# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Xiaodong Shi' _publ_contact_author_email XIAODONG.SHI@MAIL.WVU.EDU _publ_section_title ; Conformational Control for the Regioselective Synthesis of N- 2-Substituted-1,2,3-Triazoles ; loop_ _publ_author_name 'Xiaodong Shi.' 'Yunfeng Chen.' 'Yu-Xiu Liu.' 'Jeffrey Petersen' # Attachment 'Structure3.CIF' data_N-1-3a _database_code_depnum_ccdc_archive 'CCDC 682966' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H19 N3' _chemical_formula_weight 337.41 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 9.6394(9) _cell_length_b 10.7499(10) _cell_length_c 10.9959(9) _cell_angle_alpha 62.390(1) _cell_angle_beta 68.503(2) _cell_angle_gamma 68.570(2) _cell_volume 912.63(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3837 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 27.47 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.971 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details SADABS _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_% none _diffrn_reflns_number 6310 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0678 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4000 _reflns_number_gt 2986 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0840P)^2^+0.0801P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4000 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_ref 0.1707 _refine_ls_wR_factor_gt 0.1543 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.39847(15) -0.07336(14) 0.23415(12) 0.0459(3) Uani 1 1 d . . . N2 N 0.53384(16) -0.16394(15) 0.20573(13) 0.0494(3) Uani 1 1 d . . . N3 N 0.63567(15) -0.08628(14) 0.12921(12) 0.0461(3) Uani 1 1 d . . . C1 C 0.41205(17) 0.06517(16) 0.17470(14) 0.0428(3) Uani 1 1 d . . . C2 C 0.56488(17) 0.05574(16) 0.10728(14) 0.0422(3) Uani 1 1 d . . . C3 C 0.28038(17) 0.18616(17) 0.19568(15) 0.0464(4) Uani 1 1 d . . . C4 C 0.1911(2) 0.2592(2) 0.10588(19) 0.0679(5) Uani 1 1 d . . . H4A H 0.2105 0.2352 0.0292 0.082 Uiso 1 1 calc R . . H4B H 0.1089 0.3348 0.1193 0.082 Uiso 1 1 calc R . . C5 C 0.25630(17) 0.21599(16) 0.32261(14) 0.0425(3) Uani 1 1 d . . . C6 C 0.3789(2) 0.1827(2) 0.37903(17) 0.0542(4) Uani 1 1 d . . . H6 H 0.4769 0.1411 0.3376 0.065 Uiso 1 1 calc R . . C7 C 0.3561(2) 0.2110(2) 0.4968(2) 0.0689(5) Uani 1 1 d . . . H7 H 0.4391 0.1903 0.5326 0.083 Uiso 1 1 calc R . . C8 C 0.2114(3) 0.2696(2) 0.5607(2) 0.0702(5) Uani 1 1 d . . . H8 H 0.1963 0.2875 0.6402 0.084 Uiso 1 1 calc R . . C9 C 0.0886(2) 0.3018(2) 0.50664(19) 0.0621(5) Uani 1 1 d . . . H9 H -0.0095 0.3413 0.5499 0.075 Uiso 1 1 calc R . . C10 C 0.11088(19) 0.27548(18) 0.38823(17) 0.0499(4) Uani 1 1 d . . . H10 H 0.0275 0.2979 0.3522 0.060 Uiso 1 1 calc R . . C11 C 0.2614(2) -0.1310(2) 0.31686(16) 0.0553(4) Uani 1 1 d . . . H11A H 0.2548 -0.1922 0.2774 0.066 Uiso 1 1 calc R . . H11B H 0.1709 -0.0514 0.3093 0.066 Uiso 1 1 calc R . . C12 C 0.26254(18) -0.21699(19) 0.47058(16) 0.0494(4) Uani 1 1 d . . . C13 C 0.2146(2) -0.1471(2) 0.56315(18) 0.0631(5) Uani 1 1 d . . . H13 H 0.1810 -0.0469 0.5302 0.076 Uiso 1 1 calc R . . C14 C 0.2163(3) -0.2254(3) 0.7038(2) 0.0804(7) Uani 1 1 d . . . H14 H 0.1841 -0.1779 0.7653 0.097 Uiso 1 1 calc R . . C15 C 0.2655(3) -0.3730(3) 0.7529(2) 0.0888(8) Uani 1 1 d . . . H15 H 0.2663 -0.4255 0.8479 0.107 Uiso 1 1 calc R . . C16 C 0.3129(3) -0.4428(3) 0.6639(2) 0.0867(7) Uani 1 1 d . . . H16 H 0.3466 -0.5429 0.6977 0.104 Uiso 1 1 calc R . . C17 C 0.3112(2) -0.3646(2) 0.5213(2) 0.0657(5) Uani 1 1 d . . . H17 H 0.3434 -0.4129 0.4606 0.079 Uiso 1 1 calc R . . C18 C 0.65341(18) 0.16727(17) 0.02240(14) 0.0454(4) Uani 1 1 d . . . C19 C 0.8107(2) 0.1303(2) 0.0058(2) 0.0613(5) Uani 1 1 d . . . H19 H 0.8592 0.0350 0.0512 0.074 Uiso 1 1 calc R . . C20 C 0.8973(3) 0.2328(2) -0.0775(2) 0.0755(6) Uani 1 1 d . . . H20 H 1.0030 0.2058 -0.0874 0.091 Uiso 1 1 calc R . . C21 C 0.8280(3) 0.3722(2) -0.1445(2) 0.0758(6) Uani 1 1 d . . . H21 H 0.8861 0.4408 -0.2008 0.091 Uiso 1 1 calc R . . C22 C 0.6725(3) 0.4118(2) -0.1289(2) 0.0794(6) Uani 1 1 d . . . H22 H 0.6254 0.5076 -0.1745 0.095 Uiso 1 1 calc R . . C23 C 0.5843(2) 0.3109(2) -0.0459(2) 0.0663(5) Uani 1 1 d . . . H23 H 0.4786 0.3394 -0.0359 0.080 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 0.0457(7) 0.0512(8) 0.0406(6) -0.0187(5) -0.0066(5) -0.0132(6) N2 0.0513(8) 0.0474(7) 0.0469(6) -0.0183(6) -0.0080(6) -0.0123(6) N3 0.0467(7) 0.0466(7) 0.0431(6) -0.0192(5) -0.0074(5) -0.0095(6) C1 0.0441(8) 0.0491(8) 0.0375(6) -0.0193(6) -0.0088(6) -0.0107(6) C2 0.0430(8) 0.0451(8) 0.0380(6) -0.0190(6) -0.0078(6) -0.0074(6) C3 0.0405(8) 0.0534(9) 0.0453(7) -0.0233(7) -0.0070(6) -0.0085(7) C4 0.0571(11) 0.0857(14) 0.0608(10) -0.0411(10) -0.0215(8) 0.0083(10) C5 0.0425(8) 0.0417(8) 0.0435(7) -0.0177(6) -0.0064(6) -0.0122(6) C6 0.0455(9) 0.0651(11) 0.0556(8) -0.0306(8) -0.0110(7) -0.0081(7) C7 0.0593(11) 0.0959(15) 0.0699(11) -0.0459(11) -0.0197(9) -0.0147(10) C8 0.0719(13) 0.0918(15) 0.0644(10) -0.0487(11) -0.0096(9) -0.0196(11) C9 0.0526(10) 0.0745(12) 0.0638(10) -0.0426(9) -0.0003(8) -0.0118(9) C10 0.0438(8) 0.0538(9) 0.0545(8) -0.0258(7) -0.0063(7) -0.0125(7) C11 0.0518(9) 0.0678(11) 0.0499(8) -0.0192(8) -0.0091(7) -0.0253(8) C12 0.0392(8) 0.0612(10) 0.0480(8) -0.0199(7) -0.0039(6) -0.0197(7) C13 0.0694(12) 0.0701(12) 0.0561(9) -0.0264(9) -0.0031(8) -0.0320(10) C14 0.0837(15) 0.115(2) 0.0550(10) -0.0366(12) -0.0025(10) -0.0461(14) C15 0.0716(14) 0.119(2) 0.0526(10) -0.0100(13) -0.0146(10) -0.0285(14) C16 0.0617(13) 0.0709(14) 0.0804(14) -0.0013(12) -0.0140(11) -0.0052(10) C17 0.0511(10) 0.0631(12) 0.0698(11) -0.0261(9) -0.0031(8) -0.0100(9) C18 0.0486(9) 0.0468(8) 0.0402(7) -0.0193(6) -0.0059(6) -0.0118(7) C19 0.0487(10) 0.0538(10) 0.0690(10) -0.0196(8) -0.0052(8) -0.0132(8) C20 0.0558(11) 0.0731(14) 0.0885(14) -0.0303(11) 0.0016(10) -0.0252(10) C21 0.0846(15) 0.0648(13) 0.0739(12) -0.0263(10) 0.0064(11) -0.0388(11) C22 0.0892(17) 0.0490(11) 0.0809(13) -0.0116(10) -0.0126(12) -0.0213(10) C23 0.0618(12) 0.0498(10) 0.0748(11) -0.0174(9) -0.0147(9) -0.0097(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 N2 1.3429(18) . ? N1 C1 1.356(2) . ? N1 C11 