Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Valiyaveettil, Suresh' 'Hoong, Angelia Kar Min' 'Liu, Rong' 'Mok, K-F' _publ_contact_author_name 'Dr Suresh Valiyaveettil' _publ_contact_author_address ; Department of Chemistry National University of Singapore 3 Science Drive 3 173543 SINGAPORE ; _publ_contact_author_email CHMSV@NUS.EDU.SG _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; Solid-state Self-assembly of 1,4-Bis(2-carboxybenzyloxy)benzene in the Presence and Absence of Aromatic Amines ; data_diacid1 _database_code_CSD 164967 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 O6' _chemical_formula_weight 378.36 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' '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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.1936(2) _cell_length_b 7.24040(10) _cell_length_c 17.31980(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.1050(10) _cell_angle_gamma 90.00 _cell_volume 1894.51(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5866 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.0 _exptl_crystal_description 'rectangular shape, cut' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.5 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type 'sadabs (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.5604 _exptl_absorpt_correction_T_max 0.9610 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9897 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 26.36 _reflns_number_total 3765 _reflns_number_gt 2779 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS, SMART' _computing_cell_refinement 'Bruker AXS, SAINT' _computing_data_reduction 'Bruker AXS, SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS, SHELXTL' _computing_publication_material 'Bruker AXS, SHELXTL' _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^)+(0.0675P)^2^+0.2356P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0129(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3765 _refine_ls_number_parameters 324 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1296 _refine_ls_wR_factor_gt 0.1193 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.49483(10) 0.81455(19) 0.44279(8) 0.0738(4) Uani 1 1 d . . . O2 O 0.56912(11) 1.0753(2) 0.43035(9) 0.0750(5) Uani 1 1 d . . . H2 H 0.5458(12) 1.102(3) 0.4703(11) 0.050 Uiso 1 1 d . . . O3 O 0.47043(10) 0.40295(18) 0.27759(8) 0.0712(4) Uani 1 1 d . . . O4 O 0.45437(8) 0.14893(15) 0.17678(7) 0.0517(3) Uani 1 1 d . . . O5 O 0.49194(10) -0.30171(19) 0.03899(9) 0.0753(5) Uani 1 1 d . . . O6 O 0.38554(11) -0.4379(2) -0.03738(11) 0.0905(6) Uani 1 1 d . . . H6 H 0.4284(13) -0.520(3) -0.0385(10) 0.050 Uiso 1 1 d . . . C1 C 0.54351(12) 0.9116(2) 0.40700(11) 0.0536(4) Uani 1 1 d . . . C2 C 0.57783(11) 0.8489(2) 0.33431(10) 0.0493(4) Uani 1 1 d . . . C3 C 0.63774(14) 0.9614(3) 0.30121(12) 0.0622(5) Uani 1 1 d . . . H3 H 0.6530(14) 1.073(3) 0.3254(12) 0.070(6) Uiso 1 1 d . . . C4 C 0.67407(14) 0.9087(3) 0.23473(12) 0.0678(5) Uani 1 1 d . . . H4 H 0.7167(17) 0.987(3) 0.2140(13) 0.086(7) Uiso 1 1 d . . . C5 C 0.64954(13) 0.7416(3) 0.20044(12) 0.0635(5) Uani 1 1 d . . . H5 H 0.6735(14) 0.703(3) 0.1521(12) 0.072(6) Uiso 1 1 d . . . C6 C 0.58966(12) 0.6286(3) 0.23186(10) 0.0553(5) Uani 1 1 d . . . H6A H 0.5701(15) 0.509(3) 0.2083(13) 0.077(6) Uiso 1 1 d . . . C7 C 0.55178(11) 0.6784(2) 0.29899(9) 0.0475(4) Uani 1 1 d . . . C8 C 0.48455(13) 0.5537(2) 0.33020(11) 0.0533(4) Uani 1 1 d . . . H8A H 0.4268(13) 0.619(3) 0.3330(11) 0.058(5) Uiso 1 1 d . . . H8B H 0.5061(13) 0.508(3) 0.3822(12) 0.064(6) Uiso 1 1 d . . . C9 C 0.41193(12) 0.2679(2) 0.29289(10) 0.0498(4) Uani 1 1 d . . . C10 C 0.36390(14) 0.2601(3) 0.35621(11) 0.0604(5) Uani 1 1 d . . . H10 H 0.3716(13) 0.357(3) 0.3934(12) 0.066(6) Uiso 1 1 d . . . C11 C 0.30660(15) 0.1140(3) 0.36423(12) 0.0681(5) Uani 1 1 d . . . H11 H 0.2711(16) 0.109(3) 0.4081(14) 0.084(7) Uiso 1 1 d . . . C12 C 0.29775(15) -0.0226(3) 0.30950(13) 0.0710(6) Uani 1 1 d . . . H12 H 0.2585(16) -0.121(3) 0.3132(13) 0.085(7) Uiso 1 1 d . . . C13 C 0.34573(13) -0.0168(3) 0.24547(11) 0.0591(5) Uani 1 1 d . . . H13 H 0.3399(14) -0.113(3) 0.2081(13) 0.075(6) Uiso 1 1 d . . . C14 C 0.40331(11) 0.1266(2) 0.23721(9) 0.0456(4) Uani 1 1 d . . . C15 C 0.45550(12) 0.0005(3) 0.12207(10) 0.0502(4) Uani 1 1 d . . . H15A H 0.4610(12) -0.115(3) 0.1489(11) 0.057(5) Uiso 1 1 d . . . H15B H 0.5125(14) 0.020(3) 0.0982(11) 0.063(5) Uiso 1 1 d . . . C16 C 0.37573(11) 0.0044(2) 0.06125(9) 0.0453(4) Uani 1 1 d . . . C17 C 0.31908(13) 0.1554(3) 0.05697(11) 0.0581(5) Uani 1 1 d . . . H17 H 0.3322(12) 0.257(3) 0.0938(11) 0.058(5) Uiso 1 1 d . . . C18 C 0.24460(15) 0.1623(3) 0.00373(13) 0.0722(6) Uani 1 1 d . . . H18 H 0.2072(15) 0.262(3) 0.0040(13) 0.079(7) Uiso 1 1 d . . . C19 C 0.22464(15) 0.0177(3) -0.04654(13) 0.0715(6) Uani 1 1 d . . . H19 H 0.1720(18) 0.019(4) -0.0816(15) 0.103(8) Uiso 1 1 d . . . C20 C 0.28024(13) -0.1325(3) -0.04485(11) 0.0597(5) Uani 1 1 d . . . H20 H 0.2679(14) -0.234(3) -0.0794(12) 0.071(6) Uiso 1 1 d . . . C21 C 0.35599(11) -0.1414(2) 0.00824(9) 0.0464(4) Uani 1 1 d . . . C22 C 0.41696(12) -0.3004(2) 0.00540(10) 0.0509(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0946(11) 0.0625(8) 0.0680(9) -0.0297(7) 0.0262(8) -0.0254(8) O2 0.0874(10) 0.0665(9) 0.0747(9) -0.0378(8) 0.0247(8) -0.0255(7) O3 0.0957(10) 0.0564(8) 0.0657(8) -0.0315(7) 0.0279(7) -0.0260(7) O4 0.0606(7) 0.0445(6) 0.0515(7) -0.0171(5) 0.0124(5) -0.0060(5) O5 0.0708(9) 0.0623(8) 0.0887(10) -0.0376(7) -0.0112(8) 0.0187(7) O6 0.0810(11) 0.0628(9) 0.1203(14) -0.0485(9) -0.0233(9) 0.0173(8) C1 0.0529(10) 0.0490(10) 0.0573(10) -0.0181(8) -0.0009(8) -0.0076(8) C2 0.0479(9) 0.0494(9) 0.0493(9) -0.0112(8) -0.0015(7) -0.0006(8) C3 0.0622(11) 0.0607(12) 0.0629(11) -0.0148(10) 0.0028(9) -0.0114(9) C4 0.0635(12) 0.0784(14) 0.0621(12) -0.0067(11) 0.0104(10) -0.0150(11) C5 0.0590(11) 