Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _audit_creation_date 31-08-00 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Siri, Olivier' 'Braunstein, P.' _publ_contact_author_name 'Prof P Braunstein' _publ_contact_author_address ; Laboratoire de Chimie de Coordn. UMR 7513 CNRS Universite Louis Pasteur 4 rue Blaise Pascal Strasbourg cedex 67070 FRANCE ; _publ_contact_author_phone '+33/(0)3-90-24-13-08' _publ_contact_author_fax '+33/(0)3-90-24-13-22' _publ_contact_author_email 'braunst@chimie.u-strasbg.fr' _publ_section_title ; Novel Access to N,N,O,O-Quinonoid Systems and Switching off Aromatic Delocalization in a New Zwitterionic Supramolecular Wire ; data_4 (CCDC number 149251) _database_code_CSD 149251 #=========================================================================== _audit_creation_date 18-10-01 # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 4' _chemical_formula_moiety 'C26 H40 N2 O6' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C26 H40 N2 O6' _chemical_formula_weight 476.62 _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 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 10.3719(6) _cell_length_b 11.2034(6) _cell_length_c 13.8449(8) _cell_angle_alpha 103.748(5) _cell_angle_beta 103.919(5) _cell_angle_gamma 112.113(5) _cell_volume 1346.9(1) _cell_formula_units_Z 2 _cell_measurement_temperature 294 _cell_measurement_reflns_used 9559 _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 prism _exptl_crystal_colour 'brown' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.18 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=========================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 294 _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 ; 9559 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 30 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 == -172.00 Phi == 0.00 21 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 9559 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 27.43 _reflns_number_total 6129 _reflns_number_gt 2192 _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 2192 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_number_constraints 18 _refine_ls_R_factor_all 0.191 _refine_ls_R_factor_gt 0.068 _refine_ls_wR_factor_all 0.405 _refine_ls_wR_factor_ref 0.081 _refine_ls_goodness_of_fit_all 6.816 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_shift/su_max 0.001 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.578 _refine_diff_density_min -0.145 #=========================================================================== # 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 O1 0.9939(4) 0.1578(3) 0.8354(3) 0.087(2) Uani ? ? O O2 1.0568(3) 0.4160(3) 1.2295(2) 0.036(2) Uani ? ? O O3 0.6724(3) 0.3322(3) 0.7566(2) 0.035(2) Uani ? ? O O4 0.5034(5) 0.1083(4) 0.6777(3) 0.056(2) Uani ? ? O O5 0.5797(3) 0.2700(4) 1.0694(2) 0.037(2) Uani ? ? O O6 0.3974(4) 0.0658(4) 0.9535(3) 0.064(2) Uani ? ? O C1 0.8936(5) 0.2938(4) 0.9858(4) 0.028(2) Uani ? ? C C2 0.8536(5) 0.3151(4) 0.8908(3) 0.030(2) Uani ? ? C C3 0.7153(5) 0.3132(5) 0.8533(3) 0.029(2) Uani ? ? C C4 0.6240(5) 0.2978(5) 0.9115(4) 0.033(2) Uani ? ? C C5 0.6664(5) 0.2760(5) 1.0051(4) 0.030(2) Uani ? ? C C6 0.7989(5) 0.2706(4) 1.0422(3) 0.026(2) Uani ? ? C C7 1.0091(5) 0.2535(5) 0.8040(4) 0.040(2) Uani ? ? C C8 1.1077(5) 0.2859(4) 0.7374(4) 0.034(2) Uani ? ? C C9 1.1309(5) 0.4160(5) 0.7136(4) 0.043(2) Uani ? ? C C10 1.2568(6) 0.2962(6) 0.7979(5) 0.065(3) Uani ? ? C C11 1.0292(6) 0.1601(5) 0.6324(4) 0.055(3) Uani ? ? C C12 0.9562(5) 0.3070(4) 1.2206(4) 0.032(2) Uani ? ? C C13 0.9661(4) 0.2491(3) 1.3099(2) 0.032(2) Uani ? ? C C14 1.1073 0.2271 1.3323 0.174(4) Uani ? ? C C15 0.9800 0.3596 1.4086 0.119(4) Uani ? ? C C16 0.8287 0.1096 1.2846 0.095(4) Uani ? ? C C17 0.5631(5) 0.2188(5) 0.6705(4) 0.037(2) Uani ? ? C C18 0.5282(5) 0.2515(5) 0.5703(4) 