Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Prof. Shyamaprosad Goswami' _publ_contact_author_address ; X-ray Crystallography Unit School of Physics Universiti Sains Malaysia 11800 USM, Penang Malaysia ; _publ_contact_author_email SPGOSWAMICAL@YAHOO.COM _publ_contact_author_fax '6 04 6579150' _publ_contact_author_phone '6 04 6577888 Ext. 3690' _publ_contact_letter ; Date : 7 May 2007 Manager Cambridge Crystallographic Data Centre 12 Union Road Cambridge CB2 1EZ England Ref: Deposition of Crystal Structure Data - Paper to be submitted to Journal of Organic Chemistry. Dear Sir, I herewith attach the crystal structure data in the CIF format for the structure appearing in a manuscript entitled Recognition of Dicarboxylic Acids by 3,3/-Bipyridine Amide Based Receptors and Its Supramolecular Behavior in the Solid State This manuscript shall be submitted to the journal "Journal of Organic Chemistry". I request you to kindly acknowledge this deposition and send me the CCDC reference number for this structure so as to enable me to inform to the editor of the "Journal of Organic Chemistry" Yours Sincerely, Fun Hoong-Kun ; #============================================================================ # TITLE AND AUTHOR LIST _publ_section_title ; Recognition of Dicarboxylic Acids by 3,3/-Bipyridine Amide Based Receptors and Its Supramolecular Behavior in Solid State ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Shyamaprosad Goswami' ? ; Department of Chemistry Bengal Engineering and Science University Shibpur, Howrah-711103, India ; 'Subrata Jana' ? ; Department of Chemistry Bengal Engineering and Science University Shibpur, Howrah-711103, India ; 'Hoong-Kun Fun.' ? ; X-ray Crystallography Unit School of Physics Universiti Sains Malaysia 11800 USM, Penang Malaysia ; #============================================================================ _publ_section_exptl_refinement ; All the H atoms were located in a difference Fourier map and were refined with isotropic displacement factors. ; #============================================================================ data_spg376am _database_code_depnum_ccdc_archive 'CCDC 646488' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Recognition of Dicarboxylic Acids by 3,3/-Bipyridine Amide Based Receptors and Its Supramolecular Behavior in the Solid State ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H18 N2 O3' _chemical_formula_weight 250.29 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7920(4) _cell_length_b 9.9488(7) _cell_length_c 12.1657(8) _cell_angle_alpha 98.753(2) _cell_angle_beta 103.129(1) _cell_angle_gamma 91.122(1) _cell_volume 673.69(8) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1287 _cell_measurement_theta_min 1.74 _cell_measurement_theta_max 30.09 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9440 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details 'SADABS (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Brucker SMART APEX2 CCD diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8512 