Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Christian Wolf' _publ_contact_author_address ; Department of Chemistry University of Georgetown Washington DC-20057 UNITED STATES OF AMERICA ; _publ_contact_author_email CW27@GEORGETOWN.EDU _publ_section_title ; Conformational Polymorphism of 1,8-Dipyridylnaphthalene and Encapsulation of Chains of Fused Cyclic Water Pentamers in a Hydrophobic Crystal Environment ; loop_ _publ_author_name 'Christian Wolf' 'Xuefeng Mei.' # Attachment '04036.CIF' data_g:\data\04036\work\p21onn _database_code_depnum_ccdc_archive 'CCDC 268401' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,8-dipyridylnaphthalene form I ; _chemical_name_common '1,8-dipyridylnaphthalene form I' _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 N2' _chemical_formula_sum 'C20 H14 N2' _chemical_formula_weight 282.33 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.0874(18) _cell_length_b 9.5068(15) _cell_length_c 13.959(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.835(3) _cell_angle_gamma 90.00 _cell_volume 1415.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 359(2) _cell_measurement_reflns_used 797 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 27.17 _exptl_crystal_description prism _exptl_crystal_colour white _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9618 _exptl_absorpt_correction_T_max 0.9922 _exptl_absorpt_process_details 'SADABS, G. Sheldrich (1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 359(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 'SMART platform CCD, Siemens/Bruker' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12278 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.99 _reflns_number_total 3340 _reflns_number_gt 2231 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED, L. Barbour (1999); http:\x-seed.net' _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^)+(0.0539P)^2^+0.1500P] 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 3340 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1189 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.62983(14) 0.82682(15) 0.51075(10) 0.0347(4) Uani 1 1 d . . . N2 N 0.34380(13) 0.92356(17) 0.27217(11) 0.0415(4) Uani 1 1 d . . . C1 C 0.82527(13) 0.88602(15) 0.28602(11) 0.0229(3) Uani 1 1 d . . . C2 C 0.95172(14) 0.91143(16) 0.32236(12) 0.0287(4) Uani 1 1 d . . . H2 H 0.9845 0.9276 0.3902 0.034 Uiso 1 1 calc R . . C3 C 1.03323(15) 0.91396(17) 0.26106(13) 0.0330(4) Uani 1 1 d . . . H3 H 1.1178 0.9347 0.2875 0.040 Uiso 1 1 calc R . . C4 C 0.98669(15) 0.88567(16) 0.16285(12) 0.0298(4) Uani 1 1 d . . . H4 H 1.0413 0.8800 0.1229 0.036 Uiso 1 1 calc R . . C5 C 0.81142(16) 0.84122(17) 0.01574(12) 0.0307(4) Uani 1 1 d . . . H5 H 0.8680 0.8335 -0.0224 0.037 Uiso 1 1 calc R . . C6 C 0.68730(16) 0.82997(17) -0.02888(12) 0.0328(4) Uani 1 1 d . . . H6 H 0.6588 0.8133 -0.0970 0.039 Uiso 1 1 calc R . . C7 C 0.60163(15) 0.84365(16) 0.02826(12) 0.0293(4) Uani 1 1 d . . . H7 H 0.5163 0.8385 -0.0036 0.035 Uiso 1 1 calc R . . C8 C 0.63917(14) 0.86438(15) 0.12977(11) 0.0236(3) Uani 1 1 d . . . C9 C 0.77116(14) 0.87022(15) 0.18041(11) 0.0224(3) Uani 1 1 d . . . C10 C 0.85702(14) 0.86450(15) 0.11961(11) 0.0252(3) Uani 1 1 d . . . C11 C 0.75568(14) 0.86579(16) 0.36249(11) 0.0232(3) Uani 1 1 d . . . C12 C 0.75775(15) 0.96770(17) 0.43474(11) 0.0275(4) Uani 1 1 d . . . H12 H 0.8023 1.0508 0.4355 0.033 Uiso 1 1 calc R . . C13 C 0.69337(16) 0.94478(17) 0.50515(11) 0.0316(4) Uani 1 1 d . . . H13 H 0.6942 1.0155 0.5514 0.038 Uiso 1 1 calc R . . C14 C 0.63175(16) 0.72850(17) 0.44265(13) 0.0338(4) Uani 1 1 d . . . H14 H 0.5898 0.6445 0.4456 0.041 Uiso 1 1 calc R . . C15 C 0.69125(14) 0.74257(16) 0.36857(11) 0.0277(4) Uani 1 1 d . . . H15 H 0.6883 0.6703 0.3231 0.033 Uiso 1 1 calc R . . C16 C 0.53750(14) 0.88681(16) 0.17932(11) 0.0249(3) Uani 1 1 d . . . C17 C 0.53210(14) 1.00487(17) 0.23691(11) 0.0260(4) Uani 1 1 d . . . H17 H 0.5926 1.0749 0.2448 0.031 Uiso 1 1 calc R . . C18 C 0.43643(15) 1.01728(18) 0.28221(12) 0.0330(4) Uani 1 1 d . . . H18 H 0.4364 1.0956 0.3221 0.040 Uiso 1 1 calc R . . C19 C 0.34662(16) 0.8137(2) 0.21319(14) 0.0430(5) Uani 1 1 d . . . H19 H 0.2820 0.7483 0.2031 0.052 Uiso 1 1 calc R . . C20 C 0.43942(15) 0.79140(18) 0.16644(13) 0.0339(4) Uani 1 1 d . . . H20 H 0.4365 0.7127 0.1263 0.041 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 0.0424(9) 0.0367(8) 0.0295(7) 0.0004(6) 0.0177(7) 0.0004(7) N2 0.0245(8) 0.0618(11) 0.0396(8) -0.0145(8) 0.0113(7) -0.0033(7) C1 0.0234(8) 0.0212(8) 0.0250(8) 0.0004(6) 0.0082(6) 0.0018(6) C2 0.0251(9) 0.0334(9) 0.0269(8) -0.0011(7) 0.0059(7) -0.0008(7) C3 0.0212(8) 0.0360(9) 0.0419(10) 0.0005(8) 0.0086(8) -0.0009(7) C4 0.0271(9) 0.0315(9) 0.0359(9) 0.0031(7) 0.0175(7) 0.0032(7) C5 0.0374(10) 0.0324(9) 0.0283(8) 0.0004(7) 0.0192(8) 0.0022(7) C6 0.0427(10) 0.0348(9) 0.0209(8) -0.0012(7) 0.0086(8) 0.0032(8) C7 0.0273(9) 0.0309(9) 0.0274(8) -0.0021(7) 0.0037(7) 0.0030(7) C8 0.0248(8) 0.0213(8) 0.0248(8) -0.0016(6) 0.0070(7) 0.0023(6) C9 0.0255(8) 0.0191(7) 0.0246(8) 0.0012(6) 0.0101(7) 0.0011(6) C10 0.0283(9) 0.0221(8) 0.0282(8) 0.0025(6) 0.0129(7) 0.0037(6) C11 0.0200(8) 0.0280(8) 0.0206(7) 0.0024(6) 0.0037(6) 0.0027(6) C12 0.0271(9) 0.0301(9) 0.0243(8) -0.0021(7) 0.0051(7) -0.0024(7) C13 0.0357(10) 0.0353(10) 0.0242(8) -0.0053(7) 0.0089(7) 0.0017(7) C14 0.0406(10) 0.0282(9) 0.0370(9) -0.0001(7) 0.0182(8) -0.0029(8) C15 0.0321(9) 0.0260(8) 0.0278(8) -0.0006(7) 0.0128(7) 0.0006(7) C16 0.0211(8) 0.0303(8) 0.0217(7) 0.0009(6) 0.0032(6) 0.0028(6) C17 0.0236(8) 