# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_MAF-X8_Mesitylene _database_code_depnum_ccdc_archive 'CCDC 892987' #TrackingRef 'web_deposit_cif_file_0_Jie-PengZhang_1342857955.MAF-X8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18.87 H19.16 N2 O2 Zn' _chemical_formula_weight 371.37 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 orthorhombic _symmetry_space_group_name_H-M Ibca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-x+1/2, y+1, -z+1' 'x+1, -y+1, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'x+1/2, -y, z' '-x, y, z+1/2' _cell_length_a 13.9562(9) _cell_length_b 23.5904(15) _cell_length_c 23.5858(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7765.2(9) _cell_formula_units_Z 16 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3078 _exptl_absorpt_coefficient_mu 1.276 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7008 _exptl_absorpt_correction_T_max 0.7844 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 CCD _diffrn_measurement_method '/w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17908 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3756 _reflns_number_gt 3093 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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. ; _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^)+(0.1224P)^2^+55.9944P] 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 3756 _refine_ls_number_parameters 209 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0734 _refine_ls_wR_factor_ref 0.2058 _refine_ls_wR_factor_gt 0.1920 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.37849(6) 0.22576(4) 0.50752(4) 0.0235(3) Uani 1 1 d . . . O1 O 0.4480(5) 0.2151(3) 0.5799(2) 0.0417(14) Uani 1 1 d . . . O2 O 0.3160(7) 0.2962(3) 0.5284(2) 0.057(2) Uani 1 1 d . . . N1 N 0.4515(5) 0.2592(3) 0.9391(3) 0.0351(18) Uani 1 1 d . . . N2 N 0.2990(4) 0.6567(2) 0.4963(2) 0.0209(11) Uani 1 1 d . . . C1 C 0.5000 0.2500 0.6039(6) 0.039(3) Uani 1 2 d S . . C2 C 0.5000 0.2500 0.6667(5) 0.026(3) Uani 1 2 d S . . C3 C 0.4306(7) 0.2218(4) 0.6975(3) 0.043(2) Uani 1 1 d . . . H3A H 0.3837 0.1994 0.6788 0.052 Uiso 1 1 calc R . . C4 C 0.4299(8) 0.2268(7) 0.7591(4) 0.071(4) Uani 1 1 d . . . H4A H 0.3767 0.2127 0.7798 0.085 Uiso 1 1 calc R . . C5 C 0.5000 0.2500 0.7860(6) 0.047(4) Uani 1 2 d S . . C6 C 0.5000 0.2500 0.8484(5) 0.028(3) Uani 1 2 d S . . C7 C 0.4205(8) 0.2619(4) 0.8862(4) 0.044(2) Uani 1 1 d . . . C8 C 0.3228(7) 0.2765(6) 0.8695(4) 0.062(3) Uani 1 1 d . . . H8A H 0.2837 0.2822 0.9035 0.093 Uiso 1 1 calc R . . H8B H 0.2956 0.2456 0.8469 0.093 Uiso 1 1 calc R . . H8C H 0.3236 0.3114 0.8470 0.093 Uiso 1 1 calc R . . C9 C 0.2500 0.3220(4) 0.5000 0.025(2) Uani 1 2 d S . . C10 C 0.2500 0.3851(4) 0.5000 0.0221(19) Uani 1 2 d S . . C11 C 0.3159(8) 0.4137(4) 0.5313(4) 