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 30.09 _reflns_number_total 3928 _reflns_number_gt 2025 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement APEX2 _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL and PLATON (Spek, 2003) ; _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^)+(0.0872P)^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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3928 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1151 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1851 _refine_ls_wR_factor_gt 0.1494 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 N1 N 0.4474(3) 0.88921(14) 0.13736(14) 0.0574(4) Uani 1 1 d . . . N2 N 0.5263(3) 0.67634(14) 0.18144(13) 0.0541(4) Uani 1 1 d . . . C1 C 0.3018(3) 0.97833(18) 0.08904(17) 0.0580(5) Uani 1 1 d . . . C2 C 0.0753(3) 0.94707(16) 0.02319(14) 0.0477(4) Uani 1 1 d . . . C3 C 0.0008(4) 0.81034(19) 0.00673(18) 0.0617(5) Uani 1 1 d . . . C4 C 0.1442(4) 0.71590(19) 0.05389(17) 0.0617(5) Uani 1 1 d . . . C5 C 0.3691(3) 0.75954(16) 0.12119(14) 0.0485(4) Uani 1 1 d . . . C6 C 0.4989(3) 0.53798(17) 0.17717(16) 0.0510(4) Uani 1 1 d . . . C7 C 0.6736(3) 0.48102(18) 0.27104(19) 0.0592(5) Uani 1 1 d . . . C8 C 0.6027(6) 0.3305(3) 0.2616(4) 0.1073(12) Uani 1 1 d . . . C9 C 0.6580(6) 0.5574(3) 0.3885(2) 0.0844(8) Uani 1 1 d . . . C10 C 0.9262(4) 0.4964(3) 0.2562(3) 0.0792(7) Uani 1 1 d . . . O1 O 0.3465(3) 0.46750(13) 0.10614(13) 0.0714(5) Uani 1 1 d . . . O2 O 0.8518(3) 1.02538(14) 0.25766(14) 0.0769(5) Uani 1 1 d . . . C11 C 0.9936(3) 0.95726(18) 0.32578(16) 0.0531(5) Uani 1 1 d . . . C12 C 1.2136(4) 1.0386(2) 0.3951(2) 0.0610(5) Uani 1 1 d . . . C13 C 1.3937(3) 0.9567(2) 0.4628(2) 0.0605(5) Uani 1 1 d . . . O3 O 0.9489(3) 0.84059(14) 0.33226(15) 0.0839(5) Uani 1 1 d . . . H1 H 0.365(4) 1.071(2) 0.1055(17) 0.068(6) Uiso 1 1 d . . . H3 H -0.162(4) 0.778(2) -0.0362(19) 0.083(7) Uiso 1 1 d . . . H4 H 0.079(4) 0.622(2) 0.0467(18) 0.077(6) Uiso 1 1 d . . . H8A H 0.611(7) 0.282(4) 0.181(3) 0.147(15) Uiso 1 1 d . . . H8B H 0.432(7) 0.316(3) 0.269(3) 0.148(13) Uiso 1 1 d . . . H8C H 0.709(7) 0.304(3) 0.331(3) 0.140(12) Uiso 1 1 d . . . H9A H 0.491(7) 0.567(3) 0.395(3) 0.143(13) Uiso 1 1 d . . . H9B H 0.724(5) 0.655(3) 0.401(2) 0.101(8) Uiso 1 1 d . . . H9C H 0.761(5) 0.515(2) 0.447(2) 0.097(8) Uiso 1 1 d . . . H10A H 0.930(6) 0.452(4) 0.174(3) 0.148(13) Uiso 1 1 d . . . H10B H 1.017(5) 0.438(3) 0.306(2) 0.103(9) Uiso 1 1 d . . . H10C H 0.973(5) 0.595(3) 0.265(2) 0.105(9) Uiso 1 1 d . . . H12A H 1.273(5) 1.093(3) 0.345(2) 0.098(8) Uiso 1 1 d . . . H12B H 1.160(4) 1.114(2) 0.445(2) 0.089(7) Uiso 1 1 d . . . H13A H 1.323(4) 0.904(2) 0.5118(19) 0.079(7) Uiso 1 1 d . . . H13B H 1.444(4) 0.882(2) 0.414(2) 0.085(7) Uiso 1 1 d . . . H1N2 H 0.666(4) 0.728(2) 0.2327(19) 0.075(6) Uiso 1 1 d . . . H1O2 H 0.698(5) 0.964(3) 0.212(2) 0.111(9) 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 N1 0.0416(8) 0.0434(7) 0.0732(10) 0.0130(7) -0.0174(7) -0.0049(6) N2 