Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is (C) The Royal Society of Chemistry data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name 'Otto Meth-Cohn' 'Ying Cheng' 'Hua Yang' _publ_contact_author_name 'Prof Otto Meth-Cohn' _publ_contact_author_address ; Chemistry - home address below: Sunderland University 10 Crofts Park Hepscott Morpeth NE61 6LJ UNITED KINGDOM ; _publ_contact_author_email OTTO.METH-COHN@SUNDERLAND.AC.UK _publ_section_title ; The surprising nucleophilic addition of aminochlorocarbenes to diethylacetylenedicarboxylate and to oxalyl chloride: Quinolines and benzo[1,4]diazepines from N-alkylformanilides and oxalyl chloride in the presence of H=FCnig's base ; data_050702a _database_code_CSD 195706 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7-Fluoro-4-(4-fluorophenyl)-1-methylbenzo[f][1,4]diazepine-2,3-dicarboxylic anhydride ; _chemical_name_common ? _chemical_formula_sum 'C18 H12 F2 N2 O3 ' _chemical_formula_moiety '? ' _chemical_melting_point 481 _chemical_formula_weight 342.30 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 15.752(6) _cell_length_b 11.767(4) _cell_length_c 8.688(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.607(7) _cell_angle_gamma 90.00 _cell_volume 1565.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour Red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9660 _exptl_absorpt_correction_T_max 0.9942 _exptl_absorpt_process_details SADABS _exptl_special_details ; Crystallization solvent Ethyl acetate ; _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 '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 6550 _diffrn_reflns_av_R_equivalents 0.1421 _diffrn_reflns_av_sigmaI/netI 0.2361 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2883 _reflns_number_gt 818 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0603P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2883 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2534 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1883 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 0.932 _refine_ls_restrained_S_all 0.932 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.9039(2) 0.5808(4) 0.1231(4) 0.0860(14) Uani 1 1 d . . . F2 F 0.9334(3) 0.2180(4) 0.8133(7) 0.147(2) Uani 1 1 d . . . N1 N 0.7475(3) 0.6268(4) 0.6246(6) 0.0404(13) Uani 1 1 d . . . N2 N 0.6366(3) 0.4680(4) 0.7894(6) 0.0501(15) Uani 1 1 d . . . O1 O 0.4552(3) 0.5628(4) 0.6739(5) 0.0763(16) Uani 1 1 d . . . O2 O 0.5157(3) 0.6853(4) 0.5355(5) 0.0637(13) Uani 1 1 d . . . O3 O 0.6136(3) 0.7835(4) 0.4396(5) 0.0753(16) Uani 1 1 d . . . C1 C 0.5203(5) 0.5965(6) 0.6396(8) 0.0527(18) Uani 1 1 d . . . C2 C 0.6113(4) 0.5568(5) 0.6871(7) 0.0418(16) Uani 1 1 d . . . C3 C 0.6590(4) 0.6213(5) 0.6064(6) 0.0387(16) Uani 1 1 d . . . C4 C 0.6003(5) 0.7054(7) 0.5161(8) 0.0558(19) Uani 1 1 d . . . C5 C 0.7866(4) 0.6156(4) 0.4946(7) 0.0375(15) Uani 1 1 d . . . C6 C 0.7386(4) 0.5871(5) 0.3462(7) 0.0485(17) Uani 1 1 d . . . H6A H 0.6788 0.5745 0.3299 0.058 Uiso 1 1 calc R . . C7 C 0.7782(4) 0.5773(5) 0.2212(7) 0.0559(18) Uani 1 1 d . . . H7A H 0.7454 0.5595 0.1204 0.067 Uiso 1 1 calc R . . C8 C 0.8652(4) 0.5936(6) 0.2472(8) 0.0569(19) Uani 1 1 d . . . C9 C 0.9139(4) 0.6230(6) 0.3901(8) 0.066(2) Uani 1 1 d . . . H9A H 0.9736 0.6353 0.4052 0.079 Uiso 1 1 calc R . . C10 C 0.8738(4) 0.6345(6) 0.5136(7) 0.0566(19) Uani 1 1 d . . . H10A H 0.9070 0.6558 0.6126 0.068 Uiso 1 1 calc R . . C11 C 0.7950(4) 0.5866(5) 0.7819(6) 0.0454(17) Uani 1 1 d . . . H11A H 0.7693 0.6203 0.8623 0.054 Uiso 1 1 calc R . . H11B H 0.8553 0.6113 0.8015 0.054 Uiso 1 1 calc R . . C12 C 0.7921(4) 0.4603(6) 0.7942(6) 0.0465(17) Uani 1 1 d . . . C13 C 0.8656(5) 0.3967(8) 0.7994(7) 0.068(2) Uani 1 1 d . . . H13A H 0.9177 0.4325 0.7950 0.082 Uiso 1 1 calc R . . C14 C 0.8629(6) 0.2829(10) 0.8107(10) 0.096(3) Uani 1 1 d . . . C15 C 0.7893(7) 0.2276(7) 0.8154(10) 0.099(3) Uani 1 1 d . . . H15A H 0.7895 0.1487 0.8226 0.118 Uiso 1 1 calc R . . C16 C 0.7138(5) 0.2867(7) 0.8095(8) 0.079(2) Uani 1 1 d . . . H16A H 0.6628 0.2489 0.8154 0.094 Uiso 1 1 calc R . . C17 C 0.7148(4) 0.4055(6) 0.7946(7) 0.0500(17) Uani 1 1 d . . . C18 C 0.5799(4) 0.4311(6) 0.8915(8) 0.079(2) Uani 1 1 d . . . H18A H 0.5301 0.4805 0.8764 0.119 Uiso 1 1 calc R . . H18B H 0.6118 0.4341 1.0002 0.119 Uiso 1 1 calc R . . H18C H 0.5607 0.3546 0.8648 0.119 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 F1 0.074(3) 0.141(4) 0.055(3) -0.007(2) 0.037(2) -0.005(3) F2 0.097(4) 0.116(4) 0.219(6) 0.019(4) 0.019(4) 0.060(3) N1 0.036(3) 0.049(4) 0.036(4) 0.002(2) 0.010(3) -0.004(3) N2 0.056(4) 0.044(4) 0.059(4) 0.008(3) 0.032(3) -0.010(3) O1 0.051(3) 0.087(4) 0.097(4) -0.019(3) 0.031(3) -0.011(3) O2 0.058(3) 0.062(4) 0.069(3) -0.003(3) 0.013(3) 0.018(3) O3 0.084(4) 0.065(4) 0.076(4) 0.029(3) 0.019(3) 0.012(3) C1 0.056(5) 0.046(5) 0.057(5) -0.021(4) 0.016(4) 0.002(4) C2 0.038(4) 0.048(5) 0.043(4) -0.013(3) 0.015(3) -0.002(3) C3 0.049(5) 0.042(4) 0.025(4) -0.003(3) 0.009(3) 0.004(4) C4 0.053(5) 0.062(6) 0.052(5) -0.009(4) 0.011(4) 0.000(4) C5 0.048(4) 0.035(4) 0.033(4) 0.002(3) 0.017(3) -0.001(3) C6 0.045(4) 0.061(5) 0.040(4) 0.001(3) 0.012(4) -0.006(3) C7 0.060(5) 0.077(5) 0.030(4) -0.003(3) 0.009(4) -0.001(4) C8 0.048(5) 0.076(5) 0.051(5) 0.002(4) 0.022(4) 0.001(4) C9 0.039(4) 0.113(7) 0.047(5) 0.000(4) 0.011(4) -0.011(4) C10 0.043(4) 0.096(6) 0.034(4) -0.008(3) 0.015(3) -0.016(4) C11 0.044(4) 0.058(5) 0.033(4) 0.001(3) 0.008(3) -0.012(3) C12 0.047(4) 0.054(5) 0.039(4) 0.002(3) 0.009(3) -0.007(4) C13 0.054(6) 0.079(7) 0.067(5) 0.012(4) 