# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Vidal, Angel' _publ_contact_author_email vidal@um.es _publ_section_title ; Unprecedented intramolecular [3+2] cycloadditions azide-ketenimine and azide-carbodiimide. Synthesis of indolo[1,2-a]quinazolines and tetrazolo[5,1-b]quinazolines ; loop_ _publ_author_name M.Alajarin B.Bonillo M.-M.Ortin R.-A.Orenes A.Vidal # Attachment '4a.cif' data_moa155s _database_code_depnum_ccdc_archive 'CCDC 824784' #TrackingRef '4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H14 N2' _chemical_formula_weight 294.34 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 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.199(3) _cell_length_b 6.8079(8) _cell_length_c 16.539(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.390(2) _cell_angle_gamma 90.00 _cell_volume 2922.6(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4612 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9843 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details SADABS _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 'Bruker SMART APEX CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16225 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 28.20 _reflns_number_total 3398 _reflns_number_gt 3073 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0556P)^2^+2.1937P] 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 3398 _refine_ls_number_parameters 208 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1259 _refine_ls_wR_factor_gt 0.1222 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.142 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.04832(5) 0.23675(17) 0.03060(7) 0.0181(3) Uani 1 1 d . . . N2 N 0.04249(5) 0.27405(18) 0.17448(8) 0.0206(3) Uani 1 1 d . . . C1 C -0.08745(6) 0.3010(2) 0.02239(10) 0.0257(3) Uani 1 1 d D . . H1 H -0.1066 0.3224 0.0611 0.031 Uiso 1 1 calc R . . C2 C -0.11264(6) 0.2886(2) -0.06310(11) 0.0283(4) Uani 1 1 d D . . H2 H -0.1490 0.3021 -0.0836 0.034 Uiso 1 1 calc R . . C3 C -0.08426(6) 0.2561(2) -0.11893(10) 0.0286(4) Uani 1 1 d D . . H3 H -0.1018 0.2457 -0.1778 0.034 Uiso 1 1 calc R . . C4 C -0.03132(6) 0.2383(2) -0.09135(9) 0.0249(3) Uani 1 1 d D . . H4 H -0.0128 0.2167 -0.1309 0.030 Uiso 1 1 calc R . . C5 C -0.00509(6) 0.25234(19) -0.00463(9) 0.0190(3) Uani 1 1 d D . . C6 C -0.03377(5) 0.2823(2) 0.05259(9) 0.0213(3) Uani 1 1 d D . . C7 C 0.07117(5) 0.25024(19) 0.11968(8) 0.0174(3) Uani 1 1 d . . . C8 C -0.00712(5) 