0.0435(8) 0.0417(7) 0.0646(9) 0.0108(7) -0.0141(7) -0.0023(7) C1 0.0424(9) 0.0433(9) 0.0752(12) 0.0132(8) -0.0149(9) -0.0038(8) C2 0.0404(9) 0.0456(8) 0.0483(9) 0.0093(7) -0.0089(8) -0.0025(7) C3 0.0460(10) 0.0496(10) 0.0726(12) 0.0113(9) -0.0208(9) -0.0075(8) C4 0.0525(11) 0.0443(9) 0.0719(12) 0.0135(8) -0.0208(9) -0.0082(8) C5 0.0422(9) 0.0445(8) 0.0502(9) 0.0093(7) -0.0080(8) 0.0002(7) C6 0.0388(9) 0.0448(9) 0.0650(11) 0.0084(8) 0.0031(8) 0.0005(7) C7 0.0444(10) 0.0472(9) 0.0818(13) 0.0200(9) -0.0008(10) 0.0066(8) C8 0.081(2) 0.0559(13) 0.168(3) 0.0458(18) -0.024(2) -0.0015(13) C9 0.0844(19) 0.099(2) 0.0726(15) 0.0375(14) 0.0076(14) 0.0185(16) C10 0.0486(12) 0.0750(15) 0.110(2) 0.0173(15) 0.0085(13) 0.0146(12) O1 0.0586(8) 0.0468(7) 0.0905(10) 0.0048(7) -0.0152(8) -0.0072(6) O2 0.0525(8) 0.0551(8) 0.1020(11) 0.0179(7) -0.0283(8) -0.0033(7) C11 0.0394(9) 0.0469(9) 0.0617(11) 0.0040(8) -0.0081(8) 0.0011(8) C12 0.0453(10) 0.0496(10) 0.0739(13) 0.0064(10) -0.0127(10) -0.0034(9) C13 0.0401(10) 0.0527(10) 0.0744(13) 0.0058(10) -0.0127(10) -0.0005(9) O3 0.0675(10) 0.0546(8) 0.1046(12) 0.0222(7) -0.0359(8) -0.0129(7) _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 N1 C5 1.330(2) . ? N1 C1 1.344(2) . ? N2 C6 1.374(2) . ? N2 C5 1.401(2) . ? N2 H1N2 0.98(2) . ? C1 C2 1.375(2) . ? C1 H1 0.96(2) . ? C2 C3 1.390(3) . ? C2 C2 1.477(3) 2_575 ? C3 C4 1.371(3) . ? C3 H3 0.99(2) . ? C4 C5 1.393(2) . ? C4 H4 0.98(2) . ? C6 O1 1.209(2) . ? C6 C7 1.531(3) . ? C7 C10 1.521(3) . ? C7 C8 1.525(3) . ? C7 C9 1.536(3) . ? C8 H8A 1.03(4) . ? C8 H8B 1.02(4) . ? C8 H8C 1.00(4) . ? C9 H9A 0.99(4) . ? C9 H9B 1.02(3) . ? C9 H9C 0.97(3) . ? C10 H10A 1.04(4) . ? C10 H10B 0.97(3) . ? C10 H10C 1.00(3) . ? O2 C11 1.306(2) . ? O2 H1O2 1.06(3) . ? C11 O3 1.202(2) . ? C11 C12 1.501(2) . ? C12 C13 1.509(3) . ? C12 H12A 0.99(3) . ? C12 H12B 0.99(2) . ? C13 C13 1.514(4) 2_876 ? C13 H13A 1.00(2) . ? C13 H13B 0.97(2) . ? 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 C5 N1 C1 118.28(15) . . ? C6 N2 C5 127.17(14) . . ? C6 N2 H1N2 120.4(12) . . ? C5 N2 H1N2 112.4(13) . . ? N1 C1 C2 125.42(16) . . ? N1 C1 H1 114.9(13) . . ? C2 C1 H1 119.6(13) . . ? C1 C2 C3 114.70(16) . . ? C1 C2 C2 121.64(19) . 2_575 ? C3 C2 C2 123.64(19) . 2_575 ? C4 C3 C2 121.76(17) . . ? C4 C3 H3 117.2(13) . . ? C2 C3 H3 121.0(13) . . ? C3 C4 C5 118.65(17) . . ? C3 C4 H4 119.1(13) . . ? C5 C4 H4 121.9(13) . . ? N1 C5 C4 121.17(16) . . ? N1 C5 N2 114.14(15) . . ? C4 C5 N2 124.62(15) . . ? O1 C6 N2 122.63(17) . . ? O1 C6 C7 122.83(16) . . ? N2 C6 C7 114.53(15) . . ? C10 C7 C8 109.7(2) . . ? C10 C7 C6 110.64(19) . . ? C8 C7 C6 107.72(19) . . ? C10 C7 C9 109.7(2) . . ? C8 C7 C9 109.7(3) . . ? C6 C7 C9 109.38(17) . . ? C7 C8 H8A 108(2) . . ? C7 C8 H8B 112(2) . . ? H8A C8 H8B 107(3) . . ? C7 C8 H8C 103.2(19) . . ? H8A C8 H8C 120(3) . . ? H8B C8 H8C 107(3) . . ? C7 C9 H9A 112(2) . . ? C7 C9 H9B 111.4(15) . . ? H9A C9 H9B 103(2) . . ? C7 C9 H9C 108.0(14) . . ? H9A C9 H9C 117(2) . . ? H9B C9 H9C 105(2) . . ? C7 C10 H10A 109(2) . . ? C7 C10 H10B 104.7(16) . . ? H10A C10 H10B 105(2) . . ? C7 C10 H10C 109.1(16) . . ? H10A C10 H10C 108(2) . . ? H10B C10 H10C 121(2) . . ? C11 O2 H1O2 110.7(14) . . ? O3 C11 O2 122.47(16) . . ? O3 C11 C12 123.79(17) . . ? O2 C11 C12 113.73(16) . . ? C11 C12 C13 114.31(16) . . ? C11 C12 H12A 107.9(15) . . ? C13 C12 H12A 116.1(16) . . ? C11 C12 H12B 106.7(15) . . ? C13 C12 H12B 111.9(14) . . ? H12A C12 H12B 98(2) . . ? C12 C13 C13 112.9(2) . 