0.034(2) Uani ? ? C C19 0.5115(7) 0.3844(5) 0.5945(4) 0.062(3) Uani ? ? C C20 0.6565(6) 0.2695(6) 0.5303(4) 0.058(3) Uani ? ? C C21 0.3842(6) 0.1315(6) 0.4866(4) 0.049(3) Uani ? ? C C22 0.4429(6) 0.1627(6) 1.0352(4) 0.046(3) Uani ? ? C C23 0.3594(3) 0.1842(4) 1.1073(3) 0.044(3) Uani ? ? C C24 0.1932 0.0763 1.0492 0.069(4) Uani ? ? C C25 0.3713 0.3310 1.1329 0.141(5) Uani ? ? C C26 0.4305 0.1631 1.2088 0.221(5) Uani ? ? C N1 0.9477(4) 0.3366(4) 0.8309(3) 0.035(2) Uani ? ? N N2 0.8300(4) 0.2336(4) 1.1334(3) 0.030(2) Uani ? ? N H1 0.9877 0.2952 1.0127 0.0383 Uiso calc C1 H H2 0.5326 0.3022 0.8874 0.0462 Uiso calc C4 H H3 0.9684 0.4135 0.8086 0.0391 Uiso calc N1 H H4 0.7561 0.1509 1.1326 0.0425 Uiso calc N2 H H5 1.1927 0.4289 0.6723 0.0489 Uiso calc C9 H H6 1.0369 0.4075 0.6747 0.0489 Uiso calc C9 H H7 1.1777 0.4934 0.7788 0.0489 Uiso calc C9 H H8 1.3211 0.3163 0.7590 0.0772 Uiso calc C10 H H9 1.3013 0.3680 0.8662 0.0772 Uiso calc C10 H H10 1.2414 0.2108 0.8065 0.0772 Uiso calc C10 H H11 1.0857 0.1746 0.5877 0.0712 Uiso calc C11 H H12 1.0212 0.0797 0.6473 0.0712 Uiso calc C11 H H13 0.9320 0.1482 0.5971 0.0712 Uiso calc C11 H H14 1.1154 0.1910 1.3878 0.1717 Uiso calc C14 H H15 1.0998 0.1637 1.2693 0.1717 Uiso calc C14 H H16 1.1934 0.3130 1.3535 0.1717 Uiso calc C14 H H17 0.9866 0.3283 1.4668 0.1755 Uiso calc C15 H H18 1.0674 0.4436 1.4275 0.1755 Uiso calc C15 H H19 0.8945 0.3749 1.3923 0.1755 Uiso calc C15 H H20 0.8432 0.0804 1.3436 0.1309 Uiso calc C16 H H21 0.7410 0.1216 1.2716 0.1309 Uiso calc C16 H H22 0.8181 0.0416 1.2230 0.1309 Uiso calc C16 H H23 0.4896 0.4037 0.5310 0.0764 Uiso calc C19 H H24 0.4324 0.3728 0.6204 0.0764 Uiso calc C19 H H25 0.6021 0.4590 0.6470 0.0764 Uiso calc C19 H H26 0.6369 0.2901 0.4673 0.0744 Uiso calc C20 H H27 0.7471 0.3431 0.5838 0.0744 Uiso calc C20 H H28 0.6656 0.1863 0.5150 0.0744 Uiso calc C20 H H29 0.3612 0.1510 0.4233 0.0716 Uiso calc C21 H H30 0.3960 0.0498 0.4712 0.0716 Uiso calc C21 H H31 0.3052 0.1186 0.5128 0.0716 Uiso calc C21 H H32 0.1391 0.0887 1.0939 0.0950 Uiso calc C24 H H33 0.1533 0.0879 0.9847 0.0950 Uiso calc C24 H H34 0.1849 -0.0142 1.0331 0.0950 Uiso calc C24 H H35 0.3183 0.3435 1.1785 0.2171 Uiso calc C25 H H36 0.4735 0.3981 1.1676 0.2171 Uiso calc C25 H H37 0.3295 0.3416 1.0684 0.2171 Uiso calc C25 H H38 0.3811 0.1757 1.2570 0.3334 Uiso calc C26 H H39 0.4208 0.0720 1.1903 0.3334 Uiso calc C26 H H40 0.5335 0.2284 1.2418 0.3334 Uiso calc C26 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 O1 0.107(2) 0.066(2) 0.093(2) 0.063(1) 0.077(1) 0.061(1) O O2 0.037(2) 0.039(2) 0.032(2) 0.009(1) 0.008(1) 0.017(1) O O3 0.030(1) 0.047(2) 0.031(2) 0.012(1) 0.007(1) 0.022(1) O O4 0.110(3) 0.043(2) 0.038(2) 0.007(2) 0.007(2) 0.018(2) O O5 0.027(1) 0.069(2) 0.028(2) 0.005(1) 0.014(1) 0.012(2) O O6 0.063(2) 0.063(2) 0.066(2) 0.007(2) 0.041(2) 0.011(2) O C1 0.026(2) 0.031(2) 0.028(2) 0.009(2) 0.010(2) 0.013(2) C C2 0.030(2) 0.032(2) 0.028(2) 0.011(2) 0.016(2) 0.013(2) C C3 0.031(2) 0.039(2) 0.021(2) 0.013(2) 0.007(2) 0.016(2) C C4 0.024(2) 0.050(2) 0.030(2) 0.014(2) 0.009(2) 0.015(2) C C5 0.023(2) 0.045(2) 0.026(2) 0.010(2) 0.014(2) 0.013(2) C C6 0.028(2) 0.028(2) 0.024(2) 0.006(2) 0.011(2) 0.010(2) C C7 0.043(2) 0.039(2) 0.039(2) 0.023(2) 0.023(2) 0.024(2) C C8 0.032(2) 0.036(2) 0.033(2) 0.018(2) 0.018(2) 0.018(2) C C9 0.044(2) 0.046(2) 0.040(2) 0.024(2) 0.027(2) 0.025(2) C C10 0.049(3) 0.089(3) 0.062(3) 0.042(2) 0.024(2) 0.043(2) C C11 0.072(3) 0.049(3) 0.048(3) 0.025(2) 0.031(2) 0.019(2) C C12 0.033(2) 0.035(2) 0.029(2) 0.018(2) 0.016(2) 0.012(2) C C13 0.041(2) 0.037(2) 0.022(2) 0.021(2) 0.016(2) 0.016(2) C C14 0.119(4) 0.251(4) 0.177(4) 0.137(3) 0.106(3) 0.185(3) C C15 0.316(8) 0.098(3) 0.054(3) 0.121(4) 0.098(4) 0.057(3) C C16 0.095(5) 0.104(4) 0.086(4) 0.012(4) 0.021(4) 0.076(3) C C17 0.039(2) 0.042(2) 0.031(2) 0.019(2) 0.011(2) 0.013(2) C C18 0.035(2) 0.044(2) 0.026(2) 0.019(2) 