0.0278(8) 0.0256(8) 0.0013(7) 0.0051(7) 0.0034(7) C18 0.0275(9) 0.0393(10) 0.0317(9) -0.0075(8) 0.0073(7) 0.0042(7) C19 0.0268(9) 0.0599(13) 0.0438(11) -0.0154(9) 0.0118(8) -0.0152(9) C20 0.0270(9) 0.0408(10) 0.0342(9) -0.0122(8) 0.0087(7) -0.0051(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 N1 C14 1.337(2) . ? N1 C13 1.338(2) . ? N2 C19 1.335(2) . ? N2 C18 1.338(2) . ? C1 C2 1.376(2) . ? C1 C9 1.440(2) . ? C1 C11 1.490(2) . ? C2 C3 1.404(2) . ? C3 C4 1.353(2) . ? C4 C10 1.414(2) . ? C5 C6 1.351(2) . ? C5 C10 1.416(2) . ? C6 C7 1.403(2) . ? C7 C8 1.378(2) . ? C8 C9 1.442(2) . ? C8 C16 1.490(2) . ? C9 C10 1.439(2) . ? C11 C15 1.387(2) . ? C11 C12 1.394(2) . ? C12 C13 1.381(2) . ? C14 C15 1.376(2) . ? C16 C20 1.390(2) . ? C16 C17 1.391(2) . ? C17 C18 1.380(2) . ? C19 C20 1.377(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 C14 N1 C13 115.69(14) . . ? C19 N2 C18 116.04(14) . . ? C2 C1 C9 119.59(13) . . ? C2 C1 C11 115.68(13) . . ? C9 C1 C11 124.56(13) . . ? C1 C2 C3 122.61(15) . . ? C4 C3 C2 118.88(15) . . ? C3 C4 C10 121.54(14) . . ? C6 C5 C10 121.22(15) . . ? C5 C6 C7 119.53(15) . . ? C8 C7 C6 122.45(15) . . ? C7 C8 C9 119.40(14) . . ? C7 C8 C16 116.32(13) . . ? C9 C8 C16 124.20(13) . . ? C10 C9 C1 116.74(13) . . ? C10 C9 C8 117.10(13) . . ? C1 C9 C8 126.12(13) . . ? C4 C10 C5 119.78(14) . . ? C4 C10 C9 120.15(14) . . ? C5 C10 C9 120.06(14) . . ? C15 C11 C12 116.73(14) . . ? C15 C11 C1 121.93(13) . . ? C12 C11 C1 121.25(14) . . ? C13 C12 C11 119.71(15) . . ? N1 C13 C12 123.83(14) . . ? N1 C14 C15 124.74(16) . . ? C14 C15 C11 119.25(15) . . ? C20 C16 C17 116.48(14) . . ? C20 C16 C8 120.73(14) . . ? C17 C16 C8 122.75(14) . . ? C18 C17 C16 119.56(15) . . ? N2 C18 C17 123.99(15) . . ? N2 C19 C20 123.98(16) . . ? C19 C20 C16 119.85(15) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.232 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.045 #==END # Attachment '04105.CIF' data_d:\xuefeng\x-ray\04105\work\sad _database_code_depnum_ccdc_archive 'CCDC 268402' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,8-dipyridylnaphthalene-form II ; _chemical_name_common '1,8-dipyridylnaphthalene-form II' _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 N2' _chemical_formula_sum 'C20 H14 N2' _chemical_formula_weight 282.33 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' _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 8.2970(15) _cell_length_b 9.4627(17) _cell_length_c 10.3160(18) _cell_angle_alpha 79.870(3) _cell_angle_beta 73.067(3) _cell_angle_gamma 65.092(3) _cell_volume 701.