2_876 ? C12 C13 H13A 112.3(13) . . ? C13 C13 H13A 108.7(13) 2_876 . ? C12 C13 H13B 112.3(14) . . ? C13 C13 H13B 110.5(15) 2_876 . ? H13A C13 H13B 99.3(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 0.0(3) . . . . ? N1 C1 C2 C3 -0.9(3) . . . . ? N1 C1 C2 C2 177.8(2) . . . 2_575 ? C1 C2 C3 C4 0.4(3) . . . . ? C2 C2 C3 C4 -178.2(2) 2_575 . . . ? C2 C3 C4 C5 0.8(3) . . . . ? C1 N1 C5 C4 1.4(3) . . . . ? C1 N1 C5 N2 -175.64(17) . . . . ? C3 C4 C5 N1 -1.8(3) . . . . ? C3 C4 C5 N2 174.90(18) . . . . ? C6 N2 C5 N1 -176.59(17) . . . . ? C6 N2 C5 C4 6.5(3) . . . . ? C5 N2 C6 O1 11.2(3) . . . . ? C5 N2 C6 C7 -167.60(17) . . . . ? O1 C6 C7 C10 115.2(2) . . . . ? N2 C6 C7 C10 -66.0(2) . . . . ? O1 C6 C7 C8 -4.7(3) . . . . ? N2 C6 C7 C8 174.1(2) . . . . ? O1 C6 C7 C9 -123.9(2) . . . . ? N2 C6 C7 C9 55.0(2) . . . . ? O3 C11 C12 C13 8.1(3) . . . . ? O2 C11 C12 C13 -172.54(19) . . . . ? C11 C12 C13 C13 -176.5(3) . . . 2_876 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.09 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.161 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.039 # Attachment 'complex_B_ccdc_cif.txt' data_spg376b _database_code_depnum_ccdc_archive 'CCDC 603755' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H36 N4 O6' _chemical_formula_weight 548.63 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.4295(3) _cell_length_b 9.8850(4) _cell_length_c 21.8431(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.739(3) _cell_angle_gamma 90.00 _cell_volume 1385.3(1) _cell_formula_units_Z 2 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 3225 _cell_measurement_theta_min 1.87 _cell_measurement_theta_max 30.81 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9491 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details 'SADABS (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Brucker SMART APEX2 CCD diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17515 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 30.81 _reflns_number_total 4325 _reflns_number_gt 2950 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement APEX2 _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL and PLATON (Spek, 2003) ; _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^)+(0.0636P)^2^+0.0469P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4325 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0835 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1337 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 O1 O 0.46055(18) 0.20324(9) 0.15766(5) 0.0318(3) Uani 1 1 d . . . O2 O 0.45613(16) 0.79729(10) 