . . . ? O1 C1 C2 C3 -27.5(2) . . . . ? O2 C1 C2 C7 -28.4(2) . . . . ? O1 C1 C2 C7 152.13(14) . . . . ? C7 C2 C3 C4 -1.3(2) . . . . ? C1 C2 C3 C4 178.35(14) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 C6 1.5(2) . . . . ? C3 C4 C5 C8 -177.00(14) . . . . ? C4 C5 C6 C7 -1.1(2) . . . . ? C8 C5 C6 C7 177.33(14) . . . . ? C5 C6 C7 C2 -0.4(2) . . . . ? C3 C2 C7 C6 1.7(2) . . . . ? C1 C2 C7 C6 -178.01(14) . . . . ? Zn1 O4 C8 O3 -1.5(3) 2_556 . . . ? Zn1 O4 C8 C5 177.43(11) 2_556 . . . ? Zn2 O3 C8 O4 0.7(2) 2_556 . . . ? Zn2 O3 C8 C5 -178.22(9) 2_556 . . . ? C6 C5 C8 O4 -162.74(14) . . . . ? C4 C5 C8 O4 15.7(2) . . . . ? C6 C5 C8 O3 16.3(2) . . . . ? C4 C5 C8 O3 -165.30(14) . . . . ? Zn2 O5 C9 C13 177.93(12) . . . . ? Zn2 O5 C9 C13 15.2(2) 3_656 . . . ? Zn2 O5 C9 C10 -4.61(16) . . . . ? Zn2 O5 C9 C10 -167.33(11) 3_656 . . . ? Zn1 O6 C10 C11 3.8(2) . . . . ? Zn2 O6 C10 C11 -173.62(12) . . . . ? Zn1 O6 C10 C9 -176.25(10) . . . . ? Zn2 O6 C10 C9 6.29(16) . . . . ? O5 C9 C10 O6 -1.20(19) . . . . ? C13 C9 C10 O6 176.39(13) . . . . ? O5 C9 C10 C11 178.71(13) . . . . ? C13 C9 C10 C11 -3.7(2) . . . . ? O6 C10 C11 C12 -179.81(14) . . . . ? C9 C10 C11 C12 0.3(2) . . . . ? C13 N1 C12 C11 -0.3(2) . . . . ? C14 N1 C12 C11 -177.17(15) . . . . ? C10 C11 C12 N1 1.8(2) . . . . ? C12 N1 C13 C9 -3.1(2) . . . . ? C14 N1 C13 C9 173.62(14) . . . . ? C12 N1 C13 C15 175.50(15) . . . . ? C14 N1 C13 C15 -7.7(2) . . . . ? O5 C9 C13 N1 -177.53(13) . . . . ? C10 C9 C13 N1 5.1(2) . . . . ? O5 C9 C13 C15 3.9(2) . . . . ? C10 C9 C13 C15 -173.50(14) . . . . ? C17 N2 C16 O7 -2.8(3) . . . . ? C18 N2 C16 O7 -176.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.575 _refine_diff_density_min -0.621 _refine_diff_density_rms 0.080 _database_code_depnum_ccdc_archive 'CCDC 952363' ####################################################################### # # 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_cmpd2_dlk22 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H28 N2 O14 Zn3' _chemical_formula_weight 836.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.127(3) _cell_length_b 9.909(3) _cell_length_c 11.353(4) _cell_angle_alpha 107.182(2) _cell_angle_beta 90.439(4) _cell_angle_gamma 113.787(3) _cell_volume 790.9(5) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2291 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 31.5 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.757 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 2.331 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.860 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.68890 _diffrn_radiation_type Synchrotron' _diffrn_source Synchrotron _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device_type ? _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7266 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _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 2.68 _diffrn_reflns_theta_max 26.60 _reflns_number_total 3262 _reflns_number_gt 2729 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Asymmetric unit comprises 1.5 zincs (Zn1 located at a crystallographic inversion centre), 2 crystallographically independent halves of BDC (each straddling crystallographic inversion centres), one deferiprone and one water. The water hydrogens were located and refined subject to O-H, H...H and Zn1...H distance restraints to assist convergence. ; _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^)+(0.0676P)^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 3262 _refine_ls_number_parameters 232 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.1010 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.012 _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 0.5000 0.5000 0.0000 0.01396(14) Uani 1 2 d SD . . Zn2 Zn 0.13790(4) 0.59115(3) 0.12528(2) 0.01018(12) Uani 1 1 d . . . O1 O 0.4913(3) 0.5044(2) 0.18007(18) 0.0213(4) Uani 1 1 d . . . O2 O 0.2531(3) 0.5429(2) 0.25465(17) 0.0199(4) Uani 1 1 d . . . O3 O 0.2363(3) 0.8445(2) 0.25723(18) 0.0205(4) Uani 1 1 d . . . O4 O -0.0326(3) 0.6557(2) 0.24476(16) 0.0158(4) Uani 1 1 d . . . O5 O 0.3532(2) 0.6389(2) 0.02657(16) 0.0130(4) Uani 1 1 d . . . O6 O 0.0353(2) 0.6421(2) -0.02613(16) 0.0112(4) Uani 1 1 d . . . O7 O 0.2431(3) 0.3019(2) -0.07366(18) 0.0201(4) Uani 1 1 d D . . N1 N 0.3229(3) 0.8960(2) -0.1877(2) 0.0146(5) Uani 1 1 d . . . C1 C 0.3948(4) 0.5209(3) 0.2635(2) 0.0145(5) Uani 1 1 d . . . C2 C 0.4490(4) 0.5087(3) 0.3861(2) 0.0170(5) Uani 1 1 d . . . C3 C 0.5866(4) 0.4620(3) 0.3979(3) 0.0197(6) Uani 1 1 d . . . H3 H 0.6449 0.4355 0.3282 0.024 Uiso 1 1 calc R . . C4 C 0.3610(4) 0.5459(3) 0.4880(3) 0.0198(6) Uani 1 1 d . . . H4 H 0.2659 0.5765 0.4794 0.024 Uiso 1 1 calc R . . C5 C 0.0864(4) 0.7958(3) 0.2950(2) 0.0140(5) Uani 1 1 d . . . C6 C 0.0423(4) 0.9022(3) 0.4010(2) 0.0141(5) Uani 1 1 d . . . C7 C 0.1674(4) 1.0554(3) 0.4592(3) 0.0193(6) Uani 1 1 d . . . H7 H 0.2823 1.0939 0.4317 0.023 Uiso 1 1 calc R . . C8 C -0.1252(4) 0.8472(3) 0.4421(3) 0.0206(6) Uani 1 1 d . . . H8 H -0.2115 0.7425 0.4027 0.025 Uiso 1 1 calc R . . C9 C 0.1785(3) 0.7251(3) -0.0725(2) 0.0105(5) Uani 1 1 d . . . C10 C 0.3476(4) 0.7215(3) -0.0427(2) 0.0117(5) Uani 1 1 d . . . C11 C 0.4999(4) 0.8102(3) -0.0877(2) 0.0150(5) Uani 1 1 d . . . H11 H 0.6149 0.8124 -0.0679 0.018 Uiso 1 1 calc R . . C12 C 0.4831(4) 0.8937(3) -0.1602(2) 0.0163(5) Uani 1 1 d . . . H12 H 0.5868 0.9513 -0.1919 0.020 Uiso 1 1 calc R . . C13 C 0.1685(4) 0.8153(3) -0.1429(2) 0.0139(5) Uani 1 1 d . . . C14 C -0.0019(4) 0.8310(3) -0.1720(3) 0.0224(6) Uani 1 1 d . . . H14A H 0.0234 0.9418 -0.1469 0.034 Uiso 1 1 calc R . . H14B H -0.0955 0.7788 -0.1265 0.034 Uiso 1 1 calc R . . H14C