0.0789(13) 0.0531(11) -0.0131(10) 0.0081(9) 0.0011(10) C6 0.0563(10) 0.0563(10) 0.0521(10) -0.0131(8) 0.0000(8) 0.0043(9) C7 0.0481(9) 0.0464(9) 0.0461(9) -0.0099(7) -0.0040(7) 0.0050(7) C8 0.0628(12) 0.0451(9) 0.0515(10) -0.0185(8) 0.0043(8) -0.0031(8) C9 0.0554(10) 0.0437(9) 0.0502(9) -0.0110(7) 0.0050(7) -0.0025(8) C10 0.0729(13) 0.0587(11) 0.0508(10) -0.0129(9) 0.0124(9) 0.0031(10) C11 0.0722(13) 0.0762(14) 0.0591(11) -0.0008(10) 0.0212(10) -0.0019(11) C12 0.0752(14) 0.0689(13) 0.0702(13) -0.0008(11) 0.0143(11) -0.0222(11) C13 0.0696(12) 0.0513(10) 0.0566(10) -0.0103(9) 0.0071(9) -0.0124(9) C14 0.0476(9) 0.0438(8) 0.0452(9) -0.0071(7) 0.0032(7) 0.0032(7) C15 0.0560(11) 0.0441(9) 0.0504(10) -0.0153(8) 0.0051(8) 0.0035(8) C16 0.0516(9) 0.0428(8) 0.0423(8) -0.0051(7) 0.0095(7) 0.0031(7) C17 0.0659(12) 0.0514(10) 0.0573(11) -0.0084(9) 0.0076(9) 0.0141(9) C18 0.0701(13) 0.0740(14) 0.0713(13) -0.0014(11) 0.0025(10) 0.0285(11) C19 0.0618(13) 0.0866(15) 0.0630(12) -0.0023(11) -0.0072(10) 0.0120(11) C20 0.0626(11) 0.0649(11) 0.0503(10) -0.0097(9) -0.0006(8) -0.0007(9) C21 0.0539(9) 0.0444(8) 0.0418(8) -0.0053(7) 0.0087(7) 0.0010(7) C22 0.0611(11) 0.0456(9) 0.0457(9) -0.0127(7) 0.0041(8) -0.0003(8) _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 C1 1.234(2) . ? O2 C1 1.298(2) . ? O3 C9 1.366(2) . ? O3 C8 1.4235(19) . ? O4 C14 1.377(2) . ? O4 C15 1.4340(19) . ? O5 C22 1.223(2) . ? O6 C22 1.301(2) . ? C1 C2 1.484(2) . ? C2 C3 1.390(3) . ? C2 C7 1.416(2) . ? C3 C4 1.383(3) . ? C4 C5 1.381(3) . ? C5 C6 1.378(3) . ? C6 C7 1.398(2) . ? C7 C8 1.506(3) . ? C9 C10 1.382(3) . ? C9 C14 1.403(2) . ? C10 C11 1.386(3) . ? C11 C12 1.367(3) . ? C12 C13 1.391(3) . ? C13 C14 1.375(2) . ? C15 C16 1.519(2) . ? C16 C17 1.389(2) . ? C16 C21 1.410(2) . ? C17 C18 1.383(3) . ? C18 C19 1.375(3) . ? C19 C20 1.375(3) . ? C20 C21 1.396(3) . ? C21 C22 1.481(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 C9 O3 C8 118.79(14) . . ? C14 O4 C15 117.48(13) . . ? O1 C1 O2 122.62(17) . . ? O1 C1 C2 122.36(15) . . ? O2 C1 C2 115.02(17) . . ? C3 C2 C7 119.89(16) . . ? C3 C2 C1 118.37(16) . . ? C7 C2 C1 121.75(16) . . ? C4 C3 C2 121.24(19) . . ? C5 C4 C3 119.1(2) . . ? C6 C5 C4 120.62(18) . . ? C5 C6 C7 121.55(18) . . ? C6 C7 C2 117.58(17) . . ? C6 C7 C8 119.95(15) . . ? C2 C7 C8 122.47(15) . . ? O3 C8 C7 106.96(14) . . ? O3 C9 C10 126.35(15) . . ? O3 C9 C14 113.83(15) . . ? C10 C9 C14 119.82(16) . . ? C9 C10 C11 120.06(18) . . ? C12 C11 C10 119.96(19) . . ? C11 C12 C13 120.65(19) . . ? C14 C13 C12 119.94(18) . . ? C13 C14 O4 125.74(15) . . ? C13 C14 C9 119.56(16) . . ? O4 C14 C9 114.69(14) . . ? O4 C15 C16 112.32(14) . . ? C17 C16 C21 117.84(16) . . ? C17 C16 C15 119.71(15) . . ? C21 C16 C15 122.44(14) . . ? C18 C17 C16 121.53(18) . . ? C19 C18 C17 120.29(19) . . ? C18 C19 C20 119.7(2) . . ? C19 C20 C21 120.81(18) . . ? C20 C21 C16 119.84(16) . . ? C20 C21 C22 119.25(15) . . ? C16 C21 C22 120.84(15) . . ? O5 C22 