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 957 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 28.18 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9614 _exptl_absorpt_correction_T_max 0.9843 _exptl_absorpt_process_details 'SADABS, G. Sheldrich (1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'SMART platform CCD, Siemens/Bruker' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5647 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2723 _reflns_number_gt 2273 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED, L. Barbour (1999); http:\x-seed.net' _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^)+(0.0497P)^2^+0.2535P] 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 2723 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1109 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.1834(2) 0.14634(17) 0.89028(13) 0.0373(4) Uani 1 1 d . . . N2 N -0.3536(2) 0.28126(17) 0.93265(13) 0.0391(4) Uani 1 1 d . . . C1 C 0.17311(19) 0.21058(16) 0.46920(14) 0.0217(3) Uani 1 1 d . . . C2 C 0.3426(2) 0.18387(17) 0.38101(15) 0.0261(3) Uani 1 1 d . . . H2 H 0.4456 0.1552 0.4175 0.031 Uiso 1 1 calc R . . C3 C 0.3685(2) 0.19740(18) 0.23977(15) 0.0283(3) Uani 1 1 d . . . H3 H 0.4871 0.1781 0.1819 0.034 Uiso 1 1 calc R . . C4 C 0.2220(2) 0.23852(18) 0.18654(14) 0.0282(3) Uani 1 1 d . . . H4 H 0.2393 0.2469 0.0908 0.034 Uiso 1 1 calc R . . C5 C -0.1046(2) 0.31175(18) 0.21071(15) 0.0294(3) Uani 1 1 d . . . H5 H -0.0831 0.3201 0.1146 0.035 Uiso 1 1 calc R . . C6 C -0.2770(2) 0.34081(18) 0.28836(16) 0.0324(4) Uani 1 1 d . . . H6 H -0.3757 0.3694 0.2469 0.039 Uiso 1 1 calc R . . C7 C -0.3084(2) 0.32825(18) 0.43010(16) 0.0291(3) Uani 1 1 d . . . H7 H -0.4294 0.3474 0.4833 0.035 Uiso 1 1 calc R . . C8 C -0.1706(2) 0.28923(16) 0.49573(14) 0.0238(3) Uani 1 1 d . . . C9 C 0.01428(19) 0.25624(16) 0.41645(14) 0.0220(3) Uani 1 1 d . . . C10 C 0.0439(2) 0.26906(16) 0.27121(14) 0.0241(3) Uani 1 1 d . . . C11 C 0.17109(18) 0.18891(17) 0.61656(14) 0.0227(3) Uani 1 1 d . . . C12 C 0.2103(2) 0.28957(18) 0.67410(15) 0.0282(3) Uani 1 1 d . . . H12 H 0.2340 0.3748 0.6212 0.034 Uiso 1 1 calc R . . C13 C 0.2144(2) 0.2636(2) 0.80942(16) 0.0344(4) Uani 1 1 d . . . H13 H 0.2408 0.3336 0.8473 0.041 Uiso 1 1 calc R . . C14 C 0.1487(2) 0.04911(19) 0.83370(15) 0.0328(4) Uani 1 1 d . . . H14 H 0.1278 -0.0361 0.8889 0.039 Uiso 1 1 calc R . . C15 C 0.1414(2) 0.06509(17) 0.69935(14) 0.0260(3) Uani 1 1 d . . . H15 H 0.1163 -0.0077 0.6641 0.031 Uiso 1 1 calc R . . C16 C -0.22963(18) 0.28616(16) 0.64738(15) 0.0240(3) Uani 1 1 d . . . C17 C -0.2328(2) 0.39745(17) 0.72096(15) 0.0277(3) Uani 1 1 d . . . H17 H -0.1922 0.4774 0.6757 0.033 Uiso 1 1 calc R . . C18 C -0.2955(2) 0.39068(19) 0.86065(16) 0.0341(4) Uani 1 1 d . . . H18 H -0.2977 0.4686 0.9087 0.041 Uiso 1 1 calc R . . C19 C -0.2944(2) 0.17464(19) 0.72046(16) 0.0317(4) Uani 1 1 d . . . H19 H -0.2992 0.0982 0.6747 0.038 Uiso 1 1 calc R . . C22 C -0.3520(2) 0.1762(2) 0.86068(17) 