Supplementary Material (ESI) for Chemical Communications This journal is (C) The Royal Society of Chemistry 2002 data_global #=============================================================================== _audit_creation_date 1-10-01 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Hosseini, M.' 'Felix, Olivier' 'Ferlay, Sylvie' 'Kyritsaka, Nathalie' 'Planeix, Jean-Marc' _publ_contact_author_name 'Prof M Hosseini' _publ_contact_author_address ; Laboratoire de Chimie de Coordination Organique Universite Louis Pasteur 4 rue Blaise Pascal 67000 Strasbourg FRANCE ; _publ_contact_author_email 'HOSSEINI@CHIMIE.U-STRASBG.FR' _publ_section_title ; Second Sphere Supramolecular Chirality: Racemic Hybrid H-Bonded 2-D Molecular Networks ; _publ_section_references ; Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. OpenMoleN, Interactive Intelligent Structure solution (1997) Nonius B.V., Delft, The Netherlands. KappaCCD Operation Manual (1997), Nonius B.V., Delft, The Nederlands. Otwinowski, Z. & Minor, W. (1997), Methods in Enzymology, 276, 307-326. Walker, N. & Stuart, D. (1983). Acta Cryst., A39, 158-166. ; data_st996 _database_code_CSD 175756 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C27 H38 Fe N12 O4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C27 H38 Fe N12 O4' _chemical_formula_weight 650.53 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 Fe ? 0.301 0.845 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P-1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' -x,-y,-z _cell_length_a 7.1092(2) _cell_length_b 12.4303(4) _cell_length_c 17.9853(6) _cell_angle_alpha 83.443(5) _cell_angle_beta 87.583(5) _cell_angle_gamma 84.059(5) _cell_volume 1569.73(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173 _cell_measurement_reflns_used 6673 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 27.4 _cell_special_details ; Cell parameters refined using Scalepack part of DENZO Z. Otwinowski, W. Minor, 1997 ; _exptl_crystal_description needle _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.38 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 0.534 _exptl_absorpt_correction_type refdelf_(Walker_&_Stuart,_1983) _exptl_absorpt_correction_T_min 0.9607 _exptl_absorpt_correction_T_max 1.0000 #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_measurement_details ; 6673 reflections were collected using program Collect ("Collect" Data collection software, Nonius B.V., 1998) The conditions were as follow : crystal to detector distance = 36. mm. Scan angle = 2.0 deg 1 scans of 60 sec per frame. Data collection was divided into 2 set(s) with the following starting angles and number of frames : Set 1 Theta = 6.30 Omega = 0.00 Kappa = 0.00 91 frames Set 2 Theta = -6.30 Kappa = -124.00 Phi = 0.00 24 frames Friedel pairs were averaged. Internal R = 0.04 ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6673 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 27.40 _reflns_number_total 6673 _reflns_number_gt 4100 _reflns_threshold_expression >3.0\s(I) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_OpenMoleN_(_1997) _computing_molecular_graphics ? _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 4100 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.093 _refine_ls_R_factor_gt 0.049 _refine_ls_wR_factor_all 0.500 _refine_ls_wR_factor_ref 0.073 _refine_ls_goodness_of_fit_all 9.547 _refine_ls_goodness_of_fit_ref 1.259 _refine_ls_shift/su_max 0.018 _refine_ls_shift/esd_mean 0.001 _refine_diff_density_max 0.598 _refine_diff_density_min -0.159 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol FE 0.23563(6) 0.71068(4) 0.72909(3) 0.0153(2) Uani ? ? Fe C1 0.1044(5) 0.5810(3) 0.7314(2) 0.019(2) Uani ? ? C N1 0.0313(4) 0.5017(3) 0.7347(2) 0.031(2) Uani ? ? N C2 0.3966(5) 0.6603(3) 0.6479(2) 0.016(2) Uani ? ? C N2 0.4777(4) 0.6350(2) 0.5948(2) 0.023(2) Uani ? ? N C3 0.0862(5) 0.7881(3) 0.6485(2) 0.018(2) Uani ? ? C N3 0.0110(4) 0.8322(2) 0.5956(2) 0.024(2) Uani ? ? N C4 0.3726(5) 0.8378(3) 0.7333(2) 0.021(2) Uani ? ? C N4 0.4528(4) 0.9133(3) 0.7371(2) 0.036(2) Uani ? ? N C5 0.0587(5) 0.7652(3) 0.8040(2) 0.019(2) Uani ? ? C N5 -0.0493(4) 0.7988(3) 0.8477(2) 0.030(2) Uani ? ? N C6 0.3939(5) 0.6285(3) 0.8049(2) 0.019(2) Uani ? ? C N6 0.4844(4) 0.5753(2) 0.8496(2) 0.027(2) Uani ? ? N C7 0.7019(5) 0.4190(3) 0.5963(2) 0.017(2) Uani ? ? C N7 0.7124(4) 0.4167(2) 0.6690(2) 0.020(1) Uani ? ? N C8 0.5660(5) 0.3776(3) 0.7213(2) 0.025(2) Uani ? ? C C9 0.4558(6) 0.3007(3) 0.6868(2) 0.035(2) Uani ? ? C C10 0.3948(5) 0.3482(3) 0.6101(2) 0.032(2) Uani ? ? C N8 0.5591(4) 0.3835(2) 0.5649(2) 0.022(1) Uani ? ? N C11 0.8551(4) 0.4605(3) 0.5464(2) 0.016(2) Uani ? ? C C12 0.9230(5) 0.5603(3) 0.5569(2) 0.019(2) Uani ? ? C C13 0.9333(5) 0.4017(3) 0.4893(2) 0.018(2) Uani ? ? C C14 0.7847(5) 0.0520(3) 0.5942(2) 0.021(2) Uani ? ? C N9 0.9264(4) 0.1025(3) 0.5628(2) 0.033(2) Uani ? ? N C15 1.0831(6) 0.1255(5) 0.6066(3) 0.066(3) Uani ? ? C C16 1.0496(7) 0.1147(6) 0.6805(3) 0.087(3) Uani ? ? C C17 0.9137(5) 0.0472(3) 0.7184(2) 0.028(2) Uani ? ? C N10 0.7693(4) 0.0270(2) 0.6671(2) 0.021(1) Uani ? ? N C18 0.6365(5) 0.0243(3) 0.5462(2) 0.018(2) Uani ? ? C C19 0.5728(5) -0.0773(3) 0.5561(2) 0.018(2) Uani ? ? C C20 0.5642(5) 0.1021(3) 0.4898(2) 0.020(2) Uani ? ? C C21 0.3400(5) 0.3540(3) 0.9956(2) 0.020(2) Uani ? ? C N11 0.3599(4) 0.2677(2) 1.0445(2) 0.022(2) Uani ? ? N C22 0.5378(5) 0.1939(3) 1.0525(2) 0.029(2) Uani ? ? C C23 0.6989(5) 0.2480(3) 1.0122(2) 0.031(2) Uani ? ? C C24 0.6440(5) 0.2996(3) 0.9362(2) 0.028(2) Uani ? ? C N12 0.4701(4) 0.3739(2) 0.9432(2) 0.025(2) Uani ? ? N C25 0.1654(5) 0.4295(3) 0.9985(2) 0.020(2) Uani ? ? C C26 0.0810(5) 0.4751(3) 0.9314(2) 0.022(2) Uani ? ? C C27 0.0836(5) 0.4553(3) 1.0668(2) 0.021(2) Uani ? ? C O1 0.1497(4) 0.0984(3) 0.9280(2) 0.052(2) Uani ? ? O O2 0.1770(4) 0.0126(2) 1.0825(2) 0.041(2) Uani ? ? O O3 0.4885(4) 0.0720(2) 0.8430(2) 0.041(2) Uani ? ? O O4 0.0056(7) 0.2723(3) 0.8045(3) 0.106(3) Uani ? ? O H1 0.4826 0.4378 0.7343 0.0335 Uiso calc C8 H H2 0.6235 0.3409 0.7651 0.0335 Uiso calc C8 H H3 0.3470 0.2872 0.7175 0.0453 Uiso calc C9 H H4 0.5329 0.2343 0.6831 0.0453 Uiso calc C9 H H5 0.3038 0.4090 0.6143 0.0415 Uiso calc C10 H H6 0.3404 0.2948 0.5865 0.0415 Uiso calc C10 H H7 0.8699 0.6010 0.5956 0.0249 Uiso calc C12 H H8 0.8871 0.3347 0.4821 0.0230 Uiso calc C13 H H9 1.1098 0.1983 0.5915 0.0938 Uiso calc C15 H H10 1.1905 0.0770 0.5958 0.0938 Uiso calc C15 H H11 1.0126 0.1861 0.6932 0.1403 Uiso calc C16 H H12 1.1678 0.0885 0.7020 0.1403 