Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name J.-M.Lehn V.Berl H.Risler W.G.Skene _publ_contact_author_name 'Jean-Marie Lehn' _publ_contact_author_email LEHN@ISIS.U-STRASBG.FR data_dibenzo _database_code_depnum_ccdc_archive 'CCDC 604878' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'furan recepter' _chemical_melting_point ? _chemical_formula_moiety 'C24 H18 N6 O' _chemical_formula_sum 'C24 H18 N6 O' _chemical_formula_weight 406.154 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 Pbcn _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 13.111(3) _cell_length_b 10.123(2) _cell_length_c 14.928(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1981.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4374 _cell_measurement_theta_min 2.01 _cell_measurement_theta_max 27.46 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.088 _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 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4066 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2265 _reflns_number_gt 1844 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Data collection software (Nonius B.V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP-97, Semiens' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0865P)^2^+1.4023P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef 0.009(2) _refine_ls_number_reflns 2265 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0844 _refine_ls_R_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.1946 _refine_ls_wR_factor_gt 0.1854 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _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 0.5000 0.4238(2) -0.2500 0.0327(5) Uani 1 2 d S . . N1 N 0.62120(15) 0.2711(2) -0.01340(13) 0.0395(5) Uani 1 1 d . . . N2 N 0.60140(17) 0.1400(2) 0.00210(13) 0.0417(5) Uani 1 1 d . . . H2B H 0.5699 0.0921 -0.0385 0.050 Uiso 1 1 d R . . N3 N 0.59128(16) -0.0331(2) 0.10314(13) 0.0423(5) Uani 1 1 d . . . C1 C 0.53962(16) 0.5075(2) -0.18444(14) 0.0327(5) Uani 1 1 d . . . C2 C 0.52776(18) 0.6407(2) -0.20715(15) 0.0364(6) Uani 1 1 d . . . C3 C 0.56919(19) 0.7356(2) -0.14998(17) 0.0422(6) Uani 1 1 d . . . H3B H 0.5631 0.8271 -0.1632 0.051 Uiso 1 1 calc R . . C4 C 0.61955(19) 0.6935(3) -0.07337(17) 0.0446(6) Uani 1 1 d . . . H4B H 0.6503 0.7574 -0.0353 0.053 Uiso 1 1 calc R . . C5 C 0.62639(18) 0.5600(3) -0.05050(16) 0.0414(6) Uani 1 1 d . . . H5B H 0.6596 0.5354 0.0036 0.050 Uiso 1 1 calc R . . C6 C 0.58509(17) 0.4610(2) -0.10588(14) 0.0341(5) Uani 1 1 d . . . C7 C 0.58077(17) 0.3205(2) -0.08393(14) 0.0362(5) Uani 1 1 d . . . H7A H 0.5462 0.2629 -0.1240 0.043 Uiso 1 1 calc R . . C8 C 0.63173(18) 0.0839(2) 0.08293(15) 0.0366(5) Uani 1 1 d . . . C9 C 0.70135(19) 0.1492(3) 0.13828(16) 0.0412(6) Uani 1 1 d . . . H9A H 0.7275 0.2336 0.1226 0.049 Uiso 1 1 calc R . . C10 C 0.73072(19) 0.0879(2) 0.21575(16) 0.0418(6) Uani 1 1 d . . . H10A H 0.7784 0.1300 0.2542 0.050 Uiso 1 1 calc R . . C11 C 0.6919(2) -0.0345(2) 0.23886(17) 0.0428(6) Uani 1 1 d . . . H11A H 0.7122 -0.0781 0.2923 0.051 Uiso 1 1 calc R . . C12 C 0.6220(2) -0.0908(3) 0.18050(18) 