0.0376(4) Uani 1 1 d . . . H22 H -0.3930 0.0975 0.9087 0.045 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 0.0468(9) 0.0408(8) 0.0238(7) -0.0017(6) -0.0123(6) -0.0144(7) N2 0.0403(8) 0.0405(8) 0.0279(7) -0.0031(6) 0.0029(6) -0.0148(7) C1 0.0255(7) 0.0187(7) 0.0210(7) -0.0009(5) -0.0045(6) -0.0095(6) C2 0.0246(8) 0.0292(8) 0.0262(8) -0.0021(6) -0.0058(6) -0.0122(6) C3 0.0281(8) 0.0322(8) 0.0237(7) -0.0048(6) 0.0020(6) -0.0150(7) C4 0.0381(9) 0.0303(8) 0.0163(7) -0.0019(6) -0.0028(6) -0.0158(7) C5 0.0391(9) 0.0287(8) 0.0238(7) 0.0001(6) -0.0128(6) -0.0138(7) C6 0.0346(9) 0.0299(8) 0.0379(9) 0.0000(7) -0.0200(7) -0.0111(7) C7 0.0231(7) 0.0261(8) 0.0381(9) -0.0052(7) -0.0070(6) -0.0087(6) C8 0.0259(7) 0.0190(7) 0.0260(7) -0.0023(6) -0.0046(6) -0.0089(6) C9 0.0256(7) 0.0190(7) 0.0223(7) -0.0014(6) -0.0053(6) -0.0100(6) C10 0.0311(8) 0.0209(7) 0.0213(7) -0.0011(6) -0.0069(6) -0.0108(6) C11 0.0178(7) 0.0262(8) 0.0208(7) -0.0034(6) -0.0041(5) -0.0053(6) C12 0.0298(8) 0.0314(8) 0.0263(8) -0.0010(6) -0.0079(6) -0.0144(7) C13 0.0404(9) 0.0382(9) 0.0300(8) -0.0058(7) -0.0128(7) -0.0164(8) C14 0.0381(9) 0.0301(9) 0.0238(8) 0.0026(6) -0.0060(6) -0.0100(7) C15 0.0261(8) 0.0236(7) 0.0253(8) -0.0026(6) -0.0049(6) -0.0073(6) C16 0.0165(7) 0.0235(8) 0.0273(8) -0.0030(6) -0.0020(6) -0.0050(6) C17 0.0270(8) 0.0238(8) 0.0280(8) -0.0019(6) -0.0027(6) -0.0085(6) C18 0.0358(9) 0.0308(9) 0.0300(8) -0.0077(7) -0.0020(7) -0.0094(7) C19 0.0311(8) 0.0318(9) 0.0331(8) -0.0038(7) -0.0017(7) -0.0165(7) C22 0.0374(9) 0.0390(10) 0.0332(9) 0.0020(7) 0.0015(7) -0.0205(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 N1 C14 1.334(2) . ? N1 C13 1.335(2) . ? N2 C22 1.335(2) . ? N2 C18 1.340(2) . ? C1 C2 1.380(2) . ? C1 C9 1.440(2) . ? C1 C11 1.4939(19) . ? C2 C3 1.400(2) . ? C3 C4 1.359(2) . ? C4 C10 1.417(2) . ? C5 C6 1.358(2) . ? C5 C10 1.418(2) . ? C6 C7 1.401(2) . ? C7 C8 1.382(2) . ? C8 C9 1.441(2) . ? C8 C16 1.496(2) . ? C9 C10 1.4377(19) . ? C11 C15 1.390(2) . ? C11 C12 1.392(2) . ? C12 C13 1.382(2) . ? C14 C15 1.384(2) . ? C16 C19 1.390(2) . ? C16 C17 1.390(2) . ? C17 C18 1.382(2) . ? C19 C22 1.386(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 C14 N1 C13 116.50(13) . . ? C22 N2 C18 115.82(14) . . ? C2 C1 C9 119.86(13) . . ? C2 C1 C11 115.32(12) . . ? C9 C1 C11 124.81(12) . . ? C1 C2 C3 122.52(14) . . ? C4 C3 C2 119.17(13) . . ? C3 C4 C10 121.23(13) . . ? C6 C5 C10 120.85(14) . . ? C5 C6 C7 119.49(14) . . ? C8 C7 C6 122.71(14) . . ? C7 C8 C9 119.25(13) . . ? C7 C8 C16 115.56(13) . . ? C9 C8 C16 125.19(12) . . ? C10 C9 C1 116.74(12) . . ? C10 C9 C8 117.22(12) . . ? C1 C9 C8 126.03(13) . . ? C4 C10 C5 119.07(13) . . ? C4 C10 C9 120.46(13) . . ? C5 C10 C9 120.46(13) . . ? C15 C11 C12 117.38(13) . . ? C15 C11 C1 122.48(13) . . ? C12 