0.09654(5) 0.0271(3) Uani 1 1 d . . . O3 O 0.19477(16) 0.69011(10) 0.13800(5) 0.0314(3) Uani 1 1 d . . . N1 N 0.62397(18) 0.56130(11) 0.07535(5) 0.0211(3) Uani 1 1 d . . . N2 N 0.41336(19) 0.42253(12) 0.12859(5) 0.0216(3) Uani 1 1 d . . . C1 C 0.7854(2) 0.58396(14) 0.04071(6) 0.0220(3) Uani 1 1 d . . . C2 C 0.9079(2) 0.48304(13) 0.01735(5) 0.0180(3) Uani 1 1 d . . . C3 C 0.8441(2) 0.35073(14) 0.02858(6) 0.0216(3) Uani 1 1 d . . . C4 C 0.6758(2) 0.32449(13) 0.06320(6) 0.0223(3) Uani 1 1 d . . . C5 C 0.5730(2) 0.43341(13) 0.08817(6) 0.0188(3) Uani 1 1 d . . . C6 C 0.3788(2) 0.31256(13) 0.16561(6) 0.0204(3) Uani 1 1 d . . . C7 C 0.2349(2) 0.33920(13) 0.21772(6) 0.0205(3) Uani 1 1 d . . . C8 C 0.0142(2) 0.36940(17) 0.19121(7) 0.0296(3) Uani 1 1 d . . . C9 C 0.3212(3) 0.45886(16) 0.25683(7) 0.0277(3) Uani 1 1 d . . . C10 C 0.2326(3) 0.21223(15) 0.25819(7) 0.0294(4) Uani 1 1 d . . . C11 C 0.2741(2) 0.79397(13) 0.12076(6) 0.0211(3) Uani 1 1 d . . . C12 C 0.1715(2) 0.93138(14) 0.12324(6) 0.0228(3) Uani 1 1 d . . . C13 C 0.0810(2) 0.97060(13) 0.06001(6) 0.0202(3) Uani 1 1 d . . . C14 C -0.1300(2) 0.95379(13) 0.04353(6) 0.0216(3) Uani 1 1 d . . . C15 C -0.2106(2) 0.98145(13) -0.01567(6) 0.0218(3) Uani 1 1 d . . . H1 H 0.812(3) 0.6781(17) 0.0327(7) 0.026(4) Uiso 1 1 d . . . H3 H 0.914(2) 0.2748(16) 0.0139(7) 0.021(4) Uiso 1 1 d . . . H4 H 0.629(3) 0.2358(18) 0.0697(7) 0.028(4) Uiso 1 1 d . . . H8A H -0.079(3) 0.3865(18) 0.2261(7) 0.037(5) Uiso 1 1 d . . . H8B H 0.013(3) 0.4512(18) 0.1641(7) 0.033(4) Uiso 1 1 d . . . H8C H -0.040(3) 0.2867(19) 0.1661(8) 0.040(5) Uiso 1 1 d . . . H9A H 0.243(3) 0.4670(17) 0.2939(8) 0.033(4) Uiso 1 1 d . . . H9B H 0.476(3) 0.4439(19) 0.2676(8) 0.043(5) Uiso 1 1 d . . . H9C H 0.303(3) 0.5446(19) 0.2333(7) 0.036(5) Uiso 1 1 d . . . H10A H 0.181(3) 0.133(2) 0.2330(8) 0.044(5) Uiso 1 1 d . . . H10B H 0.137(3) 0.2281(17) 0.2917(7) 0.030(4) Uiso 1 1 d . . . H10C H 0.379(3) 0.190(2) 0.2767(8) 0.046(5) Uiso 1 1 d . . . H12A H 0.058(2) 0.9265(15) 0.1513(7) 0.023(4) Uiso 1 1 d . . . H12B H 0.276(3) 0.9914(17) 0.1389(7) 0.027(4) Uiso 1 1 d . . . H14A H -0.227(3) 0.9195(17) 0.0729(7) 0.032(4) Uiso 1 1 d . . . H15A H -0.355(3) 0.9679(16) -0.0257(6) 0.023(4) Uiso 1 1 d . . . H1N2 H 0.349(3) 0.4970(18) 0.1356(7) 0.028(4) Uiso 1 1 d . . . H1O2 H 0.518(3) 0.700(2) 0.0933(9) 0.065(7) 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 O1 0.0418(7) 0.0171(5) 0.0387(6) 0.0036(4) 0.0203(5) 0.0037(4) O2 0.0234(6) 0.0174(5) 0.0418(6) 0.0016(4) 0.0119(5) 0.0011(4) O3 0.0300(6) 0.0226(5) 0.0434(6) 0.0073(4) 0.0157(5) 0.0027(4) N1 0.0203(6) 0.0172(5) 0.0265(6) 0.0030(4) 0.0067(5) 0.0021(4) N2 0.0225(6) 0.0174(6) 0.0259(6) 0.0026(4) 0.0091(5) 0.0037(5) C1 0.0219(7) 0.0170(6) 0.0277(7) 0.0041(5) 0.0071(6) 0.0011(5) C2 0.0189(7) 0.0175(6) 0.0177(6) 0.0010(4) 0.0021(5) 0.0002(5) C3 0.0239(7) 0.0176(6) 0.0240(6) -0.0023(5) 0.0074(6) -0.0002(5) C4 0.0258(8) 0.0158(6) 0.0260(6) -0.0012(5) 0.0074(6) -0.0025(5) C5 0.0179(7) 0.0184(6) 0.0203(6) 0.0016(5) 0.0030(5) -0.0003(5) C6 0.0207(7) 