# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Kaftory, Menahem' _publ_contact_author_name 'Kaftory, Menahem' _publ_contact_author_email kaftory@tx.technion.ac.il _publ_section_title ; Formation of different photodimers of isoquinolinone by irradiation of solid molecular compounds ; # Attachment '1.cif' data_Isoquinolin-3(2H)-one _database_code_depnum_ccdc_archive 'CCDC 787295' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Isoquinolin-3(2H)-one ; _chemical_name_common isoquinolinone _chemical_melting_point ? _chemical_formula_moiety 'C9 H7 N O' _chemical_formula_sum 'C9 H7 N O' _chemical_formula_weight 145.16 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' O O 0.0106 0.0060 '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' _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 9.868(2) _cell_length_b 6.0890(10) _cell_length_c 12.466(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.14(3) _cell_angle_gamma 90.00 _cell_volume 711.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4352 _diffrn_reflns_av_R_equivalents 0.0671 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1258 _reflns_number_gt 950 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1282P)^2^+0.0704P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1244 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0816 _refine_ls_R_factor_gt 0.0661 _refine_ls_wR_factor_ref 0.2018 _refine_ls_wR_factor_gt 0.1917 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _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 O11 O 0.09287(18) 0.9376(3) -0.10159(13) 0.0639(6) Uani 1 1 d . . . H1O1 H 0.0337 1.0115 -0.0838 0.077 Uiso 0.50 1 calc PR . . N1 N 0.08597(17) 0.7660(3) 0.06018(14) 0.0473(6) Uani 1 1 d . . . H1N1 H 0.0244 0.8610 0.0665 0.057 Uiso 0.50 1 calc PR . . C1 C 0.1385(2) 0.7793(4) -0.02811(17) 0.0471(6) Uani 1 1 d . . . C2 C 0.2371(2) 0.6260(4) -0.03941(17) 0.0511(7) Uani 1 1 d . . . H2 H 0.2728 0.6346 -0.1001 0.061 Uiso 1 1 calc R . . C3 C 0.2829(2) 0.4578(4) 0.04061(16) 0.0442(6) Uani 1 1 d . . . C4 C 0.3845(2) 0.2971(4) 0.03511(18) 0.0532(7) Uani 1 1 d . . . H4 H 0.4233 0.3003 -0.0240 0.064 Uiso 1 1 calc R . . C5 C 0.4258(3) 0.1388(4) 0.11517(19) 0.0578(7) Uani 1 1 d . . . H5 H 0.4936 0.0361 0.1107 0.069 Uiso 1 1 calc R . . C6 C 0.3676(3) 0.1268(4) 0.20525(19) 0.0594(7) Uani 1 1 d . . . H6 H 0.3962 0.0154 0.2586 0.071 Uiso 1 1 calc R . . C7 C 0.2707(2) 0.2762(4) 0.21421(19) 0.0542(7) Uani 1 1 d . . . H7 H 0.2333 0.2684 0.2740 0.065 Uiso 1 1 calc R . . C8 C 0.2257(2) 0.4460(4) 0.13213(16) 0.0448(6) Uani 1 1 d . . . C9 C 0.1285(2) 0.6077(4) 0.13733(17) 0.0500(6) Uani 1 1 d . . . H9 H 0.0914 0.6054 0.1974 0.060 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 O11 0.0704(11) 0.0770(13) 0.0548(10) 0.0196(8) 0.0346(8) 0.0265(9) N1 0.0427(10) 0.0566(12) 0.0438(10) 0.0000(8) 0.0154(8) 0.0065(8) C1 0.0457(12) 0.0575(14) 0.0405(11) 0.0040(9) 0.0168(9) 0.0041(10) C2 0.0485(12) 0.0654(15) 0.0433(12) 0.0010(10) 0.0201(10) 0.0078(10) C3 0.0423(11) 0.0507(13) 0.0380(10) -0.0056(9) 0.0100(8) -0.0009(9) C4 0.0569(13) 0.0608(15) 0.0434(12) -0.0064(10) 0.0176(10) 0.0078(10) C5 0.0596(14) 0.0543(15) 0.0562(14) -0.0055(11) 0.0134(11) 0.0126(11) C6 0.0639(15) 0.0564(16) 0.0536(14) 0.0094(11) 0.0123(11) 0.0069(11) C7 0.0566(13) 0.0623(15) 0.0438(12) 0.0054(10) 0.0160(10) -0.0009(11) C8 0.0411(11) 0.0520(13) 0.0393(11) -0.0042(9) 0.0095(8) -0.0019(9) C9 0.0465(12) 0.0650(15) 0.0419(11) -0.0034(10) 0.0187(9) 0.0005(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 O11 C1 1.310(3) . ? O11 H1O1 0.8200 . ? N1 C9 1.334(3) . ? N1 C1 1.357(3) . ? N1 H1N1 0.8600 . ? C1 C2 1.387(3) . ? C2 C3 1.402(3) . ? C2 H2 0.9300 . ? C3 C4 1.418(3) . ? C3 C8 1.424(3) . ? C4 C5 1.356(3) . ? C4 H4 0.9300 . ? C5 C6 1.413(3) . ? C5 H5 0.9300 . ? C6 C7 1.350(3) . ? C6 H6 0.9300 . ? C7 C8 1.424(3) . ? C7 H7 0.9300 . ? C8 C9 1.391(3) . ? C9 H9 0.9300 . ? 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 C1 O11 H1O1 109.5 . . ? C9 N1 C1 120.95(17) . . ? C9 N1 H1N1 119.5 . . ? C1 N1 H1N1 119.5 . . ? O11 C1 N1 118.45(18) . . ? O11 C1 C2 121.59(18) . . ? N1 C1 C2 119.96(19) . . ? C1 C2 C3 120.0(2) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C2 C3 C4 123.1(2) . . ? C2 C3 C8 119.12(19) . . ? C4 C3 C8 117.8(2) . . ? C5 C4 C3 120.6(2) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 121.2(2) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C7 C6 C5 120.3(2) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.0(2) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C3 116.93(19) . . ? C9 C8 C7 123.1(2) . . ? C3 C8 C7 119.97(19) . . ? N1 C9 C8 123.02(18) . . ? N1 C9 H9 118.5 . . ? C8 C9 H9 118.5 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.449 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.054 # Attachment '1d.cif' data_pyridacetate _database_code_depnum_ccdc_archive 'CCDC 787296' #TrackingRef '1d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H14 N2 O2, 2(C2 H4 O2)' _chemical_formula_sum 'C22 H22 N2 O6' _chemical_formula_weight 410.42 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' N N 0.0061 0.0033 '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 7.102(6) _cell_length_b 7.909(6) _cell_length_c 9.350(5) _cell_angle_alpha 97.37(3) _cell_angle_beta 95.76(3) _cell_angle_gamma 101.14(3) _cell_volume 506.8(6) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 216 _exptl_absorpt_coefficient_mu 0.10 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Kappa CCD' _diffrn_measurement_method 'phi scan & omega scan' _diffrn_detector_area_resol_mean 95 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 5330 _diffrn_reflns_av_R_equivalents 0.053 _diffrn_reflns_av_sigmaI/netI 0.0813 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 26.54 _reflns_number_total 1905 _reflns_number_gt 1032 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2000)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0951P)^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 1905 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1120 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1451 _refine_ls_wR_factor_gt 0.1205 _refine_ls_goodness_of_fit_ref 0.817 _refine_ls_restrained_S_all 0.817 _refine_ls_shift/su_max 0.006 _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 -0.4245(2) 0.3927(2) 0.34442(18) 0.0523(5) Uani 1 1 d . . . O2 O 0.8230(3) 0.7558(3) -0.1122(2) 0.0766(7) Uani 1 1 d . . . C2 C -0.0801(3) 0.4427(3) 0.3317(2) 0.0377(6) Uani 1 1 d . . . H2 H -0.1205 0.3834 0.2316 0.045 Uiso 1 1 calc R . . C1 C -0.2577(3) 0.4742(3) 0.3985(2) 0.0371(6) Uani 1 1 d . . . C3 C 0.0520(3) 0.6173(3) 0.3286(2) 0.0382(6) Uani 1 1 d . . . O3 O 0.5239(3) 0.7700(3) -0.0747(2) 0.0762(7) Uani 1 1 d . . . H3 H 0.488(4) 0.694(4) -0.175(3) 0.091 Uiso 1 1 d . . . N1 N -0.2251(3) 0.5928(2) 0.5176(2) 0.0393(5) Uani 1 1 d . . . H1 H -0.331(4) 0.619(3) 0.588(2) 0.047 Uiso 1 1 d . . . C9 C -0.0268(3) 0.6787(3) 0.5793(2) 0.0365(6) Uani 1 1 d . . . H9 H -0.0327 0.7828 0.6465 0.044 Uiso 1 1 calc R . . C8 C 0.0810(3) 0.7379(3) 0.4559(2) 0.0383(6) Uani 1 1 d . . . C7 C 0.2025(3) 0.8984(3) 0.4641(3) 0.0453(6) Uani 1 1 d . . . H7 H 0.2225 0.9786 0.5489 0.054 Uiso 1 1 d R . . C5 C 0.2663(4) 0.8212(3) 0.2205(3) 0.0534(7) Uani 1 1 d . . . H5 H 0.3285 0.8498 0.1413 0.064 Uiso 1 1 calc R . . C4 C 0.1447(3) 0.6596(3) 0.2113(3) 0.0463(6) Uani 1 1 d . . . H4 H 0.1256 0.5799 0.1263 0.056 Uiso 1 1 calc R . . C6 C 0.2958(4) 0.9396(3) 0.3458(3) 0.0514(7) Uani 1 1 d . . . H6 H 0.3785 1.0476 0.3513 0.062 Uiso 1 1 calc R . . C10 C 0.7135(4) 0.7997(4) -0.0332(3) 0.0584(7) Uani 1 1 d . . . C11 C 0.7717(5) 0.9000(5) 0.1159(3) 0.0833(11) Uani 1 1 d . . . H11A H 0.6942 0.9861 0.1312 0.100 Uiso 1 1 calc R . . H11B H 0.9057 0.9567 0.1265 0.100 Uiso 1 1 calc R . . H11C H 0.7525 0.8220 0.1863 0.100 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 0.0332(11) 0.0660(11) 0.0508(10) -0.0058(8) 0.0031(8) 0.0039(8) O2 0.0678(14) 0.0898(15) 0.0732(14) -0.0069(11) 0.0213(11) 0.0254(12) C2 0.0324(13) 0.0469(13) 0.0312(12) -0.0026(10) 0.0062(10) 0.0062(10) C1 0.0326(14) 0.0414(12) 0.0365(13) 0.0046(10) 0.0031(10) 0.0072(10) C3 0.0345(13) 0.0445(13) 0.0358(13) 0.0037(10) 0.0054(10) 0.0100(10) O3 0.0505(14) 0.1129(16) 0.0562(13) -0.0187(12) 0.0072(10) 0.0158(12) N1 0.0308(11) 0.0453(11) 0.0407(12) -0.0009(9) 0.0080(9) 0.0082(9) C9 0.0298(13) 0.0385(12) 0.0389(13) -0.0039(10) 0.0068(10) 0.0065(10) C8 0.0306(13) 0.0433(13) 0.0404(14) 0.0031(10) 0.0047(10) 0.0083(10) C7 0.0391(14) 0.0400(13) 0.0537(16) 0.0011(11) 0.0044(12) 0.0050(11) C5 0.0456(17) 0.0634(17) 0.0566(17) 0.0188(14) 0.0189(13) 0.0116(13) C4 0.0456(16) 0.0548(15) 0.0402(14) 0.0069(11) 0.0118(12) 0.0117(12) C6 0.0399(16) 0.0515(15) 0.0634(19) 0.0152(13) 0.0122(13) 0.0036(12) C10 0.0564(19) 0.0638(17) 0.0553(18) 0.0001(13) 0.0091(15) 0.0179(15) C11 0.065(2) 0.120(3) 0.059(2) -0.0181(19) -0.0095(17) 0.034(2) _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 1.255(3) . ? O2 C10 1.194(3) . ? C2 C1 1.510(3) . ? C2 C3 1.518(3) . ? C2 C9 1.597(3) 2_566 ? C2 H2 0.9800 . ? C1 N1 1.331(3) . ? C3 C4 1.379(3) . ? C3 C8 1.397(3) . ? O3 C10 1.330(4) . ? O3 H3 1.03(3) . ? N1 C9 1.464(3) . ? N1 H1 1.08(2) . ? C9 C8 1.521(3) . ? C9 C2 1.597(3) 2_566 ? C9 H9 0.9800 . ? C8 C7 1.379(3) . ? C7 C6 1.388(3) . ? C7 H7 0.9300 . ? C5 C6 1.373(3) . ? C5 C4 1.385(3) . ? C5 H5 0.9300 . ? C4 H4 0.9300 . ? C6 H6 0.9300 . ? C10 C11 1.489(4) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? 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 C1 C2 C3 108.77(17) . . ? C1 C2 C9 110.40(18) . 2_566 ? C3 C2 C9 111.64(18) . 2_566 ? C1 C2 H2 108.7 . . ? C3 C2 H2 108.7 . . ? C9 C2 H2 108.7 2_566 . ? O1 C1 N1 122.6(2) . . ? O1 C1 C2 121.7(2) . . ? N1 C1 C2 115.7(2) . . ? C4 C3 C8 119.8(2) . . ? C4 C3 C2 124.2(2) . . ? C8 C3 C2 116.0(2) . . ? C10 O3 H3 110.7(17) . . ? C1 N1 C9 120.26(19) . . ? C1 N1 H1 125.8(12) . . ? C9 N1 H1 113.0(12) . . ? N1 C9 C8 108.00(18) . . ? N1 C9 C2 112.51(18) . 2_566 ? C8 C9 C2 112.30(18) . 2_566 ? N1 C9 H9 108.0 . . ? C8 C9 H9 108.0 . . ? C2 C9 H9 108.0 2_566 . ? C7 C8 C3 119.9(2) . . ? C7 C8 C9 124.2(2) . . ? C3 C8 C9 115.9(2) . . ? C8 C7 C6 119.9(2) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C6 C5 C4 120.5(2) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C4 C3 119.8(2) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C5 C6 C7 120.1(2) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? O2 C10 O3 122.0(3) . . ? O2 C10 C11 124.9(3) . . ? O3 C10 C11 113.0(3) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 C3 C2 C1 O1 135.8(2) . . . . ? C9 C2 C1 O1 -101.4(2) 2_566 . . . ? C3 C2 C1 N1 -44.4(3) . . . . ? C9 C2 C1 N1 78.4(2) 2_566 . . . ? C1 C2 C3 C4 -136.1(2) . . . . ? C9 C2 C3 C4 101.8(3) 2_566 . . . ? C1 C2 C3 C8 45.3(3) . . . . ? C9 C2 C3 C8 -76.8(2) 2_566 . . . ? O1 C1 N1 C9 177.5(2) . . . . ? C2 C1 N1 C9 -2.3(3) . . . . ? C1 N1 C9 C8 47.1(3) . . . . ? C1 N1 C9 C2 -77.4(3) . . . 2_566 ? C4 C3 C8 C7 -0.2(3) . . . . ? C2 C3 C8 C7 178.5(2) . . . . ? C4 C3 C8 C9 -179.7(2) . . . . ? C2 C3 C8 C9 -1.1(3) . . . . ? N1 C9 C8 C7 136.5(2) . . . . ? C2 C9 C8 C7 -98.9(3) 2_566 . . . ? N1 C9 C8 C3 -44.0(2) . . . . ? C2 C9 C8 C3 80.6(2) 2_566 . . . ? C3 C8 C7 C6 -0.1(3) . . . . ? C9 C8 C7 C6 179.4(2) . . . . ? C6 C5 C4 C3 0.2(4) . . . . ? C8 C3 C4 C5 0.1(4) . . . . ? C2 C3 C4 C5 -178.4(2) . . . . ? C4 C5 C6 C7 -0.5(4) . . . . ? C8 C7 C6 C5 0.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.99 _refine_diff_density_max 0.195 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.044 # Attachment 'I-1d.cif' data_dimer_of_irradiated_powder_of_cao5 _database_code_depnum_ccdc_archive 'CCDC 787297' #TrackingRef 'I-1d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol:2(dimer of Isoquinolin-3(2H)-one).HOAc ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C18 H14 N2 O2), C2 H4 O2' _chemical_formula_sum 'C35 H29 N2 O5' _chemical_formula_weight 557.60 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 14.166(3) _cell_length_b 9.432(2) _cell_length_c 20.139(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.88(2) _cell_angle_gamma 90.00 _cell_volume 2689.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1172 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17677 _diffrn_reflns_av_R_equivalents 0.089 _diffrn_reflns_av_sigmaI/netI 0.0633 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4896 _reflns_number_gt 3162 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0911P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4896 _refine_ls_number_parameters 355 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1034 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1667 _refine_ls_wR_factor_gt 0.1505 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.058 _refine_ls_shift/su_mean 0.002 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 0.20899(13) 0.26929(18) 0.42429(8) 0.0494(5) Uani 1 1 d . . . H1O1 H 0.2300 0.2928 0.4714 0.059 Uiso 1 1 d R . . O2 O 0.27834(15) 0.21511(18) 0.04961(9) 0.0582(6) Uani 1 1 d . . . O3 O 0.32725(14) 1.05359(17) 0.20863(8) 0.0497(5) Uani 1 1 d . . . N1 N 0.30050(15) 0.3240(2) 0.14950(9) 0.0422(5) Uani 1 1 d . . . H1 H 0.3168 0.2439 0.1668 0.051 Uiso 1 1 calc R . . N2 N 0.32351(16) 0.9511(2) 0.10712(10) 0.0416(5) Uani 1 1 d . . . H2 H 0.3131 1.0307 0.0874 0.050 Uiso 1 1 calc R . . C1 C 0.0351(2) 0.4807(3) 0.47832(13) 0.0484(7) Uani 1 1 d . . . C2 C 0.09457(19) 0.4460(3) 0.44096(12) 0.0462(6) Uani 1 1 d . . . C3 C 0.17083(18) 0.3974(3) 0.39789(11) 0.0396(6) Uani 1 1 d . . . C4 C 0.13087(17) 0.3637(3) 0.32756(11) 0.0394(6) Uani 1 1 d . . . C5 C 0.1529(2) 0.2394(3) 0.29641(13) 0.0481(7) Uani 1 1 d . . . H5 H 0.1906 0.1724 0.3184 0.058 Uiso 1 1 calc R . . C6 C 0.1191(2) 0.2131(3) 0.23221(15) 0.0572(8) Uani 1 1 d . . . H6 H 0.1334 0.1277 0.2118 0.069 Uiso 1 1 calc R . . C7 C 0.0651(2) 0.3111(3) 0.19872(14) 0.0603(8) Uani 1 1 d . . . H7 H 0.0433 0.2931 0.1555 0.072 Uiso 1 1 calc R . . C8 C 0.0432(2) 0.4359(3) 0.22906(14) 0.0605(8) Uani 1 1 d . . . H8 H 0.0062 0.5030 0.2065 0.073 Uiso 1 1 calc R . . C9 C 0.0761(2) 0.4623(3) 0.29327(13) 0.0532(7) Uani 1 1 d . . . H9 H 0.0611 0.5475 0.3136 0.064 Uiso 1 1 calc R . . C10 C 0.24661(18) 0.5132(2) 0.39352(11) 0.0382(6) Uani 1 1 d . . . C11 C 0.2239(2) 0.6559(3) 0.39436(12) 0.0463(6) Uani 1 1 d . . . H11 H 0.1615 0.6835 0.3995 0.056 Uiso 1 1 calc R . . C12 C 0.2935(2) 0.7581(3) 0.38756(13) 0.0524(7) Uani 1 1 d . . . H12 H 0.2776 0.8538 0.3880 0.063 Uiso 1 1 calc R . . C13 C 0.3855(2) 0.7185(3) 0.38030(13) 0.0555(8) Uani 1 1 d . . . H13 H 0.4320 0.7871 0.3761 0.067 Uiso 1 1 calc R . . C14 C 0.4091(2) 0.5778(3) 0.37915(14) 0.0592(8) Uani 1 1 d . . . H14 H 0.4716 0.5509 0.3739 0.071 Uiso 1 1 calc R . . C15 C 0.3399(2) 0.4756(3) 0.38581(13) 0.0506(7) Uani 1 1 d . . . H15 H 0.3564 0.3802 0.3851 0.061 Uiso 1 1 calc R . . C16 C 0.27667(17) 0.5689(2) 0.16579(11) 0.0355(6) Uani 1 1 d . . . C17 C 0.25687(17) 0.5808(2) 0.09678(11) 0.0367(6) Uani 1 1 d . . . C18 C 0.25752(18) 0.4649(2) 0.05698(12) 0.0407(6) Uani 1 1 d . . . H18 H 0.2439 0.4750 0.0117 0.049 Uiso 1 1 calc R . . C19 C 0.27874(18) 0.3277(3) 0.08325(12) 0.0416(6) Uani 1 1 d . . . C20 C 0.29813(18) 0.4395(2) 0.19013(12) 0.0406(6) Uani 1 1 d . . . H20 H 0.3115 0.4287 0.2354 0.049 Uiso 1 1 calc R . . C21 C 0.26862(18) 0.7020(2) 0.20744(11) 0.0396(6) Uani 1 1 d . . . H21 H 0.2617 0.6746 0.2540 0.048 Uiso 1 1 calc R . . C22 C 0.18029(19) 0.7779(3) 0.18356(14) 0.0476(7) Uani 1 1 d . . . H22 H 0.1381 0.8140 0.2137 0.057 Uiso 1 1 calc R . . C23 C 0.1641(2) 0.7919(3) 0.11898(14) 0.0485(7) Uani 1 1 d . . . H23 H 0.1107 0.8395 0.1027 0.058 Uiso 1 1 calc R . . C24 C 0.23425(18) 0.7289(2) 0.07178(12) 0.0405(6) Uani 1 1 d . . . H24 H 0.2045 0.7224 0.0273 0.049 Uiso 1 1 calc R . . C25 C 0.33475(18) 0.9472(2) 0.17346(12) 0.0392(6) Uani 1 1 d . . . C26 C 0.32878(18) 0.8214(2) 0.06810(11) 0.0395(6) Uani 1 1 d . . . H26 H 0.3369 0.8481 0.0216 0.047 Uiso 1 1 calc R . . C27 C 0.41622(18) 0.7419(2) 0.09182(11) 0.0385(6) Uani 1 1 d . . . C28 C 0.43356(17) 0.7362(2) 0.16041(12) 0.0372(6) Uani 1 1 d . . . C29 C 0.35938(18) 0.8028(2) 0.20233(11) 0.0376(6) Uani 1 1 d . . . H29 H 0.3866 0.8166 0.2472 0.045 Uiso 1 1 calc R . . C30 C 0.4800(2) 0.6795(3) 0.04992(13) 0.0484(7) Uani 1 1 d . . . H30 H 0.4696 0.6841 0.0041 0.058 Uiso 1 1 calc R . . C31 C 0.5587(2) 0.6105(3) 0.07601(14) 0.0535(7) Uani 1 1 d . . . H31 H 0.6005 0.5672 0.0477 0.064 Uiso 1 1 calc R . . C32 C 0.5761(2) 0.6054(3) 0.14416(14) 0.0509(7) Uani 1 1 d . . . H32 H 0.6295 0.5594 0.1615 0.061 Uiso 1 1 calc R . . C33 C 0.51329(18) 0.6693(3) 0.18611(13) 0.0440(6) Uani 1 1 d . . . H33 H 0.5249 0.6670 0.2318 0.053 Uiso 1 1 calc R . . O4 O 0.0915(6) 0.5103(8) -0.0688(4) 0.140(2) Uiso 0.50 1 d P . . C34 C 0.0198(8) 0.3939(13) -0.0027(6) 0.124(3) Uiso 0.50 1 d P . . C35 C 0.0214(8) 0.4771(13) -0.0309(6) 0.118(3) Uiso 0.50 1 d P . . 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 0.0675(13) 0.0391(10) 0.0412(10) 0.0047(8) -0.0034(9) 0.0004(9) O2 0.1009(17) 0.0306(10) 0.0422(10) -0.0062(8) -0.0111(10) 0.0036(9) O3 0.0743(14) 0.0312(9) 0.0431(10) -0.0076(8) -0.0036(9) 0.0032(9) N1 0.0641(14) 0.0259(10) 0.0365(11) 0.0013(9) 0.0002(9) 0.0011(9) N2 0.0623(14) 0.0249(10) 0.0371(11) 0.0002(9) -0.0048(9) 0.0015(9) C1 0.0493(16) 0.0551(17) 0.0413(14) -0.0034(12) 0.0084(12) -0.0060(13) C2 0.0493(16) 0.0503(16) 0.0393(14) -0.0030(12) 0.0069(12) -0.0073(13) C3 0.0452(15) 0.0393(13) 0.0346(12) 0.0017(11) 0.0058(11) -0.0016(11) C4 0.0384(14) 0.0429(14) 0.0373(13) -0.0009(11) 0.0089(10) -0.0030(11) C5 0.0504(17) 0.0452(15) 0.0488(15) -0.0037(13) 0.0023(12) 0.0013(12) C6 0.0605(19) 0.0552(17) 0.0559(17) -0.0147(14) 0.0028(14) -0.0074(14) C7 0.060(2) 0.075(2) 0.0451(15) -0.0087(15) -0.0030(14) -0.0143(16) C8 0.061(2) 0.069(2) 0.0510(16) 0.0031(15) -0.0081(14) 0.0071(15) C9 0.0562(18) 0.0550(17) 0.0483(16) -0.0027(13) -0.0021(13) 0.0060(14) C10 0.0465(15) 0.0400(13) 0.0283(12) -0.0013(10) 0.0040(10) -0.0016(11) C11 0.0535(17) 0.0434(15) 0.0420(14) -0.0004(12) 0.0046(12) 0.0004(12) C12 0.075(2) 0.0409(15) 0.0413(15) -0.0008(12) 0.0038(13) -0.0066(14) C13 0.064(2) 0.0629(19) 0.0402(15) -0.0002(13) 0.0057(13) -0.0211(15) C14 0.0477(18) 0.068(2) 0.0621(18) -0.0005(16) 0.0082(14) -0.0082(15) C15 0.0468(17) 0.0487(16) 0.0566(17) -0.0027(13) 0.0065(13) 0.0017(13) C16 0.0427(15) 0.0317(13) 0.0323(12) 0.0005(10) 0.0013(10) -0.0019(10) C17 0.0410(14) 0.0324(12) 0.0366(13) -0.0018(11) 0.0006(10) 0.0000(10) C18 0.0528(16) 0.0366(14) 0.0325(12) -0.0006(11) -0.0027(11) -0.0011(11) C19 0.0549(17) 0.0319(13) 0.0380(13) -0.0003(11) -0.0007(11) -0.0012(11) C20 0.0547(16) 0.0346(13) 0.0327(12) 0.0010(11) 0.0037(11) -0.0042(12) C21 0.0521(16) 0.0343(13) 0.0329(12) -0.0013(10) 0.0068(11) -0.0011(11) C22 0.0470(16) 0.0413(14) 0.0549(17) -0.0086(12) 0.0099(13) 0.0020(12) C23 0.0473(16) 0.0395(14) 0.0585(18) -0.0008(12) -0.0034(13) 0.0077(12) C24 0.0512(16) 0.0324(13) 0.0374(13) 0.0004(10) -0.0070(11) 0.0036(11) C25 0.0477(15) 0.0304(12) 0.0392(13) -0.0022(11) -0.0014(11) 0.0006(11) C26 0.0540(16) 0.0323(13) 0.0320(12) 0.0004(10) 0.0003(11) -0.0005(11) C27 0.0500(16) 0.0293(12) 0.0361(13) 0.0018(10) -0.0008(11) -0.0013(11) C28 0.0447(15) 0.0287(12) 0.0380(13) 0.0014(10) -0.0010(11) -0.0010(10) C29 0.0511(16) 0.0321(13) 0.0294(12) -0.0012(10) -0.0032(10) 0.0017(11) C30 0.0614(19) 0.0433(14) 0.0410(14) -0.0033(12) 0.0087(12) -0.0004(13) C31 0.0524(18) 0.0484(16) 0.0604(18) -0.0059(14) 0.0120(14) 0.0070(13) C32 0.0503(17) 0.0409(15) 0.0613(17) 0.0020(13) 0.0015(13) 0.0037(12) C33 0.0495(16) 0.0360(13) 0.0461(14) -0.0006(12) -0.0036(12) 0.0010(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 C3 1.420(3) . ? O1 H1O1 1.0091 . ? O2 C19 1.259(3) . ? O3 C25 1.235(3) . ? N1 C19 1.360(3) . ? N1 C20 1.364(3) . ? N1 H1 0.8600 . ? N2 C25 1.341(3) . ? N2 C26 1.457(3) . ? N2 H2 0.8600 . ? C1 C2 1.193(4) . ? C1 C1 1.394(5) 3_566 ? C2 C3 1.480(4) . ? C3 C10 1.536(3) . ? C3 C4 1.541(3) . ? C4 C5 1.370(3) . ? C4 C9 1.382(4) . ? C5 C6 1.386(4) . ? C5 H5 0.9300 . ? C6 C7 1.364(4) . ? C6 H6 0.9300 . ? C7 C8 1.367(4) . ? C7 H7 0.9300 . ? C8 C9 1.382(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.384(3) . ? C10 C15 1.381(4) . ? C11 C12 1.390(4) . ? C11 H11 0.9300 . ? C12 C13 1.368(4) . ? C12 H12 0.9300 . ? C13 C14 1.369(4) . ? C13 H13 0.9300 . ? C14 C15 1.385(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C20 1.346(3) . ? C16 C17 1.413(3) . ? C16 C21 1.516(3) . ? C17 C18 1.356(3) . ? C17 C24 1.516(3) . ? C18 C19 1.426(3) . ? C18 H18 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.507(4) . ? C21 C29 1.605(3) . ? C21 H21 0.9800 . ? C22 C23 1.320(4) . ? C22 H22 0.9300 . ? C23 C24 1.519(4) . ? C23 H23 0.9300 . ? C24 C26 1.602(4) . ? C24 H24 0.9800 . ? C25 C29 1.518(3) . ? C26 C27 1.511(3) . ? C26 H26 0.9800 . ? C27 C30 1.387(3) . ? C27 C28 1.396(3) . ? C28 C33 1.380(3) . ? C28 C29 1.506(3) . ? C29 H29 0.9800 . ? C30 C31 1.380(4) . ? C30 H30 0.9300 . ? C31 C32 1.387(4) . ? C31 H31 0.9300 . ? C32 C33 1.385(4) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? O4 C35 1.310(11) . ? O4 C34 2.024(14) . ? C34 C35 0.969(12) . ? C34 C35 1.518(14) 3_565 ? C34 C34 2.08(2) 3_565 ? C35 C34 1.518(14) 3_565 ? C35 C35 1.47(2) 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 C3 O1 H1O1 105.2 . . ? C19 N1 C20 124.0(2) . . ? C19 N1 H1 118.0 . . ? C20 N1 H1 118.0 . . ? C25 N2 C26 120.52(19) . . ? C25 N2 H2 119.7 . . ? C26 N2 H2 119.7 . . ? C2 C1 C1 179.1(4) . 