C11 C1 120.04(13) . . ? C13 C12 C11 118.96(14) . . ? N1 C13 C12 124.11(15) . . ? N1 C14 C15 123.83(15) . . ? C14 C15 C11 119.22(14) . . ? C19 C16 C17 117.01(14) . . ? C19 C16 C8 120.35(13) . . ? C17 C16 C8 122.54(13) . . ? C18 C17 C16 119.36(14) . . ? N2 C18 C17 124.22(15) . . ? C22 C19 C16 119.30(15) . . ? N2 C22 C19 124.25(15) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.214 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.035 # Attachment 'P21ONN.CIF' data_d:\xuefeng\x-ray\04186\work\p21onn _database_code_depnum_ccdc_archive 'CCDC 268403' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,8-dipyridylnaphthalene-3H2O ; _chemical_name_common 1,8-dipyridylnaphthalene-3H2O _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 N2 O3' _chemical_formula_sum 'C20 H20 N2 O3' _chemical_formula_weight 336.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.356(3) _cell_length_b 6.9200(15) _cell_length_c 19.596(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.203(4) _cell_angle_gamma 90.00 _cell_volume 1739.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 187(2) _cell_measurement_reflns_used 913 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 27.07 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9577 _exptl_absorpt_correction_T_max 0.9983 _exptl_absorpt_process_details 'SADABS, G. Sheldrich (1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 187(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 'SMART platform CCD Siemens/Bruker' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14874 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.99 _reflns_number_total 4065 _reflns_number_gt 2483 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED, L. Barbour (1999); http:\x-seed.net' _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^)+(0.0766P)^2^+0.0134P] 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 4065 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1007 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1226 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.34022(11) 0.0910(2) -0.18278(8) 0.0422(4) Uani 1 1 d . . . O2 O 0.35666(13) 0.4566(2) -0.23965(9) 0.0499(4) Uani 1 1 d . . . O3 O 0.45603(11) 0.7492(2) -0.14900(8) 0.0426(4) Uani 1 1 d . . . N1 N 0.27248(12) 0.1694(2) -0.06298(8) 0.0340(4) Uani 1 1 d . . . N2 N 0.39425(13) 0.6942(2) -0.02253(9) 0.0383(4) Uani 1 1 d . . . C1 C 0.11909(13) 0.3466(2) 0.09300(9) 0.0260(4) Uani 1 1 d . . . C2 C 0.04683(14) 0.2175(3) 0.10403(10) 0.0340(5) Uani 1 1 d . . . C3 C -0.00752(15) 0.2477(3) 0.15484(11) 0.0386(5) Uani 1 1 d . . . C4 C 0.01002(14) 0.4115(3) 0.19414(10) 0.0360(5) Uani 1 1 d . . . C5 C 0.09747(15) 0.7229(3) 0.22678(10) 0.0356(5) Uani 1 1 d . . . C6 C 0.16692(15) 0.8589(3) 0.22031(10) 0.0367(5) Uani 