# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Shi-Yao Yang' _publ_contact_author_email SYYANG@XMU.EDU.CN _publ_section_title ; Control of the topologies and packing modes of three 2D coordination polymers through variation of the solvent ratio of a binary solvent mixture ; loop_ _publ_author_name 'Shi-Yao Yang.' 'Stuart Batten' 'Rong-Bin Huang.' 'Fang-Kuo Wang.' ; Lan-Sun Zheng ; data_669582 _database_code_depnum_ccdc_archive 'CCDC 669582' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H13 N O5 Zn' _chemical_formula_sum 'C12 H13 N O5 Zn' _chemical_formula_weight 316.60 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc 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 18.2323(8) _cell_length_b 10.8209(5) _cell_length_c 13.0970(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.552(1) _cell_angle_gamma 90.00 _cell_volume 2578.9(2) _cell_formula_units_Z 8 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 6608 _cell_measurement_theta_min 2.2384 _cell_measurement_theta_max 28.3822 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.631 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 1.920 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5876 _exptl_absorpt_correction_T_max 0.7238 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% none _diffrn_reflns_number 14421 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 28.53 _reflns_number_total 3082 _reflns_number_gt 2671 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (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. ; _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^)+(0.0494P)^2^+0.7651P] 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 3082 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0837 _refine_ls_wR_factor_gt 0.0814 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 0.044785(10) 0.754788(14) 0.158577(14) 0.02294(9) Uani 1 1 d . . . O1 O 0.01854(8) 0.57271(11) 0.17072(10) 0.0372(3) Uani 1 1 d . . . O2 O 0.04356(7) -0.06475(11) 0.19377(11) 0.0396(3) Uani 1 1 d . . . O3 O 0.12322(8) 0.72771(12) 0.27551(11) 0.0387(3) Uani 1 1 d . . . O4 O 0.05872(7) 0.77859(13) 0.40867(11) 0.0388(3) Uani 1 1 d . . . O5 O 0.10874(9) 0.76354(11) 0.04233(12) 0.0390(3) Uani 1 1 d . . . C1 C 0.0000 0.5197(2) 0.2500 0.0291(5) Uani 1 2 d S . . C2 C 0.0000 0.3816(2) 0.2500 0.0292(5) Uani 1 2 d S . . C3 C 0.01732(10) 0.31669(15) 0.16311(13) 0.0318(4) Uani 1 1 d . . . H3A H 0.0291 0.3593 0.1047 0.038 Uiso 1 1 calc R . . C4 C 0.01709(10) 0.18911(15) 0.16338(14) 0.0315(4) Uani 1 1 d . . . H4A H 0.0285 0.1461 0.1050 0.038 Uiso 1 1 calc R . . C5 C 0.0000 0.1251(2) 0.2500 0.0292(5) Uani 1 2 d S . . C6 C 0.0000 -0.0130(2) 0.2500 0.0310(5) Uani 1 2 d S . . C7 C 0.11704(11) 0.75363(13) 0.36792(15) 0.0308(4) Uani 1 1 d . . . C8 C 0.18624(10) 0.75362(13) 0.43598(15) 0.0296(4) Uani 1 1 d . . . C9 C 0.24863(9) 0.69402(18) 0.40554(13) 0.0349(4) Uani 1 1 d . . . H9A H 0.2479 0.6562 0.3417 0.042 Uiso 1 1 calc R . . C10 C 0.31156(9) 0.69031(18) 0.46894(13) 0.0366(4) Uani 1 1 d . . . H10A H 0.3530 0.6498 0.4478 0.044 Uiso 1 1 calc R . . C11 C 0.13677(10) 0.6902(2) -0.01651(14) 0.0394(4) Uani 1 1 d . . . C12 C 0.13053(13) 0.5537(2) -0.00058(19) 0.0567(6) Uani 1 1 d . . . H12A H 0.1136 0.5380 0.0661 0.085 Uiso 1 1 calc R . . H12B H 0.1778 0.5160 -0.0060 0.085 Uiso 1 1 calc R . . H12C H 0.0963 0.5197 -0.0516 0.085 Uiso 1 1 calc R . . C13 C 0.20600(16) 0.6522(3) -0.1678(2) 0.0836(9) Uani 1 1 d . . . H13A H 0.2081 0.5688 -0.1428 0.125 Uiso 1 1 calc R . . H13B H 0.2548 0.6807 -0.1783 0.125 Uiso 1 1 calc R . . H13C H 0.1770 0.6548 -0.2315 0.125 Uiso 1 1 calc R . . C14 C 0.17730(14) 0.8637(2) -0.1112(2) 0.0680(7) Uani 1 1 d . . . H14A H 0.1634 0.9073 -0.0515 0.102 Uiso 1 1 calc R . . H14B H 0.1447 0.8858 -0.1686 0.102 Uiso 1 1 calc R . . H14C H 0.2268 0.8852 -0.1251 0.102 Uiso 1 1 calc R . . N1 N 0.17275(12) 0.73152(18) -0.09337(16) 0.0511(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.02382(13) 0.02062(13) 0.02410(14) -0.00039(6) -0.00087(9) 0.00020(6) O1 0.0540(8) 0.0210(6) 0.0372(7) 0.0008(5) 0.0071(6) -0.0051(5) O2 0.0416(7) 0.0221(6) 0.0553(8) -0.0059(6) 0.0035(6) 0.0017(5) O3 0.0336(7) 0.0498(7) 0.0314(7) -0.0001(5) -0.0100(6) 0.0044(5) O4 0.0251(6) 0.0498(7) 0.0402(8) -0.0050(6) -0.0079(5) 0.0009(5) O5 0.0428(8) 0.0398(7) 0.0353(8) -0.0021(5) 0.0102(6) -0.0017(5) C1 0.0308(12) 0.0212(10) 0.0350(13) 0.000 -0.0009(10) 0.000 C2 0.0314(12) 0.0195(10) 0.0367(13) 0.000 0.0008(10) 0.000 C3 0.0389(9) 0.0232(8) 0.0339(9) 0.0016(6) 0.0064(7) -0.0016(7) C4 0.0343(9) 0.0236(8) 0.0371(9) -0.0037(6) 0.0053(7) 0.0004(7) C5 0.0268(11) 0.0197(10) 0.0408(13) 0.000 -0.0005(10) 0.000 C6 0.0310(12) 0.0202(10) 0.0408(13) 0.000 -0.0062(10) 0.000 C7 0.0269(9) 0.0299(9) 0.0344(10) 0.0025(6) -0.0071(7) -0.0016(6) C8 0.0250(8) 0.0354(10) 0.0277(9) 0.0058(6) -0.0044(7) -0.0041(6) C9 0.0299(9) 0.0459(10) 0.0284(9) -0.0039(7) -0.0029(7) -0.0015(7) C10 0.0256(8) 0.0472(11) 0.0364(10) -0.0021(8) -0.0032(7) 0.0017(7) C11 0.0322(9) 0.0543(12) 0.0319(9) -0.0036(8) 0.0027(7) -0.0023(8) C12 0.0601(14) 0.0465(12) 0.0656(15) -0.0074(10) 0.0222(11) 0.0014(10) C13 0.085(2) 0.111(2) 0.0599(17) -0.0118(16) 0.0406(15) 0.0008(17) C14 0.0638(15) 0.0754(17) 0.0656(16) 0.0205(13) 0.0116(12) -0.0179(13) N1 0.0482(11) 0.0672(12) 0.0394(10) -0.0020(8) 0.0128(9) -0.0048(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 O5 1.9765(15) . ? Zn1 O2 2.0069(12) 1_565 ? Zn1 O1 2.0360(12) . ? Zn1 O4 2.0487(13) 2 ? Zn1 O3 2.0506(13) . ? Zn1 Zn1 2.9810(4) 2 ? O1 C1 1.2510(16) . ? O2 C6 1.2485(17) . ? O2 Zn1 2.0069(12) 1_545 ? O3 C7 1.254(3) . ? O4 C7 1.248(2) . ? O4 Zn1 2.0487(13) 2 ? O5 C11 1.238(2) . ? C1 O1 1.2509(16) 2 ? C1 C2 1.495(3) . ? C2 C3 1.390(2) 2 ? C2 C3 1.390(2) . ? C3 C4 1.381(3) . ? C3 H3A 0.9300 . ? C4 C5 1.381(2) . ? C4 H4A 0.9300 . ? C5 C4 1.381(2) 2 ? C5 C6 1.495(3) . ? C6 O2 1.2485(17) 2 ? C7 C8 1.499(3) . ? C8 C10 1.384(3) 7_566 ? C8 C9 1.387(3) . ? C9 C10 1.375(2) . ? C9 H9A 0.9300 . ? C10 C8 1.384(3) 7_566 ? C10 H10A 0.9300 . ? C11 N1 1.314(3) . ? C11 C12 1.497(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N1 1.459(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N1 1.452(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 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 O2 98.38(5) . 1_565 ? O5 Zn1 O1 105.02(5) . . ? O2 Zn1 O1 156.59(7) 1_565 . ? O5 Zn1 O4 103.56(6) . 2 ? O2 Zn1 O4 87.33(5) 1_565 2 ? O1 Zn1 O4 86.59(5) . 