1.467(2) . ? N2 N3 1.3079(19) . ? N3 C2 1.3685(19) . ? C1 C2 1.375(2) . ? C1 C3 1.488(2) . ? C2 C18 1.471(2) . ? C3 C4 1.320(2) . ? C3 C5 1.4926(19) . ? C5 C10 1.388(2) . ? C5 C6 1.390(2) . ? C6 C7 1.388(2) . ? C7 C8 1.373(3) . ? C8 C9 1.378(3) . ? C9 C10 1.383(2) . ? C11 C12 1.507(2) . ? C12 C17 1.370(3) . ? C12 C13 1.387(2) . ? C13 C14 1.379(3) . ? C14 C15 1.371(4) . ? C15 C16 1.354(4) . ? C16 C17 1.397(3) . ? C18 C19 1.383(2) . ? C18 C23 1.390(2) . ? C19 C20 1.388(3) . ? C20 C21 1.357(3) . ? C21 C22 1.368(3) . ? C22 C23 1.385(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 N2 N1 C1 111.24(13) . . ? N2 N1 C11 119.33(14) . . ? C1 N1 C11 129.40(14) . . ? N3 N2 N1 107.35(13) . . ? N2 N3 C2 108.97(13) . . ? N1 C1 C2 104.08(13) . . ? N1 C1 C3 122.08(14) . . ? C2 C1 C3 133.74(15) . . ? N3 C2 C1 108.35(14) . . ? N3 C2 C18 120.25(14) . . ? C1 C2 C18 131.40(14) . . ? C4 C3 C1 120.21(13) . . ? C4 C3 C5 123.55(14) . . ? C1 C3 C5 116.23(12) . . ? C10 C5 C6 118.51(13) . . ? C10 C5 C3 120.83(13) . . ? C6 C5 C3 120.65(13) . . ? C7 C6 C5 120.46(15) . . ? C8 C7 C6 120.29(17) . . ? C7 C8 C9 119.83(15) . . ? C8 C9 C10 120.17(16) . . ? C9 C10 C5 120.74(15) . . ? N1 C11 C12 112.59(13) . . ? C17 C12 C13 118.89(16) . . ? C17 C12 C11 120.95(16) . . ? C13 C12 C11 120.16(16) . . ? C14 C13 C12 120.3(2) . . ? C15 C14 C13 120.1(2) . . ? C16 C15 C14 120.29(19) . . ? C15 C16 C17 120.1(2) . . ? C12 C17 C16 120.30(19) . . ? C19 C18 C23 117.89(16) . . ? C19 C18 C2 120.16(15) . . ? C23 C18 C2 121.93(16) . . ? C18 C19 C20 121.22(18) . . ? C21 C20 C19 120.0(2) . . ? C20 C21 C22 119.9(2) . . ? C21 C22 C23 120.8(2) . . ? C22 C23 C18 120.1(2) . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.290 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.047 # Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_2a _database_code_depnum_ccdc_archive 'CCDC 682967' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N3 O' _chemical_formula_weight 289.33 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.7985(9) _cell_length_b 5.5755(4) _cell_length_c 19.3734(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.922(1) _cell_angle_gamma 90.00 _cell_volume 1490.27(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6868 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_T_max 0.973 _exptl_absorpt_process_details SADABS _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 9358 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3281 _reflns_number_gt 2698 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0833P)^2^+0.2107P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3281 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1568 _refine_ls_wR_factor_gt 0.1448 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.07986(9) -0.1436(2) 0.24102(7) 0.0637(3) Uani 1 1 d . . . N1 N 0.20077(9) 0.2256(2) 0.27900(6) 0.0472(3) Uani 1 1 d . . . N2 N 0.12647(9) 0.1452(2) 0.31692(6) 0.0451(3) Uani 1 1 d . . . N3 N 0.11409(8) 0.25995(19) 0.37705(6) 0.0435(3) Uani 1 1 d . . . C1 C 0.23866(10) 0.3997(2) 0.31697(7) 0.0427(3) Uani 1 1 d . . . C2 C 0.18438(10) 0.4209(2) 0.37885(7) 0.0406(3) Uani 1 1 d . . . C3 C 0.32360(11) 0.5378(2) 0.29268(7) 0.0455(3) Uani 1 1 d . . . C4 C 0.31392(15) 0.6695(4) 0.23597(9) 0.0662(5) Uani 1 1 d . . . H4A H 0.3660 0.7589 0.2202 0.079 Uiso 1 1 calc R . . H4B H 0.2550 0.6725 0.2119 0.079 Uiso 1 1 calc R . . C5 C 0.41438(10) 0.5221(2) 0.33421(7) 0.0430(3) Uani 1 1 d . . . C6 C 0.48577(14) 0.6979(3) 0.33074(10) 0.0610(4) Uani 1 1 d . . . H6 H 0.4771 0.8272 0.3009 0.073 Uiso 1 1 calc R . . C7 C 0.56883(14) 0.6839(3) 0.37060(12) 0.0728(5) Uani 1 1 d . . . H7 H 0.6155 0.8035 0.3673 0.087 Uiso 1 1 calc R . . C8 C 0.58371(13) 0.4965(3) 0.41493(10) 0.0649(5) Uani 1 1 d . . . H8 H 0.6398 0.4892 0.4421 0.078 Uiso 1 1 calc R . . C9 C 0.51513(13) 0.3195(3) 0.41886(10) 0.0622(4) Uani 1 1 d . . . H9 H 0.5249 0.1904 0.4486 0.075 Uiso 1 1 calc R . . C10 C 0.43136(12) 0.3320(3) 0.37880(9) 0.0523(4) Uani 1 1 d . . . H10 H 0.3855 0.2104 0.3819 0.063 Uiso 1 1 calc R . . C11 C 0.19475(10) 0.5837(2) 0.43830(7) 0.0407(3) Uani 1 1 d . . . C12 C 0.25095(11) 0.7901(2) 0.43552(7) 0.0447(3) Uani 1 1 d . . . H12 H 0.2840 0.8267 0.3954 0.054 Uiso 1 1 calc R . . C13 C 0.25808(12) 0.9416(2) 0.49186(8) 0.0506(4) Uani 1 1 d . . . H13 H 0.2963 1.0786 0.4896 0.061 Uiso 1 1 calc R . . C14 C 0.20873(13) 0.8903(3) 0.55122(8) 0.0563(4) Uani 1 1 d . . . H14 H 0.2130 0.9936 0.5888 0.068 Uiso 1 1 calc R . . C15 C 0.15295(14) 0.6856(3) 0.55489(9) 0.0614(4) Uani 1 1 d . . . H15 H 0.1201 0.6502 0.5952 0.074 Uiso 1 1 calc R . . C16 C 0.14571(12) 0.5335(3) 0.49896(8) 0.0526(4) Uani 1 1 d . . . H16 H 0.1078 0.3961 0.5017 0.063 Uiso 1 1 calc R . . C17 C 0.06700(11) -0.0517(2) 0.29592(8) 0.0487(4) Uani 1 1 d . . . C18 C -0.00710(12) -0.1259(3) 0.34633(9) 0.0567(4) Uani 1 1 d . . . H18A H -0.0576 -0.0075 0.3476 0.085 Uiso 1 1 calc R . . H18B H 0.0225 -0.1405 0.3913 0.085 Uiso 1 1 calc R . . H18C H -0.0342 -0.2775 0.3327 0.085 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 0.0670(8) 0.0604(6) 0.0636(7) -0.0203(6) -0.0022(6) -0.0047(5) N1 0.0480(7) 0.0506(6) 0.0430(6) -0.0043(5) -0.0011(5) 0.0016(5) N2 0.0434(6) 0.0464(6) 0.0454(6) -0.0060(5) -0.0022(5) 0.0007(5) N3 0.0423(6) 0.0448(6) 0.0433(6) -0.0042(5) -0.0027(5) 0.0025(5) C1 0.0441(7) 0.0441(6) 0.0397(7) -0.0008(5) -0.0024(5) 0.0033(5) C2 0.0400(7) 0.0403(6) 0.0415(7) 0.0001(5) -0.0023(5) 0.0037(5) C3 0.0528(8) 0.0454(6) 0.0386(7) -0.0007(5) 0.0071(6) 0.0013(6) C4 0.0693(11) 0.0799(11) 0.0494(9) 0.0139(8) 0.0016(8) -0.0043(9) C5 0.0455(7) 0.0412(6) 0.0423(7) -0.0025(5) 0.0083(6) 0.0003(5) C6 0.0622(10) 0.0480(7) 0.0729(11) 0.0072(7) 0.0013(8) -0.0093(7) C7 0.0574(10) 0.0638(10) 0.0969(15) -0.0041(10) -0.0037(10) -0.0159(8) C8 0.0506(9) 0.0726(10) 0.0714(11) -0.0135(9) -0.0067(8) 0.0048(8) C9 0.0581(10) 0.0649(9) 0.0636(10) 0.0093(8) -0.0017(8) 0.0082(8) C10 0.0502(8) 0.0497(7) 0.0571(9) 0.0074(6) 0.0047(7) -0.0019(6) C11 0.0412(7) 0.0411(6) 0.0397(7) -0.0009(5) -0.0004(5) 0.0048(5) C12 0.0506(8) 0.0425(6) 0.0411(7) 0.0006(5) 0.0037(6) 0.0013(5) C13 0.0578(9) 0.0417(6) 0.0523(8) -0.0043(6) 