0.008(4) 0.013(5) C14 0.062(7) 0.097(9) 0.125(8) 0.012(6) 0.012(6) 0.020(7) C15 0.108(8) 0.048(6) 0.133(8) 0.008(5) 0.014(6) 0.036(6) C16 0.083(7) 0.053(6) 0.097(6) 0.007(4) 0.018(5) -0.015(5) C17 0.054(5) 0.050(5) 0.048(4) 0.006(3) 0.017(3) 0.008(4) C18 0.077(5) 0.084(6) 0.089(6) 0.016(4) 0.043(4) -0.018(4) _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 F1 C8 1.366(7) . ? F2 C14 1.343(9) . ? N1 C3 1.366(6) . ? N1 C5 1.415(7) . ? N1 C11 1.473(6) . ? N2 C2 1.369(7) . ? N2 C17 1.426(7) . ? N2 C18 1.464(7) . ? O1 C1 1.200(7) . ? O2 C1 1.373(7) . ? O2 C4 1.401(7) . ? O3 C4 1.182(7) . ? C1 C2 1.472(8) . ? C2 C3 1.371(7) . ? C3 C4 1.452(8) . ? C5 C10 1.363(7) . ? C5 C6 1.375(7) . ? C6 C7 1.378(7) . ? C6 H6A 0.9300 . ? C7 C8 1.350(8) . ? C7 H7A 0.9300 . ? C8 C9 1.342(8) . ? C9 C10 1.373(7) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C12 1.492(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.371(8) . ? C12 C17 1.379(8) . ? C13 C14 1.345(10) . ? C13 H13A 0.9300 . ? C14 C15 1.338(10) . ? C15 C16 1.368(9) . ? C15 H15A 0.9300 . ? C16 C17 1.404(8) . ? C16 H16A 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 C5 121.8(5) . . ? C3 N1 C11 111.9(5) . . ? C5 N1 C11 119.3(5) . . ? C2 N2 C17 122.1(5) . . ? C2 N2 C18 119.6(5) . . ? C17 N2 C18 118.3(5) . . ? C1 O2 C4 107.7(5) . . ? O1 C1 O2 120.0(7) . . ? O1 C1 C2 131.1(7) . . ? O2 C1 C2 108.8(6) . . ? N2 C2 C3 130.1(6) . . ? N2 C2 C1 122.7(6) . . ? C3 C2 C1 107.2(6) . . ? N1 C3 C2 129.3(6) . . ? N1 C3 C4 122.2(6) . . ? C2 C3 C4 107.3(6) . . ? O3 C4 O2 119.9(7) . . ? O3 C4 C3 131.2(7) . . ? O2 C4 C3 108.8(6) . . ? C10 C5 C6 118.1(5) . . ? C10 C5 N1 120.3(6) . . ? C6 C5 N1 121.6(6) . . ? C5 C6 C7 120.5(6) . . ? C5 C6 H6A 119.7 . . ? C7 C6 H6A 119.7 . . ? C8 C7 C6 119.1(6) . . ? C8 C7 H7A 120.4 . . ? C6 C7 H7A 120.4 . . ? C9 C8 C7 121.9(7) . . ? C9 C8 F1 119.6(6) . . ? C7 C8 F1 118.5(6) . . ? C8 C9 C10 118.7(6) . . ? C8 C9 H9A 120.6 . . ? C10 C9 H9A 120.6 . . ? C5 C10 C9 121.6(6) . . ? C5 C10 H10A 119.2 . . ? C9 C10 H10A 119.2 . . ? N1 C11 C12 111.7(4) . . ? N1 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? N1 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? C13 C12 C17 119.0(6) . . ? C13 C12 C11 120.4(7) . . ? C17 C12 C11 120.5(6) . . ? C14 C13 C12 120.3(8) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C15 C14 F2 116.2(10) . . ? C15 C14 C13 122.0(9) . . ? F2 C14 C13 121.8(9) . . ? C14 C15 C16 120.2(8) . . ? C14 C15 H15A 119.9 . . ? C16 C15 H15A 119.9 . . ? C15 C16 C17 118.7(7) . . ? C15 C16 H16A 120.6 . . ? C17 C16 H16A 120.6 . . ? C12 C17 C16 119.7(6) . . ? C12 C17 N2 121.0(6) . . ? C16 C17 N2 119.2(7) . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 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 C4 O2 C1 O1 -179.2(6) . . . . ? C4 O2 C1 C2 -0.9(6) . . . . ? C17 N2 C2 C3 -18.8(10) . . . . ? C18 N2 C2 C3 164.5(6) . . . . ? C17 N2 C2 C1 158.4(5) . . . . ? C18 N2 C2 C1 -18.3(8) . . . . ? O1 C1 C2 N2 -1.2(10) . . . . ? O2 C1 C2 N2 -179.3(5) . . . . ? O1 C1 C2 C3 176.5(7) . . . . ? O2 C1 C2 C3 -1.6(6) . . . . ? C5 N1 C3 C2 129.3(6) . . . . ? C11 N1 C3 C2 -21.2(8) . . . . ? C5 N1 C3 C4 -64.8(7) . . . . ? C11 N1 C3 C4 144.8(5) . . . . ? N2 C2 C3 N1 -11.7(11) . . . . ? C1 C2 C3 N1 170.8(5) . . . . ? N2 C2 C3 C4 -179.2(6) . . . . ? C1 C2 C3 C4 3.3(6) . . . . ? C1 O2 C4 O3 -174.8(6) . . . . ? C1 O2 C4 C3 2.9(6) . . . . ? N1 C3 C4 O3 4.8(11) . . . . ? C2 C3 C4 O3 173.4(7) . . . . ? N1 C3 C4 O2 -172.6(5) . . . . ? C2 C3 C4 O2 -3.9(7) . . . . ? C3 N1 C5 C10 172.4(5) . . . . ? C11 N1 C5 C10 -39.2(8) . . . . ? C3 N1 C5 C6 -6.6(8) . . . . ? C11 N1 C5 C6 141.8(5) . . . . ? C10 C5 C6 C7 0.6(9) . . . . ? N1 C5 C6 C7 179.7(5) . . . . ? C5 C6 C7 C8 1.3(9) . . . . ? C6 C7 C8 C9 -2.2(10) . . . . ? C6 C7 C8 F1 178.4(5) . . . . ? C7 C8 C9 C10 1.2(11) . . . . ? F1 C8 C9 C10 -179.5(6) . . . . ? C6 C5 C10 C9 -1.7(10) . . . . ? N1 C5 C10 C9 179.2(6) . . . . ? C8 C9 C10 C5 0.8(11) . . . . ? C3 N1 C11 C12 74.9(6) . . . . ? C5 N1 C11 C12 -76.4(6) . . . . ? N1 C11 C12 C13 108.9(6) . . . . ? N1 C11 C12 C17 -68.6(7) . . . . ? C17 C12 C13 C14 -2.5(10) . . . . ? C11 C12 C13 C14 179.9(7) . . . . ? C12 C13 C14 C15 0.9(13) . . . . ? C12 C13 C14 F2 178.8(7) . . . . ? F2 C14 C15 C16 -178.5(7) . . . . ? C13 C14 C15 C16 -0.4(14) . . . . ? C14 C15 C16 C17 1.6(12) . . . . ? C13 C12 C17 C16 3.7(9) . . . . ? C11 C12 C17 C16 -178.7(5) . . . . ? C13 C12 C17 N2 180.0(5) . . . . ? C11 C12 C17 N2 -2.5(8) . . . . ? C15 C16 C17 C12 -3.3(10) . . . . ? C15 C16 C17 N2 -179.6(6) . . . . ? C2 N2 C17 C12 45.3(8) . . . . ? C18 N2 C17 C12 -138.0(6) . . . . ? C2 N2 C17 C16 -138.4(6) . . . . ? C18 N2 C17 C16 38.3(8) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.183 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.055 data_050702b _database_code_CSD 195707 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Diethyl 2-(2-chloro-1,2-bis(ethoxy-carbonyl)vinyl)- 6-methoxy1-1-methyl-1,2-dihydroquinoline-3,4-dicarboxylate ; _chemical_melting_point 378 _chemical_formula_moiety ? _chemical_formula_sum 'C25 H30 Cl N O9' _chemical_formula_weight 523.95 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 8.312(12) _cell_length_b 8.487(13) _cell_length_c 19.91(3) _cell_angle_alpha 78.19(3) _cell_angle_beta 81.52(3) _cell_angle_gamma 88.99(3) _cell_volume 1360(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour Red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.191 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9629 _exptl_absorpt_correction_T_max 0.9905 _exptl_absorpt_process_details SADABS _exptl_special_details ; Crystallization solvent Ethyl acetate ; _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 '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 4331 _diffrn_reflns_av_R_equivalents 0.1060 _diffrn_reflns_av_sigmaI/netI 0.1181 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3760 _reflns_number_gt 1667 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3760 _refine_ls_number_parameters 325 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1848 _refine_ls_R_factor_gt 0.0803 _refine_ls_wR_factor_ref 0.2216 _refine_ls_wR_factor_gt 0.1756 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 1.411 _refine_ls_shift/su_max 5.027 _refine_ls_shift/su_mean 0.082 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 Cl1 Cl 0.6784(3) 0.7111(3) 0.10672(16) 0.0868(11) Uani 1 1 d . . . O1 O 0.1565(7) 0.8304(8) 0.4261(4) 0.0690(19) Uani 1 1 d . . . O2 O -0.0619(6) 0.9362(7) 0.3774(3) 0.0615(19) Uani 1 1 d . . . O3 O 0.0515(7) 0.6546(7) 0.3160(4) 0.0673(19) Uani 1 1 d . . . O4 O 0.0909(8) 0.6889(8) 0.1990(4) 0.082(2) Uani 1 1 d . . . O5 O 0.2980(10) 0.8876(13) 0.0367(5) 0.111(3) Uani 1 1 d . . . O6 O 0.3786(10) 0.6364(9) 0.0496(4) 0.103(3) Uani 1 1 d D . . O7 O 0.5837(8) 0.8224(8) 0.2659(4) 0.081(2) Uani 1 1 d . . . O8 O 0.6658(6) 1.0438(6) 0.1835(4) 0.066(2) Uani 1 1 d . . . O9 O 0.3977(10) 1.3767(7) 0.4084(4) 0.092(2) Uani 1 1 d . . . N1 N 0.2928(8) 1.1437(8) 0.1742(4) 0.060(2) Uani 1 1 d . . . C1 C 0.1921(9) 0.9584(9) 0.3058(5) 0.047(2) Uani 1 1 d . . . C2 C 0.0956(11) 0.8964(10) 0.3774(6) 0.059(3) Uani 1 1 d . . . C3 C -0.1693(10) 0.8825(13) 0.4434(5) 0.069(3) Uani 1 1 d . . . H3A H -0.1369 0.9325 0.4790 0.083 Uiso 1 1 calc R . . H3B H -0.1644 0.7666 0.4584 0.083 Uiso 1 1 calc R . . C4 C -0.3375(12) 0.9315(14) 0.4308(7) 0.100(4) Uani 1 1 d . . . H4A H -0.4111 0.9043 0.4735 0.150 Uiso 1 1 calc R . . H4B H -0.3705 0.8762 0.3974 0.150 Uiso 1 1 calc R . . H4C H -0.3391 1.0456 0.4133 0.150 Uiso 1 1 calc R . . C5 C 0.1934(8) 0.8906(9) 0.2520(5) 0.049(2) Uani 1 1 d . . . C6 C 0.1074(10) 0.7358(10) 0.2505(6) 0.053(3) Uani 1 1 d . . . C7 C -0.0344(13) 0.5034(11) 0.3210(7) 0.090(4) Uani 1 1 d . . . H7A H 0.0348 0.4313 0.2980 0.107 Uiso 1 1 calc R . . H7B H -0.1316 0.5229 0.2991 0.107 Uiso 1 1 calc R . . C8 C -0.0791(14) 0.4297(14) 0.3966(7) 0.108(5) Uani 1 1 d . . . H8A H -0.1377 0.3305 0.4015 0.163 Uiso 1 1 calc R . . H8B H -0.1463 0.5026 0.4190 0.163 Uiso 1 1 calc R . . H8C H 0.0180 0.4089 0.4176 0.163 Uiso 1 1 calc R . . C9 C 0.4888(9) 0.8059(9) 0.1162(4) 0.045(2) Uani 1 1 d . . . C10 C 0.3846(14) 0.7774(18) 0.0651(6) 0.087(4) Uani 1 1 d . . . C11 C 0.234(3) 0.661(4) 0.0114(19) 0.615(9) Uani 1 1 d DU . . H11A H 0.2306 0.7757 -0.0068 0.738 Uiso 1 1 calc R . . H11B H 0.2624 0.6112 -0.0285 0.738 Uiso 1 1 calc R . . C12 C 0.080(2) 0.615(3) 0.0372(15) 0.237(13) Uani 1 1 d . . . H12A H 0.0150 0.6315 0.0002 0.355 Uiso 1 1 calc R . . H12B H 0.0371 0.6779 0.0706 0.355 Uiso 1 1 calc R . . H12C H 0.0764 0.5031 0.0591 0.355 Uiso 1 1 calc R . . C13 C 0.4507(8) 0.8930(8) 0.1647(5) 0.047(2) Uani 1 1 d . . . C14 C 0.5718(10) 0.9114(11) 0.2094(6) 0.059(3) Uani 1 1 d . . . C15 C 0.7841(12) 1.0838(14) 0.2258(7) 0.092(4) Uani 1 1 d . . . H15A H 0.8634 0.9988 0.2319 0.110 Uiso 1 1 calc R . . H15B H 0.7285 1.0923 0.2713 0.110 Uiso 1 1 calc R . . C16 C 0.8674(13) 1.2372(14) 0.1918(8) 0.109(5) Uani 1 1 d . . . H16A H 0.9437 1.2627 0.2200 0.164 Uiso 1 1 calc R . . H16B H 0.7887 1.3212 0.1861 0.164 Uiso 1 1 calc R . . H16C H 0.9241 1.2279 0.1472 0.164 Uiso 1 1 calc R . . C17 C 0.2809(9) 0.9676(8) 0.1794(4) 0.045(2) Uani 1 1 d . . . H17A H 0.2152 0.9476 0.1449 0.054 Uiso 1 1 calc R . . C18 C 0.3399(13) 1.2338(10) 0.1033(5) 0.075(3) Uani 1 1 d . . . H18A H 0.3465 1.3465 0.1035 0.113 Uiso 1 1 calc R . . H18B H 0.2602 1.2162 0.0752 0.113 Uiso 1 1 calc R . . H18C H 0.4440 1.1979 0.0846 0.113 Uiso 1 1 calc R . . C19 C 0.3265(9) 1.2059(9) 0.2295(5) 0.053(3) Uani 1 1 d . . . C20 C 0.3989(11) 1.3543(9) 0.2246(5) 0.060(3) Uani 1 1 d . . . H20A H 0.4352 1.4145 0.1806 0.071 Uiso 1 1 calc R . . C21 C 0.4203(10) 1.4175(10) 0.2802(6) 0.061(3) Uani 1 1 d . . . H21A H 0.4648 1.5203 0.2735 0.073 Uiso 1 1 calc R . . C22 C 0.3749(11) 1.3270(10) 0.3483(6) 0.061(3) Uani 1 1 d . . . C23 C 0.3061(10) 1.1760(9) 0.3548(5) 0.054(2) Uani 1 1 d . . . H23A H 0.2769 1.1139 0.3991 0.065 Uiso 1 1 calc R . . C24 C 0.2793(9) 1.1147(8) 0.2992(4) 0.040(2) Uani 1 1 d . . . C25 C 0.4319(15) 1.5440(12) 0.4030(7) 0.097(4) Uani 1 1 d . . . H25A H 0.4482 1.5624 0.4475 0.146 Uiso 1 1 calc R . . H25B H 0.3420 1.6067 0.3876 0.146 Uiso 1 1 calc R . . H25C H 0.5284 1.5750 0.3702 0.146 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 Cl1 0.0688(15) 0.0736(15) 0.108(2) -0.0201(14) 0.0173(15) 0.0244(12) O1 0.075(4) 0.079(4) 0.046(5) -0.003(3) -0.003(4) 0.000(3) O2 0.048(3) 0.081(4) 0.044(4) -0.001(3) 0.013(3) 0.006(3) O3 0.080(4) 0.057(3) 0.061(5) -0.013(3) 0.006(4) -0.011(3) O4 0.098(5) 0.091(5) 0.059(6) -0.024(4) -0.003(4) -0.024(4) O5 0.093(5) 0.187(9) 0.083(7) -0.082(6) -0.039(5) 0.040(6) O6 0.152(7) 0.095(5) 0.065(6) -0.033(4) 0.002(5) -0.051(5) O7 0.087(4) 0.088(5) 0.066(6) 0.008(4) -0.037(4) -0.005(4) O8 0.055(3) 0.064(4) 0.075(6) -0.002(3) -0.014(3) -0.002(3) O9 0.154(6) 0.054(4) 0.071(6) -0.015(4) -0.019(5) -0.013(4) N1 0.073(5) 0.047(4) 0.052(6) -0.004(4) 0.005(4) 0.014(3) C1 0.051(4) 0.053(5) 0.037(6) -0.018(4) 0.000(4) 0.003(4) C2 0.062(6) 0.059(5) 0.048(7) -0.001(5) -0.001(5) 0.006(4) C3 0.064(6) 0.108(7) 0.031(6) -0.011(5) 0.002(5) -0.013(5) C4 0.076(7) 0.128(9) 0.086(10) -0.022(7) 0.021(7) -0.003(6) C5 