# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Jubaraj Baruah' _publ_contact_author_email JUBA@IITG.ERNET.IN _publ_section_title ; Different spatial orientations of amide derivatives on anion coordination ; loop_ _publ_author_name 'Jubaraj Baruah' 'Dipjyoti Kalita' # Attachment 'IV.cif' data_8aq8hqbf4_0m _database_code_depnum_ccdc_archive 'CCDC 724792' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H25 B F4 N4 O4' _chemical_formula_weight 508.28 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' B B 0.0013 0.0007 '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 Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.7700(3) _cell_length_b 11.7365(5) _cell_length_c 30.6874(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2438.30(18) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2277 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 24.83 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 18108 _diffrn_reflns_av_R_equivalents 0.0629 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4444 _reflns_number_gt 2775 _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^)+(0.1135P)^2^+0.1349P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.1(18) _refine_ls_number_reflns 4444 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1038 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.2012 _refine_ls_wR_factor_gt 0.1682 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 B1 B 0.0293(12) 0.7606(5) 0.8182(2) 0.094(2) Uani 1 1 d . . . C20 C 0.6136(5) 0.2534(3) 1.11518(10) 0.0432(8) Uani 1 1 d . . . C12 C 0.6135(6) 0.1852(3) 1.07755(11) 0.0470(8) Uani 1 1 d . . . C13 C 0.6190(6) 0.0688(3) 1.08175(12) 0.0557(9) Uani 1 1 d . . . H13 H 0.6205 0.0231 1.0570 0.067 Uiso 1 1 calc R . . C14 C 0.6223(7) 0.0188(3) 1.12296(13) 0.0604(10) Uani 1 1 d . . . H14 H 0.6251 -0.0602 1.1253 0.073 Uiso 1 1 calc R . . C15 C 0.6216(6) 0.0834(3) 1.15977(13) 0.0589(10) Uani 1 1 d . . . H15 H 0.6223 0.0484 1.1870 0.071 Uiso 1 1 calc R . . C16 C 0.6198(6) 0.2026(3) 1.15678(11) 0.0517(9) Uani 1 1 d . . . C17 C 0.6177(6) 0.2766(4) 1.19344(11) 0.0576(10) Uani 1 1 d . . . H17 H 0.6212 0.2462 1.2214 0.069 Uiso 1 1 calc R . . C18 C 0.6108(6) 0.3901(4) 1.18809(13) 0.0637(11) Uani 1 1 d . . . H18 H 0.6099 0.4377 1.2123 0.076 Uiso 1 1 calc R . . C19 C 0.6050(6) 0.4367(4) 1.14647(12) 0.0572(10) Uani 1 1 d . . . H19 H 0.5994 0.5153 1.1429 0.069 Uiso 1 1 calc R . . C11 C 0.6083(6) 0.1774(3) 1.00025(10) 0.0486(8) Uani 1 1 d . . . H11A H 0.4909 0.1301 0.9994 0.058 Uiso 1 1 calc R . . H11B H 0.7234 0.1282 0.9994 0.058 Uiso 1 1 calc R . . C10 C 0.6105(5) 0.2576(3) 0.96198(11) 0.0468(8) Uani 1 1 d . . . C2 C 0.6134(6) 0.2452(3) 0.88097(11) 0.0501(9) Uani 1 1 d . . . C3 C 0.6238(7) 0.3588(4) 0.87039(13) 0.0633(10) Uani 1 1 d . . . H3 H 0.6233 0.4137 0.8922 0.076 Uiso 1 1 calc R . . C4 C 0.6352(7) 0.3919(5) 0.82642(16) 0.0754(13) Uani 1 1 d . . . H4 H 0.6437 0.4689 0.8196 0.090 Uiso 1 1 calc R . . C5 C 0.6342(7) 0.3134(5) 0.79353(15) 0.0818(14) Uani 1 1 d . . . H5 H 0.6415 0.3372 0.7647 0.098 Uiso 1 1 calc R . . C6 C 0.6220(6) 0.1969(5) 0.80341(13) 0.0722(13) Uani 1 1 d . . . C7 C 0.6223(8) 0.1055(6) 0.77184(15) 0.0902(16) Uani 1 1 d . . . H7 H 0.6252 0.1221 0.7422 0.108 Uiso 1 1 calc R . . C8 C 0.6186(9) -0.0024(6) 0.78514(18) 0.0981(17) Uani 1 1 d . . . H8 H 0.6245 -0.0609 0.7647 0.118 Uiso 1 1 calc R . . C9 C 0.6061(7) -0.0282(4) 0.82850(17) 0.0852(15) Uani 1 1 d . . . H9 H 0.5996 -0.1046 0.8365 0.102 Uiso 1 1 calc R . . C1 C 0.6127(6) 0.1617(4) 0.84772(11) 0.0551(9) Uani 1 1 d . . . C21 C 0.0857(12) 0.6321(6) 0.0563(2) 0.114(2) Uani 1 1 d . . . H21 H -0.0306 0.6044 0.0684 0.136 Uiso 1 1 calc R . . C22 C 0.3038(12) 0.7833(6) 0.0450(3) 0.142(3) Uani 1 1 d . . . H22A H 0.4131 0.7494 0.0601 0.212 Uiso 1 1 calc R . . H22B H 0.3058 0.8643 0.0493 0.212 Uiso 1 1 calc R . . H22C H 0.3140 0.7668 0.0144 0.212 Uiso 1 1 calc R . . C23 C 0.0142(16) 0.8169(6) 0.0875(3) 0.175(4) Uani 1 1 d . . . H23A H -0.1195 0.7915 0.0913 0.263 Uiso 1 1 calc R . . H23B H 0.0144 0.8895 0.0731 0.263 Uiso 1 1 calc R . . H23C H 0.0765 0.8241 0.1155 0.263 Uiso 1 1 calc R . . F1 F -0.0074(9) 0.7862(4) 0.85880(11) 0.174(2) Uani 1 1 d . . . F2 F 0.0210(7) 0.8469(2) 0.79068(10) 0.1290(16) Uani 1 1 d . . . F3 F -0.0482(14) 0.6707(4) 0.80163(16) 0.248(4) Uani 1 1 d . . . F4 F 0.2236(10) 0.7201(6) 0.82057(18) 0.214(3) Uani 1 1 d . . . H3A H 0.603(9) 0.453(5) 0.016(2) 0.113(19) Uiso 1 1 d . . . H3B H 0.472(11) 0.520(6) 0.035(2) 0.14(3) Uiso 1 1 d . . . N3 N 0.6074(5) 0.3692(2) 1.11192(9) 0.0470(7) Uani 1 1 d . . . N2 N 0.6107(5) 0.2013(3) 0.92357(10) 0.0504(7) Uani 1 1 d . . . N1 N 0.6029(6) 0.0505(3) 0.86015(11) 0.0674(9) Uani 1 1 d . . . N4 N 0.1190(8) 0.7368(3) 0.06191(13) 0.0828(11) Uani 1 1 d . . . O2 O 0.6099(4) 0.24415(19) 1.03890(7) 0.0521(6) Uani 1 1 d . . . O1 O 0.6108(5) 0.3616(2) 0.96539(8) 0.0624(7) Uani 1 1 d . . . O4 O 0.1878(6) 0.5621(3) 0.03681(15) 0.1152(14) Uani 1 1 d . . . O3 O 0.5850(7) 0.5002(3) 0.03899(11) 0.0738(9) Uani 1 1 d . . . H3N H 0.615(7) 0.408(4) 1.0814(15) 0.084(14) Uiso 1 1 d . . . H2N H 0.599(7) 0.133(4) 0.9249(13) 0.065(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.149(6) 0.052(3) 0.082(5) -0.007(3) 0.014(4) 0.021(4) C20 0.0347(16) 0.051(2) 0.044(2) 0.0000(16) 0.0017(17) 0.0014(18) C12 0.0473(19) 0.0482(19) 0.046(2) 0.0002(16) 0.0037(19) 0.0015(18) C13 0.061(2) 0.049(2) 0.057(2) -0.0058(17) 0.003(2) 0.004(2) C14 0.071(2) 0.043(2) 0.068(3) 0.0104(19) 0.007(2) 0.007(2) C15 0.062(2) 0.061(2) 0.054(2) 0.0145(19) 0.005(2) 0.002(2) C16 0.0378(18) 0.070(2) 0.048(2) 0.0021(18) 0.0040(18) 0.0002(19) C17 0.047(2) 0.083(3) 0.043(2) -0.0041(19) 0.0029(19) 0.003(2) C18 