0.045(2) Uani 1 1 d . . . H11A H 0.3618 0.3932 0.5529 0.053 Uiso 1 1 calc R . . C12 C 0.3170(7) 0.4728(4) 0.5322(4) 0.046(2) Uani 1 1 d . . . H12A H 0.3631 0.4922 0.5545 0.056 Uiso 1 1 calc R . . C13 C 0.2500 0.5041(3) 0.5000 0.0180(19) Uani 1 2 d SU . . C14 C 0.2500 0.5667(4) 0.5000 0.024(2) Uani 1 2 d S . . C15 C 0.3277(5) 0.6028(3) 0.4931(3) 0.0252(15) Uani 1 1 d U . . C16 C 0.4310(7) 0.5893(4) 0.4845(5) 0.053(3) Uani 1 1 d . . . H16A H 0.4678 0.6247 0.4824 0.079 Uiso 1 1 calc R . . H16B H 0.4389 0.5680 0.4492 0.079 Uiso 1 1 calc R . . H16C H 0.4542 0.5665 0.5164 0.079 Uiso 1 1 calc R . . C17 C 0.1533(14) 0.4310(9) 0.7728(6) 0.065(9) Uiso 0.366(12) 1 d PG A 1 C18 C 0.2430(12) 0.4128(9) 0.7548(7) 0.052(7) Uiso 0.366(12) 1 d PG A 1 H18A H 0.2947 0.4111 0.7810 0.062 Uiso 0.366(12) 1 calc PR A 1 C19 C 0.2571(11) 0.3972(10) 0.6986(8) 0.069(8) Uiso 0.366(12) 1 d PG A 1 C20 C 0.1814(15) 0.3998(10) 0.6604(6) 0.075(10) Uiso 0.366(12) 1 d PG A 1 H20A H 0.1910 0.3891 0.6220 0.090 Uiso 0.366(12) 1 calc PR A 1 C21 C 0.0916(13) 0.4179(10) 0.6784(7) 0.074(9) Uiso 0.366(12) 1 d PG A 1 C22 C 0.0776(11) 0.4335(9) 0.7346(8) 0.059(8) Uiso 0.366(12) 1 d PG A 1 H22A H 0.0162 0.4459 0.7469 0.071 Uiso 0.366(12) 1 calc PR A 1 C23 C 0.136(3) 0.443(2) 0.8328(17) 0.093(13) Uiso 0.366(12) 1 d P A 1 H23A H 0.1892 0.4281 0.8555 0.140 Uiso 0.366(12) 1 calc PR A 1 H23B H 0.0761 0.4252 0.8447 0.140 Uiso 0.366(12) 1 calc PR A 1 H23C H 0.1316 0.4842 0.8383 0.140 Uiso 0.366(12) 1 calc PR A 1 C24 C 0.360(3) 0.3820(18) 0.6806(16) 0.081(11) Uiso 0.366(12) 1 d P A 1 H24A H 0.3643 0.3828 0.6392 0.122 Uiso 0.366(12) 1 calc PR A 1 H24B H 0.3754 0.3439 0.6944 0.122 Uiso 0.366(12) 1 calc PR A 1 H24C H 0.4045 0.4095 0.6968 0.122 Uiso 0.366(12) 1 calc PR A 1 C25 C 0.013(3) 0.426(2) 0.632(2) 0.098(14) Uiso 0.366(12) 1 d P A 1 H25A H -0.0462 0.4400 0.6502 0.147 Uiso 0.366(12) 1 calc PR A 1 H25B H -0.0005 0.3893 0.6140 0.147 Uiso 0.366(12) 1 calc PR A 1 H25C H 0.0346 0.4531 0.6038 0.147 Uiso 0.366(12) 1 calc PR A 1 C26 C 0.5020(12) 0.4096(11) 0.8341(8) 0.075(10) Uiso 0.397(13) 1 d PG B 2 C27 C 0.4118(13) 0.4198(9) 0.8568(6) 0.059(7) Uiso 0.397(13) 1 d PG B 2 H27A H 0.4025 0.4187 0.8967 0.071 Uiso 0.397(13) 1 calc PR B 2 C28 C 0.3350(11) 0.4315(8) 0.8212(7) 0.058(7) Uiso 0.397(13) 1 d PG B 2 C29 C 0.3485(14) 0.4331(9) 0.7628(7) 0.074(9) Uiso 0.397(13) 1 d PG B 2 H29A H 0.2960 0.4411 0.7384 0.089 Uiso 0.397(13) 1 calc PR B 2 C30 C 0.4388(16) 0.4229(11) 0.7401(6) 0.092(11) Uiso 0.397(13) 1 d PG B 2 C31 C 0.5155(12) 0.4111(11) 0.7758(9) 0.076(10) Uiso 0.397(13) 1 d PG B 2 H31A H 0.5772 0.4041 0.7602 0.091 Uiso 0.397(13) 1 calc PR B 2 C32 C 0.590(2) 0.4028(11) 0.8754(11) 0.054(6) Uiso 0.397(13) 1 d P B 2 H32A H 0.6486 0.3978 0.8533 0.081 Uiso 0.397(13) 1 calc PR B 2 H32B H 0.5800 0.3695 0.8997 0.081 