H -0.0449 0.7827 -0.2618 0.034 Uiso 1 1 calc R . . C15 C 0.3147(4) 0.9895(3) -0.2662(3) 0.0242(6) Uani 1 1 d . . . H15A H 0.4339 1.0364 -0.2919 0.036 Uiso 1 1 calc R . . H15B H 0.2810 1.0722 -0.2185 0.036 Uiso 1 1 calc R . . H15C H 0.2237 0.9219 -0.3403 0.036 Uiso 1 1 calc R . . H7A H 0.1397(14) 0.294(2) -0.0275(15) 0.029 Uiso 1 1 d D . . H7B H 0.190(2) 0.281(2) -0.1593(10) 0.029 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 0.0172(3) 0.0202(2) 0.0095(2) 0.00596(16) 0.00317(16) 0.01211(19) Zn2 0.0117(2) 0.01408(17) 0.00683(16) 0.00329(11) 0.00194(11) 0.00751(13) O1 0.0294(12) 0.0347(11) 0.0110(9) 0.0112(8) 0.0071(8) 0.0217(10) O2 0.0206(11) 0.0336(11) 0.0122(9) 0.0111(8) 0.0034(7) 0.0156(9) O3 0.0215(12) 0.0194(10) 0.0190(10) 0.0037(8) 0.0107(8) 0.0088(8) O4 0.0171(10) 0.0157(9) 0.0118(9) -0.0010(7) 0.0008(7) 0.0082(8) O5 0.0157(10) 0.0192(9) 0.0109(8) 0.0078(7) 0.0053(7) 0.0119(8) O6 0.0113(10) 0.0128(8) 0.0106(8) 0.0039(6) 0.0037(7) 0.0061(7) O7 0.0197(11) 0.0259(10) 0.0168(9) 0.0046(8) 0.0019(8) 0.0133(9) N1 0.0175(13) 0.0144(10) 0.0141(11) 0.0082(8) 0.0030(9) 0.0064(9) C1 0.0179(15) 0.0167(12) 0.0107(11) 0.0055(9) 0.0003(10) 0.0083(11) C2 0.0186(15) 0.0178(12) 0.0124(12) 0.0046(9) 0.0000(10) 0.0059(11) C3 0.0239(16) 0.0236(14) 0.0137(12) 0.0063(10) 0.0027(11) 0.0120(12) C4 0.0222(16) 0.0246(14) 0.0164(13) 0.0082(10) 0.0025(11) 0.0126(12) C5 0.0181(15) 0.0174(12) 0.0092(11) 0.0045(9) 0.0040(10) 0.0102(11) C6 0.0187(15) 0.0145(12) 0.0099(11) 0.0017(9) 0.0040(10) 0.0096(11) C7 0.0147(15) 0.0173(13) 0.0211(14) 0.0027(10) 0.0101(11) 0.0043(11) C8 0.0180(15) 0.0130(12) 0.0221(14) -0.0005(10) 0.0053(11) 0.0025(11) C9 0.0107(13) 0.0110(11) 0.0093(11) 0.0018(8) 0.0016(9) 0.0051(10) C10 0.0159(14) 0.0133(11) 0.0078(11) 0.0022(8) 0.0034(9) 0.0090(10) C11 0.0117(14) 0.0192(13) 0.0155(12) 0.0060(10) 0.0037(10) 0.0077(11) C12 0.0137(14) 0.0168(12) 0.0175(13) 0.0066(10) 0.0056(10) 0.0051(11) C13 0.0144(14) 0.0140(11) 0.0131(12) 0.0039(9) 0.0002(10) 0.0064(10) C14 0.0203(16) 0.0263(14) 0.0295(15) 0.0171(12) 0.0047(12) 0.0130(13) C15 0.0269(17) 0.0258(15) 0.0262(15) 0.0189(12) 0.0041(12) 0.0101(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 2.034(2) . ? Zn1 O1 2.034(2) 2_665 ? Zn1 O5 2.1198(17) . ? Zn1 O5 2.1198(17) 2_665 ? Zn1 O7 2.147(2) . ? Zn1 O7 2.147(2) 2_665 ? Zn2 O2 2.0040(18) . ? Zn2 O5 2.0537(19) . ? Zn2 O4 2.0975(19) . ? Zn2 O6 2.0985(18) 2_565 ? Zn2 O6 2.1760(18) . ? Zn2 O3 2.308(2) . ? Zn2 C5 2.528(3) . ? Zn2 Zn2 3.1590(9) 2_565 ? O1 C1 1.250(3) . ? O2 C1 1.265(3) . ? O3 C5 1.248(3) . ? O4 C5 1.276(3) . ? O5 C10 1.304(3) . ? O6 C9 1.342(3) . ? O6 Zn2 2.0985(18) 2_565 ? O7 H7A 0.982(5) . ? O7 H7B 0.987(5) . ? N1 C12 1.348(3) . ? N1 C13 1.384(3) . ? N1 C15 1.482(3) . ? C1 C2 1.510(3) . ? C2 C3 1.391(4) . ? C2 C4 1.399(4) . ? C3 C4 1.395(4) 2_666 ? C3 H3 0.9500 . ? C4 C3 1.395(4) 2_666 ? C4 H4 0.9500 . ? C5 C6 1.500(3) . ? C6 C8 1.389(4) . ? C6 C7 1.388(4) . ? C7 C8 1.392(4) 2_576 ? C7 H7 0.9500 . ? C8 C7 1.392(4) 2_576 ? C8 H8 0.9500 . ? C9 C13 1.387(3) . ? C9 C10 1.430(3) . ? C10 C11 1.402(4) . ? C11 C12 1.368(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.499(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 O1 180.0 . 2_665 ? O1 Zn1 O5 89.94(7) . . ? O1 Zn1 O5 90.06(7) 2_665 . ? O1 Zn1 O5 90.06(7) . 2_665 ? O1 Zn1 O5 89.94(7) 2_665 2_665 ? O5 Zn1 O5 180.0 . 2_665 ? O1 Zn1 O7 95.76(8) . . ? O1 Zn1 O7 84.24(8) 2_665 . ? O5 Zn1 O7 86.69(8) . . ? O5 Zn1 O7 93.31(8) 2_665 . ? O1 Zn1 O7 84.24(8) . 2_665 ? O1 Zn1 O7 95.76(8) 2_665 2_665 ? O5 Zn1 O7 93.31(8) . 2_665 ? O5 Zn1 O7 86.69(8) 2_665 2_665 ? O7 Zn1 O7 180.0 . 2_665 ? O2 Zn2 O5 96.29(8) . . ? O2 Zn2 O4 92.70(8) . . ? O5 Zn2 O4 152.97(7) . . ? O2 Zn2 O6 95.42(8) . 2_565 ? O5 Zn2 O6 103.41(7) . 2_565 ? O4 Zn2 O6 101.03(7) . 2_565 ? O2 Zn2 O6 174.10(7) . . ? O5 Zn2 O6 77.97(7) . . ? O4 Zn2 O6 93.06(7) . . ? O6 Zn2 O6 84.72(7) 2_565 . ? O2 Zn2 O3 89.28(8) . . ? O5 Zn2 O3 94.94(7) . . ? O4 Zn2 O3 59.66(7) . . ? O6 Zn2 O3 160.39(7) 2_565 . ? O6 Zn2 O3 92.53(7) . . ? O2 Zn2 C5 89.92(8) . . ? O5 Zn2 C5 124.12(8) . . ? O4 Zn2 C5 30.25(8) . . ? O6 Zn2 C5 131.26(8) 2_565 . ? O6 Zn2 C5 94.41(7) . . ? O3 Zn2 C5 29.46(8) . . ? O2 Zn2 Zn2 138.41(6) . 2_565 ? O5 Zn2 Zn2 90.60(6) . 2_565 ? O4 Zn2 Zn2 99.43(6) . 2_565 ? O6 Zn2 Zn2 43.31(5) 2_565 2_565 ? O6 Zn2 Zn2 41.41(5) . 2_565 ? O3 Zn2 Zn2 131.01(5) . 2_565 ? C5 Zn2 Zn2 119.42(6) . 2_565 ? C1 O1 Zn1 139.00(17) . . ? C1 O2 Zn2 133.06(17) . . ? C5 O3 Zn2 85.08(15) . . ? C5 O4 Zn2 93.86(15) . . ? C10 O5 Zn2 112.16(15) . . ? C10 O5 Zn1 125.45(15) . . ? Zn2 O5 Zn1 119.12(8) . . ? C9 O6 Zn2 121.62(14) . 2_565 ? C9 O6 Zn2 107.89(14) . . ? Zn2 O6 Zn2 95.28(7) 2_565 . ? Zn1 O7 H7A 119.1(9) . . ? Zn1 O7 H7B 117.2(8) . . ? H7A O7 H7B 102.6(10) . . ? C12 N1 C13 121.5(2) . . ? C12 N1 C15 118.6(2) . . ? C13 N1 C15 119.9(2) . . ? O1 C1 O2 126.5(2) . . ? O1 C1 C2 117.0(2) . . ? O2 C1 C2 116.4(2) . . ? C3 C2 C4 120.3(2) . . ? C3 C2 C1 120.1(3) . . ? C4 C2 C1 119.6(2) . . ? C2 C3 C4 120.0(3) . 2_666 ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 2_666 . ? C3 C4 C2 119.7(3) 2_666 . ? C3 C4 H4 120.2 2_666 . ? C2 C4 H4 120.2 . . ? O3 C5 O4 121.2(2) . . ? O3 C5 C6 120.2(2) . . ? O4 C5 C6 118.5(2) . . ? O3 C5 Zn2 65.46(13) . . ? O4 C5 Zn2 55.89(13) . . ? C6 C5 Zn2 173.37(19) . . ? C8 C6 C7 119.4(2) . . ? C8 C6 C5 119.9(2) . . ? C7 C6 C5 120.8(2) . . ? C6 C7 C8 120.2(3) . 2_576 ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 2_576 . ? C6 C8 C7 120.4(2) . 