O6 122.11(16) . . ? O5 C22 C21 123.00(15) . . ? O6 C22 C21 114.87(16) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.259 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.034 data_1.bipy _database_code_CSD 164968 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H26 N2 O6' _chemical_formula_weight 534.55 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 6.1009(7) _cell_length_b 8.0739(9) _cell_length_c 13.4904(15) _cell_angle_alpha 83.523(2) _cell_angle_beta 80.3840(10) _cell_angle_gamma 87.233(2) _cell_volume 650.70(13) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1696 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.0 _exptl_crystal_description 'thin plates' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type 'sadabs (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.0837 _exptl_absorpt_correction_T_max 0.9467 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4072 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2441 _reflns_number_gt 1582 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS, SMART' _computing_cell_refinement 'Bruker AXS, SAINT' _computing_data_reduction 'Bruker AXS, SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS, SHELXTL' _computing_publication_material 'Bruker AXS, SHELXTL' _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^)+(0.0746P)^2^+0.0485P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.043(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2441 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0887 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1480 _refine_ls_wR_factor_gt 0.1300 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 -0.1566(3) 0.3332(2) 0.33224(13) 0.0669(5) Uani 1 1 d . . . H1 H -0.206(5) 0.440(4) 0.358(2) 0.100(10) Uiso 1 1 d . . . O2 O 0.1552(3) 0.4649(2) 0.27436(15) 0.0729(5) Uani 1 1 d . . . O3 O 0.6852(3) 0.2694(2) 0.08550(13) 0.0654(5) Uani 1 1 d . . . N1 N -0.3102(3) 0.6166(2) 0.40629(15) 0.0622(6) Uani 1 1 d . . . C1 C -0.2030(5) 0.6895(3) 0.4662(2) 0.0840(9) Uani 1 1 d . . . H1A H -0.0730 0.6375 0.4832 0.101 Uiso 1 1 calc R . . C2 C -0.2714(5) 0.8368(3) 0.5048(2) 0.0768(8) Uani 1 1 d . . . H2 H -0.1897 0.8807 0.5474 0.092 Uiso 1 1 calc R . . C3 C -0.4602(3) 0.9194(3) 0.48057(14) 0.0462(5) Uani 1 1 d . . . C4 C -0.5685(4) 0.8455(3) 0.4158(2) 0.0683(7) Uani 1 1 d . . . H4 H -0.6956 0.8971 0.3953 0.082 Uiso 1 1 calc R . . C5 C -0.4906(4) 0.6968(3) 0.3815(2) 0.0724(8) Uani 1 1 d . . . H5 H -0.5687 0.6499 0.3386 0.087 Uiso 1 1 calc R . . C6 C 0.0472(4) 0.3417(3) 0.28101(15) 0.0480(5) Uani 1 1 d . . . C7 C 0.1287(3) 0.1850(3) 0.23639(14) 0.0427(5) Uani 1 1 d . . . C8 C -0.0085(4) 0.0485(3) 0.25383(16) 0.0529(6) Uani 1 1 d . . . H8 H -0.1498 0.0578 0.2917 0.063 Uiso 1 1 calc R . . C9 C 0.0610(4) -0.1002(3) 0.21606(18) 0.0624(7) Uani 1 1 d . . . H9 H -0.0323 -0.1905 0.2287 0.075 Uiso 1 1 calc R . . C10 C 0.2683(4) -0.1139(3) 0.15990(18) 0.0625(7) Uani 1 1 d . . . H10 H 0.3165 -0.2142 0.1345 0.075 Uiso 1 1 calc R . . C11 C 0.4061(4) 0.0204(3) 0.14079(17) 0.0557(6) Uani 1 1 d . . . H11 H 0.5463 0.0091 0.1022 0.067 Uiso 1 1 calc R . . C12 C 0.3412(3) 0.1718(3) 0.17754(14) 0.0441(5) Uani 1 1 d . . . C13 C 0.4911(3) 0.3188(3) 0.15123(16) 0.0507(6) Uani 1 1 d . . . H13A H 0.4150 0.4118 0.1180 0.061 Uiso 1 1 calc R . . H13B H 0.5316 0.3533 0.2121 0.061 Uiso 1 1 calc R . . C14 C 0.8370(3) 0.3893(3) 0.04588(16) 0.0504(6) Uani 1 1 d . . . C15 C 0.8097(4) 0.5567(3) 0.05861(16) 0.0550(6) Uani 1 1 d . . . H15 H 0.6822 0.5956 0.0982 0.066 Uiso 1 1 calc R . . C16 C 0.9717(4) 0.6665(3) 0.01250(17) 0.0552(6) Uani 1 1 d . . . H16 H 0.9518 0.7793 0.0208 0.066 Uiso 1 1 calc R . . 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 0.0583(10) 0.0585(11) 0.0810(11) -0.0271(9) 0.0108(8) -0.0036(8) O2 0.0655(11) 0.0526(11) 0.1007(13) -0.0293(9) 0.0029(9) -0.0101(9) O3 0.0536(10) 0.0599(11) 0.0774(11) -0.0153(8) 0.0126(8) -0.0109(8) N1 0.0690(13) 0.0509(12) 0.0645(12) -0.0176(10) 0.0016(10) 0.0048(10) C1 0.096(2) 0.0682(19) 0.098(2) -0.0320(16) -0.0413(17) 0.0343(16) C2 0.093(2) 0.0691(18) 0.0798(17) -0.0323(14) -0.0408(15) 0.0301(15) C3 0.0498(12) 0.0433(13) 0.0427(11) -0.0063(9) 0.0007(9) 0.0013(10) C4 0.0570(15) 0.0646(17) 0.0917(18) -0.0336(14) -0.0227(13) 0.0112(12) C5 0.0666(17) 0.0687(18) 0.0894(19) -0.0364(15) -0.0177(14) 0.0052(14) C6 0.0502(13) 0.0491(14) 0.0461(11) -0.0112(10) -0.0073(9) -0.0010(11) C7 0.0470(12) 0.0424(12) 0.0397(10) -0.0063(9) -0.0080(9) -0.0028(9) C8 0.0516(13) 0.0530(14) 0.0527(12) -0.0117(11) 0.0013(10) -0.0077(11) C9 0.0706(16) 0.0500(15) 0.0669(15) -0.0159(12) -0.0026(12) -0.0134(12) C10 0.0688(16) 0.0485(15) 0.0703(15) -0.0225(12) -0.0009(12) -0.0011(12) C11 0.0532(13) 0.0575(15) 0.0555(13) -0.0164(11) 0.0007(10) -0.0016(11) C12 0.0456(12) 0.0469(13) 0.0409(10) -0.0075(9) -0.0075(9) -0.0030(10) C13 0.0444(12) 0.0537(14) 0.0529(12) -0.0097(10) -0.0007(9) -0.0053(10) C14 0.0431(12) 0.0575(15) 0.0505(12) -0.0078(10) -0.0041(9) -0.0083(10) C15 0.0433(12) 0.0621(16) 0.0573(13) -0.0129(11) 0.0029(10) -0.0037(11) C16 0.0523(13) 0.0518(14) 0.0614(13) -0.0128(11) -0.0036(11) -0.0032(11) _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 1.318(3) . ? O2 C6 1.207(3) . ? O3 C14 1.373(3) . ? O3 C13 1.425(2) . ? N1 C1 1.322(3) . ? N1 C5 1.322(3) . ? C1 C2 1.371(3) . ? C2 C3 1.371(3) . ? C3 C4 1.379(3) . ? C3 C3 1.488(4) 2_476 ? C4 C5 1.371(3) . ? C6 C7 1.490(3) . ? C7 C8 1.392(3) . ? C7 C12 1.409(3) . ? C8 C9 1.377(3) . ? C9 C10 1.368(3) . ? C10 C11 1.379(3) . ? C11 C12 1.386(3) . ? C12 C13 1.507(3) . ? C14 C15 1.381(3) . ? C14 C16 1.381(3) 2_765 ? C15 C16 1.380(3) . ? C16 C14 1.381(3) 2_765 ? 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 C14 O3 C13 117.61(17) . . ? C1 N1 C5 116.0(2) . . ? N1 C1 C2 124.2(2) . . ? C1 C2 C3 120.1(2) . . ? C2 C3 C4 115.7(2) . . ? C2 C3 C3 122.2(2) . 2_476 ? C4 C3 C3 122.1(2) . 