0.049(2) 0.088(3) 0.055(2) -0.023(2) 0.003(2) -0.006(2) C19 0.048(2) 0.064(2) 0.060(3) -0.014(2) 0.004(2) -0.006(2) C11 0.0482(19) 0.049(2) 0.048(2) -0.0109(16) -0.0003(19) 0.0026(18) C10 0.0404(17) 0.057(2) 0.0429(19) -0.0035(16) 0.0027(19) 0.0049(18) C2 0.0382(17) 0.068(3) 0.044(2) -0.0017(18) -0.0020(18) 0.006(2) C3 0.055(2) 0.079(3) 0.056(2) 0.005(2) 0.002(2) 0.012(2) C4 0.063(3) 0.091(3) 0.072(3) 0.020(3) -0.007(2) 0.013(3) C5 0.060(3) 0.129(5) 0.056(3) 0.020(3) -0.002(2) 0.019(3) C6 0.042(2) 0.124(4) 0.050(2) -0.008(3) -0.004(2) 0.004(3) C7 0.061(3) 0.160(5) 0.050(3) -0.035(3) -0.003(2) 0.011(4) C8 0.080(3) 0.141(5) 0.073(4) -0.052(4) -0.001(3) -0.006(4) C9 0.065(3) 0.100(4) 0.090(4) -0.044(3) 0.010(3) -0.004(3) C1 0.0394(18) 0.080(3) 0.046(2) -0.0079(18) -0.0050(17) 0.001(2) C21 0.122(5) 0.094(4) 0.125(5) 0.003(4) -0.002(4) 0.010(4) C22 0.137(6) 0.112(5) 0.175(7) 0.026(5) -0.008(5) -0.018(5) C23 0.263(12) 0.107(5) 0.156(6) -0.006(5) 0.072(7) 0.086(6) F1 0.315(7) 0.135(3) 0.071(2) 0.010(2) 0.048(3) 0.038(4) F2 0.237(5) 0.0695(18) 0.0808(19) 0.0112(16) 0.020(2) 0.025(2) F3 0.472(13) 0.127(3) 0.146(4) 0.045(3) -0.111(6) -0.129(5) F4 0.204(5) 0.282(7) 0.157(4) 0.049(5) 0.016(4) 0.078(6) N3 0.0441(16) 0.0471(17) 0.0498(17) -0.0076(14) 0.0011(15) -0.0055(15) N2 0.0566(18) 0.0511(19) 0.0436(17) -0.0042(15) -0.0008(16) 0.0022(17) N1 0.0583(19) 0.081(3) 0.063(2) -0.0249(18) 0.0009(18) -0.004(2) N4 0.109(3) 0.046(2) 0.094(3) -0.0075(19) -0.003(3) 0.005(2) O2 0.0705(15) 0.0410(12) 0.0447(14) -0.0030(11) 0.0042(14) 0.0025(13) O1 0.0856(18) 0.0495(15) 0.0521(15) -0.0045(12) -0.0042(16) 0.0051(15) O4 0.118(3) 0.083(2) 0.145(3) -0.053(2) -0.004(3) 0.025(2) O3 0.103(3) 0.0542(16) 0.064(2) -0.0046(16) 0.000(2) 0.0060(19) _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 B1 F3 1.283(8) . ? B1 F1 1.307(7) . ? B1 F2 1.319(7) . ? B1 F4 1.401(9) . ? C20 N3 1.364(4) . ? C20 C12 1.405(5) . ? C20 C16 1.410(5) . ? C12 C13 1.372(5) . ? C12 O2 1.373(4) . ? C13 C14 1.395(5) . ? C13 H13 0.9300 . ? C14 C15 1.361(5) . ? C14 H14 0.9300 . ? C15 C16 1.402(6) . ? C15 H15 0.9300 . ? C16 C17 1.421(5) . ? C17 C18 1.342(6) . ? C17 H17 0.9300 . ? C18 C19 1.390(5) . ? C18 H18 0.9300 . ? C19 N3 1.323(4) . ? C19 H19 0.9300 . ? C11 O2 1.421(4) . ? C11 C10 1.505(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C10 O1 1.225(4) . ? C10 N2 1.351(5) . ? C2 C3 1.374(6) . ? C2 N2 1.405(5) . ? C2 C1 1.414(5) . ? C3 C4 1.406(6) . ? C3 H3 0.9300 . ? C4 C5 1.366(7) . ? C4 H4 0.9300 . ? C5 C6 1.403(8) . ? C5 H5 0.9300 . ? C6 C1 1.423(6) . ? C6 C7 1.446(7) . ? C7 C8 1.331(8) . ? C7 H7 0.9300 . ? C8 C9 1.367(8) . ? C8 H8 0.9300 . ? C9 N1 1.341(5) . ? C9 H9 0.9300 . ? C1 N1 1.361(5) . ? C21 O4 1.229(7) . ? C21 N4 1.261(7) . ? C21 H21 0.9300 . ? C22 N4 1.461(8) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 N4 1.416(7) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? N3 H3N 1.04(5) . ? N2 H2N 0.81(4) . ? O3 H3A 0.92(7) . ? O3 H3B 0.81(8) . ? 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 F3 B1 F1 119.3(7) . . ? F3 B1 F2 111.2(6) . . ? F1 B1 F2 115.2(5) . . ? F3 B1 F4 97.2(7) . . ? F1 B1 F4 101.9(6) . . ? F2 B1 F4 109.5(6) . . ? N3 C20 C12 120.5(3) . . ? N3 C20 C16 119.3(3) . . ? C12 C20 C16 120.2(3) . . ? C13 C12 O2 125.7(3) . . ? C13 C12 C20 119.3(3) . . ? O2 C12 C20 115.0(3) . . ? C12 C13 C14 120.3(3) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 121.2(3) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C16 120.1(3) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C20 118.8(3) . . ? C15 C16 C17 123.9(4) . . ? C20 C16 C17 117.3(3) . . ? C18 C17 C16 120.6(4) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 120.2(4) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? N3 C19 C18 120.0(4) . . ? N3 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? O2 C11 C10 107.9(3) . . ? O2 C11 H11A 110.1 . . ? C10 C11 H11A 110.1 . . ? O2 C11 H11B 110.1 . . ? C10 C11 H11B 110.1 . . ? H11A C11 H11B 108.4 . . ? O1 C10 N2 124.2(3) . . ? O1 C10 C11 123.8(3) . . ? N2 C10 C11 112.0(3) . . ? C3 C2 N2 125.2(3) . . ? C3 C2 C1 120.1(3) . . ? N2 C2 C1 114.7(3) . . ? C2 C3 C4 119.8(4) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 121.5(5) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C4 C5 C6 119.8(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 119.5(4) . . ? C5 C6 C7 125.4(5) . . ? C1 C6 C7 115.1(5) . . ? C8 C7 C6 120.1(5) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.7(5) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? N1 C9 C8 123.6(5) . . ? N1 C9 H9 118.2 . . ? C8 C9 H9 118.2 . . ? N1 C1 C2 117.5(3) . . ? N1 C1 C6 123.3(4) . . ? C2 C1 C6 119.2(4) . . ? O4 C21 N4 128.1(7) . . ? O4 C21 H21 115.9 . . ? N4 C21 H21 115.9 . . ? N4 C22 H22A 109.5 . . ? N4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N4 C23 H23A 109.5 . . ? N4 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N4 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C19 N3 C20 122.5(3) . . ? C19 N3 H3N 117(2) . . ? C20 N3 H3N 120(2) . . ? C10 N2 C2 129.2(3) . . ? C10 N2 H2N 116(3) . . ? C2 N2 H2N 114(3) . . ? C9 N1 C1 117.2(4) . . ? C21 N4 C23 129.3(7) . . ? C21 N4 C22 118.0(6) . . ? C23 N4 C22 112.2(6) . . ? C12 O2 C11 116.3(2) . . ? H3A O3 H3B 100(6) . . ? 