Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 #======================================================== # 1. SUBMISSION DETAILS _publ_contact_author ; Dr David Adams Department of Chemistry Heriot-Watt University Edinburgh EH14 4AS ; _publ_contact_author_phone '0131 451-8021' _publ_contact_author_fax '0131 451 3180' _publ_contact_author_email D.R.Adams@hw.ac.uk _publ_requested_coeditor_name ? _publ_contact_letter ; Here is the CIF file for the three structures in a manuscript entitled,"Concise Routes to Pyrazolo[1,5-a]pyridin-3-yl Pyridazin-3-ones" Please email the deposition numbers to me Thank you Georgina Rosair (G.M.Rosair@hw.ac.uk) ; # 3. TITLE AND AUTHOR LIST _publ_section_title ;Concise Routes to Pyrazolo[1,5-a]pyridin-3-yl Pyridazin-3-ones ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address K.A.Johnston ; School of Engineering & Physical Sciences Heriot-Watt University Edinburgh EH14 4AS UK ; R.Allcock ; School of Engineering & Physical Sciences Heriot-Watt University Edinburgh EH14 4AS UK ; G.M.Rosair ; School of Engineering & Physical Sciences Heriot-Watt University Edinburgh EH14 4AS UK ; Z.Jiang ; School of Engineering & Physical Sciences Heriot-Watt University Edinburgh EH14 4AS UK ; I.D.Collier ; School of Engineering & Physical Sciences Heriot-Watt University Edinburgh EH14 4AS UK ; ; H.Blakli ; ; School of Engineering & Physical Sciences Heriot-Watt University Edinburgh EH14 4AS UK ; P.D.Bailey ; School of Engineering & Physical Sciences Heriot-Watt University Edinburgh EH14 4AS UK ; K.M.Morgan ; School of Engineering & Physical Sciences Heriot-Watt University Edinburgh EH14 4AS UK ; Y.Kohno ;Discovery Research Laboratories, Kyorin Pharmaceutical Co., Ltd, 2399-1, Nogi, Nogi-machi, Simotsuga-gun, Tochigi 329-0114, Japan ; D.R.Adams ; School of Engineering & Physical Sciences Heriot-Watt University Edinburgh EH14 4AS UK ; _publ_contact_author_name 'Dr David Adams' #====================================================== data_x81506cmpd28 _database_code_depnum_ccdc_archive 'CCDC 659630' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H15 N3' _chemical_formula_sum 'C15 H15 N3' _chemical_formula_weight 237.30 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5122(5) _cell_length_b 13.5695(7) _cell_length_c 9.9716(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.400(2) _cell_angle_gamma 90.00 _cell_volume 1234.73(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9844 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 36.14 _exptl_crystal_description TRIANGULAR _exptl_crystal_colour colourless _exptl_crystal_size_max 0.88 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.60 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.875 _exptl_absorpt_correction_T_max 0.9547 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45006 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0161 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 36.32 _reflns_number_total 5941 _reflns_number_gt 5125 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0636P)^2^+0.2219P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5941 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1132 _refine_ls_wR_factor_gt 0.1076 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 0.80772(6) 0.05081(4) 0.89884(5) 0.01374(9) Uani 1 1 d . . . N2 N 0.80069(5) 0.09403(4) 1.01992(5) 0.01228(9) Uani 1 1 d . . . C3 C 0.91564(7) 0.09641(5) 1.13884(6) 0.01503(11) Uani 1 1 d . . . H3 H 1.0075 0.0682 1.1405 0.018 Uiso 1 1 calc R . . C4 C 0.89522(7) 0.14030(5) 1.25501(6) 0.01678(11) Uani 1 1 d . . . H4 H 0.9728 0.1414 1.3394 0.020 Uiso 1 1 calc R . . C5 C 0.75829(7) 0.18436(5) 1.25017(7) 0.01636(11) Uani 1 1 d . . . H5 H 0.7459 0.2165 1.3307 0.020 Uiso 1 1 calc R . . C6 C 0.64395(7) 0.18092(4) 1.13033(6) 0.01409(10) Uani 1 1 d . . . H6 H 0.5530 0.2112 1.1271 0.017 Uiso 1 1 calc R . . C7 C 0.66314(6) 0.13164(4) 1.01128(6) 0.01160(9) Uani 