# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_section_title ;Homochiral H-bonded Proline Based Metal Organic Frameworks ; _publ_contact_author_name 'Prof. M.J.Rosseinsky' _publ_contact_author_email M.J.ROSSEINSKY@LIV.AC.UK loop_ _publ_author_name M.J.Rosseinsky 'John Bacsa' 'Michael J. Ingleson' # Attachment 'Complex-2.CIF' data_c:\frames\data-c~1\mji0515\mjr0425 _database_code_depnum_ccdc_archive 'CCDC 645631' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(Zn 2+), (C10 H8 N2), (F -), (C5 H9 N O2), (B F4 -), (H2 O)' _chemical_formula_sum 'C15 H19 B F5 N3 O3 Zn' _chemical_formula_weight 460.51 _chemical_absolute_configuration ad 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 '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_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 21' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.3839(5) _cell_length_b 7.4365(3) _cell_length_c 12.1179(5) _cell_angle_alpha 90.00 _cell_angle_beta 116.0570(10) _cell_angle_gamma 90.00 _cell_volume 921.59(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3105 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 1.403 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8724 _exptl_absorpt_correction_T_max 0.9460 _exptl_absorpt_process_details 'SADABS v2.10 (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.69110 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS, Station 16.2SMX' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker D8 diffractometer' _diffrn_measurement_method '\w scans with a narrow frame width' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7743 _diffrn_reflns_av_R_equivalents 0.0578 _diffrn_reflns_av_sigmaI/netI 0.0966 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 31.06 _reflns_number_total 4809 _reflns_number_gt 4222 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEXII (Bruker, 2004)' _computing_cell_refinement 'APEXII (Bruker, 2004)' _computing_data_reduction 'APEXII (Bruker, 2004)' _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^)+(0.0954P)^2^+0.9985P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(2) _refine_ls_number_reflns 4809 _refine_ls_number_parameters 256 _refine_ls_number_restraints 124 _refine_ls_R_factor_all 0.0728 _refine_ls_R_factor_gt 0.0676 _refine_ls_wR_factor_ref 0.1935 _refine_ls_wR_factor_gt 0.1852 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.087 _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 0.99627(4) 0.3414(5) 0.49690(4) 0.01318(13) Uani 1 1 d . . . F1 F 1.0322(2) 0.5896(6) 0.5765(2) 0.0160(4) Uani 1 1 d . . . O1 O 0.9132(3) 0.4374(6) 0.3154(3) 0.0182(6) Uani 1 1 d . . . N1 N 0.8065(3) 0.3442(12) 0.4983(3) 0.0165(6) Uani 1 1 d . . . C1 C 0.7934(5) 0.3072(9) 0.5993(4) 0.0228(10) Uani 1 1 d . . . H1 H 0.8697 0.2794 0.6722 0.027 Uiso 1 1 calc R . . O2 O 0.9126(3) 0.7410(6) 0.3200(3) 0.0183(6) Uani 1 1 d . . . N2 N 