0.2896(2) 0.14172(9) 0.0225(3) Uani 1 1 d . . . H8 H -0.0272 0.3069 0.1794 0.027 Uiso 1 1 calc R . . C11 C 0.08781(5) 0.20537(19) -0.00584(9) 0.0187(3) Uani 1 1 d . . . C16 C 0.13474(5) 0.20123(19) 0.06079(9) 0.0181(3) Uani 1 1 d . . . C9 C 0.12377(5) 0.22854(19) 0.13932(9) 0.0176(3) Uani 1 1 d . . . C12 C 0.08723(6) 0.1779(2) -0.09015(9) 0.0249(3) Uani 1 1 d . . . H12 H 0.0558 0.1801 -0.1349 0.030 Uiso 1 1 calc R . . C13 C 0.13362(6) 0.1474(2) -0.10643(10) 0.0280(4) Uani 1 1 d . . . H13 H 0.1338 0.1251 -0.1630 0.034 Uiso 1 1 calc R . . C14 C 0.18029(6) 0.1487(2) -0.04138(10) 0.0251(3) Uani 1 1 d . . . H14 H 0.2117 0.1304 -0.0546 0.030 Uiso 1 1 calc R . . C15 C 0.18135(6) 0.1760(2) 0.04161(9) 0.0211(3) Uani 1 1 d . . . H15 H 0.2132 0.1777 0.0855 0.025 Uiso 1 1 calc R . . C21 C 0.16161(5) 0.2300(2) 0.22411(9) 0.0170(3) Uani 1 1 d D . . C22 C 0.20379(5) 0.1013(2) 0.24314(9) 0.0192(3) Uani 1 1 d D . . H22 H 0.2064 0.0077 0.2021 0.023 Uiso 1 1 calc R . . C23 C 0.24169(5) 0.1082(2) 0.32081(9) 0.0209(3) Uani 1 1 d D . . H23 H 0.2702 0.0210 0.3321 0.025 Uiso 1 1 calc R . . C24 C 0.23811(5) 0.2422(2) 0.38217(9) 0.0217(3) Uani 1 1 d D . . H24 H 0.2643 0.2483 0.4351 0.026 Uiso 1 1 calc R . . C25 C 0.19582(5) 0.3673(2) 0.36522(9) 0.0210(3) Uani 1 1 d D . . H25 H 0.1928 0.4571 0.4074 0.025 Uiso 1 1 calc R . . C26 C 0.15802(5) 0.3621(2) 0.28722(9) 0.0197(3) Uani 1 1 d D . . H26 H 0.1294 0.4489 0.2765 0.024 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 0.0199(6) 0.0183(6) 0.0159(6) 0.0000(4) 0.0052(5) 0.0006(4) N2 0.0191(6) 0.0236(6) 0.0209(6) -0.0011(5) 0.0088(5) -0.0011(5) C1 0.0199(7) 0.0209(7) 0.0354(8) 0.0028(6) 0.0069(6) -0.0006(6) C2 0.0182(7) 0.0217(7) 0.0387(9) 0.0052(6) -0.0010(6) -0.0014(6) C3 0.0288(8) 0.0232(8) 0.0257(8) 0.0034(6) -0.0042(6) -0.0026(6) C4 0.0264(8) 0.0230(7) 0.0221(7) 0.0007(6) 0.0026(6) 0.0003(6) C5 0.0198(7) 0.0135(6) 0.0218(7) 0.0016(5) 0.0033(5) -0.0009(5) C6 0.0197(7) 0.0179(7) 0.0257(7) 0.0018(5) 0.0058(6) -0.0017(5) C7 0.0187(7) 0.0170(6) 0.0166(6) -0.0002(5) 0.0053(5) -0.0009(5) C8 0.0187(7) 0.0266(7) 0.0246(7) -0.0008(6) 0.0099(6) -0.0018(6) C11 0.0219(7) 0.0150(6) 0.0205(7) 0.0010(5) 0.0082(6) 0.0009(5) C16 0.0224(7) 0.0140(6) 0.0193(7) 0.0004(5) 0.0086(5) 0.0007(5) C9 0.0196(7) 0.0157(6) 0.0185(7) -0.0001(5) 0.0074(5) 0.0004(5) C12 0.0312(8) 0.0250(7) 0.0184(7) 0.0006(6) 0.0072(6) 0.0010(6) C13 0.0417(9) 0.0269(8) 0.0206(7) -0.0003(6) 0.0173(7) 0.0018(7) C14 0.0299(8) 