1 1 d . . . C8 C 0.57711(6) 0.11080(4) 0.87485(6) 0.01137(9) Uani 1 1 d . . . C9 C 0.67237(6) 0.06153(4) 0.81100(6) 0.01209(10) Uani 1 1 d . . . C10 C 0.42013(6) 0.13166(4) 0.81599(6) 0.01157(9) Uani 1 1 d . . . N11 N 0.37476(6) 0.16165(4) 0.68176(5) 0.01381(9) Uani 1 1 d . . . C12 C 0.23122(7) 0.17800(5) 0.62591(7) 0.01643(11) Uani 1 1 d . . . H12 H 0.1988 0.1987 0.5311 0.020 Uiso 1 1 calc R . . C13 C 0.12691(7) 0.16659(5) 0.69800(8) 0.01805(12) Uani 1 1 d . . . H13 H 0.0262 0.1792 0.6538 0.022 Uiso 1 1 calc R . . C14 C 0.17403(7) 0.13627(5) 0.83657(8) 0.01798(11) Uani 1 1 d . . . H14 H 0.1059 0.1278 0.8893 0.022 Uiso 1 1 calc R . . C15 C 0.32229(7) 0.11855(5) 0.89692(7) 0.01510(11) Uani 1 1 d . . . H15 H 0.3570 0.0979 0.9916 0.018 Uiso 1 1 calc R . . C16 C 0.63790(6) 0.01646(4) 0.66729(6) 0.01325(10) Uani 1 1 d . . . H16 H 0.5380 0.0391 0.6131 0.016 Uiso 1 1 calc R . . C17 C 0.74655(8) 0.05006(5) 0.58872(7) 0.01828(12) Uani 1 1 d . . . H17A H 0.7445 0.1221 0.5814 0.027 Uiso 1 1 calc R . . H17B H 0.7191 0.0212 0.4948 0.027 Uiso 1 1 calc R . . H17C H 0.8455 0.0284 0.6397 0.027 Uiso 1 1 calc R . . C18 C 0.63455(8) -0.09626(5) 0.67702(7) 0.01850(12) Uani 1 1 d . . . H18A H 0.7316 -0.1203 0.7297 0.028 Uiso 1 1 calc R . . H18B H 0.6079 -0.1245 0.5827 0.028 Uiso 1 1 calc R . . H18C H 0.5621 -0.1160 0.7249 0.028 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 0.01155(19) 0.0180(2) 0.0117(2) -0.00213(16) 0.00342(15) 0.00220(16) N2 0.01022(19) 0.0148(2) 0.01181(19) -0.00093(15) 0.00316(15) 0.00132(15) C3 0.0117(2) 0.0181(2) 0.0139(2) -0.00153(18) 0.00149(18) 0.00090(18) C4 0.0163(2) 0.0188(3) 0.0140(2) -0.00261(19) 0.00222(19) 0.00036(19) C5 0.0183(3) 0.0171(2) 0.0140(2) -0.00272(19) 0.00500(19) 0.00084(19) C6 0.0152(2) 0.0144(2) 0.0139(2) -0.00087(17) 0.00600(18) 0.00153(18) C7 0.0106(2) 0.0122(2) 0.0127(2) 0.00040(16) 0.00446(17) 0.00100(16) C8 0.0099(2) 0.0129(2) 0.0117(2) 0.00057(16) 0.00383(16) 0.00105(16) C9 0.0106(2) 0.0143(2) 0.0117(2) 0.00017(17) 0.00368(16) 0.00130(16) C10 0.0099(2) 0.0114(2) 0.0139(2) 0.00044(16) 0.00423(17) 0.00067(15) N11 0.01160(19) 0.0152(2) 0.0142(2) 0.00161(16) 0.00293(16) 0.00119(16) C12 0.0122(2) 0.0170(3) 0.0183(3) 0.00059(19) 0.00146(19) 0.00143(18) C13 0.0105(2) 0.0172(3) 0.0254(3) -0.0020(2) 0.0034(2) 0.00071(18) C14 0.0122(2) 0.0188(3) 0.0251(3) -0.0018(2) 0.0087(2) -0.00079(19) C15 0.0126(2) 0.0168(2) 0.0177(2) 0.00107(19) 0.00712(19) -0.00031(18) C16 0.0124(2) 0.0162(2) 0.0113(2) -0.00070(17) 0.00358(17) 0.00176(17) C17 0.0227(3) 0.0191(3) 0.0158(2) -0.0008(2) 0.0099(2) -0.0022(2) C18 0.0236(3) 0.0164(3) 0.0161(3) -0.0011(2) 0.0067(2) -0.0031(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C9 1.3450(7) . ? N1 N2 1.3609(7) . ? N2 C3 1.3677(8) . ? N2 C7 1.3842(7) . ? C3 C4 1.3643(9) . ? C3 H3 0.9500 . ? C4 C5 1.4216(9) . ? C4 H4 0.9500 . ? C5 C6 1.3709(9) . ? C5 H5 0.9500 . ? C6 C7 1.4186(8) . ? C6 H6 0.9500 . ? C7 C8 1.4042(8) . ? C8 C9 1.4138(8) . ? C8 C10 1.4695(8) . ? C9 C16 1.5066(8) . ? C10 N11 1.3481(8) . ? C10 C15 1.4047(8) . ? N11 C12 1.3395(8) . ? C12 C13 1.3886(9) . ? C12 H12 0.9500 . ? C13 C14 1.3892(10) . ? C13 H13 0.9500 . ? C14 C15 1.3891(9) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.5320(9) . ? C16 C18 1.5336(9) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 N2 104.67(5) . . ? N1 N2 C3 123.50(5) . . ? N1 N2 C7 112.71(5) . . ? C3 N2 C7 123.75(5) . . ? C4 C3 N2 118.41(6) . . ? C4 C3 H3 120.8 . . ? N2 C3 H3 120.8 . . ? C3 C4 C5 120.23(6) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 120.61(6) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 119.18(5) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? N2 C7 C8 105.55(5) . . ? N2 C7 C6 117.67(5) . . ? C8 C7 C6 136.74(5) . . ? C7 C8 C9 105.02(5) . . ? C7 C8 C10 126.63(5) . . ? C9 C8 C10 128.27(5) . . ? N1 C9 C8 112.04(5) . . ? N1 C9 C16 119.12(5) . . ? C8 C9 C16 128.70(5) . . ? N11 C10 C15 122.03(5) . . ? N11 