2_476 ? C5 C4 C3 120.6(2) . . ? N1 C5 C4 123.4(2) . . ? O2 C6 O1 121.8(2) . . ? O2 C6 C7 124.6(2) . . ? O1 C6 C7 113.6(2) . . ? C8 C7 C12 119.39(19) . . ? C8 C7 C6 119.00(19) . . ? C12 C7 C6 121.61(19) . . ? C9 C8 C7 121.2(2) . . ? C10 C9 C8 119.5(2) . . ? C9 C10 C11 120.2(2) . . ? C10 C11 C12 121.7(2) . . ? C11 C12 C7 117.9(2) . . ? C11 C12 C13 120.50(18) . . ? C7 C12 C13 121.54(18) . . ? O3 C13 C12 108.09(17) . . ? O3 C14 C15 125.25(19) . . ? O3 C14 C16 115.5(2) . 2_765 ? C15 C14 C16 119.2(2) . 2_765 ? C16 C15 C14 120.0(2) . . ? C15 C16 C14 120.8(2) . 2_765 ? _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.916 _refine_diff_density_max 0.234 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.041 data_197 _database_code_CSD 164969 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H28 N2 O6' _chemical_formula_weight 560.58 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 P2(1)/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 8.9416(11) _cell_length_b 8.1164(10) _cell_length_c 18.832(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.627(3) _cell_angle_gamma 90.00 _cell_volume 1366.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 1846 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 23.5 _exptl_crystal_description 'distorted hexagonal block' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 588 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.6814 _exptl_absorpt_correction_T_max 0.9424 _exptl_absorpt_process_details 'sadabs (Sheldrick, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 ? _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7674 _diffrn_reflns_av_R_equivalents 0.1267 _diffrn_reflns_av_sigmaI/netI 0.0859 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2408 _reflns_number_gt 1702 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS, SMART' _computing_cell_refinement 'Bruker AXS, SAINT' _computing_data_reduction 'Bruker AXS, SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS, SHELXTL' _computing_publication_material 'Bruker AXS, SHELXTL' _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^)+(0.1200P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2408 _refine_ls_number_parameters 217 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.0969 _refine_ls_R_factor_gt 0.0808 _refine_ls_wR_factor_ref 0.2080 _refine_ls_wR_factor_gt 0.1985 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.025 _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 0.2968(2) 0.2097(3) 0.33875(9) 0.0535(6) Uani 1 1 d . . . H1 H 0.3206 0.3007 0.3557 0.088(13) Uiso 1 1 calc R . . O2 O 0.2805(3) 0.3533(2) 0.23810(11) 0.0610(7) Uani 1 1 d . . . O3 O 0.1043(2) 0.2406(2) 0.08287(9) 0.0487(6) Uani 1 1 d . . . N1 N 0.3563(9) 0.4861(6) 0.4063(3) 0.043(4) Uani 0.696(13) 1 d PD A 1 C1 C 0.2941(8) 0.5334(9) 0.4657(3) 0.044(3) Uani 0.696(13) 1 d PD A 1 H1A H 0.2230 0.4623 0.4850 0.052 Uiso 0.696(13) 1 calc PR A 1 C2 C 0.3237(7) 0.6757(7) 0.5013(3) 0.0469(13) Uani 