0.0007(7) -0.0016(6) C14 0.0648(10) 0.0565(8) 0.0476(8) -0.0133(7) 0.0043(7) 0.0015(7) C15 0.0706(11) 0.0656(9) 0.0487(9) -0.0088(7) 0.0183(8) -0.0063(8) C16 0.0554(9) 0.0520(7) 0.0508(8) -0.0045(6) 0.0111(7) -0.0069(6) C17 0.0477(8) 0.0431(6) 0.0551(8) -0.0049(6) -0.0098(6) 0.0029(6) C18 0.0538(9) 0.0494(7) 0.0669(10) -0.0032(7) -0.0027(7) -0.0038(6) _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 C17 1.1962(19) . ? N1 C1 1.3209(18) . ? N1 N2 1.3475(18) . ? N2 N3 1.3424(16) . ? N2 C17 1.4261(18) . ? N3 C2 1.3215(17) . ? C1 C2 1.4286(19) . ? C1 C3 1.485(2) . ? C2 C11 1.4714(18) . ? C3 C4 1.326(2) . ? C3 C5 1.481(2) . ? C5 C10 1.385(2) . ? C5 C6 1.392(2) . ? C6 C7 1.374(3) . ? C7 C8 1.366(3) . ? C8 C9 1.370(3) . ? C9 C10 1.384(2) . ? C11 C12 1.3895(19) . ? C11 C16 1.394(2) . ? C12 C13 1.382(2) . ? C13 C14 1.376(2) . ? C14 C15 1.379(2) . ? C15 C16 1.379(2) . ? C17 C18 1.484(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 C1 N1 N2 103.81(11) . . ? N3 N2 N1 115.04(11) . . ? N3 N2 C17 122.26(12) . . ? N1 N2 C17 122.68(12) . . ? C2 N3 N2 104.05(11) . . ? N1 C1 C2 108.66(12) . . ? N1 C1 C3 120.78(12) . . ? C2 C1 C3 130.56(12) . . ? N3 C2 C1 108.44(12) . . ? N3 C2 C11 120.10(12) . . ? C1 C2 C11 131.46(13) . . ? C4 C3 C5 123.78(15) . . ? C4 C3 C1 118.69(15) . . ? C5 C3 C1 117.53(12) . . ? C10 C5 C6 117.15(14) . . ? C10 C5 C3 121.17(13) . . ? C6 C5 C3 121.68(13) . . ? C7 C6 C5 121.15(16) . . ? C8 C7 C6 120.84(16) . . ? C7 C8 C9 119.27(17) . . ? C8 C9 C10 120.24(16) . . ? C9 C10 C5 121.34(15) . . ? C12 C11 C16 118.54(13) . . ? C12 C11 C2 121.85(12) . . ? C16 C11 C2 119.60(12) . . ? C13 C12 C11 120.54(13) . . ? C14 C13 C12 120.20(14) . . ? C13 C14 C15 119.95(14) . . ? C16 C15 C14 120.14(15) . . ? C15 C16 C11 120.62(14) . . ? O1 C17 N2 119.37(15) . . ? O1 C17 C18 125.41(14) . . ? N2 C17 C18 115.22(13) . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.214 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.039 # Attachment 'Structure2.CIF' data_7d _database_code_depnum_ccdc_archive 'CCDC 682968' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 Cl N3 O' _chemical_formula_weight 311.76 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' Cl Cl 0.1484 0.1585 '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 8.1063(6) _cell_length_b 9.5886(6) _cell_length_c 11.0798(8) _cell_angle_alpha 75.304(1) _cell_angle_beta 78.028(1) _cell_angle_gamma 68.630(1) _cell_volume 769.42(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4117 _cell_measurement_theta_min 27.52 _cell_measurement_theta_max 2.32 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.253 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _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_% none _diffrn_reflns_number 5072 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0595 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3282 _reflns_number_gt 2762 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.1038P)^2^+0.0869P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3282 _refine_ls_number_parameters 227 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0565 _refine_ls_wR_factor_ref 0.1745 _refine_ls_wR_factor_gt 0.1634 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.030 _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 0.31658(15) 0.15931(14) 0.49334(11) 0.0555(3) Uani 1 1 d . . . N1 N 0.72433(17) 0.17778(15) 0.52337(12) 0.0475(3) Uani 1 1 d . A . N2 N 0.75737(17) 0.20637(15) 0.62510(12) 0.0489(3) Uani 1 1 d D . . N3 N 0.61498(18) 0.26979(15) 0.70198(13) 0.0492(3) Uani 1 1 d . A . C1 C 0.54573(19) 0.22506(15) 0.53529(13) 0.0412(3) Uani 1 1 d . . . C2 C 0.4771(2) 0.28239(15) 0.64658(13) 0.0424(3) Uani 1 1 d . A . C3 C 0.44786(18) 0.19781(15) 0.44900(14) 0.0414(3) Uani 1 1 d . A . C4 C 0.50940(19) 0.21929(15) 0.31200(13) 0.0424(3) Uani 1 1 d . . . C5 C 0.5977(2) 0.32356(19) 0.25296(16) 0.0530(4) Uani 1 1 d . A . H5 H 0.6270 0.3763 0.3006 0.064 Uiso 1 1 calc R . . C6 C 0.6420(3) 0.3491(2) 0.12394(18) 0.0667(5) Uani 1 1 d . . . H6 H 0.6984 0.4206 0.0846 0.080 Uiso 1 1 calc R A . C7 C 0.6025(3) 0.2683(3) 0.05338(18) 0.0712(5) Uani 1 1 d . A . H7 H 0.6332 0.2849 -0.0335 0.085 Uiso 1 1 calc R . . C8 C 0.5179(3) 0.1634(2) 0.11139(19) 0.0711(6) Uani 1 1 d . . . H8 H 0.4939 0.1077 0.0636 0.085 Uiso 1 1 calc R A . C9 C 0.4680(3) 0.13990(19) 0.24005(17) 0.0570(4) Uani 1 1 d . A . H9 H 0.4070 0.0713 0.2783 0.068 Uiso 1 1 calc R . . C10 C 0.29116(19) 0.35240(15) 0.70025(14) 0.0430(3) Uani 1 1 d . . . C11 C 0.1713(2) 0.46832(17) 0.62625(15) 0.0507(4) Uani 1 1 d . A . H11 H 0.2069 0.4985 0.5412 0.061 Uiso 1 1 calc R . . C12 C -0.0009(2) 0.53905(19) 0.67857(19) 0.0618(5) Uani 1 1 d . . . H12 H -0.0794 0.6177 0.6286 0.074 Uiso 1 1 calc R A . C13 C -0.0567(3) 0.4942(2) 0.8033(2) 0.0672(5) Uani 1 1 d . A . H13 H -0.1729 0.5414 0.8377 0.081 Uiso 1 1 calc R . . C14 C 0.0606(3) 0.3786(3) 0.87735(19) 0.0716(5) Uani 1 1 d . . . H14 H 0.0232 0.3474 0.9619 0.086 Uiso 1 1 calc R A . C15 C 0.2338(3) 0.3086(2) 0.82637(16) 0.0597(4) Uani 1 1 d . A . H15 H 0.3124 0.2316 0.8773 0.072 Uiso 1 1 calc R . . Cl1 Cl 0.8906(2) -0.0324(3) 0.86874(13) 0.0990(7) Uani 0.638(6) 1 d PD A 1 C16 C 0.9383(7) 0.1678(12) 0.6565(11) 0.063(3) Uani 0.638(6) 1 d PD A 1 H16A H 1.0167 0.1886 0.5802 0.076 Uiso 0.638(6) 1 calc PR A 1 H16B H 0.9357 0.2317 0.7125 0.076 Uiso 0.638(6) 1 calc PR A 1 C17 C 1.0092(4) 0.0073(4) 0.7166(3) 0.0664(10) Uani 0.638(6) 1 d PD A 1 H17A H 1.1343 -0.0180 0.7242 0.080 Uiso 0.638(6) 1 calc PR A 1 H17B H 1.0009 -0.0564 0.6642 0.080 Uiso 0.638(6) 1 calc PR A 1 Cl1' Cl 0.9153(6) -0.0949(6) 0.8123(8) 0.135(3) Uani 0.362(6) 1 d PD A 2 C16' C 0.9430(15) 0.158(2) 0.6453(18) 0.065(5) Uani 0.362(6) 1 d PD A 2 H16C H 0.9780 0.2482 0.6317 0.078 Uiso 0.362(6) 1 calc PR A 2 H16D H 1.0165 0.0981 0.5833 0.078 Uiso 0.362(6) 1 calc PR A 2 C17' C 0.9806(9) 0.0652(8) 0.7752(8) 0.078(2) Uani 0.362(6) 1 d PD A 2 H17C H 0.9184 0.1290 0.8370 0.094 Uiso 0.362(6) 1 calc PR A 2 H17D H 1.1076 0.0337 0.7799 0.094 Uiso 0.362(6) 1 calc PR A 2 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 0.0415(6) 0.0705(7) 0.0580(7) -0.0137(5) -0.0009(5) -0.0248(5) N1 