# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2014 data_global #============================================================================== # CCDC Numbers # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Dr. Jagadese J. Vittal Department of Chemistry National University of Singapore 3 Science Drive 3 SINGAPORE 117543 ; _publ_contact_author_phone '(65) 6516 2975' _publ_contact_author_fax '(65) 6779 1691' _publ_contact_author_email chmjjv@nus.edu.sg _publ_requested_journal JACS _publ_requested_coeditor_name ' ' _publ_contact_letter ; '' ; #============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _iucr_compatibility_tag ACTA95 _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year 2007 _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Solid-State Conversion of a MOF to a Metal-Organo Polymeric Framework (MOPF) via [2+2] Cycloaddition Reaction ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'In-Hyeok Park' ; Department of Chemistry and Research Institute of Natural Science Gyeongsang National University Jinju 660-701 Republic of Korea ; 'Anjana Chanthapally' ; Department of Chemistry National University of Singapore SINGAPORE 117543 ; 'Hyeong-Hwan Lee' ; Department of Chemistry and Research Institute of Natural Science Gyeongsang National University Jinju 660-701 Republic of Korea : 'Shim Sung Lee' ; Department of Chemistry and Research Institute of Natural Science Gyeongsang National University Jinju 660-701 Republic of Korea : 'Jagadese J. Vittal' ; Department of Chemistry National University of Singapore SINGAPORE 117543 ; #============================================================================== #data Zn(formate)-1 CCDC Number ???? data_formate1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 N O4 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.84140(10) _cell_length_b 21.8416(4) _cell_length_c 9.4560(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.6840(10) _cell_angle_gamma 90.00 _cell_volume 1321.91(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9309 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 28.29 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.681 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 1.873 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6250 _exptl_absorpt_correction_T_max 0.8348 _exptl_absorpt_process_details 'SADABS (Shelcrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21774 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2607 _reflns_number_gt 2424 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0324P)^2^+1.9874P] 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 2607 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0794 _refine_ls_wR_factor_gt 0.0781 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 0.31756(4) 0.257549(12) 0.54732(3) 0.01940(11) Uani 1 1 d . . . O1 O 0.4554(3) 0.33380(8) 0.5314(2) 0.0323(4) Uani 1 1 d . . . O2 O 0.1497(3) 0.37457(9) 0.5132(2) 0.0369(5) Uani 1 1 d . . . N1 N 0.5122(3) 0.19437(9) 0.5117(2) 0.0212(4) Uani 1 1 d . . . C1 C 0.4760(4) 0.16552(11) 0.3792(3) 0.0221(5) Uani 1 1 d . . . H1 H 0.3439 0.1709 0.3012 0.027 Uiso 1 1 calc R . . C2 C 0.6216(4) 0.12858(11) 0.3512(3) 0.0224(5) Uani 1 1 d . . . H2 H 0.5892 0.1094 0.2554 0.027 Uiso 1 1 calc R . . C3 C 0.8168(4) 0.11924(11) 0.4635(3) 0.0208(5) Uani 1 1 d . . . C4 C 0.8513(4) 0.14821(12) 0.6026(3) 0.0242(5) Uani 1 1 d . . . H4 H 0.9797 0.1424 0.6839 0.029 Uiso 1 1 calc R . . C5 C 0.7003(4) 0.18482(12) 0.6211(3) 0.0251(5) Uani 1 1 d . . . H5 H 0.7289 0.2046 0.7157 0.030 Uiso 1 1 calc R . . C6 C 0.9750(4) 0.08191(12) 0.4353(3) 0.0237(5) Uani 1 1 d . . . H6 H 0.9382 0.0625 0.3396 0.028 Uiso 1 1 calc R . . C7 C 1.1677(4) 0.07286(11) 0.5336(3) 0.0248(5) Uani 1 1 d . . . H7 H 1.2024 0.0934 0.6279 0.030 Uiso 1 1 calc R . . C8 C 1.3336(4) 0.03467(11) 0.5132(3) 0.0206(5) Uani 1 1 d . . . C9 C 1.3125(4) 0.00385(11) 0.3790(3) 0.0215(5) Uani 1 1 d . . . H9 H 1.1843 0.0061 0.2958 0.026 Uiso 1 1 calc R . . C10 C 1.5248(4) 0.02971(11) 0.6339(3) 0.0214(5) Uani 1 1 d . . . H10 H 1.5421 0.0500 0.7264 0.026 Uiso 1 1 calc R . . C11 C 0.3317(4) 0.37936(11) 0.5181(3) 0.0253(6) Uani 1 1 d . . . C12 C 0.4211(4) 0.44163(11) 0.5087(3) 0.0201(5) Uani 1 1 d . . . C13 C 0.3126(4) 0.49364(12) 0.5228(3) 0.0218(5) Uani 1 1 d . . . H13A H 0.1840 0.4893 0.5391 0.026 Uiso 1 1 calc R . . C14 C 0.6109(4) 0.44816(11) 0.4865(3) 0.0219(5) Uani 1 1 d . . . H14 H 0.6876 0.4130 0.4777 0.026 Uiso 1 1 calc R . . O3 O -0.2583(3) 0.26612(8) 0.2222(2) 0.0255(4) Uani 1 1 d . . . O4 O 0.0648(3) 0.24254(8) 0.3670(2) 0.0228(4) Uani 1 1 d . . . C15 C -0.1145(4) 0.26304(11) 0.3479(3) 0.0224(5) Uani 1 1 d . . . H15 H -0.1422 0.2770 0.4341 0.027 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 0.02082(17) 0.01483(16) 0.02048(17) 0.00091(10) 0.00473(12) -0.00096(10) O1 0.0387(11) 0.0164(9) 0.0345(11) 0.0041(8) 0.0041(9) -0.0057(8) O2 0.0444(12) 0.0291(10) 0.0460(12) -0.0085(9) 0.0268(10) -0.0175(9) N1 0.0235(11) 0.0154(9) 0.0237(11) 0.0002(8) 0.0071(9) -0.0009(8) C1 0.0215(12) 0.0207(12) 0.0227(12) 0.0021(10) 0.0060(10) -0.0011(10) C2 0.0228(12) 0.0251(12) 0.0180(12) 0.0006(10) 0.0057(10) -0.0010(10) C3 0.0199(12) 0.0209(12) 0.0232(12) 0.0032(10) 0.0096(10) -0.0018(9) C4 0.0184(12) 0.0277(13) 0.0226(13) -0.0007(10) 0.0025(10) -0.0022(10) C5 0.0250(13) 0.0241(12) 0.0240(13) -0.0049(10) 