0.008(2) 0.016(2) C C19 0.080(3) 0.066(3) 0.046(3) 0.044(2) 0.019(3) 0.032(2) C C20 0.051(3) 0.087(3) 0.045(3) 0.031(2) 0.026(2) 0.035(2) C C21 0.046(3) 0.064(3) 0.040(3) 0.019(2) 0.003(2) 0.018(2) C C22 0.041(2) 0.067(3) 0.036(2) 0.019(2) 0.016(2) 0.025(2) C C23 0.028(2) 0.089(4) 0.034(2) 0.013(2) 0.020(2) 0.018(3) C C24 0.053(3) 0.069(4) 0.092(4) 0.019(3) 0.043(2) 0.017(3) C C25 0.154(4) 0.079(5) 0.230(6) 0.009(4) 0.162(3) -0.023(5) C C26 0.129(4) 0.68(1) 0.124(4) 0.236(5) 0.110(3) 0.259(5) C N1 0.035(2) 0.035(2) 0.035(2) 0.019(1) 0.023(1) 0.024(1) N N2 0.032(2) 0.036(2) 0.024(2) 0.005(2) 0.011(1) 0.017(1) N # 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 O1 C7 1.220(7) . . ? O2 C12 1.226(5) . . ? O3 C3 1.399(6) . . ? O3 C17 1.365(4) . . ? O4 C17 1.199(7) . . ? O5 C5 1.405(7) . . ? O5 C22 1.344(5) . . ? O6 C22 1.206(6) . . ? C1 C2 1.385(7) . . ? C1 C6 1.384(8) . . ? C2 C3 1.393(7) . . ? C2 N1 1.416(7) . . ? C3 C4 1.374(8) . . ? C4 C5 1.374(8) . . ? C5 C6 1.376(7) . . ? C6 N2 1.423(7) . . ? C7 C8 1.537(8) . . ? C7 N1 1.345(7) . . ? C8 C9 1.515(8) . . ? C8 C10 1.517(8) . . ? C8 C11 1.534(6) . . ? C12 C13 1.526(7) . . ? C12 N2 1.344(5) . . ? C13 C14 1.546(4) . . ? C13 C15 1.545(3) . . ? C13 C16 1.555(3) . . ? C17 C18 1.513(8) . . ? C18 C19 1.530(9) . . ? C18 C20 1.525(9) . . ? C18 C21 1.515(5) . . ? C22 C23 1.504(8) . . ? C23 C24 1.544(3) . . ? C23 C25 1.547(5) . . ? C23 C26 1.538(4) . . ? 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 C3 O3 C17 117.1(4) . . . ? C5 O5 C22 119.9(4) . . . ? C2 C1 C6 121.1(5) . . . ? C1 C2 C3 118.3(5) . . . ? C1 C2 N1 122.0(5) . . . ? C3 C2 N1 119.6(4) . . . ? O3 C3 C2 118.9(5) . . . ? O3 C3 C4 120.1(5) . . . ? C2 C3 C4 121.0(5) . . . ? C3 C4 C5 119.2(5) . . . ? O5 C5 C4 119.9(5) . . . ? O5 C5 C6 118.5(5) . . . ? C4 C5 C6 121.4(5) . . . ? C1 C6 C5 118.7(5) . . . ? C1 C6 N2 122.1(5) . . . ? C5 C6 N2 119.0(5) . . . ? O1 C7 C8 119.8(5) . . . ? O1 C7 N1 121.5(5) . . . ? C8 C7 N1 118.6(5) . . . ? C7 C8 C9 114.6(5) . . . ? C7 C8 C10 107.0(5) . . . ? C7 C8 C11 105.8(4) . . . ? C9 C8 C10 110.4(4) . . . ? C9 C8 C11 109.7(4) . . . ? C10 C8 C11 109.1(5) . . . ? O2 C12 C13 121.6(3) . . . ? O2 C12 N2 122.2(5) . . . ? C13 C12 N2 116.3(4) . . . ? C12 C13 C14 108.2(3) . . . ? C12 C13 C15 106.2(3) . . . ? C12 C13 C16 114.5(2) . . . ? C14 C13 C15 110.7(2) . . . ? C14 C13 C16 108.3(2) . . . ? C15 C13 C16 108.9(2) . . . ? O3 C17 O4 121.7(5) . . . ? O3 C17 C18 112.3(4) . . . ? O4 C17 C18 125.9(4) . . . ? C17 C18 C19 110.3(4) . . . ? C17 C18 C20 108.0(5) . . . ? C17 C18 C21 108.8(4) . . . ? C19 C18 C20 110.0(5) . . . ? C19 C18 C21 110.0(5) . . . ? C20 C18 C21 109.7(4) . . . ? O5 C22 O6 120.9(6) . . . ? O5 C22 C23 112.0(4) . . . ? O6 C22 C23 127.1(4) . . . ? C22 C23 C24 108.5(2) . . . ? C22 C23 C25 110.2(4) . . . ? C22 C23 C26 106.5(4) . . . ? C24 C23 C25 109.0(3) . . . ? C24 C23 C26 111.0(3) . . . ? C25 C23 C26 111.7(2) . . . ? C2 N1 C7 123.2(4) . . . ? C6 N2 C12 124.9(4) . . . ? #=========================================================================== data_st680 (CCDC number 149252) _database_code_CSD 149252 #=========================================================================== _audit_creation_date 31-08-00 #=========================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 6' _chemical_formula_moiety 'C16 H26 N2 O2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H26 N2 O2' _chemical_formula_weight 278.40 _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 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 monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' -x,1/2+y,1/2-z -x,-y,-z +x,1/2-y,1/2+z _cell_length_a 12.9221(7) _cell_length_b 19.696(1) _cell_length_c 13.3065(8) _cell_angle_alpha 90 _cell_angle_beta 101.231(5) _cell_angle_gamma 90 _cell_volume 3321.9(7) _cell_formula_units_Z 8 _cell_measurement_temperature 294 _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 