0.0181(6) 0.0229(6) 0.0007(5) 0.0046(5) -0.0011(5) C7 0.0217(7) 0.0181(6) 0.0224(6) 0.0000(5) 0.0060(5) -0.0016(5) C8 0.0230(8) 0.0368(9) 0.0294(7) 0.0006(6) 0.0042(6) -0.0005(7) C9 0.0333(9) 0.0258(8) 0.0246(7) -0.0030(6) 0.0064(6) -0.0072(6) C10 0.0384(10) 0.0227(7) 0.0286(7) 0.0041(6) 0.0135(7) 0.0004(6) C11 0.0220(7) 0.0216(7) 0.0198(6) 0.0000(5) 0.0026(5) 0.0013(5) C12 0.0236(8) 0.0201(7) 0.0252(7) -0.0012(5) 0.0047(6) 0.0026(6) C13 0.0234(8) 0.0122(6) 0.0255(6) -0.0010(5) 0.0057(5) 0.0027(5) C14 0.0222(7) 0.0152(6) 0.0284(7) 0.0010(5) 0.0093(6) 0.0019(5) C15 0.0174(7) 0.0166(6) 0.0320(7) -0.0013(5) 0.0066(6) 0.0008(5) _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 O1 C6 1.2189(15) . ? O2 C11 1.3156(15) . ? O3 C11 1.2171(16) . ? N1 C5 1.3402(16) . ? N1 C1 1.3428(16) . ? N2 C6 1.3814(16) . ? N2 C5 1.4011(15) . ? C1 C2 1.3884(18) . ? C2 C3 1.3972(19) . ? C2 C2 1.486(2) 3_765 ? C3 C4 1.3845(17) . ? C4 C5 1.3931(18) . ? C6 C7 1.5356(16) . ? C7 C8 1.527(2) . ? C7 C10 1.5358(19) . ? C7 C9 1.541(2) . ? C11 C12 1.5127(19) . ? C12 C13 1.514(2) . ? C13 C14 1.390(2) . ? C13 C15 1.4008(17) 3_575 ? C14 C15 1.388(2) . ? C15 C13 1.4008(17) 3_575 ? 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 C5 N1 C1 118.93(11) . . ? C6 N2 C5 125.57(11) . . ? N1 C1 C2 124.40(12) . . ? C1 C2 C3 115.36(11) . . ? C1 C2 C2 121.03(14) . 3_765 ? C3 C2 C2 123.62(14) . 3_765 ? C4 C3 C2 121.33(12) . . ? C3 C4 C5 118.48(12) . . ? N1 C5 C4 121.23(11) . . ? N1 C5 N2 113.79(11) . . ? C4 C5 N2 124.98(11) . . ? O1 C6 N2 121.80(11) . . ? O1 C6 C7 122.95(11) . . ? N2 C6 C7 115.24(11) . . ? C8 C7 C10 109.54(12) . . ? C8 C7 C6 110.03(11) . . ? C10 C7 C6 108.39(11) . . ? C8 C7 C9 110.63(12) . . ? C10 C7 C9 108.96(12) . . ? C6 C7 C9 109.26(11) . . ? O3 C11 O2 123.18(12) . . ? O3 C11 C12 123.61(12) . . ? O2 C11 C12 113.19(11) . . ? C11 C12 C13 109.88(11) . . ? C14 C13 C15 118.40(13) . 3_575 ? C14 C13 C12 121.07(11) . . ? C15 C13 C12 120.45(13) 3_575 . ? C15 C14 C13 121.06(12) . . ? C14 C15 C13 120.52(14) . 3_575 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 -0.9(2) . . . . ? N1 C1 C2 C3 4.3(2) . . . . ? N1 C1 C2 C2 -176.12(15) . . . 3_765 ? C1 C2 C3 C4 -2.9(2) . . . . ? C2 C2 C3 C4 177.51(15) 3_765 . . . ? C2 C3 C4 C5 -1.5(2) . . . . ? C1 N1 C5 C4 -4.0(2) . . . . ? C1 N1 C5 N2 175.12(12) . . . . ? C3 C4 C5 N1 5.2(2) . . . . ? C3 C4 C5 N2 -173.85(13) . . . . ? C6 N2 C5 N1 -156.17(13) . . . . ? C6 N2 C5 C4 22.9(2) . . . . ? C5 N2 C6 O1 -14.7(2) . . . . ? C5 N2 C6 C7 164.06(13) . . . . ? O1 C6 C7 C8 -114.88(16) . . . . ? N2 C6 C7 C8 66.33(16) . . . . ? O1 C6 C7 C10 4.9(2) . . . . ? N2 C6 C7 C10 -173.91(13) . . . . ? O1 C6 C7 C9 123.48(16) . . . . ? N2 C6 C7 C9 -55.31(16) . . . . ? O3 C11 C12 C13 -102.24(16) . . . . ? O2 C11 C12 C13 76.07(15) . . . . ? C11 C12 C13 C14 99.19(14) . . . . ? C11 C12 C13 C15 -77.61(16) . . . 3_575 ? C15 C13 C14 C15 1.1(2) 3_575 . . . ? C12 C13 C14 C15 -175.76(12) . . . . ? C13 C14 C15 C13 -1.1(2) . . . 