C10 C8 117.33(5) . . ? C15 C10 C8 120.64(5) . . ? C12 N11 C10 117.77(5) . . ? N11 C12 C13 124.04(6) . . ? N11 C12 H12 118.0 . . ? C13 C12 H12 118.0 . . ? C12 C13 C14 118.10(6) . . ? C12 C13 H13 121.0 . . ? C14 C13 H13 121.0 . . ? C15 C14 C13 119.02(6) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C10 119.05(6) . . ? C14 C15 H15 120.5 . . ? C10 C15 H15 120.5 . . ? C9 C16 C17 111.63(5) . . ? C9 C16 C18 110.34(5) . . ? C17 C16 C18 110.99(5) . . ? C9 C16 H16 107.9 . . ? C17 C16 H16 107.9 . . ? C18 C16 H16 107.9 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 N2 C3 177.88(6) . . . . ? C9 N1 N2 C7 0.36(7) . . . . ? N1 N2 C3 C4 -178.83(6) . . . . ? C7 N2 C3 C4 -1.58(9) . . . . ? N2 C3 C4 C5 -1.52(10) . . . . ? C3 C4 C5 C6 1.87(10) . . . . ? C4 C5 C6 C7 0.82(9) . . . . ? N1 N2 C7 C8 -0.08(7) . . . . ? C3 N2 C7 C8 -177.60(6) . . . . ? N1 N2 C7 C6 -178.29(5) . . . . ? C3 N2 C7 C6 4.20(9) . . . . ? C5 C6 C7 N2 -3.69(9) . . . . ? C5 C6 C7 C8 178.84(7) . . . . ? N2 C7 C8 C9 -0.21(6) . . . . ? C6 C7 C8 C9 177.46(7) . . . . ? N2 C7 C8 C10 176.84(5) . . . . ? C6 C7 C8 C10 -5.48(11) . . . . ? N2 N1 C9 C8 -0.50(7) . . . . ? N2 N1 C9 C16 -176.59(5) . . . . ? C7 C8 C9 N1 0.46(7) . . . . ? C10 C8 C9 N1 -176.53(6) . . . . ? C7 C8 C9 C16 176.08(6) . . . . ? C10 C8 C9 C16 -0.90(10) . . . . ? C7 C8 C10 N11 142.14(6) . . . . ? C9 C8 C10 N11 -41.49(9) . . . . ? C7 C8 C10 C15 -39.13(9) . . . . ? C9 C8 C10 C15 137.24(6) . . . . ? C15 C10 N11 C12 -0.67(9) . . . . ? C8 C10 N11 C12 178.04(5) . . . . ? C10 N11 C12 C13 0.45(10) . . . . ? N11 C12 C13 C14 -0.07(10) . . . . ? C12 C13 C14 C15 -0.11(10) . . . . ? C13 C14 C15 C10 -0.10(10) . . . . ? N11 C10 C15 C14 0.51(9) . . . . ? C8 C10 C15 C14 -178.16(6) . . . . ? N1 C9 C16 C17 -54.28(7) . . . . ? C8 C9 C16 C17 130.36(6) . . . . ? N1 C9 C16 C18 69.63(7) . . . . ? C8 C9 C16 C18 -105.73(7) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.557 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.054 #===end data_x81507cmpd12 _database_code_depnum_ccdc_archive 'CCDC 659631' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H22 N4 O' _chemical_formula_sum 'C21 H22 N4 O' _chemical_formula_weight 346.43 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 8.1760(5) _cell_length_b 23.3585(15) _cell_length_c 9.0849(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.397(2) _cell_angle_gamma 90.00 _cell_volume 1727.33(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5415 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 31.75 _exptl_crystal_description BLOCK _exptl_crystal_colour yellow _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.62 _exptl_crystal_size_min 0.58 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.909 _exptl_absorpt_correction_T_max 0.9525 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 51389 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 31.82 _reflns_number_total 5899 _reflns_number_gt 5012 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+0.6391P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5899 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1163 _refine_ls_wR_factor_gt 0.1100 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 0.89487(10) 0.05805(3) 0.84114(9) 0.01319(15) Uani 1 1 d . . . N2 N 1.01369(9) 0.03919(3) 0.75764(8) 0.01190(14) Uani 1 1 d . . . C3 C 1.10942(11) -0.00749(4) 0.79416(10) 0.01431(17) Uani 1 1 d . . . H3 H 1.0972 -0.0283 0.8823 0.017 Uiso 1 1 calc R . . C4 C 1.22281(12) -0.02357(4) 0.70169(11) 0.01601(17) Uani 1 1 d . . . H4 H 1.2909 -0.0559 0.7250 0.019 Uiso 1 1 calc R . . C5 C 1.23933(11) 0.00795(4) 0.57054(11) 0.01590(17) Uani 1 1 d . . . H5 H 1.3187 -0.0034 0.5064 0.019 Uiso 1 1 calc R . . C6 C 1.14234(11) 0.05453(4) 0.53549(10) 0.01432(17) Uani 1 1 d . . . H6 H 1.1540 0.0754 0.4473 0.017 Uiso 1 1 calc R . . C7 C 1.02433(10) 0.07153(4) 0.63148(10) 0.01178(16) Uani 1 1 d . . . C8 C 0.90095(11) 0.11328(4) 0.63354(10) 0.01172(15) Uani 