'purple' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.11 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=========================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 294 _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 ; 13557 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 40 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 == 0.00 107 frames Set 2 Theta == -6.30 Kappa == -172.00 Phi == 0.00 28 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 13557 _diffrn_reflns_av_R_equivalents 0.050 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 27.47 _reflns_number_total 7807 _reflns_number_gt 1891 _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 1891 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.231 _refine_ls_R_factor_gt 0.039 _refine_ls_wR_factor_all 0.259 _refine_ls_wR_factor_ref 0.041 _refine_ls_goodness_of_fit_all 8.600 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_shift/su_max 0.004 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.126 _refine_diff_density_min -0.162 #=========================================================================== # 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 C1 0.9333(2) 0.2397(2) 0.7653(2) 0.029(2) Uani ? ? C C2 0.8561(2) 0.1934(2) 0.7243(2) 0.027(2) Uani ? ? C C3 0.8522(2) 0.1620(2) 0.6187(2) 0.032(2) Uani ? ? C C4 0.9278(3) 0.1828(2) 0.5641(3) 0.037(2) Uani ? ? C C5 1.0039(2) 0.2318(2) 0.5999(3) 0.036(2) Uani ? ? C C6 1.0057(2) 0.2601(2) 0.7079(2) 0.031(2) Uani ? ? C N1 0.7789(2) 0.1721(1) 0.7672(2) 0.034(2) Uani ? ? N C7 0.7519(2) 0.1919(2) 0.8639(3) 0.037(2) Uani ? ? C C8 0.7628(3) 0.1354(2) 0.9425(3) 0.037(2) Uani ? ? C C9 0.8780(3) 0.1122(2) 0.9685(3) 0.056(3) Uani ? ? C C10 0.6925(3) 0.0753(2) 0.9032(3) 0.047(2) Uani ? ? C C11 0.7296(3) 0.1642(2) 1.0380(3) 0.066(3) Uani ? ? C N2 1.0832(2) 0.3042(1) 0.7361(2) 0.034(2) Uani ? ? N C12 1.1102(2) 0.3411(2) 0.8325(3) 0.035(2) Uani ? ? C C13 1.0763(3) 0.4155(2) 0.8261(3) 0.039(2) Uani ? ? C C14 0.9571(3) 0.4214(2) 0.8013(3) 0.055(3) Uani ? ? C C15 1.1193(3) 0.4467(2) 0.9314(3) 0.062(3) Uani ? ? C C16 1.1219(3) 0.4521(2) 0.7444(3) 0.066(3) Uani ? ? C O1 0.7799(2) 0.1196(1) 0.5885(2) 0.044(2) Uani ? ? O O2 1.0697(2) 0.2556(1) 0.5517(2) 0.047(2) Uani ? ? O C17 1.4103(2) 0.2224(2) 0.4774(2) 0.031(2) Uani ? ? C C18 1.3442(2) 0.2563(2) 0.5312(3) 0.030(2) Uani ? ? C C19 1.3595(2) 0.2519(2) 0.6483(2) 0.034(2) Uani ? ? C C20 1.4380(2) 0.2090(2) 0.6970(3) 0.036(2) Uani ? ? C C21 1.5025(2) 0.1722(2) 0.6450(3) 0.032(2) Uani ? ? C C22 1.4895(2) 0.1827(2) 0.5302(3) 0.030(2) Uani ? ? C N3 1.2639(2) 0.2952(1) 0.4915(2) 0.033(2) Uani ? ? N C23 1.2272(2) 0.3138(2) 0.3851(3) 0.035(2) Uani ? ? C C24 1.2359(2) 0.3895(2) 0.3642(3) 0.032(2) Uani ? ? C C25 1.2015(3) 0.3997(2) 0.2488(3) 0.055(3) Uani ? ? C C26 1.3494(3) 0.4136(2) 0.3989(3) 0.058(3) Uani ? ? C C27 1.1634(3) 0.4293(2) 0.4202(3) 0.062(3) Uani ? ? C N4 1.5614(2) 0.1501(1) 0.4905(2) 0.037(2) Uani ? ? N C28 1.5736(3) 0.1482(2) 0.3841(3) 0.043(2) Uani ? ? C C29 1.5421(3) 0.0805(2) 0.3315(3) 0.041(2) Uani ? ? C C30 1.5579(4) 0.0868(2) 0.2213(3) 0.078(3) Uani ? ? C C31 1.6091(3) 0.0231(2) 0.3856(3) 0.063(3) Uani ? ? C C32 1.4261(3) 0.0665(2) 0.3312(3) 0.067(3) Uani ? ? C O3 1.2992(2) 0.2873(1) 0.6907(2) 0.045(2) Uani ? ? O O4 1.5712(2) 0.1295(1) 0.6847(2) 0.042(2) Uani ? ? O H1 0.6807 0.2071 0.8508 0.0470 Uiso calc C7 H H2 0.7970 0.2281 0.8918 0.0470 Uiso calc C7 H H3 0.8850 0.0767 1.0178 0.0749 Uiso calc C9 H H4 0.8989 0.0960 0.9081 0.0749 Uiso calc C9 H H5 0.9216 0.1493 0.9956 0.0749 Uiso calc C9 H H6 0.7010 0.0408 0.9540 0.0624 Uiso calc C10 H H7 0.6209 0.0896 0.8883 0.0624 Uiso calc C10 H H8 0.7117 0.0580 0.8427 0.0624 Uiso calc C10 H H9 0.7355 0.1299 1.0890 0.0877 Uiso calc C11 H H10 0.7741 0.2013 1.0635 0.0877 Uiso calc C11 H H11 0.6585 0.1793 1.0210 0.0877 Uiso calc C11 H H12 1.1846 0.3394 