3_575 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.81 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.377 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.056 # Attachment 'receptor_1_ccdc_cif.txt' data_spg376dm _database_code_depnum_ccdc_archive 'CCDC 646489' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Recognition of Dicarboxylic Acids by 3,3/-Bipyridine Amide Based Receptors and Its Supramolecular Behavior in the Solid State ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 N4 O2' _chemical_formula_weight 354.45 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P21/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.8375(1) _cell_length_b 15.9570(2) _cell_length_c 10.32990(1) _cell_angle_alpha 90.00 _cell_angle_beta 95.814(1) _cell_angle_gamma 90.00 _cell_volume 957.27(2) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 5012 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 31.37 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9577 _exptl_absorpt_correction_T_max 0.9949 _exptl_absorpt_process_details 'SADABS (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Brucker SMART APEX2 CCD diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24213 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 31.37 _reflns_number_total 3151 _reflns_number_gt 1922 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement APEX2 _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL and PLATON (Spek, 2003) ; _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^)+(0.0750P)^2^+0.1031P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3151 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0960 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1702 _refine_ls_wR_factor_gt 0.1495 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 O1 O 0.1526(2) 0.26497(8) 0.29355(10) 0.0635(4) Uani 1 1 d . . . N1 N -0.0766(2) 0.39566(9) 0.59934(12) 0.0600(4) Uani 1 1 d . . . N2 N 0.1055(2) 0.28819(8) 0.50478(11) 0.0488(3) Uani 1 1 d . . . C1 C -0.2433(3) 0.45288(11) 0.59867(14) 0.0566(4) Uani 1 1 d . . . C2 C -0.4058(2) 0.46916(8) 0.49555(12) 0.0439(3) Uani 1 1 d . . . C3 C -0.3781(4) 0.42433(12) 0.38409(16) 0.0752(6) Uani 1 1 d . . . C4 C -0.2041(3) 0.36678(12) 0.37985(16) 0.0703(6) Uani 1 1 d . . . C5 C -0.0607(2) 0.35247(8) 0.49193(12) 0.0437(3) Uani 1 1 d . . . C6 C 0.1919(2) 0.24425(9) 0.40736(13) 0.0454(3) Uani 1 1 d . . . C7 C 0.3324(2) 0.16640(10) 0.44907(14) 0.0504(4) Uani 1 1 d . . . C8 C 0.1641(4) 0.09960(15) 0.4870(4) 0.0953(9) Uani 1 1 d . . . C9 C 0.4568(5) 0.13630(17) 0.33406(19) 0.0844(7) Uani 1 1 d . . . C10 C 0.5122(3) 0.18375(15) 0.56349(18) 0.0658(5) Uani 1 1 d . . . H1N2 H 0.154(3) 0.2778(11) 0.5886(17) 0.062(5) Uiso 1 1 d . . . H1 H -0.245(3) 0.4838(12) 0.677(2) 0.072(5) Uiso 1 1 d . . . H9C H 0.550(4) 0.0863(15) 0.361(2) 0.097(7) Uiso 1 1 d . . . H10C H 0.611(4) 0.1356(13) 0.5841(19) 0.082(6) Uiso 1 1 d . . . H10B H 0.448(4) 0.2012(13) 0.642(2) 0.087(6) Uiso 1 1 d . . . H4 H -0.191(4) 0.3348(15) 0.306(2) 0.101(7) Uiso 1 1 d . . . H3 H -0.492(4) 0.4276(14) 0.316(2) 0.098(7) Uiso 