2 ? O5 Zn1 O3 99.48(6) . . ? O2 Zn1 O3 89.12(5) 1_565 . ? O1 Zn1 O3 87.69(5) . . ? O4 Zn1 O3 156.95(7) 2 . ? O5 Zn1 Zn1 175.95(4) . 2 ? O2 Zn1 Zn1 78.52(4) 1_565 2 ? O1 Zn1 Zn1 78.12(4) . 2 ? O4 Zn1 Zn1 79.02(4) 2 2 ? O3 Zn1 Zn1 77.96(4) . 2 ? C1 O1 Zn1 125.82(12) . . ? C6 O2 Zn1 126.03(13) . 1_545 ? C7 O3 Zn1 126.05(13) . . ? C7 O4 Zn1 125.12(13) . 2 ? C11 O5 Zn1 137.28(13) . . ? O1 C1 O1 125.4(2) 2 . ? O1 C1 C2 117.28(11) 2 . ? O1 C1 C2 117.28(11) . . ? C3 C2 C3 119.3(2) 2 . ? C3 C2 C1 120.34(10) 2 . ? C3 C2 C1 120.34(10) . . ? C4 C3 C2 120.14(15) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C3 C4 C5 120.29(15) . . ? C3 C4 H4A 119.9 . . ? C5 C4 H4A 119.9 . . ? C4 C5 C4 119.8(2) 2 . ? C4 C5 C6 120.10(11) 2 . ? C4 C5 C6 120.10(11) . . ? O2 C6 O2 126.7(2) 2 . ? O2 C6 C5 116.63(11) 2 . ? O2 C6 C5 116.63(11) . . ? O4 C7 O3 126.21(18) . . ? O4 C7 C8 116.97(18) . . ? O3 C7 C8 116.82(18) . . ? C10 C8 C9 118.94(17) 7_566 . ? C10 C8 C7 120.77(17) 7_566 . ? C9 C8 C7 120.26(16) . . ? C10 C9 C8 120.56(16) . . ? C10 C9 H9A 119.7 . . ? C8 C9 H9A 119.7 . . ? C9 C10 C8 120.50(17) . 7_566 ? C9 C10 H10A 119.8 . . ? C8 C10 H10A 119.8 7_566 . ? O5 C11 N1 120.3(2) . . ? O5 C11 C12 120.50(18) . . ? N1 C11 C12 119.23(19) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C13 H13A 109.5 . . ? N1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 . . ? C11 N1 C14 119.6(2) . . ? C11 N1 C13 124.1(2) . . ? C14 N1 C13 116.2(2) . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.419 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.085 #========END data_669583 _database_code_depnum_ccdc_archive 'CCDC 669583' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H30 N2 O14 Zn3' _chemical_formula_sum 'C32 H30 N2 O14 Zn3' _chemical_formula_weight 862.69 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 C2/c _symmetry_space_group_name_Hall -C2yc 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 23.2531(11) _cell_length_b 10.6100(5) _cell_length_c 15.9768(7) _cell_angle_alpha 90.00 _cell_angle_beta 111.641(1) _cell_angle_gamma 90.00 _cell_volume 3663.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6066 _cell_measurement_theta_min 2.3453 _cell_measurement_theta_max 28.0602 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1752 _exptl_absorpt_coefficient_mu 2.015 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4995 _exptl_absorpt_correction_T_max 0.6434 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _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 area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% none _diffrn_reflns_number 15360 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.08 _reflns_number_total 4331 _reflns_number_gt 3698 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (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. ; _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^)+(0.0631P)^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 4331 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0940 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.407056(11) 0.84109(2) 0.062456(16) 0.02970(10) Uani 1 1 d . . . Zn2 Zn 0.2500 0.7500 0.0000 0.02542(10) Uani 1 2 d S . . O1 O 0.41464(9) 0.72269(18) 0.15926(13) 