2_576 ? C6 C8 H8 119.8 . . ? C7 C8 H8 119.8 2_576 . ? O6 C9 C13 122.8(2) . . ? O6 C9 C10 116.8(2) . . ? C13 C9 C10 120.3(2) . . ? O5 C10 C11 123.5(2) . . ? O5 C10 C9 118.7(2) . . ? C11 C10 C9 117.8(2) . . ? C12 C11 C10 120.1(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? N1 C12 C11 121.5(3) . . ? N1 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? N1 C13 C9 118.8(2) . . ? N1 C13 C14 118.1(2) . . ? C9 C13 C14 123.1(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Zn1 O1 C1 122(13) 2_665 . . . ? O5 Zn1 O1 C1 25.5(3) . . . . ? O5 Zn1 O1 C1 -154.5(3) 2_665 . . . ? O7 Zn1 O1 C1 -61.2(3) . . . . ? O7 Zn1 O1 C1 118.8(3) 2_665 . . . ? O5 Zn2 O2 C1 -11.2(3) . . . . ? O4 Zn2 O2 C1 -165.6(2) . . . . ? O6 Zn2 O2 C1 93.0(2) 2_565 . . . ? O6 Zn2 O2 C1 1.9(9) . . . . ? O3 Zn2 O2 C1 -106.1(2) . . . . ? C5 Zn2 O2 C1 -135.5(2) . . . . ? Zn2 Zn2 O2 C1 86.9(3) 2_565 . . . ? O2 Zn2 O3 C5 -91.12(15) . . . . ? O5 Zn2 O3 C5 172.63(15) . . . . ? O4 Zn2 O3 C5 2.43(14) . . . . ? O6 Zn2 O3 C5 13.1(3) 2_565 . . . ? O6 Zn2 O3 C5 94.49(15) . . . . ? Zn2 Zn2 O3 C5 77.51(16) 2_565 . . . ? O2 Zn2 O4 C5 85.21(15) . . . . ? O5 Zn2 O4 C5 -24.3(2) . . . . ? O6 Zn2 O4 C5 -178.73(14) 2_565 . . . ? O6 Zn2 O4 C5 -93.52(15) . . . . ? O3 Zn2 O4 C5 -2.37(13) . . . . ? Zn2 Zn2 O4 C5 -134.72(14) 2_565 . . . ? O2 Zn2 O5 C10 -159.90(16) . . . . ? O4 Zn2 O5 C10 -51.2(2) . . . . ? O6 Zn2 O5 C10 102.98(17) 2_565 . . . ? O6 Zn2 O5 C10 21.47(16) . . . . ? O3 Zn2 O5 C10 -70.08(17) . . . . ? C5 Zn2 O5 C10 -65.71(18) . . . . ? Zn2 Zn2 O5 C10 61.20(16) 2_565 . . . ? O2 Zn2 O5 Zn1 39.40(11) . . . . ? O4 Zn2 O5 Zn1 148.08(12) . . . . ? O6 Zn2 O5 Zn1 -57.73(11) 2_565 . . . ? O6 Zn2 O5 Zn1 -139.24(10) . . . . ? O3 Zn2 O5 Zn1 129.21(10) . . . . ? C5 Zn2 O5 Zn1 133.59(10) . . . . ? Zn2 Zn2 O5 Zn1 -99.51(9) 2_565 . . . ? O1 Zn1 O5 C10 160.0(2) . . . . ? O1 Zn1 O5 C10 -20.0(2) 2_665 . . . ? O5 Zn1 O5 C10 165(12) 2_665 . . . ? O7 Zn1 O5 C10 -104.3(2) . . . . ? O7 Zn1 O5 C10 75.7(2) 2_665 . . . ? O1 Zn1 O5 Zn2 -42.09(11) . . . . ? O1 Zn1 O5 Zn2 137.91(11) 2_665 . . . ? O5 Zn1 O5 Zn2 -37(12) 2_665 . . . ? O7 Zn1 O5 Zn2 53.68(10) . . . . ? O7 Zn1 O5 Zn2 -126.32(10) 2_665 . . . ? O2 Zn2 O6 C9 -34.0(8) . . . . ? O5 Zn2 O6 C9 -20.73(14) . . . . ? O4 Zn2 O6 C9 133.53(14) . . . . ? O6 Zn2 O6 C9 -125.67(16) 2_565 . . . ? O3 Zn2 O6 C9 73.79(14) . . . . ? C5 Zn2 O6 C9 103.24(15) . . . . ? Zn2 Zn2 O6 C9 -125.67(16) 2_565 . . . ? O2 Zn2 O6 Zn2 91.6(7) . . . 2_565 ? O5 Zn2 O6 Zn2 104.95(8) . . . 2_565 ? O4 Zn2 O6 Zn2 -100.80(7) . . . 2_565 ? O6 Zn2 O6 Zn2 0.0 2_565 . . 2_565 ? O3 Zn2 O6 Zn2 -160.54(7) . . . 2_565 ? C5 Zn2 O6 Zn2 -131.09(8) . . . 2_565 ? Zn1 O1 C1 O2 0.0(5) . . . . ? Zn1 O1 C1 C2 178.04(19) . . . . ? Zn2 O2 C1 O1 -10.0(4) . . . . ? Zn2 O2 C1 C2 171.89(18) . . . . ? O1 C1 C2 C3 -7.7(4) . . . . ? O2 C1 C2 C3 170.6(3) . . . . ? O1 C1 C2 C4 171.8(3) . . . . ? O2 C1 C2 C4 -10.0(4) . . . . ? C4 C2 C3 C4 -0.8(5) . . . 2_666 ? C1 C2 C3 C4 178.6(2) . . . 2_666 ? C3 C2 C4 C3 0.8(5) . . . 2_666 ? C1 C2 C4 C3 -178.6(2) . . . 2_666 ? Zn2 O3 C5 O4 -4.0(2) . . . . ? Zn2 O3 C5 C6 176.2(2) . . . . ? Zn2 O4 C5 O3 4.4(3) . . . . ? Zn2 O4 C5 C6 -175.79(19) . . . . ? O2 Zn2 C5 O3 88.67(15) . . . . ? O5 Zn2 C5 O3 -8.88(18) . . . . ? O4 Zn2 C5 O3 -175.8(2) . . . . ? O6 Zn2 C5 O3 -174.18(13) 2_565 . . . ? O6 Zn2 C5 O3 -87.34(15) . . . . ? Zn2 Zn2 C5 O3 -122.25(14) 2_565 . . . ? O2 Zn2 C5 O4 -95.50(15) . . . . ? O5 Zn2 C5 O4 166.95(13) . . . . ? O6 Zn2 C5 O4 1.66(18) 2_565 . . . ? O6 Zn2 C5 O4 88.50(15) . . . . ? O3 Zn2 C5 O4 175.8(2) . . . . ? Zn2 Zn2 C5 O4 53.58(15) 2_565 . . . ? O2 Zn2 C5 C6 -61.5(16) . . . . ? O5 Zn2 C5 C6 -159.1(16) . . . . ? O4 Zn2 C5 C6 34.0(15) . . . . ? O6 Zn2 C5 C6 35.7(16) 2_565 . . . ? O6 Zn2 C5 C6 122.5(16) . . . . ? O3 Zn2 C5 C6 -150.2(17) . . . . ? Zn2 Zn2 C5 C6 87.6(16) 2_565 . . . ? O3 C5 C6 C8 179.7(2) . . . . ? O4 C5 C6 C8 -0.1(4) . . . . ? Zn2 C5 C6 C8 -31.9(17) . . . . ? O3 C5 C6 C7 -0.6(4) . . . . ? O4 C5 C6 C7 179.7(2) . . . . ? Zn2 C5 C6 C7 147.9(15) . . . . ? C8 C6 C7 C8 0.0(5) . . . 2_576 ? C5 C6 C7 C8 -179.7(3) . . . 2_576 ? C7 C6 C8 C7 0.0(5) . . . 2_576 ? C5 C6 C8 C7 179.7(3) . . . 2_576 ? Zn2 O6 C9 C13 91.4(2) 2_565 . . . ? Zn2 O6 C9 C13 -160.42(19) . . . . ? Zn2 O6 C9 C10 -90.6(2) 2_565 . . . ? Zn2 O6 C9 C10 17.6(2) . . . . ? Zn2 O5 C10 C11 159.26(19) . . . . ? Zn1 O5 C10 C11 -41.5(3) . . . . ? Zn2 O5 C10 C9 -19.3(3) . . . . ? Zn1 O5 C10 C9 139.95(18) . . . . ? O6 C9 C10 O5 0.1(3) . . . . ? C13 C9 C10 O5 178.1(2) . . . . ? O6 C9 C10 C11 -178.6(2) . . . . ? C13 C9 C10 C11 -0.5(3) . . . . ? O5 C10 C11 C12 179.9(2) . . . . ? C9 C10 C11 C12 -1.6(4) . . . . ? C13 N1 C12 C11 0.6(4) . . . . ? C15 N1 C12 C11 179.7(2) . . . . ? C10 C11 C12 N1 1.6(4) . . . . ? C12 N1 C13 C9 -2.7(4) . . . . ? C15 N1 C13 C9 178.2(2) . . . . ? C12 N1 C13 C14 176.7(2) . . . . ? C15 N1 C13 C14 -2.3(3) . . . . ? O6 C9 C13 N1 -179.5(2) . . . . ? C10 C9 C13 N1 2.6(3) . . . . ? O6 C9 C13 C14 1.1(4) . . . . ? C10 C9 C13 C14 -176.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.896 _diffrn_reflns_theta_full 26.60 _diffrn_measured_fraction_theta_full 0.896 _refine_diff_density_max 0.477 _refine_diff_density_min -0.816 _refine_diff_density_rms 0.100 _database_code_depnum_ccdc_archive 'CCDC 952364' ####################################################################### # # 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_cmpd5_db638 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H42 N4 O20 Zn3' _chemical_formula_weight 1046.85 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 Hexagonal _symmetry_space_group_name_H-M P6522 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+5/6' '-y, x-y, z+2/3' '-x, -y, z+1/2' '-x+y, -x, z+1/3' 'y, -x+y, z+1/6' 'x-y, -y, -z' '-x, -x+y, -z+1/3' 'y, x, -z+2/3' '-y, -x, -z+1/6' '-x+y, y, -z+1/2' 'x, x-y, -z+5/6' _cell_length_a 