Uiso calc C16 H H13 0.8537 0.0828 0.7584 0.0362 Uiso calc C17 H H14 0.9777 -0.0204 0.7378 0.0362 Uiso calc C17 H H15 0.6229 -0.1303 0.5943 0.0242 Uiso calc C19 H H16 0.6090 0.1721 0.4829 0.0255 Uiso calc C20 H H17 0.5231 0.1285 1.0316 0.0394 Uiso calc C22 H H18 0.5647 0.1774 1.1041 0.0394 Uiso calc C22 H H19 0.8036 0.1950 1.0074 0.0422 Uiso calc C23 H H20 0.7336 0.3024 1.0406 0.0422 Uiso calc C23 H H21 0.6217 0.2448 0.9058 0.0376 Uiso calc C24 H H22 0.7430 0.3394 0.9140 0.0376 Uiso calc C24 H H23 0.1370 0.4581 0.8847 0.0288 Uiso calc C26 H H24 0.1410 0.4250 1.1123 0.0277 Uiso calc C27 H H25 0.8202 0.4415 0.6885 0.0265 Uiso calc N7 H H26 0.5626 0.3807 0.5123 0.0281 Uiso calc N8 H H27 0.9269 0.1245 0.5104 0.0469 Uiso calc N9 H H28 0.6604 -0.0054 0.6874 0.0272 Uiso calc N10 H H29 0.2548 0.2512 1.0767 0.0291 Uiso calc N11 H H30 0.4517 0.4379 0.9090 0.0341 Uiso calc N12 H 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 _atom_site_aniso_type_symbol FE 0.0169(2) 0.0164(2) 0.0130(2) -0.0028(2) -0.0007(2) -0.0013(2) Fe C1 0.020(2) 0.030(2) 0.011(2) -0.003(2) -0.002(1) -0.000(2) C N1 0.035(2) 0.034(2) 0.026(2) -0.017(1) -0.004(1) -0.003(1) N C2 0.017(2) 0.015(2) 0.017(2) -0.000(1) -0.003(1) 0.000(1) C N2 0.024(1) 0.026(2) 0.019(1) 0.001(1) 0.000(1) -0.004(1) N C3 0.016(2) 0.018(2) 0.018(2) -0.004(1) 0.007(1) -0.004(1) C N3 0.022(2) 0.027(2) 0.025(2) 0.001(1) -0.004(1) -0.000(1) N C4 0.025(2) 0.031(2) 0.011(2) -0.002(2) 0.005(2) -0.003(2) C N4 0.040(2) 0.037(2) 0.030(2) -0.024(1) 0.006(2) -0.012(1) N C5 0.024(2) 0.019(2) 0.015(2) -0.004(2) 0.001(2) 0.001(1) C N5 0.035(2) 0.030(2) 0.025(2) -0.001(2) 0.008(2) 0.002(1) N C6 0.018(2) 0.023(2) 0.017(2) -0.005(1) 0.002(1) -0.005(1) C N6 0.034(2) 0.024(2) 0.023(2) -0.003(1) -0.003(1) -0.000(1) N C7 0.016(2) 0.014(2) 0.021(2) 0.000(1) -0.001(1) -0.004(1) C N7 0.020(1) 0.025(1) 0.018(1) -0.006(1) -0.001(1) -0.003(1) N C8 0.028(2) 0.031(2) 0.019(2) -0.008(2) 0.006(2) -0.001(2) C C9 0.035(2) 0.034(2) 0.037(2) -0.015(2) 0.013(2) -0.002(2) C C10 0.025(2) 0.048(2) 0.027(2) -0.018(2) 0.007(2) -0.013(2) C N8 0.019(1) 0.030(2) 0.018(1) -0.008(1) 0.002(1) -0.007(1) N C11 0.013(2) 0.020(2) 0.017(2) -0.004(1) -0.000(1) -0.003(1) C C12 0.017(2) 0.024(2) 0.017(2) -0.003(1) 0.002(1) -0.008(1) C C13 0.018(2) 0.019(2) 0.017(2) -0.006(1) -0.002(1) -0.004(1) C C14 0.021(2) 0.019(2) 0.023(2) -0.004(1) -0.004(2) 0.005(2) C N9 0.030(2) 0.062(2) 0.019(2) -0.029(1) -0.012(1) 0.013(2) N C15 0.056(2) 0.127(4) 0.041(3) -0.069(2) -0.023(2) 0.019(3) C C16 0.094(3) 0.213(5) 0.033(3) -0.117(3) -0.023(2) 0.018(3) C C17 0.031(2) 0.033(2) 0.021(2) -0.010(2) -0.010(2) 0.002(2) C N10 0.021(1) 0.024(1) 0.018(2) -0.007(1) -0.001(1) 0.001(1) N C18 0.015(2) 0.022(2) 0.018(2) -0.004(1) -0.001(1) 0.001(1) C C19 0.018(2) 0.019(2) 0.018(2) -0.004(1) -0.002(1) 0.003(1) C C20 0.020(2) 0.018(2) 0.020(2) -0.007(1) 0.002(2) 0.002(1) C C21 0.026(2) 0.021(2) 0.016(2) -0.004(2) -0.002(2) 0.004(2) C N11 0.022(1) 0.024(2) 0.020(2) 0.000(1) 0.002(1) 0.002(1) N C22 0.033(2) 0.026(2) 0.029(2) 0.008(2) -0.001(2) 0.001(2) C C23 0.023(2) 0.040(2) 0.033(2) 0.007(2) 0.001(2) -0.007(2) C C24 0.023(2) 0.029(2) 0.034(2) 0.001(2) 0.005(2) -0.004(2) C N12 0.026(2) 0.025(2) 0.025(2) 0.000(1) 0.004(1) 0.005(1) N C25 0.014(2) 