0.0360(6) 0.0587(7) 0.0454(7) -0.0067(5) -0.0027(5) -0.0165(5) N2 0.0359(6) 0.0626(7) 0.0473(7) -0.0047(6) -0.0083(5) -0.0175(5) N3 0.0417(7) 0.0571(7) 0.0480(7) -0.0085(6) -0.0103(5) -0.0142(5) C1 0.0359(7) 0.0445(6) 0.0404(7) -0.0047(5) -0.0047(5) -0.0124(5) C2 0.0394(7) 0.0440(6) 0.0415(7) -0.0054(5) -0.0082(5) -0.0113(5) C3 0.0337(6) 0.0418(6) 0.0458(7) -0.0079(5) -0.0057(5) -0.0093(5) C4 0.0352(7) 0.0446(6) 0.0432(7) -0.0087(5) -0.0075(5) -0.0068(5) C5 0.0513(9) 0.0589(8) 0.0484(8) -0.0084(7) -0.0044(7) -0.0204(7) C6 0.0636(11) 0.0756(11) 0.0513(10) -0.0004(8) 0.0000(8) -0.0237(9) C7 0.0727(13) 0.0809(12) 0.0418(9) -0.0092(8) -0.0043(8) -0.0077(10) C8 0.0899(15) 0.0673(10) 0.0551(10) -0.0205(8) -0.0223(10) -0.0120(10) C9 0.0657(11) 0.0530(8) 0.0555(9) -0.0102(7) -0.0178(8) -0.0181(7) C10 0.0398(7) 0.0440(6) 0.0429(7) -0.0105(5) -0.0074(6) -0.0087(5) C11 0.0475(8) 0.0488(7) 0.0480(8) -0.0032(6) -0.0102(7) -0.0088(6) C12 0.0471(9) 0.0552(9) 0.0690(11) -0.0073(8) -0.0156(8) 0.0006(7) C13 0.0459(9) 0.0689(10) 0.0719(12) -0.0220(9) 0.0027(8) -0.0018(8) C14 0.0623(12) 0.0832(12) 0.0484(9) -0.0127(9) 0.0055(8) -0.0066(10) C15 0.0533(10) 0.0658(9) 0.0426(8) -0.0050(7) -0.0074(7) -0.0024(8) Cl1 0.0802(7) 0.1056(11) 0.0709(8) 0.0145(6) -0.0092(5) -0.0056(7) C16 0.028(3) 0.096(6) 0.065(4) -0.004(3) -0.011(2) -0.025(3) C17 0.0394(13) 0.084(2) 0.0616(18) -0.0273(16) -0.0120(12) 0.0083(13) Cl1' 0.085(2) 0.113(2) 0.186(5) 0.066(3) -0.062(3) -0.0483(18) C16' 0.059(9) 0.082(8) 0.062(7) -0.003(6) -0.016(5) -0.036(6) C17' 0.046(3) 0.108(5) 0.080(5) -0.009(4) -0.027(3) -0.020(3) _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 1.2197(18) . ? N1 N2 1.3240(19) . ? N1 C1 1.3386(19) . ? N2 N3 1.3308(19) . ? N2 C16' 1.452(9) . ? N2 C16 1.470(5) . ? N3 C2 1.3373(19) . ? C1 C2 1.403(2) . ? C1 C3 1.4846(19) . ? C2 C10 1.473(2) . ? C3 C4 1.482(2) . ? C4 C9 1.390(2) . ? C4 C5 1.391(2) . ? C5 C6 1.381(2) . ? C6 C7 1.380(3) . ? C7 C8 1.374(3) . ? C8 C9 1.382(3) . ? C10 C15 1.386(2) . ? C10 C11 1.390(2) . ? C11 C12 1.385(2) . ? C12 C13 1.371(3) . ? C13 C14 1.378(3) . ? C14 C15 1.385(3) . ? Cl1 C17 1.783(4) . ? C16 C17 1.462(10) . ? Cl1' C17' 1.729(7) . ? C16' C17' 1.514(15) . ? 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 N2 N1 C1 103.29(12) . . ? N1 N2 N3 116.00(12) . . ? N1 N2 C16' 117.3(9) . . ? N3 N2 C16' 126.6(9) . . ? N1 N2 C16 123.5(5) . . ? N3 N2 C16 120.5(5) . . ? C16' N2 C16 6.3(14) . . ? N2 N3 C2 103.75(12) . . ? N1 C1 C2 108.95(13) . . ? N1 C1 C3 122.15(13) . . ? C2 C1 C3 128.44(13) . . ? N3 C2 C1 108.01(13) . . ? N3 C2 C10 121.48(13) . . ? C1 C2 C10 130.46(13) . . ? O1 C3 C4 121.54(13) . . ? O1 C3 C1 118.58(13) . . ? C4 C3 C1 119.87(12) . . ? C9 C4 C5 119.40(14) . . ? C9 C4 C3 118.93(13) . . ? C5 C4 C3 121.55(13) . . ? C6 C5 C4 120.24(16) . . ? C7 C6 C5 120.00(18) . . ? C8 C7 C6 120.02(17) . . ? C7 C8 C9 120.64(17) . . ? C8 C9 C4 119.66(17) . . ? C15 C10 C11 118.58(15) . . ? C15 C10 C2 120.86(14) . . ? C11 C10 C2 120.51(14) . . ? C12 C11 C10 120.33(15) . . ? C13 C12 C11 120.64(16) . . ? C12 C13 C14 119.54(17) . . ? C13 C14 C15 120.27(17) . . ? C14 C15 C10 120.63(16) . . ? C17 C16 N2 111.6(6) . . ? C16 C17 Cl1 111.7(5) . . ? N2 C16' C17' 114.1(10) . . ? C16' C17' Cl1' 112.8(9) . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.924 _refine_diff_density_max 0.245 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.051 # Attachment 'Structure5.CIF' data_N-2-4a(7a) _database_code_depnum_ccdc_archive 'CCDC 682969' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H17 N3 O' _chemical_formula_weight 339.39 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 P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.4845(8) _cell_length_b 20.369(2) _cell_length_c 20.976(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3625.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9755 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 27.02 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.9664 _exptl_absorpt_correction_T_max 0.9907 _exptl_absorpt_process_details SADABS _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_% none _diffrn_reflns_number 25799 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0649 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 27.53 _reflns_number_total 8259 _reflns_number_gt 5061 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0687P)^2^+0.2106P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(18) _refine_ls_number_reflns 8259 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0998 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1501 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.41382(18) 0.88067(11) 0.11533(11) 0.0822(7) Uani 1 1 d . . . O2 O -0.07108(19) 0.37379(11) 0.14733(12) 0.0828(7) Uani 1 1 d . . . N1 N 0.8264(2) 0.88768(11) 0.11519(12) 0.0594(6) Uani 1 1 d . . . N2 N 0.9094(2) 0.93456(10) 0.14146(12) 0.0580(6) Uani 1 1 d . . . N3 N 0.8312(2) 0.97543(11) 0.17971(12) 0.0605(6) Uani 1 1 d . . . N4 N 0.3433(2) 0.36099(11) 0.14286(11) 0.0582(6) Uani 1 1 d . . . N5 N 0.4212(2) 0.31189(10) 0.16804(11) 0.0554(5) Uani 1 1 d . . . N6 N 0.3388(2) 0.27079(11) 0.20419(11) 0.0590(6) Uani 1 1 d . . . C1 C 0.6794(2) 0.89861(13) 0.13871(13) 0.0532(6) Uani 1 1 d . . . C2 C 0.6847(3) 0.95318(13) 0.17825(13) 0.0518(6) Uani 1 1 d . . . C3 C 0.5465(3) 0.85775(13) 0.11524(13) 0.0574(6) Uani 1 1 d . . . C4 C 0.5772(3) 0.79043(13) 0.09137(13) 0.0541(6) Uani 1 1 d . . . C5 C 0.7010(3) 0.75174(14) 0.11226(14) 0.0632(7) Uani 1 1 d . . . H5 H 0.7717 0.7684 0.1420 0.076 Uiso 1 1 calc R . . C6 C 0.7205(4) 0.68932(15) 0.08964(17) 0.0759(8) Uani 1 1 d . . . H6 H 0.8035 0.6636 0.1044 0.091 Uiso 1 1 calc R . . C7 C 0.6186(4) 0.66482(16) 0.04564(19) 0.0830(10) Uani 1 1 d . . . H7 H 0.6320 0.6223 0.0304 0.100 Uiso 1 1 calc R . . C8 C 0.4980(4) 0.70195(17) 0.02399(18) 0.0844(10) Uani 1 1 d . . . H8 H 0.4305 0.6850 -0.0068 0.101 Uiso 1 1 calc R . . C9 C 0.4737(3) 0.76388(16) 0.04669(15) 0.0727(8) Uani 1 1 d . . . H9 H 0.3883 0.7884 0.0324 0.087 Uiso 1 1 calc R . . C10 C 0.5618(3) 0.98641(13) 0.21713(12) 0.0543(6) Uani 1 1 d . . . C11 C 0.4439(3) 0.95156(16) 0.24684(13) 