0.0508(5) Uani 1 1 d . . . O2 O 0.31656(8) 0.77000(15) 0.12947(11) 0.0414(4) Uani 1 1 d . . . O3 O 0.31063(8) 0.35084(15) 0.45720(13) 0.0450(4) Uani 1 1 d . . . O4 O 0.39615(8) 0.25789(16) 0.45593(12) 0.0439(4) Uani 1 1 d . . . O5 O 0.36436(7) 1.00085(14) 0.05308(12) 0.0399(4) Uani 1 1 d . . . O6 O 0.27511(7) 0.91994(13) -0.03752(10) 0.0355(3) Uani 1 1 d . . . O7 O 0.48893(8) 0.92114(19) 0.10022(14) 0.0553(5) Uani 1 1 d . . . C1 C 0.36263(11) 0.6128(2) 0.23834(15) 0.0382(5) Uani 1 1 d . . . C2 C 0.31071(11) 0.6036(2) 0.26026(16) 0.0442(6) Uani 1 1 d . . . H2A H 0.2770 0.6560 0.2324 0.053 Uiso 1 1 calc R . . C3 C 0.30880(11) 0.5167(2) 0.32354(17) 0.0440(6) Uani 1 1 d . . . H3A H 0.2741 0.5124 0.3392 0.053 Uiso 1 1 calc R . . C4 C 0.35787(10) 0.4362(2) 0.36369(15) 0.0376(5) Uani 1 1 d . . . C5 C 0.41000(13) 0.4458(3) 0.3414(2) 0.0553(7) Uani 1 1 d . . . H5A H 0.4434 0.3923 0.3681 0.066 Uiso 1 1 calc R . . C6 C 0.41233(13) 0.5344(3) 0.27987(19) 0.0548(7) Uani 1 1 d . . . H6A H 0.4477 0.5415 0.2661 0.066 Uiso 1 1 calc R . . C7 C 0.36456(12) 0.7081(2) 0.17060(15) 0.0389(5) Uani 1 1 d . . . C8 C 0.35374(11) 0.3408(2) 0.43071(16) 0.0363(5) Uani 1 1 d . . . C9 C 0.30737(10) 1.00758(19) 0.00708(14) 0.0315(5) Uani 1 1 d . . . C10 C 0.27799(11) 1.1334(2) 0.00376(16) 0.0351(5) Uani 1 1 d . . . C11 C 0.31171(12) 1.2344(2) 0.05227(19) 0.0477(6) Uani 1 1 d . . . H11A H 0.3534 1.2243 0.0872 0.057 Uiso 1 1 calc R . . C12 C 0.21619(12) 1.1501(2) -0.04905(19) 0.0463(6) Uani 1 1 d . . . H12A H 0.1933 1.0830 -0.0825 0.056 Uiso 1 1 calc R . . C13 C 0.54239(11) 0.8964(3) 0.10446(17) 0.0461(6) Uani 1 1 d . . . C14 C 0.55221(15) 0.7969(3) 0.0456(2) 0.0686(9) Uani 1 1 d . . . H14A H 0.5137 0.7553 0.0134 0.103 Uiso 1 1 calc R . . H14B H 0.5816 0.7365 0.0818 0.103 Uiso 1 1 calc R . . H14C H 0.5677 0.8345 0.0034 0.103 Uiso 1 1 calc R . . C15 C 0.65323(13) 0.9407(4) 0.1707(2) 0.0800(12) Uani 1 1 d . . . H15A H 0.6560 0.8754 0.1307 0.120 Uiso 1 1 calc R . . H15B H 0.6764 0.9165 0.2318 0.120 Uiso 1 1 calc R . . H15C H 0.6698 1.0176 0.1572 0.120 Uiso 1 1 calc R . . C16 C 0.57745(19) 1.0581(4) 0.2143(3) 0.0976(14) Uani 1 1 d . . . H16A H 0.5546 1.0238 0.2482 0.146 Uiso 1 1 calc R . . H16B H 0.5541 1.1248 0.1763 0.146 Uiso 1 1 calc R . . H16C H 0.6162 1.0907 0.2549 0.146 Uiso 1 1 calc R . . N1 N 0.58882(11) 0.9597(3) 0.15908(16) 0.0616(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.03187(15) 0.02644(15) 0.03304(15) 0.00013(9) 0.01462(12) 0.00046(9) Zn2 0.02696(18) 0.02255(18) 0.02861(18) -0.00078(12) 0.01243(14) 0.00022(12) O1 0.0494(11) 0.0550(11) 0.0491(10) 0.0209(9) 0.0193(9) -0.0011(9) O2 0.0502(10) 0.0378(9) 0.0289(8) 0.0034(7) 0.0060(7) -0.0005(7) O3 0.0484(10) 0.0385(9) 0.0597(11) 0.0112(8) 0.0335(9) -0.0019(7) O4 0.0507(10) 0.0421(10) 0.0464(10) 0.0150(8) 0.0267(8) 0.0088(7) O5 0.0352(8) 0.0250(8) 0.0565(10) -0.0017(7) 0.0134(8) 0.0018(6) O6 0.0465(9) 0.0211(7) 0.0392(8) 0.0023(6) 0.0161(7) -0.0027(6) O7 0.0344(9) 0.0557(12) 0.0738(13) -0.0051(10) 0.0176(9) -0.0109(8) C1 0.0379(12) 0.0428(13) 0.0330(11) 0.0080(10) 0.0121(10) -0.0034(10) C2 0.0343(12) 0.0490(14) 0.0451(13) 0.0147(12) 0.0097(11) 0.0018(10) C3 0.0327(12) 0.0536(15) 0.0478(14) 0.0110(12) 