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 N3 C20 C12 C13 -179.7(4) . . . . ? C16 C20 C12 C13 0.2(6) . . . . ? N3 C20 C12 O2 0.9(5) . . . . ? C16 C20 C12 O2 -179.2(3) . . . . ? O2 C12 C13 C14 180.0(4) . . . . ? C20 C12 C13 C14 0.7(7) . . . . ? C12 C13 C14 C15 -0.4(7) . . . . ? C13 C14 C15 C16 -0.7(7) . . . . ? C14 C15 C16 C20 1.6(6) . . . . ? C14 C15 C16 C17 179.6(4) . . . . ? N3 C20 C16 C15 178.6(4) . . . . ? C12 C20 C16 C15 -1.3(6) . . . . ? N3 C20 C16 C17 0.5(6) . . . . ? C12 C20 C16 C17 -179.4(4) . . . . ? C15 C16 C17 C18 -178.2(4) . . . . ? C20 C16 C17 C18 -0.2(6) . . . . ? C16 C17 C18 C19 0.2(7) . . . . ? C17 C18 C19 N3 -0.4(7) . . . . ? O2 C11 C10 O1 -0.9(5) . . . . ? O2 C11 C10 N2 179.5(3) . . . . ? N2 C2 C3 C4 176.9(4) . . . . ? C1 C2 C3 C4 -0.5(7) . . . . ? C2 C3 C4 C5 0.7(7) . . . . ? C3 C4 C5 C6 -0.2(7) . . . . ? C4 C5 C6 C1 -0.6(7) . . . . ? C4 C5 C6 C7 -179.1(4) . . . . ? C5 C6 C7 C8 177.1(6) . . . . ? C1 C6 C7 C8 -1.5(7) . . . . ? C6 C7 C8 C9 2.7(9) . . . . ? C7 C8 C9 N1 -2.0(9) . . . . ? C3 C2 C1 N1 179.8(4) . . . . ? N2 C2 C1 N1 2.2(5) . . . . ? C3 C2 C1 C6 -0.3(6) . . . . ? N2 C2 C1 C6 -177.9(4) . . . . ? C5 C6 C1 N1 -179.3(4) . . . . ? C7 C6 C1 N1 -0.6(7) . . . . ? C5 C6 C1 C2 0.8(7) . . . . ? C7 C6 C1 C2 179.5(4) . . . . ? C18 C19 N3 C20 0.6(6) . . . . ? C12 C20 N3 C19 179.2(3) . . . . ? C16 C20 N3 C19 -0.7(6) . . . . ? O1 C10 N2 C2 0.7(6) . . . . ? C11 C10 N2 C2 -179.7(4) . . . . ? C3 C2 N2 C10 2.6(7) . . . . ? C1 C2 N2 C10 -180.0(4) . . . . ? C8 C9 N1 C1 0.0(7) . . . . ? C2 C1 N1 C9 -178.7(4) . . . . ? C6 C1 N1 C9 1.3(7) . . . . ? O4 C21 N4 C23 -173.5(8) . . . . ? O4 C21 N4 C22 -2.4(10) . . . . ? C13 C12 O2 C11 1.1(5) . . . . ? C20 C12 O2 C11 -179.6(3) . . . . ? C10 C11 O2 C12 -178.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.345 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.058 # Attachment 'V.cif' data_8aq8hqhclo4_0m _database_code_depnum_ccdc_archive 'CCDC 724793' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H17 Cl2 N3 O10' _chemical_formula_weight 530.27 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 '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 9.4742(9) _cell_length_b 10.6945(14) _cell_length_c 21.747(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.662(5) _cell_angle_gamma 90.00 _cell_volume 2203.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1826 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.360 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 13693 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 24.24 _reflns_number_total 3377 _reflns_number_gt 2194 _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^)+(0.1319P)^2^+2.9273P] 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 3377 _refine_ls_number_parameters 324 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1233 _refine_ls_R_factor_gt 0.0836 _refine_ls_wR_factor_ref 0.2478 _refine_ls_wR_factor_gt 0.2197 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 C1 C -0.0687(5) -0.0305(6) 0.1636(2) 0.0478(14) Uani 1 1 d . . . C2 C -0.0029(6) -0.1049(6) 0.1190(3) 0.0512(15) Uani 1 1 d . . . C3 C -0.0201(6) -0.2319(7) 0.1206(3) 0.0628(17) Uani 1 1 d . . . H3 H 0.0231 -0.2817 0.0912 0.075 Uiso 1 1 calc R . . C4 C -0.1037(7) -0.2878(7) 0.1669(3) 0.0693(19) Uani 1 1 d . . . H4 H -0.1127 -0.3743 0.1683 0.083 Uiso 1 1 calc R . . C5 C -0.1701(7) -0.2174(7) 0.2089(3) 0.0687(19) Uani 1 1 d . . . H5 H -0.2258 -0.2555 0.2384 0.082 Uiso 1 1 calc R . . C6 C -0.1557(6) -0.0857(6) 0.2083(3) 0.0568(16) Uani 1 1 d . . . C7 C -0.2234(7) -0.0051(8) 0.2500(3) 0.0672(19) Uani 1 1 d . . . H7 H -0.2813 -0.0389 0.2799 0.081 Uiso 1 1 calc R . . C8 C -0.2062(7) 0.1195(9) 0.2474(3) 0.072(2) Uani 1 1 d . . . H8 H -0.2529 0.1713 0.2748 0.087 Uiso 1 1 calc R . . C9 C -0.1175(6) 0.1706(7) 0.2031(3) 0.0615(17) Uani 1 1 d . . . H9 H -0.1034 0.2566 0.2013 0.074 Uiso 1 1 calc R . . C10 C 0.1423(6) -0.1090(7) 0.0301(3) 0.0649(18) Uani 1 1 d . . . H10A H 0.0730 -0.1468 0.0027 0.078 Uiso 1 1 calc R . . H10B H 0.1957 -0.1758 0.0495 0.078 Uiso 1 1 calc R . . C11 C 0.2407(6) -0.0292(6) -0.0068(3) 0.0553(16) Uani 1 1 d . . . C12 C 0.3769(6) 0.1646(6) -0.0075(3) 0.0522(15) Uani 1 1 d . . . C13 C 0.3884(6) 0.1838(7) -0.0697(3) 0.0593(17) Uani 1 1 d . . . H13 H 0.3328 0.1368 -0.0966 0.071 Uiso 1 1 calc R . . C14 C 0.4817(7) 0.2725(7) -0.0935(3) 0.0665(18) Uani 1 1 d . . . H14 H 0.4874 0.2826 -0.1359 0.080 Uiso 1 1 calc R . . C15 C 0.5636(7) 0.3438(7) -0.0565(3) 0.0625(18) Uani 1 1 d . . . H15 H 0.6234 0.4034 -0.0731 0.075 Uiso 1 1 calc R . . C16 C 0.5577(6) 0.3269(6) 0.0084(3) 0.0557(16) Uani 1 1 d . . . C17 C 0.6430(7) 0.3951(7) 0.0505(3) 0.0674(18) Uani 1 1 d . . . H17 H 0.7059 0.4546 0.0359 0.081 Uiso 1 1 calc R . . C18 C 0.6338(7) 0.3746(7) 0.1122(3) 0.0697(19) Uani 1 1 d . . . H18 H 0.6875 0.4218 0.1397 0.084 Uiso 1 1 calc R . . C19 C 0.5442(6) 0.2832(7) 0.1333(3) 0.0590(16) Uani 1 1 d . . . H19 H 0.5395 0.2668 0.1752 0.071 Uiso 1 1 calc R . . C20 C 0.4649(5) 0.2360(5) 0.0317(2) 0.0441(13) Uani 1 1 d . . . Cl1 Cl 0.10002(17) 0.37140(16) 0.08324(8) 0.0646(5) Uani 1 1 d . . . Cl2 Cl 0.35485(17) 0.98229(16) 0.21662(7) 0.0619(5) Uani 1 1 d . . . H1 H -0.013(7) 0.131(7) 0.138(3) 0.07(2) Uiso 1 1 d . . . H3N H 0.417(6) 0.152(6) 0.110(3) 0.055(17) Uiso 1 1 d . . . N1 N -0.0535(5) 0.0954(5) 0.1637(3) 0.0504(13) Uani 1 1 d . . . N2 N 0.2811(5) 0.0810(5) 0.0180(2) 0.0599(14) Uani 1 1 d . . . H2 H 0.2445 0.1013 0.0526 0.072 Uiso 1 1 calc R . . N3 N 0.4654(5) 0.2190(5) 0.0945(2) 0.0509(12) Uani 1 1 d . . . O1 O 0.0712(4) -0.0393(4) 0.07617(19) 0.0631(12) Uani 1 1 d . . . O2 O 0.2836(5) -0.0713(5) -0.0549(2) 0.0777(14) Uani 1 1 d . . . O3 O 0.1440(5) 0.2539(5) 0.1082(3) 0.1000(18) Uani 1 1 d . . . O4 O 0.1117(15) 0.3691(10) 0.0207(3) 0.215(5) Uani 1 1 d . . . O5 O 0.1983(11) 0.4581(9) 0.0981(5) 0.192(4) Uani 1 1 d . . . O6 O -0.0230(8) 0.4039(10) 0.1095(5) 0.207(5) Uani 1 1 d . . . O7 O 0.2233(5) 0.9619(6) 0.2458(3) 0.0963(18) Uani 1 1 d . . . O8 O 0.4273(6) 1.0819(7) 0.2475(3) 0.121(2) Uani 1 1 d . . . O9 O 0.3333(7) 1.0118(8) 0.1545(3) 0.139(3) Uani 1 1 d . . . O10 