# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_General _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef 'ZnJabdcdabco.cif' _audit_creation_date 2012-01-19 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ? #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Susumu Kitagawa' _publ_contact_author_email kitagawa@sbchem.kyoto-u.ac.jp _publ_contact_author_fax +81-75-383-2732 _publ_contact_author_phone +81-75-383-2733 _publ_contact_author_address 'Institute for Integrated Cell-Material Sciences, Kyoto University iCeMS complex 2, Yoshida, Sakyo-ku, 606-8501 Kyoto, Japan' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_category 'CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; ENTER SECTION TITLE ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Kenji Hirai' ; FIRST AUTHORS FOOTNOTES ; ; Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan ; 'Shuhei Furukawa' '' '' 'Mio Kondo' '' '' 'Mikhail Meilikov' '' '' 'Yoko Sakata' '' '' 'Osami Sakata' '' '' ; S.Kitagawa ; '' '' _publ_section_synopsis ; ENTER SYNOPSIS ; #============================================================================== # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Rigaku (2010). CrystalStructure. Version 4.0. Rigaku Corporation, Tokyo, Japan. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M., Polidori, G., and Camalli, M. (1994) J. Appl. Cryst., 27, 435. SIR92 Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122. Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan. ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; #============================================================================== data_ZnJ_abdc_dabco _database_code_depnum_ccdc_archive 'CCDC 867374' #TrackingRef 'ZnJabdcdabco.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C22 H22 N4 O8 Zn2' _chemical_formula_moiety 'C22 H22 N4 O8 Zn2' _chemical_formula_weight 601.20 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 4/m m m' _symmetry_space_group_name_Hall '-P 4 2' _symmetry_Int_Tables_number 123 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -Y,+X,+Z 3 -X,-Y,+Z 4 +Y,-X,+Z 5 -X,+Y,+Z 6 +Y,+X,+Z 7 +X,-Y,+Z 8 -Y,-X,+Z 9 -X,-Y,-Z 10 +Y,-X,-Z 11 +X,+Y,-Z 12 -Y,+X,-Z 13 +X,-Y,-Z 14 -Y,-X,-Z 15 -X,+Y,-Z 16 +Y,+X,-Z #------------------------------------------------------------------------------ _cell_length_a 10.9681(9) _cell_length_b 10.9681(9) _cell_length_c 9.7190(10) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1169.19(19) _cell_formula_units_Z 1 _cell_measurement_reflns_used 3820 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 31.49 _cell_measurement_temperature 223 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 0.854 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 306.00 _exptl_absorpt_coefficient_mu 1.054 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.551 _exptl_absorpt_correction_T_max 0.810 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 223 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.314 _diffrn_reflns_number 10813 _diffrn_reflns_av_R_equivalents 0.0897 _diffrn_reflns_theta_max 31.49 _diffrn_reflns_theta_full 31.50 _diffrn_measured_fraction_theta_max 0.965 _diffrn_measured_fraction_theta_full 0.965 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1147 _reflns_number_gt 923 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0815 _refine_ls_wR_factor_ref 0.3022 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment undef _refine_ls_number_reflns 1147 _refine_ls_number_parameters 42 _refine_ls_goodness_of_fit_ref 1.177 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1904P)^2^+1.7239P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 1.420 _refine_diff_density_min -1.980 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Zn Zn 0.2839 1.4301 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 1.0000 0.0000 0.15216(11) 0.0219(5) Uani 1.0 2 d . . . O8 O 1.0000 0.1825(4) 0.1147(5) 0.0456(13) Uani 1.0 8 d . . . N2 N 1.0000 0.390(3) 0.264(3) 0.098(17) Uani 0.2500 8 d . . . N4 N 1.0000 0.0000 0.3652(9) 0.0234(17) Uani 1.0 2 d . . . C3 C 1.0000 0.2357(7) 0.0000 0.0310(16) Uani 1.0 4 d . . . C5 C 1.0000 0.3717(7) 0.0000 0.0332(17) Uani 1.0 4 d . . . C6 C 1.0000 0.4369(6) 0.1222(8) 0.052(3) Uani 1.0 8 d . . . C7 C 0.956(2) 0.1145(18) 0.4184(12) 0.089(15) Uani 0.3750 16 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Zn1 0.0251(6) 0.0251(6) 0.0157(7) 0.0000 0.0000 0.0000 O8 0.081(4) 0.020(2) 0.036(3) 0.0000 0.0000 0.0010(18) N2 0.22(6) 0.035(14) 0.043(15) 0.0000 0.0000 0.005(13) N4 0.028(3) 0.028(3) 0.015(4) 0.0000 0.0000 0.0000 C3 0.033(4) 0.024(4) 0.036(4) 0.0000 0.0000 0.0000 C5 0.044(5) 0.020(4) 0.035(4) 0.0000 0.0000 0.0000 C6 0.101(7) 0.024(3) 0.033(3) 0.0000 0.0000 0.000(3) C7 0.17(4) 0.074(12) 0.024(4) 0.07(2) 0.004(7) -0.004(6) #============================================================================== _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SIR92 (Altomare, et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Zn1 O8 2.035(5) yes . . Zn1 O8 2.035(5) yes . 2_645 Zn1 O8 2.035(5) yes . 3_755 Zn1 O8 2.035(5) yes . 4_665 Zn1 N4 2.071(9) yes . . O8 C3 1.258(6) yes . . N2 C6 1.47(3) yes . . N4 C7 1.442(19) yes . . N4 C7 1.442(19) yes . 2_645 N4 C7 1.442(19) yes . 3_755 N4 C7 1.442(19) yes . 4_665 N4 C7 1.442(19) yes . 5_755 N4 C7 1.442(19) yes . 6_645 N4 C7 1.442(19) yes . 7_555 N4 C7 1.442(19) yes . 8_665 C3 C5 1.492(11) yes . . C5 C6 1.386(9) yes . . C5 C6 1.386(9) yes . 11_555 C6 C6 1.384(10) yes . 3_765 C7 C7 1.90(3) yes . 2_645 C7 C7 1.90(3) yes . 4_665 C7 C7 0.97(4) yes . 5_755 C7 C7 1.09(3) yes . 8_665 C7 C7 1.586(16) yes . 11_556 C7 C7 1.93(3) yes . 14_666 C7 C7 1.86(3) yes . 15_756 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O8 Zn1 O8 88.16(4) yes . . 2_645 O8 Zn1 O8 159.4(2) yes . . 3_755 O8 Zn1 O8 88.16(4) yes . . 4_665 O8 Zn1 N4 100.31(14) yes . . . O8 Zn1 O8 88.16(4) yes 2_645 . 3_755 O8 Zn1 O8 159.4(2) yes 2_645 . 4_665 O8 Zn1 N4 100.31(14) yes 2_645 . . O8 Zn1 O8 88.16(4) yes 3_755 . 4_665 O8 Zn1 N4 100.31(14) yes 3_755 . . O8 Zn1 N4 100.31(14) yes 4_665 . . Zn1 O8 C3 127.9(5) yes . . . Zn1 N4 C7 111.0(6) yes . . . Zn1 N4 C7 111.0(6) yes . . 2_645 Zn1 N4 C7 111.0(6) yes . . 3_755 Zn1 N4 C7 111.0(6) yes . . 4_665 Zn1 N4 C7 111.0(6) yes . . 5_755 Zn1 N4 C7 111.0(6) yes . . 6_645 Zn1 N4 C7 111.0(6) yes . . 7_555 Zn1 N4 C7 111.0(6) yes . . 8_665 C7 N4 C7 82.6(13) yes . . 2_645 C7 N4 C7 138.0(10) yes . . 3_755 C7 N4 C7 82.6(13) yes . . 4_665 C7 N4 C7 39.2(13) yes . . 5_755 C7 N4 C7 117.1(12) yes . . 