0.0623(7) Uani 1 1 d . . . H11 H 0.4362 0.9065 0.2404 0.075 Uiso 1 1 calc R . . C12 C 0.3382(3) 0.98231(18) 0.28555(15) 0.0732(8) Uani 1 1 d . . . H12 H 0.2615 0.9577 0.3063 0.088 Uiso 1 1 calc R . . C13 C 0.3432(4) 1.0484(2) 0.29426(17) 0.0835(10) Uani 1 1 d . . . H13 H 0.2691 1.0688 0.3202 0.100 Uiso 1 1 calc R . . C14 C 0.4597(4) 1.08551(17) 0.26417(18) 0.0851(10) Uani 1 1 d . . . H14 H 0.4647 1.1307 0.2700 0.102 Uiso 1 1 calc R . . C15 C 0.5689(3) 1.05342(15) 0.22505(15) 0.0679(8) Uani 1 1 d . . . H15 H 0.6466 1.0775 0.2043 0.081 Uiso 1 1 calc R . . C16 C 1.0788(3) 0.94278(13) 0.12848(16) 0.0661(8) Uani 1 1 d . . . H16A H 1.1173 0.9045 0.1059 0.079 Uiso 1 1 calc R . . H16B H 1.1352 0.9456 0.1686 0.079 Uiso 1 1 calc R . . C17 C 1.1129(2) 1.00249(13) 0.09000(14) 0.0549(6) Uani 1 1 d . . . C18 C 1.2200(3) 1.04794(15) 0.11215(16) 0.0714(8) Uani 1 1 d . . . H18 H 1.2675 1.0418 0.1517 0.086 Uiso 1 1 calc R . . C19 C 1.2569(4) 1.10175(18) 0.0766(2) 0.0904(11) Uani 1 1 d . . . H19 H 1.3298 1.1320 0.0919 0.108 Uiso 1 1 calc R . . C20 C 1.1875(4) 1.11165(18) 0.0188(2) 0.0891(11) Uani 1 1 d . . . H20 H 1.2133 1.1485 -0.0052 0.107 Uiso 1 1 calc R . . C21 C 1.0800(4) 1.0676(2) -0.00410(17) 0.0864(10) Uani 1 1 d . . . H21 H 1.0321 1.0746 -0.0434 0.104 Uiso 1 1 calc R . . C22 C 1.0426(3) 1.01223(16) 0.03134(15) 0.0698(8) Uani 1 1 d . . . H22 H 0.9705 0.9818 0.0157 0.084 Uiso 1 1 calc R . . C23 C 0.1944(2) 0.35124(13) 0.16529(13) 0.0518(6) Uani 1 1 d . . . C24 C 0.1932(3) 0.29442(13) 0.20279(13) 0.0523(6) Uani 1 1 d . . . C25 C 0.0634(3) 0.39400(14) 0.14225(13) 0.0577(6) Uani 1 1 d . . . C26 C 0.0960(3) 0.45790(13) 0.11248(12) 0.0539(6) Uani 1 1 d . . . C27 C -0.0152(3) 0.48237(16) 0.07026(15) 0.0749(9) Uani 1 1 d . . . H27 H -0.1072 0.4587 0.0629 0.090 Uiso 1 1 calc R . . C28 C 0.0078(4) 0.54073(18) 0.03920(18) 0.0862(10) Uani 1 1 d . . . H28 H -0.0670 0.5561 0.0104 0.103 Uiso 1 1 calc R . . C29 C 0.1415(4) 0.57610(17) 0.05080(18) 0.0862(10) Uani 1 1 d . . . H29 H 0.1579 0.6156 0.0296 0.103 Uiso 1 1 calc R . . C30 C 0.2508(3) 0.55403(14) 0.09300(16) 0.0699(8) Uani 1 1 d . . . H30 H 0.3404 0.5790 0.1011 0.084 Uiso 1 1 calc R . . C31 C 0.2302(3) 0.49563(14) 0.12355(14) 0.0601(7) Uani 1 1 d . . . H31 H 0.3063 0.4808 0.1520 0.072 Uiso 1 1 calc R . . C32 C 0.0661(3) 0.26084(14) 0.23896(12) 0.0549(6) Uani 1 1 d . . . C33 C 0.0661(3) 0.19331(16) 0.24235(16) 0.0736(8) Uani 1 1 d . . . H33 H 0.1416 0.1690 0.2206 0.088 Uiso 1 1 calc R . . C34 C -0.0497(4) 0.16161(19) 0.27918(19) 0.0958(12) Uani 1 1 d . . . H34 H -0.0514 0.1161 0.2823 0.115 Uiso 1 1 calc R . . C35 C -0.1603(4) 0.1991(2) 0.31052(19) 0.0962(12) Uani 1 1 d . . . H35 H -0.2381 0.1787 0.3346 0.115 Uiso 1 1 calc R . . C36 C -0.1571(4) 0.2644(2) 0.30668(17) 0.0882(11) Uani 1 1 d . . . H36 H -0.2325 0.2886 0.3286 0.106 Uiso 1 1 calc R . . C37 C -0.0459(3) 0.29675(17) 0.27136(14) 0.0686(8) Uani 1 1 d . . . H37 H -0.0459 0.3424 0.2693 0.082 Uiso 1 1 calc R . . C38 C 0.5894(3) 0.30180(13) 0.15608(15) 0.0613(7) Uani 1 1 d . . . H38A H 0.6416 0.2921 0.1961 0.074 Uiso 1 1 calc R . . H38B H 0.6342 0.3421 0.1394 0.074 Uiso 1 1 calc R . . C39 C 0.6211(2) 0.24728(12) 0.11012(13) 0.0513(6) Uani 1 1 d . . . C40 C 0.5435(3) 0.24193(15) 0.05295(15) 0.0672(8) Uani 1 1 d . . . H40 H 0.4642 0.2717 0.0428 0.081 Uiso 1 1 calc R . . C41 C 0.5814(4) 0.19358(18) 0.01098(16) 0.0800(9) Uani 1 1 d . . . H41 H 0.5274 0.1905 -0.0275 0.096 Uiso 1 1 calc R . . C42 C 0.6982(4) 0.14935(18) 0.02473(19) 0.0870(10) Uani 1 1 d . . . H42 H 0.7239 0.1166 -0.0043 0.104 Uiso 1 1 calc R . . C43 C 0.7769(4) 0.15375(18) 0.08153(19) 0.0900(11) Uani 1 1 d . . . H43 H 0.8563 0.1239 0.0913 0.108 Uiso 1 1 calc R . . C44 C 0.7379(3) 0.20238(14) 0.12396(16) 0.0709(8) Uani 1 1 d . . . H44 H 0.7911 0.2051 0.1626 0.085 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 0.0373(8) 0.0912(15) 0.1180(18) -0.0202(13) -0.0067(10) 0.0025(9) O2 0.0401(8) 0.0883(15) 0.1200(18) 0.0210(13) -0.0031(10) -0.0019(10) N1 0.0435(9) 0.0574(13) 0.0774(16) -0.0026(12) 0.0020(10) -0.0047(10) N2 0.0330(9) 0.0569(13) 0.0843(16) 0.0001(12) -0.0027(10) -0.0027(9) N3 0.0430(10) 0.0606(14) 0.0778(16) -0.0013(12) -0.0042(10) 0.0018(10) N4 0.0454(9) 0.0593(13) 0.0699(15) -0.0037(11) -0.0034(10) 0.0057(10) N5 0.0357(9) 0.0581(13) 0.0723(14) -0.0010(11) 0.0005(10) 0.0040(10) N6 0.0459(10) 0.0663(14) 0.0649(15) -0.0001(12) -0.0033(10) -0.0004(10) C1 0.0370(10) 0.0575(15) 0.0652(17) 0.0058(14) -0.0025(11) -0.0045(11) C2 0.0427(11) 0.0542(15) 0.0586(16) 0.0019(13) -0.0051(11) -0.0015(11) C3 0.0454(11) 0.0636(16) 0.0632(17) -0.0016(14) -0.0015(11) -0.0030(12) C4 0.0487(12) 0.0593(16) 0.0543(15) -0.0008(12) 0.0038(12) -0.0112(12) C5 0.0604(14) 0.0599(17) 0.0691(18) 0.0045(14) -0.0074(14) -0.0095(13) C6 0.0809(19) 0.0584(18) 0.088(2) 0.0049(17) -0.0031(17) -0.0046(16) C7 0.086(2) 0.0559(18) 0.108(3) -0.0131(18) 0.005(2) -0.0121(17) C8 0.0777(19) 0.084(2) 0.091(2) -0.024(2) -0.0102(19) -0.0189(19) C9 0.0587(15) 0.079(2) 0.081(2) -0.0013(17) -0.0130(14) -0.0097(15) C10 0.0501(12) 0.0570(16) 0.0558(15) 0.0014(12) -0.0081(12) -0.0008(12) C11 0.0548(13) 0.0743(19) 0.0579(17) 0.0068(14) 0.0005(13) -0.0003(14) C12 0.0642(16) 0.095(2) 0.0599(18) -0.0052(17) 0.0087(14) 0.0024(17) C13 0.0609(17) 0.108(3) 0.081(2) -0.022(2) 0.0042(16) 0.0158(19) C14 0.085(2) 0.072(2) 0.099(3) -0.0256(19) -0.017(2) 0.0103(18) C15 0.0577(14) 0.0628(18) 0.083(2) -0.0029(15) 0.0042(15) -0.0022(14) C16 0.0331(10) 0.0605(17) 0.105(2) 0.0078(16) -0.0018(13) 0.0022(11) C17 0.0345(10) 0.0566(15) 0.0735(17) -0.0016(13) 0.0013(11) 0.0053(10) C18 0.0586(14) 0.0762(19) 0.079(2) 0.0120(17) -0.0114(15) -0.0210(14) C19 0.079(2) 0.081(2) 0.111(3) 0.017(2) -0.007(2) -0.0243(18) C20 0.0679(17) 0.080(2) 0.119(3) 0.032(2) 0.015(2) 0.0061(18) C21 0.0689(19) 0.117(3) 0.073(2) 0.021(2) 0.0049(17) 0.023(2) C22 0.0526(14) 0.079(2) 0.078(2) -0.0145(17) -0.0062(14) 0.0084(14) C23 0.0371(10) 0.0521(15) 0.0662(16) -0.0069(13) -0.0017(11) 0.0025(10) C24 0.0433(11) 0.0565(16) 0.0573(16) -0.0077(13) -0.0028(11) 0.0004(11) C25 0.0401(11) 0.0679(17) 0.0651(16) -0.0051(14) -0.0021(12) 0.0012(12) C26 0.0532(12) 