1 1 d . . . C7 C 0.22327(15) 0.8333(3) 0.17013(10) 0.0325(4) Uani 1 1 d . . . C8 C 0.20935(13) 0.6747(2) 0.12602(9) 0.0258(4) Uani 1 1 d . . . C9 C 0.13798(12) 0.5238(2) 0.13272(9) 0.0236(4) Uani 1 1 d . . . C10 C 0.08178(13) 0.5527(3) 0.18444(9) 0.0290(4) Uani 1 1 d . . . C11 C 0.17382(13) 0.2864(2) 0.03977(9) 0.0247(4) Uani 1 1 d . . . C12 C 0.27955(14) 0.2414(2) 0.05818(10) 0.0264(4) Uani 1 1 d . . . C13 C 0.32473(15) 0.1848(3) 0.00603(10) 0.0302(4) Uani 1 1 d . . . C14 C 0.17002(16) 0.2075(3) -0.08033(10) 0.0336(4) Uani 1 1 d . . . C15 C 0.11800(14) 0.2628(3) -0.03190(10) 0.0310(4) Uani 1 1 d . . . C16 C 0.27239(13) 0.6768(2) 0.07394(9) 0.0268(4) Uani 1 1 d . . . C17 C 0.38122(14) 0.6799(3) 0.09729(10) 0.0332(4) Uani 1 1 d . . . C18 C 0.43825(16) 0.6878(3) 0.04838(11) 0.0371(5) Uani 1 1 d . . . C19 C 0.28921(16) 0.6955(3) -0.04466(11) 0.0354(5) Uani 1 1 d . . . C20 C 0.22662(15) 0.6880(3) 0.00087(10) 0.0309(4) Uani 1 1 d . . . H13 H 0.3964(14) 0.151(2) 0.0186(9) 0.022(4) Uiso 1 1 d . . . H12 H 0.3205(15) 0.255(3) 0.1068(11) 0.034(5) Uiso 1 1 d . . . H5 H 0.0558(17) 0.742(3) 0.2595(12) 0.052(6) Uiso 1 1 d . . . H20 H 0.1445(15) 0.692(3) -0.0197(10) 0.036(5) Uiso 1 1 d . . . H7 H 0.2748(15) 0.944(3) 0.1657(11) 0.047(6) Uiso 1 1 d . . . H15 H 0.0394(16) 0.293(3) -0.0491(10) 0.040(5) Uiso 1 1 d . . . H17 H 0.4219(16) 0.668(3) 0.1508(12) 0.048(6) Uiso 1 1 d . . . H6 H 0.1770(15) 0.975(3) 0.2493(11) 0.046(6) Uiso 1 1 d . . . H2 H 0.0393(14) 0.097(3) 0.0774(11) 0.041(5) Uiso 1 1 d . . . H19 H 0.2646(16) 0.687(3) -0.1046(12) 0.054(6) Uiso 1 1 d . . . H14 H 0.1320(15) 0.203(3) -0.1297(11) 0.036(5) Uiso 1 1 d . . . H3 H -0.0567(16) 0.154(3) 0.1623(11) 0.042(6) Uiso 1 1 d . . . H4 H -0.0239(17) 0.439(3) 0.2289(12) 0.057(7) Uiso 1 1 d . . . H18 H 0.5216(18) 0.683(3) 0.0647(12) 0.055(6) Uiso 1 1 d . . . H1 H 0.4363(18) 0.721(4) -0.1035(14) 0.063(7) Uiso 1 1 d . . . H8 H 0.324(2) 0.119(4) -0.1415(16) 0.088(10) Uiso 1 1 d . . . H10 H 0.398(3) 0.605(5) -0.1903(18) 0.132(12) Uiso 1 1 d . . . H16 H 0.409(3) 0.887(6) -0.167(2) 0.164(16) Uiso 1 1 d . . . H9 H 0.344(3) 0.299(8) -0.205(2) 0.187(19) Uiso 1 1 d . . . H11 H 0.287(3) 0.505(6) -0.257(2) 0.160(17) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0502(9) 0.0436(9) 0.0369(8) -0.0026(7) 0.0188(7) 0.0056(7) O2 0.0525(10) 0.0476(9) 0.0511(9) 0.0022(8) 0.0167(8) 0.0050(8) O3 0.0422(8) 0.0502(9) 0.0413(9) 0.0056(7) 0.0212(7) 0.0040(7) N1 0.0416(9) 0.0286(8) 0.0347(9) -0.0037(7) 0.0156(7) -0.0008(7) N2 0.0392(10) 0.0380(9) 0.0420(10) 0.0014(8) 0.0187(8) -0.0013(7) C1 0.0224(9) 0.0296(10) 0.0255(9) 0.0031(7) 0.0061(7) 0.0024(7) C2 0.0309(10) 0.0343(11) 0.0379(11) 0.0009(9) 0.0113(9) -0.0026(8) C3 0.0288(10) 0.0469(12) 0.0426(12) 0.0069(10) 0.0140(9) -0.0053(9) C4 0.0286(10) 