0.0222(7) 0.0297(8) 0.0009(6) 0.0185(6) 0.0023(6) C15 0.0229(7) 0.0183(7) 0.0248(7) 0.0009(6) 0.0111(6) 0.0014(5) C21 0.0159(6) 0.0180(6) 0.0183(6) 0.0008(5) 0.0068(5) -0.0024(5) C22 0.0207(7) 0.0186(7) 0.0207(7) -0.0004(5) 0.0100(5) 0.0008(5) C23 0.0171(7) 0.0235(7) 0.0230(7) 0.0043(6) 0.0075(5) 0.0024(5) C24 0.0178(7) 0.0277(8) 0.0189(7) 0.0020(6) 0.0043(5) -0.0042(6) C25 0.0217(7) 0.0230(7) 0.0198(7) -0.0036(5) 0.0082(6) -0.0031(5) C26 0.0191(7) 0.0191(7) 0.0223(7) -0.0005(5) 0.0082(5) 0.0005(5) _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 C11 1.3963(17) . ? N1 C5 1.3982(18) . ? N1 C7 1.4205(17) . ? N2 C8 1.2993(19) . ? N2 C7 1.3707(17) . ? C1 C2 1.377(2) . ? C1 C6 1.400(2) . ? C2 C3 1.387(2) . ? C3 C4 1.380(2) . ? C4 C5 1.401(2) . ? C5 C6 1.410(2) . ? C6 C8 1.436(2) . ? C7 C9 1.3772(19) . ? C11 C12 1.402(2) . ? C11 C16 1.415(2) . ? C16 C15 1.4063(19) . ? C16 C9 1.4291(18) . ? C9 C21 1.4708(19) . ? C12 C13 1.382(2) . ? C13 C14 1.397(2) . ? C14 C15 1.377(2) . ? C21 C22 1.4024(19) . ? C21 C26 1.4030(19) . ? C22 C23 1.387(2) . ? C23 C24 1.389(2) . ? C24 C25 1.391(2) . ? C25 C26 1.3892(19) . ? 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 C11 N1 C5 131.99(12) . . ? C11 N1 C7 107.64(11) . . ? C5 N1 C7 120.36(12) . . ? C8 N2 C7 117.33(12) . . ? C2 C1 C6 120.43(15) . . ? C1 C2 C3 119.21(14) . . ? C4 C3 C2 121.83(14) . . ? C3 C4 C5 119.63(15) . . ? N1 C5 C4 124.69(14) . . ? N1 C5 C6 116.46(13) . . ? C4 C5 C6 118.84(14) . . ? C1 C6 C5 120.05(14) . . ? C1 C6 C8 121.04(14) . . ? C5 C6 C8 118.90(13) . . ? N2 C7 C9 127.81(13) . . ? N2 C7 N1 122.31(12) . . ? C9 C7 N1 109.84(12) . . ? N2 C8 C6 124.61(13) . . ? N1 C11 C12 131.93(13) . . ? N1 C11 C16 107.34(12) . . ? C12 C11 C16 120.73(13) . . ? C15 C16 C11 119.39(13) . . ? C15 C16 C9 131.91(13) . . ? C11 C16 C9 108.69(12) . . ? C7 C9 C16 106.49(12) . . ? C7 C9 C21 127.29(12) . . ? C16 C9 C21 126.22(12) . . ? C13 C12 C11 118.30(14) . . ? C12 C13 C14 121.41(14) . . ? C15 C14 C13 120.80(14) . . ? C14 C15 C16 119.32(14) . . ? C22 C21 C26 117.88(13) . . ? C22 C21 C9 120.14(12) . . ? C26 C21 C9 121.95(12) . . ? C23 C22 C21 121.23(13) . . ? C22 C23 C24 120.26(13) . . ? C23 C24 C25 119.27(13) . . ? C26 C25 C24 120.65(13) . . ? C25 C26 C21 120.68(13) . . ? 