3_566 ? C1 C2 C3 176.5(3) . . ? O1 C3 C2 108.66(19) . . ? O1 C3 C10 111.6(2) . . ? C2 C3 C10 109.8(2) . . ? O1 C3 C4 106.97(19) . . ? C2 C3 C4 110.4(2) . . ? C10 C3 C4 109.31(19) . . ? C5 C4 C9 118.6(2) . . ? C5 C4 C3 121.0(2) . . ? C9 C4 C3 120.2(2) . . ? C4 C5 C6 120.2(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 120.7(3) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 119.6(3) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C7 C8 C9 119.9(3) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C4 C9 C8 120.8(3) . . ? C4 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C11 C10 C15 118.4(2) . . ? C11 C10 C3 121.8(2) . . ? C15 C10 C3 119.8(2) . . ? C10 C11 C12 120.5(3) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 120.2(3) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 120.1(3) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 119.9(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C10 121.0(3) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? C20 C16 C17 117.7(2) . . ? C20 C16 C21 124.7(2) . . ? C17 C16 C21 117.5(2) . . ? C18 C17 C16 120.8(2) . . ? C18 C17 C24 123.5(2) . . ? C16 C17 C24 115.7(2) . . ? C17 C18 C19 121.2(2) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? O2 C19 N1 120.2(2) . . ? O2 C19 C18 124.6(2) . . ? N1 C19 C18 115.2(2) . . ? C16 C20 N1 121.0(2) . . ? C16 C20 H20 119.5 . . ? N1 C20 H20 119.5 . . ? C22 C21 C16 107.1(2) . . ? C22 C21 C29 110.90(19) . . ? C16 C21 C29 112.33(19) . . ? C22 C21 H21 108.8 . . ? C16 C21 H21 108.8 . . ? C29 C21 H21 108.8 . . ? C23 C22 C21 118.6(2) . . ? C23 C22 H22 120.7 . . ? C21 C22 H22 120.7 . . ? C22 C23 C24 118.7(2) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? C17 C24 C23 106.8(2) . . ? C17 C24 C26 110.4(2) . . ? C23 C24 C26 112.4(2) . . ? C17 C24 H24 109.1 . . ? C23 C24 H24 109.1 . . ? C26 C24 H24 109.1 . . ? O3 C25 N2 122.7(2) . . ? O3 C25 C29 122.2(2) . . ? N2 C25 C29 115.1(2) . . ? N2 C26 C27 107.55(19) . . ? N2 C26 C24 112.0(2) . . ? C27 C26 C24 113.16(19) . . ? N2 C26 H26 108.0 . . ? C27 C26 H26 108.0 . . ? C24 C26 H26 108.0 . . ? C30 C27 C28 119.2(2) . . ? C30 C27 C26 124.1(2) . . ? C28 C27 C26 116.6(2) . . ? C33 C28 C27 120.3(2) . . ? C33 C28 C29 123.9(2) . . ? C27 C28 C29 115.8(2) . . ? C28 C29 C25 108.37(19) . . ? C28 C29 C21 111.37(19) . . ? C25 C29 C21 112.4(2) . . ? C28 C29 H29 108.2 . . ? C25 C29 H29 108.2 . . ? C21 C29 H29 108.2 . . ? C31 C30 C27 120.2(2) . . ? C31 C30 H30 119.9 . . ? C27 C30 H30 119.9 . . ? C30 C31 C32 120.6(2) . . ? C30 C31 H31 119.7 . . ? C32 C31 H31 119.7 . . ? C33 C32 C31 119.4(3) . . ? C33 C32 H32 120.3 . . ? C31 C32 H32 120.3 . . ? C28 C33 C32 120.3(2) . . ? C28 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? C35 O4 C34 23.2(6) . . ? C35 C34 C35 68.2(13) . 3_565 ? C35 C34 C34 42.6(9) . 3_565 ? C35 C34 C34 25.6(6) 3_565 3_565 ? C35 C34 O4 32.2(9) . . ? C35 C34 O4 93.8(10) 3_565 . ? C34 C34 O4 69.8(7) 3_565 . ? C34 C35 O4 124.6(15) . . ? C34 C35 C34 111.8(13) . 3_565 ? O4 C35 C34 112.2(12) . 3_565 ? C34 C35 C35 74.0(13) . 3_565 ? O4 C35 C35 139.9(14) . 3_565 ? C34 C35 C35 37.8(6) 3_565 3_565 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.478 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.048 # Attachment 'I-1m.cif' data_Cao5(prism) _database_code_depnum_ccdc_archive 'CCDC 787298' #TrackingRef 'I-1m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol:2(Isoquinolin-3(2H)-one) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2 , 2(C9 H7 N O)' _chemical_formula_sum 'C48 H36 N2 O4' _chemical_formula_weight 704.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.1065(12) _cell_length_b 9.2347(4) _cell_length_c 16.4901(8) _cell_angle_alpha 90.00 _cell_angle_beta 115.4020(10) _cell_angle_gamma 90.00 _cell_volume 3728.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 286(2) _cell_measurement_reflns_used 2629 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 24.00 _exptl_crystal_description Prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 286(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12369 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.41 _reflns_number_total 3828 _reflns_number_gt 2565 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+1.0497P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3826 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1164 _refine_ls_wR_factor_gt 0.0984 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.14426(4) 0.57596(13) 0.46580(8) 0.0517(3) Uani 1 1 d . . . H1 H 0.1200 0.5626 0.4821 0.062 Uiso 1 1 calc R . . O2 O 0.06725(5) 0.45649(12) 0.02482(9) 0.0572(3) Uani 1 1 d . . . N1 N 0.00523(5) 0.32314(14) 0.05123(9) 0.0484(3) Uani 1 1 d . . . H1N H -0.0165 0.3962 0.0335 0.058 Uiso 1 1 calc R . . C1 C 0.02766(6) 0.50182(16) 0.27752(10) 0.0422(4) Uani 1 1 d . . . C2 C 0.07546(6) 0.50050(16) 0.32539(10) 0.0425(4) Uani 1 1 d . . . C3 C 0.13405(5) 0.49049(16) 0.38894(10) 0.0388(3) Uani 1 1 d . . . C4 C 0.16956(6) 0.55059(16) 0.34501(10) 0.0386(3) Uani 1 1 d . . . C5 C 0.20542(7) 0.66244(19) 0.38440(12) 0.0548(4) Uani 1 1 d . . . H5 H 0.2075 0.7034 0.4373 0.066 Uiso 1 1 calc R . . C6 C 0.23844(8) 0.7146(2) 0.34602(15) 0.0728(6) Uani 1 1 d . . . H6 H 0.2627 0.7897 0.3737 0.087 Uiso 1 1 calc R . . C7 C 0.23578(8) 0.6571(2) 0.26817(15) 0.0712(6) Uani 1 1 d . . . H7 H 0.2581 0.6925 0.2427 0.085 Uiso 1 1 calc R . . C8 C 0.19989(9) 0.5464(2) 0.22775(14) 0.0669(5) Uani 1 1 d . . . H8 H 0.1977 0.5068 0.1744 0.080 Uiso 1 1 calc R . . C9 C 0.16700(7) 0.4934(2) 0.26588(12) 0.0549(4) Uani 1 1 d . . . H9 H 0.1428 0.4183 0.2379 0.066 Uiso 1 1 calc R . . C10 C 0.14779(6) 0.33022(17) 0.41480(10) 0.0394(3) Uani 1 1 d . . . C11 C 0.18418(7) 0.2939(2) 0.50160(11) 0.0539(4) Uani 1 1 d . . . H11 H 0.2003 0.3665 0.5439 0.065 Uiso 1 1 calc R . . C12 C 0.19670(8) 0.1504(2) 0.52572(14) 0.0703(6) Uani 1 1 d . . . H12 H 0.2209 0.1273 0.5843 0.084 Uiso 1 1 calc R . . C13 C 0.17406(9) 0.0431(2) 0.46486(17) 0.0747(6) Uani 1 1 d . . . H13 H 0.1826 -0.0530 0.4819 0.090 Uiso 1 1 calc R . . C14 C 0.13863(9) 0.0763(2) 0.37821(15) 0.0704(6) Uani 1 1 d . . . H14 H 0.1236 0.0028 0.3362 0.084 Uiso 1 1 calc R . . C15 C 0.12522(7) 0.21953(18) 0.35335(12) 0.0554(4) Uani 1 1 d . . . H15 H 0.1008 0.2414 0.2947 0.066 Uiso 1 1 calc R . . C16 C 0.05617(6) 0.33705(17) 0.05197(10) 0.0451(4) Uani 1 1 d . . . C17 C 0.09038(7) 0.21748(18) 0.08265(11) 0.0498(4) Uani 1 1 d . . . H17 H 0.1254 0.2224 0.0856 0.060 Uiso 1 1 calc R . . C18 C 0.07370(7) 0.09056(17) 0.10913(10) 0.0477(4) Uani 1 1 d . . . C19 C 0.10740(8) -0.0349(2) 0.13844(13) 0.0643(5) Uani 1 1 d . . . H19 H 0.1426 -0.0335 0.1419 0.077 Uiso 1 1 calc R . . C20 C 0.08808(10) -0.1567(2) 0.16134(15) 0.0764(6) Uani 1 1 d . . . H20 H 0.1103 -0.2383 0.1796 0.092 Uiso 1 1 calc R . . C21 C 0.03585(10) -0.1627(2) 0.15817(15) 0.0754(6) Uani 1 1 d . . . H21 H 0.0239 -0.2475 0.1745 0.090 Uiso 1 1 calc R . . C22 C 0.00246(9) -0.0462(2) 0.13155(13) 0.0656(5) Uani 1 1 d . . . H22 H -0.0322 -0.0507 0.1299 0.079 Uiso 1 1 calc R . . C23 C 0.02055(7) 0.08301(17) 0.10606(11) 0.0488(4) Uani 1 1 d . . . C24 C -0.01242(7) 0.20427(18) 0.07606(12) 0.0528(4) Uani 1 1 d . . . H24 H -0.0474 0.2026 0.0732 0.063 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 0.0416(6) 0.0597(7) 0.0580(7) -0.0237(6) 0.0253(5) -0.0113(5) O2 0.0566(7) 0.0490(7) 0.0778(8) 0.0173(6) 0.0402(6) 0.0075(5) N1 0.0516(8) 0.0413(8) 0.0617(9) 0.0099(6) 0.0334(7) 0.0103(6) C1 0.0339(8) 0.0380(8) 0.0514(9) -0.0005(7) 0.0150(7) 0.0003(6) C2 0.0343(8) 0.0389(9) 0.0506(9) -0.0014(7) 0.0147(7) -0.0007(7) C3 0.0289(7) 0.0420(8) 0.0418(8) -0.0079(7) 0.0117(6) -0.0012(6) C4 0.0290(7) 0.0390(8) 0.0432(8) 0.0042(6) 0.0111(6) 0.0054(6) C5 0.0497(10) 0.0568(11) 0.0534(10) -0.0014(8) 0.0178(8) -0.0106(8) C6 0.0609(12) 0.0792(14) 0.0736(13) 0.0096(11) 0.0244(10) -0.0248(11) C7 0.0627(12) 0.0808(15) 0.0814(14) 0.0248(12) 0.0417(11) 0.0018(11) C8 0.0817(14) 0.0663(13) 0.0703(12) 0.0086(10) 0.0492(11) 0.0095(11) C9 0.0619(11) 0.0513(10) 0.0570(10) -0.0040(8) 0.0308(9) -0.0033(9) C10 0.0324(7) 0.0470(9) 0.0406(8) -0.0001(7) 0.0173(6) 0.0012(6) C11 0.0447(9) 0.0657(12) 0.0476(9) 0.0041(8) 0.0161(8) 0.0022(8) C12 0.0640(12) 0.0800(15) 0.0624(12) 0.0267(11) 0.0227(10) 0.0177(11) C13 0.0840(15) 0.0580(13) 0.0936(16) 0.0222(12) 0.0492(13) 0.0221(11) C14 0.0919(15) 0.0469(11) 0.0803(14) -0.0045(10) 0.0445(12) 0.0040(10) C15 0.0666(11) 0.0460(10) 0.0495(9) -0.0021(8) 0.0211(9) 0.0033(8) C16 0.0482(9) 0.0450(9) 0.0489(9) 0.0038(7) 0.0273(7) 0.0050(7) C17 0.0464(9) 0.0516(10) 0.0554(10) 0.0051(8) 0.0256(8) 0.0081(8) C18 0.0566(10) 0.0434(9) 0.0447(9) 0.0018(7) 0.0232(8) 0.0077(8) C19 0.0692(12) 0.0541(12) 0.0692(12) 0.0116(9) 0.0292(10) 0.0189(9) C20 0.0957(17) 0.0506(12) 0.0802(14) 0.0172(10) 0.0352(13) 0.0227(11) C21 0.0988(17) 0.0486(12) 0.0800(14) 0.0182(10) 0.0394(13) 0.0020(11) C22 0.0786(13) 0.0523(12) 0.0750(13) 0.0109(9) 0.0416(11) -0.0017(10) C23 0.0609(10) 0.0421(9) 0.0494(9) 0.0032(7) 0.0295(8) 0.0029(8) C24 0.0550(10) 0.0492(10) 0.0646(11) 0.0083(8) 0.0355(9) 0.0040(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 C3 1.4160(17) . ? O2 C16 1.2738(18) . ? N1 C24 1.330(2) . ? N1 C16 1.3816(19) . ? C1 C2 1.1936(19) . ? C1 C1 1.380(3) 2 ? C2 C3 1.484(2) . ? C3 C4 1.536(2) . ? C3 C10 1.541(2) . ? C4 C5 1.376(2) . ? C4 C9 1.381(2) . ? C5 C6 1.385(3) . ? C6 C7 1.362(3) . ? C7 C8 1.371(3) . ? C8 C9 1.382(3) . ? C10 C15 1.384(2) . ? C10 C11 1.387(2) . ? C11 C12 1.383(3) . ? C12 C13 1.355(3) . ? C13 C14 1.371(3) . ? C14 C15 1.386(3) . ? C16 C17 1.390(2) . ? C17 C18 1.392(2) . ? C18 C23 1.422(2) . ? C18 C19 1.425(2) . ? C19 C20 1.361(3) . ? C20 C21 1.395(3) . ? C21 C22 1.352(3) . ? C22 C23 1.421(2) . ? C23 C24 1.385(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 C24 N1 C16 124.34(14) . . ? C2 C1 C1 179.37(15) . 2 ? C1 C2 C3 175.73(17) . . ? O1 C3 C2 109.67(12) . . ? O1 C3 C4 107.42(12) . . ? C2 C3 C4 109.99(12) . . ? O1 C3 C10 110.89(12) . . ? C2 C3 C10 108.29(12) . . ? C4 C3 C10 110.58(11) . . ? C5 C4 C9 118.16(15) . . ? C5 C4 C3 120.51(14) . . ? C9 C4 C3 121.33(14) . . ? C4 C5 C6 120.63(18) . . ? C7 C6 C5 120.77(19) . . ? C6 C7 C8 119.23(18) . . ? C7 C8 C9 120.29(19) . . ? C4 C9 C8 120.91(18) . . ? C15 C10 C11 118.18(15) . . ? C15 C10 C3 121.90(13) . . ? C11 C10 C3 119.91(14) . . ? C12 C11 C10 120.46(17) . . ? C13 C12 C11 120.66(18) . . ? C12 C13 C14 120.03(19) . . ? C13 C14 C15 119.93(19) . . ? C10 C15 C14 120.72(17) . . ? O2 C16 N1 117.57(14) . . ? O2 C16 C17 126.49(15) . . ? N1 C16 C17 115.95(14) . . ? C16 C17 C18 121.81(15) . . ? C17 C18 C23 119.38(15) . . ? C17 C18 C19 122.94(16) . . ? C23 C18 C19 117.67(16) . . ? C20 C19 C18 119.95(19) . . ? C19 C20 C21 121.82(18) . . ? C22 C21 C20 120.52(19) . . ? C21 C22 C23 119.77(19) . . ? C24 C23 C22 122.23(16) . . ? C24 C23 C18 117.51(15) . . ? C22 C23 C18 120.25(16) . . ? N1 C24 C23 120.99(15) . . ? 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 C1 C1 C2 C3 -24(22) 2 . . . ? C1 C2 C3 O1 -82(2) . . . . ? C1 C2 C3 C4 160(2) . . . . ? C1 C2 C3 C10 39(2) . . . . ? O1 C3 C4 C5 3.51(19) . . . . ? C2 C3 C4 C5 122.82(15) . . . . ? C10 C3 C4 C5 -117.63(15) . . . . ? O1 C3 C4 C9 -177.26(14) . . . . ? C2 C3 C4 C9 -57.95(19) . . . . ? C10 C3 C4 C9 61.61(18) . . . . ? C9 C4 C5 C6 -0.8(2) . . . . ? C3 C4 C5 C6 178.47(16) . . . . ? C4 C5 C6 C7 0.5(3) . . . . ? C5 C6 C7 C8 0.0(3) . . . . ? C6 C7 C8 C9 -0.3(3) . . . . ? C5 C4 C9 C8 0.5(2) . . . . ? C3 C4 C9 C8 -178.74(15) . . . . ? C7 C8 C9 C4 0.0(3) . . . . ? O1 C3 C10 C15 157.78(14) . . . . ? C2 C3 C10 C15 37.42(19) . . . . ? C4 C3 C10 C15 -83.17(17) . . . . ? O1 C3 C10 C11 -22.90(18) . . . . ? C2 C3 C10 C11 -143.27(14) . . . . ? C4 C3 C10 C11 96.15(16) . . . . ? C15 C10 C11 C12 -0.9(2) . . . . ? C3 C10 C11 C12 179.76(15) . . . . ? C10 C11 C12 C13 0.6(3) . . . . ? C11 C12 C13 C14 0.4(3) . . . . ? C12 C13 C14 C15 -1.2(3) . . . . ? C11 C10 C15 C14 0.2(3) . . . . ? C3 C10 C15 C14 179.49(16) . . . . ? C13 C14 C15 C10 0.9(3) . . . . ? C24 N1 C16 O2 178.77(16) . . . . ? C24 N1 C16 C17 -1.2(2) . . . . ? O2 C16 C17 C18 -178.64(16) . . . . ? N1 C16 C17 C18 1.3(2) . . . . ? C16 C17 C18 C23 -0.9(2) . . . . ? C16 C17 C18 C19 178.19(16) . . . . ? C17 C18 C19 C20 -178.40(18) . . . . ? C23 C18 C19 C20 0.7(3) . . . . ? C18 C19 C20 C21 -0.8(3) . . . . ? C19 C20 C21 C22 0.3(3) . . . . ? C20 C21 C22 C23 0.4(3) . . . . ? C21 C22 C23 C24 178.30(18) . . . . ? C21 C22 C23 C18 -0.5(3) . . . . ? C17 C18 C23 C24 0.2(2) . . . . ? C19 C18 C23 C24 -178.89(16) . . . . ? C17 C18 C23 C22 179.08(16) . . . . ? C19 C18 C23 C22 0.0(2) . . . . ? C16 N1 C24 C23 0.6(3) . . . . ? C22 C23 C24 N1 -178.91(16) . . . . ? C18 C23 C24 N1 -0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.147 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.036 # Attachment 'I-1md.cif' data_Cao5(prism)_dimer _database_code_depnum_ccdc_archive 'CCDC 787299' #TrackingRef 'I-1md.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol: 2(dimer of Isoquinolin-3(2H)-one) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2 , C18 H14 N2 O2' _chemical_formula_sum 'C48 H36 N2 O4' _chemical_formula_weight 704.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.761(8) _cell_length_b 9.111(3) _cell_length_c 16.998(6) _cell_angle_alpha 90.00 _cell_angle_beta 114.443(9) _cell_angle_gamma 90.00 _cell_volume 3773(2) _cell_formula_units_Z 4 _cell_measurement_temperature 286(2) _cell_measurement_reflns_used 1166 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 19.41 _exptl_crystal_description Prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 286(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12245 _diffrn_reflns_av_R_equivalents 0.0971 _diffrn_reflns_av_sigmaI/netI 0.1166 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 26.45 _reflns_number_total 3873 _reflns_number_gt 1294 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1920P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0042(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3873 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2198 _refine_ls_R_factor_gt 0.0879 _refine_ls_wR_factor_ref 0.3502 _refine_ls_wR_factor_gt 0.2394 _refine_ls_goodness_of_fit_ref 0.926 _refine_ls_restrained_S_all 0.926 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.001 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 0.14365(14) 0.5925(5) 0.4501(3) 0.1096(15) Uani 1 1 d . . . H1 H 0.1265 0.5621 0.4771 0.131 Uiso 1 1 calc R . . C1 C 0.0277(2) 0.5048(5) 0.2752(4) 0.0872(16) Uani 1 1 d . . . C2 C 0.0760(2) 0.5051(5) 0.3181(4) 0.0832(15) Uani 1 1 d . . . C3 C 0.13466(17) 0.4982(5) 0.3794(3) 0.0729(14) Uani 1 1 d . . . C4 C 0.17094(19) 0.5566(5) 0.3350(4) 0.0807(15) Uani 1 1 d . . . C5 C 0.2123(2) 0.6543(7) 0.3767(5) 0.114(2) Uani 1 1 d . . . H5 H 0.2177 0.6898 0.4309 0.136 Uiso 1 1 calc R . . C6 C 0.2460(3) 0.7004(10) 0.3381(7) 0.160(4) Uani 1 1 d . . . H6 H 0.2741 0.7665 0.3671 0.192 Uiso 1 1 calc R . . C7 C 0.2392(5) 0.6523(15) 0.2605(10) 0.171(5) Uani 1 1 d . . . H7 H 0.2625 0.6844 0.2358 0.206 Uiso 1 1 calc R . . C8 C 0.1974(5) 0.5543(10) 0.2163(7) 0.162(4) Uani 1 1 d . . . H8 H 0.1918 0.5210 0.1616 0.194 Uiso 1 1 calc R . . C9 C 0.1645(3) 0.5079(7) 0.2547(5) 0.117(2) Uani 1 1 d . . . H9 H 0.1367 0.4408 0.2257 0.140 Uiso 1 1 calc R . . C10 C 0.14932(19) 0.3411(6) 0.4079(4) 0.0789(14) Uani 1 1 d . . . C11 C 0.1815(2) 0.3073(8) 0.4934(4) 0.108(2) Uani 1 1 d . . . H11 H 0.1939 0.3834 0.5334 0.130 Uiso 1 1 calc R . . C12 C 0.1957(3) 0.1681(15) 0.5213(7) 0.156(4) Uani 1 1 d . . . H12 H 0.2171 0.1487 0.5794 0.187 Uiso 1 1 calc R . . C13 C 0.1780(4) 0.0572(12) 0.4629(10) 0.162(5) Uani 1 1 d . . . H13 H 0.1877 -0.0388 0.4815 0.194 Uiso 1 1 calc R . . C14 C 0.1464(4) 0.0831(8) 0.3777(7) 0.138(3) Uani 1 1 d . . . H14 H 0.1348 0.0056 0.3387 0.166 Uiso 1 1 calc R . . C15 C 0.1318(3) 0.2267(7) 0.3495(5) 0.1048(19) Uani 1 1 d . . . H15 H 0.1102 0.2455 0.2915 0.126 Uiso 1 1 calc R . . O2A O -0.0694(9) 0.566(3) -0.0241(10) 0.080(4) Uani 0.50 1 d P . . O2B O -0.0562(9) 0.580(3) 0.0153(11) 0.092(5) Uani 0.50 1 d P . . N1C N 0.00073(19) 0.6827(4) -0.0399(4) 0.1082(18) Uani 1 1 d . . . C16C C -0.0451(3) 0.6893(6) -0.0243(5) 0.123(3) Uani 1 1 d . . . C17A C -0.0625(8) 0.8459(19) -0.0002(10) 0.079(5) Uani 0.50 1 d P . . C18C C -0.0560(2) 0.9389(6) -0.0687(4) 0.0908(18) Uani 1 1 d . . . C19A C -0.0691(5) 1.0943(12) -0.0589(10) 0.087(3) Uani 0.50 1 d P . . C20A C -0.0687(6) 1.1811(14) -0.1365(11) 0.103(4) Uani 0.50 1 d P . . C21A C -0.0217(6) 1.1712(13) -0.1471(11) 0.095(4) Uani 0.50 1 d P . . C22A C -0.0101(6) 1.0169(12) -0.1530(10) 0.093(4) Uani 0.50 1 d P . . C23C C -0.0071(3) 0.9313(5) -0.0825(4) 0.0907(18) Uani 1 1 d . . . C24A C -0.0241(10) 1.186(3) 0.0679(18) 0.093(7) Uani 0.50 1 d P . . C17B C -0.0723(7) 0.825(2) -0.0475(11) 0.078(5) Uani 0.50 1 d P . . C19B C -0.1046(5) 1.0279(12) -0.1247(8) 0.083(3) Uani 0.50 1 d P . . C22B C 0.0251(5) 1.0745(12) -0.0885(9) 0.083(3) Uani 0.50 1 d P . . C24B C -0.0291(11) 1.187(3) 0.036(2) 0.145(16) Uani 0.50 1 d P . . C21B C -0.0532(8) 1.1096(16) -0.2032(10) 0.109(5) Uani 0.50 1 d P . . C20B C -0.1030(6) 1.1128(16) -0.1899(9) 0.099(4) Uani 0.50 1 d P . . 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 0.051(2) 0.136(3) 0.134(3) -0.055(3) 0.032(2) -0.017(2) C1 0.049(3) 0.073(3) 0.121(4) 0.003(3) 0.016(3) 0.002(2) C2 0.052(3) 0.069(3) 0.111(4) 0.001(3) 0.015(3) 0.005(2) C3 0.037(2) 0.076(3) 0.093(3) -0.005(3) 0.015(2) -0.001(2) C4 0.049(3) 0.070(3) 0.113(4) 0.012(3) 0.023(3) 0.006(2) C5 0.073(4) 0.106(4) 0.137(5) 0.028(4) 0.019(4) -0.019(4) C6 0.081(5) 0.151(8) 0.225(11) 0.072(8) 0.041(7) -0.026(5) C7 0.132(8) 0.166(10) 0.256(14) 0.093(10) 0.121(10) 0.041(7) C8 0.219(11) 0.114(6) 0.218(10) 0.039(7) 0.156(10) 0.028(7) C9 0.138(6) 0.093(4) 0.145(6) 0.000(4) 0.084(5) -0.001(4) C10 0.046(3) 0.088(4) 0.103(4) 0.011(3) 0.032(3) 0.005(3) C11 0.055(3) 0.150(6) 0.116(5) 0.045(4) 0.032(3) 0.000(4) C12 0.063(5) 0.205(10) 0.191(10) 0.118(9) 0.045(5) 0.020(6) C13 0.085(7) 0.140(8) 0.286(16) 0.108(9) 0.104(9) 0.052(6) C14 0.125(7) 0.090(6) 0.229(10) 0.017(6) 0.102(7) 0.022(5) C15 0.103(5) 0.081(4) 0.137(5) 0.015(4) 0.056(4) 0.019(4) O2A 0.066(9) 0.054(6) 0.119(12) 0.023(9) 0.037(9) -0.002(5) O2B 0.070(11) 0.067(7) 0.147(15) 0.015(11) 0.052(11) 0.004(7) N1C 0.095(4) 0.060(3) 0.205(5) 0.035(3) 0.098(4) 0.016(2) C16C 0.115(5) 0.063(4) 0.239(8) 0.054(4) 0.122(6) 0.027(3) C17A 0.112(12) 0.053(7) 0.106(13) 0.016(9) 0.079(13) 0.013(7) C18C 0.112(5) 0.057(3) 0.140(5) 0.027(3) 0.089(4) 0.021(3) C19A 0.090(9) 0.062(7) 0.124(10) 0.005(7) 0.060(8) 0.003(6) C20A 0.103(10) 0.075(8) 0.152(13) 0.053(8) 0.075(10) 0.035(7) C21A 0.089(9) 0.065(8) 0.146(12) 0.035(7) 0.065(9) 0.018(7) C22A 0.125(11) 0.063(7) 0.123(10) 0.029(7) 0.082(9) 0.033(8) C23C 0.122(5) 0.052(3) 0.136(5) 0.023(3) 0.091(4) 0.017(3) C24A 0.090(11) 0.066(11) 0.130(14) 0.054(9) 0.053(9) -0.003(8) C17B 0.073(9) 0.069(9) 0.116(13) 0.025(10) 0.063(11) 0.024(7) C19B 0.082(8) 0.068(7) 0.099(8) 0.013(6) 0.039(7) 0.022(6) C22B 0.088(8) 0.068(7) 0.109(10) 0.025(7) 0.057(7) 0.012(6) C24B 0.137(19) 0.105(15) 0.28(4) 0.142(19) 0.17(2) 0.103(15) C21B 0.152(15) 0.081(9) 0.126(12) 0.007(8) 0.089(12) 0.010(10) C20B 0.110(11) 0.095(10) 0.089(9) 0.006(7) 0.038(8) 0.019(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 C3 1.415(6) . ? C1 C2 1.192(6) . ? C1 C1 1.373(10) 2 ? C2 C3 1.483(7) . ? C3 C10 1.510(7) . ? C3 C4 1.550(7) . ? C4 C5 1.368(8) . ? C4 C9 1.375(8) . ? C5 C6 1.382(10) . ? C6 C7 1.330(14) . ? C7 C8 1.385(14) . ? C8 C9 1.363(10) . ? C10 C15 1.381(8) . ? C10 C11 1.384(8) . ? C11 C12 1.352(11) . ? C12 C13 1.357(13) . ? C13 C14 1.361(13) . ? C14 C15 1.393(9) . ? O2A O2B 0.63(3) . ? O2A C16C 1.30(2) . ? O2B C16C 1.31(2) . ? N1C C16C 1.358(7) . ? N1C C24B 1.40(3) 5_575 ? N1C C24A 1.52(2) 5_575 ? C16C C17B 1.406(18) . ? C16C C17A 1.606(16) . ? C17A C17B 0.759(17) . ? C17A C18C 1.507(16) . ? C17A C22B 1.60(2) 5_575 ? C18C C17B 1.237(18) . ? C18C C23C 1.423(7) . ? C18C C19A 1.485(12) . ? C18C C19B 1.495(12) . ? C19A C19B 1.281(16) . ? C19A C20A 1.542(17) . ? C19A C24B 1.74(4) . ? C19A C20B 2.03(2) . ? C20A C20B 1.169(17) . ? C20A C21A 1.344(16) . ? C20A C21B 1.51(2) . ? C20A C19B 1.753(18) . ? C21A C21B 1.127(17) . ? C21A C22A 1.452(16) . ? C21A C22B 1.518(17) . ? C22A C22B 1.228(16) . ? C22A C21B 1.399(19) . ? C22A C23C 1.404(12) . ? C23C C24A 1.31(2) 5_575 ? C23C C24B 1.44(2) 5_575 ? C23C C22B 1.590(12) . ? C24A C24B 0.50(5) . ? C24A C23C 1.31(2) 5_575 ? C24A N1C 1.52(2) 5_575 ? C19B C20B 1.367(15) . ? C22B C17A 1.60(2) 5_575 ? C24B N1C 1.40(3) 5_575 ? C24B C23C 1.44(2) 5_575 ? C21B C20B 1.44(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 C2 C1 C1 179.2(8) . 2 ? C1 C2 C3 173.5(6) . . ? O1 C3 C2 109.3(4) . . ? O1 C3 C10 111.9(4) . . ? C2 C3 C10 109.0(4) . . ? O1 C3 C4 106.5(4) . . ? C2 C3 C4 109.7(4) . . ? C10 C3 C4 110.5(4) . . ? C5 C4 C9 117.8(6) . . ? C5 C4 C3 120.5(6) . . ? C9 C4 C3 121.7(5) . . ? C4 C5 C6 119.9(8) . . ? C7 C6 C5 121.5(10) . . ? C6 C7 C8 119.9(10) . . ? C9 C8 C7 118.5(10) . . ? C8 C9 C4 122.3(8) . . ? C15 C10 C11 117.8(6) . . ? C15 C10 C3 121.3(5) . . ? C11 C10 C3 121.0(6) . . ? C12 C11 C10 122.7(8) . . ? C11 C12 C13 118.6(10) . . ? C12 C13 C14 121.6(10) . . ? C13 C14 C15 119.4(9) . . ? C10 C15 C14 119.9(7) . . ? O2B O2A C16C 77(4) . . ? O2A O2B C16C 75(4) . . ? C16C N1C C24B 118.1(9) . 5_575 ? C16C N1C C24A 123.3(11) . 5_575 ? C24B N1C C24A 19(2) 5_575 5_575 ? O2A C16C O2B 27.9(11) . . ? O2A C16C N1C 117.2(12) . . ? O2B C16C N1C 118.9(12) . . ? O2A C16C C17B 123.8(14) . . ? O2B C16C C17B 127.9(14) . . ? N1C C16C C17B 113.0(8) . . ? O2A C16C C17A 124.5(13) . . ? O2B C16C C17A 113.3(13) . . ? N1C C16C C17A 118.0(8) . . ? C17B C16C C17A 28.2(8) . . ? C17B C17A C18C 55(2) . . ? C17B C17A C22B 157(3) . 5_575 ? C18C C17A C22B 104.2(11) . 