0.696(13) 1 d PD A 1 H2 H 0.2731 0.7012 0.5429 0.056 Uiso 0.696(13) 1 calc PR A 1 C3 C 0.4297(6) 0.7827(5) 0.4753(3) 0.0378(12) Uani 0.696(13) 1 d PD A 1 C4 C 0.4998(6) 0.7337(6) 0.4139(4) 0.0435(13) Uani 0.696(13) 1 d PD A 1 H4 H 0.5745 0.7991 0.3939 0.052 Uiso 0.696(13) 1 calc PR A 1 C5 C 0.4572(8) 0.5878(7) 0.3833(4) 0.0503(17) Uani 0.696(13) 1 d PD A 1 H5 H 0.5053 0.5576 0.3415 0.060 Uiso 0.696(13) 1 calc PR A 1 C6 C 0.4621(5) 0.9379(5) 0.5115(2) 0.0445(16) Uani 0.696(13) 1 d PD . 1 H6 H 0.4234 0.9493 0.5571 0.053 Uiso 0.696(13) 1 calc PR A 1 N1A N 0.3659(18) 0.4806(13) 0.4088(8) 0.059(12) Uiso 0.304(13) 1 d PG A 2 C1A C 0.4738(14) 0.5618(13) 0.3702(6) 0.033(4) Uiso 0.304(13) 1 d PG A 2 H1A1 H 0.5133 0.5115 0.3298 0.039 Uiso 0.304(13) 1 calc PR A 2 C2A C 0.5231(10) 0.7172(12) 0.3912(5) 0.041(4) Uiso 0.304(13) 1 d PGD A 2 H2A H 0.5960 0.7720 0.3650 0.050 Uiso 0.304(13) 1 calc PR A 2 C3A C 0.4645(10) 0.7915(9) 0.4508(6) 0.027(3) Uiso 0.304(13) 1 d PGD A 2 C4A C 0.3567(12) 0.7104(13) 0.4894(6) 0.038(4) Uiso 0.304(13) 1 d PGD A 2 H4A H 0.3172 0.7606 0.5298 0.045 Uiso 0.304(13) 1 calc PR A 2 C5A C 0.3074(16) 0.5549(15) 0.4684(8) 0.074(12) Uiso 0.304(13) 1 d PG A 2 H5A H 0.2345 0.5001 0.4946 0.088 Uiso 0.304(13) 1 calc PR A 2 C6A C 0.5198(11) 0.9558(12) 0.4715(6) 0.043(4) Uiso 0.304(13) 1 d PD . 2 H6A H 0.5902 1.0042 0.4418 0.051 Uiso 0.304(13) 1 calc PR A 2 C7 C 0.2675(3) 0.2254(3) 0.27049(14) 0.0414(7) Uani 1 1 d . . . C8 C 0.2199(3) 0.0663(3) 0.23621(13) 0.0374(6) Uani 1 1 d . . . C9 C 0.2869(3) -0.0790(3) 0.26155(15) 0.0454(7) Uani 1 1 d . . . H9 H 0.3561 -0.0739 0.3000 0.039(7) Uiso 1 1 calc R . . C10 C 0.2533(4) -0.2289(3) 0.23117(15) 0.0515(8) Uani 1 1 d . . . H10 H 0.3025 -0.3248 0.2473 0.063(9) Uiso 1 1 calc R . . C11 C 0.1472(4) -0.2377(3) 0.17709(17) 0.0545(8) Uani 1 1 d . . . H11 H 0.1216 -0.3403 0.1570 0.066(9) Uiso 1 1 calc R . . C12 C 0.0781(3) -0.0958(4) 0.15216(15) 0.0506(8) Uani 1 1 d . . . H12 H 0.0049 -0.1032 0.1155 0.047(8) Uiso 1 1 calc R . . C13 C 0.1150(3) 0.0583(3) 0.18055(13) 0.0410(7) Uani 1 1 d . . . C14 C 0.0354(3) 0.2064(3) 0.14929(14) 0.0444(7) Uani 1 1 d . . . H14A H -0.0713 0.1828 0.1416 0.056(8) Uiso 1 1 calc R . . H14B H 0.0459 0.3011 0.1813 0.047(7) Uiso 1 1 calc R . . C15 C 0.0470(3) 0.3718(3) 0.04376(12) 0.0377(6) Uani 1 1 d . . . C16 C 0.1157(3) 0.4008(3) -0.02023(13) 0.0392(6) Uani 1 1 d . . . H16 H 0.1952 0.3332 -0.0339 0.033(6) Uiso 1 1 calc R . . C17 C 0.0682(3) 0.5285(3) -0.06402(13) 0.0399(7) Uani 1 1 d . . . H17 H 0.1146 0.5468 -0.1075 0.054(8) Uiso 1 1 calc R . . 