11.2503(1) _cell_length_b 11.2503(1) _cell_length_c 59.7860(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6553.27(15) _cell_formula_units_Z 6 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 14877 _cell_measurement_theta_min 1.3 _cell_measurement_theta_max 26.6 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.007 _exptl_crystal_size_mid 0.004 _exptl_crystal_size_min 0.004 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3216 _exptl_absorpt_coefficient_mu 1.717 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.727 _exptl_absorpt_process_details ; Crystalclear - Rigaku software ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_type Synchrotron _diffrn_source Synchrotron _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 57062 _diffrn_reflns_av_R_equivalents 0.0838 _diffrn_reflns_av_sigmaI/netI 0.0947 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -77 _diffrn_reflns_limit_l_max 77 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 26.57 _reflns_number_total 9997 _reflns_number_gt 7941 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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 asymmetric unit contains 1.5 zincs (Zn2 located on 2-fold rotation axis) plus one deferiprone, one derivatised bdc ligand, one water ligand (attached to Zn1) and 2 fragments of DMF. The water hydrogens were located and refined at a distance of 0.98 Angstroms from O9 and 1.5 Angstroms from each other. In the DMF fragment based on N3, both the nitrogen atoms and C18 are located on a 2-fold rotation axis. This necessarily means that O11 is disordered over 2 positions and hence has 50% site-occupancy. This disorder precluded inclusion of the hydrogen atom on C18. The second guest solvent fragment (based on N2) also has atoms (N2 and C17) located at a 2-fold rotation axis. Both of these atoms are common to each arrangement of the DMF molecule that straddles this symmetry element. ; _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^)+(0.0255P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.055(13) _refine_ls_number_reflns 5022 _refine_ls_number_parameters 310 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0758 _refine_ls_wR_factor_gt 0.0741 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 -0.10095(4) -0.57304(4) 0.204404(5) 0.02071(9) Uani 1 1 d . . . Zn2 Zn -0.28235(2) -0.56471(5) 0.2500 0.01852(11) Uani 1 2 d S . . O1 O -0.1428(2) -0.7423(2) 0.22147(3) 0.0262(5) Uani 1 1 d . . . O2 O -0.2363(3) -0.7204(2) 0.25320(3) 0.0340(6) Uani 1 1 d . . . O3 O -0.4164(2) -1.3884(2) 0.28233(3) 0.0310(5) Uani 1 1 d . . . O4 O -0.3477(3) -0.9196(3) 0.28164(4) 0.0487(8) Uani 1 1 d . . . H4 H -0.3242 -0.8413 0.2766 0.058 Uiso 1 1 calc R . . O5 O -0.2076(3) -1.2079(3) 0.22261(4) 0.0414(7) Uani 1 1 d . . . H5 H -0.2138 -1.2781 0.2287 0.050 Uiso 1 1 calc R . . O6 O -0.3352(3) -1.4125(2) 0.24944(3) 0.0327(6) Uani 1 1 d . . . O7 O -0.2679(2) -0.5575(2) 0.21564(3) 0.0230(5) Uani 1 1 d . . . O8 O -0.2076(2) -0.6134(2) 0.17576(3) 0.0296(5) Uani 1 1 d . . . O9 O 0.0609(2) -0.5802(3) 0.18991(4) 0.0315(5) Uani 1 1 d D . . O10 O 0.1805(6) -0.6969(7) 0.21200(8) 0.0561(18) Uani 0.50 1 d P . . O11 O -0.8825(6) -0.8077(6) 0.32121(8) 0.0569(17) Uani 0.50 1 d P . . N1 N -0.5279(3) -0.6251(3) 0.16368(4) 0.0405(8) Uani 1 1 d . . . N2 N 0.1588(3) -0.6824(5) 0.2500 0.0511(13) Uani 1 2 d S . . N3 N -1.0217(6) -1.0217(6) 0.3333 0.092(2) Uani 1 2 d S . . C1 C -0.2021(3) -0.7862(3) 0.24000(4) 0.0238(7) Uani 1 1 d . . . C2 C -0.2384(3) -0.9272(3) 0.24681(4) 0.0211(6) Uani 1 1 d . . . C3 C -0.3110(4) -0.9879(3) 0.26689(5) 0.0287(8) Uani 1 1 d . . . C4 C -0.3446(4) -1.1204(3) 0.27196(5) 0.0279(8) Uani 1 1 d . . . H4A H -0.3906 -1.1596 0.2856 0.034 Uiso 1 1 calc R . . C5 C -0.3136(3) -1.1982(3) 0.25774(4) 0.0239(7) Uani 1 1 d . . . C6 C -0.2411(4) -1.1383(3) 0.23778(4) 0.0262(7) Uani 1 1 d . . . C7 C -0.2034(3) -1.0043(3) 0.23295(5) 0.0227(7) Uani 1 1 d . . . H7 H -0.1520 -0.9633 0.2198 0.027 Uiso 1 1 calc R . . C8 C -0.3576(3) -1.3433(3) 0.26383(5) 0.0258(7) Uani 1 1 d . . . C9 C -0.3541(3) -0.5754(3) 0.19942(4) 0.0251(7) Uani 1 1 d . . . C10 C -0.3208(3) -0.6079(3) 0.17779(4) 0.0257(7) Uani 1 1 d . . . C11 C -0.4119(4) -0.6327(4) 0.16024(5) 0.0318(8) Uani 1 1 d . . . C12 C -0.5567(4) -0.5921(4) 0.18378(5) 0.0413(9) Uani 1 1 d . . . H12 H -0.6372 -0.5856 0.1855 0.050 Uiso 1 1 calc R . . C13 C -0.4716(3) -0.5676(4) 0.20186(5) 0.0327(7) Uani 1 1 d . . . H13 H -0.4940 -0.5453 0.2160 0.039 Uiso 1 1 calc R . . C14 C -0.3897(4) -0.6762(4) 0.13741(5) 0.0459(10) Uani 1 1 d . . . H14A H -0.4461 -0.7761 0.1360 0.069 Uiso 1 1 calc R . . H14B H -0.2927 -0.6486 0.1356 0.069 Uiso 1 1 calc R . . H14C H -0.4159 -0.6320 0.1258 0.069 Uiso 1 1 calc R . . C15 C -0.6254(4) -0.6523(5) 0.14519(6) 0.0604(14) Uani 1 1 d . . . H15A H -0.7023 -0.6425 0.1506 0.091 Uiso 1 1 calc R . . H15B H -0.6602 -0.7458 0.1396 0.091 Uiso 1 1 calc R . . H15C H -0.5786 -0.5866 0.1331 0.091 Uiso 1 1 calc R . . C16 C 0.1474(5) -0.7518(5) 0.23021(6) 0.0515(11) Uani 1 1 d . . . H16 H 0.1116 -0.8482 0.2310 0.062 Uiso 1 1 calc R . . C17 C 0.2334(4) -0.5332(8) 0.2500 0.099(3) Uani 1 2 d S . . H17A H 0.3115 -0.4997 0.2397 0.149 Uiso 0.25 1 calc PR . . H17B H 0.2668 -0.4997 0.2651 0.149 Uiso 0.25 1 calc PR . . H17C H 0.1722 -0.4997 0.2451 0.149 Uiso 0.25 1 calc PR . . C18 C -0.9021(7) -0.9021(7) 0.3333 0.0590(18) Uani 1 2 d S . . C19 C -1.0437(9) -1.1343(7) 0.34742(13) 0.163(4) Uani 1 1 d . . . H19A H -1.0311 -1.2008 0.3387 0.245 Uiso 1 1 calc R . . H19B H -1.1373 -1.1789 0.3534 0.245 Uiso 1 1 calc R . . H19C H -0.9778 -1.1001 0.3598 0.245 Uiso 1 1 calc R . . H9B H 0.117(4) -0.511(4) 0.1788(6) 0.104(19) Uiso 