0.1843(3) 0.3497(12) 0.4975(3) 0.0167(6) Uani 1 1 d . . . C2 C 0.6728(5) 0.3072(8) 0.6036(4) 0.0205(9) Uani 1 1 d . . . H2A H 0.6676 0.2771 0.6775 0.025 Uiso 1 1 calc R . . C3 C 0.5604(4) 0.3516(12) 0.4989(4) 0.0163(7) Uani 1 1 d . . . C4 C 0.5749(4) 0.3947(9) 0.3941(4) 0.0205(8) Uani 1 1 d . . . H4 H 0.5010 0.4289 0.3210 0.025 Uiso 1 1 calc R . . C5 C 0.6987(5) 0.3875(8) 0.3966(4) 0.0218(9) Uani 1 1 d . . . H5 H 0.7069 0.4143 0.3236 0.026 Uiso 1 1 calc R . . C6 C 0.4300(4) 0.3530(12) 0.4980(4) 0.0162(7) Uani 1 1 d . . . C7 C 0.4149(4) 0.4076(8) 0.6005(4) 0.0175(8) Uani 1 1 d . . . H7 H 0.4882 0.4457 0.6728 0.021 Uiso 1 1 calc R . . C8 C 0.2896(5) 0.4057(8) 0.5953(4) 0.0181(8) Uani 1 1 d . . . H8 H 0.2793 0.4463 0.6649 0.022 Uiso 1 1 calc R . . C9 C 0.1992(4) 0.2938(8) 0.3982(4) 0.0192(9) Uani 1 1 d . . . H9 H 0.1248 0.2512 0.3285 0.023 Uiso 1 1 calc R . . C10 C 0.3197(5) 0.2964(8) 0.3945(4) 0.0185(9) Uani 1 1 d . . . H10 H 0.3267 0.2602 0.3225 0.022 Uiso 1 1 calc R . . C11 C 0.8864(4) 0.5899(8) 0.2673(3) 0.0150(6) Uani 1 1 d . . . N3 N 0.7559(9) 0.7677(13) 0.0772(8) 0.0224(11) Uiso 0.50 1 d PD A 3 H3A H 0.6696 0.7678 0.0631 0.027 Uiso 0.50 1 calc PR A 3 H3B H 0.7990 0.8607 0.1294 0.027 Uiso 0.50 1 calc PR A 3 C12 C 0.8220(15) 0.5848(19) 0.1282(13) 0.0204(9) Uiso 0.50 1 d PD A 3 H12 H 0.7525 0.4903 0.1010 0.024 Uiso 0.50 1 calc PR A 3 C13 C 0.9140(13) 0.5431(16) 0.0706(11) 0.0319(16) Uiso 0.50 1 d PD A 3 H13A H 0.9249 0.4119 0.0651 0.038 Uiso 0.50 1 calc PR A 3 H13B H 1.0009 0.5988 0.1179 0.038 Uiso 0.50 1 calc PR A 3 C14 C 0.8433(16) 0.6275(19) -0.0569(13) 0.050(2) Uiso 0.50 1 d PD A 3 H14A H 0.9068 0.6698 -0.0865 0.060 Uiso 0.50 1 calc PR A 3 H14B H 0.7838 0.5392 -0.1164 0.060 Uiso 0.50 1 calc PR A 3 C15 C 0.7691(14) 0.7789(18) -0.0420(11) 0.0386(19) Uiso 0.50 1 d PD A 3 H15A H 0.6809 0.7808 -0.1120 0.046 Uiso 0.50 1 calc PR A 3 H15B H 0.8136 0.8927 -0.0434 0.046 Uiso 0.50 1 calc PR A 3 N3B N 0.7840(9) 0.7776(13) 0.0727(8) 0.0224(11) Uiso 0.50 1 d PD A 4 H3B1 H 0.6958 0.8015 0.0381 0.027 Uiso 0.50 1 calc PR A 4 H3B2 H 0.8252 0.8602 0.1343 0.027 Uiso 0.50 1 calc PR A 4 C12B C 0.8080(15) 0.5891(19) 0.1282(13) 0.0204(9) Uiso 0.50 1 d PD A 4 H12B H 0.7242 0.5213 0.1023 0.024 Uiso 0.50 1 calc PR A 4 C13B C 0.8908(13) 0.5135(16) 0.0645(12) 0.0319(16) Uiso 0.50 1 d PD A 4 H13C H 0.9731 0.4603 0.1265 0.038 Uiso 0.50 1 calc PR A 4 H13D H 0.8412 0.4187 0.0048 0.038 Uiso 0.50 1 calc PR A 4 C14B C 0.9209(16) 0.6666(19) -0.0007(15) 0.050(2) Uiso 0.50 1 d PD A 4 H14C H 1.0100 0.7130 0.0507 0.060 Uiso 0.50 1 calc PR A 4 H14D H 0.9177 0.6235 -0.0793 0.060 Uiso 0.50 1 calc PR A 4 C15B C 0.8323(14) 0.7995(17) -0.0226(11) 0.0386(19) Uiso 0.50 1 d PD A 4 H15C H 0.7595 0.7875 -0.1060 0.046 Uiso 0.50 1 calc PR A 4 H15D H 0.8736 0.9188 -0.0155 0.046 Uiso 0.50 1 calc PR A 4 B1A B 0.5758(3) 0.1815(4) -0.0741(3) 0.047(2) Uani 0.50 1 d PDU B -1 F1A F 