5_575 ? C17B C17A C16C 61(2) . . ? C18C C17A C16C 99.4(8) . . ? C22B C17A C16C 120.6(13) 5_575 . ? C17B C18C C23C 117.9(8) . . ? C17B C18C C19A 129.7(8) . . ? C23C C18C C19A 109.9(6) . . ? C17B C18C C19B 108.7(10) . . ? C23C C18C C19B 122.6(6) . . ? C19A C18C C19B 50.9(6) . . ? C17B C18C C17A 30.1(10) . . ? C23C C18C C17A 120.6(8) . . ? C19A C18C C17A 109.9(8) . . ? C19B C18C C17A 116.6(9) . . ? C19B C19A C18C 64.9(8) . . ? C19B C19A C20A 76.2(11) . . ? C18C C19A C20A 107.9(10) . . ? C19B C19A C24B 170.9(12) . . ? C18C C19A C24B 118.8(11) . . ? C20A C19A C24B 109.0(12) . . ? C19B C19A C20B 41.4(8) . . ? C18C C19A C20B 88.6(8) . . ? C20A C19A C20B 34.8(7) . . ? C24B C19A C20B 143.1(11) . . ? C20B C20A C21A 109.7(17) . . ? C20B C20A C21B 63.7(14) . . ? C21A C20A C21B 46.1(8) . . ? C20B C20A C19A 96.3(12) . . ? C21A C20A C19A 114.7(11) . . ? C21B C20A C19A 121.5(10) . . ? C20B C20A C19B 51.1(9) . . ? C21A C20A C19B 123.3(10) . . ? C21B C20A C19B 94.3(12) . . ? C19A C20A C19B 45.2(6) . . ? C21B C21A C20A 74.5(13) . . ? C21B C21A C22A 64.3(13) . . ? C20A C21A C22A 108.3(12) . . ? C21B C21A C22B 113.0(14) . . ? C20A C21A C22B 121.0(11) . . ? C22A C21A C22B 48.8(7) . . ? C22B C22A C21B 114.9(12) . . ? C22B C22A C23C 74.0(9) . . ? C21B C22A C23C 126.6(11) . . ? C22B C22A C21A 68.4(11) . . ? C21B C22A C21A 46.5(7) . . ? C23C C22A C21A 114.6(10) . . ? C24A C23C C22A 114.8(13) 5_575 . ? C24A C23C C18C 124.3(10) 5_575 . ? C22A C23C C18C 112.5(7) . . ? C24A C23C C24B 20(2) 5_575 5_575 ? C22A C23C C24B 131.9(12) . 5_575 ? C18C C23C C24B 113.6(10) . 5_575 ? C24A C23C C22B 111.1(10) 5_575 . ? C22A C23C C22B 47.9(6) . . ? C18C C23C C22B 122.1(5) . . ? C24B C23C C22B 112.7(13) 5_575 . ? C24B C24A C23C 95(5) . 5_575 ? C24B C24A N1C 67(5) . 5_575 ? C23C C24A N1C 112.9(16) 5_575 5_575 ? C17A C17B C18C 95(3) . . ? C17A C17B C16C 91(3) . . ? C18C C17B C16C 127.8(13) . . ? C19A C19B C20B 100.4(11) . . ? C19A C19B C18C 64.1(8) . . ? C20B C19B C18C 120.8(9) . . ? C19A C19B C20A 58.7(9) . . ? C20B C19B C20A 41.7(7) . . ? C18C C19B C20A 97.5(8) . . ? C22A C22B C21A 62.8(10) . . ? C22A C22B C17A 170.2(12) . 5_575 ? C21A C22B C17A 112.3(12) . 5_575 ? C22A C22B C23C 58.1(8) . . ? C21A C22B C23C 101.3(10) . . ? C17A C22B C23C 117.2(9) 5_575 . ? C24A C24B N1C 94(6) . 5_575 ? C24A C24B C23C 65(5) . 5_575 ? N1C C24B C23C 112(2) 5_575 5_575 ? C24A C24B C19A 142(6) . . ? N1C C24B C19A 124.5(19) 5_575 . ? C23C C24B C19A 99.3(18) 5_575 . ? C21A C21B C22A 69.2(14) . . ? C21A C21B C20B 105.9(14) . . ? C22A C21B C20B 120.0(12) . . ? C21A C21B C20A 59.3(11) . . ? C22A C21B C20A 102.5(13) . . ? C20B C21B C20A 46.7(8) . . ? C20A C20B C19B 87.1(12) . . ? C20A C20B C21B 69.7(13) . . ? C19B C20B C21B 117.2(12) . . ? C20A C20B C19A 48.9(9) . . ? C19B C20B C19A 38.3(7) . . ? C21B C20B C19A 98.5(11) . . ? 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 C1 C1 C2 C3 -167(27) 2 . . . ? C1 C2 C3 O1 -64(5) . . . . ? C1 C2 C3 C10 58(5) . . . . ? C1 C2 C3 C4 179(100) . . . . ? O1 C3 C4 C5 15.5(6) . . . . ? C2 C3 C4 C5 133.6(5) . . . . ? C10 C3 C4 C5 -106.3(6) . . . . ? O1 C3 C4 C9 -167.5(5) . . . . ? C2 C3 C4 C9 -49.3(6) . . . . ? C10 C3 C4 C9 70.8(6) . . . . ? C9 C4 C5 C6 -0.2(9) . . . . ? C3 C4 C5 C6 177.0(6) . . . . ? C4 C5 C6 C7 0.3(13) . . . . ? C5 C6 C7 C8 0.3(16) . . . . ? C6 C7 C8 C9 -0.9(15) . . . . ? C7 C8 C9 C4 1.0(12) . . . . ? C5 C4 C9 C8 -0.5(9) . . . . ? C3 C4 C9 C8 -177.6(6) . . . . ? O1 C3 C10 C15 164.3(4) . . . . ? C2 C3 C10 C15 43.3(6) . . . . ? C4 C3 C10 C15 -77.2(6) . . . . ? O1 C3 C10 C11 -16.6(6) . . . . ? C2 C3 C10 C11 -137.5(5) . . . . ? C4 C3 C10 C11 101.9(5) . . . . ? C15 C10 C11 C12 -0.6(8) . . . . ? C3 C10 C11 C12 -179.7(5) . . . . ? C10 C11 C12 C13 0.6(11) . . . . ? C11 C12 C13 C14 -0.2(13) . . . . ? C12 C13 C14 C15 -0.1(13) . . . . ? C11 C10 C15 C14 0.2(8) . . . . ? C3 C10 C15 C14 179.4(5) . . . . ? C13 C14 C15 C10 0.1(10) . . . . ? O2B O2A C16C N1C 101(4) . . . . ? O2B O2A C16C C17B -108(4) . . . . ? O2B O2A C16C C17A -74(5) . . . . ? O2A O2B C16C N1C -94(4) . . . . ? O2A O2B C16C C17B 92(5) . . . . ? O2A O2B C16C C17A 120(4) . . . . ? C24B N1C C16C O2A -176.9(18) 5_575 . . . ? C24A N1C C16C O2A 161.5(15) 5_575 . . . ? C24B N1C C16C O2B -145.3(18) 5_575 . . . ? C24A N1C C16C O2B -166.8(16) 5_575 . . . ? C24B N1C C16C C17B 29.1(19) 5_575 . . . ? C24A N1C C16C C17B 7.6(18) 5_575 . . . ? C24B N1C C16C C17A -1.7(19) 5_575 . . . ? C24A N1C C16C C17A -23.2(17) 5_575 . . . ? O2A C16C C17A C17B -98(3) . . . . ? O2B C16C C17A C17B -128(3) . . . . ? N1C C16C C17A C17B 87(3) . . . . ? O2A C16C C17A C18C -139.1(12) . . . . ? O2B C16C C17A C18C -168.4(12) . . . . ? N1C C16C C17A C18C 46.0(14) . . . . ? C17B C16C C17A C18C -41(2) . . . . ? O2A C16C C17A C22B 108.1(16) . . . 5_575 ? O2B C16C C17A C22B 78.8(16) . . . 5_575 ? N1C C16C C17A C22B -66.8(13) . . . 5_575 ? C17B C16C C17A C22B -153(3) . . . 5_575 ? C22B C17A C18C C17B 169(3) 5_575 . . . ? C16C C17A C18C C17B 44.3(19) . . . . ? C17B C17A C18C C23C -94(3) . . . . ? C22B C17A C18C C23C 75.6(11) 5_575 . . . ? C16C C17A C18C C23C -49.4(13) . . . . ? C17B C17A C18C C19A 137(2) . . . . ? C22B C17A C18C C19A -53.8(13) 5_575 . . . ? C16C C17A C18C C19A -178.9(9) . . . . ? C17B C17A C18C C19B 81(3) . . . . ? C22B C17A C18C C19B -109.2(11) 5_575 . . . ? C16C C17A C18C C19B 125.7(10) . . . . ? C17B C18C C19A C19B -82.1(15) . . . . ? C23C C18C C19A C19B 116.3(8) . . . . ? C17A C18C C19A C19B -108.6(11) . . . . ? C17B C18C C19A C20A -146.8(14) . . . . ? C23C C18C C19A C20A 51.7(12) . . . . ? C19B C18C C19A C20A -64.6(11) . . . . ? C17A C18C C19A C20A -173.2(12) . . . . ? C17B C18C C19A C24B 88.6(17) . . . . ? C23C C18C C19A C24B -73.0(12) . . . . ? C19B C18C C19A C24B 170.7(14) . . . . ? C17A C18C C19A C24B 62.1(15) . . . . ? C17B C18C C19A C20B -117.3(14) . . . . ? C23C C18C C19A C20B 81.1(8) . . . . ? C19B C18C C19A C20B -35.2(7) . . . . ? C17A C18C C19A C20B -143.8(10) . . . . ? C19B C19A C20A C20B 1.9(11) . . . . ? C18C C19A C20A C20B 59.3(13) . . . . ? C24B C19A C20A C20B -170.3(12) . . . . ? C19B C19A C20A C21A -113.2(16) . . . . ? C18C C19A C20A C21A -55.8(19) . . . . ? C24B C19A C20A C21A 74.5(17) . . . . ? C20B C19A C20A C21A -115.1(19) . . . . ? C19B C19A C20A C21B -61.0(18) . . . . ? C18C C19A C20A C21B -4(2) . . . . ? C24B C19A C20A C21B 126.8(17) . . . . ? C20B C19A C20A C21B -62.9(17) . . . . ? C18C C19A C20A C19B 57.4(9) . . . . ? C24B C19A C20A C19B -172.2(12) . . . . ? C20B C19A C20A C19B -1.9(11) . . . . ? C20B C20A C21A C21B 3.8(15) . . . . ? C19A C20A C21A C21B 110.9(17) . . . . ? C19B C20A C21A C21B 59.6(18) . . . . ? C20B C20A C21A C22A -51.8(18) . . . . ? C21B C20A C21A C22A -55.6(13) . . . . ? C19A C20A C21A C22A 55(2) . . . . ? C19B C20A C21A C22A 4(2) . . . . ? C20B C20A C21A C22B -104.1(19) . . . . ? C21B C20A C21A C22B -107.9(18) . . . . ? C19A C20A C21A C22B 3(2) . . . . ? C19B C20A C21A C22B -48(3) . . . . ? C21B C21A C22A C22B -177.5(15) . . . . ? C20A C21A C22A C22B -115.6(16) . . . . ? C20A C21A C22A C21B 61.9(14) . . . . ? C22B C21A C22A C21B 177.5(15) . . . . ? C21B C21A C22A C23C -118.0(16) . . . . ? C20A C21A C22A C23C -56(2) . . . . ? C22B C21A C22A C23C 59.5(11) . . . . ? C22B C22A C23C C24A -96.7(14) . . . 5_575 ? C21B C22A C23C C24A 153.9(17) . . . 5_575 ? C21A C22A C23C C24A -153.2(15) . . . 5_575 ? C22B C22A C23C C18C 113.6(9) . . . . ? C21B C22A C23C C18C 4.1(19) . . . . ? C21A C22A C23C C18C 57.1(15) . . . . ? C22B C22A C23C C24B -84(2) . . . 5_575 ? C21B C22A C23C C24B 167(2) . . . 5_575 ? C21A C22A C23C C24B -140(2) . . . 5_575 ? C21B C22A C23C C22B -109.4(17) . . . . ? C21A C22A C23C C22B -56.5(12) . . . . ? C17B C18C C23C C24A -5(2) . . . 5_575 ? C19A C18C C23C C24A 158.5(16) . . . 5_575 ? C19B C18C C23C C24A -145.8(16) . . . 5_575 ? C17A C18C C23C C24A 29.1(18) . . . 5_575 ? C17B C18C C23C C22A 140.9(12) . . . . ? C19A C18C C23C C22A -55.1(10) . . . . ? C19B C18C C23C C22A 0.6(11) . . . . ? C17A C18C C23C C22A 175.5(10) . . . . ? C17B C18C C23C C24B -25(2) . . . 5_575 ? C19A C18C C23C C24B 138.9(17) . . . 5_575 ? C19B C18C C23C C24B -165.4(18) . . . 5_575 ? C17A C18C C23C C24B 9(2) . . . 5_575 ? C17B C18C C23C C22B -165.6(11) . . . . ? C19A C18C C23C C22B -1.6(11) . . . . ? C19B C18C C23C C22B 54.0(12) . . . . ? C17A C18C C23C C22B -131.1(11) . . . . ? C22B C17A C17B C18C -27(8) 5_575 . . . ? C16C C17A C17B C18C -128.1(15) . . . . ? C18C C17A C17B C16C 128.1(15) . . . . ? C22B C17A C17B C16C 101(7) 5_575 . . . ? C23C C18C C17B C17A 104(2) . . . . ? C19A C18C C17B C17A -57(3) . . . . ? C19B C18C C17B C17A -111(2) . . . . ? C23C C18C C17B C16C 9(2) . . . . ? C19A C18C C17B C16C -151.6(13) . . . . ? C19B C18C C17B C16C 154.1(15) . . . . ? C17A C18C C17B C16C -95(3) . . . . ? O2A C16C C17B C17A 101(3) . . . . ? O2B C16C C17B C17A 67(3) . . . . ? N1C C16C C17B C17A -107(2) . . . . ? O2A C16C C17B C18C -161.8(16) . . . . ? O2B C16C C17B C18C 164.0(15) . . . . ? N1C C16C C17B C18C -10(2) . . . . ? C17A C16C C17B C18C 97(3) . . . . ? C18C C19A C19B C20B -119.3(9) . . . . ? C20A C19A C19B C20B -1.6(9) . . . . ? C24B C19A C19B C20B 124(7) . . . . ? C20A C19A C19B C18C 117.7(7) . . . . ? C24B C19A C19B C18C -116(8) . . . . ? C20B C19A C19B C18C 119.3(9) . . . . ? C18C C19A C19B C20A -117.7(7) . . . . ? C24B C19A C19B C20A 126(8) . . . . ? C20B C19A C19B C20A 1.6(9) . . . . ? C17B C18C C19B C19A 126.4(10) . . . . ? C23C C18C C19B C19A -90.1(9) . . . . ? C17A C18C C19B C19A 94.8(10) . . . . ? C17B C18C C19B C20B -146.8(13) . . . . ? C23C C18C C19B C20B -3.3(16) . . . . ? C19A C18C C19B C20B 86.8(14) . . . . ? C17A C18C C19B C20B -178.4(12) . . . . ? C17B C18C C19B C20A 176.1(11) . . . . ? C23C C18C C19B C20A -40.4(11) . . . . ? C19A C18C C19B C20A 49.7(9) . . . . ? C17A C18C C19B C20A 144.5(10) . . . . ? C20B C20A C19B C19A -177.6(14) . . . . ? C21A C20A C19B C19A 93.0(18) . . . . ? C21B C20A C19B C19A 131.6(13) . . . . ? C21A C20A C19B C20B -89(2) . . . . ? C21B C20A C19B C20B -50.8(13) . . . . ? C19A C20A C19B C20B 177.6(14) . . . . ? C20B C20A C19B C18C 128.9(12) . . . . ? C21A C20A C19B C18C 40(2) . . . . ? C21B C20A C19B C18C 78.1(12) . . . . ? C19A C20A C19B C18C -53.5(8) . . . . ? C21B C22A C22B C21A -2.0(12) . . . . ? C23C C22A C22B C21A -125.4(8) . . . . ? C21B C22A C22B C17A 60(7) . . . 5_575 ? C23C C22A C22B C17A -63(7) . . . 5_575 ? C21A C22A C22B C17A 62(7) . . . 5_575 ? C21B C22A C22B C23C 123.4(12) . . . . ? C21A C22A C22B C23C 125.4(8) . . . . ? C21B C21A C22B C22A 2.5(15) . . . . ? C20A C21A C22B C22A 87.7(18) . . . . ? C21B C21A C22B C17A -168.2(14) . . . 5_575 ? C20A C21A C22B C17A -82.9(18) . . . 5_575 ? C22A C21A C22B C17A -170.7(13) . . . 5_575 ? C21B C21A C22B C23C -42.4(16) . . . . ? C20A C21A C22B C23C 42.9(19) . . . . ? C22A C21A C22B C23C -44.8(8) . . . . ? C24A C23C C22B C22A 105.0(16) 5_575 . . . ? C18C C23C C22B C22A -92.5(10) . . . . ? C24B C23C C22B C22A 126.6(17) 5_575 . . . ? C24A C23C C22B C21A 152.6(16) 5_575 . . . ? C22A C23C C22B C21A 47.6(10) . . . . ? C18C C23C C22B C21A -44.9(13) . . . . ? C24B C23C C22B C21A 174.3(17) 5_575 . . . ? C24A C23C C22B C17A -84.8(17) 5_575 . . 5_575 ? C22A C23C C22B C17A 170.2(13) . . . 5_575 ? C18C C23C C22B C17A 77.7(12) . . . 5_575 ? C24B C23C C22B C17A -63.2(18) 5_575 . . 5_575 ? C23C C24A C24B N1C -112.9(13) 5_575 . . 5_575 ? N1C C24A C24B C23C 112.9(13) 5_575 . . 5_575 ? C23C C24A C24B C19A 73(8) 5_575 . . . ? N1C C24A C24B C19A -175(8) 5_575 . . . ? C19B C19A C24B C24A 49(13) . . . . ? C18C C19A C24B C24A -64(9) . . . . ? C20A C19A C24B C24A 172(8) . . . . ? C20B C19A C24B C24A 163(8) . . . . ? C19B C19A C24B N1C -125(7) . . . 5_575 ? C18C C19A C24B N1C 123.0(13) . . . 5_575 ? C20A C19A C24B N1C -1.1(18) . . . 5_575 ? C20B C19A C24B N1C -10(3) . . . 5_575 ? C19B C19A C24B C23C 110(7) . . . 5_575 ? C18C C19A C24B C23C -2.4(17) . . . 5_575 ? C20A C19A C24B C23C -126.5(12) . . . 5_575 ? C20B C19A C24B C23C -135.7(14) . . . 5_575 ? C20A C21A C21B C22A -119.6(8) . . . . ? C22B C21A C21B C22A -2.1(12) . . . . ? C20A C21A C21B C20B -3.0(12) . . . . ? C22A C21A C21B C20B 116.6(12) . . . . ? C22B C21A C21B C20B 114.6(13) . . . . ? C22A C21A C21B C20A 119.6(8) . . . . ? C22B C21A C21B C20A 117.6(12) . . . . ? C22B C22A C21B C21A 2.6(15) . . . . ? C23C C22A C21B C21A 90.6(18) . . . . ? C22B C22A C21B C20B -94.2(19) . . . . ? C23C C22A C21B C20B -6(3) . . . . ? C21A C22A C21B C20B -96.8(16) . . . . ? C22B C22A C21B C20A -47.4(17) . . . . ? C23C C22A C21B C20A 41(2) . . . . ? C21A C22A C21B C20A -50.0(11) . . . . ? C20B C20A C21B C21A -176.0(16) . . . . ? C19A C20A C21B C21A -95.2(18) . . . . ? C19B C20A C21B C21A -133.7(12) . . . . ? C20B C20A C21B C22A -119.7(15) . . . . ? C21A C20A C21B C22A 56.3(13) . . . . ? C19A C20A C21B C22A -39(2) . . . . ? C19B C20A C21B C22A -77.4(14) . . . . ? C21A C20A C21B C20B 176.0(16) . . . . ? C19A C20A C21B C20B 80.8(16) . . . . ? C19B C20A C21B C20B 42.3(9) . . . . ? C21A C20A C20B C19B 117.4(11) . . . . ? C21B C20A C20B C19B 120.5(10) . . . . ? C19A C20A C20B C19B -1.7(10) . . . . ? C21A C20A C20B C21B -3.1(12) . . . . ? C19A C20A C20B C21B -122.2(10) . . . . ? C19B C20A C20B C21B -120.5(10) . . . . ? C21A C20A C20B C19A 119.1(12) . . . . ? C21B C20A C20B C19A 122.2(10) . . . . ? C19B C20A C20B C19A 1.7(10) . . . . ? C19A C19B C20B C20A 2.1(12) . . . . ? C18C C19B C20B C20A -63.9(14) . . . . ? C19A C19B C20B C21B 67.4(15) . . . . ? C18C C19B C20B C21B 1(2) . . . . ? C20A C19B C20B C21B 65.3(15) . . . . ? C18C C19B C20B C19A -66.0(11) . . . . ? C20A C19B C20B C19A -2.1(12) . . . . ? C21A C21B C20B C20A 3.6(14) . . . . ? C22A C21B C20B C20A 78.4(18) . . . . ? C21A C21B C20B C19B -71.9(18) . . . . ? C22A C21B C20B C19B 3(2) . . . . ? C20A C21B C20B C19B -75.5(14) . . . . ? C21A C21B C20B C19A -36.6(15) . . . . ? C22A C21B C20B C19A 38.2(18) . . . . ? C20A C21B C20B C19A -40.1(8) . . . . ? C19B C19A C20B C20A -177.3(16) . . . . ? C18C C19A C20B C20A -125.0(12) . . . . ? C24B C19A C20B C20A 15.3(19) . . . . ? C18C C19A C20B C19B 52.2(9) . . . . ? C20A C19A C20B C19B 177.3(16) . . . . ? C24B C19A C20B C19B -167.4(18) . . . . ? C19B C19A C20B C21B -123.9(13) . . . . ? C18C C19A C20B C21B -71.7(10) . . . . ? C20A C19A C20B C21B 53.4(12) . . . . ? C24B C19A C20B C21B 68.7(18) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.322 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.060 # Attachment 'I-1o.cif' data_Cao5(cube) _database_code_depnum_ccdc_archive 'CCDC 787300' #TrackingRef 'I-1o.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol:2(Isoquinolin-3(2H)-one) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2 , 2(C9 H7 N O)' _chemical_formula_sum 'C48 H36 N2 O4' _chemical_formula_weight 704.79 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 orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' 'x-1/2, y-1/2, -z-1/2' _cell_length_a 25.4736(9) _cell_length_b 8.5626(3) _cell_length_c 16.9318(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3693.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 260(2) _cell_measurement_reflns_used 2743 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 20.33 _exptl_crystal_description cube _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 260(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27377 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4601 _reflns_number_gt 3130 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0506P)^2^+0.9081P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4589 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1214 _refine_ls_wR_factor_gt 0.1009 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 0.36370(4) 0.44152(12) 0.35275(6) 0.0475(3) Uani 1 1 d . . . H1O1 H 0.3868 0.4502 0.3862 0.071 Uiso 1 1 calc R . . C1 C 0.47336(5) 0.56655(15) 0.25769(8) 0.0369(3) Uani 1 1 d . . . C2 C 0.42726(5) 0.56250(15) 0.27094(8) 0.0374(3) Uani 1 1 d . . . C3 C 0.37094(5) 0.55601(15) 0.29337(8) 0.0351(3) Uani 1 1 d . . . C4 C 0.33705(5) 0.50647(15) 0.22242(8) 0.0353(3) Uani 1 1 d . . . C5 C 0.34687(6) 0.56328(18) 0.14743(9) 0.0461(3) Uani 1 1 d . . . H5 H 0.3749 0.6310 0.1393 0.055 Uiso 1 1 calc R . . C6 C 0.31535(6) 0.5204(2) 0.08414(9) 0.0554(4) Uani 1 1 d . . . H6 H 0.3224 0.5590 0.0339 0.066 Uiso 1 1 calc R . . C7 C 0.27389(7) 0.4214(2) 0.09560(10) 0.0615(5) Uani 1 1 d . . . H7 H 0.2527 0.3927 0.0533 0.074 Uiso 1 1 calc R . . C8 C 0.26371(7) 0.3647(2) 0.16985(11) 0.0681(5) Uani 1 1 d . . . H8 H 0.2355 0.2977 0.1777 0.082 Uiso 1 1 calc R . . C9 C 0.29510(6) 0.4064(2) 0.23326(9) 0.0533(4) Uani 1 1 d . . . H9 H 0.2879 0.3669 0.2833 0.064 Uiso 1 1 calc R . . C10 C 0.35290(5) 0.71830(16) 0.32133(8) 0.0365(3) Uani 1 1 d . . . C11 C 0.37026(6) 0.85430(17) 0.28532(10) 0.0492(4) Uani 1 1 d . . . H11 H 0.3947 0.8486 0.2446 0.059 Uiso 1 1 calc R . . C12 C 0.35150(7) 0.9989(2) 0.30946(11) 0.0611(4) Uani 1 1 d . . . H12 H 0.3635 1.0894 0.2850 0.073 Uiso 1 1 calc R . . C13 C 0.31537(7) 1.0084(2) 0.36913(12) 0.0657(5) Uani 1 1 d . . . H13 H 0.3028 1.1053 0.3853 0.079 Uiso 1 1 calc R . . C14 C 0.29784(7) 0.8749(2) 0.40494(11) 0.0679(5) Uani 1 1 d . . . H14 H 0.2731 0.8813 0.4452 0.081 Uiso 1 1 calc R . . C15 C 0.31659(6) 0.7304(2) 0.38160(9) 0.0516(4) Uani 1 1 d . . . H15 H 0.3046 0.6406 0.4067 0.062 Uiso 1 1 calc R . . O2 O 0.43820(4) 0.55394(13) -0.03495(7) 0.0616(3) Uani 1 1 d . . . N1 N 0.49554(5) 0.69230(14) 0.04050(7) 0.0473(3) Uani 1 1 d . . . H1N1 H 0.5172 0.6156 0.0363 0.057 Uiso 1 1 calc R . . C16 C 0.44769(6) 0.67941(18) 0.00303(8) 0.0455(3) Uani 1 1 d . . . C17 C 0.41358(6) 0.80497(18) 0.01204(9) 0.0504(4) Uani 1 1 d . . . H17 H 0.3811 0.8026 -0.0131 0.060 Uiso 1 1 calc R . . C18 C 0.42683(6) 0.93381(17) 0.05776(9) 0.0470(4) Uani 1 1 d . . . C19 C 0.39209(8) 1.0613(2) 0.07105(12) 0.0697(5) Uani 1 1 d . . . H19 H 0.3587 1.0602 0.0490 0.084 Uiso 1 1 calc R . . C20 C 0.40750(10) 1.1839(2) 0.11564(14) 0.0872(7) Uani 1 1 d . . . H20 H 0.3843 1.2662 0.1236 0.105 Uiso 1 1 calc R . . C21 C 0.45733(10) 1.1907(2) 0.15024(13) 0.0843(7) Uani 1 1 d . . . H21 H 0.4668 1.2772 0.1803 0.101 Uiso 1 1 calc R . . C22 C 0.49160(8) 1.0724(2) 0.14017(11) 0.0663(5) Uani 1 1 d . . . H22 H 0.5247 1.0771 0.1633 0.080 Uiso 1 1 calc R . . C23 C 0.47709(6) 0.94055(17) 0.09425(8) 0.0463(3) Uani 1 1 d . . . C24 C 0.51047(6) 0.81524(18) 0.08273(9) 0.0484(4) Uani 1 1 d . . . H24 H 0.5439 0.8171 0.1049 0.058 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 0.0396(5) 0.0503(6) 0.0526(6) 0.0167(5) -0.0087(4) -0.0083(5) C1 0.0312(6) 0.0333(7) 0.0463(7) -0.0002(6) -0.0028(5) 0.0005(5) C2 0.0312(6) 0.0347(7) 0.0461(7) -0.0008(6) -0.0042(5) 0.0008(5) C3 0.0278(6) 0.0362(7) 0.0413(7) 0.0046(6) -0.0004(5) -0.0005(5) C4 0.0271(6) 0.0352(7) 0.0436(7) -0.0040(6) -0.0008(5) 0.0048(5) C5 0.0426(7) 0.0469(8) 0.0490(8) 0.0033(7) -0.0032(6) -0.0021(6) C6 0.0600(10) 0.0617(10) 0.0444(8) -0.0012(7) -0.0083(7) 0.0038(8) C7 0.0495(9) 0.0776(12) 0.0575(10) -0.0181(9) -0.0134(8) -0.0015(9) C8 0.0474(9) 0.0897(14) 0.0672(11) -0.0166(10) -0.0018(8) -0.0265(9) C9 0.0427(8) 0.0676(10) 0.0497(9) -0.0054(8) 0.0043(7) -0.0162(7) C10 0.0289(6) 0.0426(7) 0.0381(7) -0.0028(6) -0.0046(5) 0.0009(5) C11 0.0483(8) 0.0428(8) 0.0566(9) 0.0020(7) 0.0045(7) 0.0038(7) C12 0.0619(10) 0.0420(9) 0.0793(12) -0.0011(9) -0.0077(9) 0.0057(8) C13 0.0584(10) 0.0604(11) 0.0783(12) -0.0261(10) -0.0094(9) 0.0169(9) C14 0.0594(10) 0.0804(14) 0.0640(11) -0.0245(10) 0.0107(9) 0.0099(10) C15 0.0469(8) 0.0608(10) 0.0472(8) -0.0061(7) 0.0057(6) -0.0004(7) O2 0.0618(7) 0.0522(7) 0.0709(7) -0.0241(6) -0.0267(6) 0.0168(5) N1 0.0494(7) 0.0438(7) 0.0487(7) -0.0105(6) -0.0124(5) 0.0141(6) C16 0.0498(8) 0.0450(8) 0.0416(7) -0.0065(6) -0.0096(6) 0.0085(7) C17 0.0493(8) 0.0478(9) 0.0539(9) -0.0034(7) -0.0105(7) 0.0102(7) C18 0.0560(9) 0.0410(8) 0.0439(8) 0.0024(6) 0.0007(6) 0.0099(7) C19 0.0742(12) 0.0562(11) 0.0785(13) -0.0088(9) -0.0051(10) 0.0256(9) C20 0.1094(18) 0.0583(12) 0.0940(15) -0.0218(11) -0.0063(13) 0.0374(12) C21 0.1189(18) 0.0502(11) 0.0839(14) -0.0257(10) -0.0174(13) 0.0168(11) C22 0.0888(13) 0.0494(10) 0.0608(10) -0.0126(8) -0.0164(9) 0.0060(9) C23 0.0620(9) 0.0389(8) 0.0381(7) -0.0006(6) -0.0039(7) 0.0047(7) C24 0.0553(9) 0.0453(8) 0.0446(8) -0.0052(7) -0.0132(7) 0.0053(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 O1 C3 1.4163(16) . ? O1 H1O1 0.8200 . ? C1 C2 1.1961(17) . ? C1 C1 1.382(2) 3_655 ? C2 C3 1.4851(17) . ? C3 C10 1.5383(19) . ? C3 C4 1.5390(18) . ? C4 C9 1.382(2) . ? C4 C5 1.383(2) . ? C5 C6 1.388(2) . ? C5 H5 0.9300 . ? C6 C7 1.368(2) . ? C6 H6 0.9300 . ? C7 C8 1.372(3) . ? C7 H7 0.9300 . ? C8 C9 1.385(2) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.3811(19) . ? C10 C11 1.387(2) . ? C11 C12 1.388(2) . ? C11 H11 0.9300 . ? C12 C13 1.369(3) . ? C12 H12 0.9300 . ? C13 C14 1.369(3) . ? C13 H13 0.9300 . ? C14 C15 1.384(2) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 C16 1.2752(17) . ? N1 C24 1.3281(18) . ? N1 C16 1.3786(18) . ? N1 H1N1 0.8600 . ? C16 C17 1.391(2) . ? C17 C18 1.389(2) . ? C17 H17 0.9300 . ? C18 C23 1.423(2) . ? C18 C19 1.423(2) . ? C19 C20 1.351(3) . ? C19 H19 0.9300 . ? C20 C21 1.399(3) . ? C20 H20 0.9300 . ? C21 C22 1.348(3) . ? C21 H21 0.9300 . ? C22 C23 1.420(2) . ? C22 H22 0.9300 . ? C23 C24 1.383(2) . ? C24 H24 0.9300 . ? 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 C3 O1 H1O1 109.5 . . ? C2 C1 C1 178.34(9) . 3_655 ? C1 C2 C3 175.96(14) . . ? O1 C3 C2 109.46(10) . . ? O1 C3 C10 111.59(11) . . ? C2 C3 C10 109.48(10) . . ? O1 C3 C4 106.88(10) . . ? C2 C3 C4 110.65(11) . . ? C10 C3 C4 108.76(10) . . ? C9 C4 C5 118.69(13) . . ? C9 C4 C3 120.07(12) . . ? C5 C4 C3 121.23(12) . . ? C4 C5 C6 120.74(14) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C6 C5 120.05(16) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 119.67(15) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C7 C8 C9 120.64(16) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C4 C9 C8 120.21(15) . . ? C4 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C15 C10 C11 118.38(14) . . ? C15 C10 C3 119.69(13) . . ? C11 C10 C3 121.87(12) . . ? C10 C11 C12 120.62(15) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 120.13(17) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 119.73(16) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.50(16) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C10 C15 C14 120.62(16) . . ? C10 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C24 N1 C16 124.36(13) . . ? C24 N1 H1N1 117.8 . . ? C16 N1 H1N1 117.8 . . ? O2 C16 N1 117.85(13) . . ? O2 C16 C17 126.03(14) . . ? N1 C16 C17 116.10(13) . . ? C18 C17 C16 121.55(14) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C17 C18 C23 119.52(13) . . ? C17 C18 C19 123.10(15) . . ? C23 C18 C19 117.37(15) . . ? C20 C19 C18 120.24(19) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 122.01(18) . . ? C19 C20 H20 119.0 . . ? C21 C20 H20 119.0 . . ? C22 C21 C20 120.18(18) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 119.89(18) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C24 C23 C22 122.28(15) . . ? C24 C23 C18 117.42(13) . . ? C22 C23 C18 120.30(14) . . ? N1 C24 C23 120.99(14) . . ? N1 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? 