1 1 d . . . C9 C 0.82625(11) 0.10262(4) 0.76562(10) 0.01181(16) Uani 1 1 d . . . C10 C 0.85438(11) 0.15459(4) 0.51676(10) 0.01242(16) Uani 1 1 d . . . N11 N 0.70570(10) 0.17407(3) 0.50977(9) 0.01336(15) Uani 1 1 d . . . N12 N 0.65301(10) 0.21108(3) 0.39407(9) 0.01433(15) Uani 1 1 d . . . C13 C 0.75238(12) 0.23887(4) 0.30412(10) 0.01598(17) Uani 1 1 d . . . O13 O 0.69571(10) 0.26919(3) 0.20177(9) 0.02320(17) Uani 1 1 d . . . C14 C 0.93276(12) 0.23075(4) 0.34656(11) 0.01701(18) Uani 1 1 d . . . H14A H 0.9705 0.2594 0.4225 0.020 Uiso 1 1 calc R . . H14B H 0.9934 0.2375 0.2588 0.020 Uiso 1 1 calc R . . C15 C 0.97263(12) 0.17107(4) 0.40665(11) 0.01552(17) Uani 1 1 d . . . H15A H 0.9652 0.1432 0.3243 0.019 Uiso 1 1 calc R . . H15B H 1.0863 0.1703 0.4549 0.019 Uiso 1 1 calc R . . C16 C 0.68641(11) 0.13400(4) 0.82642(10) 0.01338(16) Uani 1 1 d . . . H16 H 0.6868 0.1743 0.7893 0.016 Uiso 1 1 calc R . . C17 C 0.70605(14) 0.13589(5) 0.99499(11) 0.0232(2) Uani 1 1 d . . . H17A H 0.7016 0.0969 1.0341 0.035 Uiso 1 1 calc R . . H17B H 0.6171 0.1587 1.0303 0.035 Uiso 1 1 calc R . . H17C H 0.8121 0.1533 1.0288 0.035 Uiso 1 1 calc R . . C18 C 0.52200(12) 0.10693(5) 0.77033(12) 0.0211(2) Uani 1 1 d . . . H18A H 0.5137 0.1046 0.6622 0.032 Uiso 1 1 calc R . . H18B H 0.4320 0.1305 0.8010 0.032 Uiso 1 1 calc R . . H18C H 0.5149 0.0684 0.8119 0.032 Uiso 1 1 calc R . . C19 C 0.47464(11) 0.21839(4) 0.37547(11) 0.01546(17) Uani 1 1 d . . . H19A H 0.4484 0.2567 0.3327 0.019 Uiso 1 1 calc R . . H19B H 0.4314 0.2167 0.4736 0.019 Uiso 1 1 calc R . . C20 C 0.39078(11) 0.17318(4) 0.27639(10) 0.01310(16) Uani 1 1 d . . . C21 C 0.41819(11) 0.11523(4) 0.30508(10) 0.01505(17) Uani 1 1 d . . . H21 H 0.4892 0.1039 0.3888 0.018 Uiso 1 1 calc R . . C22 C 0.34272(12) 0.07383(4) 0.21242(11) 0.01801(18) Uani 1 1 d . . . H22 H 0.3632 0.0344 0.2323 0.022 Uiso 1 1 calc R . . C23 C 0.23746(13) 0.08997(5) 0.09091(12) 0.0211(2) Uani 1 1 d . . . H23 H 0.1855 0.0616 0.0277 0.025 Uiso 1 1 calc R . . C24 C 0.20814(13) 0.14760(5) 0.06171(11) 0.0213(2) Uani 1 1 d . . . H24 H 0.1357 0.1587 -0.0212 0.026 Uiso 1 1 calc R . . C25 C 0.28509(11) 0.18898(4) 0.15411(11) 0.01668(18) Uani 1 1 d . . . H25 H 0.2653 0.2284 0.1335 0.020 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 0.0134(3) 0.0139(3) 0.0128(3) 0.0000(3) 0.0038(3) 0.0024(3) N2 0.0123(3) 0.0128(3) 0.0108(3) -0.0002(3) 0.0019(2) 0.0013(3) C3 0.0156(4) 0.0135(4) 0.0137(4) 0.0004(3) 0.0008(3) 0.0025(3) C4 0.0148(4) 0.0165(4) 0.0167(4) -0.0004(3) 0.0011(3) 0.0039(3) C5 0.0137(4) 0.0185(4) 0.0160(4) -0.0020(3) 0.0038(3) 0.0020(3) C6 0.0131(4) 0.0166(4) 0.0137(4) -0.0004(3) 0.0033(3) 0.0000(3) C7 0.0115(3) 0.0127(4) 0.0111(4) 0.0001(3) 0.0012(3) -0.0009(3) C8 0.0117(3) 0.0119(4) 0.0117(4) 0.0001(3) 0.0017(3) -0.0006(3) C9 0.0121(4) 0.0123(4) 0.0111(4) -0.0005(3) 0.0017(3) -0.0002(3) C10 0.0141(4) 0.0114(4) 0.0118(4) -0.0001(3) 0.0018(3) -0.0015(3) N11 0.0150(3) 0.0125(3) 0.0124(3) 0.0021(3) -0.0001(3) 0.0002(3) N12 0.0143(3) 0.0135(3) 0.0146(3) 0.0028(3) -0.0013(3) 0.0003(3) C13 0.0210(4) 0.0127(4) 0.0144(4) -0.0002(3) 0.0027(3) -0.0001(3) O13 0.0302(4) 0.0204(4) 0.0191(3) 0.0077(3) 0.0026(3) 0.0044(3) C14 0.0176(4) 0.0155(4) 0.0185(4) 0.0028(3) 0.0047(3) -0.0016(3) C15 0.0160(4) 0.0158(4) 0.0153(4) 0.0024(3) 0.0042(3) 0.0001(3) C16 0.0141(4) 0.0135(4) 0.0129(4) 0.0010(3) 0.0036(3) 0.0024(3) C17 0.0260(5) 0.0305(5) 0.0136(4) -0.0001(4) 0.0049(4) 0.0121(4) C18 0.0138(4) 0.0236(5) 0.0263(5) -0.0015(4) 0.0048(4) -0.0010(3) C19 0.0145(4) 0.0143(4) 0.0172(4) -0.0014(3) -0.0007(3) 0.0030(3) C20 0.0117(4) 0.0152(4) 0.0126(4) 0.0002(3) 0.0021(3) 0.0006(3) C21 0.0155(4) 0.0152(4) 0.0144(4) 0.0007(3) 0.0014(3) 0.0014(3) C22 0.0191(4) 0.0161(4) 0.0194(4) -0.0013(3) 0.0044(3) -0.0018(3) C23 0.0197(4) 0.0256(5) 0.0182(4) -0.0053(4) 0.0019(3) -0.0072(4) C24 0.0166(4) 0.0305(5) 0.0160(4) 0.0022(4) -0.0024(3) -0.0020(4) C25 0.0145(4) 0.0196(4) 0.0158(4) 