0.8548 0.0464 Uiso calc C12 H H13 1.0770 0.3191 0.8813 0.0464 Uiso calc C12 H H14 1.1000 0.4932 0.9309 0.0826 Uiso calc C15 H H15 1.0906 0.4233 0.9821 0.0826 Uiso calc C15 H H16 1.1940 0.4429 0.9464 0.0826 Uiso calc C15 H H17 0.9376 0.4680 0.7977 0.0711 Uiso calc C14 H H18 0.9306 0.4002 0.7374 0.0711 Uiso calc C14 H H19 0.9282 0.3997 0.8535 0.0711 Uiso calc C14 H H20 1.1001 0.4983 0.7413 0.0865 Uiso calc C16 H H21 1.1967 0.4499 0.7609 0.0865 Uiso calc C16 H H22 1.0974 0.4312 0.6799 0.0865 Uiso calc C16 H H23 1.1553 0.3008 0.3656 0.0457 Uiso calc C23 H H24 1.2680 0.2898 0.3447 0.0457 Uiso calc C23 H H25 1.2059 0.4464 0.2328 0.0732 Uiso calc C25 H H26 1.2465 0.3743 0.2142 0.0732 Uiso calc C25 H H27 1.1308 0.3845 0.2275 0.0732 Uiso calc C25 H H28 1.3536 0.4607 0.3855 0.0749 Uiso calc C26 H H29 1.3713 0.4056 0.4703 0.0749 Uiso calc C26 H H30 1.3940 0.3893 0.3626 0.0749 Uiso calc C26 H H31 1.1691 0.4764 0.4069 0.0814 Uiso calc C27 H H32 1.0925 0.4150 0.3968 0.0814 Uiso calc C27 H H33 1.1832 0.4212 0.4918 0.0814 Uiso calc C27 H H34 1.6455 0.1568 0.3820 0.0544 Uiso calc C28 H H35 1.5308 0.1829 0.3476 0.0544 Uiso calc C28 H H36 1.5390 0.0453 0.1862 0.1026 Uiso calc C30 H H37 1.5148 0.1224 0.1879 0.1026 Uiso calc C30 H H38 1.6299 0.0966 0.2211 0.1026 Uiso calc C30 H H39 1.5881 -0.0185 0.3516 0.0826 Uiso calc C31 H H40 1.6813 0.0315 0.3846 0.0826 Uiso calc C31 H H41 1.5998 0.0203 0.4546 0.0826 Uiso calc C31 H H42 1.4065 0.0243 0.2984 0.0878 Uiso calc C32 H H43 1.4152 0.0648 0.3998 0.0878 Uiso calc C32 H H44 1.3841 0.1017 0.2953 0.0878 Uiso calc C32 H H45 0.9364 0.2572 0.8323 0.0380 Uiso calc C1 H H46 0.9277 0.1627 0.4992 0.0496 Uiso calc C4 H H47 0.7341 0.1388 0.7296 0.0444 Uiso calc N1 H H48 1.1266 0.3129 0.6874 0.0435 Uiso calc N2 H H49 1.4007 0.2266 0.4051 0.0397 Uiso calc C17 H H50 1.4483 0.2044 0.7694 0.0471 Uiso calc C20 H H51 1.2248 0.3134 0.5387 0.0417 Uiso calc N3 H H52 1.6115 0.1246 0.5374 0.0479 Uiso calc N4 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 C1 0.029(2) 0.035(2) 0.024(2) 0.002(2) 0.008(2) -0.004(2) C C2 0.024(2) 0.030(2) 0.028(2) 0.003(2) 0.004(2) 0.002(2) C C3 0.038(2) 0.032(2) 0.027(2) 0.010(2) 0.004(2) -0.001(2) C C4 0.042(2) 0.048(2) 0.025(2) 0.006(2) 0.007(2) -0.002(2) C C5 0.036(2) 0.049(3) 0.026(2) 0.013(2) 0.006(2) 0.003(2) C C6 0.029(2) 0.035(2) 0.030(2) 0.001(2) 0.008(2) 0.006(2) C N1 0.037(2) 0.036(2) 0.030(2) -0.005(2) 0.008(1) -0.006(2) N C7 0.035(2) 0.041(2) 0.035(2) -0.008(2) 0.014(2) -0.003(2) C C8 0.042(2) 0.043(2) 0.027(2) -0.012(2) 0.005(2) 0.001(2) C C9 0.053(2) 0.067(3) 0.048(3) -0.013(2) -0.002(2) 0.010(2) C C10 0.047(2) 0.043(3) 0.050(3) -0.008(2) -0.000(2) 0.013(2) C C11 0.074(3) 0.089(4) 0.044(3) -0.030(3) 0.023(2) -0.004(3) C N2 0.030(2) 0.041(2) 0.031(2) 0.001(2) 0.012(1) 0.008(2) N C12 0.031(2) 0.041(2) 0.034(2) -0.004(2) 0.004(2) -0.002(2) C C13 0.048(2) 0.030(2) 0.041(2) -0.003(2) 0.016(2) 0.006(2) C C14 0.059(2) 0.049(3) 0.057(3) 0.016(2) 0.013(2) 0.007(2) C C15 0.078(3) 0.043(3) 0.070(3) -0.002(2) 0.016(3) -0.010(2) C C16 0.077(3) 0.045(3) 0.082(3) 0.001(3) 0.028(3) 0.023(3) C O1 0.040(1) 0.047(2) 0.046(2) -0.004(1) 0.008(1) -0.016(1) O O2 0.047(1) 0.071(2) 0.032(2) -0.002(2) 0.019(1) 0.001(1) O C17 0.035(2) 0.037(2) 0.023(2) 0.000(2) 0.014(2) 0.003(2) C C18 0.029(2) 0.028(2) 0.034(2) -0.008(2) 0.008(2) -0.002(2) C C19 0.035(2) 0.039(2) 0.029(2) -0.007(2) 0.011(2) -0.001(2) C C20 0.037(2) 0.045(2) 0.027(2) -0.000(2) 0.007(2) -0.003(2) C C21 0.031(2) 0.034(2) 0.032(2) -0.010(2) 0.002(2) 0.003(2) C C22 0.029(2) 0.029(2) 0.032(2) -0.001(2) 0.003(2) -0.004(2) C N3 0.033(2) 0.039(2) 0.027(2) 0.003(2) 0.014(1) -0.005(2) N C23 0.033(2) 0.038(2) 0.034(2) -0.002(2) 0.008(2) 0.001(2) C C24 0.032(2) 0.026(2) 0.039(2) -0.001(2) 0.011(2) 0.000(2) C C25 0.071(3) 0.043(3) 0.056(3) 0.010(2) 0.015(2) 0.016(2) C C26 0.058(3) 0.045(3) 0.074(3) -0.014(2) 0.021(2) -0.002(3) C C27 0.064(3) 