0.0552(15) 0.0533(15) -0.0047(12) 0.0027(12) 0.0090(12) C27 0.0555(15) 0.085(2) 0.084(2) -0.0030(18) -0.0129(15) 0.0036(15) C28 0.085(2) 0.086(2) 0.088(2) 0.015(2) -0.0177(19) 0.019(2) C29 0.101(3) 0.068(2) 0.089(3) 0.0137(18) 0.004(2) 0.0158(19) C30 0.0687(16) 0.0573(17) 0.084(2) -0.0059(16) 0.0017(16) -0.0027(15) C31 0.0548(13) 0.0587(16) 0.0669(17) -0.0034(14) -0.0056(13) 0.0094(12) C32 0.0522(12) 0.0611(17) 0.0514(15) 0.0061(12) -0.0053(12) -0.0026(12) C33 0.0553(14) 0.076(2) 0.090(2) 0.0097(17) -0.0047(15) -0.0021(15) C34 0.083(2) 0.091(3) 0.113(3) 0.043(2) -0.020(2) -0.014(2) C35 0.0673(19) 0.129(3) 0.092(3) 0.042(3) 0.0083(18) -0.010(2) C36 0.0672(18) 0.125(3) 0.073(2) 0.019(2) 0.0048(16) 0.000(2) C37 0.0574(14) 0.088(2) 0.0606(18) -0.0015(16) 0.0024(13) -0.0004(15) C38 0.0352(10) 0.0656(17) 0.083(2) -0.0080(15) -0.0045(12) 0.0039(11) C39 0.0354(10) 0.0548(15) 0.0637(16) 0.0009(12) 0.0030(11) -0.0048(10) C40 0.0515(14) 0.0731(19) 0.077(2) 0.0023(16) -0.0113(14) -0.0058(14) C41 0.0660(17) 0.107(3) 0.067(2) -0.0151(19) -0.0063(16) -0.0168(19) C42 0.0703(18) 0.100(3) 0.091(3) -0.033(2) 0.0176(19) -0.0028(19) C43 0.079(2) 0.095(3) 0.096(3) -0.018(2) 0.006(2) 0.0336(19) C44 0.0578(14) 0.081(2) 0.074(2) -0.0046(17) -0.0039(14) 0.0208(14) _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 1.219(3) . ? O2 C25 1.218(3) . ? N1 N2 1.308(3) . ? N1 C1 1.360(3) . ? N2 N3 1.333(3) . ? N2 C16 1.473(3) . ? N3 C2 1.324(3) . ? N4 N5 1.310(3) . ? N4 C23 1.363(3) . ? N5 N6 1.328(3) . ? N5 C38 1.463(3) . ? N6 C24 1.327(3) . ? C1 C2 1.388(4) . ? C1 C3 1.485(3) . ? C2 C10 1.487(3) . ? C3 C4 1.483(4) . ? C4 C5 1.384(4) . ? C4 C9 1.393(4) . ? C5 C6 1.367(4) . ? C6 C7 1.359(5) . ? C7 C8 1.351(5) . ? C8 C9 1.364(4) . ? C10 C11 1.376(4) . ? C10 C15 1.376(4) . ? C11 C12 1.362(4) . ? C12 C13 1.359(5) . ? C13 C14 1.395(5) . ? C14 C15 1.400(4) . ? C16 C17 1.488(4) . ? C17 C18 1.378(4) . ? C17 C22 1.382(4) . ? C18 C19 1.362(4) . ? C19 C20 1.363(5) . ? C20 C21 1.367(5) . ? C21 C22 1.387(5) . ? C23 C24 1.399(4) . ? C23 C25 1.492(3) . ? C24 C32 1.485(3) . ? C25 C26 1.470(4) . ? C26 C27 1.387(4) . ? C26 C31 1.393(4) . ? C27 C28 1.370(4) . ? C28 C29 1.366(5) . ? C29 C30 1.359(4) . ? C30 C31 1.362(4) . ? C32 C33 1.377(4) . ? C32 C37 1.378(4) . ? C33 C34 1.407(4) . ? C34 C35 1.377(5) . ? C35 C36 1.332(5) . ? C36 C37 1.369(4) . ? C38 C39 1.495(4) . ? C39 C40 1.372(4) . ? C39 C44 1.380(3) . ? C40 C41 1.360(4) . ? C41 C42 1.370(5) . ? C42 C43 1.369(5) . ? C43 C44 1.372(4) . ? 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 N2 N1 C1 102.8(2) . . ? N1 N2 N3 116.22(18) . . ? N1 N2 C16 122.0(2) . . ? N3 N2 C16 121.7(2) . . ? C2 N3 N2 103.9(2) . . ? N5 N4 C23 102.6(2) . . ? N4 N5 N6 116.45(18) . . ? N4 N5 C38 122.0(2) . . ? N6 N5 C38 121.5(2) . . ? C24 N6 N5 104.4(2) . . ? N1 C1 C2 108.6(2) . . ? N1 C1 C3 119.0(2) . . ? C2 C1 C3 132.2(2) . . ? N3 C2 C1 108.6(2) . . ? N3 C2 C10 119.3(2) . . ? C1 C2 C10 132.1(2) . . ? O1 C3 C4 121.1(2) . . ? O1 C3 C1 119.1(2) . . ? C4 C3 C1 119.8(2) . . ? C5 C4 C9 118.0(3) . . ? C5 C4 C3 123.5(2) . . ? C9 C4 C3 118.4(2) . . ? C6 C5 C4 120.7(3) . . ? C7 C6 C5 120.0(3) . . ? C8 C7 C6 120.3(3) . . ? C7 C8 C9 121.0(3) . . ? C8 C9 C4 119.9(3) . . ? C11 C10 C15 119.2(3) . . ? C11 C10 C2 121.6(2) . . ? C15 C10 C2 119.2(2) . . ? C12 C11 C10 120.7(3) . . ? C13 C12 C11 121.0(3) . . ? C12 C13 C14 119.8(3) . . ? C13 C14 C15 118.8(3) . . ? C10 C15 C14 120.3(3) . . ? N2 C16 C17 112.5(2) . . ? C18 C17 C22 119.3(3) . . ? C18 C17 C16 119.6(3) . . ? C22 C17 C16 121.1(3) . . ? C19 C18 C17 120.5(3) . . ? C18 C19 C20 120.5(3) . . ? C19 C20 C21 120.2(3) . . ? C20 C21 C22 119.9(3) . . ? C17 C22 C21 119.7(3) . . ? N4 C23 C24 108.8(2) . . ? N4 C23 C25 119.6(2) . . ? C24 C23 C25 131.2(2) . . ? N6 C24 C23 107.8(2) . . ? N6 C24 C32 119.8(2) . . ? C23 C24 C32 132.3(2) . . ? O2 C25 C26 120.8(2) . . ? O2 C25 C23 118.2(3) . . ? C26 C25 C23 121.0(2) . . ? C27 C26 C31 117.7(3) . . ? C27 C26 C25 117.5(2) . . ? C31 C26 C25 124.8(2) . . ? C28 C27 C26 121.2(3) . . ? C29 C28 C27 119.5(3) . . ? C30 C29 C28 120.6(3) . . ? C29 C30 C31 120.5(3) . . ? C30 C31 C26 120.5(3) . . ? C33 C32 C37 120.3(3) . . ? C33 C32 C24 119.1(2) . . ? C37 C32 C24 120.5(3) . . ? C32 C33 C34 119.1(3) . . ? C35 C34 C33 118.9(3) . . ? C36 C35 C34 120.7(3) . . ? C35 C36 C37 121.8(4) . . ? C36 C37 C32 119.1(3) . . ? N5 C38 C39 113.0(2) . . ? C40 C39 C44 118.4(3) . . ? C40 C39 C38 122.4(2) . . ? C44 C39 C38 119.1(2) . . ? C41 C40 C39 120.7(3) . . ? C40 C41 C42 120.8(3) . . ? C43 C42 C41 119.5(3) . . ? C42 C43 C44 119.6(3) . . ? C43 C44 C39 121.0(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.244 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.038 # Attachment 'Structure4.CIF' data_N-1-5a _database_code_depnum_ccdc_archive 'CCDC 682970' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H19 N3 O' _chemical_formula_weight 341.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 18.7577(12) _cell_length_b 10.4782(6) _cell_length_c 19.7381(12) _cell_angle_alpha 90.00 _cell_angle_beta 110.054(1) _cell_angle_gamma 90.00 _cell_volume 3644.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5553 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _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_% none _diffrn_reflns_number 24801 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0559 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.49 _reflns_number_total 8190 _reflns_number_gt 5540 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0708P)^2^+0.3769P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8190 _refine_ls_number_parameters 471 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1516 _refine_ls_wR_factor_gt 0.1313 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.32469(7) 0.74329(10) 0.17121(6) 0.0550(3) Uani 1 1 d . . . H1 H 0.2903 0.7023 0.1776 0.083 Uiso 1 1 calc R . . O2 O 0.84503(7) 1.01086(11) 0.18800(6) 0.0592(3) Uani 1 1 d . . . H2 H 0.8160 1.0639 0.1947 0.089 Uiso 1 1 calc R . . N1 N 0.28758(7) 1.00682(11) 0.19222(7) 0.0480(3) Uani 1 1 d . . . N2 N 0.25765(8) 1.10487(12) 0.21710(8) 0.0563(3) Uani 1 1 d . . . N3 N 