0.6558(5) 0.2254(8) -0.1309(5) 0.0615(13) Uani 0.50 1 d PDU B -1 F2A F 0.5351(7) 0.0023(6) -0.1001(6) 0.0615(13) Uani 0.50 1 d PDU B -1 F3A F 0.6461(7) 0.2038(10) 0.0531(5) 0.0615(13) Uani 0.50 1 d PDU B -1 F4A F 0.4662(6) 0.2944(8) -0.1185(6) 0.0615(13) Uani 0.50 1 d PDU B -1 B1B B 0.5760(3) 0.2340(4) -0.0908(3) 0.047(2) Uani 0.50 1 d PDU C -2 F1B F 0.5597(6) 0.4189(5) -0.1083(5) 0.0646(15) Uani 0.50 1 d PDU C -2 F2B F 0.4543(5) 0.1521(8) -0.1314(5) 0.0646(15) Uani 0.50 1 d PDU C -2 F3B F 0.6401(7) 0.1674(9) -0.1570(7) 0.0646(15) Uani 0.50 1 d PDU C -2 F4B F 0.6500(7) 0.1977(9) 0.0334(5) 0.0646(15) Uani 0.50 1 d PDU C -2 O1W O 0.9085(4) 0.0760(7) 0.1866(3) 0.0318(8) Uani 1 1 d D . . H1WA H 0.937(6) 0.083(11) 0.2755(19) 0.032(16) Uiso 1 1 d D . . H1WB H 0.845(7) 0.173(9) 0.152(6) 0.06(3) Uiso 1 1 d 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 0.0108(2) 0.0143(2) 0.0153(2) 0.00001(16) 0.00646(15) 0.00005(17) F1 0.0167(11) 0.0147(9) 0.0162(9) 0.0008(10) 0.0067(8) 0.0009(10) O1 0.0172(15) 0.0203(17) 0.0170(12) 0.0013(12) 0.0073(11) 0.0011(12) N1 0.0127(13) 0.0169(15) 0.0210(14) 0.004(2) 0.0084(11) 0.003(2) C1 0.0128(18) 0.033(3) 0.0212(18) 0.0008(17) 0.0064(15) 0.0011(16) O2 0.0203(15) 0.0186(16) 0.0143(13) -0.0017(11) 0.0059(12) -0.0026(12) N2 0.0132(14) 0.0188(17) 0.0191(13) -0.003(2) 0.0078(11) -0.005(2) C2 0.0153(18) 0.026(3) 0.0218(18) 0.0040(16) 0.0102(15) 0.0049(15) C3 0.0116(15) 0.0201(19) 0.0193(15) -0.001(2) 0.0088(12) 0.002(2) C4 0.0116(17) 0.028(2) 0.0207(17) 0.0050(16) 0.0063(14) 0.0011(15) C5 0.0168(19) 0.030(2) 0.0211(18) 0.0053(17) 0.0109(15) 0.0017(16) C6 0.0127(15) 0.018(2) 0.0195(15) 0.001(2) 0.0084(13) -0.001(2) C7 0.0125(17) 0.0209(18) 0.0179(17) -0.0051(15) 0.0057(14) -0.0041(15) C8 0.0158(19) 0.0219(19) 0.0179(17) -0.0030(15) 0.0087(15) 0.0008(15) C9 0.0129(18) 0.026(2) 0.0167(17) -0.0033(15) 0.0048(14) -0.0018(15) C10 0.0155(18) 0.025(2) 0.0178(17) -0.0018(14) 0.0096(15) -0.0015(15) C11 0.0119(16) 0.0189(15) 0.0148(14) 0.0009(17) 0.0065(12) -0.0013(16) B1A 0.030(4) 0.065(6) 0.025(3) -0.007(4) -0.008(3) 0.013(4) F1A 0.055(3) 0.082(3) 0.043(2) 0.010(2) 0.017(2) 0.013(3) F2A 0.055(3) 0.082(3) 0.043(2) 0.010(2) 0.017(2) 0.013(3) F3A 0.055(3) 0.082(3) 0.043(2) 0.010(2) 0.017(2) 0.013(3) F4A 0.055(3) 0.082(3) 0.043(2) 0.010(2) 0.017(2) 0.013(3) B1B 0.030(4) 0.065(6) 0.025(3) -0.007(4) -0.008(3) 0.013(4) F1B 0.053(3) 0.097(4) 0.036(2) -0.007(2) 0.013(2) -0.021(3) F2B 0.053(3) 0.097(4) 0.036(2) -0.007(2) 0.013(2) -0.021(3) F3B 0.053(3) 0.097(4) 0.036(2) -0.007(2) 0.013(2) -0.021(3) F4B 0.053(3) 0.097(4) 0.036(2) -0.007(2) 0.013(2) -0.021(3) O1W 0.046(2) 0.0275(18) 0.0219(15) 0.0017(15) 0.0150(15) 0.0024(18) _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 F1 2.036(4) 2_746 ? Zn1 F1 2.040(4) . ? Zn1 O1 2.101(3) . ? Zn1 O2 2.129(3) 2_746 ? Zn1 N2 2.138(3) 1_655 ? Zn1 N1 2.168(3) . ? F1 Zn1 2.036(4) 2_756 ? O1 C11 1.250(6) . ? N1 C1 1.325(6) . ? N1 C5 1.342(6) . ? C1 C2 1.397(6) . ? C1 H1 0.9500 . ? O2 C11 1.262(6) . ? O2 Zn1 2.129(3) 2_756 ? N2 C8 1.329(6) . ? N2 C9 1.353(6) . ? N2 Zn1 2.138(3) 1_455 ? C2 C3 1.389(6) . ? C2 H2A 0.9500 . ? C3 C4 1.388(6) . ? C3 C6 1.479(6) . ? C4 C5 1.398(6) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.387(6) . ? C6 C10 1.394(6) . ? C7 C8 1.400(6) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.392(6) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.515(15) . ? C11 C12B 1.522(15) . ? N3 C15 1.519(12) . ? N3 C12 1.546(12) . ? N3 H3A 0.9200 . ? N3 H3B 0.9200 . ? C12 C13 1.523(11) . ? C12 H12 1.0000 . ? C13 C14 1.528(15) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.465(16) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? N3B C15B 1.491(13) . ? N3B C12B 1.527(12) . ? N3B H3B1 0.9200 . ? N3B H3B2 0.9200 . ? C12B C13B 1.562(12) . ? C12B H12B 1.0000 . ? C13B C14B 1.509(15) . ? C13B H13C 0.9900 . ? C13B H13D 0.9900 . ? C14B C15B 1.352(16) . ? C14B H14C 0.9900 . ? C14B H14D 0.9900 . ? C15B H15C 0.9900 . ? C15B H15D 0.9900 . ? B1A F3A 1.400(4) . ? B1A F4A 1.400(4) . ? B1A F1A 1.400(4) . ? B1A F2A 1.400(4) . ? B1B F4B 1.391(4) . ? B1B F3B 1.391(4) . ? B1B F1B 1.391(4) . ? B1B F2B 1.391(4) . ? O1W H1WA 0.98(2) . ? O1W H1WB 0.98(7) . ? 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 F1 Zn1 F1 177.50(7) 2_746 . ? F1 Zn1 O1 86.74(12) 2_746 . ? F1 Zn1 O1 95.28(14) . . ? F1 Zn1 O2 92.53(14) 2_746 2_746 ? F1 Zn1 O2 85.40(12) . 2_746 ? O1 Zn1 O2 177.66(15) . 2_746 ? F1 Zn1 N2 89.73(19) 2_746 1_655 ? F1 Zn1 N2 88.83(19) . 1_655 ? O1 Zn1 N2 89.05(14) . 1_655 ? O2 Zn1 N2 88.72(15) 2_746 1_655 ? F1 Zn1 N1 92.5(2) 2_746 . ? F1 Zn1 N1 88.9(2) . . ? O1 Zn1 N1 90.75(14) . . ? O2 Zn1 N1 91.50(14) 2_746 . ? N2 Zn1 N1 177.7(4) 1_655 . ? Zn1 F1 Zn1 131.69(11) 2_756 . ? C11 O1 Zn1 134.6(3) . . ? C1 N1 C5 118.0(4) . . ? C1 N1 Zn1 121.5(3) . . ? C5 N1 Zn1 120.5(3) . . ? N1 C1 C2 123.1(4) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C11 O2 Zn1 137.6(3) . 2_756 ? C8 N2 C9 118.2(4) . . ? C8 N2 Zn1 121.5(3) . 1_455 ? C9 N2 Zn1 120.3(3) . 1_455 ? C3 C2 C1 119.5(4) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C4 C3 C2 117.3(4) . . ? C4 C3 C6 120.9(4) . . ? C2 C3 C6 121.8(4) . . ? C3 C4 C5 119.7(4) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? N1 C5 C4 122.4(4) . . ? N1 C5 H5 118.8 . . ? C4 C5 H5 118.8 . . ? C7 C6 C10 118.4(4) . . ? C7 C6 C3 120.9(4) . . ? C10 C6 C3 120.6(4) . . ? C6 C7 C8 118.8(4) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? N2 C8 C7 123.1(4) . . ? N2 C8 H8 118.5 . . ? C7 C8 H8 118.5 . . ? N2 C9 C10 122.3(4) . . ? N2 C9 H9 118.8 . . ? C10 C9 H9 118.8 . . ? C9 C10 C6 119.1(4) . . ? C9 C10 H10 120.4 . . ? C6 C10 H10 120.4 . . ? O1 C11 O2 128.0(3) . . ? O1 C11 C12 113.3(7) . . ? O2 C11 C12 118.5(7) . . ? O1 C11 C12B 114.7(6) . . ? O2 C11 C12B 