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 C6 C1 C2 C3 0.4(2) . . . . ? C1 C2 C3 C4 -0.9(2) . . . . ? C2 C3 C4 C5 0.3(2) . . . . ? C11 N1 C5 C4 -0.1(2) . . . . ? C7 N1 C5 C4 -179.07(13) . . . . ? C11 N1 C5 C6 179.22(13) . . . . ? C7 N1 C5 C6 0.27(18) . . . . ? C3 C4 C5 N1 179.99(13) . . . . ? C3 C4 C5 C6 0.7(2) . . . . ? C2 C1 C6 C5 0.6(2) . . . . ? C2 C1 C6 C8 -178.26(13) . . . . ? N1 C5 C6 C1 179.52(12) . . . . ? C4 C5 C6 C1 -1.1(2) . . . . ? N1 C5 C6 C8 -1.63(19) . . . . ? C4 C5 C6 C8 177.76(13) . . . . ? C8 N2 C7 C9 -179.22(14) . . . . ? C8 N2 C7 N1 -1.9(2) . . . . ? C11 N1 C7 N2 -177.63(12) . . . . ? C5 N1 C7 N2 1.55(19) . . . . ? C11 N1 C7 C9 0.15(15) . . . . ? C5 N1 C7 C9 179.33(12) . . . . ? C7 N2 C8 C6 0.4(2) . . . . ? C1 C6 C8 N2 -179.77(14) . . . . ? C5 C6 C8 N2 1.4(2) . . . . ? C5 N1 C11 C12 -0.4(3) . . . . ? C7 N1 C11 C12 178.67(15) . . . . ? C5 N1 C11 C16 -179.49(13) . . . . ? C7 N1 C11 C16 -0.44(14) . . . . ? N1 C11 C16 C15 -178.56(12) . . . . ? C12 C11 C16 C15 2.2(2) . . . . ? N1 C11 C16 C9 0.58(15) . . . . ? C12 C11 C16 C9 -178.66(13) . . . . ? N2 C7 C9 C16 177.83(13) . . . . ? N1 C7 C9 C16 0.20(15) . . . . ? N2 C7 C9 C21 -1.4(2) . . . . ? N1 C7 C9 C21 -179.01(12) . . . . ? C15 C16 C9 C7 178.51(14) . . . . ? C11 C16 C9 C7 -0.48(15) . . . . ? C15 C16 C9 C21 -2.3(2) . . . . ? C11 C16 C9 C21 178.74(12) . . . . ? N1 C11 C12 C13 -179.25(15) . . . . ? C16 C11 C12 C13 -0.2(2) . . . . ? C11 C12 C13 C14 -1.6(2) . . . . ? C12 C13 C14 C15 1.5(2) . . . . ? C13 C14 C15 C16 0.5(2) . . . . ? C11 C16 C15 C14 -2.3(2) . . . . ? C9 C16 C15 C14 178.78(14) . . . . ? C7 C9 C21 C22 141.47(14) . . . . ? C16 C9 C21 C22 -37.6(2) . . . . ? C7 C9 C21 C26 -40.6(2) . . . . ? C16 C9 C21 C26 140.31(14) . . . . ? C26 C21 C22 C23 -2.1(2) . . . . ? C9 C21 C22 C23 175.94(12) . . . . ? C21 C22 C23 C24 0.9(2) . . . . ? C22 C23 C24 C25 0.8(2) . . . . ? C23 C24 C25 C26 -1.4(2) . . . . ? C24 C25 C26 C21 0.3(2) . . . . ? C22 C21 C26 C25 1.4(2) . . . . ? C9 C21 C26 C25 -176.51(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C8 H8 N2 0.95 2.58 3.4535(19) 152.6 2 _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.284 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.061 # Attachment '12.cif' data_bbf191s _database_code_depnum_ccdc_archive 'CCDC 824785' #TrackingRef '12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H34 Cl2 N4 O2' _chemical_formula_weight 709.64 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 Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.4794(8) _cell_length_b 12.5963(5) _cell_length_c 13.9210(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.538(2) _cell_angle_gamma 90.00 _cell_volume 3377.