1 1 d D . . H9A H 0.087(8) -0.649(5) 0.1870(12) 0.26(5) 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 0.0259(2) 0.01739(18) 0.01415(13) 0.00056(12) 0.00362(13) 0.00731(16) Zn2 0.0254(2) 0.0120(2) 0.01370(18) 0.000 0.00436(16) 0.00602(12) O1 0.0345(14) 0.0184(12) 0.0270(10) 0.0065(8) 0.0097(9) 0.0142(11) O2 0.0625(18) 0.0259(12) 0.0240(10) 0.0022(9) 0.0084(10) 0.0298(13) O3 0.0456(16) 0.0211(13) 0.0300(11) 0.0072(9) 0.0112(10) 0.0195(12) O4 0.091(2) 0.0283(15) 0.0379(13) 0.0133(11) 0.0352(14) 0.0384(16) O5 0.075(2) 0.0304(15) 0.0282(11) 0.0039(10) 0.0150(12) 0.0338(16) O6 0.0613(18) 0.0217(12) 0.0203(10) -0.0005(9) 0.0010(10) 0.0247(12) O7 0.0265(12) 0.0283(12) 0.0144(8) -0.0016(8) 0.0008(8) 0.0138(11) O8 0.0309(13) 0.0422(15) 0.0140(9) -0.0040(9) 0.0020(8) 0.0170(12) O9 0.0399(15) 0.0361(14) 0.0215(10) 0.0086(10) 0.0135(10) 0.0211(13) O10 0.066(4) 0.103(5) 0.030(2) 0.018(3) 0.006(3) 0.066(4) O11 0.048(4) 0.055(4) 0.043(3) 0.015(3) 0.001(3) 0.007(3) N1 0.0405(19) 0.052(2) 0.0250(13) -0.0039(13) -0.0072(12) 0.0197(17) N2 0.059(3) 0.059(3) 0.035(2) 0.000 0.0079(19) 0.0294(17) N3 0.084(3) 0.084(3) 0.072(4) 0.023(2) -0.023(2) 0.015(4) C1 0.0277(18) 0.0173(16) 0.0226(13) -0.0001(11) -0.0011(12) 0.0084(14) C2 0.0261(17) 0.0134(15) 0.0214(13) 0.0030(11) 0.0027(11) 0.0079(13) C3 0.042(2) 0.0231(18) 0.0236(13) 0.0008(12) 0.0110(14) 0.0183(17) C4 0.040(2) 0.0243(18) 0.0250(14) 0.0080(12) 0.0118(13) 0.0204(16) C5 0.0332(19) 0.0157(16) 0.0207(13) 0.0001(11) -0.0001(12) 0.0106(15) C6 0.037(2) 0.0258(18) 0.0210(12) -0.0044(12) 0.0002(12) 0.0198(16) C7 0.0259(18) 0.0216(17) 0.0188(12) 0.0009(11) 0.0020(12) 0.0105(15) C8 0.0321(19) 0.0184(17) 0.0273(14) -0.0006(12) -0.0024(13) 0.0130(15) C9 0.0292(18) 0.0236(17) 0.0178(13) 0.0014(11) 0.0038(12) 0.0098(15) C10 0.0314(19) 0.0232(17) 0.0181(12) 0.0013(11) 0.0046(12) 0.0104(15) C11 0.032(2) 0.037(2) 0.0204(13) -0.0020(13) -0.0010(13) 0.0135(17) C12 0.038(2) 0.063(3) 0.0335(17) -0.0007(17) 0.0022(15) 0.033(2) C13 0.0317(19) 0.042(2) 0.0246(13) -0.0013(14) 0.0000(13) 0.0190(18) C14 0.055(3) 0.059(3) 0.0193(14) -0.0085(15) -0.0071(15) 0.026(2) C15 0.044(3) 0.105(4) 0.0320(18) -0.001(2) -0.0100(17) 0.037(3) C16 0.056(3) 0.061(3) 0.0343(18) -0.0005(18) -0.0055(18) 0.028(2) C17 0.140(7) 0.047(5) 0.080(5) 0.000 0.004(5) 0.024(2) C18 0.066(4) 0.066(4) 0.041(3) 0.0020(15) -0.0020(15) 0.030(4) C19 0.171(9) 0.093(6) 0.161(7) 0.071(5) -0.027(6) 0.017(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.998(2) . ? Zn1 O8 2.008(2) . ? Zn1 O3 2.009(2) 11_665 ? Zn1 O9 2.054(2) . ? Zn1 O7 2.083(2) . ? Zn2 O7 2.0590(17) . ? Zn2 O7 2.0590(17) 11 ? Zn2 O2 2.069(2) . ? Zn2 O2 2.069(2) 11 ? Zn2 O6 2.075(2) 11_665 ? Zn2 O6 2.075(2) 1_565 ? O1 C1 1.260(3) . ? O2 C1 1.266(4) . ? O3 C8 1.258(3) . ? O3 Zn1 2.009(2) 11_545 ? O4 C3 1.362(4) . ? O4 H4 0.8400 . ? O5 C6 1.369(3) . ? O5 H5 0.8400 . ? O6 C8 1.267(4) . ? O6 Zn2 2.075(2) 1_545 ? O7 C9 1.313(3) . ? O8 C10 1.312(4) . ? O9 H9B 0.976(5) . ? O9 H9A 0.977(5) . ? O10 C16 1.215(6) . ? O11 C18 1.211(6) . ? N1 C12 1.344(4) . ? N1 C11 1.366(4) . ? N1 C15 1.477(4) . ? N2 C16 1.388(4) 11_655 ? N2 C16 1.388(4) . ? N2 C17 1.453(9) . ? N3 C18 1.346(9) . ? N3 C19 1.436(7) 9 ? N3 C19 1.436(7) . ? C1 C2 1.484(4) . ? C2 C7 1.391(4) . ? C2 C3 1.420(4) . ? C3 C4 1.375(4) . ? C4 C5 1.385(4) . ? C4 H4A 0.9500 . ? C5 C6 1.412(4) . ? C5 C8 1.495(4) . ? C6 C7 1.377(4) . ? C7 H7 0.9500 . ? C9 C13 1.377(4) . ? C9 C10 1.443(4) . ? C10 C11 1.393(4) . ? C11 C14 1.512(4) . ? C12 C13 1.377(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O11 1.211(6) 9 ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? 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 O8 112.98(9) . . ? O1 Zn1 O3 119.22(9) . 11_665 ? O8 Zn1 O3 127.69(10) . 11_665 ? O1 Zn1 O9 88.26(9) . . ? O8 Zn1 O9 94.14(9) . . ? O3 Zn1 O9 90.63(10) 11_665 . ? O1 Zn1 O7 97.03(8) . . ? O8 Zn1 O7 80.34(8) . . ? O3 Zn1 O7 90.08(9) 11_665 . ? O9 Zn1 O7 173.51(8) . . ? O7 Zn2 O7 176.09(12) . 11 ? O7 Zn2 O2 94.42(8) . . ? O7 Zn2 O2 88.44(8) 11 . ? O7 Zn2 O2 88.44(8) . 11 ? O7 Zn2 O2 94.42(8) 11 11 ? O2 Zn2 O2 85.69(14) . 11 ? O7 Zn2 O6 87.15(8) . 11_665 ? O7 Zn2 O6 90.06(8) 11 11_665 ? O2 Zn2 O6 92.95(10) . 11_665 ? O2 Zn2 O6 175.27(8) 11 11_665 ? O7 Zn2 O6 90.06(8) . 1_565 ? O7 Zn2 O6 87.14(8) 11 1_565 ? O2 Zn2 O6 175.27(8) . 1_565 ? O2 Zn2 O6 92.95(10) 11 1_565 ? O6 Zn2 O6 88.75(14) 11_665 1_565 ? C1 O1 Zn1 130.5(2) . . ? C1 O2 Zn2 135.66(19) . . ? C8 O3 Zn1 126.4(2) . 11_545 ? C3 O4 H4 109.5 . . ? C6 O5 H5 109.5 . . ? C8 O6 Zn2 136.3(2) . 1_545 ? C9 O7 Zn2 133.85(19) . . ? C9 O7 Zn1 112.11(17) . . ? Zn2 O7 Zn1 112.04(9) . . ? C10 O8 Zn1 113.27(16) . . ? Zn1 O9 H9B 119(3) . . ? Zn1 O9 H9A 137(4) . . ? H9B O9 H9A 100.4(7) . . ? C12 N1 C11 121.4(3) . . ? C12 N1 C15 118.0(3) . . ? C11 N1 C15 120.6(3) . . ? C16 N2 C16 121.6(5) 11_655 . ? C16 N2 C17 119.2(3) 11_655 . ? C16 N2 C17 119.2(3) . . ? C18 N3 C19 121.8(4) . 9 ? C18 N3 C19 121.8(4) . . ? C19 N3 C19 116.4(9) 9 . ? O1 C1 O2 125.1(3) . . ? O1 C1 C2 118.0(3) . . ? O2 C1 C2 116.9(3) . . ? C7 C2 C3 118.5(3) . . ? C7 C2 C1 119.4(3) . . ? C3 C2 C1 122.0(3) . . ? O4 C3 C4 118.1(3) . . ? O4 C3 C2 122.7(3) . . ? C4 C3 C2 119.2(3) . . ? C3 C4 C5 122.0(3) . . ? C3 C4 H4A 119.0 . . ? C5 C4 H4A 119.0 . . ? C4 C5 C6 119.0(3) . . ? C4 C5 C8 119.4(3) . . ? C6 C5 C8 121.6(3) . . ? O5 C6 C7 117.7(3) . . ? O5 C6 C5 123.0(3) . . ? C7 C6 C5 119.2(3) . . ? C6 C7 C2 122.0(3) . . ? C6 C7 H7 119.0 . . ? C2 C7 H7 119.0 . . ? O3 C8 O6 125.1(3) . . ? O3 C8 C5 118.3(3) . . ? O6 C8 C5 116.5(3) . . ? O7 C9 C13 124.8(3) . . ? O7 C9 C10 115.8(3) . . ? C13 C9 C10 119.3(3) . . ? O8 C10 C11 123.7(3) . . ? O8 C10 C9 118.4(3) . . ? C11 C10 C9 117.9(3) . . ? N1 C11 C10 120.3(3) . . ? N1 C11 C14 118.3(3) . . ? C10 C11 C14 121.4(3) . . ? N1 C12 C13 121.2(3) . . ? N1 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C9 C13 C12 119.8(3) . . ? C9 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O10 C16 N2 124.0(5) . . ? O10 C16 H16 118.0 . . ? N2 C16 H16 118.0 . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O11 C18 O11 116.0(9) . 9 ? O11 C18 N3 122.0(4) . . ? O11 C18 N3 122.0(4) 9 . ? N3 C19 H19A 109.5 . . ? N3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O8 Zn1 O1 C1 -112.6(3) . . . . ? O3 Zn1 O1 C1 63.9(3) 11_665 . . . ? O9 Zn1 O1 C1 153.7(3) . . . . ? O7 Zn1 O1 C1 -30.1(3) . . . . ? O7 Zn2 O2 C1 4.1(3) . . . . ? O7 Zn2 O2 C1 -173.3(3) 11 . . . ? O2 Zn2 O2 C1 92.2(3) 11 . . . ? O6 Zn2 O2 C1 -83.3(3) 11_665 . . . ? O6 Zn2 O2 C1 165.7(11) 1_565 . . . ? O7 Zn2 O7 C9 -102.5(3) 11 . . . ? O2 Zn2 O7 C9 120.3(3) . . . . ? O2 Zn2 O7 C9 34.8(3) 11 . . . ? O6 Zn2 O7 C9 -146.9(3) 11_665 . . . ? O6 Zn2 O7 C9 -58.2(3) 1_565 . . . ? O7 Zn2 O7 Zn1 95.29(11) 11 . . . ? O2 Zn2 O7 Zn1 -41.86(12) . . . . ? O2 Zn2 O7 Zn1 -127.41(11) 11 . . . ? O6 Zn2 O7 Zn1 50.88(11) 11_665 . . . ? O6 Zn2 O7 Zn1 139.63(11) 1_565 . . . ? O1 Zn1 O7 C9 -114.4(2) . . . . ? O8 Zn1 O7 C9 -2.2(2) . . . . ? O3 Zn1 O7 C9 126.1(2) 11_665 . . . ? O9 Zn1 O7 C9 29.8(9) . . . . ? O1 Zn1 O7 Zn2 51.77(11) . . . . ? O8 Zn1 O7 Zn2 163.98(12) . . . . ? O3 Zn1 O7 Zn2 -67.70(11) 11_665 . . . ? O9 Zn1 O7 Zn2 -163.9(8) . . . . ? O1 Zn1 O8 C10 94.9(2) . . . . ? O3 Zn1 O8 C10 -81.3(2) 11_665 . . . ? O9 Zn1 O8 C10 -175.3(2) . . . . ? O7 Zn1 O8 C10 1.3(2) . . . . ? Zn1 O1 C1 O2 -8.0(5) . . . . ? Zn1 O1 C1 C2 170.4(2) . . . . ? Zn2 O2 C1 O1 25.3(5) . . . . ? Zn2 O2 C1 C2 -153.0(2) . . . . ? O1 C1 C2 C7 1.4(4) . . . . ? O2 C1 C2 C7 179.9(3) . . . . ? O1 C1 C2 C3 -177.0(3) . . . . ? O2 C1 C2 C3 1.5(5) . . . . ? C7 C2 C3 O4 179.0(3) . . . . ? C1 C2 C3 O4 -2.6(5) . . . . ? C7 C2 C3 C4 -0.1(5) . . . . ? C1 C2 C3 C4 178.3(3) . . . . ? O4 C3 C4 C5 178.8(3) . . . . ? C2 C3 C4 C5 -2.0(5) . . . . ? C3 C4 C5 C6 2.1(5) . . . . ? C3 C4 C5 C8 -177.7(3) . . . . ? C4 C5 C6 O5 -179.1(3) . . . . ? C8 C5 C6 O5 0.7(5) . . . . ? C4 C5 C6 C7 -0.1(5) . . . . ? C8 C5 C6 C7 179.8(3) . . . . ? O5 C6 C7 C2 177.0(3) . . . . ? C5 C6 C7 C2 -2.1(5) . . . . ? C3 C2 C7 C6 2.2(5) . . . . ? C1 C2 C7 C6 -176.3(3) . . . . ? Zn1 O3 C8 O6 7.1(5) 11_545 . . . ? Zn1 O3 C8 C5 -174.8(2) 11_545 . . . ? Zn2 O6 C8 O3 -36.7(5) 1_545 . . . ? Zn2 O6 C8 C5 145.1(3) 1_545 . . . ? C4 C5 C8 O3 -3.2(5) . . . . ? C6 C5 C8 O3 176.9(3) . . . . ? C4 C5 C8 O6 175.0(3) . . . . ? C6 C5 C8 O6 -4.8(5) . . . . ? Zn2 O7 C9 C13 19.4(5) . . . . ? Zn1 O7 C9 C13 -178.4(3) . . . . ? Zn2 O7 C9 C10 -159.4(2) . . . . ? Zn1 O7 C9 C10 2.7(3) . . . . ? Zn1 O8 C10 C11 -179.7(3) . . . . ? Zn1 O8 C10 C9 -0.2(4) . . . . ? O7 C9 C10 O8 -1.8(4) . . . . ? C13 C9 C10 O8 179.3(3) . . . . ? O7 C9 C10 C11 177.7(3) . . . . ? C13 C9 C10 C11 -1.2(5) . . . . ? C12 N1 C11 C10 0.8(6) . . . . ? C15 N1 C11 C10 -179.5(4) . . . . ? C12 N1 C11 C14 177.5(3) . . . . ? C15 N1 C11 C14 -2.9(6) . . . . ? O8 C10 C11 N1 180.0(3) . . . . ? C9 C10 C11 N1 0.5(5) . . . . ? O8 C10 C11 C14 3.4(5) . . . . ? C9 C10 C11 C14 -176.1(3) . . . . ? C11 N1 C12 C13 -1.4(6) . . . . ? C15 N1 C12 C13 178.9(4) . . . . ? O7 C9 C13 C12 -178.1(3) . . . . ? C10 C9 C13 C12 0.7(5) . . . . ? N1 C12 C13 C9 0.6(6) . . . . ? C16 N2 C16 O10 170.0(6) 11_655 . . . ? C17 N2 C16 O10 -10.0(6) . . . . ? C19 N3 C18 O11 -1.2(6) 9 . . . ? C19 N3 C18 O11 178.8(6) . . . . ? C19 N3 C18 O11 178.8(6) 9 . . 9 ? C19 N3 C18 O11 -1.2(6) . . . 9 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.57 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.308 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 952365' ####################################################################### # # 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_cmpd3_k13mfm1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H33 N5 O11 Zn3' _chemical_formula_weight 903.76 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7350(1) _cell_length_b 18.8760(3) _cell_length_c 11.5940(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.518(1) _cell_angle_gamma 90.00 _cell_volume 2020.18(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 28782 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 1.832 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.535 _exptl_absorpt_correction_T_max 0.573 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4622 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.71 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4622 _reflns_number_gt 3663 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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 asymmetric unit comprised 1.5 zinc centres (Zn1 located at a crystallographic inversion centre), one amino-BDC and one deferiprone ligand. The amino group on the BDC ligand is disordered over two positions in a 55:45 ratio. Solvent in the lattice was treated using the SQUEEZE algorithm. Prior to this process there was evidence for some very disordered DMF in the voids. These moieties were oriented such that the fractional occupancy amino hydrogen from each disordered functionality, NOT involved in a framework hydrogen bond, is directed (face on) to a fractional solvent. ; _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^)+(0.0638P)^2^+1.0276P] 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 4622 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.1149 _refine_ls_wR_factor_gt 0.1094 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 1.0000 0.0000 1.0000 0.01966(12) Uani 