117.2(6) . . ? C15 N3 C12 101.1(8) . . ? C15 N3 H3A 111.5 . . ? C12 N3 H3A 111.5 . . ? C15 N3 H3B 111.5 . . ? C12 N3 H3B 111.5 . . ? H3A N3 H3B 109.4 . . ? C11 C12 C13 114.9(11) . . ? C11 C12 N3 109.6(10) . . ? C13 C12 N3 107.9(8) . . ? C11 C12 H12 108.1 . . ? C13 C12 H12 108.1 . . ? N3 C12 H12 108.1 . . ? C12 C13 C14 102.5(9) . . ? C12 C13 H13A 111.3 . . ? C14 C13 H13A 111.3 . . ? C12 C13 H13B 111.3 . . ? C14 C13 H13B 111.3 . . ? H13A C13 H13B 109.2 . . ? C15 C14 C13 105.5(10) . . ? C15 C14 H14A 110.6 . . ? C13 C14 H14A 110.6 . . ? C15 C14 H14B 110.6 . . ? C13 C14 H14B 110.6 . . ? H14A C14 H14B 108.8 . . ? C14 C15 N3 112.2(9) . . ? C14 C15 H15A 109.2 . . ? N3 C15 H15A 109.2 . . ? C14 C15 H15B 109.2 . . ? N3 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C15B N3B C12B 112.7(8) . . ? C15B N3B H3B1 109.1 . . ? C12B N3B H3B1 109.1 . . ? C15B N3B H3B2 109.1 . . ? C12B N3B H3B2 109.1 . . ? H3B1 N3B H3B2 107.8 . . ? C11 C12B N3B 112.9(11) . . ? C11 C12B C13B 111.2(10) . . ? N3B C12B C13B 98.2(7) . . ? C11 C12B H12B 111.3 . . ? N3B C12B H12B 111.3 . . ? C13B C12B H12B 111.3 . . ? C14B C13B C12B 108.2(9) . . ? C14B C13B H13C 110.1 . . ? C12B C13B H13C 110.1 . . ? C14B C13B H13D 110.1 . . ? C12B C13B H13D 110.1 . . ? H13C C13B H13D 108.4 . . ? C15B C14B C13B 109.4(11) . . ? C15B C14B H14C 109.8 . . ? C13B C14B H14C 109.8 . . ? C15B C14B H14D 109.8 . . ? C13B C14B H14D 109.8 . . ? H14C C14B H14D 108.2 . . ? C14B C15B N3B 105.4(10) . . ? C14B C15B H15C 110.7 . . ? N3B C15B H15C 110.7 . . ? C14B C15B H15D 110.7 . . ? N3B C15B H15D 110.7 . . ? H15C C15B H15D 108.8 . . ? F3A B1A F4A 109.48(6) . . ? F3A B1A F1A 109.47(6) . . ? F4A B1A F1A 109.48(6) . . ? F3A B1A F2A 109.47(6) . . ? F4A B1A F2A 109.46(6) . . ? F1A B1A F2A 109.47(6) . . ? F4B B1B F3B 109.49(6) . . ? F4B B1B F1B 109.48(6) . . ? F3B B1B F1B 109.47(6) . . ? F4B B1B F2B 109.49(6) . . ? F3B B1B F2B 109.45(6) . . ? F1B B1B F2B 109.46(6) . . ? H1WA O1W H1WB 105(4) . . ? _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 31.06 _diffrn_measured_fraction_theta_full 0.913 _refine_diff_density_max 1.536 _refine_diff_density_min -0.922 _refine_diff_density_rms 0.150 # Attachment 'Complex-1.CIF' data_c:\frames\data-c~1\mjr0359\mjr0359 _database_code_depnum_ccdc_archive 'CCDC 645632' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(Cd 2+), (C10 H8 N2), (N O3 2-), (C5 H8 N O2)' _chemical_formula_sum 'C15 H16 Cd N4 O5' _chemical_formula_weight 444.72 _chemical_absolute_configuration ad 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_H-M 'P 21 21 21' 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 9.5774(12) _cell_length_b 11.8132(15) _cell_length_c 14.7182(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1665.