Uiso 0.397(13) 1 calc PR B 2 H32C H 0.5955 0.4367 0.8991 0.081 Uiso 0.397(13) 1 calc PR B 2 C33 C 0.241(3) 0.435(2) 0.8391(17) 0.115(14) Uiso 0.397(13) 1 d P B 2 H33A H 0.2393 0.4342 0.8806 0.172 Uiso 0.397(13) 1 calc PR B 2 H33B H 0.2048 0.4031 0.8238 0.172 Uiso 0.397(13) 1 calc PR B 2 H33C H 0.2133 0.4708 0.8256 0.172 Uiso 0.397(13) 1 calc PR B 2 C34 C 0.451(3) 0.4205(17) 0.6755(14) 0.088(10) Uiso 0.397(13) 1 d P B 2 H34A H 0.3892 0.4269 0.6572 0.132 Uiso 0.397(13) 1 calc PR B 2 H34B H 0.4759 0.3831 0.6646 0.132 Uiso 0.397(13) 1 calc PR B 2 H34C H 0.4966 0.4498 0.6636 0.132 Uiso 0.397(13) 1 calc PR B 2 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 0.0289(4) 0.0151(4) 0.0265(5) 0.0002(4) -0.0020(3) -0.0026(3) O1 0.053(4) 0.043(4) 0.029(3) -0.003(2) -0.009(3) -0.002(3) O2 0.127(7) 0.015(3) 0.029(3) 0.000(2) -0.007(3) 0.002(4) N1 0.023(4) 0.068(5) 0.014(3) -0.014(3) 0.001(3) 0.004(3) N2 0.031(3) 0.008(2) 0.024(3) -0.004(2) -0.001(3) 0.001(2) C1 0.059(10) 0.020(5) 0.037(8) 0.000 0.000 0.005(6) C2 0.034(8) 0.021(5) 0.021(6) 0.000 0.000 -0.002(4) C3 0.045(6) 0.055(5) 0.030(4) 0.001(4) -0.006(4) -0.019(5) C4 0.036(6) 0.154(11) 0.024(4) 0.038(7) -0.003(4) -0.011(7) C5 0.081(14) 0.030(6) 0.032(7) 0.000 0.000 -0.016(7) C6 0.034(8) 0.032(6) 0.018(6) 0.000 0.000 -0.005(5) C7 0.051(7) 0.046(6) 0.035(5) 0.003(3) 0.003(5) 0.012(4) C8 0.040(6) 0.114(10) 0.032(5) 0.005(6) 0.001(4) 0.008(6) C9 0.050(6) 0.009(4) 0.016(4) 0.000 0.008(4) 0.000 C10 0.029(5) 0.009(4) 0.029(5) 0.000 -0.003(5) 0.000 C11 0.044(6) 0.027(5) 0.063(6) 0.006(4) 0.006(4) 0.008(4) C12 0.043(6) 0.019(4) 0.077(6) 0.009(4) -0.012(5) -0.004(4) C13 0.028(5) 0.004(3) 0.022(5) 0.000 -0.007(4) 0.000 C14 0.025(5) 0.008(4) 0.038(6) 0.000 -0.010(5) 0.000 C15 0.031(4) 0.006(3) 0.039(4) 0.005(3) 0.009(3) 0.003(3) C16 0.028(5) 0.017(4) 0.113(8) 0.003(4) 0.009(5) 0.005(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 O2 1.940(7) . ? Zn1 N1 1.940(7) 11_565 ? Zn1 N2 1.974(5) 14_546 ? Zn1 O1 1.980(5) . ? O1 C1 1.235(9) . ? O2 C9 1.291(9) . ? N1 C7 1.323(12) . ? N1 N1 1.422(15) 6_554 ? N1 Zn1 1.940(7) 11_566 ? N2 C15 1.336(8) . ? N2 N2 1.378(12) 7_545 ? N2 Zn1 1.974(5) 14_556 ? C1 O1 1.235(9) 6_554 ? C1 C2 1.48(2) . ? C2 C3 1.382(11) . ? C2 C3 1.382(11) 6_554 ? C3 C4 1.457(13) . ? C3 H3A 0.9500 . ? C4 C5 1.288(14) . ? C4 H4A 0.9500 . ? C5 C4 1.288(14) 6_554 ? C5 C6 1.47(2) . ? C6 C7 1.450(13) . ? C6 C7 1.450(13) 6_554 ? C7 C8 1.460(15) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 O2 1.291(9) 7_545 ? C9 C10 1.490(12) . ? C10 C11 1.359(12) . ? C10 C11 1.359(12) 7_545 ? C11 C12 1.394(12) . ? C11 H11A 0.9500 . ? C12 C13 1.412(10) . ? C12 H12A 0.9500 . ? C13 C12 1.412(10) 7_545 ? C13 C14 1.478(12) . ? C14 C15 1.388(9) 7_545 ? C14 C15 1.388(9) . ? C15 C16 1.489(12) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.3900 . ? C17 C22 1.3900 . ? C17 C23 1.46(4) . ? C18 C19 1.3900 . ? C18 H18A 0.9500 . ? C19 C20 1.3900 . ? C19 C24 1.54(4) . ? C20 C21 1.3900 . ? C20 H20A 0.9500 . ? C21 C22 1.3900 . ? C21 C25 1.56(5) . ? C22 H22A 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.3900 . ? C26 C31 1.3900 . ? C26 C32 1.57(3) . ? C27 C28 1.3900 . ? C27 H27A 0.9500 . ? C28 C33 1.38(5) . ? C28 C29 1.3900 . ? C29 C30 1.3900 . ? C29 H29A 0.9500 . ? C30 C31 1.3900 . ? C30 C34 1.53(4) . ? C31 H31A 0.9500 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 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 O2 Zn1 N1 106.9(3) . 11_565 ? O2 Zn1 N2 117.8(3) . 14_546 ? N1 Zn1 N2 114.1(3) 11_565 14_546 ? O2 Zn1 O1 96.3(3) . . ? N1 Zn1 O1 118.9(3) 11_565 . ? N2 Zn1 O1 102.1(3) 14_546 . ? C1 O1 Zn1 126.8(6) . . ? C9 O2 Zn1 126.3(5) . . ? C7 N1 N1 109.0(6) . 6_554 ? C7 N1 Zn1 127.2(7) . 11_566 ? N1 N1 Zn1 123.8(2) 6_554 11_566 ? C15 N2 N2 107.8(4) . 7_545 ? C15 N2 Zn1 127.9(5) . 14_556 ? N2 N2 Zn1 124.31(16) 7_545 14_556 ? O1 C1 O1 125.4(13) . 6_554 ? O1 C1 C2 117.3(7) . . ? O1 C1 C2 117.3(7) 6_554 . ? C3 C2 C3 116.5(11) . 6_554 ? C3 C2 C1 121.8(5) . . ? C3 C2 C1 121.8(5) 6_554 . ? C2 C3 C4 119.4(9) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C5 C4 C3 121.3(10) . . ? C5 C4 H4A 119.3 . . ? C3 C4 H4A 119.3 . . ? C4 C5 C4 121.0(15) . 6_554 ? C4 C5 C6 119.5(7) . . ? C4 C5 C6 119.5(7) 6_554 . ? C7 C6 C7 104.2(11) . 6_554 ? C7 C6 C5 127.9(6) . . ? C7 C6 C5 127.9(6) 6_554 . ? N1 C7 C6 108.7(9) . . ? N1 C7 C8 124.7(9) . . ? C6 C7 C8 126.5(8) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 O2 123.8(9) 7_545 . ? O2 C9 C10 118.1(5) 7_545 . ? O2 C9 C10 118.1(5) . . ? C11 C10 C11 120.5(10) . 7_545 ? C11 C10 C9 119.8(5) . . ? C11 C10 C9 119.8(5) 7_545 . ? C10 C11 C12 120.7(9) . . ? C10 C11 H11A 119.6 . . ? C12 C11 H11A 119.6 . . ? C11 C12 C13 120.6(9) . . ? C11 C12 H12A 119.7 . . ? C13 C12 H12A 119.7 . . ? C12 C13 C12 117.0(10) 7_545 . ? C12 C13 C14 121.5(5) 7_545 . ? C12 C13 C14 121.5(5) . . ? C15 C14 C15 104.4(8) 7_545 . ? C15 C14 C13 127.8(4) 7_545 . ? C15 C14 C13 127.8(4) . . ? N2 C15 C14 110.0(6) . . ? N2 C15 C16 120.1(7) . . ? C14 C15 C16 129.9(6) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 120.0 . . ? C18 C17 C23 120(2) . . ? C22 C17 C23 120(2) . . ? C19 C18 C17 120.0 . . ? C19 C18 H18A 120.0 . . ? C17 C18 H18A 120.0 . . ? C20 C19 C18 120.0 . . ? C20 C19 C24 122.6(19) . . ? C18 C19 C24 117.2(19) . . ? C19 C20 C21 120.0 . . ? C19 C20 H20A 120.0 . . ? C21 C20 H20A 120.0 . . ? C20 C21 C22 120.0 . . ? C20 C21 C25 118(2) . . ? C22 C21 C25 122(2) . . ? C21 C22 C17 120.0 . . ? C21 C22 H22A 120.0 . . ? C17 C22 H22A 120.0 . . ? C17 C23 H23A 109.5 . . ? C17 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C17 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C19 