O 0.4417(7) 0.8765(6) 0.2238(3) 0.117(2) 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 C1 0.045(3) 0.050(5) 0.047(3) 0.009(3) -0.007(2) -0.001(3) C2 0.058(3) 0.042(4) 0.054(4) 0.007(3) 0.001(3) -0.004(3) C3 0.068(4) 0.047(5) 0.073(4) -0.003(3) -0.004(3) -0.001(3) C4 0.076(4) 0.044(5) 0.088(5) 0.017(4) -0.003(4) -0.017(3) C5 0.066(4) 0.064(6) 0.076(5) 0.019(4) -0.004(3) -0.019(3) C6 0.056(4) 0.055(5) 0.059(4) 0.014(3) -0.004(3) -0.007(3) C7 0.065(4) 0.073(6) 0.065(4) 0.007(4) 0.011(3) -0.014(3) C8 0.067(4) 0.096(7) 0.053(4) -0.008(4) 0.015(3) 0.001(4) C9 0.066(4) 0.051(5) 0.067(4) -0.004(3) -0.006(3) 0.004(3) C10 0.057(4) 0.057(5) 0.081(5) -0.009(3) 0.011(3) 0.006(3) C11 0.057(4) 0.061(5) 0.048(4) -0.009(3) -0.003(3) 0.012(3) C12 0.057(3) 0.056(5) 0.044(3) -0.004(3) 0.009(3) 0.004(3) C13 0.070(4) 0.065(5) 0.044(4) -0.001(3) 0.003(3) 0.002(3) C14 0.086(5) 0.075(6) 0.038(3) 0.006(3) 0.015(3) 0.010(4) C15 0.073(4) 0.058(5) 0.057(4) 0.019(3) 0.019(3) 0.003(3) C16 0.060(4) 0.042(4) 0.065(4) -0.001(3) 0.008(3) 0.007(3) C17 0.063(4) 0.056(5) 0.083(5) 0.004(3) 0.007(3) -0.008(3) C18 0.075(4) 0.058(5) 0.076(5) -0.007(4) -0.006(3) -0.006(3) C19 0.067(4) 0.058(5) 0.052(4) -0.004(3) 0.000(3) 0.001(3) C20 0.053(3) 0.038(4) 0.042(3) 0.004(2) 0.006(2) 0.004(2) Cl1 0.0722(11) 0.0422(11) 0.0798(12) 0.0004(8) 0.0148(8) -0.0051(8) Cl2 0.0794(11) 0.0498(11) 0.0567(10) 0.0072(7) 0.0084(8) 0.0080(8) N1 0.056(3) 0.043(4) 0.052(3) 0.003(2) 0.001(2) -0.006(2) N2 0.083(4) 0.053(4) 0.043(3) -0.005(2) 0.016(2) -0.012(3) N3 0.056(3) 0.051(4) 0.046(3) -0.001(2) 0.006(2) 0.002(2) O1 0.080(3) 0.045(3) 0.065(3) -0.005(2) 0.021(2) -0.001(2) O2 0.088(3) 0.072(4) 0.072(3) -0.015(3) 0.013(3) 0.009(3) O3 0.107(4) 0.057(4) 0.137(5) 0.024(3) 0.052(3) 0.009(3) O4 0.424(16) 0.146(9) 0.074(5) 0.004(5) -0.002(7) 0.045(9) O5 0.219(9) 0.143(9) 0.215(10) 0.013(7) -0.007(7) -0.103(7) O6 0.123(6) 0.174(9) 0.326(13) 0.114(9) 0.116(7) 0.076(6) O7 0.080(3) 0.111(5) 0.098(4) 0.000(3) 0.022(3) -0.017(3) O8 0.097(4) 0.102(6) 0.164(6) -0.049(4) 0.014(4) -0.015(4) O9 0.150(6) 0.171(8) 0.096(4) 0.078(5) -0.031(4) -0.048(5) O10 0.146(5) 0.089(5) 0.116(5) 0.004(3) 0.010(4) 0.041(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 C1 N1 1.354(8) . ? C1 C2 1.406(8) . ? C1 C6 1.411(8) . ? C2 O1 1.368(7) . ? C2 C3 1.368(9) . ? C3 C4 1.421(9) . ? C3 H3 0.9300 . ? C4 C5 1.344(10) . ? C4 H4 0.9300 . ? C5 C6 1.416(10) . ? C5 H5 0.9300 . ? C6 C7 1.410(10) . ? C7 C8 1.344(10) . ? C7 H7 0.9300 . ? C8 C9 1.396(9) . ? C8 H8 0.9300 . ? C9 N1 1.326(8) . ? C9 H9 0.9300 . ? C10 O1 1.425(7) . ? C10 C11 1.503(9) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O2 1.213(7) . ? C11 N2 1.350(8) . ? C12 C13 1.375(8) . ? C12 N2 1.394(8) . ? C12 C20 1.410(8) . ? C13 C14 1.400(9) . ? C13 H13 0.9300 . ? C14 C15 1.348(9) . ? C14 H14 0.9300 . ? C15 C16 1.424(8) . ? C15 H15 0.9300 . ? C16 C20 1.409(8) . ? C16 C17 1.416(9) . ? C17 C18 1.363(9) . ? C17 H17 0.9300 . ? C18 C19 1.377(9) . ? C18 H18 0.9300 . ? C19 N3 1.315(8) . ? C19 H19 0.9300 . ? C20 N3 1.377(7) . ? Cl1 O6 1.350(7) . ? Cl1 O5 1.350(8) . ? Cl1 O4 1.366(7) . ? Cl1 O3 1.430(5) . ? Cl2 O9 1.401(6) . ? Cl2 O10 1.407(6) . ? Cl2 O7 1.422(5) . ? Cl2 O8 1.431(6) . ? N1 H1 0.77(7) . ? N2 H2 0.8600 . ? N3 H3N 0.92(6) . ? 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 N1 C1 C2 121.1(5) . . ? N1 C1 C6 118.5(6) . . ? C2 C1 C6 120.4(6) . . ? O1 C2 C3 126.1(6) . . ? O1 C2 C1 114.5(6) . . ? C3 C2 C1 119.4(6) . . ? C2 C3 C4 120.2(6) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 121.0(7) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 120.4(7) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C1 117.4(6) . . ? C7 C6 C5 124.0(6) . . ? C1 C6 C5 118.6(6) . . ? C8 C7 C6 121.5(6) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C7 C8 C9 119.4(7) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? N1 C9 C8 119.4(7) . . ? N1 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? O1 C10 C11 112.3(6) . . ? O1 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? O1 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? O2 C11 N2 125.0(6) . . ? O2 C11 C10 117.7(6) . . ? N2 C11 C10 117.1(5) . . ? C13 C12 N2 123.2(5) . . ? C13 C12 C20 117.5(6) . . ? N2 C12 C20 119.3(5) . . ? C12 C13 C14 121.5(6) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C15 C14 C13 121.5(6) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C14 C15 C16 119.5(6) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C20 C16 C17 118.5(6) . . ? C20 C16 C15 118.4(6) . . ? C17 C16 C15 123.1(6) . . ? C18 C17 C16 120.7(6) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 119.3(6) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? N3 C19 C18 120.3(6) . . ? N3 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? N3 C20 C16 116.9(5) . . ? N3 C20 C12 121.5(5) . . ? C16 C20 C12 121.6(5) . . ? O6 Cl1 O5 108.6(8) . . ? O6 Cl1 O4 120.4(8) . . ? O5 Cl1 O4 100.7(7) . . ? O6 Cl1 O3 108.3(4) . . ? O5 Cl1 O3 108.4(5) . . ? O4 Cl1 O3 109.7(5) . . ? O9 Cl2 O10 111.6(5) . . ? O9 Cl2 O7 110.3(4) . . ? O10 Cl2 O7 110.0(4) . . ? O9 Cl2 O8 110.4(5) . . ? O10 Cl2 O8 105.6(4) . . ? O7 Cl2 O8 108.8(4) . . ? C9 N1 C1 123.7(6) . . ? C9 N1 H1 113(6) . . ? C1 N1 H1 123(6) . . ? C11 N2 C12 125.7(5) . . ? C11 N2 H2 117.2 . . ? C12 N2 H2 117.2 . . ? C19 N3 C20 124.2(6) . . ? C19 N3 H3N 117(4) . . ? C20 N3 H3N 119(4) . . ? C2 O1 C10 117.5(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 N1 C1 C2 O1 -2.1(8) . . . . ? C6 C1 C2 O1 176.1(5) . . . . ? N1 C1 C2 C3 179.7(5) . . . . ? C6 C1 C2 C3 -2.2(8) . . . . ? O1 C2 C3 C4 -178.1(5) . . . . ? C1 C2 C3 C4 0.0(9) . . . . ? C2 C3 C4 C5 1.7(10) . . . . ? C3 C4 C5 C6 -1.2(10) . . . . ? N1 