0.0526(13) 0.0300(11) 0.0068(9) 0.0137(8) 0.0016(9) C5 0.0359(11) 0.0489(12) 0.0242(10) -0.0033(8) 0.0120(8) 0.0095(9) C6 0.0394(11) 0.0387(12) 0.0309(11) -0.0094(9) 0.0078(9) 0.0041(9) C7 0.0355(10) 0.0317(10) 0.0300(10) -0.0011(8) 0.0089(8) 0.0003(8) C8 0.0248(9) 0.0279(9) 0.0248(9) 0.0026(7) 0.0069(7) 0.0015(7) C9 0.0182(8) 0.0307(9) 0.0203(8) 0.0035(7) 0.0028(7) 0.0033(7) C10 0.0233(9) 0.0402(11) 0.0233(9) 0.0044(8) 0.0064(7) 0.0063(8) C11 0.0285(9) 0.0180(8) 0.0283(9) -0.0012(7) 0.0089(7) -0.0016(7) C12 0.0288(9) 0.0228(9) 0.0273(10) 0.0021(7) 0.0075(8) 0.0007(7) C13 0.0300(10) 0.0256(9) 0.0373(11) 0.0004(8) 0.0132(9) 0.0026(8) C14 0.0403(11) 0.0315(10) 0.0269(10) -0.0039(8) 0.0061(9) -0.0019(8) C15 0.0286(10) 0.0315(10) 0.0309(10) -0.0019(8) 0.0050(8) -0.0004(8) C16 0.0312(10) 0.0201(8) 0.0312(10) 0.0011(7) 0.0123(8) -0.0015(7) C17 0.0313(10) 0.0340(10) 0.0341(11) 0.0019(8) 0.0088(9) -0.0019(8) C18 0.0334(11) 0.0403(11) 0.0398(12) 0.0006(9) 0.0140(9) -0.0029(9) C19 0.0416(11) 0.0332(10) 0.0335(11) 0.0019(8) 0.0142(9) -0.0001(8) C20 0.0325(10) 0.0275(10) 0.0323(10) 0.0035(8) 0.0083(8) -0.0008(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 N1 C14 1.341(2) . ? N1 C13 1.342(2) . ? N2 C19 1.348(3) . ? N2 C18 1.350(3) . ? C1 C2 1.376(3) . ? C1 C9 1.436(2) . ? C1 C11 1.491(2) . ? C2 C3 1.402(3) . ? C3 C4 1.353(3) . ? C4 C10 1.418(3) . ? C5 C6 1.352(3) . ? C5 C10 1.422(3) . ? C6 C7 1.406(3) . ? C7 C8 1.377(2) . ? C8 C9 1.445(2) . ? C8 C16 1.493(2) . ? C9 C10 1.434(2) . ? C11 C12 1.392(2) . ? C11 C15 1.404(2) . ? C12 C13 1.381(2) . ? C14 C15 1.377(3) . ? C16 C20 1.393(2) . ? C16 C17 1.397(3) . ? C17 C18 1.382(3) . ? C19 C20 1.383(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 N1 C13 116.55(16) . . ? C19 N2 C18 116.52(17) . . ? C2 C1 C9 119.61(16) . . ? C2 C1 C11 115.53(16) . . ? C9 C1 C11 124.86(15) . . ? C1 C2 C3 122.65(19) . . ? C4 C3 C2 119.17(19) . . ? C3 C4 C10 121.12(19) . . ? C6 C5 C10 121.01(18) . . ? C5 C6 C7 119.54(19) . . ? C8 C7 C6 122.30(18) . . ? C7 C8 C9 119.74(16) . . ? C7 C8 C16 114.71(16) . . ? C9 C8 C16 125.55(15) . . ? C10 C9 C1 117.06(15) . . ? C10 C9 C8 116.89(15) . . ? C1 C9 C8 126.05(15) . . ? C4 C10 C5 119.18(17) . . ? C4 C10 C9 120.35(17) . . ? C5 C10 C9 120.46(17) . . ? C12 C11 C15 116.77(16) . . ? C12 C11 C1 122.78(15) . . ? C15 C11 C1 120.36(15) . . ? C13 C12 C11 119.54(17) . . ? N1 C13 C12 123.83(18) . . ? N1 C14 C15 123.72(18) . . ? C14 C15 C11 119.50(17) . . ? C20 C16 C17 116.98(16) . . ? C20 C16 C8 122.24(16) . . ? C17 C16 C8 120.66(16) . . ? C18 C17 C16 119.87(18) . . ? N2 C18 C17 123.32(18) . . ? N2 C19 C20 123.66(18) . . ? C19 C20 C16 119.61(18) . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.230 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.049 #===END