0.037(4) 0.059(5) 0.039(6) 0.006(4) 0.006(4) -0.002(4) C6 0.049(5) 0.060(5) 0.051(7) -0.018(5) 0.002(5) -0.001(4) C7 0.092(7) 0.062(6) 0.104(11) -0.001(6) 0.002(7) -0.035(5) C8 0.105(8) 0.104(8) 0.100(12) 0.007(7) 0.002(8) -0.044(7) C9 0.046(4) 0.044(4) 0.041(6) -0.011(4) 0.006(4) -0.003(3) C10 0.074(7) 0.140(11) 0.053(8) -0.057(8) 0.025(7) -0.049(8) C11 0.567(12) 0.717(14) 0.569(19) -0.103(14) -0.074(13) -0.593 C12 0.126(13) 0.21(2) 0.33(4) 0.00(2) 0.022(16) 0.026(14) C13 0.033(4) 0.044(4) 0.057(7) -0.002(4) 0.005(4) 0.004(3) C14 0.045(5) 0.057(5) 0.074(8) -0.017(5) 0.002(5) 0.002(4) C15 0.080(7) 0.113(9) 0.084(11) 0.004(7) -0.049(7) -0.022(6) C16 0.090(8) 0.115(9) 0.144(15) -0.049(9) -0.048(8) -0.016(7) C17 0.056(4) 0.047(4) 0.038(5) -0.019(4) -0.013(4) 0.010(4) C18 0.114(7) 0.061(5) 0.042(7) 0.007(4) -0.008(6) 0.008(5) C19 0.052(4) 0.040(5) 0.062(7) -0.011(4) 0.005(5) 0.009(4) C20 0.081(6) 0.039(5) 0.048(7) 0.003(4) 0.007(5) 0.007(4) C21 0.072(6) 0.041(4) 0.068(8) -0.010(5) -0.009(5) -0.001(4) C22 0.077(6) 0.051(5) 0.058(8) -0.018(5) -0.007(6) 0.002(4) C23 0.068(5) 0.053(5) 0.039(6) -0.010(4) 0.000(5) -0.003(4) C24 0.056(4) 0.041(4) 0.026(5) -0.014(3) -0.002(4) -0.002(3) C25 0.140(9) 0.068(7) 0.101(11) -0.033(6) -0.049(8) 0.004(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 Cl1 C9 1.760(8) . ? O1 C2 1.193(12) . ? O2 C2 1.346(10) . ? O2 C3 1.467(10) . ? O3 C6 1.361(11) . ? O3 C7 1.458(11) . ? O4 C6 1.202(12) . ? O5 C10 1.262(16) . ? O6 C10 1.299(13) . ? O6 C11 1.503(15) . ? O7 C14 1.236(12) . ? O8 C14 1.347(10) . ? O8 C15 1.472(13) . ? O9 C22 1.387(13) . ? O9 C25 1.432(12) . ? N1 C19 1.380(12) . ? N1 C18 1.461(11) . ? N1 C17 1.481(10) . ? C1 C5 1.315(12) . ? C1 C24 1.495(11) . ? C1 C2 1.524(12) . ? C3 C4 1.494(15) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.514(13) . ? C5 C17 1.537(11) . ? C7 C8 1.500(17) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C13 1.332(12) . ? C9 C10 1.487(16) . ? C11 C12 1.34(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.468(14) . ? C13 C17 1.550(10) . ? C15 C16 1.471(15) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.384(12) . ? C19 C24 1.447(12) . ? C20 C21 1.360(14) . ? C20 H20A 0.9300 . ? C21 C22 1.414(14) . ? C21 H21A 0.9300 . ? C22 C23 1.386(12) . ? C23 C24 1.363(12) . ? C23 H23A 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O2 C3 115.8(7) . . ? C6 O3 C7 115.9(8) . . ? C10 O6 C11 99.0(17) . . ? C14 O8 C15 117.6(8) . . ? C22 O9 C25 117.5(9) . . ? C19 N1 C18 120.0(8) . . ? C19 N1 C17 120.8(7) . . ? C18 N1 C17 113.6(8) . . ? C5 C1 C24 121.0(7) . . ? C5 C1 C2 125.0(8) . . ? C24 C1 C2 113.9(8) . . ? O1 C2 O2 126.5(8) . . ? O1 C2 C1 123.3(8) . . ? O2 C2 C1 110.1(8) . . ? O2 C3 C4 106.7(8) . . ? O2 C3 H3A 110.4 . . ? C4 C3 H3A 110.4 . . ? O2 C3 H3B 110.4 . . ? C4 C3 H3B 110.4 . . ? H3A C3 H3B 108.6 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C1 C5 C6 126.7(7) . . ? C1 C5 C17 122.4(8) . . ? C6 C5 C17 110.9(8) . . ? O4 C6 O3 123.9(8) . . ? O4 C6 C5 125.1(8) . . ? O3 C6 C5 111.0(9) . . ? O3 C7 C8 107.6(10) . . ? O3 C7 H7A 110.2 . . ? C8 C7 H7A 110.2 . . ? O3 C7 H7B 110.1 . . ? C8 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C13 C9 C10 126.4(8) . . ? C13 C9 Cl1 120.9(8) . . ? C10 C9 Cl1 112.7(7) . . ? O5 C10 O6 118.4(13) . . ? O5 C10 C9 121.3(11) . . ? O6 C10 C9 120.4(14) . . ? C12 C11 O6 127(3) . . ? C12 C11 H11A 106.0 . . ? O6 C11 H11A 105.9 . . ? C12 C11 H11B 105.1 . . ? O6 C11 H11B 105.4 . . ? H11A C11 H11B 106.2 . . ? C11 C12 H12A 109.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.7 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 C14 118.6(7) . . ? C9 C13 C17 123.2(9) . . ? C14 C13 C17 118.1(7) . . ? O7 C14 O8 122.7(10) . . ? O7 C14 C13 125.3(8) . . ? O8 C14 C13 111.9(8) . . ? O8 C15 C16 110.1(9) . . ? O8 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? O8 C15 H15B 109.6 . . ? C16 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N1 C17 C5 108.8(6) . . ? N1 C17 C13 111.5(6) . . ? C5 C17 C13 111.1(6) . . ? N1 C17 H17A 108.5 . . ? C5 C17 H17A 108.5 . . ? C13 C17 H17A 108.4 . . ? N1 C18 H18A 109.4 . . ? N1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 C20 125.3(8) . . ? N1 C19 C24 119.2(7) . . ? C20 C19 C24 115.5(9) . . ? C21 C20 C19 124.1(8) . . ? C21 C20 H20A 117.9 . . ? C19 C20 H20A 118.0 . . ? C20 C21 C22 120.1(8) . . ? C20 C21 H21A 120.0 . . ? C22 C21 H21A 120.0 . . ? C23 C22 O9 118.0(9) . . ? C23 C22 C21 117.2(10) . . ? O9 C22 C21 124.8(8) . . ? C24 C23 C22 122.9(8) . . ? C24 C23 H23A 118.6 . . ? C22 C23 H23A 118.5 . . ? C23 C24 C19 120.3(7) . . ? C23 C24 C1 123.3(7) . . ? C19 C24 C1 116.3(8) . . ? O9 C25 H25A 109.5 . . ? O9 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O9 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 O2 C2 O1 -4.4(14) . . . . ? C3 O2 C2 C1 179.6(8) . . . . ? C5 C1 C2 O1 105.9(13) . . . . ? C24 C1 C2 O1 -78.5(11) . . . . ? C5 C1 C2 O2 -78.0(10) . . . . ? C24 C1 C2 O2 97.6(9) . . . . ? C2 O2 C3 C4 -177.1(8) . . . . ? C24 C1 C5 C6 -178.3(7) . . . . ? C2 C1 C5 C6 -3.0(14) . . . . ? C24 C1 C5 C17 -1.1(12) . . . . ? C2 C1 C5 C17 174.2(7) . . . . ? C7 O3 C6 O4 -0.8(13) . . . . ? C7 O3 C6 C5 179.8(7) . . . . ? C1 C5 C6 O4 168.5(9) . . . . ? C17 C5 C6 O4 -9.0(12) . . . . ? C1 C5 C6 O3 -12.0(12) . . . . ? C17 C5 C6 O3 170.5(6) . . . . ? C6 O3 C7 C8 177.5(8) . . . . ? C11 O6 C10 O5 -11.1(18) . . . . ? C11 O6 C10 C9 167.6(15) . . . . ? C13 C9 C10 O5 39.0(14) . . . . ? Cl1 C9 C10 O5 -140.7(8) . . . . ? C13 C9 C10 O6 -139.7(9) . . . . ? Cl1 C9 C10 O6 40.6(10) . . . . ? C10 O6 C11 C12 -98(3) . . . . ? C10 C9 C13 C14 -178.3(9) . . . . ? Cl1 C9 C13 C14 1.3(10) . . . . ? C10 C9 C13 C17 5.5(13) . . . . ? Cl1 C9 C13 C17 -174.9(5) . . . . ? C15 O8 C14 O7 -1.4(12) . . . . ? C15 O8 C14 C13 175.4(8) . . . . ? C9 C13 C14 O7 -91.5(11) . . . . ? C17 C13 C14 O7 84.9(10) . . . . ? C9 C13 C14 O8 91.9(8) . . . . ? C17 C13 C14 O8 -91.8(8) . . . . ? C14 O8 C15 C16 -176.1(8) . . . . ? C19 N1 C17 C5 39.4(10) . . . . ? C18 N1 C17 C5 -166.9(8) . . . . ? C19 N1 C17 C13 -83.5(9) . . . . ? C18 N1 C17 C13 70.2(10) . . . . ? C1 C5 C17 N1 -24.7(11) . . . . ? C6 C5 C17 N1 152.9(7) . . . . ? C1 C5 C17 C13 98.4(9) . . . . ? C6 C5 C17 C13 -84.0(9) . . . . ? C9 C13 C17 N1 -124.4(8) . . . . ? C14 C13 C17 N1 59.4(9) . . . . ? C9 C13 C17 C5 114.1(9) . . . . ? C14 C13 C17 C5 -62.1(9) . . . . ? C18 N1 C19 C20 2.3(12) . . . . ? C17 N1 C19 C20 154.4(7) . . . . ? C18 N1 C19 C24 -179.8(7) . . . . ? C17 N1 C19 C24 -27.8(10) . . . . ? N1 C19 C20 C21 175.2(8) . . . . ? C24 C19 C20 C21 -2.7(12) . . . . ? C19 C20 C21 C22 3.3(14) . . . . ? C25 O9 C22 C23 -165.6(8) . . . . ? C25 O9 C22 C21 16.0(14) . . . . ? C20 C21 C22 C23 -1.3(13) . . . . ? C20 C21 C22 O9 177.1(9) . . . . ? O9 C22 C23 C24 -179.5(8) . . . . ? C21 C22 C23 C24 -1.0(12) . . . . ? C22 C23 C24 C19 1.5(12) . . . . ? C22 C23 C24 C1 -174.5(7) . . . . ? N1 C19 C24 C23 -177.7(7) . . . . ? C20 C19 C24 C23 0.3(10) . . . . ? N1 C19 C24 C1 -1.5(10) . . . . ? C20 C19 C24 C1 176.5(7) . . . . ? C5 C1 C24 C23 -168.2(8) . . . . ? C2 C1 C24 C23 16.0(11) . . . . ? C5 C1 C24 C19 15.7(11) . . . . ? C2 C1 C24 C19 -160.0(7) . . . . ? _diffrn_measured_fraction_theta_max 0.785 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.785 _refine_diff_density_max 0.539 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.059 data_sx584 _database_code_CSD 203554 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-Benzyl-7-methoxy-4-(4-methoxyphenyl)-5-phenylbenzo[f][1,4]diazepine- 2,3-dicarbox-ylic anhydride ; _chemical_name_common ; 1-Benzyl-7-methoxy-4-(4-methoxyphenyl)-5- phenylbenzo(f)(1,4)diazepine-2,3-dicarbox-ylic anhydride ; _chemical_melting_point 442 _chemical_formula_moiety ? _chemical_formula_sum 'C32 H26 N2 O5' _chemical_formula_weight 518.55 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.0481(11) _cell_length_b 14.5004(17) _cell_length_c 16.407(2) _cell_angle_alpha 81.45(3) _cell_angle_beta 83.18(5) _cell_angle_gamma 67.320(17) _cell_volume 2609.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour Red _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9659 _exptl_absorpt_correction_T_max 0.9792 _exptl_absorpt_process_details 'Psi scan' _exptl_special_details ; Crystallization solvent Ethyl acetate ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method 'Rigaku R-axis RAPID IP' _diffrn_detector_area_resol_mean Oscillation _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17892 _diffrn_reflns_av_R_equivalents 0.0682 _diffrn_reflns_av_sigmaI/netI 0.2846 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.48 _reflns_number_total 11548 _reflns_number_gt 3151 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID AUTO (Rigaku,2001)' _computing_cell_refinement 'RAPID AUTO (Rigaku,2001)' _computing_data_reduction 'RAPID AUTO (Rigaku,2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Siemens,1994)' _computing_publication_material 'SHELXTL (Siemens,1994)' _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^)+(0.0298P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11548 _refine_ls_number_parameters 703 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2119 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.0918 _refine_ls_wR_factor_gt 0.0726 _refine_ls_goodness_of_fit_ref 0.641 _refine_ls_restrained_S_all 0.641 _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 -0.1683(2) 1.50768(17) 0.07854(13) 0.0782(7) Uani 1 1 d . . . O2 O -0.3384(2) 1.16719(17) 0.41499(12) 0.0835(7) Uani 1 1 d . . . O3 O 0.13721(18) 0.88129(14) 0.08677(11) 0.0623(6) Uani 1 1 d . . . O4 O 0.0908(2) 0.88279(15) 0.22318(11) 0.0741(7) Uani 1 1 d . . . O5 O 0.1744(2) 0.92917(14) -0.04591(11) 0.0779(7) Uani 1 1 d . . . O6 O -0.4218(3) 1.7814(2) 0.39257(14) 0.1019(10) Uani 1 1 d . . . O7 O -0.3811(2) 1.39576(18) 0.07371(13) 0.0913(8) Uani 1 1 d . . . O8 O -1.0018(2) 1.64180(18) 0.26466(11) 0.0618(6) Uani 1 1 d . . . O9 O -1.10653(19) 1.79327(19) 0.30807(13) 0.0756(7) Uani 1 1 d . . . O10 O -0.8545(2) 1.49220(17) 0.24547(12) 0.0755(7) Uani 1 1 d . . . N1 N 0.1504(2) 1.12585(18) 0.00916(12) 0.0449(6) Uani 1 1 d . . . N2 N 0.07340(19) 1.09467(16) 0.20002(12) 0.0413(6) Uani 1 1 d . . . N3 N -0.8811(2) 1.76396(16) 0.39069(12) 0.0411(6) Uani 1 1 d . . . N4 N -0.7031(2) 1.55504(17) 0.33752(13) 0.0481(6) Uani 1 1 d . . . C1 C 0.4003(3) 1.1393(2) -0.03662(17) 0.0597(9) Uani 1 1 d . . . H1A H 0.3994 1.0995 0.0132 0.072 Uiso 1 1 calc R . . C2 C 0.4929(3) 1.1742(3) -0.0572(2) 0.0760(10) Uani 1 1 d . . . H2A H 0.5547 1.1567 -0.0220 0.091 Uiso 1 1 calc R . . C3 C 0.4934(3) 1.2349(3) -0.1301(2) 0.0863(12) Uani 1 1 d . . . H3A H 0.5559 1.2581 -0.1446 0.104 Uiso 1 1 calc R . . C4 C 0.4012(4) 1.2609(3) -0.1810(2) 0.0853(12) Uani 1 1 d . . . H4A H 0.4006 1.3032 -0.2297 0.102 Uiso 1 1 calc R . . C5 C 0.3090(3) 1.2250(2) -0.16104(18) 0.0661(10) Uani 1 1 d . . . H5A H 0.2471 1.2429 -0.1962 0.079 Uiso 1 1 calc R . . C6 C 0.3095(3) 1.1625(2) -0.08842(17) 0.0464(8) Uani 1 1 d . . . C7 C 0.2199(3) 1.1123(2) -0.07204(15) 0.0549(8) Uani 1 1 d . . . H7A H 0.1637 1.1382 -0.1152 0.066 Uiso 1 1 calc R . . H7B H 0.2624 1.0408 -0.0756 0.066 Uiso 1 1 calc R . . C8 C 0.0728(2) 1.2250(2) 