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.774 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 1.346 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9236 _exptl_absorpt_correction_T_max 0.9736 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.78480 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS, Station 16.2SMX' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker D8 diffractometer' _diffrn_measurement_method '\w scans with a narrow frame width' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 14605 _diffrn_reflns_av_R_equivalents 0.0874 _diffrn_reflns_av_sigmaI/netI 0.0976 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 33.17 _reflns_number_total 4458 _reflns_number_gt 4064 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEXII (Bruker, 2004)' _computing_cell_refinement 'APEXII (Bruker, 2004)' _computing_data_reduction 'APEXII (Bruker, 2004)' _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^)+(0.0025P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(3) _refine_ls_number_reflns 4458 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0872 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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 Cd1 Cd 0.57543(3) 0.21863(3) 0.44049(2) 0.00754(8) Uani 1 1 d . . . N2 N 0.5722(4) 0.4217(3) 0.4427(2) 0.0094(7) Uani 1 1 d . . . O3 O 0.8822(3) 0.2757(3) 0.6531(2) 0.0126(6) Uani 1 1 d . . . C2 C 0.5827(5) 0.6590(4) 0.4337(3) 0.0088(8) Uani 1 1 d . . . O1 O 0.7855(3) 0.2290(3) 0.5208(2) 0.0123(7) Uani 1 1 d . . . N6 N 0.5924(4) 1.0218(3) 0.4226(3) 0.0127(9) Uani 1 1 d . . . O7 O 0.6796(3) 0.2469(3) 0.2961(2) 0.0145(8) Uani 1 1 d . . . C8 C 0.6418(4) 0.2262(4) 0.6565(3) 0.0120(9) Uani 1 1 d . . . H8 H 0.6189 0.2963 0.6915 0.014 Uiso 1 1 calc R . . O9 O 0.8424(3) 0.1230(3) 0.3251(2) 0.0165(8) Uani 1 1 d . . . N10 N 0.7767(4) 0.1799(3) 0.2691(3) 0.0144(9) Uani 1 1 d . . . O11 O 0.8011(4) 0.1751(3) 0.1856(2) 0.0241(9) Uani 1 1 d . . . C12 C 0.6093(5) 0.4852(4) 0.5154(3) 0.0134(11) Uani 1 1 d . . . H12 H 0.6317 0.4476 0.5705 0.016 Uiso 1 1 calc R . . C13 C 0.5398(5) 0.4774(4) 0.3670(3) 0.0104(10) Uani 1 1 d . . . H13 H 0.5121 0.4343 0.3155 0.012 Uiso 1 1 calc R . . C14 C 0.5438(5) 0.5944(4) 0.3586(3) 0.0131(11) Uani 1 1 d . . . H14 H 0.5206 0.6298 0.3026 0.016 Uiso 1 1 calc R . . C15 C 0.6162(5) 0.6022(4) 0.5133(3) 0.0136(10) Uani 1 1 d . . . H15 H 0.6435 0.6433 0.5659 0.016 Uiso 1 1 calc R . . C18 C 0.6937(5) 0.8472(4) 0.4702(3) 0.0117(9) Uani 1 1 d . . . H18 H 0.7660 0.8096 0.5025 0.014 Uiso 1 1 calc R . . C19 C 0.4898(5) 0.9620(4) 0.3812(3) 0.0119(10) Uani 1 1 d . . . H19 H 0.4178 1.0023 0.3508 0.014 Uiso 1 1 calc R . . C20 C 0.6918(5) 0.9635(4) 0.4644(3) 0.0136(10) Uani 1 1 d . . . H20 H 0.7660 1.0044 0.4920 0.016 Uiso 1 1 calc R . . C6 C 0.5874(4) 0.7850(4) 0.4280(3) 0.0085(8) Uani 1 1 d . . . C3 C 0.4852(5) 0.8450(4) 0.3813(3) 0.0129(10) Uani 1 1 d . . . H3 H 0.4131 0.8061 0.3499 0.015 Uiso 1 1 calc R . . C9 C 0.4995(5) 0.0825(5) 0.7262(3) 0.0176(11) Uani 1 1 d . . . H9A H 0.4947 0.0031 