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 C1 C1 C2 C3 84(7) 3_655 . . . ? C1 C2 C3 O1 -39(2) . . . . ? C1 C2 C3 C10 83(2) . . . . ? C1 C2 C3 C4 -157(2) . . . . ? O1 C3 C4 C9 21.68(17) . . . . ? C2 C3 C4 C9 140.79(13) . . . . ? C10 C3 C4 C9 -98.93(15) . . . . ? O1 C3 C4 C5 -159.92(12) . . . . ? C2 C3 C4 C5 -40.81(17) . . . . ? C10 C3 C4 C5 79.48(15) . . . . ? C9 C4 C5 C6 -0.2(2) . . . . ? C3 C4 C5 C6 -178.62(13) . . . . ? C4 C5 C6 C7 0.3(2) . . . . ? C5 C6 C7 C8 -0.1(3) . . . . ? C6 C7 C8 C9 -0.2(3) . . . . ? C5 C4 C9 C8 -0.1(2) . . . . ? C3 C4 C9 C8 178.36(15) . . . . ? C7 C8 C9 C4 0.3(3) . . . . ? O1 C3 C10 C15 -23.31(16) . . . . ? C2 C3 C10 C15 -144.64(13) . . . . ? C4 C3 C10 C15 94.35(14) . . . . ? O1 C3 C10 C11 159.68(12) . . . . ? C2 C3 C10 C11 38.35(17) . . . . ? C4 C3 C10 C11 -82.66(15) . . . . ? C15 C10 C11 C12 0.0(2) . . . . ? C3 C10 C11 C12 177.06(14) . . . . ? C10 C11 C12 C13 -0.2(3) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? C12 C13 C14 C15 0.4(3) . . . . ? C11 C10 C15 C14 0.4(2) . . . . ? C3 C10 C15 C14 -176.70(14) . . . . ? C13 C14 C15 C10 -0.6(3) . . . . ? C24 N1 C16 O2 -179.28(15) . . . . ? C24 N1 C16 C17 -0.7(2) . . . . ? O2 C16 C17 C18 177.00(16) . . . . ? N1 C16 C17 C18 -1.4(2) . . . . ? C16 C17 C18 C23 2.1(2) . . . . ? C16 C17 C18 C19 -177.24(17) . . . . ? C17 C18 C19 C20 -179.47(19) . . . . ? C23 C18 C19 C20 1.2(3) . . . . ? C18 C19 C20 C21 -0.1(4) . . . . ? C19 C20 C21 C22 -0.5(4) . . . . ? C20 C21 C22 C23 0.1(3) . . . . ? C21 C22 C23 C24 -179.30(19) . . . . ? C21 C22 C23 C18 1.0(3) . . . . ? C17 C18 C23 C24 -0.7(2) . . . . ? C19 C18 C23 C24 178.68(16) . . . . ? C17 C18 C23 C22 179.03(15) . . . . ? C19 C18 C23 C22 -1.6(2) . . . . ? C16 N1 C24 C23 2.1(2) . . . . ? C22 C23 C24 N1 178.93(15) . . . . ? C18 C23 C24 N1 -1.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.168 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.035 # Attachment 'I-1od.cif' data_data_Cao5(cube)_dimer _database_code_depnum_ccdc_archive 'CCDC 787301' #TrackingRef 'I-1od.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol:2(dimer of Isoquinolin-3(2H)-one) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2 , 2(C9 H7 N O)' _chemical_formula_sum 'C48 H36 N2 O4' _chemical_formula_weight 704.79 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 orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' 'x-1/2, y-1/2, -z-1/2' _cell_length_a 25.479(3) _cell_length_b 8.1154(8) _cell_length_c 17.987(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3719.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 286(2) _cell_measurement_reflns_used 1363 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 20.05 _exptl_crystal_description cube _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 286(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11003 _diffrn_reflns_av_R_equivalents 0.0447 _diffrn_reflns_av_sigmaI/netI 0.0510 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.69 _reflns_number_total 3524 _reflns_number_gt 1655 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0040(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3524 _refine_ls_number_parameters 345 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1681 _refine_ls_R_factor_gt 0.0901 _refine_ls_wR_factor_ref 0.3356 _refine_ls_wR_factor_gt 0.2565 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.003 _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 0.36656(11) 0.4148(4) 0.34246(17) 0.0687(10) Uani 1 1 d . . . H1O1 H 0.3839 0.4307 0.3802 0.103 Uiso 1 1 calc R . . C1 C 0.47362(14) 0.5758(5) 0.2584(2) 0.0620(11) Uani 1 1 d . . . C2 C 0.42798(14) 0.5691(5) 0.2738(2) 0.0616(12) Uani 1 1 d . . . C3 C 0.37210(13) 0.5511(5) 0.2940(2) 0.0542(11) Uani 1 1 d . . . C4 C 0.33871(13) 0.5147(5) 0.2244(2) 0.0530(10) Uani 1 1 d . . . C5 C 0.35389(16) 0.5649(6) 0.1545(3) 0.0703(13) Uani 1 1 d . . . H5 H 0.3857 0.6194 0.1482 0.084 Uiso 1 1 calc R . . C6 C 0.32176(19) 0.5346(7) 0.0928(3) 0.0853(15) Uani 1 1 d . . . H6 H 0.3321 0.5690 0.0457 0.102 Uiso 1 1 calc R . . C7 C 0.27455(19) 0.4532(7) 0.1024(3) 0.0857(15) Uani 1 1 d . . . H7 H 0.2531 0.4325 0.0617 0.103 Uiso 1 1 calc R . . C8 C 0.25937(17) 0.4030(6) 0.1720(3) 0.0775(14) Uani 1 1 d . . . H8 H 0.2276 0.3484 0.1785 0.093 Uiso 1 1 calc R . . C9 C 0.29125(15) 0.4335(5) 0.2325(3) 0.0660(12) Uani 1 1 d . . . H9 H 0.2807 0.3991 0.2794 0.079 Uiso 1 1 calc R . . C10 C 0.35157(13) 0.7075(5) 0.3299(2) 0.0574(11) Uani 1 1 d . . . C11 C 0.36148(17) 0.8593(6) 0.2975(3) 0.0777(14) Uani 1 1 d . . . H11 H 0.3822 0.8659 0.2551 0.093 Uiso 1 1 calc R . . C12 C 0.3400(2) 1.0045(7) 0.3291(4) 0.102(2) Uani 1 1 d . . . H12 H 0.3466 1.1075 0.3084 0.123 Uiso 1 1 calc R . . C13 C 0.3081(2) 0.9879(11) 0.3930(4) 0.114(2) Uani 1 1 d . . . H13 H 0.2935 1.0814 0.4145 0.136 Uiso 1 1 calc R . . C14 C 0.2985(2) 0.8378(11) 0.4234(4) 0.115(2) Uani 1 1 d . . . H14 H 0.2774 0.8286 0.4654 0.138 Uiso 1 1 calc R . . C15 C 0.32003(17) 0.7013(7) 0.3921(3) 0.0815(14) Uani 1 1 d . . . H15 H 0.3132 0.5993 0.4136 0.098 Uiso 1 1 calc R . . O2A O 0.5478(4) 0.3427(17) 0.0525(6) 0.093(3) Uani 0.50 1 d P . . N1A N 0.4915(5) 0.232(2) -0.0296(9) 0.092(4) Uani 0.50 1 d P . . C16A C 0.5324(5) 0.220(2) 0.0171(7) 0.086(3) Uani 0.50 1 d P . . C17A C 0.5594(5) 0.054(3) 0.0194(9) 0.086(4) Uani 0.50 1 d P . . C18A C 0.5694(4) -0.002(2) -0.0570(8) 0.083(4) Uani 0.50 1 d P . . C19A C 0.6118(3) -0.0628(13) -0.0757(6) 0.077(3) Uani 0.50 1 d P . . C20A C 0.6132(4) -0.1361(12) -0.1432(7) 0.086(3) Uani 0.50 1 d P . . C21A C 0.5688(4) -0.1387(12) -0.1920(7) 0.091(3) Uani 0.50 1 d P . . C22A C 0.5243(5) -0.0630(19) -0.1703(6) 0.080(3) Uani 0.50 1 d P . . C23A C 0.5220(6) -0.0076(18) -0.1155(16) 0.121(9) Uani 0.50 1 d P . . C24A C 0.4806(6) 0.0758(17) -0.0663(6) 0.076(3) Uani 0.50 1 d P . . O2B O 0.5683(2) 0.4708(10) 0.0373(4) 0.0751(18) Uani 0.50 1 d P . . N1B N 0.5068(3) 0.3619(13) -0.0381(5) 0.076(2) Uani 0.50 1 d P . . C16B C 0.5489(5) 0.346(3) 0.0060(8) 0.073(4) Uani 0.50 1 d P . . C17B C 0.5670(4) 0.178(2) 0.0214(6) 0.071(3) Uani 0.50 1 d P . . C18B C 0.5551(11) 0.064(3) -0.0296(14) 0.176(13) Uani 0.50 1 d P . . C23B C 0.5209(7) 0.069(3) -0.0878(11) 0.116(6) Uani 0.50 1 d P . . C24B C 0.4799(5) 0.208(3) -0.0652(9) 0.080(4) Uani 0.50 1 d P . . C19B C 0.5583(8) -0.132(3) -0.0017(11) 0.169(8) Uani 0.50 1 d P . . C20B C 0.5574(8) -0.227(2) -0.0689(11) 0.166(6) Uani 0.50 1 d P . . C21B C 0.5129(8) -0.203(4) -0.1157(11) 0.191(10) Uani 0.50 1 d P . . C22B C 0.5297(7) 0.077(4) 0.0858(13) 0.213(11) Uani 0.50 1 d P . . 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 0.0518(17) 0.075(2) 0.079(2) 0.0126(16) -0.0137(14) -0.0121(13) C1 0.0349(19) 0.076(3) 0.075(3) 0.001(2) -0.0085(18) 0.0003(17) C2 0.036(2) 0.071(3) 0.078(3) -0.003(2) -0.0081(18) 0.0006(17) C3 0.0327(18) 0.059(2) 0.071(3) 0.004(2) -0.0035(17) -0.0052(15) C4 0.0328(17) 0.061(2) 0.065(3) -0.004(2) -0.0040(17) 0.0021(16) C5 0.045(2) 0.091(3) 0.075(3) 0.005(3) -0.001(2) -0.004(2) C6 0.072(3) 0.117(4) 0.067(3) 0.000(3) -0.007(2) 0.010(3) C7 0.062(3) 0.109(4) 0.086(4) -0.019(3) -0.021(3) 0.008(3) C8 0.050(2) 0.102(4) 0.081(3) -0.016(3) -0.015(2) -0.008(2) C9 0.043(2) 0.081(3) 0.073(3) -0.004(2) -0.004(2) -0.0081(19) C10 0.0332(18) 0.064(3) 0.075(3) -0.011(2) -0.0116(18) -0.0022(17) C11 0.060(3) 0.072(3) 0.101(4) -0.008(3) -0.021(2) 0.004(2) C12 0.084(4) 0.065(3) 0.157(6) -0.017(4) -0.059(4) 0.006(3) C13 0.050(3) 0.150(6) 0.141(6) -0.076(5) -0.018(3) 0.019(4) C14 0.069(4) 0.141(6) 0.136(6) -0.057(5) 0.013(3) -0.017(4) C15 0.055(3) 0.099(4) 0.091(3) -0.030(3) 0.005(2) -0.008(2) O2A 0.055(5) 0.118(9) 0.106(7) -0.018(8) -0.023(6) 0.021(5) N1A 0.040(6) 0.123(11) 0.113(11) -0.032(10) -0.021(6) 0.018(6) C16A 0.064(7) 0.122(11) 0.070(7) 0.000(9) -0.022(6) 0.037(8) C17A 0.066(7) 0.110(12) 0.081(10) 0.006(10) 0.010(7) 0.039(7) C18A 0.054(6) 0.131(12) 0.062(8) 0.015(9) 0.003(5) 0.022(7) C19A 0.031(4) 0.106(7) 0.093(7) 0.047(6) -0.009(4) 0.006(4) C20A 0.064(6) 0.072(6) 0.121(9) 0.043(6) -0.032(6) 0.001(5) C21A 0.081(7) 0.064(6) 0.127(9) 0.037(6) -0.026(6) -0.006(5) C22A 0.092(8) 0.092(8) 0.057(6) 0.014(6) 0.001(6) -0.007(7) C23A 0.066(8) 0.074(9) 0.22(3) -0.042(11) 0.049(13) 0.010(6) C24A 0.093(10) 0.059(7) 0.076(7) -0.022(6) 0.019(6) -0.012(7) O2B 0.049(3) 0.095(5) 0.081(5) 0.002(5) -0.016(3) 0.008(3) N1B 0.064(5) 0.097(6) 0.066(5) -0.002(5) -0.028(4) 0.002(5) C16B 0.046(6) 0.103(12) 0.070(8) 0.000(8) -0.010(6) 0.013(6) C17B 0.052(6) 0.093(9) 0.069(7) 0.005(7) -0.021(5) 0.023(6) C18B 0.22(2) 0.18(2) 0.124(18) -0.068(16) -0.118(17) 0.117(17) C23B 0.076(10) 0.177(19) 0.096(11) 0.004(12) -0.047(9) 0.033(12) C24B 0.043(7) 0.111(13) 0.085(11) 0.000(10) -0.009(6) -0.005(7) C19B 0.162(18) 0.21(2) 0.131(15) -0.056(16) -0.037(13) 0.065(16) C20B 0.176(18) 0.175(17) 0.148(15) 0.002(13) -0.015(13) 0.031(13) C21B 0.119(14) 0.32(3) 0.135(14) -0.038(18) -0.021(11) 0.059(17) C22B 0.092(13) 0.37(4) 0.17(2) 0.05(2) -0.075(14) 0.020(19) _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 C3 1.415(5) . ? O1 H1O1 0.8200 . ? C1 C2 1.197(5) . ? C1 C1 1.378(7) 3_655 ? C2 C3 1.477(5) . ? C3 C10 1.517(6) . ? C3 C4 1.543(5) . ? C4 C5 1.377(6) . ? C4 C9 1.384(5) . ? C5 C6 1.401(6) . ? C5 H5 0.9300 . ? C6 C7 1.383(7) . ? C6 H6 0.9300 . ? C7 C8 1.372(7) . ? C7 H7 0.9300 . ? C8 C9 1.379(6) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.379(6) . ? C10 C11 1.386(6) . ? C11 C12 1.419(7) . ? C11 H11 0.9300 . ? C12 C13 1.413(9) . ? C12 H12 0.9300 . ? C13 C14 1.358(9) . ? C13 H13 0.9300 . ? C14 C15 1.358(8) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2A C16B 0.837(12) . ? O2A O2B 1.195(14) . ? O2A C16A 1.245(18) . ? O2A C17B 1.528(18) . ? N1A C24B 0.733(14) . ? N1A N1B 1.136(18) . ? N1A C16A 1.340(17) . ? N1A C24A 1.454(19) . ? N1A C19B 1.61(3) 5_655 ? N1A C23B 1.84(3) . ? N1A C16B 1.85(2) . ? C16A C17B 0.950(12) . ? C16A C16B 1.12(2) . ? C16A C17A 1.51(2) . ? C16A C18B 1.63(2) . ? C16A N1B 1.653(17) . ? C16A C22B 1.70(3) . ? C16A C24B 1.997(19) . ? C17A C18B 0.89(2) . ? C17A C17B 1.024(16) . ? C17A C22B 1.43(3) . ? C17A C18A 1.47(2) . ? C17A C19B 1.56(3) . ? C17A C24A 1.69(2) 5_655 ? C18A C18B 0.81(2) . ? C18A C19A 1.236(14) . ? C18A C23B 1.470(19) . ? C18A C19B 1.48(3) . ? C18A C23A 1.60(3) . ? C18A C20B 1.87(3) . ? C18A C17B 2.03(2) . ? C19A C20A 1.351(15) . ? C19A C20B 1.93(2) . ? C19A C18B 1.96(3) . ? C19A C19B 1.99(3) . ? C20A C21A 1.434(14) . ? C21A C22A 1.347(17) . ? C22A C23A 1.08(2) . ? C22A C21B 1.53(3) . ? C22A C23B 1.83(2) . ? C23A C23B 0.80(2) . ? C23A C22B 1.53(3) 5_655 ? C23A C24A 1.53(2) . ? C23A C21B 1.61(3) . ? C23A C18B 1.85(3) . ? C24A C24B 1.07(2) . ? C24A C23B 1.10(2) . ? C24A C22B 1.32(3) 5_655 ? C24A C19B 1.64(2) 5_655 ? C24A C17A 1.69(2) 5_655 ? C24A C18B 2.01(3) . ? O2B C16B 1.26(2) . ? N1B C16B 1.340(15) . ? N1B C24B 1.51(2) . ? C16B C17B 1.47(2) . ? C17B C18B 1.34(2) . ? C17B C22B 1.71(3) . ? C18B C23B 1.36(2) . ? C18B C19B 1.67(4) . ? C23B C24B 1.59(3) . ? C23B C22B 1.75(3) 5_655 ? C24B C19B 1.67(3) 5_655 ? C19B C20B 1.44(2) . ? C19B N1A 1.61(3) 5_655 ? C19B C24A 1.64(2) 5_655 ? C19B C24B 1.67(3) 5_655 ? C20B C21B 1.42(2) . ? C21B C22B 1.59(3) 5_655 ? C22B C24A 1.32(3) 5_655 ? C22B C23A 1.53(3) 5_655 ? C22B C21B 1.59(3) 5_655 ? C22B C23B 1.75(3) 5_655 ? 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 C3 O1 H1O1 109.5 . . ? C2 C1 C1 177.3(3) . 3_655 ? C1 C2 C3 176.8(5) . . ? O1 C3 C2 109.0(3) . . ? O1 C3 C10 110.9(3) . . ? C2 C3 C10 110.8(3) . . ? O1 C3 C4 107.2(3) . . ? C2 C3 C4 110.5(3) . . ? C10 C3 C4 108.4(3) . . ? C5 C4 C9 118.8(4) . . ? C5 C4 C3 122.0(3) . . ? C9 C4 C3 119.2(4) . . ? C4 C5 C6 120.5(4) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C5 119.5(5) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C8 C7 C6 120.1(4) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.0(4) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C8 C9 C4 121.1(4) . . ? C8 C9 H9 119.4 . . ? C4 C9 H9 119.4 . . ? C15 C10 C11 118.6(4) . . ? C15 C10 C3 121.1(4) . . ? C11 C10 C3 120.1(4) . . ? C10 C11 C12 120.0(5) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 117.9(6) . . ? C13 C12 H12 121.1 . . ? C11 C12 H12 121.1 . . ? C14 C13 C12 121.2(6) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C15 C14 C13 119.4(6) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C10 122.8(6) . . ? C14 C15 H15 118.6 . . ? C10 C15 H15 118.6 . . ? C16B O2A O2B 74(2) . . ? C16B O2A C16A 61.7(18) . . ? O2B O2A C16A 135.7(16) . . ? C16B O2A C17B 69.8(18) . . ? O2B O2A C17B 122.4(10) . . ? C16A O2A C17B 38.4(6) . . ? C24B N1A N1B 106(3) . . ? C24B N1A C16A 148(3) . . ? N1B N1A C16A 83.3(12) . . ? C24B N1A C24A 45(2) . . ? N1B N1A C24A 144.4(17) . . ? C16A N1A C24A 111.9(14) . . ? C24B N1A C19B 81(2) . 5_655 ? N1B N1A C19B 141.8(14) . 5_655 ? C16A N1A C19B 111.0(15) . 5_655 ? C24A N1A C19B 64.5(11) . 5_655 ? C24B N1A C23B 58(2) . . ? N1B N1A C23B 116.8(14) . . ? C16A N1A C23B 89.4(10) . . ? C24A N1A C23B 36.6(8) . . ? C19B N1A C23B 99.1(14) 5_655 . ? C24B N1A C16B 139(3) . . ? N1B N1A C16B 46.2(8) . . ? C16A N1A C16B 37.2(9) . . ? C24A N1A C16B 138.4(11) . . ? C19B N1A C16B 139.2(13) 5_655 . ? C23B N1A C16B 103.7(9) . . ? C17B C16A C16B 89.6(18) . . ? C17B C16A O2A 87.2(14) . . ? C16B C16A O2A 41.0(9) . . ? C17B C16A N1A 143.0(16) . . ? C16B C16A N1A 96.7(16) . . ? O2A C16A N1A 120.7(15) . . ? C17B C16A C17A 41.8(10) . . ? C16B C16A C17A 130.1(15) . . ? O2A C16A C17A 123.6(13) . . ? N1A C16A C17A 115.7(14) . . ? C17B C16A C18B 55.4(13) . . ? C16B C16A C18B 119(2) . . ? O2A C16A C18B 140.7(14) . . ? N1A C16A C18B 90.5(12) . . ? C17A C16A C18B 32.7(9) . . ? C17B C16A N1B 131.7(18) . . ? C16B C16A N1B 53.7(11) . . ? O2A C16A N1B 82.9(12) . . ? N1A C16A N1B 43.0(9) . . ? C17A C16A N1B 144.6(11) . . ? C18B C16A N1B 111.9(12) . . ? C17B C16A C22B 74.4(14) . . ? C16B C16A C22B 140.0(17) . . ? O2A C16A C22B 100.6(16) . . ? N1A C16A C22B 118.3(15) . . ? C17A C16A C22B 52.4(12) . . ? C18B C16A C22B 81.8(18) . . ? N1B C16A C22B 153.8(12) . . ? C17B C16A C24B 131.7(14) . . ? C16B C16A C24B 99.6(15) . . ? O2A C16A C24B 129.2(14) . . ? N1A C16A C24B 11.4(9) . . ? C17A C16A C24B 106.3(12) . . ? C18B C16A C24B 79.4(10) . . ? N1B C16A C24B 47.7(8) . . ? C22B C16A C24B 118.6(13) . . ? C18B C17A C17B 88(3) . . ? C18B C17A C22B 139(2) . . ? C17B C17A C22B 87(2) . . ? C18B C17A C18A 28.9(18) . . ? C17B C17A C18A 107.8(16) . . ? C22B C17A C18A 156.3(18) . . ? C18B C17A C16A 81(2) . . ? C17B C17A C16A 38.2(10) . . ? C22B C17A C16A 70.4(15) . . ? C18A C17A C16A 109.2(12) . . ? C18B C17A C19B 81(3) . . ? C17B C17A C19B 164.5(18) . . ? C22B C17A C19B 109(2) . . ? C18A C17A C19B 58.3(12) . . ? C16A C17A C19B 148.0(15) . . ? C18B C17A C24A 118(3) . 5_655 ? C17B C17A C24A 135.1(15) . 5_655 ? C22B C17A C24A 49.1(14) . 5_655 ? C18A C17A C24A 112.1(15) . 5_655 ? C16A C17A C24A 107.2(10) . 5_655 ? C19B C17A C24A 60.3(12) . 5_655 ? C18B C18A C19A 145(3) . . ? C18B C18A C17A 32(2) . . ? C19A C18A C17A 122.1(12) . . ? C18B C18A C23B 66(2) . . ? C19A C18A C23B 142.0(15) . . ? C17A C18A C23B 95.0(13) . . ? C18B C18A C19B 89(3) . . ? C19A C18A C19B 93.7(13) . . ? C17A C18A C19B 63.9(11) . . ? C23B C18A C19B 111.8(14) . . ? C18B C18A C23A 95(2) . . ? C19A C18A C23A 117.9(13) . . ? C17A C18A C23A 119.5(11) . . ? C23B C18A C23A 29.6(8) . . ? C19B C18A C23A 106.1(13) . . ? C18B C18A C20B 130(3) . . ? C19A C18A C20B 73.7(11) . . ? C17A C18A C20B 112.5(12) . . ? C23B C18A C20B 101.6(14) . . ? C19B C18A C20B 49.2(10) . . ? C23A C18A C20B 76.8(10) . . ? C18B C18A C17B 25(2) . . ? C19A C18A C17B 120.3(12) . . ? C17A C18A C17B 28.7(8) . . ? C23B C18A C17B 87.5(12) . . ? C19B C18A C17B 92.4(11) . . ? C23A C18A C17B 117.0(9) . . ? C20B C18A C17B 141.3(10) . . ? C18A C19A C20A 116.5(11) . . ? C18A C19A C20B 68.3(10) . . ? C20A C19A C20B 76.8(9) . . ? C18A C19A C18B 13.7(11) . . ? C20A C19A C18B 129.2(8) . . ? C20B C19A C18B 78.8(11) . . ? C18A C19A C19B 47.9(9) . . ? C20A C19A C19B 119.8(10) . . ? C20B C19A C19B 43.0(7) . . ? C18B C19A C19B 50.0(11) . . ? C19A C20A C21A 122.3(10) . . ? C22A C21A C20A 118.7(12) . . ? C23A C22A C21A 119.9(15) . . ? C23A C22A C21B 73.5(13) . . ? C21A C22A C21B 90.3(12) . . ? C23A C22A C23B 11.3(14) . . ? C21A C22A C23B 122.8(11) . . ? C21B C22A C23B 84.6(11) . . ? C23B C23A C22A 153(4) . . ? C23B C23A C22B 92(3) . 5_655 ? C22A C23A C22B 102(2) . 5_655 ? C23B C23A C24A 43(2) . . ? C22A C23A C24A 138(2) . . ? C22B C23A C24A 51.0(13) 5_655 . ? C23B C23A C18A 66(2) . . ? C22A C23A C18A 124.6(14) . . ? C22B C23A C18A 115.5(19) 5_655 . ? C24A C23A C18A 97.3(17) . . ? C23B C23A C21B 140(3) . . ? C22A C23A C21B 66.1(11) . . ? C22B C23A C21B 60.7(15) 5_655 . ? C24A C23A C21B 109.8(14) . . ? C18A C23A C21B 98.0(14) . . ? C23B C23A C18B 41(2) . . ? C22A C23A C18B 149.6(17) . . ? C22B C23A C18B 103(2) 5_655 . ? C24A C23A C18B 72.2(15) . . ? C18A C23A C18B 25.9(8) . . ? C21B C23A C18B 112.2(18) . . ? C24B C24A C23B 94.2(19) . . ? C24B C24A C22B 160.9(19) . 5_655 ? C23B C24A C22B 92.5(18) . 5_655 ? C24B C24A N1A 29.0(11) . . ? C23B C24A N1A 91.4(18) . . ? C22B C24A N1A 168.4(16) 5_655 . ? C24B C24A C23A 117.6(14) . . ? C23B C24A C23A 29.7(12) . . ? C22B C24A C23A 64.4(13) 5_655 . ? N1A C24A C23A 120.9(13) . . ? C24B C24A C19B 72.5(14) . 5_655 ? C23B C24A C19B 147.3(18) . 5_655 ? C22B C24A C19B 109.9(17) 5_655 5_655 ? N1A C24A C19B 62.3(11) . 5_655 ? C23A C24A C19B 165.6(17) . 5_655 ? C24B C24A C17A 127.2(14) . 5_655 ? C23B C24A C17A 134.8(17) . 5_655 ? C22B C24A C17A 54.9(14) 5_655 5_655 ? N1A C24A C17A 115.6(12) . 5_655 ? C23A C24A C17A 115.2(12) . 5_655 ? C19B C24A C17A 55.7(12) 5_655 5_655 ? C24B C24A C18B 93.3(13) . . ? C23B C24A C18B 39.7(14) . . ? C22B C24A C18B 103.2(14) 5_655 . ? N1A C24A C18B 73.2(9) . . ? C23A C24A C18B 61.2(13) . . ? C19B C24A C18B 109.8(12) 5_655 . ? C17A C24A C18B 111.9(12) 5_655 . ? O2A O2B C16B 39.8(7) . . ? N1A N1B C16B 96.1(13) . . ? N1A N1B C24B 27.9(10) . . ? C16B N1B C24B 118.5(13) . . ? N1A N1B C16A 53.6(10) . . ? C16B N1B C16A 42.5(9) . . ? C24B N1B C16A 78.2(10) . . ? O2A C16B C16A 77(2) . . ? O2A C16B O2B 66(2) . . ? C16A C16B O2B 143.1(18) . . ? O2A C16B N1B 124.7(17) . . ? C16A C16B N1B 83.8(15) . . ? O2B C16B N1B 120.3(15) . . ? O2A C16B C17B 77.8(19) . . ? C16A C16B C17B 40.4(10) . . ? O2B C16B C17B 122.5(11) . . ? N1B C16B C17B 116.9(16) . . ? O2A C16B N1A 108(2) . . ? C16A C16B N1A 46.1(12) . . ? O2B C16B N1A 150.6(11) . . ? N1B C16B N1A 37.7(8) . . ? C17B C16B N1A 81.2(12) . . ? C16A C17B C17A 99.9(18) . . ? C16A C17B C18B 88.9(16) . . ? C17A C17B C18B 41.7(15) . . ? C16A C17B C16B 50.0(12) . . ? C17A C17B C16B 147.8(16) . . ? C18B C17B C16B 116.3(16) . . ? C16A C17B O2A 54.5(12) . . ? C17A C17B O2A 144.1(14) . . ? C18B C17B O2A 141.5(13) . . ? C16B C17B O2A 32.4(6) . . ? C16A C17B C22B 73.1(15) . . ? C17A C17B C22B 56.6(16) . . ? C18B C17B C22B 90(2) . . ? C16B C17B C22B 113.5(14) . . ? O2A C17B C22B 89.5(14) . . ? C16A C17B C18A 103.2(13) . . ? C17A C17B C18A 43.5(12) . . ? C18B C17B C18A 14.8(13) . . ? C16B C17B C18A 123.2(10) . . ? O2A C17B C18A 153.1(9) . . ? C22B C17B C18A 98.2(14) . . ? C18A C18B C17A 119(4) . . ? C18A C18B C17B 140(3) . . ? C17A C18B C17B 49.8(15) . . ? C18A C18B C23B 81(2) . . ? C17A C18B C23B 147(4) . . ? C17B C18B C23B 131(2) . . ? C18A C18B C16A 170(4) . . ? C17A C18B C16A 66.5(18) . . ? C17B C18B C16A 35.7(7) . . ? C23B C18B C16A 98.4(17) . . ? C18A C18B C19B 62(2) . . ? C17A C18B C19B 67(3) . . ? C17B C18B C19B 116(2) . . ? C23B C18B C19B 106.9(19) . . ? C16A C18B C19B 127(2) . . ? C18A C18B C23A 59.6(17) . . ? C17A C18B C23A 149(4) . . ? C17B C18B C23A 153.0(19) . . ? C23B C18B C23A 22.7(11) . . ? C16A C18B C23A 120.8(13) . . ? C19B C18B C23A 88.6(13) . . ? C18A C18B C19A 21.1(18) . . ? C17A C18B C19A 106(2) . . ? C17B C18B C19A 119.1(17) . . ? C23B C18B C19A 99.3(17) . . ? C16A C18B C19A 152.9(18) . . ? C19B C18B C19A 65.9(11) . . ? C23A C18B C19A 79.5(10) . . ? C18A C18B C24A 105(2) . . ? C17A C18B C24A 116(3) . . ? C17B C18B C24A 113.9(15) . . ? C23B C18B C24A 31.1(12) . . ? C16A C18B C24A 78.2(11) . . ? C19B C18B C24A 101.0(17) . . ? C23A C18B C24A 46.5(8) . . ? C19A C18B C24A 125.6(11) . . ? C23A C23B C24A 107(3) . . ? C23A C23B C18B 116(3) . . ? C24A C23B C18B 109(2) . . ? C23A C23B C18A 84(3) . . ? C24A C23B C18A 132.3(19) . . ? C18B C23B C18A 33.0(9) . . ? C23A C23B C24B 137(2) . . ? C24A C23B C24B 42.1(11) . . ? C18B C23B C24B 104.2(18) . . ? C18A C23B C24B 137.1(16) . . ? C23A C23B C22B 61(2) . 5_655 ? C24A C23B C22B 48.7(15) . 5_655 ? C18B C23B C22B 116(2) . 5_655 ? C18A C23B C22B 110.3(16) . 5_655 ? C24B C23B C22B 89.4(17) . 5_655 ? C23A C23B C22A 15(2) . . ? C24A C23B C22A 111.0(17) . . ? C18B C23B C22A 125.1(17) . . ? C18A C23B C22A 92.2(13) . . ? C24B C23B C22A 130.7(10) . . ? C22B C23B C22A 69.9(14) 5_655 . ? C23A C23B N1A 158(3) . . ? C24A C23B N1A 52.0(13) . . ? C18B C23B N1A 81.1(15) . . ? C18A C23B N1A 114.0(13) . . ? C24B C23B N1A 23.1(6) . . ? C22B C23B N1A 100.1(17) 5_655 . ? C22A C23B N1A 153.8(9) . . ? N1A C24B C24A 106(3) . . ? N1A C24B N1B 46(3) . . ? C24A C24B N1B 145.9(16) . . ? N1A C24B C23B 98(2) . . ? C24A C24B C23B 43.7(13) . . ? N1B C24B C23B 111.8(12) . . ? N1A C24B C19B 73(2) . 5_655 ? C24A C24B C19B 69.8(14) . 5_655 ? N1B C24B C19B 109.8(14) . 5_655 ? C23B C24B C19B 107.9(16) . 5_655 ? N1A C24B C16A 21.1(17) . . ? C24A C24B C16A 93.1(15) . . ? N1B C24B C16A 54.1(8) . . ? C23B C24B C16A 77.6(9) . . ? C19B C24B C16A 82.8(10) 5_655 . ? C20B C19B C18A 79.6(16) . . ? C20B C19B C17A 137(2) . . ? C18A C19B C17A 57.8(12) . . ? C20B C19B N1A 90.6(17) . 