0.0036(3) 0.0010(3) 0.0012(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 N1 C9 1.3405(11) . ? N1 N2 1.3608(10) . ? N2 C3 1.3648(12) . ? N2 C7 1.3823(11) . ? C3 C4 1.3612(13) . ? C3 H3 0.9500 . ? C4 C5 1.4178(14) . ? C4 H4 0.9500 . ? C5 C6 1.3661(13) . ? C5 H5 0.9500 . ? C6 C7 1.4168(12) . ? C6 H6 0.9500 . ? C7 C8 1.4046(12) . ? C8 C9 1.4187(12) . ? C8 C10 1.4580(12) . ? C9 C16 1.5062(12) . ? C10 N11 1.2938(12) . ? C10 C15 1.5052(13) . ? N11 N12 1.3974(11) . ? N12 C13 1.3690(12) . ? N12 C19 1.4622(12) . ? C13 O13 1.2247(12) . ? C13 C14 1.5009(14) . ? C14 C15 1.5212(13) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.5254(13) . ? C16 C18 1.5289(14) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.5097(13) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C25 1.3916(13) . ? C20 C21 1.3928(13) . ? C21 C22 1.3880(13) . ? C21 H21 0.9500 . ? C22 C23 1.3866(15) . ? C22 H22 0.9500 . ? C23 C24 1.3884(16) . ? C23 H23 0.9500 . ? C24 C25 1.3912(14) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 N2 104.63(7) . . ? N1 N2 C3 123.11(8) . . ? N1 N2 C7 112.90(7) . . ? C3 N2 C7 123.97(8) . . ? C4 C3 N2 118.60(9) . . ? C4 C3 H3 120.7 . . ? N2 C3 H3 120.7 . . ? C3 C4 C5 119.98(9) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.68(9) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 119.59(9) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? N2 C7 C8 105.50(7) . . ? N2 C7 C6 117.18(8) . . ? C8 C7 C6 137.25(8) . . ? C7 C8 C9 104.85(8) . . ? C7 C8 C10 126.06(8) . . ? C9 C8 C10 128.89(8) . . ? N1 C9 C8 112.11(8) . . ? N1 C9 C16 119.07(8) . . ? C8 C9 C16 128.81(8) . . ? N11 C10 C8 116.63(8) . . ? N11 C10 C15 122.46(8) . . ? C8 C10 C15 120.84(8) . . ? C10 N11 N12 118.44(8) . . ? C13 N12 N11 125.74(8) . . ? C13 N12 C19 121.13(8) . . ? N11 N12 C19 113.13(7) . . ? O13 C13 N12 121.61(9) . . ? O13 C13 C14 124.09(9) . . ? N12 C13 C14 114.25(8) . . ? C13 C14 C15 112.35(8) . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? C10 C15 C14 110.09(8) . . ? C10 C15 H15A 109.6 . . ? C14 C15 H15A 109.6 . . ? C10 C15 H15B 109.6 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 108.2 . . ? C9 C16 C17 111.74(8) . . ? C9 C16 C18 110.51(8) . . ? C17 C16 C18 110.66(8) . . ? C9 C16 H16 107.9 . . ? C17 C16 H16 107.9 . . ? C18 C16 H16 107.9 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N12 C19 C20 112.28(7) . . ? N12 C19 H19A 109.1 . . ? C20 C19 H19A 109.1 . . ? N12 C19 H19B 109.1 . . ? C20 C19 H19B 109.1 . . ? H19A C19 H19B 107.9 . . ? C25 C20 C21 118.94(9) . . ? C25 C20 C19 120.24(8) . . ? C21 C20 C19 120.82(8) . . ? C22 C21 C20 120.61(9) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C23 C22 C21 120.04(9) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 119.92(9) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C23 C24 C25 119.88(9) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C20 C25 C24 120.61(9) . . ? C20 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 N2 C3 -177.67(8) . . . . ? C9 N1 N2 C7 1.12(10) . . . . ? N1 N2 C3 C4 178.71(8) . . . . ? C7 N2 C3 C4 0.06(14) . . . . ? N2 C3 C4 C5 -0.09(14) . . . . ? C3 C4 C5 C6 -0.01(15) . . . . ? C4 C5 C6 C7 0.14(14) . . . . ? N1 N2 C7 C8 -1.25(10) . . . . ? C3 N2 C7 C8 177.52(8) . . . . ? N1 N2 C7 C6 -178.71(8) . . . . ? C3 N2 C7 C6 0.06(13) . . . . ? C5 C6 C7 N2 -0.16(13) . . . . ? C5 C6 C7 C8 -176.56(10) . . . . ? N2 C7 C8 C9 0.83(9) . . . . ? C6 C7 C8 C9 177.50(10) . . . . ? N2 C7 C8 C10 -174.42(8) . . . . ? C6 C7 C8 C10 2.26(17) . . . . ? N2 N1 C9 C8 -0.54(10) . . . . ? N2 N1 C9 C16 179.36(8) . . . . ? C7 C8 C9 N1 -0.19(10) . . . . ? C10 C8 C9 N1 174.87(9) . . . . ? C7 C8 C9 C16 179.92(9) . . . . ? C10 C8 C9 C16 -5.02(15) . . . . ? C7 C8 C10 N11 154.50(9) . . . . ? C9 C8 C10 N11 -19.59(14) . . . . ? C7 C8 C10 C15 -22.73(14) . . . . ? C9 C8 C10 C15 163.17(9) . . . . ? C8 C10 N11 N12 -176.19(8) . . . . ? C15 C10 N11 N12 1.00(13) . . . . ? C10 N11 N12 C13 -14.93(13) . . . . ? C10 