0.0448(6) Uani 1 1 d . . . H12A H 0.5942 -0.1745 0.1956 0.054 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 0.0361(12) 0.0327(11) 0.0293(11) 0.000 -0.0019(9) 0.000 N1 0.0371(11) 0.0438(11) 0.0376(11) -0.0015(8) -0.0007(8) -0.0015(9) N2 0.0455(12) 0.0421(11) 0.0375(11) -0.0010(8) -0.0086(9) -0.0041(9) N3 0.0420(11) 0.0412(12) 0.0439(12) -0.0073(9) -0.0141(9) 0.0051(9) C1 0.0291(11) 0.0359(11) 0.0331(11) -0.0046(9) 0.0057(9) -0.0048(9) C2 0.0330(12) 0.0363(12) 0.0400(12) -0.0019(9) 0.0124(9) -0.0009(9) C3 0.0411(13) 0.0357(12) 0.0497(14) -0.0065(10) 0.0146(11) -0.0072(11) C4 0.0401(13) 0.0484(15) 0.0451(14) -0.0155(11) 0.0093(11) -0.0110(11) C5 0.0348(12) 0.0531(15) 0.0361(12) -0.0099(10) 0.0038(10) -0.0075(11) C6 0.0300(11) 0.0424(13) 0.0298(11) -0.0034(9) 0.0036(8) -0.0038(10) C7 0.0347(12) 0.0459(13) 0.0281(10) 0.0006(9) -0.0023(9) -0.0051(10) C8 0.0379(12) 0.0401(13) 0.0320(11) -0.0024(9) -0.0012(9) 0.0103(10) C9 0.0389(13) 0.0443(14) 0.0405(13) -0.0017(10) -0.0036(10) 0.0020(11) C10 0.0387(13) 0.0459(14) 0.0406(12) -0.0063(10) -0.0099(10) 0.0045(11) C11 0.0442(14) 0.0442(13) 0.0399(13) 0.0023(10) -0.0117(11) 0.0070(11) C12 0.0443(14) 0.0362(13) 0.0540(15) 0.0002(11) -0.0087(12) 0.0030(11) _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 C1 1.395(3) . ? O1 C1 1.395(3) 4_654 ? N1 C7 1.281(3) . ? N1 N2 1.371(3) . ? N2 C8 1.392(3) . ? N2 H2B 0.8796 . ? N3 C8 1.332(3) . ? N3 C12 1.355(3) . ? C1 C6 1.397(3) . ? C1 C2 1.399(3) . ? C2 C3 1.395(3) . ? C2 C2 1.472(5) 4_654 ? C3 C4 1.388(4) . ? C3 H3B 0.9500 . ? C4 C5 1.398(4) . ? C4 H4B 0.9500 . ? C5 C6 1.407(3) . ? C5 H5B 0.9500 . ? C6 C7 1.460(3) . ? C7 H7A 0.9500 . ? C8 C9 1.397(3) . ? C9 C10 1.368(3) . ? C9 H9A 0.9500 . ? C10 C11 1.384(4) . ? C10 H10A 0.9500 . ? C11 C12 1.386(3) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C1 105.1(2) . 4_654 ? C7 N1 N2 116.0(2) . . ? N1 N2 C8 119.2(2) . . ? N1 N2 H2B 120.4 . . ? C8 N2 H2B 120.4 . . ? C8 N3 C12 117.2(2) . . ? O1 C1 C6 122.9(2) . . ? O1 C1 C2 112.0(2) . . ? C6 C1 C2 125.1(2) . . ? C3 C2 C1 118.2(2) . . ? C3 C2 C2 136.41(15) . 4_654 ? C1 C2 C2 105.40(13) . 4_654 ? C4 C3 C2 118.6(2) . . ? C4 C3 H3B 120.7 . . ? C2 C3 H3B 120.7 . . ? C3 C4 C5 121.9(2) . . ? C3 C4 H4B 119.0 . . ? C5 C4 H4B 119.0 . . ? C4 C5 C6 121.4(2) . . ? C4 C5 H5B 119.3 . . ? C6 C5 H5B 119.3 . . ? C1 C6 C5 114.7(2) . . ? C1 C6 C7 120.0(2) . . ? C5 C6 C7 125.2(2) . . ? N1 C7 C6 123.3(2) . . ? N1 C7 H7A 118.3 . . ? C6 C7 H7A 118.3 . . ? N3 C8 N2 116.5(2) . . ? N3 C8 C9 123.1(2) . . ? N2 C8 C9 120.4(2) . . ? C10 C9 C8 118.0(2) . . ? C10 C9 H9A 121.0 . . ? C8 C9 H9A 121.0 . . ? C9 C10 C11 120.9(2) . . ? C9 C10 H10A 119.5 . . ? C11 C10 H10A 119.5 . . ? C10 C11 C12 117.0(2) . . ? C10 C11 H11A 121.5 . . ? C12 C11 H11A 121.5 . . ? N3 C12 C11 123.7(2) . . ? N3 C12 H12A 118.1 . . ? C11 C12 H12A 118.1 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.634 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.055 # Attachment 'Template_2.CIF' data_recp1 _database_code_depnum_ccdc_archive 'CCDC 604879' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C35 H40 N6 O, C H Cl3' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C36 H41 Cl3 N6 O' _chemical_formula_weight 680.10 _chemical_melting_point ? _chemical_compound_source ? 