0.023(2) 0.023(2) -0.003(1) -0.000(1) 0.001(2) C C26 0.021(2) 0.027(2) 0.018(2) -0.003(2) 0.001(2) 0.000(2) C C27 0.020(2) 0.026(2) 0.017(2) -0.003(2) -0.003(2) 0.002(2) C O1 0.047(2) 0.070(2) 0.043(2) -0.013(2) 0.007(2) -0.017(2) O O2 0.042(2) 0.044(2) 0.036(1) -0.006(1) 0.003(1) -0.011(1) O O3 0.041(2) 0.039(1) 0.043(2) -0.006(1) -0.002(1) -0.011(1) O O4 0.110(3) 0.077(3) 0.142(4) -0.012(3) -0.018(3) -0.016(3) O # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag FE C1 1.940(4) . . ? FE C2 1.938(4) . . ? FE C3 1.938(4) . . ? FE C4 1.950(4) . . ? FE C5 1.935(4) . . ? FE C6 1.935(4) . . ? C1 N1 1.155(5) . . ? C2 N2 1.152(5) . . ? C3 N3 1.163(4) . . ? C4 N4 1.158(5) . . ? C5 N5 1.158(5) . . ? C6 N6 1.154(4) . . ? C7 N7 1.309(5) . . ? C7 N8 1.320(4) . . ? C7 C11 1.479(5) . . ? N7 C8 1.457(5) . . ? C8 C9 1.498(5) . . ? C9 C10 1.499(6) . . ? C10 N8 1.471(5) . . ? C11 C12 1.411(5) . . ? C11 C13 1.391(5) . . ? C14 N9 1.316(5) . . ? C14 N10 1.315(5) . . ? C14 C18 1.481(5) . . ? N9 C15 1.461(5) . . ? C15 C16 1.335(8) . . ? C16 C17 1.444(7) . . ? C17 N10 1.467(5) . . ? C18 C19 1.376(5) . . ? C18 C20 1.394(5) . . ? C19 C20 1.383(5) . 2_656 ? C21 N11 1.306(5) . . ? C21 N12 1.314(5) . . ? C21 C25 1.480(5) . . ? N11 C22 1.486(5) . . ? C22 C23 1.506(6) . . ? C23 C24 1.492(6) . . ? C24 N12 1.475(5) . . ? C25 C26 1.404(5) . . ? C25 C27 1.394(5) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 FE C2 88.8(2) . . . ? C1 FE C3 93.2(1) . . . ? C1 FE C4 176.3(1) . . . ? C1 FE C5 90.3(2) . . . ? C1 FE C6 86.1(1) . . . ? C2 FE C3 83.6(1) . . . ? C2 FE C4 92.8(2) . . . ? C2 FE C5 175.1(1) . . . ? C2 FE C6 92.9(1) . . . ? C3 FE C4 90.2(2) . . . ? C3 FE C5 91.7(2) . . . ? C3 FE C6 176.4(2) . . . ? C4 FE C5 88.3(2) . . . ? C4 FE C6 90.6(2) . . . ? C5 FE C6 91.8(1) . . . ? FE C1 N1 177.4(3) . . . ? FE C2 N2 173.0(3) . . . ? FE C3 N3 173.6(3) . . . ? FE C4 N4 178.8(3) . . . ? FE C5 N5 178.7(3) . . . ? FE C6 N6 176.9(3) . . . ? N7 C7 N8 122.3(3) . . . ? N7 C7 C11 120.1(3) . . . ? N8 C7 C11 117.6(3) . . . ? C7 N7 C8 122.9(3) . . . ? N7 C8 C9 110.5(3) . . . ? C8 C9 C10 110.7(3) . . . ? C9 C10 N8 109.8(3) . . . ? C7 N8 C10 121.0(3) . . . ? C7 C11 C12 119.7(3) . . . ? C7 C11 C13 120.5(3) . . . ? C12 C11 C13 119.8(3) . . . ? N9 C14 N10 121.9(3) . . . ? N9 C14 C18 119.0(4) . . . ? N10 C14 C18 119.1(3) . . . ? C14 N9 C15 121.5(4) . . . ? N9 C15 C16 114.4(5) . . . ? C15 C16 C17 124.2(5) . . . ? C16 C17 N10 111.2(4) . . . ? C14 N10 C17 122.6(3) . . . ? C14 C18 C19 120.6(3) . . . ? C14 C18 C20 119.1(3) . . . ? C19 C18 C20 120.3(3) . . . ? C18 C19 C20 119.9(3) . . 2_656 ? C18 C20 C19 119.9(3) . . 2_656 ? N11 C21 N12 121.4(4) . . . ? N11 C21 C25 119.2(4) . . . ? N12 C21 C25 119.4(3) . . . ? C21 N11 C22 123.6(3) . . . ? N11 C22 C23 109.9(3) . . . ? C22 C23 C24 111.2(3) . . . ? C23 C24 N12 109.0(3) . . . ? C21 N12 C24 121.8(3) . . . ? C21 C25 C26 119.4(3) . . . ? C21 C25 C27 120.8(3) . . . ? C26 C25 C27 119.8(3) . . . ? data_st1039 _database_code_CSD 178504 #=============================================================================== _audit_creation_date 1-10-01 _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address 'Sylvie Ferlay' ; Laboratoire de Chimie de Coordination Organique Universite Louis Pasteur F-6700 Strasbourg