5_655 ? C18A C19B N1A 138.3(14) . 5_655 ? C17A C19B N1A 114.7(14) . 5_655 ? C20B C19B C24A 140.2(19) . 5_655 ? C18A C19B C24A 114.8(15) . 5_655 ? C17A C19B C24A 63.9(10) . 5_655 ? N1A C19B C24A 53.2(10) 5_655 5_655 ? C20B C19B C24B 114(2) . 5_655 ? C18A C19B C24B 149.5(15) . 5_655 ? C17A C19B C24B 101.1(14) . 5_655 ? N1A C19B C24B 25.8(6) 5_655 5_655 ? C24A C19B C24B 37.8(9) 5_655 5_655 ? C20B C19B C18B 104.9(18) . . ? C18A C19B C18B 29.1(10) . . ? C17A C19B C18B 31.8(8) . . ? N1A C19B C18B 123.1(17) 5_655 . ? C24A C19B C18B 86.0(15) 5_655 . ? C24B C19B C18B 122.7(18) 5_655 . ? C20B C19B C19A 66.3(13) . . ? C18A C19B C19A 38.4(8) . . ? C17A C19B C19A 82.9(14) . . ? N1A C19B C19A 156.7(13) 5_655 . ? C24A C19B C19A 146.8(16) 5_655 . ? C24B C19B C19A 171.8(13) 5_655 . ? C18B C19B C19A 64.1(15) . . ? C21B C20B C19B 116.0(17) . . ? C21B C20B C18A 93.8(15) . . ? C19B C20B C18A 51.2(13) . . ? C21B C20B C19A 116.2(16) . . ? C19B C20B C19A 70.7(15) . . ? C18A C20B C19A 38.0(6) . . ? C20B C21B C22A 109.1(19) . . ? C20B C21B C22B 115.5(17) . 5_655 ? C22A C21B C22B 82.4(18) . 5_655 ? C20B C21B C23A 91.0(18) . . ? C22A C21B C23A 40.4(12) . . ? C22B C21B C23A 57.3(15) 5_655 . ? C24A C22B C17A 76(2) 5_655 . ? C24A C22B C23A 64.7(14) 5_655 5_655 ? C17A C22B C23A 134(3) . 5_655 ? C24A C22B C21B 124.2(19) 5_655 5_655 ? C17A C22B C21B 137(2) . 5_655 ? C23A C22B C21B 62.0(14) 5_655 5_655 ? C24A C22B C16A 117.3(18) 5_655 . ? C17A C22B C16A 57.2(11) . . ? C23A C22B C16A 122.8(14) 5_655 . ? C21B C22B C16A 80.5(17) 5_655 . ? C24A C22B C17B 112(2) 5_655 . ? C17A C22B C17B 36.8(9) . . ? C23A C22B C17B 153.3(15) 5_655 . ? C21B C22B C17B 108(2) 5_655 . ? C16A C22B C17B 32.4(7) . . ? C24A C22B C23B 38.8(10) 5_655 5_655 ? C17A C22B C23B 109(2) . 5_655 ? C23A C22B C23B 27.0(8) 5_655 5_655 ? C21B C22B C23B 85.7(15) 5_655 5_655 ? C16A C22B C23B 120.4(11) . 5_655 ? C17B C22B C23B 138.4(18) . 5_655 ? 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 C1 C1 C2 C3 1(19) 3_655 . . . ? C1 C2 C3 O1 21(8) . . . . ? C1 C2 C3 C10 143(8) . . . . ? C1 C2 C3 C4 -97(8) . . . . ? O1 C3 C4 C5 -145.2(4) . . . . ? C2 C3 C4 C5 -26.6(5) . . . . ? C10 C3 C4 C5 95.0(4) . . . . ? O1 C3 C4 C9 36.9(5) . . . . ? C2 C3 C4 C9 155.5(4) . . . . ? C10 C3 C4 C9 -82.9(4) . . . . ? C9 C4 C5 C6 0.1(7) . . . . ? C3 C4 C5 C6 -177.9(4) . . . . ? C4 C5 C6 C7 -0.1(7) . . . . ? C5 C6 C7 C8 0.1(8) . . . . ? C6 C7 C8 C9 -0.1(8) . . . . ? C7 C8 C9 C4 0.0(7) . . . . ? C5 C4 C9 C8 0.0(6) . . . . ? C3 C4 C9 C8 178.0(4) . . . . ? O1 C3 C10 C15 -15.5(5) . . . . ? C2 C3 C10 C15 -136.7(4) . . . . ? C4 C3 C10 C15 101.9(4) . . . . ? O1 C3 C10 C11 168.8(3) . . . . ? C2 C3 C10 C11 47.7(5) . . . . ? C4 C3 C10 C11 -73.8(4) . . . . ? C15 C10 C11 C12 0.9(6) . . . . ? C3 C10 C11 C12 176.7(4) . . . . ? C10 C11 C12 C13 -0.8(7) . . . . ? C11 C12 C13 C14 0.2(8) . . . . ? C12 C13 C14 C15 0.2(9) . . . . ? C13 C14 C15 C10 0.0(8) . . . . ? C11 C10 C15 C14 -0.5(7) . . . . ? C3 C10 C15 C14 -176.3(4) . . . . ? C16B O2A C16A C17B 92.7(19) . . . . ? O2B O2A C16A C17B 86.6(17) . . . . ? O2B O2A C16A C16B -6.0(13) . . . . ? C17B O2A C16A C16B -92.7(19) . . . . ? C16B O2A C16A N1A -62(2) . . . . ? O2B O2A C16A N1A -68(2) . . . . ? C17B O2A C16A N1A -154(3) . . . . ? C16B O2A C16A C17A 115(2) . . . . ? O2B O2A C16A C17A 108.5(18) . . . . ? C17B O2A C16A C17A 21.9(12) . . . . ? C16B O2A C16A C18B 76(3) . . . . ? O2B O2A C16A C18B 70(3) . . . . ? C17B O2A C16A C18B -17(3) . . . . ? C16B O2A C16A N1B -40.0(13) . . . . ? O2B O2A C16A N1B -46.0(14) . . . . ? C17B O2A C16A N1B -132.6(15) . . . . ? C16B O2A C16A C22B 166.3(17) . . . . ? O2B O2A C16A C22B 160.2(13) . . . . ? C17B O2A C16A C22B 73.6(13) . . . . ? C16B O2A C16A C24B -52.3(19) . . . . ? O2B O2A C16A C24B -58(2) . . . . ? C17B O2A C16A C24B -145(2) . . . . ? C24B N1A C16A C17B 7(9) . . . . ? N1B N1A C16A C17B -101(3) . . . . ? C24A N1A C16A C17B 45(4) . . . . ? C19B N1A C16A C17B 115(3) 5_655 . . . ? C23B N1A C16A C17B 16(4) . . . . ? C16B N1A C16A C17B -98(4) . . . . ? C24B N1A C16A C16B 106(7) . . . . ? N1B N1A C16A C16B -3.2(15) . . . . ? C24A N1A C16A C16B 143.5(15) . . . . ? C19B N1A C16A C16B -146.6(15) 5_655 . . . ? C23B N1A C16A C16B 113.8(15) . . . . ? C24B N1A C16A O2A 141(6) . . . . ? N1B N1A C16A O2A 32(2) . . . . ? C24A N1A C16A O2A 178.9(15) . . . . ? C19B N1A C16A O2A -111(2) 5_655 . . . ? C23B N1A C16A O2A 149.3(17) . . . . ? C16B N1A C16A O2A 35.5(12) . . . . ? C24B N1A C16A C17A -35(7) . . . . ? N1B N1A C16A C17A -144.1(13) . . . . ? C24A N1A C16A C17A 3(2) . . . . ? C19B N1A C16A C17A 72.5(17) 5_655 . . . ? C23B N1A C16A C17A -27.1(16) . . . . ? C16B N1A C16A C17A -141(2) . . . . ? C24B N1A C16A C18B -14(7) . . . . ? N1B N1A C16A C18B -122.5(17) . . . . ? C24A N1A C16A C18B 24(2) . . . . ? C19B N1A C16A C18B 94.1(18) 5_655 . . . ? C23B N1A C16A C18B -5.5(17) . . . . ? C16B N1A C16A C18B -119(2) . . . . ? C24B N1A C16A N1B 109(7) . . . . ? C24A N1A C16A N1B 146.7(18) . . . . ? C19B N1A C16A N1B -143.4(17) 5_655 . . . ? C23B N1A C16A N1B 117.0(14) . . . . ? C16B N1A C16A N1B 3.2(15) . . . . ? C24B N1A C16A C22B -95(7) . . . . ? N1B N1A C16A C22B 156.5(17) . . . . ? C24A N1A C16A C22B -57(2) . . . . ? C19B N1A C16A C22B 13(2) 5_655 . . . ? C23B N1A C16A C22B -86.4(18) . . . . ? C16B N1A C16A C22B 160(2) . . . . ? N1B N1A C16A C24B -109(7) . . . . ? C24A N1A C16A C24B 38(6) . . . . ? C19B N1A C16A C24B 108(7) 5_655 . . . ? C23B N1A C16A C24B 8(6) . . . . ? C16B N1A C16A C24B -106(7) . . . . ? C17B C16A C17A C18B -99(3) . . . . ? C16B C16A C17A C18B -82(4) . . . . ? O2A C16A C17A C18B -133(3) . . . . ? N1A C16A C17A C18B 43(3) . . . . ? N1B C16A C17A C18B -1(4) . . . . ? C22B C16A C17A C18B 150(3) . . . . ? C24B C16A C17A C18B 36(3) . . . . ? C16B C16A C17A C17B 17(2) . . . . ? O2A C16A C17A C17B -34(2) . . . . ? N1A C16A C17A C17B 142(2) . . . . ? C18B C16A C17A C17B 99(3) . . . . ? N1B C16A C17A C17B 99(3) . . . . ? C22B C16A C17A C17B -111(2) . . . . ? C24B C16A C17A C17B 135.5(19) . . . . ? C17B C16A C17A C22B 111(2) . . . . ? C16B C16A C17A C22B 128(2) . . . . ? O2A C16A C17A C22B 76.7(19) . . . . ? N1A C16A C17A C22B -107.1(18) . . . . ? C18B C16A C17A C22B -150(3) . . . . ? N1B C16A C17A C22B -151(2) . . . . ? C24B C16A C17A C22B -113.9(14) . . . . ? C17B C16A C17A C18A -94.6(18) . . . . ? C16B C16A C17A C18A -77(2) . . . . ? O2A C16A C17A C18A -128.5(18) . . . . ? N1A C16A C17A C18A 47.8(19) . . . . ? C18B C16A C17A C18A 5(2) . . . . ? N1B C16A C17A C18A 4(3) . . . . ? C22B C16A C17A C18A 154.8(19) . . . . ? C24B C16A C17A C18A 41.0(15) . . . . ? C17B C16A C17A C19B -155(3) . . . . ? C16B C16A C17A C19B -138(3) . . . . ? O2A C16A C17A C19B 171(2) . . . . ? N1A C16A C17A C19B -13(3) . . . . ? C18B C16A C17A C19B -56(4) . . . . ? N1B C16A C17A C19B -56(4) . . . . ? C22B C16A C17A C19B 94(3) . . . . ? C24B C16A C17A C19B -20(3) . . . . ? C17B C16A C17A C24A 144(2) . . . 5_655 ? C16B C16A C17A C24A 161.1(19) . . . 5_655 ? O2A C16A C17A C24A 109.8(19) . . . 5_655 ? N1A C16A C17A C24A -73.9(18) . . . 5_655 ? C18B C16A C17A C24A -117(3) . . . 5_655 ? N1B C16A C17A C24A -118(2) . . . 5_655 ? C22B C16A C17A C24A 33.2(11) . . . 5_655 ? C24B C16A C17A C24A -80.7(13) . . . 5_655 ? C17B C17A C18A C18B -50(5) . . . . ? C22B C17A C18A C18B 75(7) . . . . ? C16A C17A C18A C18B -10(5) . . . . ? C19B C17A C18A C18B 137(5) . . . . ? C24A C17A C18A C18B 109(5) 5_655 . . . ? C18B C17A C18A C19A 146(6) . . . . ? C17B C17A C18A C19A 95.3(18) . . . . ? C22B C17A C18A C19A -139(4) . . . . ? C16A C17A C18A C19A 135.7(15) . . . . ? C19B C17A C18A C19A -77.1(17) . . . . ? C24A C17A C18A C19A -105.7(16) 5_655 . . . ? C18B C17A C18A C23B -25(5) . . . . ? C17B C17A C18A C23B -75.6(17) . . . . ? C22B C17A C18A C23B 50(5) . . . . ? C16A C17A C18A C23B -35.2(17) . . . . ? C19B C17A C18A C23B 111.9(15) . . . . ? C24A C17A C18A C23B 83.4(15) 5_655 . . . ? C18B C17A C18A C19B -137(5) . . . . ? C17B C17A C18A C19B 172.5(18) . . . . ? C22B C17A C18A C19B -62(4) . . . . ? C16A C17A C18A C19B -147.2(16) . . . . ? C24A C17A C18A C19B -28.5(12) 5_655 . . . ? C18B C17A C18A C23A -43(5) . . . . ? C17B C17A C18A C23A -93.1(19) . . . . ? C22B C17A C18A C23A 32(5) . . . . ? C16A C17A C18A C23A -52.7(19) . . . . ? C19B C17A C18A C23A 94.4(16) . . . . ? C24A C17A C18A C23A 65.9(17) 5_655 . . . ? C18B C17A C18A C20B -130(5) . . . . ? C17B C17A C18A C20B 179.7(14) . . . . ? C22B C17A C18A C20B -55(5) . . . . ? C16A C17A C18A C20B -140.0(13) . . . . ? C19B C17A C18A C20B 7.2(12) . . . . ? C24A C17A C18A C20B -21.3(14) 5_655 . . . ? C18B C17A C18A C17B 50(5) . . . . ? C22B C17A C18A C17B 125(5) . . . . ? C16A C17A C18A C17B 40.4(11) . . . . ? C19B C17A C18A C17B -172.5(18) . . . . ? C24A C17A C18A C17B 159.0(19) 5_655 . . . ? C18B C18A C19A C20A -160(6) . . . . ? C17A C18A C19A C20A 168.6(14) . . . . ? C23B C18A C19A C20A -26(3) . . . . ? C19B C18A C19A C20A 107.3(13) . . . . ? C23A C18A C19A C20A -3.1(18) . . . . ? C20B C18A C19A C20A 61.9(11) . . . . ? C17B C18A C19A C20A -157.8(9) . . . . ? C18B C18A C19A C20B 138(6) . . . . ? C17A C18A C19A C20B 106.7(17) . . . . ? C23B C18A C19A C20B -88(3) . . . . ? C19B C18A C19A C20B 45.5(11) . . . . ? C23A C18A C19A C20B -64.9(14) . . . . ? C17B C18A C19A C20B 140.4(13) . . . . ? C17A C18A C19A C18B -32(5) . . . . ? C23B C18A C19A C18B 134(7) . . . . ? C19B C18A C19A C18B -93(6) . . . . ? C23A C18A C19A C18B 157(7) . . . . ? C20B C18A C19A C18B -138(6) . . . . ? C17B C18A C19A C18B 2(5) . . . . ? C18B C18A C19A C19B 93(6) . . . . ? C17A C18A C19A C19B 61.3(15) . . . . ? C23B C18A C19A C19B -133(3) . . . . ? C23A C18A C19A C19B -110.4(18) . . . . ? C20B C18A C19A C19B -45.5(11) . . . . ? C17B C18A C19A C19B 94.9(14) . . . . ? C18A C19A C20A C21A 2.1(16) . . . . ? C20B C19A C20A C21A 59.5(10) . . . . ? C18B C19A C20A C21A -3.9(19) . . . . ? C19B C19A C20A C21A 56.9(13) . . . . ? C19A C20A C21A C22A 1.1(15) . . . . ? C20A C21A C22A C23A -3(2) . . . . ? C20A C21A C22A C21B -74.5(13) . . . . ? C20A C21A C22A C23B 9.4(17) . . . . ? C21A C22A C23A C23B 108(7) . . . . ? C21B C22A C23A C23B -171(7) . . . . ? C21A C22A C23A C22B -130.6(15) . . . 5_655 ? C21B C22A C23A C22B -50.0(15) . . . 5_655 ? C23B C22A C23A C22B 121(7) . . . 5_655 ? C21A C22A C23A C24A -174.2(17) . . . . ? C21B C22A C23A C24A -94(3) . . . . ? C23B C22A C23A C24A 78(7) . . . . ? C21A C22A C23A C18A 2(3) . . . . ? C21B C22A C23A C18A 83.1(18) . . . . ? C23B C22A C23A C18A -106(7) . . . . ? C21A C22A C23A C21B -80.6(15) . . . . ? C23B C22A C23A C21B 171(7) . . . . ? C21A C22A C23A C18B 13(5) . . . . ? C21B C22A C23A C18B 94(4) . . . . ? C23B C22A C23A C18B -95(7) . . . . ? C18B C18A C23A C23B 16(4) . . . . ? C19A C18A C23A C23B -151(3) . . . . ? C17A C18A C23A C23B 37(3) . . . . ? C19B C18A C23A C23B 106(3) . . . . ? C20B C18A C23A C23B 146(3) . . . . ? C17B C18A C23A C23B 5(3) . . . . ? C18B C18A C23A C22A 168(3) . . . . ? C19A C18A C23A C22A 1(3) . . . . ? C17A C18A C23A C22A -171.0(19) . . . . ? C23B C18A C23A C22A 152(4) . . . . ? C19B C18A C23A C22A -102(2) . . . . ? C20B C18A C23A C22A -62.3(19) . . . . ? C17B C18A C23A C22A 156.5(16) . . . . ? C18B C18A C23A C22B -64(4) . . . 5_655 ? C19A C18A C23A C22B 129(2) . . . 5_655 ? C17A C18A C23A C22B -43(2) . . . 5_655 ? C23B C18A C23A C22B -81(3) . . . 5_655 ? C19B C18A C23A C22B 25(2) . . . 5_655 ? C20B C18A C23A C22B 65.4(18) . . . 5_655 ? C17B C18A C23A C22B -76(2) . . . 5_655 ? C18B C18A C23A C24A -14(3) . . . . ? C19A C18A C23A C24A 178.7(13) . . . . ? C17A C18A C23A C24A 6.8(18) . . . . ? C23B C18A C23A C24A -31(2) . . . . ? C19B C18A C23A C24A 75.5(14) . . . . ? C20B C18A C23A C24A 115.4(12) . . . . ? C17B C18A C23A C24A -25.8(14) . . . . ? C18B C18A C23A C21B -126(3) . . . . ? C19A C18A C23A C21B 67.4(18) . . . . ? C17A C18A C23A C21B -104.5(17) . . . . ? C23B C18A C23A C21B -142(3) . . . . ? C19B C18A C23A C21B -35.8(17) . . . . ? C20B C18A C23A C21B 4.2(12) . . . . ? C17B C18A C23A C21B -137.1(12) . . . . ? C19A C18A C23A C18B -167(4) . . . . ? C17A C18A C23A C18B 21(3) . . . . ? C23B C18A C23A C18B -16(4) . . . . ? C19B C18A C23A C18B 90(3) . . . . ? C20B C18A C23A C18B 130(3) . . . . ? C17B C18A C23A C18B -11(3) . . . . ? N1B N1A C24A C24B -42(3) . . . . ? C16A N1A C24A C24B -152(3) . . . . ? C19B N1A C24A C24B 104(3) 5_655 . . . ? C23B N1A C24A C24B -96(3) . . . . ? C16B N1A C24A C24B -119(4) . . . . ? C24B N1A C24A C23B 96(3) . . . . ? N1B N1A C24A C23B 54(3) . . . . ? C16A N1A C24A C23B -56.0(18) . . . . ? C19B N1A C24A C23B -159.7(16) 5_655 . . . ? C16B N1A C24A C23B -23(2) . . . . ? C24B N1A C24A C22B -154(9) . . . 5_655 ? N1B N1A C24A C22B 164(7) . . . 5_655 ? C16A N1A C24A C22B 54(9) . . . 5_655 ? C19B N1A C24A C22B -50(8) 5_655 . . 5_655 ? C23B N1A C24A C22B 110(9) . . . 5_655 ? C16B N1A C24A C22B 86(9) . . . 5_655 ? C24B N1A C24A C23A 92(3) . . . . ? N1B N1A C24A C23A 50(3) . . . . ? C16A N1A C24A C23A -60(2) . . . . ? C19B N1A C24A C23A -164(2) 5_655 . . . ? C23B N1A C24A C23A -4.2(16) . . . . ? C16B N1A C24A C23A -27(3) . . . . ? C24B N1A C24A C19B -104(3) . . . 5_655 ? N1B N1A C24A C19B -146(2) . . . 5_655 ? C16A N1A C24A C19B 103.7(17) . . . 5_655 ? C23B N1A C24A C19B 159.7(16) . . . 5_655 ? C16B N1A C24A C19B 137(2) . . . 5_655 ? C24B N1A C24A C17A -121(3) . . . 5_655 ? N1B N1A C24A C17A -163.2(17) . . . 5_655 ? C16A N1A C24A C17A 86.5(17) . . . 5_655 ? C19B N1A C24A C17A -17.1(12) 5_655 . . 5_655 ? C23B N1A C24A C17A 143(2) . . . 5_655 ? C16B N1A C24A C17A 119(2) . . . 5_655 ? C24B N1A C24A C18B 132(3) . . . . ? N1B N1A C24A C18B 90(2) . . . . ? C16A N1A C24A C18B -20.2(16) . . . . ? C19B N1A C24A C18B -123.9(14) 5_655 . . . ? C23B N1A C24A C18B 35.8(15) . . . . ? C16B N1A C24A C18B 13(2) . . . . ? C23B C23A C24A C24B 42(3) . . . . ? C22A C23A C24A C24B -99(3) . . . . ? C22B C23A C24A C24B -159(2) 5_655 . . . ? C18A C23A C24A C24B 84(2) . . . . ? C21B C23A C24A C24B -174.5(17) . . . . ? C18B C23A C24A C24B 78(2) . . . . ? C22A C23A C24A C23B -140(5) . . . . ? C22B C23A C24A C23B 160(3) 5_655 . . . ? C18A C23A C24A C23B 43(2) . . . . ? C21B C23A C24A C23B 144(4) . . . . ? C18B C23A C24A C23B 36(3) . . . . ? C23B C23A C24A C22B -160(3) . . . 5_655 ? C22A C23A C24A C22B 60(3) . . . 5_655 ? C18A C23A C24A C22B -117.1(15) . . . 5_655 ? C21B C23A C24A C22B -15.8(16) . . . 5_655 ? C18B C23A C24A C22B -123.6(16) . . . 5_655 ? C23B C23A C24A N1A 9(3) . . . . ? C22A C23A C24A N1A -132(2) . . . . ? C22B C23A C24A N1A 168.2(18) 5_655 . . . ? C18A C23A C24A N1A 51.2(19) . . . . ? C21B C23A C24A N1A 152.4(15) . . . . ? C18B C23A C24A N1A 44.6(18) . . . . ? C23B C23A C24A C19B -90(6) . . . 5_655 ? C22A C23A C24A C19B 130(6) . . . 5_655 ? C22B C23A C24A C19B 69(6) 5_655 . . 5_655 ? C18A C23A C24A C19B -48(6) . . . 5_655 ? C21B C23A C24A C19B 54(7) . . . 5_655 ? C18B C23A C24A C19B -54(6) . . . 5_655 ? C23B C23A C24A C17A -138(3) . . . 5_655 ? C22A C23A C24A C17A 81(3) . . . 5_655 ? C22B C23A C24A C17A 21.3(15) 5_655 . . 5_655 ? C18A C23A C24A C17A -95.7(14) . . . 5_655 ? C21B C23A C24A C17A 6(2) . . . 5_655 ? C18B C23A C24A C17A -102.3(15) . . . 5_655 ? C23B C23A C24A C18B -36(3) . . . . ? C22A C23A C24A C18B -176(3) . . . . ? C22B C23A C24A C18B 123.6(16) 5_655 . . . ? C18A C23A C24A C18B 6.5(14) . . . . ? C21B C23A C24A C18B 108(2) . . . . ? C16A O2A O2B C16B 5.5(12) . . . . ? C17B O2A O2B C16B 52.7(13) . . . . ? C24B N1A N1B C16B -145(2) . . . . ? C16A N1A N1B C16B 2.7(12) . . . . ? C24A N1A N1B C16B -116(2) . . . . ? C19B N1A N1B C16B 119(2) 5_655 . . . ? C23B N1A N1B C16B -83.3(12) . . . . ? C16A N1A N1B C24B 148(3) . . . . ? C24A N1A N1B C24B 29.3(19) . . . . ? C19B N1A N1B C24B -96(3) 5_655 . . . ? C23B N1A N1B C24B 62(2) . . . . ? C16B N1A N1B C24B 145(2) . . . . ? C24B N1A N1B C16A -148(3) . . . . ? C24A N1A N1B C16A -119(2) . . . . ? C19B N1A N1B C16A 116(3) 5_655 . . . ? C23B N1A N1B C16A -86.0(11) . . . . ? C16B N1A N1B C16A -2.7(12) . . . . ? C17B C16A N1B N1A 128(2) . . . . ? C16B C16A N1B N1A 176.0(18) . . . . ? O2A C16A N1B N1A -152.4(15) . . . . ? C17A C16A N1B N1A 66(2) . . . . ? C18B C16A N1B N1A 65.3(17) . . . . ? C22B C16A N1B N1A -53(3) . . . . ? C24B C16A N1B N1A 14.6(13) . . . . ? C17B C16A N1B C16B -48(2) . . . . ? O2A C16A N1B C16B 31.5(10) . . . . ? N1A C16A N1B C16B -176.0(18) . . . . ? C17A C16A N1B C16B -110(3) . . . . ? C18B C16A N1B C16B -111(2) . . . . ? C22B C16A N1B C16B 131(4) . . . . ? C24B C16A N1B C16B -161.4(14) . . . . ? C17B C16A N1B C24B 113(2) . . . . ? C16B C16A N1B C24B 161.4(14) . . . . ? O2A C16A N1B C24B -167.0(11) . . . . ? N1A C16A N1B C24B -14.6(13) . . . . ? C17A C16A N1B C24B 51(2) . . . . ? C18B C16A N1B C24B 50.7(16) . . . . ? C22B C16A N1B C24B -67(3) . . . . ? O2B O2A C16B C16A 175.6(9) . . . . ? C17B O2A C16B C16A 41.4(8) . . . . ? C16A O2A C16B O2B -175.6(9) . . . . ? C17B O2A C16B O2B -134.3(7) . . . . ? O2B O2A C16B N1B -111(3) . . . . ? C16A O2A C16B N1B 73(3) . . . . ? C17B O2A C16B N1B 114(3) . . . . ? O2B O2A C16B C17B 134.3(7) . . . . ? C16A O2A C16B C17B -41.4(8) . . . . ? O2B O2A C16B N1A -149.2(13) . . . . ? C16A O2A C16B N1A 35.2(12) . . . . ? C17B O2A C16B N1A 76.5(14) . . . . ? C17B C16A C16B O2A -86.1(15) . . . . ? N1A C16A C16B O2A 130.4(14) . . . . ? C17A C16A C16B O2A -98(2) . . . . ? C18B C16A C16B O2A -135.3(16) . . . . ? N1B C16A C16B O2A 127.7(16) . . . . ? C22B C16A C16B O2A -21(3) . . . . ? C24B C16A C16B O2A 141.5(13) . . . . ? C17B C16A C16B O2B -79(2) . . . . ? O2A C16A C16B O2B 6.7(15) . . . . ? N1A C16A C16B O2B 137(2) . . . . ? C17A C16A C16B O2B -91(3) . . . . ? C18B C16A C16B O2B -129(2) . . . . ? N1B C16A C16B O2B 134(2) . . . . ? C22B C16A C16B O2B -15(4) . . . . ? C24B C16A C16B O2B 148.2(19) . . . . ? C17B C16A C16B N1B 146.2(12) . . . . ? O2A C16A C16B N1B -127.7(16) . . . . ? N1A C16A C16B N1B 2.7(12) . . . . ? C17A C16A C16B N1B 134.7(17) . . . . ? C18B C16A C16B N1B 97.0(13) . . . . ? C22B C16A C16B N1B -149(2) . . . . ? C24B C16A C16B N1B 13.8(11) . . . . ? O2A C16A C16B C17B 86.1(15) . . . . ? N1A C16A C16B C17B -143.5(17) . . . . ? C17A C16A C16B C17B -11.5(16) . . . . ? C18B C16A C16B C17B -49.2(13) . . . . ? N1B C16A C16B C17B -146.2(12) . . . . ? C22B C16A C16B C17B 65(2) . . . . ? C24B C16A C16B C17B -132.4(15) . . . . ? C17B C16A C16B N1A 143.5(17) . . . . ? O2A C16A C16B N1A -130.4(14) . . . . ? C17A C16A C16B N1A 132(2) . . . . ? C18B C16A C16B N1A 94.2(16) . . . . ? N1B C16A C16B N1A -2.7(12) . . . . ? C22B C16A C16B N1A -152(3) . . . . ? C24B C16A C16B N1A 11.1(9) . . . . ? O2A O2B C16B C16A -7.1(16) . . . . ? O2A O2B C16B N1B 117.5(19) . . . . ? O2A O2B C16B C17B -56.2(14) . . . . ? O2A O2B C16B N1A 84(3) . . . . ? N1A N1B C16B O2A -73(3) . . . . ? C24B N1B C16B O2A -91(3) . . . . ? C16A N1B C16B O2A -70(3) . . . . ? N1A N1B C16B C16A -3.2(15) . . . . ? C24B N1B C16B C16A -20.8(16) . . . . ? N1A N1B C16B O2B -153.4(15) . . . . ? C24B N1B C16B O2B -171.0(12) . . . . ? C16A N1B C16B O2B -150(2) . . . . ? N1A N1B C16B C17B 20.6(15) . . . . ? C24B N1B C16B C17B 3.1(17) . . . . ? C16A N1B C16B C17B 23.8(10) . . . . ? C24B N1B C16B N1A -17.6(12) . . . . ? C16A N1B C16B N1A 3.2(15) . . . . ? C24B N1A C16B O2A -179(5) . . . . ? N1B N1A C16B O2A 124(2) . . . . ? C16A N1A C16B O2A -51.2(18) . . . . ? C24A N1A C16B O2A -108(3) . . . . ? C19B N1A C16B O2A 1(3) 5_655 . . . ? C23B N1A C16B O2A -121(2) . . . . ? C24B N1A C16B C16A -127(5) . . . . ? N1B N1A C16B C16A 176(2) . . . . ? C24A N1A C16B C16A -56(2) . . . . ? C19B N1A C16B C16A 52(2) 5_655 . . . ? C23B N1A C16B C16A -70.3(16) . . . . ? C24B N1A C16B O2B 109(5) . . . . ? N1B N1A C16B O2B 52(3) . . . . ? C16A N1A C16B O2B -124(3) . . . . ? C24A N1A C16B O2B -180(2) . . . . ? C19B N1A C16B O2B -72(4) 5_655 . . . ? C23B N1A C16B O2B 166(3) . . . . ? C24B N1A C16B N1B 57(4) . . . . ? C16A N1A C16B N1B -176(2) . . . . ? C24A N1A C16B N1B 128(3) . . . . ? C19B N1A C16B N1B -124(2) 5_655 . . . ? C23B N1A C16B N1B 114.1(15) . . . . ? C24B N1A C16B C17B -104(4) . . . . ? N1B N1A C16B C17B -161.5(14) . . . . ? C16A N1A C16B C17B 23.0(12) . . . . ? C24A N1A C16B C17B -33(2) . . . . ? C19B N1A C16B C17B 75(2) 5_655 . . . ? C23B N1A C16B C17B -47.3(12) . . . . ? C16B C16A C17B C17A -166.8(17) . . . . ? O2A C16A C17B C17A 152.2(17) . . . . ? N1A C16A C17B C17A -66(4) . . . . ? C18B C16A C17B C17A -40.4(17) . . . . ? N1B C16A C17B C17A -130(2) . . . . ? C22B C16A C17B C17A 50.4(18) . . . . ? C24B C16A C17B C17A -64(3) . . . . ? C16B C16A C17B C18B -126(2) . . . . ? O2A C16A C17B C18B -167(2) . . . . ? N1A C16A C17B C18B -26(4) . . . . ? C17A C16A C17B C18B 40.4(17) . . . . ? N1B C16A C17B C18B -90(2) . . . . ? C22B C16A C17B C18B 91(2) . . . . ? C24B C16A C17B C18B -24(3) . . . . ? O2A C16A C17B C16B -40.9(9) . . . . ? N1A C16A C17B C16B 101(4) . . . . ? C17A C16A C17B C16B 166.8(17) . . . . ? C18B C16A C17B C16B 126(2) . . . . ? N1B C16A C17B C16B 36.9(16) . . . . ? C22B C16A C17B C16B -142.8(17) . . . . ? C24B C16A C17B C16B 102(3) . . . . ? C16B C16A C17B O2A 40.9(9) . . . . ? N1A C16A C17B O2A 142(4) . . . . ? C17A C16A C17B O2A -152.2(17) . . . . ? C18B C16A C17B O2A 167(2) . . . . ? N1B C16A C17B O2A 78(2) . . . . ? C22B C16A C17B O2A -101.9(16) . . . . ? C24B C16A C17B O2A 143(3) . . . . ? C16B C16A C17B C22B 142.8(17) . . . . ? O2A C16A C17B C22B 101.9(16) . . . . ? N1A C16A C17B C22B -117(4) . . . . ? C17A C16A C17B C22B -50.4(18) . . . . ? C18B C16A C17B C22B -91(2) . . . . ? N1B C16A C17B C22B 180(2) . . . . ? C24B C16A C17B C22B -115(2) . . . . ? C16B C16A C17B C18A -122.5(13) . . . . ? O2A C16A C17B C18A -163.4(11) . . . . ? N1A C16A C17B C18A -22(4) . . . . ? C17A C16A C17B C18A 44.4(12) . . . . ? C18B C16A C17B C18A 4.0(17) . . . . ? N1B C16A C17B C18A -85.5(19) . . . . ? C22B C16A C17B C18A 94.7(14) . . . . ? C24B C16A C17B C18A -20(3) . . . . ? C18B C17A C17B C16A 77(2) . . . . ? C22B C17A C17B C16A -62.1(15) . . . . ? C18A C17A C17B C16A 98.7(15) . . . . ? C19B