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7804 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 27.90 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 0.239 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9472 _exptl_absorpt_correction_T_max 0.9812 _exptl_absorpt_process_details SADABS _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 'Bruker SMART APEX CCD' _diffrn_measurement_method \W-scan _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19216 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28.23 _reflns_number_total 3922 _reflns_number_gt 3522 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0747P)^2^+6.4256P] 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 'OH free, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3922 _refine_ls_number_parameters 235 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1424 _refine_ls_wR_factor_gt 0.1384 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 0.42403(7) 0.88643(11) 0.33784(9) 0.0154(3) Uani 1 1 d . . . N2 N 0.51749(7) 0.76665(11) 0.37993(9) 0.0157(3) Uani 1 1 d . . . O1 O 0.41854(6) 0.63127(9) 0.24718(9) 0.0186(3) Uani 1 1 d . . . H01 H 0.4368(12) 0.6672(19) 0.2060(17) 0.029(6) Uiso 1 1 d . . . C1 C 0.58413(9) 1.04331(14) 0.42345(12) 0.0207(3) Uani 1 1 d . . . H1 H 0.5693 1.1149 0.4137 0.025 Uiso 1 1 calc R . . C2 C 0.65209(9) 1.02204(14) 0.46396(13) 0.0233(4) Uani 1 1 d . . . H2 H 0.6836 1.0789 0.4811 0.028 Uiso 1 1 calc R . . C3 C 0.67434(9) 0.91776(15) 0.47955(12) 0.0217(4) Uani 1 1 d . . . H3 H 0.7206 0.9033 0.5088 0.026 Uiso 1 1 calc R . . C4 C 0.62867(9) 0.83493(14) 0.45218(12) 0.0190(3) Uani 1 1 d . . . H4 H 0.6440 0.7637 0.4625 0.023 Uiso 1 1 calc R . . C5 C 0.56027(8) 0.85538(12) 0.40954(11) 0.0156(3) Uani 1 1 d . . . C6 C 0.53714(8) 0.96082(13) 0.39674(11) 0.0163(3) Uani 1 1 d . . . C7 C 0.46242(8) 0.98542(12) 0.35619(11) 0.0164(3) Uani 1 1 d . . . H7A H 0.4413 1.0291 0.4031 0.020 Uiso 1 1 calc R . . H7B H 0.4605 1.0261 0.2950 0.020 Uiso 1 1 calc R . . C8 C 0.45377(8) 0.78847(12) 0.34762(11) 0.0143(3) Uani 1 1 d . . . C9 C 0.39745(8) 0.70409(12) 0.31440(11) 0.0152(3) Uani 1 1 d . . . C11 C 0.33665(8) 0.77433(13) 0.27365(11) 0.0164(3) Uani 1 1 d . . . C12 C 0.35476(8) 0.88022(13) 0.29185(11) 0.0159(3) Uani 1 1 d . . . C13 C 0.30902(9) 0.96281(14) 0.26516(12) 0.0200(3) Uani 1 1 d . . . H13 H 0.3219 1.0346 0.2787 0.024 Uiso 1 1 calc R . . C14 C 0.24312(9) 0.93596(15) 