0.047(3) 0.080(3) 0.009(3) 0.022(3) -0.008(3) C N4 0.039(2) 0.037(2) 0.036(2) 0.007(2) 0.011(2) 0.004(2) N C28 0.040(2) 0.047(3) 0.043(2) 0.003(2) 0.021(2) 0.004(2) C C29 0.046(2) 0.040(2) 0.036(2) 0.008(2) 0.012(2) -0.002(2) C C30 0.117(3) 0.076(3) 0.052(3) 0.026(3) 0.038(3) -0.004(3) C C31 0.075(3) 0.050(3) 0.068(3) 0.011(3) 0.019(3) -0.004(3) C C32 0.066(3) 0.064(3) 0.069(3) 0.000(3) 0.006(3) -0.019(3) C O3 0.046(1) 0.056(2) 0.036(2) 0.000(1) 0.017(1) -0.010(1) O O4 0.041(1) 0.052(2) 0.034(2) 0.002(1) 0.002(1) 0.005(1) 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 C1 C2 1.383(5) . . ? C1 C6 1.378(5) . . ? C2 C3 1.527(5) . . ? C2 N1 1.312(4) . . ? C3 C4 1.389(5) . . ? C3 O1 1.259(4) . . ? C4 C5 1.394(5) . . ? C5 C6 1.537(5) . . ? C5 O2 1.251(4) . . ? C6 N2 1.324(4) . . ? N1 C7 1.450(5) . . ? C7 C8 1.515(5) . . ? C8 C9 1.532(5) . . ? C8 C10 1.521(5) . . ? C8 C11 1.527(6) . . ? N2 C12 1.456(5) . . ? C12 C13 1.527(5) . . ? C13 C14 1.516(5) . . ? C13 C15 1.532(5) . . ? C13 C16 1.516(6) . . ? C17 C18 1.388(5) . . ? C17 C22 1.368(5) . . ? C18 C19 1.534(5) . . ? C18 N3 1.315(4) . . ? C19 C20 1.382(5) . . ? C19 O3 1.258(4) . . ? C20 C21 1.386(5) . . ? C21 C22 1.518(5) . . ? C21 O4 1.262(4) . . ? C22 N4 1.322(4) . . ? N3 C23 1.449(4) . . ? C23 C24 1.526(5) . . ? C24 C25 1.527(5) . . ? C24 C26 1.525(5) . . ? C24 C27 1.522(5) . . ? N4 C28 1.456(5) . . ? C28 C29 1.525(5) . . ? C29 C30 1.524(6) . . ? C29 C31 1.518(5) . . ? C29 C32 1.524(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 C2 C1 C6 119.3(4) . . . ? C1 C2 C3 121.5(4) . . . ? C1 C2 N1 126.2(4) . . . ? C3 C2 N1 112.3(4) . . . ? C2 C3 C4 117.5(4) . . . ? C2 C3 O1 116.9(4) . . . ? C4 C3 O1 125.6(4) . . . ? C3 C4 C5 123.1(4) . . . ? C4 C5 C6 116.9(4) . . . ? C4 C5 O2 126.0(4) . . . ? C6 C5 O2 117.1(4) . . . ? C1 C6 C5 121.6(4) . . . ? C1 C6 N2 126.3(4) . . . ? C5 C6 N2 112.1(4) . . . ? C2 N1 C7 129.4(3) . . . ? N1 C7 C8 114.1(4) . . . ? C7 C8 C9 109.3(3) . . . ? C7 C8 C10 111.4(3) . . . ? C7 C8 C11 107.4(4) . . . ? C9 C8 C10 109.5(4) . . . ? C9 C8 C11 110.0(3) . . . ? C10 C8 C11 109.2(4) . . . ? C6 N2 C12 128.0(4) . . . ? N2 C12 C13 114.4(3) . . . ? C12 C13 C14 110.7(3) . . . ? C12 C13 C15 106.6(3) . . . ? C12 C13 C16 110.5(4) . . . ? C14 C13 C15 109.9(4) . . . ? C14 C13 C16 109.2(3) . . . ? C15 C13 C16 110.0(4) . . . ? C18 C17 C22 119.0(4) . . . ? C17 C18 C19 121.7(4) . . . ? C17 C18 N3 126.1(4) . . . ? C19 C18 N3 112.1(4) . . . ? C18 C19 C20 116.7(4) . . . ? C18 C19 O3 117.1(4) . . . ? C20 C19 O3 126.2(4) . . . ? C19 C20 C21 122.9(4) . . . ? C20 C21 C22 118.1(4) . . . ? C20 C21 O4 125.6(4) . . . ? C22 C21 O4 116.3(4) . . . ? C17 C22 C21 121.3(4) . . . ? C17 C22 N4 125.9(4) . . . ? C21 C22 N4 112.8(4) . . . ? C18 N3 C23 128.5(3) . . . ? N3 C23 C24 113.8(3) . . . ? C23 C24 C25 107.1(3) . . . ? C23 C24 C26 110.4(3) . . . ? C23 C24 C27 109.9(4) . . . ? C25 C24 C26 109.7(4) . . . ? C25 C24 C27 109.8(3) . . . ? C26 C24 C27 109.9(3) . . . ? C22 N4 C28 128.2(3) . . . ? N4 C28 C29 113.5(4) . . . ? C28 C29 C30 107.3(4) . . . ? C28 C29 C31 111.0(3) . . . ? C28 C29 C32 109.5(4) . . . ? C30 C29 C31 110.3(4) . . . ? C30 C29 C32 109.2(3) . . . ? C31 C29 C32 109.6(4) . . . ? #=========================================================================== data_6.2H2O (CCDC 149253) _database_code_CSD 149253 #=========================================================================== _audit_creation_date 8-10-01 # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 6.2H2O' _chemical_formula_moiety 'C16 H30 N2 O4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H30 N2 O4' _chemical_formula_weight 314.43 _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 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 monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' -x,+y,1/2-z -x,-y,-z +x,-y,1/2+z 1/2+x,1/2+y,+z 1/2-x,1/2+y,1/2-z 1/2-x,1/2-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 24.998(2) _cell_length_b 16.728(1) _cell_length_c 8.8553(6) _cell_angle_alpha 90 _cell_angle_beta 102.112(5) _cell_angle_gamma 90 _cell_volume 3620.