C17A C17B C16A 123(7) . . . . ? C24A C17A C17B C16A -53(3) 5_655 . . . ? C22B C17A C17B C18B -139(2) . . . . ? C18A C17A C17B C18B 21.8(19) . . . . ? C16A C17A C17B C18B -77(2) . . . . ? C19B C17A C17B C18B 47(7) . . . . ? C24A C17A C17B C18B -130(3) 5_655 . . . ? C18B C17A C17B C16B 58(4) . . . . ? C22B C17A C17B C16B -81(3) . . . . ? C18A C17A C17B C16B 80(3) . . . . ? C16A C17A C17B C16B -19(2) . . . . ? C19B C17A C17B C16B 104(7) . . . . ? C24A C17A C17B C16B -72(4) 5_655 . . . ? C18B C17A C17B O2A 117(3) . . . . ? C22B C17A C17B O2A -22(3) . . . . ? C18A C17A C17B O2A 139(2) . . . . ? C16A C17A C17B O2A 40(2) . . . . ? C19B C17A C17B O2A 164(5) . . . . ? C24A C17A C17B O2A -13(4) 5_655 . . . ? C18B C17A C17B C22B 139(2) . . . . ? C18A C17A C17B C22B 160.8(15) . . . . ? C16A C17A C17B C22B 62.1(15) . . . . ? C19B C17A C17B C22B -174(8) . . . . ? C24A C17A C17B C22B 8.9(17) 5_655 . . . ? C18B C17A C17B C18A -21.8(19) . . . . ? C22B C17A C17B C18A -160.8(15) . . . . ? C16A C17A C17B C18A -98.7(15) . . . . ? C19B C17A C17B C18A 25(6) . . . . ? C24A C17A C17B C18A -152(3) 5_655 . . . ? O2A C16B C17B C16A 84.6(18) . . . . ? O2B C16B C17B C16A 136(2) . . . . ? N1B C16B C17B C16A -38.3(15) . . . . ? N1A C16B C17B C16A -25.7(13) . . . . ? O2A C16B C17B C17A 109(3) . . . . ? C16A C16B C17B C17A 25(3) . . . . ? O2B C16B C17B C17A 160(3) . . . . ? N1B C16B C17B C17A -13(4) . . . . ? N1A C16B C17B C17A -1(3) . . . . ? O2A C16B C17B C18B 148(2) . . . . ? C16A C16B C17B C18B 64(2) . . . . ? O2B C16B C17B C18B -161(2) . . . . ? N1B C16B C17B C18B 25(2) . . . . ? N1A C16B C17B C18B 38(2) . . . . ? C16A C16B C17B O2A -84.6(18) . . . . ? O2B C16B C17B O2A 51.0(14) . . . . ? N1B C16B C17B O2A -123(2) . . . . ? N1A C16B C17B O2A -110.3(18) . . . . ? O2A C16B C17B C22B 45(2) . . . . ? C16A C16B C17B C22B -39.1(18) . . . . ? O2B C16B C17B C22B 96.4(16) . . . . ? N1B C16B C17B C22B -77.4(15) . . . . ? N1A C16B C17B C22B -64.8(12) . . . . ? O2A C16B C17B C18A 163.5(15) . . . . ? C16A C16B C17B C18A 78.9(16) . . . . ? O2B C16B C17B C18A -145.5(12) . . . . ? N1B C16B C17B C18A 40.6(17) . . . . ? N1A C16B C17B C18A 53.2(12) . . . . ? C16B O2A C17B C16A -69.7(17) . . . . ? O2B O2A C17B C16A -124(2) . . . . ? C16B O2A C17B C17A -121(3) . . . . ? O2B O2A C17B C17A -176(2) . . . . ? C16A O2A C17B C17A -51(3) . . . . ? C16B O2A C17B C18B -49(4) . . . . ? O2B O2A C17B C18B -104(3) . . . . ? C16A O2A C17B C18B 21(3) . . . . ? O2B O2A C17B C16B -54.7(18) . . . . ? C16A O2A C17B C16B 69.7(17) . . . . ? C16B O2A C17B C22B -139.1(18) . . . . ? O2B O2A C17B C22B 166.2(11) . . . . ? C16A O2A C17B C22B -69.5(16) . . . . ? C16B O2A C17B C18A -32(3) . . . . ? O2B O2A C17B C18A -86(2) . . . . ? C16A O2A C17B C18A 38(2) . . . . ? C18B C18A C17B C16A -16(6) . . . . ? C19A C18A C17B C16A 167.0(17) . . . . ? C17A C18A C17B C16A -91(2) . . . . ? C23B C18A C17B C16A 14.4(18) . . . . ? C19B C18A C17B C16A -97.4(17) . . . . ? C23A C18A C17B C16A 12.1(19) . . . . ? C20B C18A C17B C16A -91(2) . . . . ? C18B C18A C17B C17A 75(6) . . . . ? C19A C18A C17B C17A -102.4(18) . . . . ? C23B C18A C17B C17A 105.0(17) . . . . ? C19B C18A C17B C17A -6.8(16) . . . . ? C23A C18A C17B C17A 102.7(18) . . . . ? C20B C18A C17B C17A 0(2) . . . . ? C19A C18A C17B C18B -177(7) . . . . ? C17A C18A C17B C18B -75(6) . . . . ? C23B C18A C17B C18B 30(6) . . . . ? C19B C18A C17B C18B -82(6) . . . . ? C23A C18A C17B C18B 28(6) . . . . ? C20B C18A C17B C18B -75(6) . . . . ? C18B C18A C17B C16B -66(6) . . . . ? C19A C18A C17B C16B 116.4(15) . . . . ? C17A C18A C17B C16B -141.2(19) . . . . ? C23B C18A C17B C16B -36.2(15) . . . . ? C19B C18A C17B C16B -148.0(14) . . . . ? C23A C18A C17B C16B -38.5(17) . . . . ? C20B C18A C17B C16B -141.7(16) . . . . ? C18B C18A C17B O2A -47(6) . . . . ? C19A C18A C17B O2A 136(2) . . . . ? C17A C18A C17B O2A -122(3) . . . . ? C23B C18A C17B O2A -17(2) . . . . ? C19B C18A C17B O2A -128(2) . . . . ? C23A C18A C17B O2A -19(3) . . . . ? C20B C18A C17B O2A -122(2) . . . . ? C18B C18A C17B C22B 59(6) . . . . ? C19A C18A C17B C22B -118.5(13) . . . . ? C17A C18A C17B C22B -16.1(13) . . . . ? C23B C18A C17B C22B 88.9(13) . . . . ? C19B C18A C17B C22B -22.9(12) . . . . ? C23A C18A C17B C22B 86.6(14) . . . . ? C20B C18A C17B C22B -16.6(18) . . . . ? C19A C18A C18B C17A -57(9) . . . . ? C23B C18A C18B C17A 152(5) . . . . ? C19B C18A C18B C17A 38(5) . . . . ? C23A C18A C18B C17A 144(4) . . . . ? C20B C18A C18B C17A 67(5) . . . . ? C17B C18A C18B C17A -61(3) . . . . ? C19A C18A C18B C17B 4(11) . . . . ? C17A C18A C18B C17B 61(3) . . . . ? C23B C18A C18B C17B -147(7) . . . . ? C19B C18A C18B C17B 99(6) . . . . ? C23A C18A C18B C17B -155(5) . . . . ? C20B C18A C18B C17B 128(5) . . . . ? C19A C18A C18B C23B 151(4) . . . . ? C17A C18A C18B C23B -152(5) . . . . ? C19B C18A C18B C23B -114.7(18) . . . . ? C23A C18A C18B C23B -9(2) . . . . ? C20B C18A C18B C23B -85(3) . . . . ? C17B C18A C18B C23B 147(7) . . . . ? C19A C18A C18B C16A 65(18) . . . . ? C17A C18A C18B C16A 121(17) . . . . ? C23B C18A C18B C16A -86(16) . . . . ? C19B C18A C18B C16A 159(15) . . . . ? C23A C18A C18B C16A -95(15) . . . . ? C20B C18A C18B C16A -172(13) . . . . ? C17B C18A C18B C16A 60(14) . . . . ? C19A C18A C18B C19B -94(5) . . . . ? C17A C18A C18B C19B -38(5) . . . . ? C23B C18A C18B C19B 114.7(18) . . . . ? C23A C18A C18B C19B 106.0(14) . . . . ? C20B C18A C18B C19B 29(2) . . . . ? C17B C18A C18B C19B -99(6) . . . . ? C19A C18A C18B C23A 159(6) . . . . ? C17A C18A C18B C23A -144(4) . . . . ? C23B C18A C18B C23A 9(2) . . . . ? C19B C18A C18B C23A -106.0(14) . . . . ? C20B C18A C18B C23A -77(2) . . . . ? C17B C18A C18B C23A 155(5) . . . . ? C17A C18A C18B C19A 57(9) . . . . ? C23B C18A C18B C19A -151(4) . . . . ? C19B C18A C18B C19A 94(5) . . . . ? C23A C18A C18B C19A -159(6) . . . . ? C20B C18A C18B C19A 124(7) . . . . ? C17B C18A C18B C19A -4(11) . . . . ? C19A C18A C18B C24A 171(4) . . . . ? C17A C18A C18B C24A -132(6) . . . . ? C23B C18A C18B C24A 19.9(14) . . . . ? C19B C18A C18B C24A -95(2) . . . . ? C23A C18A C18B C24A 11(2) . . . . ? C20B C18A C18B C24A -65(3) . . . . ? C17B C18A C18B C24A 167(7) . . . . ? C17B C17A C18B C18A 133(4) . . . . ? C22B C17A C18B C18A -144(4) . . . . ? C16A C17A C18B C18A 170(5) . . . . ? C19B C17A C18B C18A -36(4) . . . . ? C24A C17A C18B C18A -85(5) 5_655 . . . ? C22B C17A C18B C17B 83(4) . . . . ? C18A C17A C18B C17B -133(4) . . . . ? C16A C17A C18B C17B 37.6(11) . . . . ? C19B C17A C18B C17B -168.7(15) . . . . ? C24A C17A C18B C17B 142(2) 5_655 . . . ? C17B C17A C18B C23B -105(6) . . . . ? C22B C17A C18B C23B -22(10) . . . . ? C18A C17A C18B C23B 122(9) . . . . ? C16A C17A C18B C23B -68(6) . . . . ? C19B C17A C18B C23B 86(6) . . . . ? C24A C17A C18B C23B 37(7) 5_655 . . . ? C17B C17A C18B C16A -37.6(11) . . . . ? C22B C17A C18B C16A 46(4) . . . . ? C18A C17A C18B C16A -170(5) . . . . ? C19B C17A C18B C16A 153.7(14) . . . . ? C24A C17A C18B C16A 104.6(16) 5_655 . . . ? C17B C17A C18B C19B 168.7(15) . . . . ? C22B C17A C18B C19B -108(5) . . . . ? C18A C17A C18B C19B 36(4) . . . . ? C16A C17A C18B C19B -153.7(14) . . . . ? C24A C17A C18B C19B -49.1(19) 5_655 . . . ? C17B C17A C18B C23A -149(4) . . . . ? C22B C17A C18B C23A -65(7) . . . . ? C18A C17A C18B C23A 78(5) . . . . ? C16A C17A C18B C23A -111(5) . . . . ? C19B C17A C18B C23A 43(4) . . . . ? C24A C17A C18B C23A -6(6) 5_655 . . . ? C17B C17A C18B C19A 114.5(18) . . . . ? C22B C17A C18B C19A -162(4) . . . . ? C18A C17A C18B C19A -18(3) . . . . ? C16A C17A C18B C19A 152.2(19) . . . . ? C19B C17A C18B C19A -54.2(17) . . . . ? C24A C17A C18B C19A -103(2) 5_655 . . . ? C17B C17A C18B C24A -100(2) . . . . ? C22B C17A C18B C24A -17(6) . . . . ? C18A C17A C18B C24A 127(6) . . . . ? C16A C17A C18B C24A -62(2) . . . . ? C19B C17A C18B C24A 91(2) . . . . ? C24A C17A C18B C24A 42(3) 5_655 . . . ? C16A C17B C18B C18A 165(6) . . . . ? C17A C17B C18B C18A -89(6) . . . . ? C16B C17B C18B C18A 121(6) . . . . ? O2A C17B C18B C18A 148(4) . . . . ? C22B C17B C18B C18A -122(6) . . . . ? C16A C17B C18B C17A -106(2) . . . . ? C16B C17B C18B C17A -150(2) . . . . ? O2A C17B C18B C17A -123(3) . . . . ? C22B C17B C18B C17A -33(2) . . . . ? C18A C17B C18B C17A 89(6) . . . . ? C16A C17B C18B C23B 30(4) . . . . ? C17A C17B C18B C23B 137(5) . . . . ? C16B C17B C18B C23B -13(5) . . . . ? O2A C17B C18B C23B 14(6) . . . . ? C22B C17B C18B C23B 103(4) . . . . ? C18A C17B C18B C23B -134(9) . . . . ? C17A C17B C18B C16A 106(2) . . . . ? C16B C17B C18B C16A -43.4(14) . . . . ? O2A C17B C18B C16A -17(3) . . . . ? C22B C17B C18B C16A 73.1(15) . . . . ? C18A C17B C18B C16A -165(6) . . . . ? C16A C17B C18B C19B -118(2) . . . . ? C17A C17B C18B C19B -11.6(16) . . . . ? C16B C17B C18B C19B -161.4(17) . . . . ? O2A C17B C18B C19B -135(2) . . . . ? C22B C17B C18B C19B -45(2) . . . . ? C18A C17B C18B C19B 77(5) . . . . ? C16A C17B C18B C23A 37(6) . . . . ? C17A C17B C18B C23A 143(7) . . . . ? C16B C17B C18B C23A -6(7) . . . . ? O2A C17B C18B C23A 20(8) . . . . ? C22B C17B C18B C23A 110(6) . . . . ? C18A C17B C18B C23A -128(11) . . . . ? C16A C17B C18B C19A 166(2) . . . . ? C17A C17B C18B C19A -87(2) . . . . ? C16B C17B C18B C19A 122.9(16) . . . . ? O2A C17B C18B C19A 149.8(15) . . . . ? C22B C17B C18B C19A -121(2) . . . . ? C18A C17B C18B C19A 2(4) . . . . ? C16A C17B C18B C24A -1(2) . . . . ? C17A C17B C18B C24A 105(3) . . . . ? C16B C17B C18B C24A -45(3) . . . . ? O2A C17B C18B C24A -18(4) . . . . ? C22B C17B C18B C24A 72(2) . . . . ? C18A C17B C18B C24A -166(8) . . . . ? C17B C16A C18B C18A -73(15) . . . . ? C16B C16A C18B C18A -6(16) . . . . ? O2A C16A C18B C18A -52(16) . . . . ? N1A C16A C18B C18A 92(15) . . . . ? C17A C16A C18B C18A -126(16) . . . . ? N1B C16A C18B C18A 54(16) . . . . ? C22B C16A C18B C18A -149(15) . . . . ? C24B C16A C18B C18A 89(15) . . . . ? C17B C16A C18B C17A 53.1(19) . . . . ? C16B C16A C18B C17A 120(3) . . . . ? O2A C16A C18B C17A 73(4) . . . . ? N1A C16A C18B C17A -142(3) . . . . ? N1B C16A C18B C17A 180(2) . . . . ? C22B C16A C18B C17A -24(2) . . . . ? C24B C16A C18B C17A -145(3) . . . . ? C16B C16A C18B C17B 67(2) . . . . ? O2A C16A C18B C17B 20(3) . . . . ? N1A C16A C18B C17B 165(2) . . . . ? C17A C16A C18B C17B -53.1(19) . . . . ? N1B C16A C18B C17B 126(2) . . . . ? C22B C16A C18B C17B -76.7(16) . . . . ? C24B C16A C18B C17B 162(2) . . . . ? C17B C16A C18B C23B -157(3) . . . . ? C16B C16A C18B C23B -90(2) . . . . ? O2A C16A C18B C23B -137(3) . . . . ? N1A C16A C18B C23B 7(2) . . . . ? C17A C16A C18B C23B 150(4) . . . . ? N1B C16A C18B C23B -31(3) . . . . ? C22B C16A C18B C23B 126(2) . . . . ? C24B C16A C18B C23B 4.8(19) . . . . ? C17B C16A C18B C19B 84(2) . . . . ? C16B C16A C18B C19B 151(2) . . . . ? O2A C16A C18B C19B 104(4) . . . . ? N1A C16A C18B C19B -111(2) . . . . ? C17A C16A C18B C19B 31(2) . . . . ? N1B C16A C18B C19B -149.6(17) . . . . ? C22B C16A C18B C19B 7(2) . . . . ? C24B C16A C18B C19B -114(2) . . . . ? C17B C16A C18B C23A -161(3) . . . . ? C16B C16A C18B C23A -95(2) . . . . ? O2A C16A C18B C23A -141(2) . . . . ? N1A C16A C18B C23A 3(3) . . . . ? C17A C16A C18B C23A 145(4) . . . . ? N1B C16A C18B C23A -35(3) . . . . ? C22B C16A C18B C23A 122(2) . . . . ? C24B C16A C18B C23A 1(2) . . . . ? C17B C16A C18B C19A -27(4) . . . . ? C16B C16A C18B C19A 40(5) . . . . ? O2A C16A C18B C19A -7(6) . . . . ? N1A C16A C18B C19A 138(4) . . . . ? C17A C16A C18B C19A -80(3) . . . . ? N1B C16A C18B C19A 99(4) . . . . ? C22B C16A C18B C19A -104(4) . . . . ? C24B C16A C18B C19A 135(4) . . . . ? C17B C16A C18B C24A 179(2) . . . . ? C16B C16A C18B C24A -114.1(16) . . . . ? O2A C16A C18B C24A -161(3) . . . . ? N1A C16A C18B C24A -16.3(14) . . . . ? C17A C16A C18B C24A 126(3) . . . . ? N1B C16A C18B C24A -54.6(15) . . . . ? C22B C16A C18B C24A 102.3(12) . . . . ? C24B C16A C18B C24A -19.0(9) . . . . ? C23B C23A C18B C18A -157(5) . . . . ? C22A C23A C18B C18A -20(5) . . . . ? C22B C23A C18B C18A 123(3) 5_655 . . . ? C24A C23A C18B C18A 165(3) . . . . ? C21B C23A C18B C18A 60(3) . . . . ? C23B C23A C18B C17A 106(6) . . . . ? C22A C23A C18B C17A -117(6) . . . . ? C22B C23A C18B C17A 26(5) 5_655 . . . ? C24A C23A C18B C17A 68(5) . . . . ? C18A C23A C18B C17A -97(5) . . . . ? C21B C23A C18B C17A -37(5) . . . . ? C23B C23A C18B C17B -13(6) . . . . ? C22A C23A C18B C17B 124(5) . . . . ? C22B C23A C18B C17B -93(6) 5_655 . . . ? C24A C23A C18B C17B -51(6) . . . . ? C18A C23A C18B C17B 144(8) . . . . ? C21B C23A C18B C17B -156(5) . . . . ? C22A C23A C18B C23B 137(6) . . . . ? C22B C23A C18B C23B -79(4) 5_655 . . . ? C24A C23A C18B C23B -38(3) . . . . ? C18A C23A C18B C23B 157(5) . . . . ? C21B C23A C18B C23B -142(4) . . . . ? C23B C23A C18B C16A 11(4) . . . . ? C22A C23A C18B C16A 148(3) . . . . ? C22B C23A C18B C16A -68(3) 5_655 . . . ? C24A C23A C18B C16A -27(2) . . . . ? C18A C23A C18B C16A 168(5) . . . . ? C21B C23A C18B C16A -132(2) . . . . ? C23B C23A C18B C19B 144(4) . . . . ? C22A C23A C18B C19B -78(4) . . . . ? C22B C23A C18B C19B 65.2(19) 5_655 . . . ? C24A C23A C18B C19B 106.7(18) . . . . ? C18A C23A C18B C19B -58(2) . . . . ? C21B C23A C18B C19B 2(2) . . . . ? C23B C23A C18B C19A -150(4) . . . . ? C22A C23A C18B C19A -13(4) . . . . ? C22B C23A C18B C19A 130.9(16) 5_655 . . . ? C24A C23A C18B C19A 172.4(15) . . . . ? C18A C23A C18B C19A 7(2) . . . . ? C21B C23A C18B C19A 67.7(16) . . . . ? C23B C23A C18B C24A 38(3) . . . . ? C22A C23A C18B C24A 175(4) . . . . ? C22B C23A C18B C24A -41.5(13) 5_655 . . . ? C18A C23A C18B C24A -165(3) . . . . ? C21B C23A C18B C24A -104.7(15) . . . . ? C20A C19A C18B C18A 24(6) . . . . ? C20B C19A C18B C18A -39(6) . . . . ? C19B C19A C18B C18A -75(6) . . . . ? C18A C19A C18B C17A 130(8) . . . . ? C20A C19A C18B C17A 154(2) . . . . ? C20B C19A C18B C17A 91(3) . . . . ? C19B C19A C18B C17A 55(3) . . . . ? C18A C19A C18B C17B -177(8) . . . . ? C20A C19A C18B C17B -153.5(18) . . . . ? C20B C19A C18B C17B 144(3) . . . . ? C19B C19A C18B C17B 108(3) . . . . ? C18A C19A C18B C23B -29(5) . . . . ? C20A C19A C18B C23B -6(3) . . . . ? C20B C19A C18B C23B -68.2(19) . . . . ? C19B C19A C18B C23B -104(2) . . . . ? C18A C19A C18B C16A -159(9) . . . . ? C20A C19A C18B C16A -136(4) . . . . ? C20B C19A C18B C16A 162(4) . . . . ? C19B C19A C18B C16A 125(4) . . . . ? C18A C19A C18B C19B 75(6) . . . . ? C20A C19A C18B C19B 98.8(14) . . . . ? C20B C19A C18B C19B 36.2(9) . . . . ? C18A C19A C18B C23A -18(5) . . . . ? C20A C19A C18B C23A 5.6(19) . . . . ? C20B C19A C18B C23A -56.9(12) . . . . ? C19B C19A C18B C23A -93.2(14) . . . . ? C18A C19A C18B C24A -11(4) . . . . ? C20A C19A C18B C24A 12(3) . . . . ? C20B C19A C18B C24A -50(2) . . . . ? C19B C19A C18B C24A -86(2) . . . . ? C24B C24A C18B C18A -133(3) . . . . ? C23B C24A C18B C18A -41(3) . . . . ? C22B C24A C18B C18A 37(4) 5_655 . . . ? N1A C24A C18B C18A -154(4) . . . . ? C23A C24A C18B C18A -13(3) . . . . ? C19B C24A C18B C18A 154(3) 5_655 . . . ? C17A C24A C18B C18A 94(3) 5_655 . . . ? C24B C24A C18B C17A 93(3) . . . . ? C23B C24A C18B C17A -175(4) . . . . ? C22B C24A C18B C17A -97(3) 5_655 . . . ? N1A C24A C18B C17A 72(3) . . . . ? C23A C24A C18B C17A -147(4) . . . . ? C19B C24A C18B C17A 20(4) 5_655 . . . ? C17A C24A C18B C17A -40(4) 5_655 . . . ? C24B C24A C18B C17B 37(3) . . . . ? C23B C24A C18B C17B 130(4) . . . . ? C22B C24A C18B C17B -152(2) 5_655 . . . ? N1A C24A C18B C17B 16(2) . . . . ? C23A C24A C18B C17B 157(3) . . . . ? C19B C24A C18B C17B -35(3) 5_655 . . . ? C17A C24A C18B C17B -95(3) 5_655 . . . ? C24B C24A C18B C23B -93(3) . . . . ? C22B C24A C18B C23B 78(3) 5_655 . . . ? N1A C24A C18B C23B -114(3) . . . . ? C23A C24A C18B C23B 27(2) . . . . ? C19B C24A C18B C23B -165(3) 5_655 . . . ? C17A C24A C18B C23B 135(2) 5_655 . . . ? C24B C24A C18B C16A 36.8(17) . . . . ? C23B C24A C18B C16A 129(3) . . . . ? C22B C24A C18B C16A -152.9(17) 5_655 . . . ? N1A C24A C18B C16A 15.6(13) . . . . ? C23A C24A C18B C16A 156.6(18) . . . . ? C19B C24A C18B C16A -35.8(19) 5_655 . . . ? C17A C24A C18B C16A -95.8(17) 5_655 . . . ? C24B C24A C18B C19B 162.8(17) . . . . ? C23B C24A C18B C19B -105(3) . . . . ? C22B C24A C18B C19B -27(2) 5_655 . . . ? N1A C24A C18B C19B 141.7(17) . . . . ? C23A C24A C18B C19B -77.4(15) . . . . ? C19B C24A C18B C19B 90.3(15) 5_655 . . . ? C17A C24A C18B C19B 30.3(16) 5_655 . . . ? C24B C24A C18B C23A -119.8(16) . . . . ? C23B C24A C18B C23A -27(2) . . . . ? C22B C24A C18B C23A 50.5(16) 5_655 . . . ? N1A C24A C18B C23A -141.0(15) . . . . ? C19B C24A C18B C23A 167.6(16) 5_655 . . . ? C17A C24A C18B C23A 107.6(13) 5_655 . . . ? C24B C24A C18B C19A -129(2) . . . . ? C23B C24A C18B C19A -36(2) . . . . ? C22B C24A C18B C19A 41(2) 5_655 . . . ? N1A C24A C18B C19A -150(2) . . . . ? C23A C24A C18B C19A -9.2(18) . . . . ? C19B C24A C18B C19A 158.4(19) 5_655 . . . ? C17A C24A C18B C19A 98.4(18) 5_655 . . . ? C22A C23A C23B C24A 108(7) . . . . ? C22B C23A C23B C24A -16(2) 5_655 . . . ? C18A C23A C23B C24A -133(2) . . . . ? C21B C23A C23B C24A -60(4) . . . . ? C18B C23A C23B C24A -122(4) . . . . ? C22A C23A C23B C18B -130(6) . . . . ? C22B C23A C23B C18B 106(3) 5_655 . . . ? C24A C23A C23B C18B 122(4) . . . . ? C18A C23A C23B C18B -11(3) . . . . ? C21B C23A C23B C18B 62(5) . . . . ? C22A C23A C23B C18A -120(6) . . . . ? C22B C23A C23B C18A 117.0(15) 5_655 . . . ? C24A C23A C23B C18A 133(2) . . . . ? C21B C23A C23B C18A 73(4) . . . . ? C18B C23A C23B C18A 11(3) . . . . ? C22A C23A C23B C24B 72(8) . . . . ? C22B C23A C23B C24B -51(5) 5_655 . . . ? C24A C23A C23B C24B -36(3) . . . . ? C18A C23A C23B C24B -168(4) . . . . ? C21B C23A C23B C24B -96(5) . . . . ? C18B C23A C23B C24B -158(6) . . . . ? C22A C23A C23B C22B 123(7) . . . 5_655 ? C24A C23A C23B C22B 16(2) . . . 5_655 ? C18A C23A C23B C22B -117.0(15) . . . 5_655 ? C21B C23A C23B C22B -44(3) . . . 5_655 ? C18B C23A C23B C22B -106(3) . . . 5_655 ? C22B C23A C23B C22A -123(7) 5_655 . . . ? C24A C23A C23B C22A -108(7) . . . . ? C18A C23A C23B C22A 120(6) . . . . ? C21B C23A C23B C22A -168(10) . . . . ? C18B C23A C23B C22A 130(6) . . . . ? C22A C23A C23B N1A 92(10) . . . . ? C22B C23A C23B N1A -31(8) 5_655 . . . ? C24A C23A C23B N1A -16(6) . . . . ? C18A C23A C23B N1A -148(8) . . . . ? C21B C23A C23B N1A -76(9) . . . . ? C18B C23A C23B N1A -138(10) . . . . ? C24B C24A C23B C23A -144(3) . . . . ? C22B C24A C23B C23A 18(3) 5_655 . . . ? N1A C24A C23B C23A -173(3) . . . . ? C19B C24A C23B C23A 153(3) 5_655 . . . ? C17A C24A C23B C23A 58(3) 5_655 . . . ? C18B C24A C23B C23A 126(4) . . . . ? C24B C24A C23B C18B 90(2) . . . . ? C22B C24A C23B C18B -108(2) 5_655 . . . ? N1A C24A C23B C18B 61(2) . . . . ? C23A C24A C23B C18B -126(4) . . . . ? C19B C24A C23B C18B 26(4) 5_655 . . . ? C17A C24A C23B C18B -68(3) 5_655 . . . ? C24B C24A C23B C18A 118(3) . . . . ? C22B C24A C23B C18A -80(3) 5_655 . . . ? N1A C24A C23B C18A 89(3) . . . . ? C23A C24A C23B C18A -98(5) . . . . ? C19B C24A C23B C18A 54(5) 5_655 . . . ? C17A C24A C23B C18A -40(4) 5_655 . . . ? C18B C24A C23B C18A 28.0(19) . . . . ? C22B C24A C23B C24B 162.1(19) 5_655 . . . ? N1A C24A C23B C24B -28.9(11) . . . . ? C23A C24A C23B C24B 144(3) . . . . ? C19B C24A C23B C24B -64(3) 5_655 . . . ? C17A C24A C23B C24B -158(3) 5_655 . . . ? C18B C24A C23B C24B -90(2) . . . . ? C24B C24A C23B C22B -162.1(19) . . . 5_655 ? N1A C24A C23B C22B 169.1(16) . . . 5_655 ? C23A C24A C23B C22B -18(3) . . . 5_655 ? C19B C24A C23B C22B 134(4) 5_655 . . 5_655 ? C17A C24A C23B C22B 39.7(18) 5_655 . . 5_655 ? C18B C24A C23B C22B 108(2) . . . 5_655 ? C24B C24A C23B C22A -128.0(15) . . . . ? C22B C24A C23B C22A 34.0(17) 5_655 . . . ? N1A C24A C23B C22A -156.9(12) . . . . ? C23A C24A C23B C22A 16(2) . . . . ? C19B C24A C23B C22A 168(3) 5_655 . . . ? C17A C24A C23B C22A 74(2) 5_655 . . . ? C18B C24A C23B C22A 142(3) . . . . ? C24B C24A C23B N1A 28.9(11) . . . . ? C22B C24A C23B N1A -169.1(16) 5_655 . . . ? C23A C24A C23B N1A 173(3) . . . . ? C19B C24A C23B N1A -35(3) 5_655 . . . ? C17A C24A C23B N1A -129(2) 5_655 . . . ? C18B C24A C23B N1A -61(2) . . . . ? C18A C18B C23B C23A 20(5) . . . . ? C17A C18B C23B C23A -112(6) . . . . ? C17B C18B C23B C23A 172(4) . . . . ? C16A C18B C23B C23A -171(3) . . . . ? C19B C18B C23B C23A -38(4) . . . . ? C19A C18B C23B C23A 30(4) . . . . ? C24A C18B C23B C23A -121(5) . . . . ? C18A C18B C23B C24A 140(3) . . . . ? C17A C18B C23B C24A 9(7) . . . . ? C17B C18B C23B C24A -67(4) . . . . ? C16A C18B C23B C24A -50(3) . . . . ? C19B C18B C23B C24A 83(3) . . . . ? C23A C18B C23B C24A 121(5) . . . . ? C19A C18B C23B C24A 150.7(19) . . . . ? C17A C18B C23B C18A -131(8) . . . . ? C17B C18B C23B C18A 152(6) . . . . ? C16A C18B C23B C18A 170(4) . . . . ? C19B C18B C23B C18A -57(2) . . . . ? C23A C18B C23B C18A -20(5) . . . . ? C19A C18B C23B C18A 10.2(18) . . . . ? C24A C18B C23B C18A -140(3) . . . . ? C18A C18B C23B C24B -176(3) . . . . ? C17A C18B C23B C24B 53(7) . . . . ? C17B C18B C23B C24B -23(4) . . . . ? C16A C18B C23B C24B -6(2) . . . . ? C19B C18B C23B C24B 127(2) . . . . ? C23A C18B C23B C24B 165(4) . . . . ? C19A C18B C23B C24B -165.5(15) . . . . ? C24A C18B C23B C24B 43.8(15) . . . . ? C18A C18B C23B C22B 88(4) . . . 5_655 ? C17A C18B C23B C22B -43(7) . . . 5_655 ? C17B C18B C23B C22B -120(4) . . . 5_655 ? C16A C18B C23B C22B -102(2) . . . 5_655 ? C19B C18B C23B C22B 31(3) . . . 5_655 ? C23A C18B C23B C22B 68(3) . . . 5_655 ? C19A C18B C23B C22B 98(2) . . . 5_655 ? C24A C18B C23B C22B -53(2) . . . 