0.21739(12) 0.0236(4) Uani 1 1 d . . . H14 H 0.2104 0.9907 0.1980 0.028 Uiso 1 1 calc R . . C15 C 0.22443(9) 0.83090(15) 0.19774(12) 0.0236(4) Uani 1 1 d . . . H15 H 0.1794 0.8146 0.1647 0.028 Uiso 1 1 calc R . . C16 C 0.27149(9) 0.74886(14) 0.22633(12) 0.0208(4) Uani 1 1 d . . . H16 H 0.2588 0.6769 0.2134 0.025 Uiso 1 1 calc R . . C21 C 0.38314(8) 0.64222(13) 0.40431(11) 0.0167(3) Uani 1 1 d D . . C22 C 0.41519(9) 0.54473(14) 0.42641(13) 0.0216(4) Uani 1 1 d D . . H22 H 0.4454 0.5161 0.3853 0.026 Uiso 1 1 calc R . . C23 C 0.40303(9) 0.48900(15) 0.50882(14) 0.0261(4) Uani 1 1 d D . . H23 H 0.4244 0.4219 0.5231 0.031 Uiso 1 1 calc R . . C24 C 0.35994(9) 0.53099(16) 0.56994(14) 0.0276(4) Uani 1 1 d D . . H24 H 0.3515 0.4926 0.6257 0.033 Uiso 1 1 calc R . . C25 C 0.32912(9) 0.62954(16) 0.54935(13) 0.0264(4) Uani 1 1 d D . . H25 H 0.3005 0.6595 0.5919 0.032 Uiso 1 1 calc R . . C26 C 0.34028(9) 0.68409(14) 0.46610(12) 0.0213(3) Uani 1 1 d D . . H26 H 0.3183 0.7507 0.4514 0.026 Uiso 1 1 calc R . . C99 C 0.5000 0.6386(3) 0.7500 0.0483(9) Uani 1 2 d S . . H99A H 0.4607 0.5922 0.7235 0.058 Uiso 0.50 1 calc PR . . H99B H 0.5393 0.5922 0.7765 0.058 Uiso 0.50 1 calc PR . . Cl1 Cl 0.47537(3) 0.71475(5) 0.84581(7) 0.0622(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0147(6) 0.0136(6) 0.0171(6) -0.0007(5) 0.0001(5) -0.0002(5) N2 0.0162(6) 0.0145(6) 0.0157(6) -0.0004(5) 0.0004(5) -0.0011(5) O1 0.0235(6) 0.0141(5) 0.0184(6) -0.0032(4) 0.0035(5) -0.0035(4) C1 0.0247(8) 0.0176(8) 0.0204(8) -0.0041(6) 0.0054(6) -0.0035(6) C2 0.0227(8) 0.0249(9) 0.0224(8) -0.0081(7) 0.0038(6) -0.0092(7) C3 0.0162(7) 0.0298(9) 0.0185(8) -0.0045(7) 0.0011(6) -0.0027(7) C4 0.0195(8) 0.0208(8) 0.0165(7) -0.0020(6) 0.0022(6) 0.0000(6) C5 0.0173(8) 0.0166(7) 0.0131(7) -0.0025(5) 0.0025(6) -0.0024(6) C6 0.0186(7) 0.0175(8) 0.0130(7) -0.0027(6) 0.0033(6) -0.0028(6) C7 0.0204(8) 0.0121(7) 0.0168(7) -0.0017(6) 0.0027(6) -0.0016(6) C8 0.0188(8) 0.0125(7) 0.0118(7) -0.0003(5) 0.0023(5) -0.0011(6) C9 0.0149(7) 0.0140(7) 0.0161(7) -0.0006(6) 0.0005(6) -0.0020(6) C11 0.0178(8) 0.0172(7) 0.0138(7) 0.0030(6) 0.0012(6) -0.0003(6) C12 0.0160(7) 0.0183(8) 0.0132(7) 0.0006(6) 0.0014(5) -0.0005(6) C13 0.0210(8) 0.0192(8) 0.0199(8) 0.0013(6) 0.0031(6) 0.0026(6) C14 0.0205(8) 0.0285(9) 0.0211(8) 0.0060(7) 0.0011(6) 0.0068(7) C15 0.0158(8) 0.0334(10) 0.0204(8) 0.0051(7) -0.0018(6) -0.0018(7) C16 0.0197(8) 0.0222(8) 0.0196(8) 0.0027(6) 0.0000(6) -0.0045(6) C21 