0.0170(11) -0.0013(10) C4 0.0369(11) 0.0401(12) 0.0379(12) 0.0091(10) 0.0163(10) -0.0004(10) C5 0.0482(15) 0.0632(18) 0.0652(17) 0.0334(15) 0.0336(14) 0.0186(13) C6 0.0509(15) 0.0634(18) 0.0643(17) 0.0291(15) 0.0381(14) 0.0129(13) C7 0.0487(14) 0.0383(12) 0.0275(11) 0.0007(10) 0.0113(10) -0.0061(11) C8 0.0399(12) 0.0350(12) 0.0366(12) 0.0027(9) 0.0171(10) -0.0054(9) C9 0.0406(12) 0.0227(10) 0.0357(11) 0.0028(8) 0.0195(10) 0.0016(8) C10 0.0367(12) 0.0244(10) 0.0457(13) -0.0012(9) 0.0171(10) 0.0007(9) C11 0.0385(13) 0.0321(12) 0.0630(17) -0.0073(11) 0.0077(12) 0.0038(10) C12 0.0409(13) 0.0280(12) 0.0611(17) -0.0101(11) 0.0085(12) -0.0018(9) C13 0.0382(13) 0.0512(15) 0.0470(14) 0.0156(12) 0.0135(11) -0.0056(11) C14 0.0546(18) 0.071(2) 0.081(2) -0.0022(18) 0.0264(17) 0.0036(16) C15 0.0368(15) 0.128(3) 0.0645(19) 0.029(2) 0.0061(14) -0.0236(18) C16 0.091(3) 0.125(4) 0.079(2) -0.035(2) 0.034(2) -0.052(3) N1 0.0450(13) 0.0902(19) 0.0464(12) 0.0085(13) 0.0130(11) -0.0223(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 O4 1.9353(16) 6_565 ? Zn1 O5 1.9420(15) . ? Zn1 O1 1.9494(17) . ? Zn1 O7 1.9654(17) . ? Zn2 O6 2.0517(14) . ? Zn2 O6 2.0517(14) 7_565 ? Zn2 O3 2.0763(16) 4 ? Zn2 O3 2.0763(16) 6_565 ? Zn2 O2 2.0875(16) . ? Zn2 O2 2.0875(16) 7_565 ? O1 C7 1.252(3) . ? O2 C7 1.253(3) . ? O3 C8 1.228(3) . ? O3 Zn2 2.0763(16) 4_545 ? O4 C8 1.271(3) . ? O4 Zn1 1.9353(16) 6_566 ? O5 C9 1.258(3) . ? O6 C9 1.241(3) . ? O7 C13 1.248(3) . ? C1 C2 1.379(3) . ? C1 C6 1.379(3) . ? C1 C7 1.494(3) . ? C2 C3 1.381(3) . ? C2 H2A 0.9300 . ? C3 C4 1.380(3) . ? C3 H3A 0.9300 . ? C4 C5 1.387(3) . ? C4 C8 1.502(3) . ? C5 C6 1.375(4) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C9 C10 1.492(3) . ? C10 C12 1.383(3) . ? C10 C11 1.384(3) . ? C11 C12 1.379(3) 7_575 ? C11 H11A 0.9300 . ? C12 C11 1.379(3) 7_575 ? C12 H12A 0.9300 . ? C13 N1 1.298(3) . ? C13 C14 1.487(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 N1 1.454(4) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 N1 1.453(5) . ? 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 O4 Zn1 O5 120.55(8) 6_565 . ? O4 Zn1 O1 106.99(8) 6_565 . ? O5 Zn1 O1 121.18(8) . . ? O4 Zn1 O7 107.60(8) 6_565 . ? O5 Zn1 O7 93.23(8) . . ? O1 Zn1 O7 103.94(8) . . ? O6 Zn2 O6 180.00(8) . 7_565 ? O6 Zn2 O3 86.81(6) . 4 ? O6 Zn2 O3 93.19(6) 7_565 4 ? O6 Zn2 O3 93.19(6) . 6_565 ? O6 Zn2 O3 86.81(6) 7_565 6_565 ? O3 Zn2 O3 180.00(9) 4 6_565 ? O6 Zn2 O2 90.77(6) . . ? O6 Zn2 O2 89.23(6) 7_565 . ? O3 Zn2 O2 88.09(7) 4 . ? O3 Zn2 O2 91.91(7) 6_565 . ? O6 Zn2 O2 89.23(6) . 7_565 ? O6 Zn2 O2 90.77(6) 7_565 7_565 ? O3 Zn2 O2 91.91(7) 4 7_565 ? O3 Zn2 O2 88.09(7) 6_565 7_565 ? O2 Zn2 O2 180.0 . 7_565 ? C7 O1 Zn1 112.20(16) . . ? C7 O2 Zn2 131.16(15) . . ? C8 O3 Zn2 143.94(16) . 4_545 ? C8 O4 Zn1 119.28(15) . 