5_655 ? C18A C18B C23B C22A 5(4) . . . . ? C17A C18B C23B C22A -126(5) . . . . ? C17B C18B C23B C22A 158(3) . . . . ? C16A C18B C23B C22A 174.9(17) . . . . ? C19B C18B C23B C22A -52(3) . . . . ? C23A C18B C23B C22A -14(2) . . . . ? C19A C18B C23B C22A 15(3) . . . . ? C24A C18B C23B C22A -135(3) . . . . ? C18A C18B C23B N1A -175(3) . . . . ? C17A C18B C23B N1A 53(6) . . . . ? C17B C18B C23B N1A -23(4) . . . . ? C16A C18B C23B N1A -5.5(17) . . . . ? C19B C18B C23B N1A 128(2) . . . . ? C23A C18B C23B N1A 165(4) . . . . ? C19A C18B C23B N1A -164.9(16) . . . . ? C24A C18B C23B N1A 44.4(17) . . . . ? C18B C18A C23B C23A -162(4) . . . . ? C19A C18A C23B C23A 44(4) . . . . ? C17A C18A C23B C23A -148(3) . . . . ? C19B C18A C23B C23A -84(3) . . . . ? C20B C18A C23B C23A -34(3) . . . . ? C17B C18A C23B C23A -176(3) . . . . ? C18B C18A C23B C24A -54(4) . . . . ? C19A C18A C23B C24A 152(2) . . . . ? C17A C18A C23B C24A -40(3) . . . . ? C19B C18A C23B C24A 24(4) . . . . ? C23A C18A C23B C24A 108(4) . . . . ? C20B C18A C23B C24A 74(3) . . . . ? C17B C18A C23B C24A -68(3) . . . . ? C19A C18A C23B C18B -153(5) . . . . ? C17A C18A C23B C18B 14(3) . . . . ? C19B C18A C23B C18B 78(3) . . . . ? C23A C18A C23B C18B 162(4) . . . . ? C20B C18A C23B C18B 129(3) . . . . ? C17B C18A C23B C18B -13(3) . . . . ? C18B C18A C23B C24B 6(4) . . . . ? C19A C18A C23B C24B -147(2) . . . . ? C17A C18A C23B C24B 20(3) . . . . ? C19B C18A C23B C24B 84(3) . . . . ? C23A C18A C23B C24B 168(5) . . . . ? C20B C18A C23B C24B 135(2) . . . . ? C17B C18A C23B C24B -7(3) . . . . ? C18B C18A C23B C22B -106(4) . . . 5_655 ? C19A C18A C23B C22B 100(3) . . . 5_655 ? C17A C18A C23B C22B -92.0(19) . . . 5_655 ? C19B C18A C23B C22B -28(2) . . . 5_655 ? C23A C18A C23B C22B 56(3) . . . 5_655 ? C20B C18A C23B C22B 22(2) . . . 5_655 ? C17B C18A C23B C22B -119.8(17) . . . 5_655 ? C18B C18A C23B C22A -176(3) . . . . ? C19A C18A C23B C22A 31(3) . . . . ? C17A C18A C23B C22A -161.4(12) . . . . ? C19B C18A C23B C22A -97.6(15) . . . . ? C23A C18A C23B C22A -13.4(19) . . . . ? C20B C18A C23B C22A -47.1(12) . . . . ? C17B C18A C23B C22A 170.9(10) . . . . ? C18B C18A C23B N1A 5(3) . . . . ? C19A C18A C23B N1A -148(2) . . . . ? C17A C18A C23B N1A 19.5(18) . . . . ? C19B C18A C23B N1A 83(2) . . . . ? C23A C18A C23B N1A 168(4) . . . . ? C20B C18A C23B N1A 133.8(14) . . . . ? C17B C18A C23B N1A -8.2(14) . . . . ? C21A C22A C23B C23A -79(7) . . . . ? C21B C22A C23B C23A 8(6) . . . . ? C23A C22A C23B C24A -78(7) . . . . ? C21A C22A C23B C24A -156.1(14) . . . . ? C21B C22A C23B C24A -69.2(17) . . . . ? C23A C22A C23B C18B 57(6) . . . . ? C21A C22A C23B C18B -22(3) . . . . ? C21B C22A C23B C18B 65(3) . . . . ? C23A C22A C23B C18A 60(6) . . . . ? C21A C22A C23B C18A -18.7(18) . . . . ? C21B C22A C23B C18A 68.2(14) . . . . ? C23A C22A C23B C24B -122(8) . . . . ? C21A C22A C23B C24B 159.7(17) . . . . ? C21B C22A C23B C24B -113(2) . . . . ? C23A C22A C23B C22B -51(6) . . . 5_655 ? C21A C22A C23B C22B -129.5(14) . . . 5_655 ? C21B C22A C23B C22B -42.6(11) . . . 5_655 ? C23A C22A C23B N1A -122(9) . . . . ? C21A C22A C23B N1A 159(3) . . . . ? C21B C22A C23B N1A -114(3) . . . . ? C24B N1A C23B C23A -37(8) . . . . ? N1B N1A C23B C23A -129(8) . . . . ? C16A N1A C23B C23A 149(8) . . . . ? C24A N1A C23B C23A 19(8) . . . . ? C19B N1A C23B C23A 38(8) 5_655 . . . ? C16B N1A C23B C23A -177(8) . . . . ? C24B N1A C23B C24A -56(3) . . . . ? N1B N1A C23B C24A -148.1(19) . . . . ? C16A N1A C23B C24A 129.7(18) . . . . ? C19B N1A C23B C24A 18.5(14) 5_655 . . . ? C16B N1A C23B C24A 164.4(16) . . . . ? C24B N1A C23B C18B -179(4) . . . . ? N1B N1A C23B C18B 89(2) . . . . ? C16A N1A C23B C18B 7(2) . . . . ? C24A N1A C23B C18B -123(2) . . . . ? C19B N1A C23B C18B -105(2) 5_655 . . . ? C16B N1A C23B C18B 41(2) . . . . ? C24B N1A C23B C18A 179(3) . . . . ? N1B N1A C23B C18A 86.0(18) . . . . ? C16A N1A C23B C18A 3.7(19) . . . . ? C24A N1A C23B C18A -126(2) . . . . ? C19B N1A C23B C18A -107.5(16) 5_655 . . . ? C16B N1A C23B C18A 38.5(18) . . . . ? N1B N1A C23B C24B -93(4) . . . . ? C16A N1A C23B C24B -175(4) . . . . ? C24A N1A C23B C24B 56(3) . . . . ? C19B N1A C23B C24B 74(3) 5_655 . . . ? C16B N1A C23B C24B -140(4) . . . . ? C24B N1A C23B C22B -64(3) . . . 5_655 ? N1B N1A C23B C22B -156.4(13) . . . 5_655 ? C16A N1A C23B C22B 121.4(13) . . . 5_655 ? C24A N1A C23B C22B -8.3(12) . . . 5_655 ? C19B N1A C23B C22B 10.2(12) 5_655 . . 5_655 ? C16B N1A C23B C22B 156.1(11) . . . 5_655 ? C24B N1A C23B C22A 1(5) . . . . ? N1B N1A C23B C22A -92(3) . . . . ? C16A N1A C23B C22A -174(3) . . . . ? C24A N1A C23B C22A 56(3) . . . . ? C19B N1A C23B C22A 75(4) 5_655 . . . ? C16B N1A C23B C22A -139(3) . . . . ? N1B N1A C24B C24A 156.2(13) . . . . ? C16A N1A C24B C24A 54(7) . . . . ? C19B N1A C24B C24A -62.2(17) 5_655 . . . ? C23B N1A C24B C24A 44.1(15) . . . . ? C16B N1A C24B C24A 117(4) . . . . ? C16A N1A C24B N1B -102(6) . . . . ? C24A N1A C24B N1B -156.2(13) . . . . ? C19B N1A C24B N1B 141.6(16) 5_655 . . . ? C23B N1A C24B N1B -112.2(18) . . . . ? C16B N1A C24B N1B -39(3) . . . . ? N1B N1A C24B C23B 112.2(18) . . . . ? C16A N1A C24B C23B 10(7) . . . . ? C24A N1A C24B C23B -44.1(15) . . . . ? C19B N1A C24B C23B -106.3(16) 5_655 . . . ? C16B N1A C24B C23B 73(4) . . . . ? N1B N1A C24B C19B -141.6(16) . . . 5_655 ? C16A N1A C24B C19B 116(6) . . . 5_655 ? C24A N1A C24B C19B 62.2(17) . . . 5_655 ? C23B N1A C24B C19B 106.3(16) . . . 5_655 ? C16B N1A C24B C19B 179(4) . . . 5_655 ? N1B N1A C24B C16A 102(6) . . . . ? C24A N1A C24B C16A -54(7) . . . . ? C19B N1A C24B C16A -116(6) 5_655 . . . ? C23B N1A C24B C16A -10(7) . . . . ? C16B N1A C24B C16A 63(4) . . . . ? C23B C24A C24B N1A -85(3) . . . . ? C22B C24A C24B N1A 165(5) 5_655 . . . ? C23A C24A C24B N1A -105(3) . . . . ? C19B C24A C24B N1A 64(2) 5_655 . . . ? C17A C24A C24B N1A 75(3) 5_655 . . . ? C18B C24A C24B N1A -46(3) . . . . ? C23B C24A C24B N1B -54(3) . . . . ? C22B C24A C24B N1B -164(5) 5_655 . . . ? N1A C24A C24B N1B 31.5(18) . . . . ? C23A C24A C24B N1B -73(3) . . . . ? C19B C24A C24B N1B 96(3) 5_655 . . . ? C17A C24A C24B N1B 107(3) 5_655 . . . ? C18B C24A C24B N1B -14(3) . . . . ? C22B C24A C24B C23B -110(6) 5_655 . . . ? N1A C24A C24B C23B 85(3) . . . . ? C23A C24A C24B C23B -19.3(14) . . . . ? C19B C24A C24B C23B 149.5(16) 5_655 . . . ? C17A C24A C24B C23B 161(3) 5_655 . . . ? C18B C24A C24B C23B 39.8(14) . . . . ? C23B C24A C24B C19B -149.5(16) . . . 5_655 ? C22B C24A C24B C19B 100(6) 5_655 . . 5_655 ? N1A C24A C24B C19B -64(2) . . . 5_655 ? C23A C24A C24B C19B -169(2) . . . 5_655 ? C17A C24A C24B C19B 11.2(17) 5_655 . . 5_655 ? C18B C24A C24B C19B -109.7(12) . . . 5_655 ? C23B C24A C24B C16A -68.4(14) . . . . ? C22B C24A C24B C16A -179(6) 5_655 . . . ? N1A C24A C24B C16A 17(2) . . . . ? C23A C24A C24B C16A -87.7(19) . . . . ? C19B C24A C24B C16A 81.2(9) 5_655 . . . ? C17A C24A C24B C16A 92.3(17) 5_655 . . . ? C18B C24A C24B C16A -28.6(12) . . . . ? C16B N1B C24B N1A 40(3) . . . . ? C16A N1B C24B N1A 26(2) . . . . ? N1A N1B C24B C24A -44(3) . . . . ? C16B N1B C24B C24A -4(3) . . . . ? C16A N1B C24B C24A -18(3) . . . . ? N1A N1B C24B C23B -81(2) . . . . ? C16B N1B C24B C23B -40.7(16) . . . . ? C16A N1B C24B C23B -54.9(12) . . . . ? N1A N1B C24B C19B 39.1(19) . . . 5_655 ? C16B N1B C24B C19B 79.0(15) . . . 5_655 ? C16A N1B C24B C19B 64.9(12) . . . 5_655 ? N1A N1B C24B C16A -26(2) . . . . ? C16B N1B C24B C16A 14.2(11) . . . . ? C23A C23B C24B N1A 161(5) . . . . ? C24A C23B C24B N1A 105(3) . . . . ? C18B C23B C24B N1A 1(4) . . . . ? C18A C23B C24B N1A -2(4) . . . . ? C22B C23B C24B N1A 118(3) 5_655 . . . ? C22A C23B C24B N1A -180(3) . . . . ? C23A C23B C24B C24A 56(5) . . . . ? C18B C23B C24B C24A -103(3) . . . . ? C18A C23B C24B C24A -107(3) . . . . ? C22B C23B C24B C24A 13.4(14) 5_655 . . . ? C22A C23B C24B C24A 76(2) . . . . ? N1A C23B C24B C24A -105(3) . . . . ? C23A C23B C24B N1B -153(4) . . . . ? C24A C23B C24B N1B 151(2) . . . . ? C18B C23B C24B N1B 48(2) . . . . ? C18A C23B C24B N1B 44(3) . . . . ? C22B C23B C24B N1B 164.2(12) 5_655 . . . ? C22A C23B C24B N1B -133.3(18) . . . . ? N1A C23B C24B N1B 46(2) . . . . ? C23A C23B C24B C19B 86(5) . . . 5_655 ? C24A C23B C24B C19B 30.0(16) . . . 5_655 ? C18B C23B C24B C19B -73(2) . . . 5_655 ? C18A C23B C24B C19B -77(3) . . . 5_655 ? C22B C23B C24B C19B 43.4(13) 5_655 . . 5_655 ? C22A C23B C24B C19B 105.8(19) . . . 5_655 ? N1A C23B C24B C19B -75(3) . . . 5_655 ? C23A C23B C24B C16A 164(5) . . . . ? C24A C23B C24B C16A 108.1(17) . . . . ? C18B C23B C24B C16A 5(2) . . . . ? C18A C23B C24B C16A 2(3) . . . . ? C22B C23B C24B C16A 121.5(11) 5_655 . . . ? C22A C23B C24B C16A -176(2) . . . . ? N1A C23B C24B C16A 4(3) . . . . ? C17B C16A C24B N1A -174(7) . . . . ? C16B C16A C24B N1A -76(7) . . . . ? O2A C16A C24B N1A -44(7) . . . . ? C17A C16A C24B N1A 147(7) . . . . ? C18B C16A C24B N1A 166(7) . . . . ? N1B C16A C24B N1A -61(6) . . . . ? C22B C16A C24B N1A 91(7) . . . . ? C17B C16A C24B C24A 57(3) . . . . ? C16B C16A C24B C24A 154.9(16) . . . . ? O2A C16A C24B C24A -173.3(18) . . . . ? N1A C16A C24B C24A -129(7) . . . . ? C17A C16A C24B C24A 18.0(15) . . . . ? C18B C16A C24B C24A 37.0(18) . . . . ? N1B C16A C24B C24A 170.0(15) . . . . ? C22B C16A C24B C24A -37.6(18) . . . . ? C17B C16A C24B N1B -113(3) . . . . ? C16B C16A C24B N1B -15.1(11) . . . . ? O2A C16A C24B N1B 16.7(16) . . . . ? N1A C16A C24B N1B 61(6) . . . . ? C17A C16A C24B N1B -152.0(13) . . . . ? C18B C16A C24B N1B -133.1(16) . . . . ? C22B C16A C24B N1B 152.4(16) . . . . ? C17B C16A C24B C23B 16(3) . . . . ? C16B C16A C24B C23B 113.8(16) . . . . ? O2A C16A C24B C23B 145.6(19) . . . . ? N1A C16A C24B C23B -170(7) . . . . ? C17A C16A C24B C23B -23.0(14) . . . . ? C18B C16A C24B C23B -4.1(17) . . . . ? N1B C16A C24B C23B 128.9(13) . . . . ? C22B C16A C24B C23B -78.7(17) . . . . ? C17B C16A C24B C19B 126(2) . . . 5_655 ? C16B C16A C24B C19B -135.9(15) . . . 5_655 ? O2A C16A C24B C19B -104.2(19) . . . 5_655 ? N1A C16A C24B C19B -60(6) . . . 5_655 ? C17A C16A C24B C19B 87.2(14) . . . 5_655 ? C18B C16A C24B C19B 106.1(17) . . . 5_655 ? N1B C16A C24B C19B -120.8(14) . . . 5_655 ? C22B C16A C24B C19B 31.5(19) . . . 5_655 ? C18B C18A C19B C20B 150(2) . . . . ? C19A C18A C19B C20B -64.7(14) . . . . ? C17A C18A C19B C20B 171.2(15) . . . . ? C23B C18A C19B C20B 86.5(18) . . . . ? C23A C18A C19B C20B 55.7(15) . . . . ? C17B C18A C19B C20B 174.8(12) . . . . ? C18B C18A C19B C17A -21(2) . . . . ? C19A C18A C19B C17A 124.2(13) . . . . ? C23B C18A C19B C17A -84.7(16) . . . . ? C23A C18A C19B C17A -115.4(12) . . . . ? C20B C18A C19B C17A -171.2(15) . . . . ? C17B C18A C19B C17A 3.6(9) . . . . ? C18B C18A C19B N1A 71(3) . . . 5_655 ? C19A C18A C19B N1A -144(2) . . . 5_655 ? C17A C18A C19B N1A 92(2) . . . 5_655 ? C23B C18A C19B N1A 7(3) . . . 5_655 ? C23A C18A C19B N1A -23(3) . . . 5_655 ? C20B C18A C19B N1A -79(2) . . . 5_655 ? C17B C18A C19B N1A 96(2) . . . 5_655 ? C18B C18A C19B C24A 9(3) . . . 5_655 ? C19A C18A C19B C24A 154.4(14) . . . 5_655 ? C17A C18A C19B C24A 30.3(12) . . . 5_655 ? C23B C18A C19B C24A -54(2) . . . 5_655 ? C23A C18A C19B C24A -85.2(16) . . . 5_655 ? C20B C18A C19B C24A -140.9(19) . . . 5_655 ? C17B C18A C19B C24A 33.9(14) . . . 5_655 ? C18B C18A C19B C24B 31(4) . . . 5_655 ? C19A C18A C19B C24B 176(3) . . . 5_655 ? C17A C18A C19B C24B 52(3) . . . 5_655 ? C23B C18A C19B C24B -33(4) . . . 5_655 ? C23A C18A C19B C24B -64(3) . . . 5_655 ? C20B C18A C19B C24B -120(4) . . . 5_655 ? C17B C18A C19B C24B 55(3) . . . 5_655 ? C19A C18A C19B C18B 145(3) . . . . ? C17A C18A C19B C18B 21(2) . . . . ? C23B C18A C19B C18B -64(2) . . . . ? C23A C18A C19B C18B -94(2) . . . . ? C20B C18A C19B C18B -150(2) . . . . ? C17B C18A C19B C18B 25(2) . . . . ? C18B C18A C19B C19A -145(3) . . . . ? C17A C18A C19B C19A -124.2(13) . . . . ? C23B C18A C19B C19A 151(2) . . . . ? C23A C18A C19B C19A 120.4(16) . . . . ? C20B C18A C19B C19A 64.7(14) . . . . ? C17B C18A C19B C19A -120.5(12) . . . . ? C18B C17A C19B C20B 7(3) . . . . ? C17B C17A C19B C20B -41(8) . . . . ? C22B C17A C19B C20B 145(2) . . . . ? C18A C17A C19B C20B -13(2) . . . . ? C16A C17A C19B C20B 62(4) . . . . ? C24A C17A C19B C20B 137(3) 5_655 . . . ? C18B C17A C19B C18A 19(2) . . . . ? C17B C17A C19B C18A -28(7) . . . . ? C22B C17A C19B C18A 157.9(14) . . . . ? C16A C17A C19B C18A 75(3) . . . . ? C24A C17A C19B C18A 149.4(12) 5_655 . . . ? C18B C17A C19B N1A -114(2) . . . 5_655 ? C17B C17A C19B N1A -161(7) . . . 5_655 ? C22B C17A C19B N1A 25.0(19) . . . 5_655 ? C18A C17A C19B N1A -132.9(15) . . . 5_655 ? C16A C17A C19B N1A -58(3) . . . 5_655 ? C24A C17A C19B N1A 16.4(12) 5_655 . . 5_655 ? C18B C17A C19B C24A -130(2) . . . 5_655 ? C17B C17A C19B C24A -177(7) . . . 5_655 ? C22B C17A C19B C24A 8.5(12) . . . 5_655 ? C18A C17A C19B C24A -149.4(12) . . . 5_655 ? C16A C17A C19B C24A -74(3) . . . 5_655 ? C18B C17A C19B C24B -137(2) . . . 5_655 ? C17B C17A C19B C24B 176(7) . . . 5_655 ? C22B C17A C19B C24B 1.8(16) . . . 5_655 ? C18A C17A C19B C24B -156.1(14) . . . 5_655 ? C16A C17A C19B C24B -81(3) . . . 5_655 ? C24A C17A C19B C24B -6.7(10) 5_655 . . 5_655 ? C17B C17A C19B C18B -47(7) . . . . ? C22B C17A C19B C18B 139(3) . . . . ? C18A C17A C19B C18B -19(2) . . . . ? C16A C17A C19B C18B 56(4) . . . . ? C24A C17A C19B C18B 130(2) 5_655 . . . ? C18B C17A C19B C19A 51(2) . . . . ? C17B C17A C19B C19A 3(7) . . . . ? C22B C17A C19B C19A -170.9(11) . . . . ? C18A C17A C19B C19A 31.2(7) . . . . ? C16A C17A C19B C19A 106(3) . . . . ? C24A C17A C19B C19A -179.4(10) 5_655 . . . ? C18A C18B C19B C20B -31(3) . . . . ? C17A C18B C19B C20B -175(2) . . . . ? C17B C18B C19B C20B -166(2) . . . . ? C23B C18B C19B C20B 39(3) . . . . ? C16A C18B C19B C20B 154.1(18) . . . . ? C23A C18B C19B C20B 25(2) . . . . ? C19A C18B C19B C20B -53.7(15) . . . . ? C24A C18B C19B C20B 71(2) . . . . ? C17A C18B C19B C18A -145(4) . . . . ? C17B C18B C19B C18A -135(4) . . . . ? C23B C18B C19B C18A 70(2) . . . . ? C16A C18B C19B C18A -175(4) . . . . ? C23A C18B C19B C18A 56.0(17) . . . . ? C19A C18B C19B C18A -23.2(19) . . . . ? C24A C18B C19B C18A 101(2) . . . . ? C18A C18B C19B C17A 145(4) . . . . ? C17B C18B C19B C17A 9.6(13) . . . . ? C23B C18B C19B C17A -146(4) . . . . ? C16A C18B C19B C17A -30.7(16) . . . . ? C23A C18B C19B C17A -159(3) . . . . ? C19A C18B C19B C17A 122(2) . . . . ? C24A C18B C19B C17A -114(3) . . . . ? C18A C18B C19B N1A -131(3) . . . 5_655 ? C17A C18B C19B N1A 84(2) . . . 5_655 ? C17B C18B C19B N1A 94(2) . . . 5_655 ? C23B C18B C19B N1A -62(3) . . . 5_655 ? C16A C18B C19B N1A 53(2) . . . 5_655 ? C23A C18B C19B N1A -75.3(19) . . . 5_655 ? C19A C18B C19B N1A -154.5(16) . . . 5_655 ? C24A C18B C19B N1A -30(2) . . . 5_655 ? C18A C18B C19B C24A -172(2) . . . 5_655 ? C17A C18B C19B C24A 44(2) . . . 5_655 ? C17B C18B C19B C24A 53(2) . . . 5_655 ? C23B C18B C19B C24A -102(2) . . . 5_655 ? C16A C18B C19B C24A 13(2) . . . 5_655 ? C23A C18B C19B C24A -115.7(13) . . . 5_655 ? C19A C18B C19B C24A 165.2(11) . . . 5_655 ? C24A C18B C19B C24A -70.6(13) . . . 5_655 ? C18A C18B C19B C24B -162(2) . . . 5_655 ? C17A C18B C19B C24B 53(3) . . . 5_655 ? C17B C18B C19B C24B 63(3) . . . 5_655 ? C23B C18B C19B C24B -93(2) . . . 5_655 ? C16A C18B C19B C24B 22(3) . . . 5_655 ? C23A C18B C19B C24B -106.2(17) . . . 5_655 ? C19A C18B C19B C24B 174.7(16) . . . 5_655 ? C24A C18B C19B C24B -61.1(18) . . . 5_655 ? C18A C18B C19B C19A 23.2(19) . . . . ? C17A C18B C19B C19A -122(2) . . . . ? C17B C18B C19B C19A -112(2) . . . . ? C23B C18B C19B C19A 93(2) . . . . ? C16A C18B C19B C19A -152(2) . . . . ? C23A C18B C19B C19A 79.1(11) . . . . ? C24A C18B C19B C19A 124.3(12) . . . . ? C18A C19A C19B C20B 103.8(16) . . . . ? C20A C19A C19B C20B 3.7(14) . . . . ? C18B C19A C19B C20B 121.7(14) . . . . ? C20A C19A C19B C18A -100.1(14) . . . . ? C20B C19A C19B C18A -103.8(16) . . . . ? C18B C19A C19B C18A 18.0(14) . . . . ? C18A C19A C19B C17A -44.9(13) . . . . ? C20A C19A C19B C17A -145.0(10) . . . . ? C20B C19A C19B C17A -148.7(16) . . . . ? C18B C19A C19B C17A -26.9(9) . . . . ? C18A C19A C19B N1A 96(4) . . . 5_655 ? C20A C19A C19B N1A -4(4) . . . 5_655 ? C20B C19A C19B N1A -8(3) . . . 5_655 ? C18B C19A C19B N1A 114(4) . . . 5_655 ? C18A C19A C19B C24A -46(2) . . . 5_655 ? C20A C19A C19B C24A -146(2) . . . 5_655 ? C20B C19A C19B C24A -150(3) . . . 5_655 ? C18B C19A C19B C24A -28(2) . . . 5_655 ? C18A C19A C19B C24B -165(11) . . . 5_655 ? C20A C19A C19B C24B 95(11) . . . 5_655 ? C20B C19A C19B C24B 91(11) . . . 5_655 ? C18B C19A C19B C24B -147(11) . . . 5_655 ? C18A C19A C19B C18B -18.0(14) . . . . ? C20A C19A C19B C18B -118.0(11) . . . . ? C20B C19A C19B C18B -121.7(14) . . . . ? C18A C19B C20B C21B -73(2) . . . . ? C17A C19B C20B C21B -62(4) . . . . ? N1A C19B C20B C21B 66(2) 5_655 . . . ? C24A C19B C20B C21B 44(4) 5_655 . . . ? C24B C19B C20B C21B 78(2) 5_655 . . . ? C18B C19B C20B C21B -58(3) . . . . ? C19A C19B C20B C21B -111(2) . . . . ? C17A C19B C20B C18A 10.9(19) . . . . ? N1A C19B C20B C18A 139.2(14) 5_655 . . . ? C24A C19B C20B C18A 117(3) 5_655 . . . ? C24B C19B C20B C18A 151.2(17) 5_655 . . . ? C18B C19B C20B C18A 14.5(14) . . . . ? C19A C19B C20B C18A -37.8(8) . . . . ? C18A C19B C20B C19A 37.8(8) . . . . ? C17A C19B C20B C19A 49(2) . . . . ? N1A C19B C20B C19A 177.0(11) 5_655 . . . ? C24A C19B C20B C19A 154(3) 5_655 . . . ? C24B C19B C20B C19A -171.0(14) 5_655 . . . ? C18B C19B C20B C19A 52.3(16) . . . . ? C18B C18A C20B C21B 80(3) . . . . ? C19A C18A C20B C21B -129.3(14) . . . . ? C17A C18A C20B C21B 112.1(14) . . . . ? C23B C18A C20B C21B 11.7(17) . . . . ? C19B C18A C20B C21B 120.7(18) . . . . ? C23A C18A C20B C21B -4.7(14) . . . . ? C17B C18A C20B C21B 112.4(16) . . . . ? C18B C18A C20B C19B -40(3) . . . . ? C19A C18A C20B C19B 110.0(15) . . . . ? C17A C18A C20B C19B -8.6(14) . . . . ? C23B C18A C20B C19B -109.0(15) . . . . ? C23A C18A C20B C19B -125.3(15) . . . . ? C17B C18A C20B C19B -8.3(19) . . . . ? C18B C18A C20B C19A -150(4) . . . . ? C17A C18A C20B C19A -118.6(13) . . . . ? C23B C18A C20B C19A 141.0(15) . . . . ? C19B C18A C20B C19A -110.0(15) . . . . ? C23A C18A C20B C19A 124.7(12) . . . . ? C17B C18A C20B C19A -118.3(17) . . . . ? C18A C19A C20B C21B 59.4(16) . . . . ? C20A C19A C20B C21B -66.4(15) . . . . ? C18B C19A C20B C21B 68.6(17) . . . . ? C19B C19A C20B C21B 110.2(19) . . . . ? C18A C19A C20B C19B -50.9(12) . . . . ? C20A C19A C20B C19B -176.7(12) . . . . ? C18B C19A C20B C19B -41.6(12) . . . . ? C20A C19A C20B C18A -125.8(10) . . . . ? C18B C19A C20B C18A 9.2(12) . . . . ? C19B C19A C20B C18A 50.9(12) . . . . ? C19B C20B C21B C22A 90(2) . . . . ? C18A C20B C21B C22A 41.3(16) . . . . ? C19A C20B C21B C22A 9(2) . . . . ? C19B C20B C21B C22B -1(3) . . . 5_655 ? C18A C20B C21B C22B -49(2) . . . 5_655 ? C19A C20B C21B C22B -81(2) . . . 5_655 ? C19B C20B C21B C23A 53(2) . . . . ? C18A C20B C21B C23A 4.5(14) . . . . ? C19A C20B C21B C23A -27.6(18) . . . . ? C23A C22A C21B C20B -67.6(19) . . . . ? C21A C22A C21B C20B 53.6(17) . . . . ? C23B C22A C21B C20B -69.3(16) . . . . ? C23A C22A C21B C22B 46.8(16) . . . 5_655 ? C21A C22A C21B C22B 168.1(13) . . . 5_655 ? C23B C22A C21B C22B 45.1(12) . . . 5_655 ? C21A C22A C21B C23A 121.2(14) . . . . ? C23B C22A C21B C23A -1.7(13) . . . . ? C23B C23A C21B C20B -67(4) . . . . ? C22A C23A C21B C20B 119.1(18) . . . . ? C22B C23A C21B C20B -120.1(16) 5_655 . . . ? C24A C23A C21B C20B -106.1(19) . . . . ? C18A C23A C21B C20B -5.3(16) . . . . ? C18B C23A C21B C20B -27.8(19) . . . . ? C23B C23A C21B C22A 174(5) . . . . ? C22B C23A C21B C22A 121(2) 5_655 . . . ? C24A C23A C21B C22A 135(3) . . . . ? C18A C23A C21B C22A -124.4(13) . . . . ? C18B C23A C21B C22A -146.9(18) . . . . ? C23B C23A C21B C22B 53(4) . . . 5_655 ? C22A C23A C21B C22B -121(2) . . . 5_655 ? C24A C23A C21B C22B 14.0(14) . . . 5_655 ? C18A C23A C21B C22B 114.8(18) . . . 5_655 ? C18B C23A C21B C22B 92.3(18) . . . 5_655 ? C18B C17A C22B C24A 88(5) . . . 5_655 ? C17B C17A C22B C24A 171.7(16) . . . 5_655 ? C18A C17A C22B C24A 43(5) . . . 5_655 ? C16A C17A C22B C24A 136.3(13) . . . 5_655 ? C19B C17A C22B C24A -9.8(14) . . . 5_655 ? C18B C17A C22B C23A 57(6) . . . 5_655 ? C17B C17A C22B C23A 141(3) . . . 5_655 ? C18A C17A C22B C23A 12(6) . . . 5_655 ? C16A C17A C22B C23A 106(3) . . . 5_655 ? C19B C17A C22B C23A -40(3) . . . 5_655 ? C24A C17A C22B C23A -31(2) 5_655 . . 5_655 ? C18B C17A C22B C21B -38(7) . . . 5_655 ? C17B C17A C22B C21B 46(3) . . . 5_655 ? C18A C17A C22B C21B -83(6) . . . 5_655 ? C16A C17A C22B C21B 11(3) . . . 5_655 ? C19B C17A C22B C21B -135(3) . . . 5_655 ? C24A C17A C22B C21B -126(3) 5_655 . . 5_655 ? C18B C17A C22B C16A -48(5) . . . . ? C17B C17A C22B C16A 35.5(11) . . . . ? C18A C17A C22B C16A -93(4) . . . . ? C19B C17A C22B C16A -146.1(16) . . . . ? C24A C17A C22B C16A -136.3(13) 5_655 . . . ? C18B C17A C22B C17B -84(5) . . . . ? C18A C17A C22B C17B -129(5) . . . . ? C16A C17A C22B C17B -35.5(11) . . . . ? C19B C17A C22B C17B 178(2) . . . . ? C24A C17A C22B C17B -171.7(16) 5_655 . . . ? C18B C17A C22B C23B 66(5) . . . 5_655 ? C17B C17A C22B C23B 150.2(16) . . . 5_655 ? C18A C17A C22B C23B 21(5) . . . 5_655 ? C16A C17A C22B C23B 114.8(13) . . . 5_655 ? C19B C17A C22B C23B -31.3(18) . . . 5_655 ? C24A C17A C22B C23B -21.5(10) 5_655 . . 5_655 ? C17B C16A C22B C24A -89(2) . . . 5_655 ? C16B C16A C22B C24A -159(2) . . . 5_655 ? O2A C16A C22B C24A -173.4(16) . . . 5_655 ? N1A C16A C22B C24A 53(3) . . . 5_655 ? C17A C16A C22B C24A -49(2) . . . 5_655 ? C18B C16A C22B C24A -33(2) . . . 5_655 ? N1B C16A C22B C24A 91(4) . . . 5_655 ? C24B C16A C22B C24A 40(2) . . . 5_655 ? C17B C16A C22B C17A -40.4(13) . . . . ? C16B C16A C22B C17A -110(3) . . . . ? O2A C16A C22B C17A -124.4(16) . . . . ? N1A C16A C22B C17A 101.9(16) . . . . ? C18B C16A C22B C17A 15.8(15) . . . . ? N1B C16A C22B C17A 140(3) . . . . ? C24B C16A C22B C17A 89.0(14) . . . . ? C17B C16A C22B C23A -166(3) . . . 5_655 ? C16B C16A C22B C23A 124(3) . . . 5_655 ? O2A C16A C22B C23A 110(3) . . . 5_655 ? N1A C16A C22B C23A -23(3) . . . 5_655 ? C17A C16A C22B C23A -125(3) . . . 5_655 ? C18B C16A C22B C23A -109(3) . . . 5_655 ? N1B C16A C22B C23A 15(5) . . . 5_655 ? C24B C16A C22B C23A -36(3) . . . 5_655 ? C17B C16A C22B C21B 146.9(18) . . . 5_655 ? C16B C16A C22B C21B 77(2) . . . 5_655 ? O2A C16A C22B C21B 62.9(14) . . . 5_655 ? N1A C16A C22B C21B -70.8(19) . . . 5_655 ? C17A C16A C22B C21B -172.7(19) . . . 5_655 ? C18B C16A C22B C21B -156.9(16) . . . 5_655 ? N1B C16A C22B C21B -33(4) . . . 