0.0147(7) 0.0164(7) 0.0174(7) 0.0022(6) -0.0032(6) -0.0045(6) C22 0.0179(8) 0.0189(8) 0.0268(9) 0.0036(7) -0.0002(6) 0.0001(6) C23 0.0215(8) 0.0228(9) 0.0318(9) 0.0110(7) -0.0037(7) -0.0004(7) C24 0.0206(8) 0.0349(10) 0.0259(9) 0.0150(8) -0.0012(7) -0.0054(7) C25 0.0213(8) 0.0355(10) 0.0223(8) 0.0077(7) 0.0035(7) 0.0013(7) C26 0.0219(8) 0.0212(8) 0.0205(8) 0.0044(6) 0.0019(6) 0.0013(7) C99 0.056(2) 0.0274(15) 0.055(2) 0.000 -0.0144(17) 0.000 Cl1 0.0415(4) 0.0361(3) 0.1113(6) -0.0229(3) 0.0189(4) -0.0128(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 C8 1.361(2) . ? N1 C12 1.407(2) . ? N1 C7 1.457(2) . ? N2 C8 1.286(2) . ? N2 C5 1.418(2) . ? O1 C9 1.4143(19) . ? C1 C2 1.386(3) . ? C1 C6 1.398(2) . ? C2 C3 1.390(3) . ? C3 C4 1.387(2) . ? C4 C5 1.400(2) . ? C5 C6 1.405(2) . ? C6 C7 1.513(2) . ? C8 C9 1.548(2) . ? C9 C11 1.519(2) . ? C9 C21 1.535(2) . ? C11 C16 1.378(2) . ? C11 C12 1.393(2) . ? C12 C13 1.384(2) . ? C13 C14 1.397(2) . ? C14 C15 1.389(3) . ? C15 C16 1.399(2) . ? C21 C26 1.389(2) . ? C21 C22 1.391(2) . ? C22 C23 1.395(2) . ? C23 C24 1.386(3) . ? C24 C25 1.390(3) . ? C25 C26 1.392(2) . ? C99 Cl1 1.7661(19) . ? C99 Cl1 1.7662(19) 2_656 ? 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 C8 N1 C12 111.11(13) . . ? C8 N1 C7 123.95(13) . . ? C12 N1 C7 124.05(13) . . ? C8 N2 C5 115.36(13) . . ? C2 C1 C6 120.84(16) . . ? C1 C2 C3 120.20(16) . . ? C4 C3 C2 119.70(16) . . ? C3 C4 C5 120.61(16) . . ? C4 C5 C6 119.66(14) . . ? C4 C5 N2 117.35(14) . . ? C6 C5 N2 122.98(14) . . ? C1 C6 C5 118.93(15) . . ? C1 C6 C7 120.17(15) . . ? C5 C6 C7 120.90(14) . . ? N1 C7 C6 109.30(13) . . ? N2 C8 N1 127.10(14) . . ? N2 C8 C9 124.22(14) . . ? N1 C8 C9 108.68(13) . . ? O1 C9 C11 114.69(13) . . ? O1 C9 C21 108.43(13) . . ? C11 C9 C21 111.99(13) . . ? O1 C9 C8 112.35(12) . . ? C11 C9 C8 100.96(12) . . ? C21 C9 C8 108.15(12) . . ? C16 C11 C12 120.01(15) . . ? C16 C11 C9 130.87(15) . . ? C12 C11 C9 109.12(13) . . ? C13 C12 C11 122.36(15) . . ? C13 C12 N1 128.02(15) . . ? C11 C12 N1 109.61(14) . . ? C12 C13 C14 117.08(16) . . ? C15 C14 C13 121.33(16) . . ? C14 C15 C16 120.40(16) . . ? C11 C16 C15 118.81(16) . . ? C26 C21 C22 119.31(15) . . ? C26 C21 C9 120.74(14) . . ? C22 C21 C9 119.91(15) . . ? C21 C22 C23 120.04(17) . . ? C24 C23 C22 120.35(17) . . ? C23 C24 C25 119.78(16) . . ? C24 C25 C26 119.77(17) . . ? C21 C26 C25 120.72(16) . . ? Cl1 C99 Cl1 114.20(19) . 2_656 ? 