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173 _cell_measurement_reflns_used 6881 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 27.5 _cell_special_details ; Cell parameters refined using Scalepack part of DENZO Z. Otwinowski, W. Minor, 1997 ; _exptl_crystal_description prism _exptl_crystal_colour 'purple' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.15 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=========================================================================== # 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 ; 6881 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 80 sec per frame. Data collection was divided into 1 set(s) with the following starting angles and number of frames : Set 1 Theta == 6.30 Omega == 0.00 Kappa == 0.00 90 frames Friedel pairs were averaged. Internal R == 0.06 ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6881 _diffrn_reflns_av_R_equivalents 0.060 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4281 _reflns_number_gt 1571 _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 1571 _refine_ls_number_parameters 199 _refine_ls_number_restraints 8 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.216 _refine_ls_R_factor_gt 0.056 _refine_ls_wR_factor_all 0.716 _refine_ls_wR_factor_ref 0.080 _refine_ls_goodness_of_fit_all 12.857 _refine_ls_goodness_of_fit_ref 1.311 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.215 _refine_diff_density_min -0.149 #=========================================================================== # 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 C1 0.2408(2) 0.1091(2) 0.1592(4) 0.021(2) Uani ? ? C C2 0.2288(1) 0.0813(2) 0.0093(4) 0.020(2) Uani ? ? C C3 0.1966(1) 0.1346(2) -0.1158(4) 0.020(2) Uani ? ? C C4 0.1783(1) 0.2096(2) -0.0806(4) 0.019(2) Uani ? ? C C5 0.1900(1) 0.2358(2) 0.0717(4) 0.019(2) Uani ? ? C C6 0.2232(1) 0.1841(2) 0.1992(4) 0.020(2) Uani ? ? C O1 0.2431(1) 0.0144(1) -0.0361(3) 0.030(1) Uani ? ? O N1 0.1887(1) 0.1026(2) -0.2553(3) 0.021(2) Uani ? ? N C7 0.1617(2) 0.1380(2) -0.4005(4) 0.025(2) Uani ? ? C C8 0.1028(2) 0.1089(2) -0.4623(4) 0.027(2) Uani ? ? C C9 0.1017(2) 0.0189(3) -0.4821(5) 0.044(3) Uani ? ? C C10 0.0655(2) 0.1337(3) -0.3555(5) 0.040(3) Uani ? ? C C11 0.0830(2) 0.1488(3) -0.6201(6) 0.054(3) Uani ? ? C N2 0.1748(1) 0.3048(2) 0.1218(3) 0.020(2) Uani ? ? N C12 0.1432(2) 0.3667(2) 0.0281(4) 0.026(2) Uani ? ? C C13 0.0825(1) 0.3678(2) 0.0328(4) 0.026(2) Uani ? ? C C14 0.0549(2) 0.2909(3) -0.0278(6) 0.047(3) Uani ? ? C C15 0.0760(2) 0.3824(3) 0.1973(5) 0.051(3) Uani ? ? C C16 0.0570(2) 0.4372(3) -0.0686(5) 0.053(3) Uani ? ? C O2 0.2326(1) 0.2133(1) 0.3326(3) 0.028(1) Uani ? ? O O3 0.3017(1) -0.1247(1) 0.0613(3) 0.029(1) Uani ? ? O O4 0.3854(2) -0.1481(2) -0.1084(4) 0.090(3) Uani ? ? O H01 0.2064 0.0443 -0.2481 0.0317 Uiso ? ? H H02 0.1910 0.3157 0.2422 0.0317 Uiso ? ? H H1 0.2615 0.0763 0.2377 0.0286 Uiso calc C1 H H2 0.1580 0.2425 -0.1598 0.0255 Uiso calc C4 H H3 0.1827 0.1260 -0.4755 0.0350 Uiso calc C7 H H4 0.1608 0.1943 -0.3867 0.0350 Uiso calc C7 H H5 0.0652 0.0018 -0.5202 0.0598 Uiso calc C9 H H6 0.1237 0.0043 -0.5532 0.0598 Uiso calc C9 H H7 0.1157 -0.0058 -0.3852 0.0598 Uiso calc C9 H H8 0.0295 0.1151 -0.3960 0.0561 Uiso calc C10 H H9 0.0785 0.1112 -0.2561 0.0561 Uiso calc C10 H H10 0.0652 0.1903 -0.3476 0.0561 Uiso calc C10 H H11 0.0466 0.1323 -0.6625 0.0766 Uiso calc C11 H H12 0.0840 0.2052 -0.6081 0.0766 Uiso calc C11 H H13 0.1061 0.1335 -0.6876 0.0766 Uiso calc C11 H H14 0.1463 0.3590 -0.0760 0.0337 Uiso calc C12 H H15 0.1584 0.4171 0.0636 0.0337 Uiso calc C12 H H16 0.0172 0.2933 -0.0235 0.0690 Uiso calc C14 H H17 0.0582 0.2833 -0.1318 0.0690 Uiso calc C14 H H18 0.0717 0.2475 0.0335 