6_566 ? C9 O5 Zn1 119.53(14) . . ? C9 O6 Zn2 131.87(14) . . ? C13 O7 Zn1 139.35(19) . . ? C2 C1 C6 119.5(2) . . ? C2 C1 C7 119.6(2) . . ? C6 C1 C7 120.9(2) . . ? C1 C2 C3 120.0(2) . . ? C1 C2 H2A 120.0 . . ? C3 C2 H2A 120.0 . . ? C4 C3 C2 120.6(2) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C3 C4 C5 119.1(2) . . ? C3 C4 C8 119.3(2) . . ? C5 C4 C8 121.6(2) . . ? C6 C5 C4 120.2(2) . . ? C6 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? C5 C6 C1 120.6(2) . . ? C5 C6 H6A 119.7 . . ? C1 C6 H6A 119.7 . . ? O1 C7 O2 123.7(2) . . ? O1 C7 C1 117.8(2) . . ? O2 C7 C1 118.4(2) . . ? O3 C8 O4 126.0(2) . . ? O3 C8 C4 117.5(2) . . ? O4 C8 C4 116.5(2) . . ? O6 C9 O5 125.2(2) . . ? O6 C9 C10 118.57(19) . . ? O5 C9 C10 116.19(19) . . ? C12 C10 C11 119.3(2) . . ? C12 C10 C9 119.7(2) . . ? C11 C10 C9 121.0(2) . . ? C12 C11 C10 120.4(2) 7_575 . ? C12 C11 H11A 119.8 7_575 . ? C10 C11 H11A 119.8 . . ? C11 C12 C10 120.3(2) 7_575 . ? C11 C12 H12A 119.8 7_575 . ? C10 C12 H12A 119.8 . . ? O7 C13 N1 119.5(3) . . ? O7 C13 C14 119.8(2) . . ? N1 C13 C14 120.6(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 . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 N1 C16 119.2(3) . . ? C13 N1 C15 125.2(3) . . ? C16 N1 C15 115.6(3) . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.602 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.080 #===========END # Attachment '3.cif' data_y _database_code_depnum_ccdc_archive 'CCDC 669584' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H6 O5 Zn, C4 H9 N O' _chemical_formula_sum 'C12 H15 N O6 Zn' _chemical_formula_weight 334.62 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9787(3) _cell_length_b 10.1257(5) _cell_length_c 10.8955(5) _cell_angle_alpha 70.4360(10) _cell_angle_beta 74.0180(10) _cell_angle_gamma 76.7500(10) _cell_volume 689.41(6) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 5722 _cell_measurement_theta_min 2.4988 _cell_measurement_theta_max 28.2534 _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 1.805 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5627 _exptl_absorpt_correction_T_max 0.7255 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7767 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.40 _reflns_number_total 3152 _reflns_number_gt 2991 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction 'SAINT (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (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. ; _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^)+(0.0429P)^2^+0.5672P] 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 3152 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0814 _refine_ls_wR_factor_gt 0.0805 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.32623(3) 0.42173(2) 0.55518(2) 0.02120(9) Uani 1 1 d . . . O1 O 0.3366(4) 0.4428(3) 0.36062(17) 0.0565(6) Uani 1 1 d . . . O2 O 0.5999(3) 0.5543(3) 0.28761(19) 0.0557(6) Uani 1 1 d . . . O3 O 0.5435(3) 0.2518(2) 0.5526(3) 0.0530(5) Uani 1 1 d . . . O4 O 0.8022(3) 0.36796(19) 0.4880(3) 0.0552(6) Uani 1 1 d . . . O5 O 0.0075(4) 0.2331(3) 0.9086(2) 0.0789(8) Uani 1 1 d . . . O1W O 0.0812(3) 0.3369(2) 0.6502(2) 0.0402(4) Uani 1 1 d . . . C1 C 0.6437(4) 0.5518(3) 0.0286(2) 0.0410(6) Uani 1 1 d . . . H1A H 0.7404 0.5870 0.0478 0.049 Uiso 1 1 calc R . . C2 C 0.4851(4) 0.5003(3) 0.1299(2) 0.0326(5) Uani 1 1 d . . . C3 C 0.3400(4) 0.4486(3) 0.1011(2) 0.0405(6) Uani 1 1 d . . . H3A H 0.2325 0.4144 0.1683 0.049 Uiso 1 1 calc R . . C4 C 0.4723(4) 0.4998(2) 0.2706(2) 0.0315(5) Uani 1 1 d . . . C5 C 0.7942(3) -0.0011(2) 0.5388(2) 0.0305(4) Uani 1 1 d . . . H5A H 0.6557 -0.0017 0.5650 0.037 Uiso 1 1 calc R . . C6 C 0.8694(3) 