C24 H24A 109.5 . . ? C19 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C19 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C21 C25 H25A 109.5 . . ? C21 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C21 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C31 120.0 . . ? C27 C26 C32 119.0(16) . . ? C31 C26 C32 120.7(16) . . ? C26 C27 C28 120.0 . . ? C26 C27 H27A 120.0 . . ? C28 C27 H27A 120.0 . . ? C33 C28 C27 124(2) . . ? C33 C28 C29 116(2) . . ? C27 C28 C29 120.0 . . ? C30 C29 C28 120.0 . . ? C30 C29 H29A 120.0 . . ? C28 C29 H29A 120.0 . . ? C31 C30 C29 120.0 . . ? C31 C30 C34 120(2) . . ? C29 C30 C34 119(2) . . ? C30 C31 C26 120.0 . . ? C30 C31 H31A 120.0 . . ? C26 C31 H31A 120.0 . . ? C26 C32 H32A 109.5 . . ? C26 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C26 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C28 C33 H33A 109.5 . . ? C28 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C28 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C30 C34 H34A 109.5 . . ? C30 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C30 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.826 _refine_diff_density_min -0.577 _refine_diff_density_rms 0.167 data_MAF-X8_Guest-Free _database_code_depnum_ccdc_archive 'CCDC 892988' #TrackingRef 'web_deposit_cif_file_0_Jie-PengZhang_1342857955.MAF-X8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 N2 O2 Zn' _chemical_formula_weight 279.59 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 orthorhombic _symmetry_space_group_name_H-M Ibca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-x+1/2, y+1, -z+1' 'x+1, -y+1, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'x+1/2, -y, z' '-x, y, z+1/2' _cell_length_a 13.9249(12) _cell_length_b 23.653(2) _cell_length_c 23.637(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7785.3(11) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.954 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2272 _exptl_absorpt_coefficient_mu 1.255 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7045 _exptl_absorpt_correction_T_max 0.7874 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method '/w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20982 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3819 _reflns_number_gt 3127 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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. ; _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^)+(0.0974P)^2^+9.3965P] 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 3819 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1505 _refine_ls_wR_factor_gt 0.1381 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.37948(3) 0.22384(2) 0.50696(2) 0.03244(18) Uani 1 1 d . . . O1 O 0.4499(3) 0.21376(19) 