0.27511(8) 1.08862(12) 0.28664(8) 0.0530(3) Uani 1 1 d . . . N4 N 0.78257(8) 0.75488(13) 0.19106(7) 0.0549(3) Uani 1 1 d . . . N5 N 0.73976(9) 0.66595(14) 0.20739(9) 0.0660(4) Uani 1 1 d . . . N6 N 0.75088(9) 0.67733(14) 0.27618(8) 0.0635(4) Uani 1 1 d . . . C1 C 0.32389(8) 0.92493(13) 0.24613(8) 0.0418(3) Uani 1 1 d . . . C2 C 0.31590(8) 0.97907(13) 0.30690(8) 0.0438(3) Uani 1 1 d . . . C3 C 0.27410(10) 1.00227(16) 0.11464(8) 0.0541(4) Uani 1 1 d . . . H3A H 0.3124 0.9486 0.1064 0.065 Uiso 1 1 calc R . . H3B H 0.2798 1.0876 0.0981 0.065 Uiso 1 1 calc R . . C4 C 0.19680(9) 0.95206(14) 0.07067(8) 0.0477(4) Uani 1 1 d . . . C5 C 0.14236(10) 0.91975(17) 0.10013(9) 0.0595(4) Uani 1 1 d . . . H5 H 0.1532 0.9270 0.1496 0.071 Uiso 1 1 calc R . . C6 C 0.07199(11) 0.87679(19) 0.05672(11) 0.0693(5) Uani 1 1 d . . . H6 H 0.0357 0.8551 0.0771 0.083 Uiso 1 1 calc R . . C7 C 0.05521(12) 0.86580(18) -0.01638(11) 0.0702(5) Uani 1 1 d . . . H7 H 0.0078 0.8365 -0.0455 0.084 Uiso 1 1 calc R . . C8 C 0.10872(13) 0.89824(19) -0.04613(10) 0.0707(5) Uani 1 1 d . . . H8 H 0.0975 0.8916 -0.0957 0.085 Uiso 1 1 calc R . . C9 C 0.17867(11) 0.94050(17) -0.00322(10) 0.0616(4) Uani 1 1 d . . . H9 H 0.2147 0.9618 -0.0241 0.074 Uiso 1 1 calc R . . C10 C 0.36599(9) 0.80813(13) 0.23529(8) 0.0442(3) Uani 1 1 d . . . H10 H 0.3725 0.7501 0.2759 0.053 Uiso 1 1 calc R . . C11 C 0.44434(9) 0.84267(12) 0.23396(8) 0.0453(3) Uani 1 1 d . . . C12 C 0.49984(10) 0.88346(19) 0.29646(10) 0.0678(5) Uani 1 1 d . . . H12 H 0.4885 0.8908 0.3386 0.081 Uiso 1 1 calc R . . C13 C 0.57189(12) 0.9135(2) 0.29759(13) 0.0844(6) Uani 1 1 d . . . H13 H 0.6084 0.9416 0.3401 0.101 Uiso 1 1 calc R . . C14 C 0.58950(12) 0.9019(2) 0.23611(14) 0.0804(6) Uani 1 1 d . . . H14 H 0.6382 0.9209 0.2368 0.096 Uiso 1 1 calc R . . C15 C 0.53524(12) 0.8624(2) 0.17371(13) 0.0758(6) Uani 1 1 d . . . H15 H 0.5470 0.8548 0.1318 0.091 Uiso 1 1 calc R . . C16 C 0.46279(11) 0.83339(16) 0.17248(10) 0.0597(4) Uani 1 1 d . . . H16 H 0.4262 0.8073 0.1296 0.072 Uiso 1 1 calc R . . C17 C 0.34674(8) 0.94340(14) 0.38369(8) 0.0452(3) Uani 1 1 d . . . C18 C 0.34872(10) 0.81888(15) 0.40795(9) 0.0547(4) Uani 1 1 d . . . H18 H 0.3291 0.7534 0.3750 0.066 Uiso 1 1 calc R . . C19 C 0.37947(11) 0.79116(17) 0.48036(10) 0.0625(4) Uani 1 1 d . . . H19 H 0.3806 0.7071 0.4959 0.075 Uiso 1 1 calc R . . C20 C 0.40852(11) 0.88634(19) 0.52987(10) 0.0680(5) Uani 1 1 d . . . H20 H 0.4297 0.8672 0.5787 0.082 Uiso 1 1 calc R . . C21 C 0.40596(13) 1.0101(2) 0.50646(10) 0.0788(6) Uani 1 1 d . . . H21 H 0.4251 1.0752 0.5398 0.095 Uiso 1 1 calc R . . C22 C 0.37555(12) 1.03888(16) 0.43444(10) 0.0662(5) Uani 1 1 d . . . H22 H 0.3742 1.1233 0.4195 0.079 Uiso 1 1 calc R . . C23 C 0.82184(9) 0.82443(14) 0.24975(8) 0.0474(3) Uani 1 1 d . . . C24 C 0.80105(9) 0.77332(15) 0.30463(9) 0.0517(4) Uani 1 1 d . . . C25 C 0.78281(10) 0.76022(18) 0.11681(9) 0.0599(4) Uani 1 1 d . . . H25A H 0.7962 0.6768 0.1035 0.072 Uiso 1 1 calc R . . H25B H 0.8215 0.8200 0.1147 0.072 Uiso 1 1 calc R . . C26 C 0.70755(10) 0.79997(16) 0.06288(9) 0.0562(4) Uani 1 1 d . . . C27 C 0.67264(13) 0.72264(19) 0.00445(11) 0.0737(5) Uani 1 1 d . . . H27 H 0.6945 0.6447 0.0002 0.088 Uiso 1 1 calc R . . C28 C 0.60593(14) 0.7592(2) -0.04764(12) 0.0875(7) Uani 1 1 d . . . H28 H 0.5830 0.7058 -0.0867 0.105 Uiso 1 1 calc R . . C29 C 0.57320(13) 0.8733(2) -0.04233(13) 0.0844(6) Uani 1 1 d . . . H29 H 0.5281 0.8978 -0.0778 0.101 Uiso 1 1 calc R . . C30 C 0.60698(12) 0.9518(2) 0.01547(13) 0.0779(6) Uani 1 1 d . . . H30 H 0.5846 1.0295 0.0192 0.093 Uiso 1 1 calc R . . C31 C 0.67419(11) 0.91574(19) 0.06827(11) 0.0669(5) Uani 1 1 d . . . H31 H 0.6969 0.9692 0.1073 0.080 Uiso 1 1 calc R . . C32 C 0.87459(9) 0.93276(13) 0.25043(8) 0.0467(3) Uani 1 1 d . . . H32 H 0.8795 0.9858 0.2927 0.056 Uiso 1 1 calc R . . C33 C 0.95376(9) 0.89060(13) 0.25527(8) 0.0454(3) Uani 1 1 d . . . C34 C 0.97363(10) 0.76569(15) 0.24977(10) 0.0605(4) Uani 1 1 d . . . H34 H 0.9377 0.7014 0.2432 0.073 Uiso 1 1 calc R . . C35 C 1.04691(11) 0.73510(18) 0.25390(12) 0.0717(5) Uani 1 1 d . . . H35 H 1.0595 0.6505 0.2493 0.086 Uiso 1 1 calc R . . C36 C 1.10067(11) 0.82774(19) 0.26462(11) 0.0698(5) Uani 1 1 d . . . H36 H 1.1498 0.8066 0.2677 0.084 Uiso 1 1 calc R . . C37 C 1.08171(11) 0.95143(19) 0.27085(12) 0.0764(6) Uani 1 1 d . . . H37 H 1.1183 1.0150 0.2787 0.092 Uiso 1 1 calc R . . C38 C 1.00875(11) 0.98325(15) 0.26567(11) 0.0649(5) Uani 1 1 d . . . H38 H 0.9964 1.0684 0.2692 0.078 Uiso 1 1 calc R . . C39 C 0.82340(10) 0.80847(15) 0.38107(9) 0.0541(4) Uani 1 1 d . . . C40 C 0.77126(12) 0.80287(18) 0.41641(10) 0.0681(5) Uani 1 1 d . . . H40 H 0.7220 0.7756 0.3914 0.082 Uiso 1 1 calc R . . C41 C 0.79078(15) 0.8368(2) 0.48759(12) 0.0820(6) Uani 1 1 d . . . H41 H 0.7549 0.8327 0.5103 0.098 Uiso 1 1 calc R . . C42 C 0.86366(17) 0.8772(2) 0.52552(12) 0.0865(7) Uani 1 1 d . . . H42 H 0.8767 0.9026 0.5734 0.104 Uiso 1 1 calc R . . C43 C 0.91681(15) 0.8793(2) 0.49169(12) 0.0857(7) Uani 1 1 d . . . H43 H 0.9664 0.9038 0.5173 0.103 Uiso 1 1 calc R . . C44 C 0.89713(12) 0.84542(19) 0.42028(10) 0.0700(5) Uani 1 1 d . . . H44 H 0.9335 0.8473 0.3981 0.084 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 0.0650(8) 0.0540(6) 0.0520(7) -0.0117(5) 0.0276(6) -0.0146(5) O2 0.0677(8) 0.0580(6) 0.0614(7) 0.0155(5) 0.0343(6) 0.0156(6) N1 0.0475(7) 0.0484(6) 0.0491(7) 0.0048(5) 0.0181(6) 0.0029(6) N2 0.0554(8) 0.0525(7) 0.0613(9) 0.0047(6) 0.0202(7) 0.0105(6) N3 0.0514(8) 0.0510(7) 0.0563(8) -0.0008(6) 0.0180(6) 0.0072(6) N4 0.0526(8) 0.0620(8) 0.0514(8) 0.0006(6) 0.0193(6) -0.0059(6) N5 0.0614(9) 0.0723(9) 0.0644(10) 0.0000(7) 0.0218(8) -0.0176(7) N6 0.0602(9) 0.0703(9) 0.0608(9) 0.0045(7) 0.0218(7) -0.0151(7) C1 0.0395(8) 0.0431(7) 0.0437(8) 0.0017(6) 0.0155(6) -0.0020(6) C2 0.0408(8) 0.0438(7) 0.0482(8) -0.0036(6) 0.0170(6) -0.0001(6) C3 0.0553(10) 0.0630(9) 0.0480(9) 0.0138(7) 0.0228(8) 0.0018(8) C4 0.0535(9) 0.0462(7) 0.0460(8) 0.0096(6) 0.0204(7) 0.0064(7) C5 0.0574(10) 0.0743(10) 0.0499(9) 0.0082(8) 0.0224(8) 0.0006(8) C6 0.0573(11) 0.0823(12) 0.0732(13) 0.0082(10) 0.0286(10) -0.0023(9) C7 0.0595(11) 0.0740(11) 0.0687(13) 