FRANCE ; 'Olivier Felix' ; Laboratoire de Chimie de Coordination Organique Universite Louis Pasteur F-6700 Strasbourg FRANCE ; 'Mir Wais Hosseini' ; Laboratoire de Chimie de Coordination Organique Universite Louis Pasteur F-6700 Strasbourg FRANCE ; 'Jean-Marc Planeix' ; Laboratoire de Chimie de Coordination Organique Universite Louis Pasteur F-6700 Strasbourg FRANCE ; 'Nathalie Kyritsakas' ; Service Commun des Rayons X Universite Louis Pasteur F-6700 Strasbourg FRANCE ; _publ_contact_author_name 'Prof M Hosseini' _publ_contact_author_address ; Laboratoire de Chimie de Coordination Organique Universite Louis Pasteur 4 rue Blaise Pascal 67000 Strasbourg FRANCE ; _publ_contact_author_email 'HOSSEINI@CHIMIE.U-STRASBG.FR' _publ_requested_journal 'Chem Comm' _publ_section_title ; Second Sphere Supramolecular Chirality: Racemic Hybrid H-Bonded 2-D Molecular Networks ; _publ_contact_letter ; Please consider this CIF submission for publication as a new structure paper in Acta Crystallographica Section C. The figures, chemical structure diagram (scheme), Transfert of Copyright Agreement form and structure factors will be sent on receipt of your acknowledgement letter ; _publ_requested_category FM _publ_section_references ; Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. OpenMoleN, Interactive Intelligent Structure solution (1997) Nonius B.V., Delft, The Netherlands. KappaCCD Operation Manual (1997), Nonius B.V., Delft, The Nederlands. Otwinowski, Z. & Minor, W. (1997), Methods in Enzymology, 276, 307-326. Walker, N. & Stuart, D. (1983). Acta Cryst., A39, 158-166. ; #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C27 H38 Co N12 O4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C27 H38 Co N12 O4' _chemical_formula_weight 653.61 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 Co ? 0.299 0.973 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P-1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' -x,-y,-z _cell_length_a 7.1082(2) _cell_length_b 12.3899(5) _cell_length_c 17.8711(6) _cell_angle_alpha 83.424(5) _cell_angle_beta 87.389(5) _cell_angle_gamma 84.108(5) _cell_volume 1554.38(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; Cell parameters refined using Scalepack part of DENZO Z. Otwinowski, W. Minor, 1997 ; _exptl_crystal_description prism _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.40 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 686 _exptl_absorpt_coefficient_mu 0.606 _exptl_absorpt_correction_type refdelf_(Walker_&_Stuart,_1983) _exptl_absorpt_correction_T_min 0.9405 _exptl_absorpt_correction_T_max 1.0000 #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_measurement_details ; 11076 reflections were collected using program Collect ("Collect" Data collection software, Nonius B.V., 1998) The conditions were as follow : crystal to detector distance = 36. mm. Scan angle = 1.8 deg 1 scans of 60 sec per frame. Data collection was divided into 1 set(s) with the following starting angles and number of frames : Set 1 Theta = 7.80 Omega = 0.00 Kappa = 0.00 91 frames Friedel pairs were averaged. Internal R = 0.05 ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11076 _diffrn_reflns_av_R_equivalents 0.050 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 