C1 C6 C7 1.0(8) . . . . ? C2 C1 C6 C7 -177.3(5) . . . . ? N1 C1 C6 C5 -179.1(5) . . . . ? C2 C1 C6 C5 2.7(8) . . . . ? C4 C5 C6 C7 178.9(6) . . . . ? C4 C5 C6 C1 -1.0(9) . . . . ? C1 C6 C7 C8 0.0(9) . . . . ? C5 C6 C7 C8 -179.9(6) . . . . ? C6 C7 C8 C9 -1.0(10) . . . . ? C7 C8 C9 N1 1.1(10) . . . . ? O1 C10 C11 O2 -164.8(5) . . . . ? O1 C10 C11 N2 19.2(8) . . . . ? N2 C12 C13 C14 177.2(6) . . . . ? C20 C12 C13 C14 -1.2(9) . . . . ? C12 C13 C14 C15 -0.6(10) . . . . ? C13 C14 C15 C16 1.4(10) . . . . ? C14 C15 C16 C20 -0.4(9) . . . . ? C14 C15 C16 C17 178.1(6) . . . . ? C20 C16 C17 C18 -1.0(10) . . . . ? C15 C16 C17 C18 -179.5(6) . . . . ? C16 C17 C18 C19 2.4(10) . . . . ? C17 C18 C19 N3 -2.0(10) . . . . ? C17 C16 C20 N3 -0.8(8) . . . . ? C15 C16 C20 N3 177.8(5) . . . . ? C17 C16 C20 C12 -180.0(6) . . . . ? C15 C16 C20 C12 -1.4(9) . . . . ? C13 C12 C20 N3 -177.0(5) . . . . ? N2 C12 C20 N3 4.5(9) . . . . ? C13 C12 C20 C16 2.2(9) . . . . ? N2 C12 C20 C16 -176.3(5) . . . . ? C8 C9 N1 C1 -0.1(9) . . . . ? C2 C1 N1 C9 177.3(5) . . . . ? C6 C1 N1 C9 -1.0(8) . . . . ? O2 C11 N2 C12 0.8(10) . . . . ? C10 C11 N2 C12 176.5(6) . . . . ? C13 C12 N2 C11 34.9(9) . . . . ? C20 C12 N2 C11 -146.8(6) . . . . ? C18 C19 N3 C20 0.1(10) . . . . ? C16 C20 N3 C19 1.3(8) . . . . ? C12 C20 N3 C19 -179.5(6) . . . . ? C3 C2 O1 C10 -2.8(8) . . . . ? C1 C2 O1 C10 179.1(5) . . . . ? C11 C10 O1 C2 -169.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 24.24 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.622 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.072 # Attachment 'I.cif' data_meoet8aq1 _database_code_depnum_ccdc_archive 'CCDC 724794' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 N3 O2' _chemical_formula_weight 335.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pna2(1) ' 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' _cell_length_a 14.6536(8) _cell_length_b 22.5764(12) _cell_length_c 5.3987(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1786.03(17) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2072 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 20.92 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 12777 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.1135 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3166 _reflns_number_gt 2241 _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^)+(0.0000P)^2^+0.4688P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(3) _refine_ls_number_reflns 3166 _refine_ls_number_parameters 235 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0917 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.1687 _refine_ls_wR_factor_gt 0.1470 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 C1 C 0.5704(3) 0.12217(14) 0.1985(7) 0.0599(9) Uani 1 1 d . . . C2 C 0.5686(3) 0.16964(14) 0.0207(8) 0.0600(10) Uani 1 1 d . . . C3 C 0.4908(3) 0.20350(18) 0.0044(10) 0.0785(12) Uani 1 1 d . . . H3 H 0.4875 0.2344 -0.1093 0.094 Uiso 1 1 calc R . . C4 C 0.4159(3) 0.1912(2) 0.1607(13) 0.0943(16) Uani 1 1 d . . . H4 H 0.3636 0.2143 0.1453 0.113 Uiso 1 1 calc R . . C5 C 0.4167(3) 0.1477(2) 0.3310(10) 0.0916(15) Uani 1 1 d . . . H5 H 0.3662 0.1411 0.4319 0.110 Uiso 1 1 calc R . . C6 C 0.4953(3) 0.11223(19) 0.3536(9) 0.0738(11) Uani 1 1 d . . . C7 C 0.5034(4) 0.0671(2) 0.5308(11) 0.0910(14) Uani 1 1 d . . . H7 H 0.4562 0.0595 0.6413 0.109 Uiso 1 1 calc R . . C8 C 0.5820(4) 0.0346(2) 0.5381(11) 0.1017(17) Uani 1 1 d . . . H8 H 0.5886 0.0044 0.6538 0.122 Uiso 1 1 calc R . . C9 C 0.6524(3) 0.04680(19) 0.3715(9) 0.0793(12) Uani 1 1 d . . . H9 H 0.7051 0.0239 0.3788 0.095 Uiso 1 1 calc R . . C10 C 0.6456(3) 0.21153(15) -0.3466(8) 0.0657(10) Uani 1 1 d . . . H10A H 0.5852 0.2077 -0.4184 0.079 Uiso 1 1 calc R . . H10B H 0.6880 0.1919 -0.4575 0.079 Uiso 1 1 calc R . . C11 C 0.6694(2) 0.27615(16) -0.3398(8) 0.0601(9) Uani 1 1 d . . . C12 C 0.6934(2) 0.36425(14) -0.0850(8) 0.0589(9) Uani 1 1 d . . . H12A H 0.7108 0.3823 -0.2411 0.071 Uiso 1 1 calc R . . H12B H 0.7426 0.3708 0.0322 0.071 Uiso 1 1 calc R . . C13 C 0.6084(2) 0.39341(15) 0.0091(9) 0.0655(10) Uani 1 1 d . . . H13A H 0.5902 0.3743 0.1622 0.079 Uiso 1 1 calc R . . H13B H 0.5599 0.3875 -0.1105 0.079 Uiso 1 1 calc R . . C14 C 0.6191(2) 0.45888(15) 0.0556(7) 0.0524(8) Uani 1 1 d . . . C15 C 0.6648(3) 0.47979(17) 0.2631(7) 0.0621(10) Uani 1 1 d . . . H15 H 0.6895 0.4532 0.3762 0.075 Uiso 1 1 calc R . . C16 C 0.6737(3) 0.54010(18) 0.3023(7) 0.0675(11) Uani 1 1 d . . . H16 H 0.7041 0.5537 0.4423 0.081 Uiso 1 1 calc R . . C17 C 0.6382(3) 0.57979(16) 0.1370(7) 0.0597(10) Uani 1 1 d . . . C18 C 0.5939(2) 0.55978(15) -0.0721(8) 0.0594(9) Uani 1 1 d . . . H18 H 0.5701 0.5865 -0.1862 0.071 Uiso 1 1 calc R . . C19 C 0.5853(2) 0.49983(16) -0.1097(8) 0.0574(9) Uani 1 1 d . . . H19 H 0.5556 0.4865 -0.2515 0.069 Uiso 1 1 calc R . . C20 C 0.6148(4) 0.68101(19) 0.0196(14) 0.111(2) Uani 1 1 d . . . H20A H 0.6434 0.6749 -0.1384 0.166 Uiso 1 1 calc R . . H20B H 0.6273 0.7205 0.0764 0.166 Uiso 1 1 calc R . . H20C H 0.5501 0.6757 0.0037 0.166 Uiso 1 1 calc R . . H2 H 0.682(3) 0.1557(16) -0.079(8) 0.059(12) Uiso 1 1 d . . . H3N H 0.679(3) 0.2803(18) 0.009(10) 0.073(13) Uiso 1 1 d . . . N1 N 0.6479(2) 0.08871(13) 0.2065(7) 0.0659(8) Uani 1 1 d . . . N2 N 0.6462(2) 0.18024(14) -0.1144(7) 0.0629(9) Uani 1 1 d . . . N3 N 0.6813(2) 0.30085(14) -0.1212(7) 0.0590(8) Uani 1 1 d . . . O1 O 0.6757(3) 0.30300(14) -0.5375(6) 0.0927(10) Uani 1 1 d . . . O2 O 0.6504(2) 0.63885(12) 0.1956(7) 0.0860(9) 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 C1 0.078(2) 0.051(2) 0.051(2) -0.0111(19) -0.004(2) -0.0174(18) C2 0.068(2) 0.050(2) 0.062(3) -0.0141(19) -0.005(2) -0.0052(17) C3 