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 0.0858(16) 0.0362(13) 0.0383(11) -0.0007(8) -0.0040(10) -0.0124(10) O2 0.1003(17) 0.0293(12) 0.0530(12) 0.0063(9) -0.0019(11) -0.0117(10) O3 0.0606(13) 0.0432(12) 0.0427(11) 0.0081(8) 0.0093(9) 0.0159(9) N1 0.064(5) 0.026(3) 0.038(4) -0.0033(14) -0.012(2) -0.0049(16) C1 0.059(4) 0.032(3) 0.040(3) -0.0046(18) -0.0043(19) -0.009(2) C2 0.065(3) 0.035(3) 0.041(2) -0.006(2) 0.007(2) -0.014(3) C3 0.045(3) 0.036(2) 0.033(2) 0.0003(18) 0.002(2) -0.0038(19) C4 0.046(3) 0.039(3) 0.046(3) 0.000(2) 0.009(2) -0.0055(18) C5 0.068(4) 0.038(3) 0.046(3) -0.012(2) 0.011(2) 0.009(2) C6 0.052(3) 0.038(3) 0.044(3) -0.0051(17) -0.0019(18) -0.0046(17) C7 0.0529(16) 0.0288(15) 0.0425(14) -0.0013(11) -0.0002(11) -0.0016(11) C8 0.0527(16) 0.0242(14) 0.0354(13) 0.0006(10) 0.0046(11) -0.0012(11) C9 0.0627(18) 0.0306(16) 0.0428(15) 0.0043(12) -0.0008(12) 0.0011(13) C10 0.081(2) 0.0239(15) 0.0495(16) 0.0042(12) 0.0063(15) 0.0043(13) C11 0.083(2) 0.0252(16) 0.0558(17) -0.0056(13) 0.0082(15) -0.0079(14) C12 0.0645(19) 0.0408(17) 0.0462(16) -0.0055(13) -0.0029(13) -0.0081(13) C13 0.0556(17) 0.0293(15) 0.0383(13) 0.0016(11) 0.0069(11) 0.0007(12) C14 0.0560(18) 0.0384(16) 0.0388(14) 0.0021(12) 0.0014(11) 0.0058(12) C15 0.0464(15) 0.0300(14) 0.0365(13) -0.0011(10) -0.0037(10) 0.0025(11) C16 0.0434(15) 0.0342(15) 0.0400(13) -0.0048(11) 0.0034(11) 0.0072(12) C17 0.0496(16) 0.0366(15) 0.0337(13) -0.0009(11) 0.0024(11) 0.0019(12) _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 C7 1.311(3) . ? O2 C7 1.211(3) . ? O3 C15 1.384(3) . ? O3 C14 1.437(3) . ? N1 C5 1.306(5) . ? N1 C1 1.320(5) . ? C1 C2 1.358(8) . ? C2 C3 1.385(7) . ? C3 C4 1.389(7) . ? C3 C6 1.457(5) . ? C4 C5 1.366(7) . ? C6 C6 1.296(10) 3_676 ? N1A C1A 1.3900 . ? N1A C5A 1.3900 . ? C1A C2A 1.3900 . ? C2A C3A 1.3900 . ? C3A C4A 1.3900 . ? C3A C6A 1.471(9) . ? C4A C5A 1.3900 . ? C6A C6A 1.35(2) 3_676 ? C7 C8 1.500(3) . ? C8 C13 1.388(4) . ? C8 C9 1.401(4) . ? C9 C10 1.374(4) . ? C10 C11 1.374(5) . ? C11 C12 1.383(4) . ? C12 C13 1.396(4) . ? C13 C14 1.508(4) . ? C15 C17 1.373(4) 3_565 ? C15 C16 1.388(4) . ? C16 C17 1.383(4) . ? C17 C15 1.373(4) 3_565 ? 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 C15 O3 C14 116.79(19) . . ? C5 N1 C1 114.1(6) . . ? N1 C1 C2 125.8(6) . . ? C1 C2 C3 119.0(5) . . ? C2 C3 C4 116.3(3) . . ? C2 C3 C6 120.4(5) . . ? C4 C3 C6 123.3(5) . . ? C5 C4 C3 118.2(4) . . ? N1 C5 C4 126.5(6) . . ? C6 C6 C3 127.9(5) 3_676 . ? C1A N1A C5A 120.0 . . ? C2A C1A N1A 120.0 . . ? C1A C2A C3A 120.0 . . ? C4A C3A C2A 120.0 . . ? C4A C3A C6A 121.6(6) . . ? C2A C3A C6A 118.4(6) . . ? C5A C4A C3A 120.0 . . ? C4A C5A N1A 120.0 . . ? C6A C6A C3A 126.8(11) 3_676 . ? O2 C7 O1 123.9(2) . . ? O2 C7 C8 123.5(2) . . ? O1 C7 C8 112.6(2) . . ? C13 C8 C9 119.4(2) . . ? C13 C8 C7 122.9(2) . . ? C9 C8 C7 117.7(2) . . ? C10 C9 C8 121.1(3) . . ? C11 C10 C9 119.5(3) . . ? C10 C11 C12 120.1(3) . . ? C11 C12 C13 121.2(3) . . ? C8 C13 C12 118.6(2) . . ? C8 C13 C14 124.0(2) . . ? C12 C13 C14 117.4(2) . . ? O3 C14 C13 106.5(2) . . ? C17 C15 O3 125.1(2) 3_565 . ? C17 C15 C16 119.7(2) 3_565 . ? O3 C15 C16 115.3(2) . . ? C17 C16 C15 120.6(2) . . ? C15 C17 C16 119.8(2) 3_565 . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.346 _refine_diff_density_min -0.440 _refine_diff_density_rms 0.078