N11 N12 C19 165.22(8) . . . . ? N11 N12 C13 O13 177.53(9) . . . . ? C19 N12 C13 O13 -2.62(14) . . . . ? N11 N12 C13 C14 -4.98(13) . . . . ? C19 N12 C13 C14 174.87(8) . . . . ? O13 C13 C14 C15 -146.99(10) . . . . ? N12 C13 C14 C15 35.59(12) . . . . ? N11 C10 C15 C14 29.04(12) . . . . ? C8 C10 C15 C14 -153.89(8) . . . . ? C13 C14 C15 C10 -45.88(11) . . . . ? N1 C9 C16 C17 34.28(12) . . . . ? C8 C9 C16 C17 -145.84(10) . . . . ? N1 C9 C16 C18 -89.41(10) . . . . ? C8 C9 C16 C18 90.47(11) . . . . ? C13 N12 C19 C20 93.01(10) . . . . ? N11 N12 C19 C20 -87.13(10) . . . . ? N12 C19 C20 C25 -126.01(9) . . . . ? N12 C19 C20 C21 53.69(12) . . . . ? C25 C20 C21 C22 0.67(14) . . . . ? C19 C20 C21 C22 -179.03(9) . . . . ? C20 C21 C22 C23 -0.74(14) . . . . ? C21 C22 C23 C24 0.26(15) . . . . ? C22 C23 C24 C25 0.29(16) . . . . ? C21 C20 C25 C24 -0.12(14) . . . . ? C19 C20 C25 C24 179.58(9) . . . . ? C23 C24 C25 C20 -0.36(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.520 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.052 #===end data_x81509_0mcmpd13 _database_code_depnum_ccdc_archive 'CCDC 659632' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H20 N4 O' _chemical_formula_sum 'C21 H20 N4 O' _chemical_formula_weight 344.41 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' 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 8.9123(6) _cell_length_b 10.1067(7) _cell_length_c 19.3558(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.980(2) _cell_angle_gamma 90.00 _cell_volume 1743.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2968 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 30.08 _exptl_crystal_description block _exptl_crystal_colour pale_yellow _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.58 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.855 _exptl_absorpt_correction_T_max 0.9530 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32329 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 30.21 _reflns_number_total 5176 _reflns_number_gt 3635 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0218P)^2^+1.3995P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5176 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1009 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.003 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 0.66789(12) 0.05950(12) 0.07433(5) 0.0192(2) Uani 1 1 d . . . N2 N 0.75110(12) 0.08003(11) 0.01687(5) 0.0172(2) Uani 1 1 d . . . C3 C 0.71020(15) 0.03642(13) -0.04796(7) 0.0197(3) Uani 1 1 d . . . H3 H 0.6194 -0.0112 -0.0554 0.024 Uiso 1 1 calc R . . C4 C 0.80264(15) 0.06298(14) -0.10115(7) 0.0206(3) Uani 1 1 d . . . H4 H 0.7760 0.0345 -0.1465 0.025 Uiso 1 1 calc R . . C5 C 0.93869(15) 0.13282(14) -0.08964(7) 0.0208(3) Uani 1 1 d . . . H5 H 1.0024 0.1504 -0.1274 0.025 Uiso 1 1 calc R . . C6 C 0.97944(15) 0.17523(13) -0.02483(6) 0.0187(3) Uani 1 1 d . . . H6 H 1.0708 0.2219 -0.0172 0.022 Uiso 1 1 calc R . . C7 C 0.88235(14) 0.14806(12) 0.03070(6) 0.0163(2) Uani 1 1 d . . . C8 C 0.88377(14) 0.17071(13) 0.10229(6) 0.0163(2) Uani 1 1 d . . . C9 C 0.74938(14) 0.11414(13) 0.12597(6) 0.0174(2) Uani 1 1 d . . . C10 C 1.00572(14) 0.23657(13) 0.14037(6) 0.0160(2) Uani 1 1 d . . . N11 N 1.07028(12) 0.33484(11) 0.10842(5) 0.0183(2) Uani 1 1 d . . . N12 N 1.19042(12) 0.39410(11) 0.13955(5) 0.0189(2) Uani 1 1 d . . . C13 C 1.25037(14) 0.36301(13) 0.20408(7) 0.0186(3) Uani 1 1 d . . . O13 O 1.35796(11) 0.42496(10) 0.22882(5) 0.0258(2) Uani 1 1 d . . . C14 C 1.17716(15) 0.25285(14) 0.23699(7) 0.0201(3) Uani 1 1 d . . . H14 H 1.2129 0.2232 0.2808 0.024 Uiso 1 1 calc R . . C15 C 1.05915(15) 0.19137(13) 0.20673(6) 0.0185(3) Uani 1 1 d . . . H15 H 1.0119 0.1191 0.2290 0.022 Uiso 1 1 calc R . . C16 C 0.68926(15) 0.11468(15) 0.19847(7) 0.0213(3) Uani 1 1 d . . . H16 H 0.7618 0.0653 0.2288 0.026 Uiso 1 1 calc R . . C17 C 0.53702(17) 0.04630(17) 0.20273(7) 0.0303(3) Uani 1 1 d . . . H17A H 0.4626 