0.080(3) 0.067(3) 0.088(3) -0.011(2) -0.017(2) 0.003(2) C4 0.066(3) 0.096(3) 0.120(5) -0.036(4) -0.008(3) -0.002(2) C5 0.082(3) 0.107(4) 0.085(4) -0.020(3) 0.010(3) -0.024(3) C6 0.081(3) 0.077(3) 0.063(3) -0.016(2) 0.000(2) -0.026(2) C7 0.105(4) 0.098(4) 0.070(3) -0.002(3) 0.005(3) -0.041(3) C8 0.137(5) 0.089(3) 0.079(3) 0.017(3) -0.017(4) -0.039(3) C9 0.103(3) 0.068(3) 0.067(3) 0.013(2) -0.015(3) -0.021(2) C10 0.093(3) 0.054(2) 0.050(2) -0.0029(18) -0.003(2) 0.0022(18) C11 0.079(2) 0.057(2) 0.045(2) 0.004(2) -0.009(2) 0.0024(17) C12 0.066(2) 0.0428(18) 0.068(3) 0.0006(18) 0.0005(19) -0.0038(15) C13 0.065(2) 0.052(2) 0.080(3) 0.004(2) -0.004(2) -0.0057(16) C14 0.0527(18) 0.054(2) 0.050(2) 0.0024(18) 0.0050(16) -0.0001(16) C15 0.082(3) 0.060(2) 0.044(2) 0.0088(17) -0.0061(18) -0.0031(19) C16 0.091(3) 0.071(3) 0.041(2) -0.0011(19) -0.0040(18) -0.012(2) C17 0.070(2) 0.049(2) 0.060(3) -0.0020(18) 0.0106(19) -0.0007(17) C18 0.069(2) 0.056(2) 0.054(2) 0.0062(18) -0.0018(19) 0.0085(16) C19 0.064(2) 0.058(2) 0.049(2) -0.0019(18) -0.0061(17) 0.0029(16) C20 0.126(4) 0.051(3) 0.154(6) 0.006(3) 0.003(4) 0.015(3) N1 0.087(2) 0.0515(17) 0.059(2) -0.0011(17) -0.0095(18) -0.0067(16) N2 0.076(2) 0.0469(18) 0.066(2) 0.0038(17) -0.0017(19) 0.0044(16) N3 0.083(2) 0.0459(18) 0.048(2) 0.0071(17) -0.0029(17) -0.0044(14) O1 0.148(3) 0.0743(19) 0.055(2) 0.0129(17) -0.0051(17) -0.0089(18) O2 0.107(2) 0.0549(16) 0.096(2) -0.0110(17) 0.007(2) -0.0084(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.364(5) . ? C1 C6 1.401(5) . ? C1 C2 1.439(5) . ? C2 N2 1.372(5) . ? C2 C3 1.376(5) . ? C3 C4 1.412(7) . ? C3 H3 0.9300 . ? C4 C5 1.346(7) . ? C4 H4 0.9300 . ? C5 C6 1.408(7) . ? C5 H5 0.9300 . ? C6 C7 1.402(7) . ? C7 C8 1.366(7) . ? C7 H7 0.9300 . ? C8 C9 1.396(7) . ? C8 H8 0.9300 . ? C9 N1 1.301(5) . ? C9 H9 0.9300 . ? C10 N2 1.439(5) . ? C10 C11 1.501(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O1 1.231(5) . ? C11 N3 1.317(5) . ? C12 N3 1.456(4) . ? C12 C13 1.498(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.508(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C19 1.377(5) . ? C14 C15 1.388(5) . ? C15 C16 1.384(5) . ? C15 H15 0.9300 . ? C16 C17 1.367(5) . ? C16 H16 0.9300 . ? C17 C18 1.379(5) . ? C17 O2 1.382(4) . ? C18 C19 1.374(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 O2 1.442(7) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? N2 H2 0.79(4) . ? N3 H3N 0.84(5) . ? 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 N1 C1 C6 123.1(4) . . ? N1 C1 C2 116.7(3) . . ? C6 C1 C2 120.2(4) . . ? N2 C2 C3 123.8(4) . . ? N2 C2 C1 118.0(3) . . ? C3 C2 C1 118.2(4) . . ? C2 C3 C4 119.8(5) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 123.0(5) . . ? C5 C4 H4 118.5 . . ? C3 C4 H4 118.5 . . ? C4 C5 C6 118.8(5) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C1 C6 C7 117.2(4) . . ? C1 C6 C5 120.0(4) . . ? C7 C6 C5 122.8(5) . . ? C8 C7 C6 118.8(5) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C7 C8 C9 119.9(5) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? N1 C9 C8 123.1(5) . . ? N1 C9 H9 118.4 . . ? C8 C9 H9 118.4 . . ? N2 C10 C11 117.0(3) . . ? N2 C10 H10A 108.0 . . ? C11 C10 H10A 108.0 . . ? N2 C10 H10B 108.0 . . ? C11 C10 H10B 108.0 . . ? H10A C10 H10B 107.3 . . ? O1 C11 N3 124.0(3) . . ? O1 C11 C10 118.4(4) . . ? N3 C11 C10 117.7(4) . . ? N3 C12 C13 112.1(3) . . ? N3 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? N3 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C12 C13 C14 113.6(3) . . ? C12 C13 H13A 108.8 . . ? C14 C13 H13A 108.8 . . ? C12 C13 H13B 108.8 . . ? C14 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C19 C14 C15 117.9(3) . . ? C19 C14 C13 120.8(3) . . ? C15 C14 C13 121.2(3) . . ? C16 C15 C14 120.2(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C15 120.6(4) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 119.9(3) . . ? C16 C17 O2 115.7(4) . . ? C18 C17 O2 124.4(4) . . ? C19 C18 C17 119.1(3) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C14 122.1(4) . . ? C18 C19 H19 118.9 . . ? C14 C19 H19 118.9 . . ? O2 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C9 N1 C1 117.8(4) . . ? C2 N2 C10 122.9(4) . . ? C2 N2 H2 108(3) . . ? C10 N2 H2 124(3) . . ? C11 N3 C12 123.5(4) . . ? C11 N3 H3N 121(3) . . ? C12 N3 H3N 116(3) . . ? C17 O2 C20 116.1(4) . . ? 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 N1 C1 C2 N2 -4.3(5) . . . . ? C6 C1 C2 N2 175.4(3) . . . . ? N1 C1 C2 C3 178.7(3) . . . . ? C6 C1 C2 C3 -1.6(5) . . . . ? N2 C2 C3 C4 -176.5(4) . . . . ? C1 C2 C3 C4 0.3(6) . . . . ? C2 C3 C4 C5 0.9(7) . . . . ? C3 C4 C5 C6 -0.6(7) . . . . ? N1 C1 C6 C7 2.8(6) . . . . ? C2 C1 C6 C7 -176.9(4) . . . . ? N1 C1 C6 C5 -178.5(4) . . . . ? C2 C1 C6 C5 1.8(5) . . . . ? C4 C5 C6 C1 -0.7(6) . . . . ? C4 C5 C6 C7 178.0(4) . . . . ? C1 C6 C7 C8 -1.8(6) . . . . ? C5 C6 C7 C8 179.5(5) . . . . ? C6 C7 C8 C9 0.2(7) . . . . ? C7 C8 C9 N1 0.6(7) . . . . ? N2 C10 C11 O1 175.0(4) . . . . ? N2 C10 C11 N3 -5.9(5) . . . . ? N3 C12 C13 C14 178.4(3) . . . . ? C12 C13 C14 C19 102.4(4) . . . . ? C12 C13 C14 C15 -76.3(5) . . . . ? C19 C14 C15 C16 1.3(5) . . . . ? C13 C14 C15 C16 -179.9(3) . . . . ? C14 C15 C16 C17 -0.4(6) . . . . ? C15 C16 C17 C18 -0.6(6) . . . . ? C15 C16 C17 O2 179.5(3) . . . . ? C16 C17 C18 C19 0.6(5) . . . . ? O2 C17 C18 C19 -179.5(3) . . . . ? C17 C18 C19 C14 0.4(5) . . . . ? C15 C14 C19 C18 -1.4(5) . . . . ? C13 C14 C19 C18 179.9(3) . . . . ? C8 C9 N1 C1 0.3(6) . . . . ? C6 C1 N1 C9 -2.0(5) . . . . ? C2 C1 N1 C9 177.7(3) . . . . ? C3 C2 N2 C10 -24.2(6) . . . . ? C1 C2 N2 C10 159.0(3) . . . . ? C11 C10 N2 C2 97.9(4) . . . . ? O1 C11 N3 C12 7.0(6) . . . . ? C10 C11 N3 C12 -172.1(3) . . . . ? C13 C12 N3 C11 102.9(4) . . . . ? C16 C17 O2 C20 178.8(4) . . . . ? C18 C17 O2 C20 -1.