0.57892(15) 0.0589(11) Uani 1 1 d . . . O2 O 0.3138(4) 0.29446(19) 0.52944(17) 0.0737(14) Uani 1 1 d . . . N1 N 0.4532(3) 0.2601(2) 0.93861(19) 0.0498(14) Uani 1 1 d . . . N2 N 0.3001(2) 0.65506(15) 0.49768(18) 0.0330(8) Uani 1 1 d . . . C1 C 0.5000 0.2500 0.6036(4) 0.052(2) Uani 1 2 d S . . C2 C 0.5000 0.2500 0.6659(4) 0.045(2) Uani 1 2 d S . . C3 C 0.4378(5) 0.2161(4) 0.6962(2) 0.078(2) Uani 1 1 d . . . H3A H 0.3960 0.1921 0.6770 0.094 Uiso 1 1 calc R . . C4 C 0.4369(6) 0.2173(4) 0.7565(3) 0.094(3) Uani 1 1 d . . . H4A H 0.3923 0.1954 0.7758 0.113 Uiso 1 1 calc R . . C5 C 0.5000 0.2500 0.7867(4) 0.051(2) Uani 1 2 d S . . C6 C 0.5000 0.2500 0.8478(4) 0.049(2) Uani 1 2 d S . . C7 C 0.4237(5) 0.2652(3) 0.8847(3) 0.064(2) Uani 1 1 d . . . C8 C 0.3255(5) 0.2849(5) 0.8684(3) 0.106(4) Uani 1 1 d . . . H8A H 0.2875 0.2905 0.9019 0.159 Uiso 1 1 calc R . . H8B H 0.2955 0.2570 0.8448 0.159 Uiso 1 1 calc R . . H8C H 0.3304 0.3199 0.8481 0.159 Uiso 1 1 calc R . . C9 C 0.2500 0.3197(3) 0.5000 0.0489(18) Uani 1 2 d S . . C10 C 0.2500 0.3828(3) 0.5000 0.0429(16) Uani 1 2 d S . . C11 C 0.3090(5) 0.4124(3) 0.5364(3) 0.0645(19) Uani 1 1 d . . . H11A H 0.3495 0.3929 0.5608 0.077 Uiso 1 1 calc R . . C12 C 0.3087(5) 0.4710(3) 0.5369(4) 0.069(2) Uani 1 1 d . . . H12A H 0.3482 0.4900 0.5623 0.083 Uiso 1 1 calc R . . C13 C 0.2500 0.5023(3) 0.5000 0.0459(19) Uani 1 2 d S . . C14 C 0.2500 0.5645(3) 0.5000 0.0432(17) Uani 1 2 d S . . C15 C 0.3288(3) 0.60119(19) 0.4947(3) 0.0421(11) Uani 1 1 d . . . C16 C 0.4343(4) 0.5874(3) 0.4898(4) 0.080(2) Uani 1 1 d . . . H16A H 0.4706 0.6219 0.4878 0.120 Uiso 1 1 calc R . . H16B H 0.4452 0.5655 0.4562 0.120 Uiso 1 1 calc R . . H16C H 0.4543 0.5661 0.5223 0.120 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 0.0379(3) 0.0251(3) 0.0343(3) -0.0014(3) -0.0002(2) -0.0048(2) O1 0.076(3) 0.067(3) 0.0341(19) -0.0004(18) -0.0098(18) -0.009(2) O2 0.135(4) 0.028(2) 0.059(3) -0.0034(17) 0.006(3) 0.013(3) N1 0.045(3) 0.078(4) 0.027(2) -0.009(2) 0.000(2) 0.018(2) N2 0.0300(17) 0.0227(18) 0.046(2) 0.0013(18) -0.0029(18) -0.0010(14) C1 0.087(7) 0.035(4) 0.035(5) 0.000 0.000 0.005(4) C2 0.048(5) 0.060(6) 0.026(4) 0.000 0.000 -0.004(4) C3 0.082(5) 0.121(7) 0.032(3) 0.011(4) -0.005(3) -0.028(5) C4 0.088(5) 0.154(8) 0.041(3) 0.017(5) 0.006(4) -0.039(6) C5 0.053(6) 0.065(6) 0.035(4) 0.000 0.000 0.001(4) C6 0.053(6) 0.057(6) 0.038(5) 0.000 0.000 0.000(4) C7 0.055(4) 0.093(6) 0.046(4) 0.009(3) 0.001(3) 0.028(4) C8 0.064(4) 0.213(11) 0.043(4) 0.014(5) -0.001(3) 0.034(6) C9 0.080(5) 0.021(3) 0.046(4) 0.000 0.012(4) 0.000 C10 0.054(4) 0.013(3) 0.061(5) 0.000 -0.005(4) 0.000 C11 0.070(5) 0.036(4) 0.087(5) 0.008(3) -0.014(4) 0.008(3) C12 0.070(5) 0.024(3) 0.113(6) -0.004(3) -0.017(4) 0.000(3) C13 0.056(5) 0.013(3) 0.069(6) 0.000 -0.007(4) 0.000 C14 0.040(4) 