0.02648(16) 0.0408(7) Uani 1 1 d . . . C9 C 0.0177(3) 1.2966(2) -0.03745(17) 0.0571(9) Uani 1 1 d . . . H9A H 0.0345 1.2797 -0.0913 0.069 Uiso 1 1 calc R . . C10 C -0.0616(3) 1.3924(2) -0.02325(19) 0.0609(9) Uani 1 1 d . . . H10A H -0.0968 1.4394 -0.0671 0.073 Uiso 1 1 calc R . . C11 C -0.0877(3) 1.4170(2) 0.0560(2) 0.0554(8) Uani 1 1 d . . . C12 C -0.0299(3) 1.3466(2) 0.12039(17) 0.0512(8) Uani 1 1 d . . . H12A H -0.0464 1.3644 0.1740 0.061 Uiso 1 1 calc R . . C13 C 0.0509(2) 1.2513(2) 0.10711(15) 0.0381(7) Uani 1 1 d . . . C14 C 0.1102(2) 1.1824(2) 0.18116(15) 0.0408(7) Uani 1 1 d . . . H14A H 0.0779 1.2214 0.2283 0.049 Uiso 1 1 calc R . . C15 C 0.2457(3) 1.1547(2) 0.17666(15) 0.0420(7) Uani 1 1 d . . . C16 C 0.3269(3) 1.0582(2) 0.18996(15) 0.0531(8) Uani 1 1 d . . . H16A H 0.2999 1.0053 0.2014 0.064 Uiso 1 1 calc R . . C17 C 0.4496(3) 1.0385(3) 0.18652(17) 0.0698(10) Uani 1 1 d . . . H17A H 0.5043 0.9724 0.1942 0.084 Uiso 1 1 calc R . . C18 C 0.4910(3) 1.1165(4) 0.17169(18) 0.0793(12) Uani 1 1 d . . . H18A H 0.5732 1.1033 0.1688 0.095 Uiso 1 1 calc R . . C19 C 0.4090(4) 1.2136(3) 0.16133(19) 0.0765(11) Uani 1 1 d . . . H19A H 0.4357 1.2668 0.1533 0.092 Uiso 1 1 calc R . . C20 C 0.2881(3) 1.2330(2) 0.16274(16) 0.0598(9) Uani 1 1 d . . . H20A H 0.2338 1.2991 0.1543 0.072 Uiso 1 1 calc R . . C21 C 0.1370(2) 1.0444(2) 0.05737(16) 0.0372(7) Uani 1 1 d . . . C22 C 0.1548(3) 0.9498(2) 0.02341(19) 0.0534(8) Uani 1 1 d . . . C23 C 0.1056(3) 0.9283(2) 0.15942(18) 0.0518(8) Uani 1 1 d . . . C24 C 0.0991(2) 1.0320(2) 0.13835(16) 0.0415(7) Uani 1 1 d . . . C25 C -0.0322(2) 1.1070(2) 0.25475(15) 0.0392(7) Uani 1 1 d . . . C26 C -0.0399(2) 1.14134(19) 0.33115(15) 0.0461(8) Uani 1 1 d . . . H26A H 0.0251 1.1520 0.3476 0.055 Uiso 1 1 calc R . . C27 C -0.1433(3) 1.1594(2) 0.38192(15) 0.0545(9) Uani 1 1 d . . . H27A H -0.1486 1.1840 0.4320 0.065 Uiso 1 1 calc R . . C28 C -0.2387(3) 1.1418(2) 0.36006(17) 0.0561(9) Uani 1 1 d . . . C29 C -0.2316(3) 1.1040(2) 0.28673(17) 0.0625(9) Uani 1 1 d . . . H29A H -0.2948 1.0889 0.2727 0.075 Uiso 1 1 calc R . . C30 C -0.1284(3) 1.0887(2) 0.23398(16) 0.0571(9) Uani 1 1 d . . . H30A H -0.1244 1.0656 0.1834 0.068 Uiso 1 1 calc R . . C31 C -0.4412(3) 1.1517(3) 0.39617(18) 0.0965(12) Uani 1 1 d . . . H31A H -0.5041 1.1733 0.4390 0.145 Uiso 1 1 calc R . . H31B H -0.4206 1.0815 0.3923 0.145 Uiso 1 1 calc R . . H31C H -0.4687 1.1898 0.3444 0.145 Uiso 1 1 calc R . . C32 C -0.2335(3) 1.5778(2) 0.0150(2) 0.0956(12) Uani 1 1 d . . . H32A H -0.2875 1.6377 0.0379 0.143 Uiso 1 1 calc R . . H32B H -0.2790 1.5490 -0.0099 0.143 Uiso 1 1 calc R . . H32C H -0.1783 1.5943 -0.0260 0.143 Uiso 1 1 calc R . . C33 C -1.0334(3) 1.7176(2) 0.52882(16) 0.0549(9) Uani 1 1 d . . . H33A H -0.9586 1.6692 0.5155 0.066 Uiso 1 1 calc R . . C34 C -1.1097(3) 1.6932(3) 0.59121(18) 0.0698(10) Uani 1 1 d . . . H34A H -1.0854 1.6287 0.6193 0.084 Uiso 1 1 calc R . . C35 C -1.2207(4) 1.7639(4) 0.6116(2) 0.0798(13) Uani 1 1 d . . . H35A H -1.2724 1.7477 0.6528 0.096 Uiso 1 1 calc R . . C36 C -1.2538(3) 1.8584(3) 0.5702(2) 0.0802(12) Uani 1 1 d . . . H36A H -1.3284 1.9069 0.5842 0.096 Uiso 1 1 calc R . . C37 C -1.1791(3) 1.8834(2) 0.50818(19) 0.0645(9) Uani 1 1 d . . . H37A H -1.2038 1.9483 0.4807 0.077 Uiso 1 1 calc R . . C38 C -1.0678(3) 1.8129(2) 0.48660(16) 0.0449(8) Uani 1 1 d . . . C39 C -0.9860(2) 1.8464(2) 0.42269(16) 0.0476(8) Uani 1 1 d . . . H39A H -1.0328 1.8862 0.3767 0.057 Uiso 1 1 calc R . . H39B H -0.9573 1.8896 0.4468 0.057 Uiso 1 1 calc R . . C40 C -0.7627(3) 1.7685(2) 0.38714(15) 0.0410(7) Uani 1 1 d . . . C41 C -0.7542(3) 1.8635(2) 0.37295(15) 0.0523(8) Uani 1 1 d . . . H41A H -0.8229 1.9210 0.3631 0.063 Uiso 1 1 calc R . . C42 C -0.6430(3) 1.8716(3) 0.37369(17) 0.0604(9) Uani 1 1 d . . . H42A H -0.6373 1.9345 0.3648 0.073 Uiso 1 1 calc R . . C43 C -0.5429(3) 1.7874(3) 0.38741(18) 0.0627(10) Uani 1 1 d . . . C44 C -0.5502(3) 1.6938(2) 0.39746(15) 0.0533(8) Uani 1 1 d . . . H44A H -0.4804 1.6366 0.4042 0.064 Uiso 1 1 calc R . . C45 C -0.6595(3) 1.6838(2) 0.39773(14) 0.0406(7) Uani 1 1 d . . . C46 C -0.6575(2) 1.5765(2) 0.40920(15) 0.0458(8) Uani 1 1 d . . . H46A H -0.5722 1.5321 0.4098 0.055 Uiso 1 1 calc R . . C47 C -0.7169(3) 1.5476(2) 0.49062(16) 0.0467(8) Uani 1 1 d . . . C48 C -0.7704(3) 1.4779(2) 0.49739(18) 0.0715(10) Uani 1 1 d . . . H48A H -0.7758 1.4513 0.4505 0.086 Uiso 1 1 calc R . . C49 C -0.8161(3) 1.4472(2) 0.5733(2) 0.0915(13) Uani 1 1 d . . . H49A H -0.8518 1.4000 0.5770 0.110 Uiso 1 1 calc R . . C50 C -0.8091(3) 1.4859(3) 0.6436(2) 0.0833(11) Uani 1 1 d . . . H50A H -0.8408 1.4658 0.6945 0.100 Uiso 1 1 calc R . . C51 C -0.7549(3) 1.5545(2) 0.63764(17) 0.0674(10) Uani 1 1 d . . . H51A H -0.7491 1.5806 0.6847 0.081 Uiso 1 1 calc R . . C52 C -0.7087(2) 1.5851(2) 0.56175(17) 0.0549(8) Uani 1 1 d . . . H52A H -0.6717 1.6313 0.5584 0.066 Uiso 1 1 calc R . . C53 C -0.8198(3) 1.6102(2) 0.31967(15) 0.0396(7) Uani 1 1 d . . . C54 C -0.8854(3) 1.5709(3) 0.27294(17) 0.0549(9) Uani 1 1 d . . . C55 C -1.0153(3) 1.7225(3) 0.30798(18) 0.0541(9) Uani 1 1 d . . . C56 C -0.8997(3) 1.6989(2) 0.34436(15) 0.0384(7) Uani 1 1 d . . . C57 C -0.6171(3) 1.5133(2) 0.27098(18) 0.0484(8) Uani 1 1 d . . . C58 C -0.6301(3) 1.5632(2) 0.19170(19) 0.0637(9) Uani 1 1 d . . . H58A H -0.6933 1.6247 0.1814 0.076 Uiso 1 1 calc R . . C59 C -0.5487(3) 1.5213(3) 0.12801(19) 0.0726(10) Uani 1 1 d . . . H59A H -0.5579 1.5548 0.0748 0.087 Uiso 1 1 calc R . . C60 C -0.4549(3) 1.4315(3) 0.1419(2) 0.0639(9) Uani 1 1 d . . . C61 C -0.4397(3) 1.3813(2) 0.2208(2) 0.0645(9) Uani 1 1 d . . . H61A