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.612 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.038 # Attachment 'III.cif' data_meoet8aqhclo4 _database_code_depnum_ccdc_archive 'CCDC 724795' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 Cl N3 O6' _chemical_formula_weight 435.86 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 Trigonal _symmetry_space_group_name_H-M 'R-3 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 33.2881(8) _cell_length_b 33.2881(8) _cell_length_c 9.8459(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 9448.5(4) _cell_formula_units_Z 18 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9890 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 23.54 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4104 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 36199 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 25.74 _reflns_number_total 4017 _reflns_number_gt 2972 _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^)+(0.1600P)^2^+3.8401P] 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 4017 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0873 _refine_ls_R_factor_gt 0.0650 _refine_ls_wR_factor_ref 0.2491 _refine_ls_wR_factor_gt 0.2177 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.162 _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 C1 C 0.83239(9) 0.11655(9) 0.7426(3) 0.0397(6) Uani 1 1 d . . . C2 C 0.79900(9) 0.07512(9) 0.6777(3) 0.0419(6) Uani 1 1 d . . . C3 C 0.81435(11) 0.05984(10) 0.5685(3) 0.0548(8) Uani 1 1 d . . . H3 H 0.7935 0.0326 0.5241 0.066 Uiso 1 1 calc R . . C4 C 0.85991(12) 0.08421(12) 0.5243(4) 0.0655(9) Uani 1 1 d . . . H4 H 0.8689 0.0728 0.4511 0.079 Uiso 1 1 calc R . . C5 C 0.89191(11) 0.12429(11) 0.5846(3) 0.0626(9) Uani 1 1 d . . . H5 H 0.9222 0.1402 0.5524 0.075 Uiso 1 1 calc R . . C6 C 0.87874(9) 0.14166(9) 0.6968(3) 0.0473(7) Uani 1 1 d . . . C7 C 0.90951(10) 0.18320(10) 0.7647(3) 0.0554(8) Uani 1 1 d . . . H7 H 0.9402 0.2001 0.7361 0.066 Uiso 1 1 calc R . . C8 C 0.89550(10) 0.19899(11) 0.8697(3) 0.0574(8) Uani 1 1 d . . . H8 H 0.9161 0.2266 0.9128 0.069 Uiso 1 1 calc R . . C9 C 0.84989(10) 0.17343(10) 0.9127(3) 0.0520(7) Uani 1 1 d . . . H9 H 0.8398 0.1838 0.9858 0.062 Uiso 1 1 calc R . . C10 C 0.71860(10) 0.01167(10) 0.6470(3) 0.0513(7) Uani 1 1 d . . . H10A H 0.7212 0.0192 0.5510 0.062 Uiso 1 1 calc R . . H10B H 0.6882 0.0053 0.6769 0.062 Uiso 1 1 calc R . . C11 C 0.72186(9) -0.03158(9) 0.6651(3) 0.0432(6) Uani 1 1 d . . . C12 C 0.74797(11) -0.07497(11) 0.8023(3) 0.0589(8) Uani 1 1 d . . . H12A H 0.7528 -0.0871 0.7180 0.071 Uiso 1 1 calc R . . H12B H 0.7198 -0.0991 0.8442 0.071 Uiso 1 1 calc R . . C13 C 0.78879(12) -0.06177(12) 0.8966(4) 0.0721(10) Uani 1 1 d . . . H13A H 0.7837 -0.0497 0.9805 0.087 Uiso 1 1 calc R . . H13B H 0.7902 -0.0894 0.9187 0.087 Uiso 1 1 calc R . . C14 C 0.83460(11) -0.02610(12) 0.8364(3) 0.0607(8) Uani 1 1 d . . . C15 C 0.86131(13) 0.01628(13) 0.8968(4) 0.0782(11) Uani 1 1 d . . . H15 H 0.8505 0.0229 0.9759 0.094 Uiso 1 1 calc R . . C16 C 0.90326(15) 0.04924(15) 0.8455(5) 0.0894(13) Uani 1 1 d . . . H16 H 0.9207 0.0772 0.8914 0.107 Uiso 1 1 calc R . . C17 C 0.91926(14) 0.04137(15) 0.7291(5) 0.0842(12) Uani 1 1 d . . . C18 C 0.89345(16) 0.00059(17) 0.6625(5) 0.1014(15) Uani 1 1 d . . . H18 H 0.9039 -0.0049 0.5808 0.122 Uiso 1 1 calc R . . C19 C 0.85204(14) -0.03239(14) 0.7160(5) 0.0883(13) Uani 1 1 d . . . H19 H 0.8349 -0.0602 0.6694 0.106 Uiso 1 1 calc R . . C20 C 0.9906(2) 0.1134(2) 0.7386(8) 0.163(3) Uani 1 1 d . . . H20A H 0.9786 0.1343 0.7367 0.245 Uiso 1 1 calc R . . H20B H 1.0206 0.1279 0.6964 0.245 Uiso 1 1 calc R . . H20C H 0.9933 0.1059 0.8311 0.245 Uiso 1 1 calc R . . Cl1 Cl 0.62125(3) 0.06479(3) 0.49853(8) 0.0592(3) Uani 1 1 d . . . H1 H 0.7951(11) 0.1199(10) 0.881(3) 0.049(9) Uiso 1 1 d . . . H2 H 0.7393(12) 0.0606(12) 0.777(4) 0.063(9) Uiso 1 1 d . . . H3N H 0.7507(14) -0.0160(13) 0.829(4) 0.078(13) Uiso 1 1 d . . . N1 N 0.82059(8) 0.13448(8) 0.8505(2) 0.0436(6) Uani 1 1 d . . . N2 N 0.75361(8) 0.05174(8) 0.7202(3) 0.0472(6) Uani 1 1 d . . . N3 N 0.74268(9) -0.03493(9) 0.7735(3) 0.0508(6) Uani 1 1 d . . . O1 O 0.70535(7) -0.06224(6) 0.5761(2) 0.0527(6) Uani 1 1 d . . . O2 O 0.96059(12) 0.07289(13) 0.6683(4) 0.1284(13) Uani 1 1 d . . . O3 O 0.63196(15) 0.03933(17) 0.5899(5) 0.1501(16) Uani 1 1 d . . . O4 O 0.63902(12) 0.10925(10) 0.5514(4) 0.1150(12) Uani 1 1 d . . . O5 O 0.57308(10) 0.04164(12) 0.4881(4) 0.1103(11) Uani 1 1 d . . . O6 O 0.64176(15) 0.06709(14) 0.3741(4) 0.1431(16) 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 C1 0.0421(14) 0.0427(13) 0.0366(14) 0.0038(11) 0.0017(10) 0.0231(11) C2 0.0480(15) 0.0401(13) 0.0396(15) -0.0002(11) 0.0033(11) 0.0236(12) C3 0.0643(18) 0.0481(16) 0.0518(18) -0.0045(13) 0.0114(14) 0.0279(14) C4 0.073(2) 0.064(2) 0.065(2) -0.0003(16) 0.0237(17) 0.0387(18) C5 0.0512(17) 0.0644(19) 0.073(2) 0.0123(16) 0.0242(16) 0.0294(15) C6 0.0437(14) 0.0495(15) 0.0500(17) 0.0087(12) 0.0046(12) 0.0243(12) C7 0.0405(14) 0.0503(16) 0.067(2) 0.0084(14) -0.0006(13) 0.0163(13) C8 0.0498(16) 0.0481(16) 0.064(2) -0.0057(14) -0.0147(14) 0.0167(13) C9 0.0546(17) 0.0506(16) 0.0459(17) -0.0073(13) -0.0035(13) 0.0226(14) C10 0.0462(15) 0.0462(15) 0.0598(19) -0.0105(13) -0.0107(13) 0.0218(13) C11 0.0338(12) 0.0415(14) 0.0459(16) -0.0051(11) -0.0006(11) 0.0125(11) C12 0.0580(17) 0.0515(17) 0.063(2) 0.0055(14) -0.0053(14) 0.0243(14) C13 0.066(2) 0.070(2) 0.074(2) 0.0118(18) -0.0137(17) 0.0289(18) C14 0.0599(19) 0.0666(19) 0.061(2) -0.0030(16) -0.0106(15) 0.0362(16) C15 0.075(2) 0.074(2) 