0.0011(9) 0.0112(9) -0.0009(9) C8 0.0794(14) 0.0809(12) 0.0490(10) -0.0032(9) 0.0185(10) -0.0028(10) C9 0.0719(12) 0.0679(10) 0.0529(10) 0.0012(8) 0.0317(9) -0.0031(9) C10 0.0545(9) 0.0398(6) 0.0418(8) -0.0012(6) 0.0212(7) -0.0013(6) C11 0.0493(9) 0.0383(6) 0.0497(9) 0.0022(6) 0.0188(7) 0.0068(6) C12 0.0505(10) 0.0895(13) 0.0593(11) -0.0112(9) 0.0135(8) 0.0117(9) C13 0.0485(11) 0.1065(16) 0.0876(16) -0.0203(13) 0.0096(10) 0.0065(11) C14 0.0493(11) 0.0806(13) 0.1127(19) 0.0024(12) 0.0296(12) 0.0028(10) C15 0.0687(13) 0.0873(13) 0.0858(15) 0.0082(11) 0.0450(12) 0.0032(11) C16 0.0578(10) 0.0691(10) 0.0571(10) -0.0010(8) 0.0261(8) -0.0027(8) C17 0.0429(8) 0.0511(7) 0.0436(8) -0.0066(6) 0.0174(6) 0.0001(6) C18 0.0647(11) 0.0533(8) 0.0480(9) -0.0070(7) 0.0217(8) -0.0104(7) C19 0.0730(12) 0.0639(10) 0.0522(10) 0.0042(8) 0.0236(9) -0.0050(9) C20 0.0709(12) 0.0861(12) 0.0438(9) -0.0014(9) 0.0158(9) -0.0034(10) C21 0.0976(16) 0.0742(12) 0.0518(11) -0.0182(9) 0.0092(10) -0.0127(11) C22 0.0840(14) 0.0530(9) 0.0546(10) -0.0102(8) 0.0148(9) -0.0038(9) C23 0.0430(8) 0.0532(8) 0.0483(9) 0.0043(7) 0.0187(7) 0.0026(6) C24 0.0472(9) 0.0569(8) 0.0528(9) 0.0086(7) 0.0193(7) -0.0018(7) C25 0.0588(10) 0.0724(10) 0.0519(10) -0.0040(8) 0.0232(8) 0.0019(8) C26 0.0550(10) 0.0664(9) 0.0504(9) -0.0002(8) 0.0224(8) -0.0067(8) C27 0.0781(14) 0.0714(11) 0.0657(12) -0.0074(9) 0.0171(10) -0.0093(10) C28 0.0809(15) 0.1013(16) 0.0663(14) -0.0101(12) 0.0072(11) -0.0119(13) C29 0.0627(13) 0.1132(17) 0.0694(14) 0.0167(13) 0.0123(10) -0.0035(13) C30 0.0627(12) 0.0873(13) 0.0893(15) 0.0132(12) 0.0334(11) 0.0103(11) C31 0.0575(11) 0.0762(11) 0.0709(12) -0.0063(9) 0.0273(9) -0.0012(9) C32 0.0526(9) 0.0449(7) 0.0479(8) 0.0032(6) 0.0241(7) 0.0016(6) C33 0.0481(8) 0.0455(7) 0.0454(8) 0.0007(6) 0.0197(7) -0.0011(6) C34 0.0521(10) 0.0473(8) 0.0796(12) -0.0036(8) 0.0195(9) -0.0018(7) C35 0.0607(12) 0.0585(9) 0.0934(15) -0.0033(9) 0.0231(10) 0.0129(9) C36 0.0492(10) 0.0837(12) 0.0810(14) 0.0087(10) 0.0279(9) 0.0068(9) C37 0.0568(11) 0.0711(11) 0.1068(17) 0.0078(11) 0.0349(11) -0.0126(9) C38 0.0604(11) 0.0483(8) 0.0917(14) -0.0037(8) 0.0332(10) -0.0067(8) C39 0.0575(10) 0.0559(8) 0.0519(9) 0.0107(7) 0.0223(8) 0.0006(7) C40 0.0710(12) 0.0801(11) 0.0608(11) 0.0108(9) 0.0324(10) 0.0009(10) C41 0.1048(18) 0.0894(14) 0.0669(13) 0.0107(11) 0.0489(13) 0.0073(13) C42 0.132(2) 0.0749(12) 0.0543(12) 0.0070(10) 0.0339(14) -0.0056(13) C43 0.0919(16) 0.0931(14) 0.0587(12) 0.0108(11) 0.0085(11) -0.0234(13) C44 0.0675(12) 0.0865(12) 0.0555(11) 0.0099(9) 0.0206(9) -0.0098(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10 1.4105(18) . ? O2 C32 1.4237(18) . ? N1 N2 1.3421(18) . ? N1 C1 1.3548(18) . ? N1 C3 1.465(2) . ? N2 N3 1.3084(19) . ? N3 C2 1.3613(19) . ? N4 N5 1.3397(19) . ? N4 C23 1.353(2) . ? N4 C25 1.468(2) . ? N5 N6 1.307(2) . ? N6 C24 1.360(2) . ? C1 C2 1.381(2) . ? C1 C10 1.5111(19) . ? C2 C17 1.473(2) . ? C3 C4 1.506(2) . ? C4 C5 1.379(2) . ? C4 C9 1.385(2) . ? C5 C6 1.380(3) . ? C6 C7 1.372(3) . ? C7 C8 1.368(3) . ? C8 C9 1.369(3) . ? C10 C11 1.523(2) . ? C11 C16 1.374(2) . ? C11 C12 1.381(2) . ? C12 C13 1.380(3) . ? C13 C14 1.368(3) . ? C14 C15 1.366(3) . ? C15 C16 1.385(3) . ? C17 C18 1.386(2) . ? C17 C22 1.388(2) . ? C18 C19 1.376(2) . ? C19 C20 1.372(3) . ? C20 C21 1.372(3) . ? C21 C22 1.371(3) . ? C23 C24 1.379(2) . ? C23 C32 1.503(2) . ? C24 C39 1.468(2) . ? C25 C26 1.506(2) . ? C26 C27 1.377(3) . ? C26 C31 1.386(3) . ? C27 C28 1.374(3) . ? C28 C29 1.365(3) . ? C29 C30 1.373(3) . ? C30 C31 1.385(3) . ? C32 C33 1.521(2) . ? C33 C34 1.375(2) . ? C33 C38 1.380(2) . ? C34 C35 1.386(3) . ? C35 C36 1.363(3) . ? C36 C37 1.361(3) . ? C37 C38 1.378(3) . ? C39 C40 1.384(2) . ? C39 C44 1.388(3) . ? C40 C41 1.372(3) . ? C41 C42 1.381(3) . ? C42 C43 1.377(4) . ? C43 C44 1.376(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 N2 N1 C1 110.98(12) . . ? N2 N1 C3 117.62(12) . . ? C1 N1 C3 131.35(13) . . ? N3 N2 N1 107.38(12) . . ? N2 N3 C2 109.35(12) . . ? N5 N4 C23 111.34(13) . . ? N5 N4 C25 118.29(14) . . ? C23 N4 C25 130.32(14) . . ? N6 N5 N4 106.94(13) . . ? N5 N6 C24 109.75(13) . . ? N1 C1 C2 104.30(12) . . ? N1 C1 C10 123.24(12) . . ? C2 C1 C10 132.34(13) . . ? N3 C2 C1 107.98(13) . . ? N3 C2 C17 119.94(13) . . ? C1 C2 C17 131.93(13) . . ? N1 C3 C4 113.62(12) . . ? C5 C4 C9 118.21(16) . . ? C5 C4 C3 123.25(14) . . ? C9 C4 C3 118.52(14) . . ? C4 C5 C6 120.48(17) . . ? C7 C6 C5 120.40(18) . . ? C8 C7 C6 119.53(19) . . ? C7 C8 C9 120.24(18) . . ? C8 C9 C4 121.13(17) . . ? O1 C10 C1 111.34(12) . . ? O1 C10 C11 109.61(11) . . ? C1 C10 C11 111.37(11) . . ? C16 C11 C12 118.01(16) . . ? C16 C11 C10 122.35(14) . . ? C12 C11 C10 119.63(14) . . ? C13 C12 C11 121.25(19) . . ? C14 C13 C12 119.9(2) . . ? C15 C14 C13 119.7(2) . . ? C14 C15 C16 120.4(2) . . ? C11 C16 C15 120.78(18) . . ? C18 C17 C22 118.14(15) . . ? C18 C17 C2 123.30(13) . . ? C22 C17 C2 118.57(14) . . ? C19 C18 C17 120.63(15) . . ? C20 C19 C18 120.60(17) . . ? C19 C20 C21 119.20(17) . . ? C22 C21 C20 120.74(17) . . ? C21 C22 C17 120.68(17) . . ? N4 C23 C24 104.23(14) . . ? N4 C23 C32 125.31(13) . . ? C24 C23 C32 130.46(15) . . ? N6 C24 C23 107.75(15) . . ? N6 C24 C39 121.56(14) . . ? C23 C24 C39 130.69(15) . . ? N4 C25 C26 113.14(14) . . ? C27 C26 C31 118.80(18) . . ? C27 C26 C25 119.36(17) . . ? C31 C26 C25 121.75(16) . . ? C28 C27 C26 120.8(2) . . ? C29 C28 C27 120.3(2) . . ? C28 C29 C30 119.8(2) . . ? C29 C30 C31 120.2(2) . . ? C30 C31 C26 119.98(19) . . ? O2 C32 C23 111.50(13) . . ? O2 C32 C33 107.67(12) . . ? C23 C32 C33 114.01(12) . . ? C34 C33 C38 118.19(15) . . ? C34 C33 C32 123.83(14) . . ? C38 C33 C32 117.98(13) . . ? C33 C34 C35 120.37(16) . . ? C36 C35 C34 120.68(17) . . ? C37 C36 C35 119.34(18) . . ? C36 C37 C38 120.50(18) . . ? C37 C38 C33 120.91(16) . . ? C40 C39 C44 118.16(18) . . ? C40 C39 C24 120.37(17) . . ? C44 C39 C24 121.46(16) . . ? C41 C40 C39 121.3(2) . . ? C40 C41 C42 120.1(2) . . ? C43 C42 C41 119.3(2) . . ? C44 C43 C42 120.5(2) . . ? C43 C44 C39 120.62(19) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.188 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.047