29.15 _reflns_number_total 8180 _reflns_number_gt 4180 _reflns_threshold_expression >3.0\s(I) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_OpenMoleN_(_1997) _computing_molecular_graphics ? _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 4180 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.120 _refine_ls_R_factor_gt 0.051 _refine_ls_wR_factor_all 0.405 _refine_ls_wR_factor_ref 0.075 _refine_ls_goodness_of_fit_all 7.594 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_shift/su_max 0.011 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.656 _refine_diff_density_min -0.180 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol Co 0.23424(7) 0.71034(5) 0.72884(3) 0.0154(2) Uani ? ? Co C1 0.1020(5) 0.5845(4) 0.7304(2) 0.018(2) Uani ? ? C N1 0.0276(5) 0.5046(3) 0.7344(2) 0.030(2) Uani ? ? N C2 0.3955(5) 0.6613(3) 0.6496(2) 0.017(2) Uani ? ? C N2 0.4778(5) 0.6352(3) 0.5961(2) 0.022(2) Uani ? ? N C3 0.0874(5) 0.7862(3) 0.6497(2) 0.018(2) Uani ? ? C N3 0.0123(5) 0.8306(3) 0.5972(2) 0.022(2) Uani ? ? N C4 0.3709(6) 0.8333(4) 0.7331(2) 0.020(2) Uani ? ? C N4 0.4520(5) 0.9084(3) 0.7372(2) 0.032(2) Uani ? ? N C5 0.0615(6) 0.7633(3) 0.8024(2) 0.020(2) Uani ? ? C N5 -0.0461(5) 0.7971(3) 0.8472(2) 0.029(2) Uani ? ? N C6 0.3901(5) 0.6297(3) 0.8030(2) 0.018(2) Uani ? ? C N6 0.4797(5) 0.5758(3) 0.8484(2) 0.027(2) Uani ? ? N C7 0.7001(5) 0.4193(3) 0.5961(2) 0.018(2) Uani ? ? C N7 0.7100(5) 0.4172(3) 0.6691(2) 0.020(2) Uani ? ? N C8 0.5629(6) 0.3766(4) 0.7217(2) 0.023(2) Uani ? ? C C9 0.4533(7) 0.2995(4) 0.6867(3) 0.035(2) Uani ? ? C C10 0.3937(6) 0.3479(4) 0.6092(2) 0.032(2) Uani ? ? C N8 0.5576(5) 0.3829(3) 0.5650(2) 0.023(2) Uani ? ? N C11 0.8546(5) 0.4617(3) 0.5461(2) 0.017(2) Uani ? ? C C12 0.9208(5) 0.5605(4) 0.5564(2) 0.019(2) Uani ? ? C C13 0.9333(6) 0.4017(3) 0.4890(2) 0.019(2) Uani ? ? C C14 0.7853(6) 0.0527(4) 0.5943(2) 0.021(2) Uani ? ? C N9 0.9257(5) 0.1029(4) 0.5631(2) 0.033(2) Uani ? ? N C15 1.0818(8) 0.1268(6) 0.6062(3) 0.067(3) Uani ? ? C C16 1.0545(9) 0.1084(8) 0.6793(3) 0.096(4) Uani ? ? C C17 0.9136(6) 0.0472(4) 0.7188(2) 0.029(2) Uani ? ? C N10 0.7693(5) 0.0264(3) 0.6675(2) 0.022(2) Uani ? ? N C18 0.6363(5) 0.0244(4) 0.5458(2) 0.019(2) Uani ? ? C C19 0.5735(5) -0.0774(3) 0.5553(2) 0.018(2) Uani ? ? C C20 0.5637(6) 0.1030(3) 0.4901(2) 0.019(2) Uani ? ? C C21 0.3402(5) 0.3543(4) 0.9952(2) 0.019(2) Uani ? ? C N11 0.3617(5) 0.2681(3) 1.0451(2) 0.023(2) Uani ? ? N C22 0.5376(6) 0.1941(4) 1.0526(2) 0.028(2) Uani ? ? C C23 0.6998(6) 0.2496(4) 1.0119(3) 0.032(2) Uani ? ? C C24 0.6435(6) 0.3001(4) 0.9350(2) 0.029(2) Uani ? ? C N12 0.4704(5) 0.3742(3) 0.9424(2) 0.025(2) Uani ? ? N C25 0.1656(6) 0.4295(4) 0.9981(2) 0.020(2) Uani ? ? C C26 0.0793(6) 0.4736(4) 0.9308(2) 0.022(2) Uani ? ? C C27 0.0858(6) 0.4565(4) 1.0672(2) 0.020(2) Uani ? ? C O1 0.1500(5) 0.0999(3) 0.9271(2) 0.051(2) Uani ? ? O O2 0.1753(5) 0.0147(3) 1.0826(2) 0.041(2) Uani ? ? O O3 0.4898(5) 0.0696(3) 0.8419(2) 0.040(2) Uani ? ? O O4 0.0093(9) 0.2734(5) 0.8015(4) 0.112(4) Uani ? ? O H1 0.4790 0.4366 0.7351 0.0309 Uiso calc C8 H H2 0.6204 0.3395 0.7656 0.0309 Uiso calc C8 H H3 0.3439 0.2858 0.7175 0.0457 Uiso calc C9 H H4 0.5304 0.2329 0.6829 0.0457 Uiso calc C9 H H5 0.3028 0.4089 0.6134 0.0430 Uiso calc