0.1242(2) 0.5103(2) 0.0268(4) Uani 1 1 d . . . C7 C 1.0766(3) 0.1249(2) 0.4713(2) 0.0311(5) Uani 1 1 d . . . H7A H 1.1281 0.2082 0.4521 0.037 Uiso 1 1 calc R . . C8 C 0.7265(3) 0.2583(2) 0.5176(2) 0.0284(4) Uani 1 1 d . . . C9 C -0.1409(7) 0.1716(4) 0.9751(4) 0.0724(10) Uani 1 1 d . . . C10 C -0.2667(7) 0.1223(5) 0.9095(5) 0.0787(11) Uani 1 1 d . . . H10A H -0.2058 0.1380 0.8163 0.118 Uiso 1 1 calc R . . H10B H -0.4005 0.1748 0.9196 0.118 Uiso 1 1 calc R . . H10C H -0.2731 0.0231 0.9511 0.118 Uiso 1 1 calc R . . C11 C -0.0735(8) 0.2028(6) 1.1650(4) 0.0898(14) Uani 1 1 d . . . H11A H 0.0343 0.2459 1.0983 0.135 Uiso 1 1 calc R . . H11B H -0.0187 0.1253 1.2315 0.135 Uiso 1 1 calc R . . H11C H -0.1604 0.2718 1.2060 0.135 Uiso 1 1 calc R . . C12 C -0.3599(9) 0.0759(7) 1.1882(5) 0.122(2) Uani 1 1 d . . . H12A H -0.4463 0.0718 1.1350 0.183 Uiso 1 1 calc R . . H12B H -0.4350 0.1266 1.2511 0.183 Uiso 1 1 calc R . . H12C H -0.3089 -0.0186 1.2354 0.183 Uiso 1 1 calc R . . N1 N -0.1912(6) 0.1490(4) 1.1015(4) 0.0899(12) Uani 1 1 d . . . H1WA H 0.068(5) 0.306(4) 0.727(4) 0.055(10) Uiso 1 1 d . . . H1WB H 0.008(7) 0.352(5) 0.620(5) 0.085(17) 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 0.02247(13) 0.02250(13) 0.02049(13) -0.00824(9) -0.00649(9) -0.00173(8) O1 0.0855(16) 0.0784(15) 0.0189(8) -0.0105(9) -0.0079(9) -0.0475(13) O2 0.0477(11) 0.1089(19) 0.0306(9) -0.0381(11) -0.0033(8) -0.0300(11) O3 0.0308(9) 0.0314(9) 0.0936(17) -0.0261(10) -0.0068(10) 0.0058(7) O4 0.0377(10) 0.0232(9) 0.1009(18) -0.0205(10) -0.0125(10) 0.0033(7) O5 0.0771(18) 0.112(2) 0.0374(12) -0.0009(13) 0.0000(12) -0.0409(16) O1W 0.0320(9) 0.0584(12) 0.0294(10) -0.0016(8) -0.0097(8) -0.0186(8) C1 0.0459(14) 0.0602(16) 0.0281(12) -0.0173(11) -0.0090(10) -0.0216(12) C2 0.0421(13) 0.0402(12) 0.0207(10) -0.0121(9) -0.0097(9) -0.0081(10) C3 0.0459(14) 0.0588(16) 0.0244(11) -0.0145(10) -0.0060(10) -0.0211(12) C4 0.0390(12) 0.0356(12) 0.0245(10) -0.0142(9) -0.0128(9) 0.0012(9) C5 0.0242(10) 0.0291(11) 0.0382(12) -0.0129(9) -0.0050(8) -0.0013(8) C6 0.0287(10) 0.0233(10) 0.0289(10) -0.0109(8) -0.0085(8) 0.0028(8) C7 0.0328(11) 0.0235(10) 0.0387(12) -0.0119(9) -0.0077(9) -0.0031(8) C8 0.0334(11) 0.0262(10) 0.0278(10) -0.0126(8) -0.0115(8) 0.0046(8) C9 0.075(2) 0.073(2) 0.054(2) -0.0058(17) -0.0111(18) -0.0034(19) C10 0.085(3) 0.080(3) 0.078(3) -0.018(2) -0.029(2) -0.021(2) C11 0.101(3) 0.128(4) 0.046(2) -0.026(2) -0.021(2) -0.022(3) C12 0.096(4) 0.142(5) 0.078(3) 0.014(3) 0.022(3) -0.042(4) N1 0.082(2) 0.100(3) 0.057(2) 0.0024(18) 0.0052(17) -0.016(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1W 1.9585(18) . ? Zn1 O3 2.0182(17) . ? Zn1 O2 2.0198(17) 2_666 ? Zn1 O1 2.0407(17) . ? Zn1 O4 2.0605(17) 2_666 ? Zn1 Zn1 2.9531(5) 2_666 ? O1 C4 1.246(3) . ? O2 C4 1.232(3) . ? O2 Zn1 2.0198(17) 2_666 ? O3 C8 1.238(3) . ? O4 C8 1.245(3) . ? O4 Zn1 2.0605(17) 2_666 ? O5 C9 1.251(5) . ? O1W H1WA 0.78(4) . ? O1W H1WB 0.65(5) . ? C1 C2 1.386(4) . ? C1 C3 1.388(3) 2_665 ? C1 H1A 0.9300 . ? C2 C3 1.388(3) . ? C2 C4 1.509(3) . ? C3 C1 1.388(3) 2_665 ? C3 H3A 0.9300 . ? C5 C7 1.384(3) 2_756 ? C5 C6 1.390(3) . ? C5 H5A 0.9300 . ? C6 C7 1.391(3) . ? C6 C8 1.501(3) . ? C7 C5 1.384(3) 2_756 ? C7 H7A 0.9300 . ? C9 N1 1.278(5) . ? C9 C10 1.521(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 N1 1.489(6) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N1 1.464(6) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 O1W Zn1 O3 103.34(9) . . ? O1W Zn1 O2 98.44(9) . 