0.7476 0.021 Uiso 1 1 calc R . . H9B H 0.4402 0.1305 0.7656 0.021 Uiso 1 1 calc R . . C5 C 0.4571(5) 0.0924(4) 0.6270(3) 0.0156(10) Uani 1 1 d . . . H5A H 0.4923 0.0270 0.5917 0.019 Uiso 1 1 calc R . . H5B H 0.3542 0.0957 0.6210 0.019 Uiso 1 1 calc R . . C11 C 0.6496(5) 0.1252(5) 0.7236(4) 0.0218(12) Uani 1 1 d . . . H11A H 0.7140 0.0659 0.7011 0.026 Uiso 1 1 calc R . . H11B H 0.6808 0.1503 0.7845 0.026 Uiso 1 1 calc R . . N8 N 0.5220(4) 0.1996(3) 0.5946(2) 0.0095(8) Uani 1 1 d . . . C1 C 0.7792(5) 0.2451(3) 0.6058(3) 0.0077(9) Uani 1 1 d . . . H4 H 0.451(6) 0.262(5) 0.613(4) 0.032(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 Cd1 0.01358(14) 0.00324(13) 0.00581(14) 0.00027(13) -0.00079(14) -0.00065(13) N2 0.0124(17) 0.0083(17) 0.0076(16) 0.0013(15) 0.000(2) 0.0002(15) O3 0.0116(15) 0.0131(16) 0.0132(15) -0.0033(15) -0.0024(12) -0.0005(14) C2 0.0106(19) 0.0063(19) 0.010(2) -0.0036(17) 0.007(2) -0.0007(17) O1 0.0119(15) 0.0155(17) 0.0096(14) 0.0013(15) 0.0003(12) -0.0033(16) N6 0.016(2) 0.0081(18) 0.014(2) 0.0011(15) -0.0041(17) 0.0004(16) O7 0.0213(18) 0.0106(18) 0.0116(16) 0.0003(13) 0.0040(14) 0.0079(13) C8 0.011(2) 0.011(2) 0.014(2) 0.002(2) -0.0021(17) 0.001(2) O9 0.0156(18) 0.0210(19) 0.0129(17) 0.0012(15) -0.0016(15) 0.0044(14) N10 0.018(2) 0.014(2) 0.011(2) -0.0089(16) 0.0008(17) 0.0001(17) O11 0.036(2) 0.029(2) 0.0075(17) -0.0048(16) 0.0073(16) 0.0061(17) C12 0.022(3) 0.011(2) 0.007(2) 0.0080(18) -0.0031(18) 0.0012(19) C13 0.017(3) 0.009(2) 0.006(2) 0.0002(17) -0.0056(18) -0.0012(17) C14 0.022(3) 0.007(2) 0.010(2) 0.0006(18) -0.0001(19) 0.0016(19) C15 0.023(3) 0.008(2) 0.010(2) -0.0026(19) -0.0028(19) 0.0004(19) C18 0.018(2) 0.008(2) 0.009(2) 0.0012(18) -0.0016(18) 0.0039(19) C19 0.015(2) 0.006(2) 0.014(2) 0.0006(19) -0.005(2) 0.0013(19) C20 0.015(2) 0.008(2) 0.018(3) -0.0023(18) -0.0029(19) -0.0027(18) C6 0.014(2) 0.0066(19) 0.0046(18) -0.0001(17) 0.0028(19) 0.002(2) C3 0.016(2) 0.014(3) 0.008(2) 0.0009(19) -0.0035(19) -0.001(2) C9 0.016(2) 0.021(3) 0.016(3) 0.012(2) -0.001(2) -0.003(2) C5 0.015(3) 0.015(3) 0.017(2) 0.004(2) -0.0014(19) -0.0024(19) C11 0.020(3) 0.026(3) 0.020(3) 0.015(2) -0.002(2) -0.002(2) N8 0.0074(17) 0.013(2) 0.0081(17) 0.0005(15) 0.0003(14) 0.0015(15) C1 0.014(2) 0.003(2) 0.006(2) 0.0021(15) -0.0015(18) 0.0029(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 O3 2.308(3) 3_456 ? Cd1 N8 2.335(4) . ? Cd1 O1 2.336(3) . ? Cd1 N6 2.345(4) 1_545 ? Cd1 O7 2.371(3) . ? Cd1 N2 2.399(3) . ? N2 C13 1.331(5) . ? N2 C12 1.353(6) . ? O3 C1 1.261(5) . ? O3 Cd1 2.308(3) 3_556 ? C2 C15 1.388(6) . ? C2 C14 1.393(6) . ? C2 C6 1.492(5) . ? O1 C1 1.266(5) . ? N6 C20 1.326(6) . ? N6 C19 1.355(6) . ? N6 Cd1 2.345(4) 1_565 ? O7 N10 1.284(5) . ? C8 N8 1.498(5) . ? C8 C1 1.529(6) . ? C8 C11 1.551(7) . ? C8 H8 1.0000 . ? O9 N10 1.236(5) . ? N10 O11 1.252(5) . ? C12 C15 1.384(7) . ? C12 H12 0.9500 . ? C13 C14 1.389(6) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C18 C20 1.377(7) . ? C18 C6 1.401(6) . ? C18 H18 0.9500 . ? C19 C3 1.384(7) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C6 C3 1.390(6) . ? C3 H3 0.9500 . ? C9 C5 1.520(7) . ? C9 C11 1.525(7) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C5 N8 1.490(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? N8 H4 1.04(6) . ? 