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 C6 C1 C2 C3 -0.7(3) . . . . ? C1 C2 C3 C4 1.6(3) . . . . ? C2 C3 C4 C5 -0.4(2) . . . . ? C3 C4 C5 C6 -1.7(2) . . . . ? C3 C4 C5 N2 177.52(14) . . . . ? C8 N2 C5 C4 175.18(14) . . . . ? C8 N2 C5 C6 -5.6(2) . . . . ? C2 C1 C6 C5 -1.4(2) . . . . ? C2 C1 C6 C7 177.65(15) . . . . ? C4 C5 C6 C1 2.6(2) . . . . ? N2 C5 C6 C1 -176.59(14) . . . . ? C4 C5 C6 C7 -176.47(14) . . . . ? N2 C5 C6 C7 4.3(2) . . . . ? C8 N1 C7 C6 -5.7(2) . . . . ? C12 N1 C7 C6 -173.97(13) . . . . ? C1 C6 C7 N1 -177.82(14) . . . . ? C5 C6 C7 N1 1.2(2) . . . . ? C5 N2 C8 N1 1.0(2) . . . . ? C5 N2 C8 C9 -178.02(13) . . . . ? C12 N1 C8 N2 174.65(15) . . . . ? C7 N1 C8 N2 5.1(2) . . . . ? C12 N1 C8 C9 -6.20(17) . . . . ? C7 N1 C8 C9 -175.78(13) . . . . ? N2 C8 C9 O1 -51.0(2) . . . . ? N1 C8 C9 O1 129.81(13) . . . . ? N2 C8 C9 C11 -173.66(15) . . . . ? N1 C8 C9 C11 7.15(15) . . . . ? N2 C8 C9 C21 68.64(19) . . . . ? N1 C8 C9 C21 -110.55(14) . . . . ? O1 C9 C11 C16 54.1(2) . . . . ? C21 C9 C11 C16 -70.0(2) . . . . ? C8 C9 C11 C16 175.10(17) . . . . ? O1 C9 C11 C12 -126.77(14) . . . . ? C21 C9 C11 C12 109.12(15) . . . . ? C8 C9 C11 C12 -5.75(16) . . . . ? C16 C11 C12 C13 0.9(2) . . . . ? C9 C11 C12 C13 -178.38(14) . . . . ? C16 C11 C12 N1 -178.16(14) . . . . ? C9 C11 C12 N1 2.58(18) . . . . ? C8 N1 C12 C13 -176.60(15) . . . . ? C7 N1 C12 C13 -7.0(3) . . . . ? C8 N1 C12 C11 2.38(18) . . . . ? C7 N1 C12 C11 171.95(14) . . . . ? C11 C12 C13 C14 -0.8(2) . . . . ? N1 C12 C13 C14 178.09(15) . . . . ? C12 C13 C14 C15 0.1(3) . . . . ? C13 C14 C15 C16 0.5(3) . . . . ? C12 C11 C16 C15 -0.3(2) . . . . ? C9 C11 C16 C15 178.81(16) . . . . ? C14 C15 C16 C11 -0.4(3) . . . . ? O1 C9 C21 C26 -157.82(14) . . . . ? C11 C9 C21 C26 -30.3(2) . . . . ? C8 C9 C21 C26 80.10(18) . . . . ? O1 C9 C21 C22 24.42(19) . . . . ? C11 C9 C21 C22 151.96(14) . . . . ? C8 C9 C21 C22 -97.66(16) . . . . ? C26 C21 C22 C23 1.3(2) . . . . ? C9 C21 C22 C23 179.12(15) . . . . ? C21 C22 C23 C24 -1.0(3) . . . . ? C22 C23 C24 C25 -0.5(3) . . . . ? C23 C24 C25 C26 1.7(3) . . . . ? C22 C21 C26 C25 -0.1(2) . . . . ? C9 C21 C26 C25 -177.88(15) . . . . ? C24 C25 C26 C21 -1.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H01 N2 0.85(2) 2.03(3) 2.8717(18) 173(2) 2_655 C24 H24 O1 0.95 2.52 3.276(2) 136.8 6_566 C1 H1 Cl1 0.95 2.89 3.7768(19) 156.5 6_575 _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.815 _refine_diff_density_min -0.766 _refine_diff_density_rms 0.070