# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Chao Qin' _publ_contact_author_email QINC703@HOTMAIL.COM _publ_section_title ; Metal-organic replica of chiral natural material ?-SnF2: an enantiopure (3,5)-connected net based on triangular and trigonal bipyramidal coordination ; loop_ _publ_author_name 'Chao Qin' 'Xinlong Wang' # Attachment 'ccdc-739181.cif' data_www _database_code_depnum_ccdc_archive 'CCDC 739181' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Cd N4 O4' _chemical_formula_weight 390.67 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.938(5) _cell_length_b 11.859(5) _cell_length_c 13.215(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 1400.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 8656 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 28.30 _exptl_crystal_description clock _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.853 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 1.581 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.540 _exptl_absorpt_correction_T_max 0.577 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8656 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3288 _reflns_number_gt 2641 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _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^)+(0.0187P)^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 SHELXL _refine_ls_extinction_coef 0.0010(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(3) _refine_ls_number_reflns 3288 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0582 _refine_ls_wR_factor_gt 0.0534 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.31991(3) 0.74641(3) 1.023570(19) 0.02964(9) Uani 1 1 d . . . C1 C 0.2342(5) 0.5079(4) 0.9285(3) 0.0375(11) Uani 1 1 d . . . H1A H 0.1520 0.5045 0.9716 0.045 Uiso 1 1 calc R . . C2 C 0.2708(5) 0.4281(4) 0.8597(3) 0.0345(11) Uani 1 1 d . . . H2A H 0.2206 0.3609 0.8471 0.041 Uiso 1 1 calc R . . C3 C 0.4322(4) 0.5659(3) 0.8551(3) 0.0285(10) Uani 1 1 d . . . H3A H 0.5149 0.6093 0.8374 0.034 Uiso 1 1 calc R . . C4 C 0.4855(5) 0.4094(4) 0.7351(3) 0.0354(11) Uani 1 1 d . . . H4A H 0.5554 0.4641 0.7059 0.042 Uiso 1 1 calc R . . C5 C 0.3848(5) 0.3638(4) 0.6492(3) 0.0297(10) Uani 1 1 d . . . C6 C 0.5757(6) 0.3154(5) 0.7830(4) 0.0648(18) Uani 1 1 d . . . H6A H 0.6388 0.3459 0.8350 0.097 Uiso 1 1 calc R . . H6B H 0.6365 0.2798 0.7323 0.097 Uiso 1 1 calc R . . H6C H 0.5091 0.2607 0.8120 0.097 Uiso 1 1 calc R . . C7 C 0.2106(6) 1.0929(4) 0.9430(3) 0.0428(12) Uani 1 1 d . . . H7A H 0.2256 1.1702 0.9498 0.051 Uiso 1 1 calc R . . C8 C 0.2807(5) 1.0117(4) 0.9937(3) 0.0418(12) Uani 1 1 d . . . H8A H 0.3539 1.0233 1.0426 0.050 Uiso 1 1 calc R . . C9 C 0.1291(5) 0.9302(4) 0.8935(3) 0.0323(10) Uani 1 1 d . . . H9A H 0.0760 0.8753 0.8583 0.039 Uiso 1 1 calc R . . C10 C 0.0155(5) 1.0948(4) 0.8037(3) 0.0403(12) Uani 1 1 d . . . H10A H -0.0497 1.0361 0.7759 0.048 Uiso 1 1 calc R . . C11 C 0.1060(6) 1.1431(4) 0.7158(3) 0.0356(11) Uani 1 1 d . . . C12 C -0.0837(6) 1.1821(5) 0.8516(4) 0.078(2) Uani 1 1 d . . . H12A H -0.1396 1.1483 0.9057 0.118 Uiso 1 1 calc R . . H12B H -0.1515 1.2114 0.8018 0.118 Uiso 1 1 calc R . . H12C H -0.0233 1.2423 0.8779 0.118 Uiso 1 1 calc R . . N1 N 0.3346(4) 0.5939(3) 0.9257(2) 0.0291(8) Uani 1 1 d . . . N2 N 0.3970(4) 0.4669(3) 0.8123(2) 0.0278(8) Uani 1 1 d . . . N3 N 0.2291(4) 0.9083(3) 0.9630(2) 0.0302(8) Uani 1 1 d . . . N4 N 0.1123(4) 1.0410(3) 0.8789(2) 0.0304(8) Uani 1 1 d . . . O1 O 0.4470(3) 0.3044(2) 0.5831(2) 0.0323(7) Uani 1 1 d . . . O2 O 0.2502(4) 0.3885(3) 0.6495(2) 0.0375(8) Uani 1 1 d . . . O3 O 0.2425(4) 1.1323(3) 0.7157(3) 0.0569(11) Uani 1 1 d . . . O4 O 0.0306(3) 1.1886(3) 0.6463(2) 0.0406(8) 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 Cd1 0.03898(16) 0.02634(14) 0.02359(14) 0.00053(19) 0.00165(13) 0.0049(2) C1 0.033(3) 0.048(3) 0.032(3) -0.005(2) 0.010(2) -0.004(2) C2 0.036(3) 0.035(2) 0.032(3) -0.002(2) 0.003(2) -0.010(2) C3 0.023(2) 0.034(2) 0.028(2) -0.0035(19) 0.0021(18) -0.0052(18) C4 0.029(3) 0.040(3) 0.037(3) -0.012(2) 0.0013(19) 0.001(2) C5 0.036(3) 0.029(2) 0.024(2) 0.0011(19) -0.002(2) -0.002(2) C6 0.063(4) 0.077(4) 0.054(4) -0.028(3) -0.032(3) 0.040(3) C7 0.063(4) 0.025(2) 0.040(3) 0.0020(19) -0.013(2) -0.001(2) C8 0.049(3) 0.037(2) 0.039(3) 0.001(2) -0.014(2) -0.005(2) C9 0.031(2) 0.033(2) 0.033(3) 0.004(2) 0.0048(19) -0.0018(19) C10 0.033(3) 0.052(3) 0.036(3) 0.018(2) -0.004(2) 0.000(2) C11 0.043(3) 0.037(3) 0.026(3) 0.004(2) 0.003(2) 0.005(2) C12 0.058(4) 0.110(5) 0.068(4) 0.042(3) 0.034(3) 0.047(3) N1 0.032(2) 0.0289(18) 0.0266(19) -0.0046(14) 0.0027(17) -0.0034(17) N2 0.029(2) 0.0294(19) 0.0251(19) -0.0075(15) 0.0028(15) -0.0020(16) N3 0.033(2) 0.0307(19) 0.027(2) 0.0036(16) 0.0011(16) 0.0043(15) N4 0.032(2) 0.032(2) 0.027(2) 0.0089(15) -0.0016(16) 0.0017(16) O1 0.0344(17) 0.0333(16) 0.0293(17) -0.0088(13) 0.0021(13) 0.0034(13) O2 0.0326(18) 0.047(2) 0.0329(19) -0.0072(16) -0.0068(16) 0.0046(15) O3 0.038(2) 0.079(3) 0.054(2) 0.023(2) 0.018(2) 0.0181(19) O4 0.0457(19) 0.0456(18) 0.0305(18) 0.0108(14) -0.0060(15) -0.0052(16) _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 Cd1 N1 2.227(3) . ? Cd1 N3 2.232(3) . ? Cd1 O4 2.238(3) 2_575 ? Cd1 O2 2.391(3) 2_565 ? Cd1 O1 2.583(3) 2_565 ? Cd1 O1 2.608(3) 4_656 ? C1 C2 1.353(6) . ? C1 N1 1.359(5) . ? C2 N2 1.370(5) . ? C3 N1 1.320(5) . ? C3 N2 1.341(5) . ? C4 N2 1.460(5) . ? C4 C6 1.515(6) . ? C4 C5 1.546(6) . ? C5 O2 1.239(5) . ? C5 O1 1.253(5) . ? C7 C8 1.330(6) . ? C7 N4 1.366(5) . ? C8 N3 1.372(5) . ? C9 N3 1.308(5) . ? C9 N4 1.337(5) . ? C10 N4 1.464(5) . ? C10 C12 1.503(7) . ? C10 C11 1.527(6) . ? C11 O3 1.227(5) . ? C11 O4 1.260(5) . ? O1 Cd1 2.583(3) 2_564 ? O1 Cd1 2.608(3) 4_646 ? O2 Cd1 2.391(3) 2_564 ? O4 Cd1 2.238(3) 2_574 ? 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 Cd1 N3 120.76(12) . . ? N1 Cd1 O4 131.70(12) . 2_575 ? N3 Cd1 O4 100.41(12) . 2_575 ? N1 Cd1 O2 82.89(12) . 2_565 ? N3 Cd1 O2 136.83(12) . 2_565 ? O4 Cd1 O2 83.26(11) 2_575 2_565 ? N1 Cd1 O1 92.41(11) . 2_565 ? N3 Cd1 O1 88.50(11) . 2_565 ? O4 Cd1 O1 114.26(10) 2_575 2_565 ? O2 Cd1 O1 52.43(10) 2_565 2_565 ? N1 Cd1 O1 81.55(11) . 4_656 ? N3 Cd1 O1 82.54(11) . 4_656 ? O4 Cd1 O1 79.86(11) 2_575 4_656 ? O2 Cd1 O1 139.60(10) 2_565 4_656 ? O1 Cd1 O1 164.57(6) 2_565 4_656 ? C2 C1 N1 110.3(4) . . ? C1 C2 N2 105.7(4) . . ? N1 C3 N2 111.3(3) . . ? N2 C4 C6 109.9(4) . . ? N2 C4 C5 111.2(4) . . ? C6 C4 C5 111.0(4) . . ? O2 C5 O1 124.4(4) . . ? O2 C5 C4 118.8(4) . . ? O1 C5 C4 116.8(4) . . ? C8 C7 N4 106.8(4) . . ? C7 C8 N3 109.9(4) . . ? N3 C9 N4 111.9(4) . . ? N4 C10 C12 111.2(4) . . ? N4 C10 C11 111.5(4) . . ? C12 C10 C11 112.0(4) . . ? O3 C11 O4 125.2(5) . . ? O3 C11 C10 119.2(4) . . ? O4 C11 C10 115.5(4) . . ? C3 N1 C1 105.5(3) . . ? C3 N1 Cd1 130.8(3) . . ? C1 N1 Cd1 123.7(3) . . ? C3 N2 C2 107.1(3) . . ? C3 N2 C4 125.2(4) . . ? C2 N2 C4 127.5(4) . . ? C9 N3 C8 105.1(4) . . ? C9 N3 Cd1 132.2(3) . . ? C8 N3 Cd1 122.7(3) . . ? C9 N4 C7 106.4(4) . . ? C9 N4 C10 126.3(4) . . ? C7 N4 C10 127.2(4) . . ? C5 O1 Cd1 86.2(3) . 2_564 ? C5 O1 Cd1 151.6(3) . 4_646 ? Cd1 O1 Cd1 120.79(11) 2_564 4_646 ? C5 O2 Cd1 95.5(3) . 2_564 ? C11 O4 Cd1 110.8(3) . 2_574 ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.522 _refine_diff_density_min -0.484 _refine_diff_density_rms 0.085