H -0.3755 1.3205 0.2311 0.077 Uiso 1 1 calc R . . C62 C -0.5225(3) 1.4237(2) 0.28455(18) 0.0644(9) Uani 1 1 d . . . H62A H -0.5132 1.3902 0.3377 0.077 Uiso 1 1 calc R . . C63 C -0.2952(3) 1.2962(3) 0.0805(2) 0.0921(12) Uani 1 1 d . . . H63A H -0.2507 1.2824 0.0283 0.138 Uiso 1 1 calc R . . H63B H -0.3356 1.2501 0.0964 0.138 Uiso 1 1 calc R . . H63C H -0.2407 1.2885 0.1215 0.138 Uiso 1 1 calc R . . C64 C -0.4079(4) 1.8667(3) 0.3801(2) 0.1202(15) Uani 1 1 d . . . H64A H -0.3249 1.8556 0.3844 0.180 Uiso 1 1 calc R . . H64B H -0.4572 1.9092 0.4207 0.180 Uiso 1 1 calc R . . H64C H -0.4315 1.8987 0.3259 0.180 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 0.0783(17) 0.0399(16) 0.0986(17) -0.0006(14) -0.0051(15) -0.0054(14) O2 0.0567(15) 0.139(2) 0.0656(14) -0.0285(14) 0.0163(13) -0.0484(16) O3 0.1048(18) 0.0391(14) 0.0527(12) -0.0118(11) -0.0011(13) -0.0364(13) O4 0.126(2) 0.0571(16) 0.0479(12) 0.0032(11) 0.0020(14) -0.0493(15) O5 0.134(2) 0.0601(16) 0.0493(12) -0.0223(11) -0.0021(14) -0.0425(15) O6 0.139(3) 0.121(3) 0.0947(18) -0.0191(17) 0.0100(17) -0.105(2) O7 0.102(2) 0.0642(19) 0.0889(17) -0.0279(15) 0.0298(16) -0.0134(16) O8 0.0622(16) 0.0816(19) 0.0573(13) -0.0136(12) -0.0099(12) -0.0404(15) O9 0.0451(15) 0.100(2) 0.0801(16) -0.0175(15) -0.0121(14) -0.0210(15) O10 0.0975(19) 0.0702(19) 0.0771(15) -0.0230(13) -0.0112(14) -0.0445(16) N1 0.0586(17) 0.0419(18) 0.0333(13) -0.0058(12) 0.0098(13) -0.0211(15) N2 0.0540(16) 0.0378(17) 0.0385(13) -0.0111(12) 0.0048(13) -0.0241(14) N3 0.0383(16) 0.0418(17) 0.0456(14) -0.0046(12) 0.0013(13) -0.0188(14) N4 0.0523(18) 0.0492(18) 0.0456(15) -0.0121(13) -0.0079(15) -0.0182(15) C1 0.058(2) 0.066(3) 0.049(2) -0.0089(17) 0.0050(19) -0.019(2) C2 0.061(3) 0.089(3) 0.079(3) -0.022(2) -0.001(2) -0.026(2) C3 0.080(3) 0.099(3) 0.097(3) -0.028(3) 0.031(3) -0.056(3) C4 0.100(3) 0.091(3) 0.070(3) -0.002(2) 0.016(3) -0.049(3) C5 0.066(2) 0.078(3) 0.053(2) -0.0012(19) 0.0008(19) -0.028(2) C6 0.055(2) 0.039(2) 0.0363(17) -0.0021(15) 0.0098(17) -0.0127(17) C7 0.070(2) 0.054(2) 0.0422(17) -0.0136(15) 0.0140(17) -0.0269(19) C8 0.0456(19) 0.035(2) 0.0407(17) -0.0030(16) 0.0011(16) -0.0151(17) C9 0.064(2) 0.057(3) 0.0438(18) -0.0039(18) -0.0021(18) -0.017(2) C10 0.062(2) 0.042(2) 0.064(2) 0.0091(18) -0.006(2) -0.008(2) C11 0.052(2) 0.034(2) 0.075(2) -0.010(2) 0.007(2) -0.0120(19) C12 0.054(2) 0.050(2) 0.053(2) -0.0108(18) 0.0040(18) -0.0230(19) C13 0.0381(18) 0.034(2) 0.0452(18) -0.0120(15) 0.0041(16) -0.0167(16) C14 0.052(2) 0.037(2) 0.0378(16) -0.0136(14) 0.0032(16) -0.0202(17) C15 0.050(2) 0.045(2) 0.0325(15) -0.0034(15) -0.0029(15) -0.0190(19) C16 0.054(2) 0.066(3) 0.0466(19) -0.0048(17) -0.0071(18) -0.029(2) C17 0.063(3) 0.084(3) 0.060(2) -0.016(2) -0.009(2) -0.021(2) C18 0.061(3) 0.130(4) 0.062(2) -0.021(3) -0.011(2) -0.047(3) C19 0.078(3) 0.093(4) 0.080(2) -0.010(2) -0.009(2) -0.053(3) C20 0.068(3) 0.062(3) 0.062(2) -0.0012(17) -0.0044(19) -0.039(2) C21 0.0436(18) 0.0279(19) 0.0413(17) -0.0110(15) 0.0017(15) -0.0135(16) C22 0.068(2) 0.044(2) 0.054(2) -0.0119(18) -0.0072(19) -0.0239(19) C23 0.073(2) 0.045(2) 0.0450(19) -0.0112(18) -0.0045(19) -0.027(2) C24 0.051(2) 0.040(2) 0.0409(17) -0.0038(15) -0.0047(16) -0.0252(17) C25 0.0433(19) 0.043(2) 0.0348(16) -0.0058(14) -0.0023(16) -0.0203(16) C26 0.047(2) 0.061(2) 0.0397(17) -0.0123(15) -0.0059(16) -0.0264(18) C27 0.056(2) 0.076(3) 0.0388(17) -0.0188(16) 0.0045(18) -0.030(2) C28 0.047(2) 0.078(3) 0.0441(19) -0.0100(17) 0.0061(18) -0.027(2) C29 0.056(2) 0.096(3) 0.0507(19) -0.0144(19) -0.0029(18) -0.043(2) C30 0.057(2) 0.082(3) 0.0400(18) -0.0184(16) -0.0032(18) -0.030(2) C31 0.063(3) 0.156(4) 0.088(3) -0.025(2) 0.018(2) -0.062(3) C32 0.085(3) 0.055(3) 0.124(3) -0.002(2) -0.010(3) -0.003(2) C33 0.052(2) 0.065(3) 0.0503(19) -0.0100(18) 0.0028(18) -0.026(2) C34 0.082(3) 0.087(3) 0.056(2) 0.001(2) 0.003(2) -0.055(3) C35 0.075(3) 0.140(4) 0.059(2) -0.041(3) 0.025(2) -0.076(3) C36 0.057(3) 0.094(4) 0.100(3) -0.047(3) 0.020(2) -0.034(3) C37 0.050(2) 0.069(3) 0.078(2) -0.021(2) 0.005(2) -0.025(2) C38 0.039(2) 0.054(2) 0.0435(18) -0.0126(17) -0.0041(17) -0.0169(19) C39 0.0418(19) 0.044(2) 0.0563(18) -0.0041(15) -0.0079(17) -0.0149(18) C40 0.045(2) 0.046(2) 0.0392(16) -0.0035(15) -0.0061(16) -0.0249(19) C41 0.059(2) 0.046(2) 0.0536(18) -0.0060(16) -0.0053(17) -0.0203(19) C42 0.073(3) 0.064(3) 0.064(2) -0.0026(19) -0.006(2) -0.049(2) C43 0.051(2) 0.101(4) 0.059(2) -0.017(2) 0.0003(19) -0.052(3) C44 0.043(2) 0.064(3) 0.0555(19) -0.0129(17) -0.0010(16) -0.0204(19) C45 0.041(2) 0.049(2) 0.0359(16) -0.0017(15) -0.0050(15) -0.0222(19) C46 0.0438(19) 0.045(2) 0.0497(18) -0.0055(15) -0.0126(16) -0.0143(17) C47 0.058(2) 0.034(2) 0.0474(19) 0.0036(15) -0.0180(17) -0.0163(18) C48 0.119(3) 0.056(2) 0.057(2) 0.0057(18) -0.021(2) -0.052(2) C49 0.150(4) 0.082(3) 0.072(2) 0.021(2) -0.019(3) -0.083(3) C50 0.105(3) 0.091(3) 0.063(2) 0.018(2) -0.012(2) -0.054(3) C51 0.083(3) 0.080(3) 0.043(2) 0.0004(18) -0.0150(19) -0.035(2) C52 0.061(2) 0.060(2) 0.0506(19) -0.0031(17) -0.0116(18) -0.0300(19) C53 0.045(2) 0.046(2) 0.0351(16) -0.0019(15) -0.0058(16) -0.0254(19) C54 0.060(3) 0.068(3) 0.045(2) -0.0055(19) -0.0033(19) -0.032(2) C55 0.054(2) 0.075(3) 0.0445(19) 0.002(2) 0.000(2) -0.039(2) C56 0.042(2) 0.048(2) 0.0296(15) 0.0055(15) -0.0064(15) -0.0248(18) C57 0.053(2) 0.042(2) 0.054(2) -0.0153(18) -0.0018(19) -0.0182(19) C58 0.077(3) 0.034(2) 0.062(2) -0.0048(18) 0.012(2) -0.0071(19) C59 0.088(3) 0.049(3) 0.063(2) -0.0055(19) 0.013(2) -0.013(2) C60 0.071(3) 0.049(3) 0.070(2) -0.024(2) 0.012(2) -0.019(2) C61 