0.0058(11) -0.0032(10) C6 0.0243(13) 0.0245(12) 0.0232(13) -0.0007(10) 0.0096(11) 0.0008(10) C7 0.0281(13) 0.0208(12) 0.0258(13) -0.0010(10) 0.0100(11) 0.0032(10) C8 0.0198(12) 0.0211(12) 0.0209(12) 0.0009(10) 0.0072(10) -0.0002(9) C9 0.0201(12) 0.0224(12) 0.0190(12) -0.0004(10) 0.0032(9) 0.0001(9) C10 0.0235(12) 0.0223(12) 0.0172(12) -0.0029(9) 0.0056(10) -0.0012(10) C11 0.0398(16) 0.0183(12) 0.0153(12) -0.0019(9) 0.0067(11) -0.0084(11) C12 0.0250(13) 0.0185(11) 0.0122(11) 0.0007(9) 0.0009(9) -0.0059(9) C13 0.0213(12) 0.0242(12) 0.0179(12) 0.0004(9) 0.0046(10) -0.0040(10) C14 0.0250(13) 0.0190(12) 0.0183(12) 0.0000(9) 0.0035(10) 0.0013(10) O3 0.0244(9) 0.0289(9) 0.0212(9) -0.0008(7) 0.0055(8) 0.0042(7) O4 0.0234(9) 0.0203(8) 0.0209(9) -0.0008(7) 0.0030(7) 0.0000(7) C15 0.0259(13) 0.0201(12) 0.0213(13) -0.0015(10) 0.0083(11) -0.0024(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.9456(18) . ? Zn1 O3 1.9690(18) 4_666 ? Zn1 O4 1.9804(18) . ? Zn1 N1 2.027(2) . ? O1 C11 1.283(3) . ? O2 C11 1.234(3) . ? N1 C1 1.345(3) . ? N1 C5 1.352(3) . ? C1 C2 1.378(3) . ? C2 C3 1.397(3) . ? C3 C4 1.402(4) . ? C3 C6 1.453(3) . ? C4 C5 1.365(4) . ? C6 C7 1.333(4) . ? C7 C8 1.475(3) . ? C8 C9 1.398(3) . ? C8 C10 1.404(3) . ? C9 C10 1.373(3) 3_856 ? C10 C9 1.373(3) 3_856 ? C11 C12 1.507(3) . ? C12 C13 1.389(4) . ? C12 C14 1.394(3) . ? C13 C14 1.389(3) 3_666 ? C14 C13 1.389(3) 3_666 ? O3 C15 1.249(3) . ? O3 Zn1 1.9690(18) 4_565 ? O4 C15 1.257(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O3 124.65(8) . 4_666 ? O1 Zn1 O4 112.00(8) . . ? O3 Zn1 O4 105.68(8) 4_666 . ? O1 Zn1 N1 101.83(8) . . ? O3 Zn1 N1 110.15(8) 4_666 . ? O4 Zn1 N1 99.76(8) . . ? C11 O1 Zn1 110.52(17) . . ? C1 N1 C5 116.9(2) . . ? C1 N1 Zn1 123.92(17) . . ? C5 N1 Zn1 118.79(17) . . ? N1 C1 C2 123.0(2) . . ? C1 C2 C3 120.1(2) . . ? C2 C3 C4 116.5(2) . . ? C2 C3 C6 121.1(2) . . ? C4 C3 C6 122.4(2) . . ? C5 C4 C3 120.0(2) . . ? N1 C5 C4 123.4(2) . . ? C7 C6 C3 125.0(2) . . ? C6 C7 C8 127.6(2) . . ? C9 C8 C10 117.9(2) . . ? C9 C8 C7 123.6(2) . . ? C10 C8 C7 118.4(2) . . ? C10 C9 C8 120.7(2) 3_856 . ? C9 C10 C8 121.4(2) 3_856 . ? O2 C11 O1 124.0(2) . . ? O2 C11 C12 120.0(2) . . ? O1 C11 C12 116.0(2) . . ? C13 C12 C14 119.2(2) . . ? C13 C12 C11 119.4(2) . . ? C14 C12 C11 121.4(2) . . ? C14 C13 C12 121.1(2) 3_666 . ? C13 C14 C12 119.7(2) 3_666 . ? C15 O3 Zn1 115.65(17) . 4_565 ? C15 O4 Zn1 125.16(16) . . ? O3 C15 O4 123.8(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.242 _refine_diff_density_min -0.551 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 955835' #CCDC 955836 data_form2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 N O4.50 Zn' _chemical_formula_weight 343.