0.0958 0.1753 0.045 Uiso 1 1 calc R . . H17B H 0.5058 0.0431 0.2510 0.045 Uiso 1 1 calc R . . H17C H 0.5448 -0.0439 0.1846 0.045 Uiso 1 1 calc R . . C18 C 0.67894(17) 0.25691(16) 0.22566(8) 0.0282(3) Uani 1 1 d . . . H18A H 0.7786 0.2978 0.2253 0.042 Uiso 1 1 calc R . . H18B H 0.6416 0.2558 0.2730 0.042 Uiso 1 1 calc R . . H18C H 0.6100 0.3080 0.1960 0.042 Uiso 1 1 calc R . . C19 C 1.25849(16) 0.49785(14) 0.09670(7) 0.0234(3) Uani 1 1 d . . . H19A H 1.3521 0.5299 0.1194 0.028 Uiso 1 1 calc R . . H19B H 1.1885 0.5736 0.0922 0.028 Uiso 1 1 calc R . . C20 C 1.29315(15) 0.44442(13) 0.02602(7) 0.0194(3) Uani 1 1 d . . . C21 C 1.21890(16) 0.49352(14) -0.03221(7) 0.0241(3) Uani 1 1 d . . . H21 H 1.1468 0.5621 -0.0276 0.029 Uiso 1 1 calc R . . C22 C 1.24966(18) 0.44267(16) -0.09731(8) 0.0294(3) Uani 1 1 d . . . H22 H 1.1994 0.4773 -0.1370 0.035 Uiso 1 1 calc R . . C23 C 1.35303(18) 0.34204(16) -0.10416(8) 0.0307(3) Uani 1 1 d . . . H23 H 1.3738 0.3072 -0.1486 0.037 Uiso 1 1 calc R . . C24 C 1.42646(18) 0.29191(16) -0.04619(8) 0.0318(3) Uani 1 1 d . . . H24 H 1.4969 0.2221 -0.0509 0.038 Uiso 1 1 calc R . . C25 C 1.39746(16) 0.34331(15) 0.01860(8) 0.0257(3) Uani 1 1 d . . . H25 H 1.4491 0.3093 0.0581 0.031 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 0.0192(5) 0.0238(6) 0.0147(5) -0.0002(4) 0.0016(4) -0.0018(4) N2 0.0174(5) 0.0196(5) 0.0148(5) 0.0003(4) 0.0003(4) -0.0006(4) C3 0.0205(6) 0.0200(6) 0.0185(6) -0.0025(5) -0.0035(5) 0.0007(5) C4 0.0244(6) 0.0222(7) 0.0149(6) -0.0016(5) -0.0018(5) 0.0034(5) C5 0.0243(6) 0.0220(7) 0.0162(6) 0.0011(5) 0.0030(5) 0.0029(5) C6 0.0194(6) 0.0184(6) 0.0185(6) 0.0018(5) 0.0017(5) 0.0012(5) C7 0.0170(6) 0.0151(6) 0.0166(6) 0.0005(5) -0.0011(4) 0.0015(5) C8 0.0176(6) 0.0167(6) 0.0147(5) 0.0010(5) 0.0002(4) 0.0014(5) C9 0.0190(6) 0.0181(6) 0.0153(6) 0.0012(5) 0.0003(4) 0.0005(5) C10 0.0168(6) 0.0169(6) 0.0144(5) -0.0009(5) 0.0012(4) 0.0023(5) N11 0.0187(5) 0.0194(5) 0.0166(5) -0.0011(4) -0.0016(4) -0.0017(4) N12 0.0201(5) 0.0205(6) 0.0163(5) -0.0003(4) -0.0004(4) -0.0031(4) C13 0.0186(6) 0.0203(6) 0.0169(6) -0.0048(5) -0.0001(5) 0.0023(5) O13 0.0258(5) 0.0289(5) 0.0226(5) -0.0047(4) -0.0041(4) -0.0049(4) C14 0.0225(6) 0.0233(7) 0.0145(6) -0.0004(5) -0.0015(5) 0.0031(5) C15 0.0208(6) 0.0190(6) 0.0159(6) 0.0020(5) 0.0010(5) 0.0017(5) C16 0.0208(6) 0.0285(7) 0.0145(6) 0.0008(5) 0.0015(5) -0.0027(6) C17 0.0266(7) 0.0436(9) 0.0208(7) -0.0003(6) 0.0050(5) -0.0103(7) C18 0.0272(7) 0.0347(8) 0.0230(7) -0.0059(6) 0.0055(6) 0.0009(6) C19 0.0293(7) 0.0204(7) 0.0204(6) -0.0001(5) 0.0008(5) -0.0071(6) C20 0.0202(6) 0.0186(6) 0.0193(6) 0.0020(5) 0.0012(5) -0.0054(5) C21 0.0275(7) 0.0204(7) 0.0243(7) 0.0028(5) -0.0004(5) 0.0026(6) C22 0.0357(8) 0.0324(8) 0.0200(7) 0.0044(6) -0.0017(6) -0.0006(7) C23 0.0356(8) 0.0337(8) 0.0230(7) -0.0030(6) 0.0077(6) -0.0022(7) C24 0.0288(8) 0.0300(8) 0.0368(8) 0.0002(7) 0.0074(6) 0.0076(6) C25 0.0224(7) 0.0281(7) 0.0267(7) 0.0055(6) -0.0011(5) 0.0019(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 N1 C9 1.3441(16) . ? N1 N2 1.3631(15) . ? N2 C3 1.3734(16) . ? N2 C7 1.3791(16) . ? C3 C4 1.3564(19) . ? C3 H3 0.9500 . ? C4 C5 1.4174(19) . ? C4 H4 0.9500 . ? C5 C6 1.3688(18) . ? C5 H5 0.9500 . ? C6 C7 1.4181(18) . ? C6 H6 0.9500 . ? C7 C8 1.4043(17) . ? C8 C9 1.4108(18) . ? C8 C10 1.4629(17) . ? C9 C16 1.5106(18) . ? C10 N11 1.3085(17) . ? C10 C15 1.4367(17) . ? N11 N12 1.3587(15) . ? N12 C13 1.3863(16) . ? N12 C19 1.4739(17) . ? C13 O13 1.2349(16) . ? C13 C14 1.4440(19) . ? C14 C15 1.3469(18) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.5262(19) . ? C16 C18 1.534(2) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.5078(19) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.3889(19) . ? C20 C25 1.391(2) . ? C21 C22 1.392(2) . ? C21 H21 0.9500 . ? C22 C23 1.380(2) . ? C22 H22 0.9500 . ? C23 C24 1.385(2) . ? C23 H23 0.9500 . ? C24 C25 1.386(2) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 