0.0690 Uiso calc C14 H H19 0.0383 0.3831 0.2001 0.0696 Uiso calc C15 H H20 0.0938 0.3409 0.2623 0.0696 Uiso calc C15 H H21 0.0920 0.4324 0.2323 0.0696 Uiso calc C15 H H22 0.0190 0.4400 -0.0689 0.0698 Uiso calc C16 H H23 0.0742 0.4857 -0.0291 0.0698 Uiso calc C16 H H24 0.0619 0.4292 -0.1710 0.0698 Uiso calc C16 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 C1 0.026(2) 0.019(2) 0.018(2) 0.003(2) -0.002(2) 0.006(2) C C2 0.018(2) 0.020(2) 0.023(2) 0.001(2) 0.001(2) 0.001(2) C C3 0.015(2) 0.024(2) 0.021(2) -0.003(2) 0.006(1) -0.003(2) C C4 0.018(2) 0.021(2) 0.018(2) 0.004(2) -0.001(2) 0.005(2) C C5 0.017(2) 0.023(2) 0.018(2) -0.004(2) 0.002(1) 0.002(2) C C6 0.020(2) 0.022(2) 0.019(2) -0.006(2) 0.001(2) 0.000(2) C O1 0.046(2) 0.019(1) 0.032(2) 0.010(1) -0.002(1) -0.005(1) O N1 0.023(2) 0.025(1) 0.017(2) 0.003(2) 0.001(1) -0.004(1) N C7 0.033(2) 0.031(2) 0.016(2) 0.003(2) 0.004(2) -0.001(2) C C8 0.027(2) 0.033(2) 0.023(2) 0.004(2) -0.002(2) 0.001(2) C C9 0.038(3) 0.044(2) 0.050(3) -0.002(2) -0.003(2) -0.017(2) C C10 0.026(2) 0.058(3) 0.043(3) 0.004(2) 0.001(2) -0.004(3) C C11 0.056(3) 0.072(3) 0.038(3) 0.005(3) -0.014(3) 0.004(3) C N2 0.019(2) 0.019(1) 0.022(2) 0.003(1) 0.002(1) -0.002(1) N C12 0.031(2) 0.021(2) 0.027(2) 0.006(2) 0.010(2) -0.001(2) C C13 0.020(2) 0.030(2) 0.028(2) 0.003(2) 0.002(2) -0.003(2) C C14 0.024(2) 0.057(3) 0.076(3) -0.001(2) 0.006(2) -0.014(3) C C15 0.034(2) 0.084(3) 0.046(2) 0.016(3) 0.016(2) -0.006(3) C C16 0.049(3) 0.060(3) 0.051(3) 0.031(3) 0.007(2) 0.005(3) C O2 0.039(2) 0.031(1) 0.017(1) 0.005(1) -0.001(1) -0.001(1) O O3 0.033(1) 0.029(1) 0.025(1) 0.002(1) -0.000(1) 0.007(1) O O4 0.100(3) 0.100(3) 0.072(2) -0.006(3) 0.028(2) -0.008(2) 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 C1 C2 1.379(5) . . ? C1 C6 1.399(5) . . ? C2 C3 1.516(5) . . ? C2 O1 1.265(4) . . ? C3 C4 1.393(5) . . ? C3 N1 1.323(5) . . ? C3 H01 1.9575 . . ? C4 C5 1.389(5) . . ? C5 C6 1.523(5) . . ? C5 N2 1.320(5) . . ? C5 H02 2.0129 . . ? C6 O2 1.254(4) . . ? O1 H01 1.9735 . . ? N1 C7 1.448(5) . . ? N1 H01 1.0662 . . ? C7 C8 1.538(6) . . ? C8 C9 1.515(6) . . ? C8 C10 1.518(6) . . ? C8 C11 1.534(7) . . ? N2 C12 1.453(5) . . ? N2 H02 1.0742 . . ? C12 C13 1.529(6) . . ? C12 H02 2.1907 . . ? C13 C14 1.504(6) . . ? C13 C15 1.518(6) . . ? C13 C16 1.524(6) . . ? O2 H02 2.0760 . . ? O3 H02 1.9804 . 6_545 ? 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 C2 C1 C6 122.0(4) . . . ? C1 C2 C3 118.7(3) . . . ? C1 C2 O1 125.8(4) . . . ? C3 C2 O1 115.5(4) . . . ? C2 C3 C4 121.0(3) . . . ? C2 C3 N1 113.4(3) . . . ? C2 C3 H01 82.49 . . . ? C4 C3 N1 125.6(4) . . . ? C4 C3 H01 156.48 . . . ? N1 C3 H01 30.88 . . . ? C3 C4 C5 119.3(3) . . . ? C4 C5 C6 120.8(3) . . . ? C4 C5 N2 125.7(4) . . . ? C4 C5 H02 154.70 . . . ? C6 C5 N2 113.5(3) . . . ? C6 C5 H02 84.40 . . . ? N2 C5 H02 29.17 . . . ? C1 C6 C5 118.2(4) . . . ? C1 C6 O2 125.5(4) . . . ? C5 C6 O2 116.2(3) . . . ? C2 O1 H01 88.38 . . . ? C3 N1 C7 127.9(3) . . . ? C3 N1 H01 109.58 . . . ? C7 N1 H01 122.54 . . . ? N1 C7 C8 114.8(3) . . . ? C7 C8 C9 110.4(4) . . . ? C7 C8 C10 111.1(3) . . . ? C7 C8 C11 106.8(4) . . . ? C9 C8 C10 110.2(4) . . . ? C9 C8 C11 109.4(4) . . . ? C10 C8 C11 109.0(4) . . . ? C5 N2 C12 126.3(3) . . . ? C5 N2 H02 114.01 . . . ? C12 N2 H02 119.47 . . . ? N2 C12 C13 114.7(3) . . . ? N2 C12 H02 25.27 . . . ? C13 C12 H02 110.24 . . . ? C12 C13 C14 111.4(3) . . . ? C12 C13 C15 109.5(4) . . . ? C12 C13 C16 106.7(4) . . . ? C14 C13 C15 110.3(4) . . . ? C14 C13 C16 109.7(4) . . . ? C15 C13 C16 109.1(4) . . . ? C6 O2 H02 88.78 . . . ? C3 H01 O1 73.63 . . . ? C3 H01 N1 39.54 . . . ? O1 H01 N1 113.16 . . . ? C5 H02 N2 36.82 . . . ? C5 H02 C12 72.00 . . . ? C5 H02 O2 70.56 . . . ? C5 H02 O3 167.90 . . 6_555 ? N2 H02 C12 35.26 . . . ? N2 H02 O2 107.24 . . . ? N2 H02 O3 154.68 . . 6_555 ? C12 H02 O2 142.50 . . . ? C12 H02 O3 119.79 . . 6_555 ? O2 H02 O3 97.51 . . 6_555 ?