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.3685(18) _cell_length_b 22.092(4) _cell_length_c 9.448(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.283(10) _cell_angle_gamma 90.00 _cell_volume 1433.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2387 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 22.43 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 1.732 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3769 _exptl_absorpt_correction_T_max 0.9032 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12614 _diffrn_reflns_av_R_equivalents 0.1037 _diffrn_reflns_av_sigmaI/netI 0.1002 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2810 _reflns_number_gt 1895 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. For P2(1)/c space group, Z = 4 was preferred. The formate ligand was found to be disordered. The occupancies were refined to 0.563(8) and 0.437(8). One half oxygen atoms of the water molecule was located and its positional and isotropic thermal parameters were refined. No hydrogen atoms were included in the model. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0016P)^2^+2.9001P] 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 2810 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0996 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1631 _refine_ls_wR_factor_gt 0.1487 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.59827(11) 0.24389(2) 0.57986(9) 0.0606(3) Uani 1 1 d . . . O1 O 0.4562(8) 0.16381(17) 0.5356(5) 0.0829(15) Uani 1 1 d . . . O2 O 0.7631(9) 0.14426(19) 0.5903(6) 0.0949(18) Uani 1 1 d . . . N1 N 0.3777(7) 0.30531(18) 0.5282(6) 0.0555(13) Uani 1 1 d . . . C1 C 0.2961(9) 0.3209(2) 0.6309(8) 0.0603(17) Uani 1 1 d . . . H1 H 0.3330 0.2992 0.7240 0.072 Uiso 1 1 calc R . . C2 C 0.1612(9) 0.3671(2) 0.6045(7) 0.0547(15) Uani 1 1 d . . . H2 H 0.1071 0.3764 0.6792 0.066 Uiso 1 1 calc R . . C3 C 0.1042(7) 0.4000(2) 0.4708(6) 0.0410(12) Uani 1 1 d . . . C4 C 0.1803(8) 0.3816(2) 0.3615(7) 0.0466(13) Uani 1 1 d . . . H4 H 0.1393 0.4009 0.2651 0.056 Uiso 1 1 calc R . . C5 C 0.3160(9) 0.3351(2) 0.3954(7) 0.0554(15) Uani 1 1 d . . . H5 H 0.3679 0.3238 0.3207 0.066 Uiso 1 1 calc R . . C6 C -0.0208(7) 0.4560(2) 0.4390(6) 0.0345(11) Uani 1 1 d . . . H6 H -0.1353 0.4509 0.3423 0.041 Uiso 1 1 calc R . . C7 C -0.0885(6) 0.48220(19) 0.5650(6) 0.0333(11) Uani 1 1 d . . . H7 H -0.0247 0.4605 0.6636 0.040 Uiso 1 1 calc R . . C8 C -0.3026(6) 0.4882(2) 0.5277(6) 0.0354(11) Uani 1 1 d . . . C9 C -0.4274(6) 0.5089(2) 0.3858(6) 0.0377(12) Uani 1 1 d . . . H9 H -0.3785 0.5150 0.3067 0.045 Uiso 1 1 calc R . . C10 C -0.3782(7) 0.4794(2) 0.6406(6) 0.0373(11) Uani 1 1 d . . . H10 H -0.2958 0.4651 0.7375 0.045 Uiso 1 1 calc R . . C11 C 0.5916(12) 0.1282(3) 0.5504(7) 0.0656(19) Uani 1 1 d . . . C12 C 0.5416(9) 0.0611(2) 0.5232(6) 0.0460(13) Uani 1 1 d . . . C13 C 0.3552(9) 0.0406(2) 0.4931(6) 0.0499(14) Uani 1 1 d . . . H13 H 0.2548 0.0684 0.4886 0.060 Uiso 1 1 calc R . . C14 C 0.6864(9) 0.0208(2) 0.5307(6) 0.0513(14) Uani 1 1 d . . . H14 H 0.8155 0.0349 0.5523 0.062 Uiso 1 1 calc R . . O3 O 0.8463(10) 0.2271(3) 0.2391(8) 0.052(2) Uani 0.563(8) 1 d P . 1 O4 O 0.669(5) 0.2516(10) 0.367(3) 0.054(5) Uani 0.563(8) 1 d P . 1 C15 C 0.8267(15) 0.2343(4) 0.3647(13) 0.046(3) Uani 0.563(8) 1 d P . 1 H15 H 0.9324 0.2266 0.4569 0.056 Uiso 0.563(8) 1 calc PR . 1 O3A O 0.7959(13) 0.2825(4) 0.5568(12) 0.059(3) Uani 0.437(8) 1 d P . 2 O4A O 0.636(5) 0.2609(15) 0.327(5) 0.070(11) Uani 0.437(8) 1 d P . 2 C15A C 0.778(2) 0.2773(7) 0.4165(19) 0.045(4) Uani 0.437(8) 1 d P . 2 H15A H 0.8844 0.2873 0.3869 0.054 Uiso 0.437(8) 1 calc PR . 2 O1W O 0.973(2) 0.1360(7) 0.4052(18) 0.145(5) Uiso 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0733(5) 0.0231(3) 0.0721(6) -0.0062(3) 0.0105(4) 0.0077(3) O1 0.155(5) 0.031(2) 0.065(3) 0.000(2) 0.044(3) 0.009(3) O2 0.118(4) 0.045(2) 0.097(4) 0.000(2) 0.008(3) -0.033(3) N1 0.079(3) 0.028(2) 0.060(4) -0.011(2) 0.025(3) 0.013(2) C1 0.092(5) 0.030(3) 0.059(4) -0.001(3) 0.027(4) 0.012(3) C2 0.084(4) 0.037(3) 0.056(4) -0.001(3) 0.041(3) 0.013(3) C3 0.045(3) 0.032(2) 0.049(4) -0.008(2) 0.020(3) 0.000(2) C4 0.062(3) 0.039(3) 0.043(4) -0.004(2) 0.024(3) 0.013(2) C5 0.071(4) 0.041(3) 0.055(4) -0.012(3) 0.024(3) 0.016(3) C6 0.032(2) 0.039(2) 0.034(3) -0.005(2) 0.014(2) 0.0039(19) C7 0.033(2) 0.034(2) 0.039(3) -0.002(2) 0.021(2) 0.0014(18) C8 0.031(2) 0.041(2) 0.038(3) 0.002(2) 0.017(2) 0.0014(19) C9 0.033(3) 0.051(3) 0.036(3) 0.002(2) 0.019(2) 0.000(2) C10 0.036(3) 0.049(3) 0.033(3) 0.001(2) 0.019(2) 0.004(2) C11 0.117(6) 0.035(3) 0.043(4) 0.000(3) 0.026(4) -0.001(4) C12 0.082(4) 0.028(2) 0.032(3) 0.001(2) 0.026(3) -0.006(2) C13 0.083(4) 0.040(3) 0.035(3) 0.006(2) 0.030(3) 0.016(3) C14 0.071(4) 0.052(3) 0.037(3) -0.002(3) 0.027(3) -0.009(3) O3 0.068(5) 0.047(4) 0.055(5) 0.009(3) 0.038(4) 0.004(3) O4 0.060(9) 0.019(8) 0.090(11) 0.007(8) 0.035(8) 0.014(6) C15 0.053(7) 0.037(5) 0.046(7) -0.002(4) 0.016(5) 0.001(4) O3A 0.059(6) 0.049(5) 0.079(9) -0.006(5) 0.037(6) -0.016(4) O4A 0.060(17) 0.022(8) 0.16(3) 0.028(10) 0.08(2) 0.010(8) C15A 0.050(10) 0.047(8) 0.054(11) 0.006(7) 0.036(8) -0.001(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3A 1.768(8) . ? Zn1 O3 2.004(7) 4_566 ? Zn1 O1 2.021(4) . ? Zn1 N1 2.036(4) . ? Zn1 O4A 2.26(4) 4_566 ? Zn1 O4 2.26(3) . ? Zn1 C15A 2.482(14) . ? Zn1 C11 