2_666 ? O3 Zn1 O2 91.13(10) . 2_666 ? O1W Zn1 O1 102.96(9) . . ? O3 Zn1 O1 87.48(11) . . ? O2 Zn1 O1 158.29(9) 2_666 . ? O1W Zn1 O4 98.58(9) . 2_666 ? O3 Zn1 O4 157.95(9) . 2_666 ? O2 Zn1 O4 88.01(10) 2_666 2_666 ? O1 Zn1 O4 85.27(10) . 2_666 ? O1W Zn1 Zn1 170.19(7) . 2_666 ? O3 Zn1 Zn1 82.91(6) . 2_666 ? O2 Zn1 Zn1 73.63(6) 2_666 2_666 ? O1 Zn1 Zn1 84.70(6) . 2_666 ? O4 Zn1 Zn1 75.71(6) 2_666 2_666 ? C4 O1 Zn1 120.08(16) . . ? C4 O2 Zn1 136.44(18) . 2_666 ? C8 O3 Zn1 124.14(16) . . ? C8 O4 Zn1 130.85(17) . 2_666 ? Zn1 O1W H1WA 116(3) . . ? Zn1 O1W H1WB 118(4) . . ? H1WA O1W H1WB 123(5) . . ? C2 C1 C3 120.9(2) . 2_665 ? C2 C1 H1A 119.6 . . ? C3 C1 H1A 119.6 2_665 . ? C1 C2 C3 119.6(2) . . ? C1 C2 C4 119.9(2) . . ? C3 C2 C4 120.5(2) . . ? C1 C3 C2 119.5(2) 2_665 . ? C1 C3 H3A 120.2 2_665 . ? C2 C3 H3A 120.2 . . ? O2 C4 O1 125.0(2) . . ? O2 C4 C2 117.0(2) . . ? O1 C4 C2 118.0(2) . . ? C7 C5 C6 120.6(2) 2_756 . ? C7 C5 H5A 119.7 2_756 . ? C6 C5 H5A 119.7 . . ? C5 C6 C7 119.58(19) . . ? C5 C6 C8 119.8(2) . . ? C7 C6 C8 120.6(2) . . ? C5 C7 C6 119.8(2) 2_756 . ? C5 C7 H7A 120.1 2_756 . ? C6 C7 H7A 120.1 . . ? O3 C8 O4 125.1(2) . . ? O3 C8 C6 117.9(2) . . ? O4 C8 C6 117.0(2) . . ? O5 C9 N1 120.1(5) . . ? O5 C9 C10 121.8(4) . . ? N1 C9 C10 118.1(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 N1 C12 124.2(5) . . ? C9 N1 C11 118.1(4) . . ? C12 N1 C11 117.7(4) . . ? 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 O1W Zn1 O1 C4 177.1(2) . . . . ? O3 Zn1 O1 C4 -79.8(2) . . . . ? O2 Zn1 O1 C4 6.9(4) 2_666 . . . ? O4 Zn1 O1 C4 79.4(2) 2_666 . . . ? Zn1 Zn1 O1 C4 3.3(2) 2_666 . . . ? O1W Zn1 O3 C8 -169.7(2) . . . . ? O2 Zn1 O3 C8 -70.7(2) 2_666 . . . ? O1 Zn1 O3 C8 87.6(2) . . . . ? O4 Zn1 O3 C8 16.7(4) 2_666 . . . ? Zn1 Zn1 O3 C8 2.6(2) 2_666 . . . ? C3 C1 C2 C3 -0.5(5) 2_665 . . . ? C3 C1 C2 C4 179.1(2) 2_665 . . . ? C1 C2 C3 C1 0.5(5) . . . 2_665 ? C4 C2 C3 C1 -179.1(2) . . . 2_665 ? Zn1 O2 C4 O1 2.8(5) 2_666 . . . ? Zn1 O2 C4 C2 -176.0(2) 2_666 . . . ? Zn1 O1 C4 O2 -4.5(4) . . . . ? Zn1 O1 C4 C2 174.24(17) . . . . ? C1 C2 C4 O2 4.3(4) . . . . ? C3 C2 C4 O2 -176.1(3) . . . . ? C1 C2 C4 O1 -174.6(3) . . . . ? C3 C2 C4 O1 5.0(4) . . . . ? C7 C5 C6 C7 -0.1(4) 2_756 . . . ? C7 C5 C6 C8 178.1(2) 2_756 . . . ? C5 C6 C7 C5 0.1(4) . . . 2_756 ? C8 C6 C7 C5 -178.1(2) . . . 2_756 ? Zn1 O3 C8 O4 5.1(4) . . . . ? Zn1 O3 C8 C6 -175.05(16) . . . . ? Zn1 O4 C8 O3 -14.8(4) 2_666 . . . ? Zn1 O4 C8 C6 165.31(18) 2_666 . . . ? C5 C6 C8 O3 1.7(3) . . . . ? C7 C6 C8 O3 179.8(2) . . . . ? C5 C6 C8 O4 -178.4(2) . . . . ? C7 C6 C8 O4 -0.3(3) . . . . ? O5 C9 N1 C12 -178.9(5) . . . . ? C10 C9 N1 C12 1.4(7) . . . . ? O5 C9 N1 C11 2.3(7) . . . . ? C10 C9 N1 C11 -177.4(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O5 0.78(4) 1.83(4) 2.601(3) 174(4) . O1W H1WB O4 0.65(5) 2.24(5) 2.874(3) 166(6) 1_455 _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.898 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.076