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 O3 Cd1 N8 113.99(12) 3_456 . ? O3 Cd1 O1 172.22(11) 3_456 . ? N8 Cd1 O1 72.69(11) . . ? O3 Cd1 N6 91.01(13) 3_456 1_545 ? N8 Cd1 N6 91.65(14) . 1_545 ? O1 Cd1 N6 92.81(13) . 1_545 ? O3 Cd1 O7 78.38(11) 3_456 . ? N8 Cd1 O7 167.38(12) . . ? O1 Cd1 O7 94.80(11) . . ? N6 Cd1 O7 90.58(12) 1_545 . ? O3 Cd1 N2 88.21(13) 3_456 . ? N8 Cd1 N2 94.58(13) . . ? O1 Cd1 N2 87.22(13) . . ? N6 Cd1 N2 173.47(13) 1_545 . ? O7 Cd1 N2 82.92(11) . . ? C13 N2 C12 116.7(4) . . ? C13 N2 Cd1 119.0(3) . . ? C12 N2 Cd1 124.2(3) . . ? C1 O3 Cd1 107.8(3) . 3_556 ? C15 C2 C14 117.9(4) . . ? C15 C2 C6 121.5(4) . . ? C14 C2 C6 120.7(4) . . ? C1 O1 Cd1 117.8(3) . . ? C20 N6 C19 117.3(4) . . ? C20 N6 Cd1 120.8(3) . 1_565 ? C19 N6 Cd1 121.1(3) . 1_565 ? N10 O7 Cd1 119.7(3) . . ? N8 C8 C1 113.1(4) . . ? N8 C8 C11 105.3(4) . . ? C1 C8 C11 112.4(4) . . ? N8 C8 H8 108.6 . . ? C1 C8 H8 108.6 . . ? C11 C8 H8 108.6 . . ? O9 N10 O11 122.3(4) . . ? O9 N10 O7 119.8(4) . . ? O11 N10 O7 117.8(4) . . ? N2 C12 C15 123.3(4) . . ? N2 C12 H12 118.3 . . ? C15 C12 H12 118.3 . . ? N2 C13 C14 124.0(4) . . ? N2 C13 H13 118.0 . . ? C14 C13 H13 118.0 . . ? C13 C14 C2 118.8(4) . . ? C13 C14 H14 120.6 . . ? C2 C14 H14 120.6 . . ? C12 C15 C2 119.3(4) . . ? C12 C15 H15 120.4 . . ? C2 C15 H15 120.4 . . ? C20 C18 C6 119.1(4) . . ? C20 C18 H18 120.4 . . ? C6 C18 H18 120.4 . . ? N6 C19 C3 122.9(4) . . ? N6 C19 H19 118.5 . . ? C3 C19 H19 118.5 . . ? N6 C20 C18 123.8(4) . . ? N6 C20 H20 118.1 . . ? C18 C20 H20 118.1 . . ? C3 C6 C18 117.6(4) . . ? C3 C6 C2 121.0(4) . . ? C18 C6 C2 121.4(4) . . ? C19 C3 C6 119.2(4) . . ? C19 C3 H3 120.4 . . ? C6 C3 H3 120.4 . . ? C5 C9 C11 101.7(4) . . ? C5 C9 H9A 111.4 . . ? C11 C9 H9A 111.4 . . ? C5 C9 H9B 111.4 . . ? C11 C9 H9B 111.4 . . ? H9A C9 H9B 109.3 . . ? N8 C5 C9 105.2(4) . . ? N8 C5 H5A 110.7 . . ? C9 C5 H5A 110.7 . . ? N8 C5 H5B 110.7 . . ? C9 C5 H5B 110.7 . . ? H5A C5 H5B 108.8 . . ? C9 C11 C8 103.0(4) . . ? C9 C11 H11A 111.2 . . ? C8 C11 H11A 111.2 . . ? C9 C11 H11B 111.2 . . ? C8 C11 H11B 111.2 . . ? H11A C11 H11B 109.1 . . ? C5 N8 C8 107.6(4) . . ? C5 N8 Cd1 119.0(3) . . ? C8 N8 Cd1 113.8(3) . . ? C5 N8 H4 104(3) . . ? C8 N8 H4 101(3) . . ? Cd1 N8 H4 109(3) . . ? O3 C1 O1 123.4(4) . . ? O3 C1 C8 116.5(4) . . ? O1 C1 C8 120.1(4) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 33.17 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 1.071 _refine_diff_density_min -1.113 _refine_diff_density_rms 0.158