1 2 d S . . Zn2 Zn 0.63894(3) -0.004827(12) 0.95793(2) 0.02066(11) Uani 1 1 d . . . O1 O 0.6650(2) -0.09998(9) 0.90155(18) 0.0372(4) Uani 1 1 d . . . O2 O 0.8996(2) -0.09383(9) 0.91765(18) 0.0382(5) Uani 1 1 d . . . O3 O 0.8473(2) -0.42105(10) 0.63933(19) 0.0421(5) Uani 1 1 d . . . O4 O 0.6215(2) -0.43605(9) 0.64349(17) 0.0363(4) Uani 1 1 d . . . O5 O 0.5864(2) 0.00706(9) 1.11239(15) 0.0295(4) Uani 1 1 d . . . O6 O 0.84163(18) 0.01125(8) 1.08248(15) 0.0251(4) Uani 1 1 d . . . N1 N 0.8071(3) 0.06025(18) 1.4130(2) 0.0588(8) Uani 1 1 d . . . N2 N 0.4813(6) -0.3227(4) 0.6798(7) 0.093(3) Uani 0.55 1 d P . . H2A H 0.4689 -0.3664 0.6522 0.112 Uiso 0.55 1 calc PR . . H2B H 0.4059 -0.2970 0.6800 0.112 Uiso 0.55 1 calc PR . . N2A N 1.0351(8) -0.2128(4) 0.9004(9) 0.102(3) Uani 0.45 1 d P . . H2A1 H 1.0498 -0.1718 0.9385 0.122 Uiso 0.45 1 calc PR . . H2A2 H 1.1093 -0.2395 0.9003 0.122 Uiso 0.45 1 calc PR . . C1 C 0.7820(3) -0.12455(12) 0.8895(2) 0.0292(5) Uani 1 1 d . . . C2 C 0.7715(3) -0.19764(13) 0.8350(2) 0.0318(6) Uani 1 1 d . . . C3 C 0.6364(3) -0.22680(15) 0.7776(3) 0.0432(7) Uani 1 1 d . . . H3 H 0.5520 -0.2007 0.7749 0.052 Uiso 1 1 calc R . . C4 C 0.6217(3) -0.29378(15) 0.7237(3) 0.0414(7) Uani 1 1 d . . . C5 C 0.7470(3) -0.33080(13) 0.7266(2) 0.0311(5) Uani 1 1 d . . . C6 C 0.8799(3) -0.30219(16) 0.7851(3) 0.0493(8) Uani 1 1 d . . . H6 H 0.9645 -0.3283 0.7884 0.059 Uiso 1 1 calc R . . C7 C 0.8947(3) -0.23554(16) 0.8402(3) 0.0494(8) Uani 1 1 d . . . C8 C 0.7364(3) -0.40159(13) 0.6651(2) 0.0297(5) Uani 1 1 d . . . C9 C 0.6976(3) 0.02574(13) 1.2079(2) 0.0275(5) Uani 1 1 d . . . C10 C 0.8357(3) 0.02827(13) 1.1892(2) 0.0284(5) Uani 1 1 d . . . C11 C 0.9550(3) 0.0486(2) 1.2865(3) 0.0525(8) Uani 1 1 d . . . H11 H 1.0482 0.0516 1.2771 0.063 Uiso 1 1 calc R . . C12 C 0.9365(4) 0.0643(3) 1.3963(3) 0.0711(12) Uani 1 1 d . . . H12 H 1.0182 0.0784 1.4623 0.085 Uiso 1 1 calc R . . C13 C 0.6865(3) 0.04015(16) 1.3214(2) 0.0389(6) Uani 1 1 d . . . C14 C 0.5482(3) 0.0323(2) 1.3517(3) 0.0593(10) Uani 1 1 d . . . H14A H 0.5619 -0.0027 1.4168 0.089 Uiso 1 1 calc R . . H14B H 0.4707 0.0165 1.2794 0.089 Uiso 1 1 calc R . . H14C H 0.5218 0.0781 1.3787 0.089 Uiso 1 1 calc R . . C15 C 0.7969(4) 0.0785(3) 1.5339(3) 0.0986(18) Uani 1 1 d . . . H15A H 0.8942 0.0875 1.5904 0.148 Uiso 1 1 calc R . . H15B H 0.7525 0.0391 1.5642 0.148 Uiso 1 1 calc R . . H15C H 0.7373 0.1211 1.5272 0.148 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 0.0182(2) 0.0172(2) 0.0266(2) -0.00021(12) 0.01134(16) 0.00036(12) Zn2 0.01956(17) 0.02223(17) 0.02391(17) 0.00003(9) 0.01216(12) -0.00036(9) O1 0.0352(10) 0.0278(9) 0.0516(11) -0.0160(8) 0.0179(9) -0.0036(7) O2 0.0422(11) 0.0266(9) 0.0552(12) -0.0162(8) 0.0287(9) -0.0116(8) O3 0.0299(10) 0.0388(10) 0.0607(12) -0.0267(9) 0.0187(9) -0.0064(8) O4 0.0398(11) 0.0346(10) 0.0408(10) -0.0163(8) 0.0217(8) -0.0138(8) O5 0.0217(9) 0.0463(11) 0.0235(8) -0.0031(7) 0.0116(7) -0.0024(7) O6 0.0217(9) 0.0333(8) 0.0234(8) -0.0039(6) 0.0118(7) -0.0023(6) N1 0.0418(15) 0.109(2) 0.0272(12) -0.0200(14) 0.0137(11) -0.0021(15) N2 0.039(3) 0.089(5) 0.140(6) -0.072(5) 0.013(3) 0.003(3) N2A 0.052(4) 0.078(5) 0.168(9) -0.083(6) 0.025(5) -0.003(4) C1 0.0384(14) 0.0224(11) 0.0317(13) -0.0052(9) 0.0181(11) -0.0043(10) C2 0.0393(15) 0.0249(12) 0.0369(14) -0.0091(10) 0.0199(11) -0.0072(10) C3 0.0377(16) 0.0358(14) 0.0575(18) -0.0182(13) 0.0169(14) -0.0014(12) C4 0.0381(16) 0.0368(14) 0.0502(16) -0.0196(12) 0.0151(13) -0.0058(12) C5 0.0351(14) 0.0255(12) 0.0367(14) -0.0084(10) 0.0169(11) -0.0058(10) C6 0.0325(16) 0.0399(16) 0.077(2) -0.0272(15) 0.0196(15) -0.0030(12) C7 0.0379(16) 0.0403(16) 0.072(2) -0.0281(15) 0.0204(15) -0.0105(12) C8 0.0309(13) 0.0272(12) 0.0330(13) -0.0091(10) 0.0131(11) -0.0046(10) C9 0.0269(12) 0.0320(12) 0.0258(12) 0.0008(10) 0.0118(10) 0.0026(10) C10 0.0281(13) 0.0329(12) 0.0273(12) -0.0024(10) 0.0131(10) 0.0004(10) C11 0.0294(15) 0.096(3) 0.0336(15) -0.0137(16) 0.0114(12) -0.0103(16) C12 0.0391(18) 0.137(4) 0.0362(17) -0.030(2) 0.0107(14) -0.017(2) C13 0.0329(14) 0.0609(18) 0.0256(13) -0.0025(12) 0.0131(11) 0.0062(13) C14 0.0388(17) 0.117(3) 0.0288(15) -0.0035(18) 0.0204(13) 0.0094(19) C15 0.060(2) 0.202(6) 0.0348(19) -0.047(3) 0.0165(17) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O6 2.0671(16) . ? Zn1 O6 2.0671(16) 3_757 ? Zn1 O4 2.0913(17) 2_656 ? Zn1 O4 2.0913(17) 4_656 ? Zn1 O2 2.1002(17) 3_757 ? Zn1 O2 2.1002(17) . ? Zn2 O1 1.9552(17) . ? Zn2 O3 1.9712(17) 2_656 ? Zn2 O5 2.0248(17) . ? Zn2 O6 2.0642(17) . ? Zn2 O5 2.0843(18) 3_657 ? Zn2 Zn2 3.1590(5) 3_657 ? O1 C1 1.278(3) . ? O2 C1 1.231(3) . ? O3 C8 1.263(3) . ? O3 Zn2 1.9712(17) 2_646 ? O4 C8 1.249(3) . ? O4 Zn1 2.0914(17) 2_646 ? O5 C9 1.327(3) . ? O5 Zn2 2.0843(18) 3_657 ? O6 C10 1.297(3) . ? N1 C12 1.336(4) . ? N1 C13 1.363(4) . ? N1 C15 1.477(4) . ? N2 C4 1.409(6) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N2A C7 1.391(8) . ? N2A H2A1 0.8800 . ? N2A H2A2 0.8800 . ? C1 C2 1.507(3) . ? C2 C7 1.381(4) . ? C2 C3 1.385(4) . ? C3 C4 1.398(4) . ? C3 H3 0.9500 . ? C4 C5 1.396(4) . ? C5 C6 1.367(4) . ? C5 C8 1.503(3) . ? C6 C7 1.397(4) . ? C6 H6 0.9500 . ? C9 C13 1.381(3) . ? C9 C10 1.429(3) . ? C10 C11 1.392(4) . ? C11 C12 1.373(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.503(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 O6 Zn1 O6 180.0 . 3_757 ? O6 Zn1 O4 89.56(7) . 2_656 ? O6 Zn1 O4 90.44(7) 3_757 2_656 ? O6 Zn1 O4 90.44(7) . 4_656 ? O6 Zn1 O4 89.56(7) 3_757 4_656 ? O4 Zn1 O4 180.0 2_656 4_656 ? O6 Zn1 O2 90.62(6) . 3_757 ? O6 Zn1 O2 89.38(6) 3_757 3_757 ? O4 Zn1 O2 86.49(8) 2_656 3_757 ? O4 Zn1 O2 93.51(8) 4_656 3_757 ? O6 Zn1 O2 89.38(6) . . ? O6 Zn1 O2 90.62(6) 3_757 . ? O4 Zn1 O2 93.51(8) 2_656 . ? O4 Zn1 O2 86.49(8) 4_656 . ? O2 Zn1 O2 180.0 3_757 . ? O1 Zn2 O3 120.41(9) . 