6_645 C7 N4 C7 121.2(11) yes . . 7_555 C7 N4 C7 44.5(13) yes . . 8_665 C7 N4 C7 82.6(13) yes 2_645 . 3_755 C7 N4 C7 138.0(10) yes 2_645 . 4_665 C7 N4 C7 117.1(12) yes 2_645 . 5_755 C7 N4 C7 121.2(11) yes 2_645 . 6_645 C7 N4 C7 44.5(13) yes 2_645 . 7_555 C7 N4 C7 39.2(13) yes 2_645 . 8_665 C7 N4 C7 82.6(13) yes 3_755 . 4_665 C7 N4 C7 121.2(11) yes 3_755 . 5_755 C7 N4 C7 44.5(13) yes 3_755 . 6_645 C7 N4 C7 39.2(13) yes 3_755 . 7_555 C7 N4 C7 117.1(12) yes 3_755 . 8_665 C7 N4 C7 44.5(13) yes 4_665 . 5_755 C7 N4 C7 39.2(13) yes 4_665 . 6_645 C7 N4 C7 117.1(12) yes 4_665 . 7_555 C7 N4 C7 121.2(11) yes 4_665 . 8_665 C7 N4 C7 82.6(13) yes 5_755 . 6_645 C7 N4 C7 138.0(10) yes 5_755 . 7_555 C7 N4 C7 82.6(13) yes 5_755 . 8_665 C7 N4 C7 82.6(13) yes 6_645 . 7_555 C7 N4 C7 138.0(10) yes 6_645 . 8_665 C7 N4 C7 82.6(13) yes 7_555 . 8_665 O8 C3 O8 124.7(7) yes . . 11_555 O8 C3 C5 117.6(4) yes . . . O8 C3 C5 117.6(4) yes 11_555 . . C3 C5 C6 121.1(4) yes . . . C3 C5 C6 121.1(4) yes . . 11_555 C6 C5 C6 117.9(7) yes . . 11_555 N2 C6 C5 128.5(14) yes . . . N2 C6 C6 110.5(14) yes . . 3_765 C5 C6 C6 121.1(7) yes . . 3_765 N4 C7 C7 48.7(8) yes . . 2_645 N4 C7 C7 48.7(9) yes . . 4_665 N4 C7 C7 70.4(16) yes . . 5_755 N4 C7 C7 67.7(15) yes . . 8_665 N4 C7 C7 111.0(14) yes . . 11_556 N4 C7 C7 94.6(12) yes . . 14_666 N4 C7 C7 97.6(13) yes . . 15_756 C7 C7 C7 90.0(13) yes 2_645 . 4_665 C7 C7 C7 114(2) yes 2_645 . 5_755 C7 C7 C7 21.1(14) yes 2_645 . 8_665 C7 C7 C7 90.0(12) yes 2_645 . 11_556 C7 C7 C7 58.0(9) yes 2_645 . 14_666 C7 C7 C7 102.2(11) yes 2_645 . 15_756 C7 C7 C7 23.9(15) yes 4_665 . 5_755 C7 C7 C7 111.1(19) yes 4_665 . 8_665 C7 C7 C7 90.0(13) yes 4_665 . 11_556 C7 C7 C7 101.8(11) yes 4_665 . 14_666 C7 C7 C7 61.6(10) yes 4_665 . 15_756 C7 C7 C7 135(3) yes 5_755 . 8_665 C7 C7 C7 90.0(15) yes 5_755 . 11_556 C7 C7 C7 113.6(15) yes 5_755 . 14_666 C7 C7 C7 58.6(12) yes 5_755 . 15_756 C7 C7 C7 90.0(14) yes 8_665 . 11_556 C7 C7 C7 55.4(11) yes 8_665 . 14_666 C7 C7 C7 111.6(14) yes 8_665 . 15_756 C7 C7 C7 34.6(10) yes 11_556 . 14_666 C7 C7 C7 31.4(11) yes 11_556 . 15_756 C7 C7 C7 60.4(9) yes 14_666 . 15_756 loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 Zn1 O8 3.276(5) no . 11_555 Zn1 C3 2.978(7) no . 2_645 Zn1 C3 2.978(7) no . 3_755 Zn1 C3 2.978(7) no . 4_665 O8 N2 2.70(4) no . . O8 C3 3.454(7) no . 2_645 O8 C3 3.454(7) no . 4_665 O8 C6 2.791(8) no . . O8 C7 3.082(13) no . . O8 C7 3.549(16) no . 4_665 O8 C7 3.082(13) no . 5_755 O8 C7 3.549(16) no . 8_665 N2 N2 2.41(5) no . 3_765 N2 C3 3.07(3) no . . N2 C7 3.41(4) no . . N2 C7 3.41(4) no . 5_755 C5 C5 2.814(11) no . 3_765 Zn1 Zn1 2.9577(16) no . 9_755 Zn1 O8 3.276(5) no . 9_755 Zn1 O8 3.276(5) no . 10_665 Zn1 O8 3.276(5) no . 12_645 O8 Zn1 3.276(5) no . 9_755 N4 N4 2.620(13) no . 9_756 N4 C7 2.497(16) no . 9_756 N4 C7 2.497(16) no . 10_666 N4 C7 2.497(16) no . 12_646 N4 C7 2.497(16) no . 13_556 N4 C7 2.497(16) no . 16_646 C3 Zn1 2.978(7) no . 9_755 C3 O8 3.454(7) no . 10_665 C3 O8 3.454(7) no . 12_645 C5 C6 2.412(10) no . 9_765 C6 C6 2.749(11) no . 9_765 C7 N4 2.497(16) no . 9_756 C7 C7 3.12(3) no . 9_756 C7 C7 2.48(3) no . 10_666 C7 C7 2.48(3) no . 12_646 C7 C7 2.97(3) no . 13_556 C7 C7 2.93(3) no . 16_646 #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================