1 1 d . . . H8B H 0.249(4) 0.0507(17) 0.504(2) 0.109(8) Uiso 1 1 d . . . H9B H 0.344(5) 0.1213(17) 0.256(3) 0.118(9) Uiso 1 1 d . . . H10A H 0.598(4) 0.2291(17) 0.541(2) 0.110(9) Uiso 1 1 d . . . H8A H 0.079(6) 0.1195(19) 0.556(3) 0.133(11) Uiso 1 1 d . . . H9A H 0.557(7) 0.188(2) 0.307(3) 0.181(15) Uiso 1 1 d . . . H8C H 0.058(5) 0.0902(17) 0.413(3) 0.123(10) 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 O1 0.0763(8) 0.0756(8) 0.0380(5) 0.0014(5) 0.0027(5) 0.0195(6) N1 0.0566(8) 0.0830(10) 0.0386(6) -0.0084(6) -0.0034(5) 0.0171(7) N2 0.0512(7) 0.0582(7) 0.0358(6) 0.0010(5) -0.0018(5) 0.0087(5) C1 0.0570(9) 0.0742(10) 0.0377(7) -0.0101(7) -0.0003(6) 0.0118(8) C2 0.0497(8) 0.0423(7) 0.0388(7) 0.0012(5) 0.0008(6) -0.0006(5) C3 0.0944(14) 0.0787(12) 0.0460(9) -0.0158(8) -0.0246(9) 0.0393(10) C4 0.0905(13) 0.0734(11) 0.0420(8) -0.0168(8) -0.0176(8) 0.0327(9) C5 0.0467(7) 0.0464(7) 0.0373(6) 0.0020(5) 0.0010(5) -0.0001(6) C6 0.0440(7) 0.0528(8) 0.0383(7) -0.0005(5) -0.0009(5) 0.0004(6) C7 0.0457(8) 0.0573(8) 0.0469(8) -0.0007(6) -0.0019(6) 0.0065(6) C8 0.0665(14) 0.0570(12) 0.161(3) 0.0169(14) 0.0030(16) -0.0010(10) C9 0.0979(16) 0.1002(16) 0.0534(10) -0.0075(10) -0.0009(10) 0.0508(14) C10 0.0544(10) 0.0899(14) 0.0503(9) 0.0033(9) -0.0084(7) 0.0119(10) _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 O1 C6 1.2204(17) . ? N1 C5 1.3174(18) . ? N1 C1 1.334(2) . ? N2 C6 1.3642(18) . ? N2 C5 1.4090(18) . ? C1 C2 1.377(2) . ? C2 C3 1.379(2) . ? C2 C2 1.486(3) 3_466 ? C3 C4 1.373(2) . ? C4 C5 1.377(2) . ? C6 C7 1.527(2) . ? C7 C10 1.524(2) . ? C7 C8 1.528(3) . ? C7 C9 1.531(2) . ? 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 C5 N1 C1 117.86(12) . . ? C6 N2 C5 127.38(12) . . ? N1 C1 C2 125.30(13) . . ? C1 C2 C3 114.71(14) . . ? C1 C2 C2 122.22(15) . 3_466 ? C3 C2 C2 123.06(15) . 3_466 ? C4 C3 C2 121.56(15) . . ? C3 C4 C5 118.20(14) . . ? N1 C5 C4 122.18(14) . . ? N1 C5 N2 114.08(12) . . ? C4 C5 N2 123.64(13) . . ? O1 C6 N2 121.60(13) . . ? O1 C6 C7 122.37(13) . . ? N2 C6 C7 115.99(12) . . ? C10 C7 C6 112.29(14) . . ? C10 C7 C8 109.76(19) . . ? C6 C7 C8 107.39(14) . . ? C10 C7 C9 108.36(16) . . ? C6 C7 C9 108.66(13) . . ? C8 C7 C9 110.4(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 2.0(3) . . . . ? N1 C1 C2 C3 -3.9(3) . . . . ? N1 C1 C2 C2 176.65(17) . . . 3_466 ? C1 C2 C3 C4 1.6(3) . . . . ? C2 C2 C3 C4 -178.9(2) 3_466 . . . ? C2 C3 C4 C5 2.2(3) . . . . ? C1 N1 C5 C4 2.3(3) . . . . ? C1 N1 C5 N2 -174.35(14) . . . . ? C3 C4 C5 N1 -4.3(3) . . . . ? C3 C4 C5 N2 172.01(17) . . . . ? C6 N2 C5 N1 -166.43(14) . . . . ? C6 N2 C5 C4 17.0(3) . . . . ? C5 N2 C6 O1 10.1(2) . . . . ? C5 N2 C6 C7 -167.85(13) . . . . ? O1 C6 C7 C10 133.90(17) . . . . ? N2 C6 C7 C10 -48.18(18) . . . . ? O1 C6 C7 C8 -105.3(2) . . . . ? N2 C6 C7 C8 72.6(2) . . . . ? O1 C6 C7 C9 14.1(2) . . . . ? N2 C6 C7 C9 -168.03(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 31.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.213 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.037