0.013(3) 0.076(5) 0.000 -0.013(4) 0.000 C15 0.036(2) 0.015(2) 0.075(4) 0.006(2) 0.012(3) 0.0002(19) C16 0.040(3) 0.039(3) 0.162(7) -0.002(4) 0.011(4) 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 N1 1.951(5) 11_565 ? Zn1 N2 1.970(4) 14_546 ? Zn1 O2 1.977(5) . ? Zn1 O1 1.978(4) . ? O1 C1 1.250(6) . ? O2 C9 1.277(6) . ? N1 C7 1.343(8) . ? N1 N1 1.388(9) 6_554 ? N1 Zn1 1.951(5) 11_566 ? N2 C15 1.337(6) . ? N2 N2 1.400(7) 7_545 ? N2 Zn1 1.970(3) 14_556 ? C1 O1 1.250(6) 6_554 ? C1 C2 1.471(14) . ? C2 C3 1.381(8) 6_554 ? C2 C3 1.381(8) . ? C3 C4 1.425(10) . ? C3 H3A 0.9300 . ? C4 C5 1.371(9) . ? C4 H4A 0.9300 . ? C5 C4 1.371(9) 6_554 ? C5 C6 1.444(15) . ? C6 C7 1.422(9) 6_554 ? C6 C7 1.422(9) . ? C7 C8 1.495(10) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 O2 1.277(6) 7_545 ? C9 C10 1.491(9) . ? C10 C11 1.381(8) . ? C10 C11 1.381(8) 7_545 ? C11 C12 1.384(8) . ? C11 H11A 0.9300 . ? C12 C13 1.406(8) . ? C12 H12A 0.9300 . ? C13 C12 1.406(8) 7_545 ? C13 C14 1.473(9) . ? C14 C15 1.404(6) 7_545 ? C14 C15 1.404(6) . ? C15 C16 1.510(8) . ? 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 N1 Zn1 N2 114.2(2) 11_565 14_546 ? N1 Zn1 O2 107.6(2) 11_565 . ? N2 Zn1 O2 116.96(19) 14_546 . ? N1 Zn1 O1 118.32(17) 11_565 . ? N2 Zn1 O1 103.09(19) 14_546 . ? O2 Zn1 O1 95.7(2) . . ? C1 O1 Zn1 126.6(4) . . ? C9 O2 Zn1 124.8(4) . . ? C7 N1 N1 108.6(3) . 6_554 ? C7 N1 Zn1 127.3(4) . 11_566 ? N1 N1 Zn1 124.12(13) 6_554 11_566 ? C15 N2 N2 107.6(3) . 7_545 ? C15 N2 Zn1 128.1(3) . 14_556 ? N2 N2 Zn1 124.31(10) 7_545 14_556 ? O1 C1 O1 124.2(9) 6_554 . ? O1 C1 C2 117.9(4) 6_554 . ? O1 C1 C2 117.9(4) . . ? C3 C2 C3 117.5(8) 6_554 . ? C3 C2 C1 121.2(4) 6_554 . ? C3 C2 C1 121.2(4) . . ? C2 C3 C4 120.8(7) . . ? C2 C3 H3A 119.6 . . ? C4 C3 H3A 119.6 . . ? C5 C4 C3 121.8(7) . . ? C5 C4 H4A 119.1 . . ? C3 C4 H4A 119.1 . . ? C4 C5 C4 117.2(10) . 6_554 ? C4 C5 C6 121.4(5) . . ? C4 C5 C6 121.4(5) 6_554 . ? C7 C6 C7 104.2(8) 6_554 . ? C7 C6 C5 127.9(4) 6_554 . ? C7 C6 C5 127.9(4) . . ? N1 C7 C6 109.3(6) . . ? N1 C7 C8 123.6(6) . . ? C6 C7 C8 127.1(6) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 O2 124.2(7) . 7_545 ? O2 C9 C10 117.9(4) . . ? O2 C9 C10 117.9(4) 7_545 . ? C11 C10 C11 118.9(7) . 7_545 ? C11 C10 C9 120.5(4) . . ? C11 C10 C9 120.5(4) 7_545 . ? C10 C11 C12 120.8(6) . . ? C10 C11 H11A 119.6 . . ? C12 C11 H11A 119.6 . . ? C11 C12 C13 121.5(6) . . ? C11 C12 H12A 119.2 . . ? C13 C12 H12A 119.2 . . ? C12 C13 C12 116.4(7) . 7_545 ? C12 C13 C14 121.8(4) . . ? C12 C13 C14 121.8(4) 7_545 . ? C15 C14 C15 103.7(6) 7_545 . ? C15 C14 C13 128.2(3) 7_545 . ? C15 C14 C13 128.2(3) . . ? N2 C15 C14 110.5(4) . . ? N2 C15 C16 120.0(4) . . ? C14 C15 C16 129.4(4) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.112 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.130