2_656 ? O1 Zn2 O5 119.56(8) . . ? O3 Zn2 O5 119.94(8) 2_656 . ? O1 Zn2 O6 99.93(7) . . ? O3 Zn2 O6 93.37(7) 2_656 . ? O5 Zn2 O6 79.55(7) . . ? O1 Zn2 O5 94.75(7) . 3_657 ? O3 Zn2 O5 92.67(7) 2_656 3_657 ? O5 Zn2 O5 79.52(8) . 3_657 ? O6 Zn2 O5 158.47(7) . 3_657 ? O1 Zn2 Zn2 111.76(6) . 3_657 ? O3 Zn2 Zn2 110.53(6) 2_656 3_657 ? O5 Zn2 Zn2 40.45(5) . 3_657 ? O6 Zn2 Zn2 119.84(5) . 3_657 ? O5 Zn2 Zn2 39.07(5) 3_657 3_657 ? C1 O1 Zn2 125.76(16) . . ? C1 O2 Zn1 140.98(16) . . ? C8 O3 Zn2 125.94(16) . 2_646 ? C8 O4 Zn1 134.79(16) . 2_646 ? C9 O5 Zn2 113.57(15) . . ? C9 O5 Zn2 144.08(15) . 3_657 ? Zn2 O5 Zn2 100.48(8) . 3_657 ? C10 O6 Zn2 112.42(15) . . ? C10 O6 Zn1 137.09(16) . . ? Zn2 O6 Zn1 110.42(7) . . ? C12 N1 C13 121.4(2) . . ? C12 N1 C15 118.4(3) . . ? C13 N1 C15 120.2(3) . . ? C4 N2 H2A 120.0 . . ? C4 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C7 N2A H2A1 120.0 . . ? C7 N2A H2A2 120.0 . . ? H2A1 N2A H2A2 120.0 . . ? O2 C1 O1 125.9(2) . . ? O2 C1 C2 118.4(2) . . ? O1 C1 C2 115.7(2) . . ? C7 C2 C3 119.6(2) . . ? C7 C2 C1 120.9(2) . . ? C3 C2 C1 119.5(2) . . ? C2 C3 C4 121.4(3) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 118.5(2) . . ? C5 C4 N2 123.7(3) . . ? C3 C4 N2 117.5(3) . . ? C6 C5 C4 119.7(2) . . ? C6 C5 C8 119.9(2) . . ? C4 C5 C8 120.4(2) . . ? C5 C6 C7 121.7(3) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 119.1 . . ? C2 C7 N2A 124.3(4) . . ? C2 C7 C6 119.0(3) . . ? N2A C7 C6 116.6(4) . . ? O4 C8 O3 125.4(2) . . ? O4 C8 C5 118.7(2) . . ? O3 C8 C5 115.8(2) . . ? O5 C9 C13 123.9(2) . . ? O5 C9 C10 116.0(2) . . ? C13 C9 C10 120.0(2) . . ? O6 C10 C11 124.3(2) . . ? O6 C10 C9 117.8(2) . . ? C11 C10 C9 117.9(2) . . ? C12 C11 C10 119.4(3) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? N1 C12 C11 121.9(3) . . ? N1 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? N1 C13 C9 119.2(2) . . ? N1 C13 C14 117.4(2) . . ? C9 C13 C14 123.4(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Zn2 O1 C1 65.3(2) 2_656 . . . ? O5 Zn2 O1 C1 -118.1(2) . . . . ? O6 Zn2 O1 C1 -34.6(2) . . . . ? O5 Zn2 O1 C1 161.2(2) 3_657 . . . ? Zn2 Zn2 O1 C1 -162.45(19) 3_657 . . . ? O6 Zn1 O2 C1 21.0(3) . . . . ? O6 Zn1 O2 C1 -159.0(3) 3_757 . . . ? O4 Zn1 O2 C1 -68.5(3) 2_656 . . . ? O4 Zn1 O2 C1 111.5(3) 4_656 . . . ? O2 Zn1 O2 C1 82(32) 3_757 . . . ? O1 Zn2 O5 C9 102.17(17) . . . . ? O3 Zn2 O5 C9 -81.27(18) 2_656 . . . ? O6 Zn2 O5 C9 6.60(16) . . . . ? O5 Zn2 O5 C9 -168.3(2) 3_657 . . . ? Zn2 Zn2 O5 C9 -168.3(2) 3_657 . . . ? O1 Zn2 O5 Zn2 -89.53(9) . . . 3_657 ? O3 Zn2 O5 Zn2 87.03(9) 2_656 . . 3_657 ? O6 Zn2 O5 Zn2 174.91(8) . . . 3_657 ? O5 Zn2 O5 Zn2 0.0 3_657 . . 3_657 ? O1 Zn2 O6 C10 -125.62(16) . . . . ? O3 Zn2 O6 C10 112.70(17) 2_656 . . . ? O5 Zn2 O6 C10 -7.13(16) . . . . ? O5 Zn2 O6 C10 6.6(3) 3_657 . . . ? Zn2 Zn2 O6 C10 -3.33(17) 3_657 . . . ? O1 Zn2 O6 Zn1 56.90(9) . . . . ? O3 Zn2 O6 Zn1 -64.77(9) 2_656 . . . ? O5 Zn2 O6 Zn1 175.39(9) . . . . ? O5 Zn2 O6 Zn1 -170.84(14) 3_657 . . . ? Zn2 Zn2 O6 Zn1 179.20(4) 3_657 . . . ? O6 Zn1 O6 C10 68(100) 3_757 . . . ? O4 Zn1 O6 C10 -129.8(2) 2_656 . . . ? O4 Zn1 O6 C10 50.2(2) 4_656 . . . ? O2 Zn1 O6 C10 -43.4(2) 3_757 . . . ? O2 Zn1 O6 C10 136.6(2) . . . . ? O6 Zn1 O6 Zn2 -116(4) 3_757 . . . ? O4 Zn1 O6 Zn2 46.73(8) 2_656 . . . ? O4 Zn1 O6 Zn2 -133.27(8) 4_656 . . . ? O2 Zn1 O6 Zn2 133.22(9) 3_757 . . . ? O2 Zn1 O6 Zn2 -46.78(9) . . . . ? Zn1 O2 C1 O1 4.0(5) . . . . ? Zn1 O2 C1 C2 -176.28(19) . . . . ? Zn2 O1 C1 O2 4.3(4) . . . . ? Zn2 O1 C1 C2 -175.38(16) . . . . ? O2 C1 C2 C7 13.7(4) . . . . ? O1 C1 C2 C7 -166.6(3) . . . . ? O2 C1 C2 C3 -165.5(3) . . . . ? O1 C1 C2 C3 14.2(4) . . . . ? C7 C2 C3 C4 -0.5(5) . . . . ? C1 C2 C3 C4 178.6(3) . . . . ? C2 C3 C4 C5 -1.2(5) . . . . ? C2 C3 C4 N2 172.8(5) . . . . ? C3 C4 C5 C6 2.2(4) . . . . ? N2 C4 C5 C6 -171.4(5) . . . . ? C3 C4 C5 C8 -177.4(3) . . . . ? N2 C4 C5 C8 9.0(6) . . . . ? C4 C5 C6 C7 -1.6(5) . . . . ? C8 C5 C6 C7 178.0(3) . . . . ? C3 C2 C7 N2A -176.8(6) . . . . ? C1 C2 C7 N2A 4.1(7) . . . . ? C3 C2 C7 C6 1.2(5) . . . . ? C1 C2 C7 C6 -178.0(3) . . . . ? C5 C6 C7 C2 -0.1(5) . . . . ? C5 C6 C7 N2A 178.0(6) . . . . ? Zn1 O4 C8 O3 -38.1(4) 2_646 . . . ? Zn1 O4 C8 C5 141.70(19) 2_646 . . . ? Zn2 O3 C8 O4 7.6(4) 2_646 . . . ? Zn2 O3 C8 C5 -172.29(17) 2_646 . . . ? C6 C5 C8 O4 159.6(3) . . . . ? C4 C5 C8 O4 -20.9(4) . . . . ? C6 C5 C8 O3 -20.6(4) . . . . ? C4 C5 C8 O3 159.0(3) . . . . ? Zn2 O5 C9 C13 176.8(2) . . . . ? Zn2 O5 C9 C13 16.7(4) 3_657 . . . ? Zn2 O5 C9 C10 -5.2(3) . . . . ? Zn2 O5 C9 C10 -165.35(19) 3_657 . . . ? Zn2 O6 C10 C11 -173.6(3) . . . . ? Zn1 O6 C10 C11 3.0(4) . . . . ? Zn2 O6 C10 C9 6.6(3) . . . . ? Zn1 O6 C10 C9 -176.85(16) . . . . ? O5 C9 C10 O6 -1.1(3) . . . . ? C13 C9 C10 O6 177.0(2) . . . . ? O5 C9 C10 C11 179.1(3) . . . . ? C13 C9 C10 C11 -2.8(4) . . . . ? O6 C10 C11 C12 -178.8(3) . . . . ? C9 C10 C11 C12 1.0(5) . . . . ? C13 N1 C12 C11 0.1(7) . . . . ? C15 N1 C12 C11 -179.6(4) . . . . ? C10 C11 C12 N1 0.4(7) . . . . ? C12 N1 C13 C9 -2.0(5) . . . . ? C15 N1 C13 C9 177.7(4) . . . . ? C12 N1 C13 C14 175.8(4) . . . . ? C15 N1 C13 C14 -4.5(5) . . . . ? O5 C9 C13 N1 -178.7(3) . . . . ? C10 C9 C13 N1 3.3(4) . . . . ? O5 C9 C13 C14 3.6(5) . . . . ? C10 C9 C13 C14 -174.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.029 _refine_diff_density_min -0.613 _refine_diff_density_rms 0.086 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.050 0.250 0.355 276 35 ' ' 2 -0.095 0.750 0.500 276 35 ' ' _platon_squeeze_details ; ; #===end _database_code_depnum_ccdc_archive 'CCDC 958616'