N2 104.45(10) . . ? N1 N2 C3 123.85(11) . . ? N1 N2 C7 112.90(10) . . ? C3 N2 C7 123.25(11) . . ? C4 C3 N2 118.36(12) . . ? C4 C3 H3 120.8 . . ? N2 C3 H3 120.8 . . ? C3 C4 C5 120.54(12) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 120.86(12) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 118.57(12) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? N2 C7 C8 105.43(11) . . ? N2 C7 C6 118.43(11) . . ? C8 C7 C6 136.13(12) . . ? C7 C8 C9 105.14(11) . . ? C7 C8 C10 124.43(11) . . ? C9 C8 C10 130.41(11) . . ? N1 C9 C8 112.08(11) . . ? N1 C9 C16 119.77(11) . . ? C8 C9 C16 128.09(11) . . ? N11 C10 C15 121.48(12) . . ? N11 C10 C8 115.86(11) . . ? C15 C10 C8 122.53(12) . . ? C10 N11 N12 118.33(11) . . ? N11 N12 C13 126.04(11) . . ? N11 N12 C19 113.13(10) . . ? C13 N12 C19 120.81(11) . . ? O13 C13 N12 121.28(12) . . ? O13 C13 C14 125.00(12) . . ? N12 C13 C14 113.71(11) . . ? C15 C14 C13 121.28(12) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C10 119.11(12) . . ? C14 C15 H15 120.4 . . ? C10 C15 H15 120.4 . . ? C9 C16 C17 112.24(11) . . ? C9 C16 C18 110.27(11) . . ? C17 C16 C18 110.31(12) . . ? C9 C16 H16 108.0 . . ? C17 C16 H16 108.0 . . ? C18 C16 H16 108.0 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N12 C19 C20 110.39(11) . . ? N12 C19 H19A 109.6 . . ? C20 C19 H19A 109.6 . . ? N12 C19 H19B 109.6 . . ? C20 C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? C21 C20 C25 119.27(13) . . ? C21 C20 C19 120.42(13) . . ? C25 C20 C19 120.30(12) . . ? C20 C21 C22 120.27(14) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C23 C22 C21 120.07(14) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 119.91(14) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C25 C24 C23 120.21(14) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C20 120.28(13) . . ? C24 C25 H25 119.9 . . ? C20 C25 H25 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 N2 C3 178.35(12) . . . . ? C9 N1 N2 C7 -0.88(14) . . . . ? N1 N2 C3 C4 -179.97(12) . . . . ? C7 N2 C3 C4 -0.82(19) . . . . ? N2 C3 C4 C5 0.7(2) . . . . ? C3 C4 C5 C6 -0.2(2) . . . . ? C4 C5 C6 C7 -0.1(2) . . . . ? N1 N2 C7 C8 0.92(14) . . . . ? C3 N2 C7 C8 -178.32(12) . . . . ? N1 N2 C7 C6 179.71(11) . . . . ? C3 N2 C7 C6 0.48(18) . . . . ? C5 C6 C7 N2 0.01(18) . . . . ? C5 C6 C7 C8 178.33(14) . . . . ? N2 C7 C8 C9 -0.55(14) . . . . ? C6 C7 C8 C9 -179.02(15) . . . . ? N2 C7 C8 C10 177.88(12) . . . . ? C6 C7 C8 C10 -0.6(2) . . . . ? N2 N1 C9 C8 0.50(15) . . . . ? N2 N1 C9 C16 177.89(11) . . . . ? C7 C8 C9 N1 0.04(15) . . . . ? C10 C8 C9 N1 -178.27(13) . . . . ? C7 C8 C9 C16 -177.09(13) . . . . ? C10 C8 C9 C16 4.6(2) . . . . ? C7 C8 C10 N11 37.01(18) . . . . ? C9 C8 C10 N11 -144.97(14) . . . . ? C7 C8 C10 C15 -138.84(13) . . . . ? C9 C8 C10 C15 39.2(2) . . . . ? C15 C10 N11 N12 0.03(18) . . . . ? C8 C10 N11 N12 -175.87(11) . . . . ? C10 N11 N12 C13 -2.06(19) . . . . ? C10 N11 N12 C19 176.60(12) . . . . ? N11 N12 C13 O13 -178.18(12) . . . . ? C19 N12 C13 O13 3.26(19) . . . . ? N11 N12 C13 C14 2.87(18) . . . . ? C19 N12 C13 C14 -175.69(12) . . . . ? O13 C13 C14 C15 179.30(13) . . . . ? N12 C13 C14 C15 -1.79(18) . . . . ? C13 C14 C15 C10 0.1(2) . . . . ? N11 C10 C15 C14 0.87(19) . . . . ? C8 C10 C15 C14 176.49(12) . . . . ? N1 C9 C16 C17 1.27(19) . . . . ? C8 C9 C16 C17 178.21(14) . . . . ? N1 C9 C16 C18 -122.15(14) . . . . ? C8 C9 C16 C18 54.79(18) . . . . ? N11 N12 C19 C20 -52.47(15) . . . . ? C13 N12 C19 C20 126.26(13) . . . . ? N12 C19 C20 C21 114.83(14) . . . . ? N12 C19 C20 C25 -63.73(16) . . . . ? C25 C20 C21 C22 -0.5(2) . . . . ? C19 C20 C21 C22 -179.10(13) . . . . ? C20 C21 C22 C23 0.7(2) . . . . ? C21 C22 C23 C24 -0.2(2) . . . . ? C22 C23 C24 C25 -0.6(2) . . . . ? C23 C24 C25 C20 0.8(2) . . . . ? C21 C20 C25 C24 -0.2(2) . . . . ? C19 C20 C25 C24 178.34(13) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.353 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.051