2.569(6) . ? O1 C11 1.237(8) . ? O2 C11 1.233(8) . ? N1 C5 1.341(7) . ? N1 C1 1.358(7) . ? C1 C2 1.384(7) . ? C2 C3 1.384(8) . ? C3 C4 1.401(7) . ? C3 C6 1.507(6) . ? C4 C5 1.388(7) . ? C6 C7 1.559(6) . ? C6 C7 1.593(6) 3_566 ? C7 C8 1.492(6) . ? C7 C6 1.593(6) 3_566 ? C8 C10 1.385(7) . ? C8 C9 1.399(7) . ? C9 C10 1.386(6) 3_466 ? C10 C9 1.386(6) 3_466 ? C11 C12 1.526(7) . ? C12 C14 1.372(8) . ? C12 C13 1.374(8) . ? C13 C14 1.393(7) 3_656 ? C14 C13 1.393(7) 3_656 ? O3 C15 1.256(12) . ? O3 Zn1 2.004(7) 4_565 ? O4 C15 1.23(3) . ? O3A C15A 1.289(18) . ? O4A C15A 1.14(5) . ? O4A Zn1 2.26(4) 4_565 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3A Zn1 O3 51.0(4) . 4_566 ? O3A Zn1 O1 141.7(3) . . ? O3 Zn1 O1 134.2(2) 4_566 . ? O3A Zn1 N1 105.7(3) . . ? O3 Zn1 N1 113.5(2) 4_566 . ? O1 Zn1 N1 103.0(2) . . ? O3A Zn1 O4A 110.8(8) . 4_566 ? O3 Zn1 O4A 60.1(8) 4_566 4_566 ? O1 Zn1 O4A 91.9(7) . 4_566 ? N1 Zn1 O4A 93.8(10) . 4_566 ? O3A Zn1 O4 52.3(9) . . ? O3 Zn1 O4 101.7(9) 4_566 . ? O1 Zn1 O4 98.7(8) . . ? N1 Zn1 O4 99.0(6) . . ? O4A Zn1 O4 161.1(5) 4_566 . ? O3A Zn1 C15A 29.7(5) . . ? O3 Zn1 C15A 79.9(5) 4_566 . ? O1 Zn1 C15A 119.0(4) . . ? N1 Zn1 C15A 102.2(4) . . ? O4A Zn1 C15A 140.1(8) 4_566 . ? O4 Zn1 C15A 22.7(8) . . ? O3A Zn1 C11 116.8(3) . . ? O3 Zn1 C11 112.1(3) 4_566 . ? O1 Zn1 C11 28.2(2) . . ? N1 Zn1 C11 130.9(2) . . ? O4A Zn1 C11 93.2(8) 4_566 . ? O4 Zn1 C11 88.9(6) . . ? C15A Zn1 C11 102.8(4) . . ? C11 O1 Zn1 101.4(5) . . ? C5 N1 C1 117.2(5) . . ? C5 N1 Zn1 121.4(4) . . ? C1 N1 Zn1 121.3(4) . . ? N1 C1 C2 122.3(6) . . ? C3 C2 C1 120.8(5) . . ? C2 C3 C4 116.8(5) . . ? C2 C3 C6 125.0(4) . . ? C4 C3 C6 118.0(5) . . ? C5 C4 C3 119.4(5) . . ? N1 C5 C4 123.4(5) . . ? C3 C6 C7 119.6(4) . . ? C3 C6 C7 115.5(4) . 3_566 ? C7 C6 C7 90.3(3) . 3_566 ? C8 C7 C6 117.2(4) . . ? C8 C7 C6 114.7(4) . 3_566 ? C6 C7 C6 89.7(3) . 3_566 ? C10 C8 C9 118.4(4) . . ? C10 C8 C7 119.5(5) . . ? C9 C8 C7 121.7(4) . . ? C10 C9 C8 120.7(4) 3_466 . ? C8 C10 C9 120.9(5) . 3_466 ? O2 C11 O1 123.2(6) . . ? O2 C11 C12 119.2(6) . . ? O1 C11 C12 117.6(7) . . ? O2 C11 Zn1 72.8(4) . . ? O1 C11 Zn1 50.5(3) . . ? C12 C11 Zn1 168.0(5) . . ? C14 C12 C13 119.8(5) . . ? C14 C12 C11 119.1(6) . . ? C13 C12 C11 121.1(5) . . ? C12 C13 C14 120.0(5) . 3_656 ? C12 C14 C13 120.2(5) . 3_656 ? C15 O3 Zn1 106.4(6) . 4_565 ? C15 O4 Zn1 120.9(18) . . ? O4 C15 O3 119.1(17) . . ? C15A O3A Zn1 107.5(9) . . ? C15A O4A Zn1 121(2) . 4_565 ? O4A C15A O3A 120.8(19) . . ? O4A C15A Zn1 79.0(17) . . ? O3A C15A Zn1 42.8(6) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.852 _refine_diff_density_min -0.785 _refine_diff_density_rms 0.089 _database_code_depnum_ccdc_archive 'CCDC 955836'