C10 H H6 0.3396 0.2946 0.5851 0.0430 Uiso calc C10 H H7 0.8653 0.6018 0.5948 0.0249 Uiso calc C12 H H8 0.8862 0.3348 0.4815 0.0245 Uiso calc C13 H H9 1.1009 0.2016 0.5939 0.0980 Uiso calc C15 H H10 1.1921 0.0826 0.5921 0.0980 Uiso calc C15 H H11 1.0331 0.1788 0.6960 0.1608 Uiso calc C16 H H12 1.1717 0.0735 0.6972 0.1608 Uiso calc C16 H H13 0.8548 0.0872 0.7572 0.0383 Uiso calc C17 H H14 0.9723 -0.0206 0.7409 0.0383 Uiso calc C17 H H15 0.6248 -0.1308 0.5933 0.0238 Uiso calc C19 H H16 0.6080 0.1734 0.4834 0.0257 Uiso calc C20 H H17 0.5226 0.1291 1.0310 0.0390 Uiso calc C22 H H18 0.5644 0.1768 1.1044 0.0390 Uiso calc C22 H H19 0.8057 0.1971 1.0073 0.0428 Uiso calc C23 H H20 0.7329 0.3049 1.0402 0.0428 Uiso calc C23 H H21 0.6207 0.2445 0.9050 0.0382 Uiso calc C24 H H22 0.7420 0.3399 0.9118 0.0382 Uiso calc C24 H H23 0.1340 0.4556 0.8837 0.0303 Uiso calc C26 H H24 0.1447 0.4270 1.1127 0.0269 Uiso calc C27 H H25 0.8168 0.4430 0.6887 0.0266 Uiso calc N7 H H26 0.5623 0.3794 0.5122 0.0290 Uiso calc N8 H H27 0.9262 0.1246 0.5103 0.0465 Uiso calc N9 H H28 0.6609 -0.0070 0.6878 0.0285 Uiso calc N10 H H29 0.2576 0.2524 1.0785 0.0311 Uiso calc N11 H H30 0.4520 0.4383 0.9079 0.0342 Uiso calc N12 H 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 _atom_site_aniso_type_symbol Co 0.0158(2) 0.0174(2) 0.0133(2) -0.0035(2) 0.0002(2) -0.0012(2) Co C1 0.019(2) 0.029(2) 0.010(2) -0.003(2) -0.001(2) -0.001(2) C N1 0.037(2) 0.030(2) 0.024(2) -0.016(2) -0.005(2) 0.001(2) N C2 0.018(2) 0.014(2) 0.019(2) -0.005(2) -0.005(2) 0.002(2) C N2 0.025(2) 0.026(2) 0.017(2) -0.001(2) 0.002(1) -0.002(2) N C3 0.017(2) 0.017(2) 0.021(2) -0.006(2) 0.005(2) -0.004(2) C N3 0.023(2) 0.024(2) 0.020(2) -0.001(2) -0.003(1) -0.001(1) N C4 0.022(2) 0.027(2) 0.013(2) -0.006(2) 0.001(2) -0.005(2) C N4 0.039(2) 0.040(2) 0.021(2) -0.021(2) 0.003(2) -0.010(2) N C5 0.021(2) 0.021(2) 0.018(2) -0.005(2) 0.002(2) 0.001(2) C N5 0.029(2) 0.031(2) 0.028(2) -0.003(2) 0.006(2) 0.001(2) N C6 0.017(2) 0.024(2) 0.016(2) -0.004(2) 0.003(2) -0.005(2) C N6 0.029(2) 0.030(2) 0.022(2) -0.005(2) -0.003(1) -0.001(2) N C7 0.018(2) 0.019(2) 0.017(2) -0.000(2) -0.000(2) -0.003(2) C N7 0.020(2) 0.027(2) 0.015(2) -0.008(1) 0.000(1) -0.002(1) N C8 0.027(2) 0.029(2) 0.016(2) -0.010(2) 0.006(2) -0.001(2) C C9 0.034(2) 0.039(3) 0.033(2) -0.016(2) 0.012(2) -0.003(2) C C10 0.026(2) 0.052(3) 0.025(2) -0.023(2) 0.004(2) -0.007(2) C N8 0.021(2) 0.030(2) 0.019(2) -0.012(1) 0.003(1) -0.005(1) N C11 0.015(2) 0.020(2) 0.015(2) -0.004(2) -0.000(1) -0.002(2) C C12 0.019(2) 0.025(2) 0.014(2) -0.002(2) -0.000(2) -0.005(2) C C13 0.022(2) 0.020(2) 0.017(2) -0.006(2) -0.002(2) -0.004(2) C C14 0.023(2) 0.023(2) 0.018(2) -0.007(2) -0.005(2) 0.003(2) C N9 0.028(2) 0.059(3) 0.022(2) -0.028(2) -0.008(2) 0.011(2) N C15 0.059(3) 0.137(5) 0.038(3) -0.071(3) -0.021(2) 0.020(3) C C16 0.104(3) 0.250(7) 0.034(3) -0.137(3) -0.029(3) 0.028(4) C C17 0.033(2) 0.035(3) 0.022(2) -0.012(2) -0.011(2) 0.001(2) C N10 0.021(2) 0.025(2) 0.021(2) -0.007(1) -0.003(1) -0.001(2) N C18 0.014(2) 0.026(2) 0.019(2) -0.006(2) -0.001(2) -0.002(2) C C19 0.016(2) 0.022(2) 0.016(2) -0.002(2) -0.002(2) 0.003(2) C C20 0.021(2) 0.013(2) 0.025(2) -0.006(2) 0.002(2) 0.002(2) C C21 0.020(2) 0.025(2) 0.015(2) -0.004(2) -0.004(2) 