5_655 ? C24B C16A C22B C21B -83.7(18) . . . 5_655 ? C16B C16A C22B C17B -70(3) . . . . ? O2A C16A C22B C17B -84.0(15) . . . . ? N1A C16A C22B C17B 142.3(19) . . . . ? C17A C16A C22B C17B 40.4(13) . . . . ? C18B C16A C22B C17B 56.3(14) . . . . ? N1B C16A C22B C17B -180(4) . . . . ? C24B C16A C22B C17B 129.4(17) . . . . ? C17B C16A C22B C23B -134(3) . . . 5_655 ? C16B C16A C22B C23B 156(2) . . . 5_655 ? O2A C16A C22B C23B 142(2) . . . 5_655 ? N1A C16A C22B C23B 8(3) . . . 5_655 ? C17A C16A C22B C23B -93(3) . . . 5_655 ? C18B C16A C22B C23B -78(2) . . . 5_655 ? N1B C16A C22B C23B 47(5) . . . 5_655 ? C24B C16A C22B C23B -4(3) . . . 5_655 ? C16A C17B C22B C24A 105.9(16) . . . 5_655 ? C17A C17B C22B C24A -8.7(17) . . . 5_655 ? C18B C17B C22B C24A 17.2(17) . . . 5_655 ? C16B C17B C22B C24A 136.2(16) . . . 5_655 ? O2A C17B C22B C24A 158.7(13) . . . 5_655 ? C18A C17B C22B C24A 4.5(15) . . . 5_655 ? C16A C17B C22B C17A 114.6(18) . . . . ? C18B C17B C22B C17A 25.9(15) . . . . ? C16B C17B C22B C17A 144.9(18) . . . . ? O2A C17B C22B C17A 167.4(16) . . . . ? C18A C17B C22B C17A 13.2(12) . . . . ? C16A C17B C22B C23A 28(6) . . . 5_655 ? C17A C17B C22B C23A -87(6) . . . 5_655 ? C18B C17B C22B C23A -61(6) . . . 5_655 ? C16B C17B C22B C23A 58(6) . . . 5_655 ? O2A C17B C22B C23A 81(6) . . . 5_655 ? C18A C17B C22B C23A -73(6) . . . 5_655 ? C16A C17B C22B C21B -34.4(16) . . . 5_655 ? C17A C17B C22B C21B -149.0(19) . . . 5_655 ? C18B C17B C22B C21B -123.1(17) . . . 5_655 ? C16B C17B C22B C21B -4.1(19) . . . 5_655 ? O2A C17B C22B C21B 18.4(14) . . . 5_655 ? C18A C17B C22B C21B -135.8(14) . . . 5_655 ? C17A C17B C22B C16A -114.6(18) . . . . ? C18B C17B C22B C16A -88.7(15) . . . . ? C16B C17B C22B C16A 30.3(14) . . . . ? O2A C17B C22B C16A 52.8(11) . . . . ? C18A C17B C22B C16A -101.4(13) . . . . ? C16A C17B C22B C23B 69(3) . . . 5_655 ? C17A C17B C22B C23B -45(3) . . . 5_655 ? C18B C17B C22B C23B -19(3) . . . 5_655 ? C16B C17B C22B C23B 100(3) . . . 5_655 ? O2A C17B C22B C23B 122(3) . . . 5_655 ? C18A C17B C22B C23B -32(3) . . . 5_655 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.69 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.466 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.074 # Attachment 'II-1.cif' data_Cao-6 _database_code_depnum_ccdc_archive 'CCDC 787302' #TrackingRef 'II-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Cyclohexane-1,2,4,5-tetracarboxylic acid:2(Isoquinolin-3(2H)-one),H2O ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H12 O8, 2(C9 H7 N O), H2 O' _chemical_formula_sum 'C28 H28 N2 O11' _chemical_formula_weight 568.52 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 'P 21/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 13.372(3) _cell_length_b 7.1670(10) _cell_length_c 28.248(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.79(3) _cell_angle_gamma 90.00 _cell_volume 2562.9(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15706 _cell_measurement_theta_min 1.61 _cell_measurement_theta_max 25.39 _exptl_crystal_description plate _exptl_crystal_colour red-yellow _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4683 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0736 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.39 _reflns_number_total 4683 _reflns_number_gt 2689 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0849P)^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 4683 _refine_ls_number_parameters 384 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1130 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1428 _refine_ls_wR_factor_gt 0.1242 _refine_ls_goodness_of_fit_ref 0.925 _refine_ls_restrained_S_all 0.929 _refine_ls_shift/su_max 0.003 _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 N1A N 0.13560(18) 0.8740(3) -0.00970(9) 0.0388(6) Uani 1 1 d . . . H1A H 0.0889 0.8694 -0.0389 0.047 Uiso 1 1 calc R . . O1A O 0.01565(15) 0.7370(3) 0.01976(7) 0.0478(5) Uani 1 1 d . . . C1A C 0.1091(2) 0.8037(3) 0.03025(11) 0.0355(7) Uani 1 1 d . . . C2A C 0.1861(2) 0.8130(3) 0.07663(11) 0.0385(7) Uani 1 1 d . . . H2A H 0.1713 0.7664 0.1044 0.046 Uiso 1 1 calc R . . C3A C 0.2854(2) 0.8899(3) 0.08307(11) 0.0362(7) Uani 1 1 d . . . C4A C 0.3660(2) 0.9042(4) 0.12976(11) 0.0441(8) Uani 1 1 d . . . H4A H 0.3539 0.8607 0.1584 0.053 Uiso 1 1 calc R . . C5A C 0.4607(2) 0.9805(4) 0.13323(13) 0.0513(8) Uani 1 1 d . . . H5A H 0.5125 0.9884 0.1644 0.062 Uiso 1 1 calc R . . C6A C 0.4828(2) 1.0478(4) 0.09110(14) 0.0544(9) Uani 1 1 d . . . H6A H 0.5487 1.0988 0.0946 0.065 Uiso 1 1 calc R . . C7A C 0.4085(2) 1.0391(4) 0.04529(13) 0.0472(8) Uani 1 1 d . . . H7A H 0.4233 1.0848 0.0175 0.057 Uiso 1 1 calc R . . C8A C 0.3081(2) 0.9600(3) 0.03988(11) 0.0384(7) Uani 1 1 d . . . C9A C 0.2297(2) 0.9487(3) -0.00552(12) 0.0418(7) Uani 1 1 d . . . H9A H 0.2423 0.9940 -0.0339 0.050 Uiso 1 1 calc R . . N1 N 0.13264(17) 0.2819(3) 0.07403(8) 0.0351(6) Uani 1 1 d . . . H1 H 0.0858 0.2787 0.0448 0.042 Uiso 1 1 calc R . . O1 O 0.01499(14) 0.1268(2) 0.10248(7) 0.0422(5) Uani 1 1 d . . . O2 O 0.12199(16) 0.4435(3) 0.25065(8) 0.0471(6) Uani 1 1 d . . . H2O H 0.124(3) 0.540(4) 0.2407(12) 0.057 Uiso 1 1 d . . . O3 O 0.26804(16) 0.5481(3) 0.30774(8) 0.0536(6) Uani 1 1 d . . . O4 O 0.07162(14) 0.4143(2) 0.35268(7) 0.0402(5) Uani 1 1 d . . . H4O H 0.0267 0.4810 0.3582 0.060 Uiso 1 1 calc R . . O5 O -0.07017(14) 0.2593(2) 0.30632(7) 0.0476(5) Uani 1 1 d . . . O6 O 0.20936(15) 0.1373(3) 0.46279(7) 0.0490(5) Uani 1 1 d . . . O7 O 0.04627(14) 0.0583(3) 0.41604(8) 0.0450(5) Uani 1 1 d . . . H7O H 0.0292 0.1286 0.4350 0.068 Uiso 1 1 calc R . . O8 O 0.44780(15) 0.1393(3) 0.45412(7) 0.0477(5) Uani 1 1 d . . . O9 O 0.38297(16) -0.1400(2) 0.46305(8) 0.0470(6) Uani 1 1 d . . . H9O H 0.437(2) -0.130(4) 0.4905(12) 0.056 Uiso 1 1 d . . . O30 O 0.2834(2) 0.8660(4) 0.24548(12) 0.0914(9) Uani 1 1 d D . . H30A H 0.215(2) 0.854(5) 0.2193(12) 0.110 Uiso 1 1 d D . . H30B H 0.283(3) 0.757(4) 0.2647(14) 0.110 Uiso 1 1 d D . . C1 C 0.1069(2) 0.2036(3) 0.11346(10) 0.0341(6) Uani 1 1 d . . . C2 C 0.1824(2) 0.2151(4) 0.16002(11) 0.0383(7) Uani 1 1 d . . . H2 H 0.1675 0.1672 0.1876 0.046 Uiso 1 1 calc R . . C3 C 0.2812(2) 0.2972(3) 0.16682(10) 0.0354(7) Uani 1 1 d . . . C4 C 0.3628(2) 0.3042(4) 0.21346(11) 0.0455(7) Uani 1 1 d . . . H4 H 0.3510 0.2553 0.2417 0.055 Uiso 1 1 calc R . . C5 C 0.4573(2) 0.3809(4) 0.21753(12) 0.0532(8) Uani 1 1 d . . . H5 H 0.5097 0.3834 0.2486 0.064 Uiso 1 1 calc R . . C6 C 0.4785(2) 0.4571(4) 0.17593(13) 0.0503(8) Uani 1 1 d . . . H6 H 0.5442 0.5099 0.1796 0.060 Uiso 1 1 calc R . . C7 C 0.4034(2) 0.4535(4) 0.13060(11) 0.0417(7) Uani 1 1 d . . . H7 H 0.4176 0.5042 0.1031 0.050 Uiso 1 1 calc R . . C8 C 0.3035(2) 0.3734(3) 0.12442(10) 0.0336(6) Uani 1 1 d . . . C9 C 0.2249(2) 0.3615(3) 0.07833(10) 0.0356(7) Uani 1 1 d . . . H9 H 0.2370 0.4099 0.0501 0.043 Uiso 1 1 calc R . . C10 C 0.2878(2) 0.2261(3) 0.36713(10) 0.0319(6) Uani 1 1 d . . . H10A H 0.3569 0.2656 0.3667 0.038 Uiso 1 1 calc R . . H10B H 0.2652 0.3118 0.3883 0.038 Uiso 1 1 calc R . . C11 C 0.20934(19) 0.2336(3) 0.31391(9) 0.0301(6) Uani 1 1 d . . . H11 H 0.2397 0.1534 0.2940 0.036 Uiso 1 1 calc R . . C12 C 0.09969(19) 0.1495(3) 0.30799(9) 0.0283(6) Uani 1 1 d . . . H12 H 0.0667 0.1238 0.2723 0.034 Uiso 1 1 calc R . . C13 C 0.1102(2) -0.0400(3) 0.33490(9) 0.0307(6) Uani 1 1 d . . . H13A H 0.0410 -0.0773 0.3357 0.037 Uiso 1 1 calc R . . H13B H 0.1331 -0.1324 0.3155 0.037 Uiso 1 1 calc R . . C14 C 0.18700(18) -0.0419(3) 0.38831(9) 0.0287(6) Uani 1 1 d . . . H14 H 0.1962 -0.1727 0.3989 0.034 Uiso 1 1 calc R . . C15 C 0.29575(19) 0.0293(3) 0.38894(9) 0.0297(6) Uani 1 1 d . . . H15 H 0.3180 -0.0519 0.3662 0.036 Uiso 1 1 calc R . . C16 C 0.2043(2) 0.4258(4) 0.29146(10) 0.0335(6) Uani 1 1 d . . . C17 C 0.0257(2) 0.2807(3) 0.32265(10) 0.0310(6) Uani 1 1 d . . . C18 C 0.1488(2) 0.0622(3) 0.42643(10) 0.0306(6) Uani 1 1 d . . . C19 C 0.3816(2) 0.0177(4) 0.43894(10) 0.0344(7) 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 N1A 0.0362(14) 0.0433(13) 0.0350(15) 0.0027(11) 0.0090(11) -0.0014(10) O1A 0.0380(13) 0.0643(13) 0.0391(13) 0.0062(9) 0.0095(10) -0.0118(10) C1A 0.0357(17) 0.0314(14) 0.0400(19) 0.0043(12) 0.0132(15) 0.0017(12) C2A 0.0402(17) 0.0406(15) 0.0332(18) 0.0034(12) 0.0096(15) 0.0028(12) C3A 0.0377(17) 0.0272(14) 0.0441(19) -0.0007(12) 0.0137(15) 0.0068(11) C4A 0.0453(19) 0.0398(16) 0.042(2) -0.0004(13) 0.0063(16) 0.0054(13) C5A 0.045(2) 0.0439(17) 0.057(2) -0.0062(15) 0.0044(17) 0.0072(14) C6A 0.0341(18) 0.0479(18) 0.079(3) -0.0036(17) 0.0156(19) 0.0002(14) C7A 0.0375(18) 0.0429(16) 0.065(2) -0.0008(15) 0.0222(18) -0.0006(13) C8A 0.0395(17) 0.0314(15) 0.045(2) -0.0025(12) 0.0143(16) 0.0044(12) C9A 0.0467(19) 0.0383(15) 0.045(2) 0.0046(13) 0.0217(17) 0.0027(13) N1 0.0326(14) 0.0387(12) 0.0311(14) 0.0025(10) 0.0063(11) 0.0000(10) O1 0.0342(11) 0.0493(11) 0.0401(13) 0.0083(9) 0.0079(10) -0.0061(9) O2 0.0418(12) 0.0490(12) 0.0375(13) 0.0155(10) -0.0054(10) 0.0016(10) O3 0.0412(12) 0.0537(13) 0.0523(15) 0.0185(10) -0.0039(11) -0.0101(10) O4 0.0291(10) 0.0434(11) 0.0469(13) -0.0169(9) 0.0107(10) -0.0009(8) O5 0.0219(11) 0.0594(12) 0.0535(14) -0.0181(10) 0.0009(10) 0.0037(9) O6 0.0387(12) 0.0757(14) 0.0284(12) -0.0164(10) 0.0051(10) -0.0066(10) O7 0.0289(12) 0.0646(13) 0.0448(14) -0.0185(10) 0.0163(10) -0.0057(9) O8 0.0370(12) 0.0518(12) 0.0389(13) 0.0143(9) -0.0092(10) -0.0075(10) O9 0.0427(13) 0.0442(11) 0.0402(13) 0.0170(10) -0.0061(10) -0.0018(9) O30 0.0649(18) 0.0890(19) 0.104(2) 0.0306(16) 0.0040(16) -0.0163(15) C1 0.0340(17) 0.0359(14) 0.0334(18) 0.0044(12) 0.0123(14) 0.0038(12) C2 0.0364(17) 0.0496(16) 0.0314(18) 0.0065(13) 0.0142(14) 0.0038(13) C3 0.0356(16) 0.0387(15) 0.0326(18) 0.0014(12) 0.0119(14) 0.0050(12) C4 0.0415(19) 0.0660(19) 0.0297(18) 0.0011(14) 0.0126(15) 0.0012(15) C5 0.0418(19) 0.075(2) 0.037(2) -0.0066(16) 0.0048(16) -0.0037(16) C6 0.0357(18) 0.0551(18) 0.058(2) -0.0025(16) 0.0116(18) -0.0065(14) C7 0.0415(18) 0.0429(16) 0.041(2) 0.0033(13) 0.0135(16) -0.0001(13) C8 0.0357(16) 0.0319(14) 0.0334(18) -0.0027(12) 0.0113(14) 0.0044(11) C9 0.0409(17) 0.0348(15) 0.0337(18) 0.0022(12) 0.0156(15) 0.0040(12) C10 0.0234(14) 0.0398(15) 0.0301(17) 0.0080(11) 0.0051(12) -0.0010(11) C11 0.0261(15) 0.0390(15) 0.0239(16) 0.0054(11) 0.0061(12) 0.0070(11) C12 0.0242(14) 0.0362(14) 0.0205(15) -0.0029(10) 0.0018(12) 0.0012(11) C13 0.0280(14) 0.0323(14) 0.0299(17) -0.0049(11) 0.0065(13) 0.0004(11) C14 0.0244(14) 0.0317(13) 0.0287(17) 0.0016(11) 0.0067(12) 0.0016(10) C15 0.0256(14) 0.0374(14) 0.0242(16) 0.0037(11) 0.0054(12) 0.0050(11) C16 0.0257(15) 0.0456(16) 0.0283(17) 0.0060(12) 0.0073(13) 0.0067(13) C17 0.0246(16) 0.0367(14) 0.0261(16) -0.0031(12) 0.0005(12) 0.0024(11) C18 0.0290(16) 0.0364(14) 0.0262(17) 0.0046(12) 0.0086(13) -0.0013(11) C19 0.0267(15) 0.0414(16) 0.0333(18) 0.0057(13) 0.0073(13) 0.0042(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 N1A C9A 1.337(3) . ? N1A C1A 1.382(3) . ? N1A H1A 0.8600 . ? O1A C1A 1.281(3) . ? C1A C2A 1.383(4) . ? C2A C3A 1.394(4) . ? C2A H2A 0.9300 . ? C3A C4A 1.413(4) . ? C3A C8A 1.440(4) . ? C4A C5A 1.354(4) . ? C4A H4A 0.9300 . ? C5A C6A 1.401(5) . ? C5A H5A 0.9300 . ? C6A C7A 1.355(4) . ? C6A H6A 0.9300 . ? C7A C8A 1.419(4) . ? C7A H7A 0.9300 . ? C8A C9A 1.373(4) . ? C9A H9A 0.9300 . ? N1 C9 1.329(3) . ? N1 C1 1.386(3) . ? N1 H1 0.8600 . ? O1 C1 1.290(3) . ? O2 C16 1.319(3) . ? O2 H2O 0.75(3) . ? O3 C16 1.206(3) . ? O4 C17 1.295(3) . ? O4 H4O 0.8200 . ? O5 C17 1.225(3) . ? O6 C18 1.210(3) . ? O7 C18 1.306(3) . ? O7 H7O 0.8200 . ? O8 C19 1.218(3) . ? O9 C19 1.316(3) . ? O9 H9O 0.87(3) . ? O30 H30A 0.980(19) . ? O30 H30B 0.952(19) . ? C1 C2 1.379(4) . ? C2 C3 1.402(4) . ? C2 H2 0.9300 . ? C3 C4 1.415(4) . ? C3 C8 1.432(4) . ? C4 C5 1.349(4) . ? C4 H4 0.9300 . ? C5 C6 1.406(4) . ? C5 H5 0.9300 . ? C6 C7 1.349(4) . ? C6 H6 0.9300 . ? C7 C8 1.412(4) . ? C7 H7 0.9300 . ? C8 C9 1.388(4) . ? C9 H9 0.9300 . ? C10 C15 1.529(3) . ? C10 C11 1.532(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C16 1.509(4) . ? C11 C12 1.544(3) . ? C11 H11 0.9800 . ? C12 C17 1.516(3) . ? C12 C13 1.541(3) . ? C12 H12 0.9800 . ? C13 C14 1.527(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.536(3) . ? C14 C18 1.527(4) . ? C14 H14 0.9800 . ? C15 C19 1.508(4) . ? C15 H15 0.9800 . ? 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 C9A N1A C1A 123.7(3) . . ? C9A N1A H1A 118.1 . . ? C1A N1A H1A 118.1 . . ? O1A C1A C2A 127.6(3) . . ? O1A C1A N1A 115.8(3) . . ? C2A C1A N1A 116.6(2) . . ? C1A C2A C3A 122.0(3) . . ? C1A C2A H2A 119.0 . . ? C3A C2A H2A 119.0 . . ? C2A C3A C4A 124.0(3) . . ? C2A C3A C8A 118.7(3) . . ? C4A C3A C8A 117.4(3) . . ? C5A C4A C3A 120.8(3) . . ? C5A C4A H4A 119.6 . . ? C3A C4A H4A 119.6 . . ? C4A C5A C6A 121.7(3) . . ? C4A C5A H5A 119.2 . . ? C6A C5A H5A 119.2 . . ? C7A C6A C5A 120.3(3) . . ? C7A C6A H6A 119.8 . . ? C5A C6A H6A 119.8 . . ? C6A C7A C8A 119.9(3) . . ? C6A C7A H7A 120.1 . . ? C8A C7A H7A 120.1 . . ? C9A C8A C7A 122.4(3) . . ? C9A C8A C3A 117.7(3) . . ? C7A C8A C3A 119.9(3) . . ? N1A C9A C8A 121.3(3) . . ? N1A C9A H9A 119.3 . . ? C8A C9A H9A 119.3 . . ? C9 N1 C1 124.3(2) . . ? C9 N1 H1 117.8 . . ? C1 N1 H1 117.8 . . ? C16 O2 H2O 107(3) . . ? C17 O4 H4O 109.5 . . ? C18 O7 H7O 109.5 . . ? C19 O9 H9O 105(2) . . ? H30A O30 H30B 100(3) . . ? O1 C1 C2 127.1(2) . . ? O1 C1 N1 116.3(2) . . ? C2 C1 N1 116.5(2) . . ? C1 C2 C3 121.6(3) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C2 C3 C4 123.5(3) . . ? C2 C3 C8 119.1(3) . . ? C4 C3 C8 117.3(2) . . ? C5 C4 C3 120.9(3) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 121.5(3) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C7 C6 C5 119.8(3) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C8 120.7(3) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C9 C8 C7 122.8(3) . . ? C9 C8 C3 117.5(2) . . ? C7 C8 C3 119.7(3) . . ? N1 C9 C8 120.8(3) . . ? N1 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C15 C10 C11 111.4(2) . . ? C15 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? C15 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C16 C11 C10 111.6(2) . . ? C16 C11 C12 113.5(2) . . ? C10 C11 C12 114.8(2) . . ? C16 C11 H11 105.3 . . ? C10 C11 H11 105.3 . . ? C12 C11 H11 105.3 . . ? C17 C12 C13 112.1(2) . . ? C17 C12 C11 114.13(19) . . ? C13 C12 C11 110.99(19) . . ? C17 C12 H12 106.3 . . ? C13 C12 H12 106.3 . . ? C11 C12 H12 106.3 . . ? C14 C13 C12 114.87(19) . . ? C14 C13 H13A 108.5 . . ? C12 C13 H13A 108.5 . . ? C14 C13 H13B 108.5 . . ? C12 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? C15 C14 C13 110.0(2) . . ? C15 C14 C18 111.1(2) . . ? C13 C14 C18 114.9(2) . . ? C15 C14 H14 106.8 . . ? C13 C14 H14 106.8 . . ? C18 C14 H14 106.8 . . ? C19 C15 C14 115.1(2) . . ? C19 C15 C10 111.2(2) . . ? C14 C15 C10 111.0(2) . . ? C19 C15 H15 106.3 . . ? C14 C15 H15 106.3 . . ? C10 C15 H15 106.3 . . ? O3 C16 O2 123.5(2) . . ? O3 C16 C11 125.0(2) . . ? O2 C16 C11 111.5(2) . . ? O5 C17 O4 123.9(2) . . ? O5 C17 C12 121.0(2) . . ? O4 C17 C12 115.1(2) . . ? O6 C18 O7 124.5(2) . . ? O6 C18 C14 122.1(2) . . ? O7 C18 C14 113.4(2) . . ? O8 C19 O9 123.0(2) . . ? O8 C19 C15 122.6(2) . . ? O9 C19 C15 114.3(2) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.219 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.048 # Attachment 'III-1.cif' data_Cao-9 _database_code_depnum_ccdc_archive 'CCDC 787303' #TrackingRef 'III-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-benzenediol:Isoquinolin-3(2H)-one ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H13 N O3' _chemical_formula_weight 255.26 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' O O 0.0106 0.0060 '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' _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 5.728(1) _cell_length_b 22.789(4) _cell_length_c 11.111(2) _cell_angle_alpha 90.00 _cell_angle_beta 116.90(3) _cell_angle_gamma 90.00 _cell_volume 1293.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8174 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 26.47 _exptl_crystal_description prism _exptl_crystal_colour red-yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8147 _diffrn_reflns_av_R_equivalents 0.0630 _diffrn_reflns_av_sigmaI/netI 0.0527 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2256 _reflns_number_gt 1341 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1347P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2256 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1014 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1748 _refine_ls_wR_factor_gt 0.1478 _refine_ls_goodness_of_fit_ref 0.847 _refine_ls_restrained_S_all 0.847 _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 -0.1909(4) 0.03875(8) 0.5716(2) 0.0520(6) Uani 1 1 d . . . H1 H -0.3497 0.0422 0.5098 0.062 Uiso 1 1 calc R . . O1 O -0.3007(3) -0.05099(7) 0.62073(17) 0.0600(5) Uani 1 1 d . . . O2 O -0.0814(4) 0.28930(8) 0.9297(2) 0.0746(6) Uani 1 1 d . . . H2O H -0.0253 0.3020 0.8787 0.112 Uiso 1 1 calc R . . O3 O 0.1056(4) 0.15356(7) 1.27787(19) 0.0700(6) Uani 1 1 d . . . H3O H 0.1922 0.1241 1.3122 0.105 Uiso 1 1 calc R . . C1 C -0.1227(5) -0.01183(10) 0.6472(2) 0.0500(6) Uani 1 1 d . . . C2 C 0.1368(5) -0.01497(11) 0.7469(3) 0.0587(7) Uani 1 1 d . . . H2 H 0.1916 -0.0480 0.8020 0.070 Uiso 1 1 calc R . . C3 C 0.3150(5) 0.02953(11) 0.7663(3) 0.0573(7) Uani 1 1 d . . . C4 C 0.5814(6) 0.02698(14) 0.8658(3) 0.0733(9) Uani 1 1 d . . . H4 H 0.6425 -0.0055 0.9221 0.088 Uiso 1 1 calc R . . C5 C 0.7447(6) 0.07155(17) 0.8784(4) 0.0854(10) Uani 1 1 d . . . H5 H 0.9186 0.0689 0.9432 0.103 Uiso 1 1 calc R . . C6 C 0.6631(7) 0.12163(16) 0.7980(4) 0.0832(10) Uani 1 1 d . . . H6 H 0.7810 0.1518 0.8101 0.100 Uiso 1 1 calc R . . C7 C 0.4125(6) 0.12619(14) 0.7026(3) 0.0734(8) Uani 1 1 d . . . H7 H 0.3582 0.1595 0.6485 0.088 Uiso 1 1 calc R . . C8 C 0.2327(5) 0.08086(11) 0.6844(3) 0.0578(7) Uani 1 1 d . . . C9 C -0.0249(5) 0.08296(11) 0.5885(3) 0.0604(7) Uani 1 1 d . . . H9 H -0.0855 0.1160 0.5339 0.073 Uiso 1 1 calc R . . C10 C 0.0688(5) 0.24238(10) 1.0008(2) 0.0520(6) Uani 1 1 d . . . C11 C 0.2546(6) 0.21678(12) 0.9711(3) 0.0642(7) Uani 1 1 d . . . H11 H 0.2872 0.2314 0.9020 0.077 Uiso 1 1 calc R . . C12 C 0.3910(6) 0.16904(12) 1.0463(3) 0.0688(8) Uani 1 1 d . . . H12 H 0.5162 0.1512 1.0269 0.083 Uiso 1 1 calc R . . C13 C 0.3461(5) 0.14719(11) 1.1492(3) 0.0605(7) Uani 1 1 d . . . H13 H 0.4406 0.1151 1.1993 0.073 Uiso 1 1 calc R . . C14 C 0.1604(5) 0.17320(9) 1.1770(2) 0.0502(6) Uani 1 1 d . . . C15 C 0.0196(5) 0.22105(10) 1.1022(3) 0.0516(6) Uani 1 1 d . . . H15 H -0.1072 0.2385 1.1208 0.062 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 N1 0.0455(13) 0.0531(11) 0.0462(12) 0.0073(9) 0.0108(11) 0.0031(9) O1 0.0549(12) 0.0517(10) 0.0552(11) 0.0085(8) 0.0090(9) -0.0016(8) O2 0.0933(16) 0.0636(12) 0.0729(14) 0.0208(9) 0.0429(13) 0.0197(10) O3 0.1020(17) 0.0506(11) 0.0694(13) 0.0114(9) 0.0493(13) 0.0138(9) C1 0.0495(16) 0.0476(13) 0.0455(14) 0.0008(11) 0.0150(13) 0.0027(11) C2 0.0542(17) 0.0574(15) 0.0506(16) 0.0013(12) 0.0113(14) 0.0081(12) C3 0.0481(16) 0.0637(16) 0.0515(16) -0.0126(12) 0.0149(14) 0.0036(12) C4 0.0483(18) 0.083(2) 0.066(2) -0.0125(15) 0.0063(15) 0.0125(15) C5 0.0493(19) 0.109(3) 0.079(2) -0.038(2) 0.0132(17) 0.0004(19) C6 0.064(2) 0.088(2) 0.091(3) -0.0327(19) 0.030(2) -0.0183(17) C7 0.065(2) 0.0715(18) 0.081(2) -0.0131(15) 0.0311(19) -0.0106(15) C8 0.0463(16) 0.0627(16) 0.0574(17) -0.0038(12) 0.0174(14) 0.0002(12) C9 0.0582(17) 0.0538(15) 0.0603(17) 0.0046(12) 0.0189(15) -0.0023(12) C10 0.0573(16) 0.0451(13) 0.0485(15) -0.0015(11) 0.0193(13) -0.0027(11) C11 0.0686(19) 0.0644(16) 0.0661(18) 0.0005(13) 0.0361(16) -0.0069(14) C12 0.0647(18) 0.0692(18) 0.085(2) 0.0010(15) 0.0445(18) 0.0055(14) C13 0.0545(17) 0.0539(14) 0.0669(18) -0.0003(12) 0.0220(15) 0.0056(12) C14 0.0604(16) 0.0404(12) 0.0483(14) -0.0065(10) 0.0232(13) -0.0052(11) C15 0.0557(16) 0.0456(13) 0.0564(16) -0.0012(11) 0.0279(14) 0.0019(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 N1 C9 1.339(3) . ? N1 C1 1.375(3) . ? N1 H1 0.8600 . ? O1 C1 1.285(3) . ? O2 C10 1.376(3) . ? O2 H2O 0.8200 . ? O3 C14 1.369(3) . ? O3 H3O 0.8200 . ? C1 C2 1.397(4) . ? C2 C3 1.385(4) . ? C2 H2 0.9300 . ? C3 C4 1.424(4) . ? C3 C8 1.425(4) . ? C4 C5 1.344(4) . ? C4 H4 0.9300 . ? C5 C6 1.393(5) . ? C5 H5 0.9300 . ? C6 C7 1.348(4) . ? C6 H6 0.9300 . ? C7 C8 1.407(4) . ? C7 H7 0.9300 . ? C8 C9 1.376(4) . ? C9 H9 0.9300 . ? C10 C15 1.369(3) . ? C10 C11 1.378(4) . ? C11 C12 1.379(4) . ? C11 H11 0.9300 . ? C12 C13 1.374(4) . ? C12 H12 0.9300 . ? C13 C14 1.370(4) . ? C13 H13 0.9300 . ? C14 C15 1.387(3) . ? C15 H15 0.9300 . ? 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 N1 C1 123.9(2) . . ? C9 N1 H1 118.1 . . ? C1 N1 H1 118.1 . . ? C10 O2 H2O 109.5 . . ? C14 O3 H3O 109.5 . . ? O1 C1 N1 117.8(2) . . ? O1 C1 C2 126.5(2) . . ? N1 C1 C2 115.7(2) . . ? C3 C2 C1 122.1(2) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C2 C3 C4 123.1(3) . . ? C2 C3 C8 119.6(3) . . ? C4 C3 C8 117.3(3) . . ? C5 C4 C3 120.1(3) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 122.4(3) . . ? C4 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? C7 C6 C5 119.8(3) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C8 120.4(3) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 123.0(3) . . ? C9 C8 C3 116.9(2) . . ? C7 C8 C3 120.1(3) . . ? N1 C9 C8 121.8(2) . . ? N1 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C15 C10 O2 116.1(2) . . ? C15 C10 C11 121.1(2) . . ? O2 C10 C11 122.8(2) . . ? C10 C11 C12 118.5(3) . . ? C10 C11 H11 120.8 . . ? C12 C11 H11 120.8 . . ? C13 C12 C11 121.4(3) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C14 C13 C12 119.2(2) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? O3 C14 C13 122.2(2) . . ? O3 C14 C15 117.4(2) . . ? C13 C14 C15 120.3(2) . . ? C10 C15 C14 119.5(2) . . ? C10 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.232 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.040