0.064(2) 0.043(2) 0.081(2) -0.025(2) -0.008(2) -0.0063(19) C62 0.074(3) 0.052(3) 0.061(2) -0.0121(19) -0.013(2) -0.013(2) C63 0.077(3) 0.074(3) 0.122(3) -0.042(2) 0.031(2) -0.024(2) C64 0.128(4) 0.156(5) 0.085(3) -0.010(3) -0.002(3) -0.065(4) _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 C11 1.372(3) . ? O1 C32 1.414(3) . ? O2 C28 1.375(3) . ? O2 C31 1.416(3) . ? O3 C22 1.384(3) . ? O3 C23 1.402(3) . ? O4 C23 1.184(3) . ? O5 C22 1.192(3) . ? O6 C64 1.296(4) . ? O6 C43 1.439(4) . ? O7 C60 1.375(3) . ? O7 C63 1.413(3) . ? O8 C54 1.390(3) . ? O8 C55 1.404(3) . ? O9 C55 1.180(3) . ? O10 C54 1.196(3) . ? N1 C21 1.373(3) . ? N1 C8 1.430(3) . ? N1 C7 1.484(3) . ? N2 C24 1.388(3) . ? N2 C25 1.435(3) . ? N2 C14 1.481(3) . ? N3 C56 1.390(3) . ? N3 C40 1.447(3) . ? N3 C39 1.471(3) . ? N4 C53 1.364(3) . ? N4 C57 1.441(3) . ? N4 C46 1.476(3) . ? C1 C6 1.372(3) . ? C1 C2 1.382(4) . ? C2 C3 1.376(4) . ? C3 C4 1.371(4) . ? C4 C5 1.386(4) . ? C5 C6 1.385(3) . ? C6 C7 1.499(3) . ? C8 C9 1.389(3) . ? C8 C13 1.398(3) . ? C9 C10 1.384(3) . ? C10 C11 1.369(3) . ? C11 C12 1.396(4) . ? C12 C13 1.380(3) . ? C13 C14 1.510(3) . ? C14 C15 1.520(3) . ? C15 C16 1.366(3) . ? C15 C20 1.395(3) . ? C16 C17 1.389(4) . ? C17 C18 1.382(4) . ? C18 C19 1.373(4) . ? C19 C20 1.370(4) . ? C21 C24 1.362(3) . ? C21 C22 1.487(3) . ? C23 C24 1.465(3) . ? C25 C30 1.374(3) . ? C25 C26 1.396(3) . ? C26 C27 1.372(3) . ? C27 C28 1.366(3) . ? C28 C29 1.375(3) . ? C29 C30 1.391(3) . ? C33 C38 1.379(3) . ? C33 C34 1.392(3) . ? C34 C35 1.375(4) . ? C35 C36 1.364(4) . ? C36 C37 1.380(4) . ? C37 C38 1.381(3) . ? C38 C39 1.509(3) . ? C40 C45 1.376(3) . ? C40 C41 1.404(3) . ? C41 C42 1.391(3) . ? C42 C43 1.358(4) . ? C43 C44 1.378(4) . ? C44 C45 1.379(3) . ? C45 C46 1.529(3) . ? C46 C47 1.520(3) . ? C47 C48 1.379(3) . ? C47 C52 1.387(3) . ? C48 C49 1.384(4) . ? C49 C50 1.381(4) . ? C50 C51 1.372(4) . ? C51 C52 1.385(3) . ? C53 C56 1.361(3) . ? C53 C54 1.469(4) . ? C55 C56 1.477(4) . ? C57 C62 1.367(3) . ? C57 C58 1.386(3) . ? C58 C59 1.382(4) . ? C59 C60 1.364(4) . ? C60 C61 1.384(4) . ? C61 C62 1.391(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 C11 O1 C32 116.8(3) . . ? C28 O2 C31 118.2(2) . . ? C22 O3 C23 107.6(2) . . ? C64 O6 C43 115.2(3) . . ? C60 O7 C63 119.2(3) . . ? C54 O8 C55 108.1(3) . . ? C21 N1 C8 119.3(2) . . ? C21 N1 C7 119.7(2) . . ? C8 N1 C7 118.9(2) . . ? C24 N2 C25 118.8(2) . . ? C24 N2 C14 116.7(2) . . ? C25 N2 C14 116.6(2) . . ? C56 N3 C40 119.4(2) . . ? C56 N3 C39 119.1(2) . . ? C40 N3 C39 119.1(2) . . ? C53 N4 C57 118.3(2) . . ? C53 N4 C46 118.4(2) . . ? C57 N4 C46 117.7(2) . . ? C6 C1 C2 121.2(3) . . ? C3 C2 C1 119.7(3) . . ? C4 C3 C2 119.5(3) . . ? C3 C4 C5 120.9(3) . . ? C6 C5 C4 119.6(3) . . ? C1 C6 C5 119.0(3) . . ? C1 C6 C7 120.8(3) . . ? C5 C6 C7 119.8(3) . . ? N1 C7 C6 115.0(2) . . ? C9 C8 C13 119.2(3) . . ? C9 C8 N1 119.8(2) . . ? C13 C8 N1 121.0(3) . . ? C10 C9 C8 121.8(3) . . ? C11 C10 C9 119.2(3) . . ? C10 C11 O1 124.8(3) . . ? C10 C11 C12 119.4(3) . . ? O1 C11 C12 115.8(3) . . ? C13 C12 C11 122.1(3) . . ? C12 C13 C8 118.2(3) . . ? C12 C13 C14 117.5(2) . . ? C8 C13 C14 124.3(3) . . ? N2 C14 C13 112.1(2) . . ? N2 C14 C15 113.8(2) . . ? C13 C14 C15 113.2(2) . . ? C16 C15 C20 118.7(3) . . ? C16 C15 C14 123.5(3) . . ? C20 C15 C14 117.7(3) . . ? C15 C16 C17 120.5(3) . . ? C18 C17 C16 120.5(3) . . ? C19 C18 C17 119.0(4) . . ? C20 C19 C18 120.6(3) . . ? C19 C20 C15 120.7(3) . . ? C24 C21 N1 131.3(2) . . ? C24 C21 C22 105.9(2) . . ? N1 C21 C22 122.6(2) . . ? O5 C22 O3 119.8(3) . . ? O5 C22 C21 130.8(3) . . ? O3 C22 C21 109.3(2) . . ? O4 C23 O3 120.1(3) . . ? O4 C23 C24 131.8(3) . . ? O3 C23 C24 108.1(2) . . ? C21 C24 N2 130.6(3) . . ? C21 C24 C23 108.7(2) . . ? N2 C24 C23 120.0(2) . . ? C30 C25 C26 118.3(3) . . ? C30 C25 N2 122.3(2) . . ? C26 C25 N2 119.4(2) . . ? C27 C26 C25 120.0(3) . . ? C28 C27 C26 121.1(2) . . ? C27 C28 C29 120.2(3) . . ? C27 C28 O2 115.0(3) . . ? C29 C28 O2 124.9(3) . . ? C28 C29 C30 118.8(3) . . ? C25 C30 C29 121.6(2) . . ? C38 C33 C34 120.6(3) . . ? C35 C34 C33 120.4(3) . . ? C36 C35 C34 118.8(3) . . ? C35 C36 C37 121.4(4) . . ? C36 C37 C38 120.4(3) . . ? C33 C38 C37 118.4(3) . . ? C33 C38 C39 123.3(3) . . ? C37 C38 C39 118.2(3) . . ? N3 C39 C38 114.7(2) . . ? C45 C40 C41 119.4(3) . . ? C45 C40 N3 122.5(3) . . ? C41 C40 N3 118.0(3) . . ? C42 C41 C40 119.9(3) . . ? C43 C42 C41 119.8(3) . . ? C42 C43 C44 120.3(3) . . ? C42 C43 O6 127.6(4) . . ? C44 C43 O6 112.2(3) . . ? C43 C44 C45 121.0(3) . . ? C40 C45 C44 119.4(3) . . ? C40 C45 C46 123.8(3) . . ? C44 C45 C46 116.8(3) . . ? N4 C46 C47 112.2(2) . . ? N4 C46 C45 111.4(2) . . ? C47 C46 C45 114.9(2) . . ? C48 C47 C52 118.4(3) . . ? C48 C47 C46 121.6(3) . . ? C52 C47 C46 119.8(3) . . ? C47 C48 C49 120.6(3) . . ? C50 C49 C48 120.5(3) . . ? C51 C50 C49 119.2(3) . . ? C50 C51 C52 120.3(3) . . ? C51 C52 C47 120.9(3) . . ? C56 C53 N4 131.4(3) . . ? C56 C53 C54 107.3(3) . . ? N4 C53 C54 121.1(3) . . ? O10 C54 O8 120.6(3) . . ? O10 C54 C53 130.6(4) . . ? O8 C54 C53 108.8(3) . . ? O9 C55 O8 120.3(3) . . ? O9 C55 C56 132.2(3) . . ? O8 C55 C56 107.4(3) . . ? C53 C56 N3 129.1(3) . . ? C53 C56 C55 108.2(3) . . ? N3 C56 C55 122.6(3) . . ? C62 C57 C58 118.9(3) . . ? C62 C57 N4 120.8(3) . . ? C58 C57 N4 120.2(3) . . ? C59 C58 C57 119.7(3) . . ? C60 C59 C58 121.1(3) . . ? C59 C60 O7 116.1(3) . . ? C59 C60 C61 120.0(3) . . ? O7 C60 C61 123.9(3) . . ? C60 C61 C62 118.6(3) . . ? C57 C62 C61 121.7(3) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.308 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.038