0.003(2) C N11 0.022(2) 0.025(2) 0.023(2) 0.001(2) 0.001(1) 0.002(2) N C22 0.032(2) 0.034(3) 0.021(2) 0.008(2) 0.000(2) 0.000(2) C C23 0.023(2) 0.037(3) 0.038(3) 0.005(2) 0.001(2) -0.005(2) C C24 0.025(2) 0.036(3) 0.027(2) -0.002(2) 0.005(2) -0.005(2) C N12 0.022(2) 0.026(2) 0.028(2) 0.004(2) 0.004(1) 0.002(2) N C25 0.017(2) 0.023(2) 0.020(2) -0.005(2) -0.001(2) 0.001(2) C C26 0.021(2) 0.033(2) 0.016(2) -0.006(2) 0.001(2) 0.001(2) C C27 0.021(2) 0.024(2) 0.016(2) -0.002(2) -0.005(2) 0.002(2) C O1 0.048(2) 0.070(3) 0.040(2) -0.012(2) 0.005(2) -0.015(2) O O2 0.041(2) 0.041(2) 0.041(2) -0.004(2) 0.003(2) -0.014(2) O O3 0.035(2) 0.041(2) 0.044(2) -0.009(2) 0.000(2) -0.009(2) O O4 0.102(4) 0.079(4) 0.174(5) -0.010(4) -0.008(4) -0.013(4) O # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co C1 1.899(5) . . ? Co C2 1.896(4) . . ? Co C3 1.897(4) . . ? Co C4 1.900(5) . . ? Co C5 1.884(4) . . ? Co C6 1.894(4) . . ? C1 N1 1.162(6) . . ? C2 N2 1.158(5) . . ? C3 N3 1.156(5) . . ? C4 N4 1.154(6) . . ? C5 N5 1.165(5) . . ? C6 N6 1.160(5) . . ? C7 N7 1.307(5) . . ? C7 N8 1.319(5) . . ? C7 C11 1.484(6) . . ? N7 C8 1.462(5) . . ? C8 C9 1.498(7) . . ? C9 C10 1.506(7) . . ? C10 N8 1.453(5) . . ? C11 C12 1.390(6) . . ? C11 C13 1.394(6) . . ? C14 N9 1.300(6) . . ? C14 N10 1.313(5) . . ? C14 C18 1.492(6) . . ? N9 C15 1.453(6) . . ? C15 C16 1.309(8) . . ? C16 C17 1.431(8) . . ? C17 N10 1.468(5) . . ? C18 C19 1.370(6) . . ? C18 C20 1.388(6) . . ? C19 C20 1.380(6) . 2_656 ? C21 N11 1.313(5) . . ? C21 N12 1.312(5) . . ? C21 C25 1.476(6) . . ? N11 C22 1.474(6) . . ? C22 C23 1.517(7) . . ? C23 C24 1.498(6) . . ? C24 N12 1.468(6) . . ? C25 C26 1.404(6) . . ? C25 C27 1.396(6) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Co C2 89.7(2) . . . ? C1 Co C3 92.1(2) . . . ? C1 Co C4 176.6(2) . . . ? C1 Co C5 89.8(2) . . . ? C1 Co C6 87.2(2) . . . ? C2 Co C3 84.4(2) . . . ? C2 Co C4 91.8(2) . . . ? C2 Co C5 175.9(2) . . . ? C2 Co C6 91.9(2) . . . ? C3 Co C4 91.0(2) . . . ? C3 Co C5 91.6(2) . . . ? C3 Co C6 176.3(2) . . . ? C4 Co C5 88.9(2) . . . ? C4 Co C6 89.8(2) . . . ? C5 Co C6 92.1(2) . . . ? Co C1 N1 176.3(4) . . . ? Co C2 N2 172.6(4) . . . ? Co C3 N3 173.7(4) . . . ? Co C4 N4 178.5(4) . . . ? Co C5 N5 179.1(4) . . . ? Co C6 N6 176.4(4) . . . ? N7 C7 N8 121.9(4) . . . ? N7 C7 C11 119.6(4) . . . ? N8 C7 C11 118.5(4) . . . ? C7 N7 C8 122.5(4) . . . ? N7 C8 C9 110.8(4) . . . ? C8 C9 C10 110.4(4) . . . ? C9 C10 N8 109.5(4) . . . ? C7 N8 C10 122.1(4) . . . ? C7 C11 C12 120.2(4) . . . ? C7 C11 C13 119.6(4) . . . ? C12 C11 C13 120.3(4) . . . ? N9 C14 N10 122.2(4) . . . ? N9 C14 C18 119.2(4) . . . ? N10 C14 C18 118.6(4) . . . ? C14 N9 C15 122.2(4) . . . ? N9 C15 C16 114.1(5) . . . ? C15 C16 C17 127.1(6) . . . ? C16 C17 N10 110.9(4) . . . ? C14 N10 C17 122.0(4) . . . ? C14 C18 C19 120.9(4) . . . ? C14 C18 C20 118.6(4) . . . ? C19 C18 C20 120.5(4) . . . ? C18 C19 C20 120.5(4) . . 2_656 ? C18 C20 C19 119.1(4) . . 2_656 ? N11 C21 N12 121.1(4) . . . ? N11 C21 C25 119.3(4) . . . ? N12 C21 C25 119.6(4) . . . ? C21 N11 C22 123.9(4) . . . ? N11 C22 C23 109.5(4) . . . ? C22 C23 C24 110.4(4) . . . ? C23 C24 N12 108.8(4) . . . ? C21 N12 C24 121.9(4) . . . ? C21 C25 C26 119.5(4) . . . ? C21 C25 C27 120.5(4) . . . ? C26 C25 C27 120.0(4) . . . ?