0.071(3) -0.0149(19) 0.0026(19) 0.0261(19) C16 0.081(3) 0.076(3) 0.086(3) -0.023(2) 0.006(2) 0.021(2) C17 0.065(2) 0.085(3) 0.086(3) -0.011(2) 0.008(2) 0.025(2) C18 0.087(3) 0.119(4) 0.088(3) -0.038(3) 0.006(2) 0.043(3) C19 0.072(2) 0.076(3) 0.104(3) -0.036(2) -0.011(2) 0.028(2) C20 0.102(4) 0.116(5) 0.191(7) -0.017(4) 0.024(4) -0.006(3) Cl1 0.0530(5) 0.0579(5) 0.0528(6) -0.0015(3) 0.0062(3) 0.0173(4) N1 0.0417(13) 0.0431(12) 0.0412(13) -0.0038(10) 0.0008(10) 0.0177(11) N2 0.0446(13) 0.0440(12) 0.0500(15) -0.0104(10) 0.0023(10) 0.0199(10) N3 0.0529(14) 0.0487(14) 0.0464(15) -0.0074(12) -0.0072(11) 0.0221(11) O1 0.0553(12) 0.0444(11) 0.0525(12) -0.0122(9) -0.0142(9) 0.0205(9) O2 0.087(2) 0.127(3) 0.125(3) -0.012(2) 0.036(2) 0.019(2) O3 0.165(4) 0.193(4) 0.136(4) 0.041(3) -0.003(3) 0.122(4) O4 0.110(2) 0.0761(19) 0.121(3) -0.0280(17) 0.014(2) 0.0184(17) O5 0.0630(17) 0.122(3) 0.111(3) -0.0040(19) -0.0009(15) 0.0196(16) O6 0.149(3) 0.137(3) 0.093(2) 0.000(2) 0.073(2) 0.034(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 C1 N1 1.369(3) . ? C1 C6 1.412(4) . ? C1 C2 1.419(4) . ? C2 N2 1.374(3) . ? C2 C3 1.391(4) . ? C3 C4 1.385(4) . ? C3 H3 0.9300 . ? C4 C5 1.359(5) . ? C4 H4 0.9300 . ? C5 C6 1.414(4) . ? C5 H5 0.9300 . ? C6 C7 1.411(4) . ? C7 C8 1.345(4) . ? C7 H7 0.9300 . ? C8 C9 1.384(4) . ? C8 H8 0.9300 . ? C9 N1 1.320(3) . ? C9 H9 0.9300 . ? C10 N2 1.450(3) . ? C10 C11 1.507(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O1 1.245(3) . ? C11 N3 1.308(4) . ? C12 N3 1.457(4) . ? C12 C13 1.518(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.509(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.371(5) . ? C14 C19 1.381(5) . ? C15 C16 1.370(5) . ? C15 H15 0.9300 . ? C16 C17 1.343(6) . ? C16 H16 0.9300 . ? C17 C18 1.358(6) . ? C17 O2 1.382(5) . ? C18 C19 1.367(6) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 O2 1.396(7) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? Cl1 O6 1.386(3) . ? Cl1 O4 1.391(3) . ? Cl1 O5 1.393(3) . ? Cl1 O3 1.399(4) . ? N1 H1 0.80(3) . ? N2 H2 0.87(4) . ? N3 H3N 0.77(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 N1 C1 C6 117.2(2) . . ? N1 C1 C2 121.2(2) . . ? C6 C1 C2 121.6(2) . . ? N2 C2 C3 122.0(3) . . ? N2 C2 C1 121.2(2) . . ? C3 C2 C1 116.8(2) . . ? C4 C3 C2 121.6(3) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C5 C4 C3 122.0(3) . . ? C5 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C4 C5 C6 119.5(3) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C7 C6 C1 118.1(3) . . ? C7 C6 C5 123.3(3) . . ? C1 C6 C5 118.5(3) . . ? C8 C7 C6 121.6(3) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C7 C8 C9 118.9(3) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? N1 C9 C8 120.5(3) . . ? N1 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? N2 C10 C11 114.3(2) . . ? N2 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? N2 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? O1 C11 N3 122.7(3) . . ? O1 C11 C10 119.1(2) . . ? N3 C11 C10 118.2(2) . . ? N3 C12 C13 110.8(3) . . ? N3 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C14 C13 C12 113.2(3) . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.8 . . ? C15 C14 C19 115.0(3) . . ? C15 C14 C13 121.3(3) . . ? C19 C14 C13 123.6(3) . . ? C16 C15 C14 122.8(4) . . ? C16 C15 H15 118.6 . . ? C14 C15 H15 118.6 . . ? C17 C16 C15 120.2(4) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.5(4) . . ? C16 C17 O2 124.2(4) . . ? C18 C17 O2 116.2(4) . . ? C17 C18 C19 119.7(4) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C18 C19 C14 122.7(4) . . ? C18 C19 H19 118.6 . . ? C14 C19 H19 118.6 . . ? O2 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O6 Cl1 O4 109.7(2) . . ? O6 Cl1 O5 111.4(2) . . ? O4 Cl1 O5 112.1(2) . . ? O6 Cl1 O3 109.5(3) . . ? O4 Cl1 O3 107.6(3) . . ? O5 Cl1 O3 106.5(2) . . ? C9 N1 C1 123.8(3) . . ? C9 N1 H1 117(2) . . ? C1 N1 H1 119(2) . . ? C2 N2 C10 121.3(2) . . ? C2 N2 H2 129(2) . . ? C10 N2 H2 108(2) . . ? C11 N3 C12 123.3(3) . . ? C11 N3 H3N 119(3) . . ? C12 N3 H3N 117(3) . . ? C17 O2 C20 118.6(4) . . ? 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 N1 C1 C2 N2 0.5(4) . . . . ? C6 C1 C2 N2 -177.8(2) . . . . ? N1 C1 C2 C3 179.7(3) . . . . ? C6 C1 C2 C3 1.3(4) . . . . ? N2 C2 C3 C4 178.4(3) . . . . ? C1 C2 C3 C4 -0.7(4) . . . . ? C2 C3 C4 C5 -0.2(5) . . . . ? C3 C4 C5 C6 0.6(5) . . . . ? N1 C1 C6 C7 0.0(4) . . . . ? C2 C1 C6 C7 178.4(2) . . . . ? N1 C1 C6 C5 -179.4(3) . . . . ? C2 C1 C6 C5 -1.0(4) . . . . ? C4 C5 C6 C7 -179.3(3) . . . . ? C4 C5 C6 C1 0.0(5) . . . . ? C1 C6 C7 C8 -0.4(4) . . . . ? C5 C6 C7 C8 178.9(3) . . . . ? C6 C7 C8 C9 0.7(5) . . . . ? C7 C8 C9 N1 -0.7(5) . . . . ? N2 C10 C11 O1 -155.8(3) . . . . ? N2 C10 C11 N3 23.2(4) . . . . ? N3 C12 C13 C14 -62.3(4) . . . . ? C12 C13 C14 C15 119.3(4) . . . . ? C12 C13 C14 C19 -58.2(5) . . . . ? C19 C14 C15 C16 -3.0(6) . . . . ? C13 C14 C15 C16 179.3(4) . . . . ? C14 C15 C16 C17 2.1(7) . . . . ? C15 C16 C17 C18 0.3(8) . . . . ? C15 C16 C17 O2 178.5(5) . . . . ? C16 C17 C18 C19 -1.5(8) . . . . ? O2 C17 C18 C19 -179.9(5) . . . . ? C17 C18 C19 C14 0.5(8) . . . . ? C15 C14 C19 C18 1.7(6) . . . . ? C13 C14 C19 C18 179.3(4) . . . . ? C8 C9 N1 C1 0.3(4) . . . . ? C6 C1 N1 C9 0.1(4) . . . . ? C2 C1 N1 C9 -178.3(3) . . . . ? C3 C2 N2 C10 -4.5(4) . . . . ? C1 C2 N2 C10 174.6(2) . . . . ? C11 C10 N2 C2 73.5(4) . . . . ? O1 C11 N3 C12 -1.1(4) . . . . ? C10 C11 N3 C12 180.0(3) . . . . ? C13 C12 N3 C11 156.3(3) . . . . ? C16 C17 O2 C20 7.9(8) . . . . ? C18 C17 O2 C20 -173.8(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.74 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.016 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.119