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.280(3) _cell_length_b 22.540(5) _cell_length_c 10.510(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00(3) _cell_angle_gamma 90.00 _cell_volume 3619.8(13) _cell_formula_units_Z 4 _cell_measurement_temperature 193 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.4 _cell_measurement_theta_max 14.8 _exptl_crystal_description fragment _exptl_crystal_colour white _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method ? _exptl_crystal_F_000 1432 _exptl_absorpt_coefficient_mu 0.290 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 193 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device KappaCCD _diffrn_measurement_method '\p scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14283 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0803 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 27.73 _reflns_number_total 8274 _reflns_number_observed 5373 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4 Program (Nonius 1989)' _computing_cell_refinement LSFM_OpenMoleN_(_1997) _computing_data_reduction 'Local Program' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 'w=1/[\s^2^(Fo^2^)+(0.0909P)^2^+1.8500P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8274 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1183 _refine_ls_R_factor_obs 0.0688 _refine_ls_wR_factor_all 0.1935 _refine_ls_wR_factor_obs 0.1652 _refine_ls_goodness_of_fit_all 1.040 _refine_ls_goodness_of_fit_obs 1.110 _refine_ls_restrained_S_all 1.040 _refine_ls_restrained_S_obs 1.110 _refine_ls_shift/esd_max -0.011 _refine_ls_shift/esd_mean 0.002 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.11082(13) 0.97677(10) 0.8747(2) 0.0284(5) Uani 1 d . . N2 N 0.19617(13) 1.01860(10) 0.7165(2) 0.0309(5) Uani 1 d . . H2A H 0.14906 1.02464 0.6736 0.037 Uiso 1 calc R . N3 N 0.27552(13) 1.03605(10) 0.6673(2) 0.0272(5) Uani 1 d . . N4 N 0.12272(12) 1.03458(9) 0.2760(2) 0.0239(4) Uani 1 d . . N5 N 0.04565(12) 1.00559(9) 0.3021(2) 0.0265(5) Uani 1 d . . H5A H -0.00219 1.01699 0.2666 0.032 Uiso 1 calc R . N6 N -0.03348(13) 0.93134(9) 0.3992(2) 0.0256(5) Uani 1 d . . O1 O 0.29296(10) 1.07410(7) 0.29555(15) 0.0237(4) Uani 1 d . . C1 C 0.1035(2) 0.94984(12) 0.9886(2) 0.0323(6) Uani 1 d . . H1B H 0.0478 0.93976 1.0169 0.039 Uiso 1 calc R . C2 C 0.1729(2) 0.93648(13) 1.0648(2) 0.0356(6) Uani 1 d . . H2B H 0.1653 0.91757 1.1426 0.043 Uiso 1 calc R . C3 C 0.2562(2) 0.95248(13) 1.0207(3) 0.0396(7) Uani 1 d . . H3B H 0.3051 0.94425 1.0703 0.048 Uiso 1 calc R . C4 C 0.2664(2) 0.98018(13) 0.9052(3) 0.0362(7) Uani 1 d . . H4B H 0.3216 0.99097 0.8758 0.043 Uiso 1 calc R . C5 C 0.1916(2) 0.99156(11) 0.8337(2) 0.0260(5) Uani 1 d . . C6 C 0.2761(2) 1.05868(11) 0.5552(2) 0.0255(5) Uani 1 d . . H6B H 0.2242 1.06079 0.5092 0.031 Uiso 1 calc R . C7 C 0.35754(15) 1.08136(11) 0.4983(2) 0.0225(5) Uani 1 d . . C8 C 0.43006(15) 1.09494(11) 0.5727(2) 0.0250(5) Uani 1 d . . H8A H 0.42760 1.08818 0.6600 0.030 Uiso 1 calc R . C9 C 0.50697(15) 1.11858(11) 0.5198(2) 0.0242(5) Uani 1 d . . C10 C 0.5097(2) 1.12835(11) 0.3879(2) 0.0266(5) Uani 1 d . . H10A H 0.5599 1.14469 0.3522 0.032 Uiso 1 calc R . C11 C 0.43972(15) 1.11434(11) 0.3095(2) 0.0232(5) Uani 1 d . . C12 C 0.36447(14) 1.09088(10) 0.3666(2) 0.0210(5) Uani 1 d . . C13 C 0.44368(15) 1.11917(12) 0.1637(2) 0.0261(5) Uani 1 d . . C14 C 0.35047(15) 1.13082(11) 0.1172(2) 0.0214(5) Uani 1 d . . C15 C 0.3328(2) 1.16408(11) 0.0080(2) 0.0231(5) Uani 1 d . . H15A H 0.3788 1.18222 -0.0348 0.028 Uiso 1 calc R . C16 C 0.2478(2) 1.17079(10) -0.0383(2) 0.0228(5) Uani 1 d . . C17 C 0.1812(2) 1.14096(11) 0.0265(2) 0.0241(5) Uani 1 d . . H17A H 0.1245 1.14387 -0.0051 0.029 Uiso 1 calc R . C18 C 0.19466(15) 1.10686(10) 0.1365(2) 0.0208(5) Uani 1 d . . C19 C 0.28034(15) 1.10425(10) 0.1825(2) 0.0197(5) Uani 1 d . . C20 C 0.1189(2) 1.07487(11) 0.1897(2) 0.0239(5) Uani 1 d . . H20A H 0.0639 1.08462 0.1582 0.029 Uiso 1 calc R . C21 C 0.0450(2) 0.95830(11) 0.3851(2) 0.0240(5) Uani 1 d . . C22 C 0.1192(2) 0.94054(12) 0.4514(2) 0.0295(6) Uani 1 d . . H22A H 0.1726 0.95964 0.4400 0.035 Uiso 1 calc R . C23 C 0.1110(2) 0.89358(13) 0.5350(3) 0.0358(6) Uani 1 d . . H23A H 0.1592 0.88118 0.5819 0.043 Uiso 1 calc R . C24 C 0.0315(2) 0.86475(12) 0.5497(3) 0.0346(6) Uani 1 d . . H24A H 0.0255 0.83267 0.6046 0.041 Uiso 1 calc R . C25 C -0.0380(2) 0.88544(12) 0.4799(2) 0.0310(6) Uani 1 d . . H25A H -0.0916 0.86640 0.4892 0.037 Uiso 1 calc R . C26 C 0.2284(2) 1.21142(11) -0.1517(2) 0.0277(6) Uani 1 d . . C27 C 0.3083(2) 1.2201(2) -0.2384(3) 0.0590(10) Uani 1 d . . H27A H 0.3276 1.1822 -0.2695 0.088 Uiso 1 calc R . H27B H 0.3547 1.2384 -0.1910 0.088 Uiso 1 calc R . H27C H 0.2926 1.2450 -0.3089 0.088 Uiso 1 calc R . C28 C 0.1566(2) 1.1844(2) -0.2347(3) 0.0619(10) Uani 1 d . . H28A H 0.1759 1.1467 -0.2669 0.093 Uiso 1 calc R . H28B H 0.1442 1.2105 -0.3046 0.093 Uiso 1 calc R . H28C H 0.1046 1.1789 -0.1848 0.093 Uiso 1 calc R . C29 C 0.1970(3) 1.27121(14) -0.1017(3) 0.0649(11) Uani 1 d . . H29A H 0.2418 1.28856 -0.0495 0.097 Uiso 1 calc R . H29B H 0.1449 1.26566 -0.0521 0.097 Uiso 1 calc R . H29C H 0.1846 1.29706 -0.1720 0.097 Uiso 1 calc R . C30 C 0.4729(2) 1.05825(14) 0.1096(3) 0.0407(7) Uani 1 d . . H30A H 0.5314 1.04975 0.1374 0.061 Uiso 1 calc R . H30B H 0.4713 1.05947 0.0184 0.061 Uiso 1 calc R . H30C H 0.4341 1.02784 0.1397 0.061 Uiso 1 calc R . C31 C 0.5083(2) 1.1671(2) 0.1186(3) 0.0430(8) Uani 1 d . . H31A H 0.5658 1.1581 0.1497 0.064 Uiso 1 calc R . H31B H 0.4902 1.2051 0.1507 0.064 Uiso 1 calc R . H31C H 0.5091 1.1682 0.0273 0.064 Uiso 1 calc R . C32 C 0.5601(2) 1.1534(2) 0.7358(3) 0.0563(9) Uani 1 d . . H32A H 0.5297 1.1904 0.7268 0.084 Uiso 1 calc R . H32B H 0.6114 1.1591 0.7870 0.084 Uiso 1 calc R . H32C H 0.5223 1.1250 0.7761 0.084 Uiso 1 calc R . C33 C 0.6491(2) 1.1765(2) 0.5435(3) 0.0691(12) Uani 1 d . . H33A H 0.6188 1.2135 0.5337 0.104 Uiso 1 calc R . H33B H 0.6682 1.1626 0.4618 0.104 Uiso 1 calc R . H33C H 0.6990 1.1820 0.5977 0.104 Uiso 1 calc R . C34 C 0.6351(2) 1.0712(2) 0.6195(4) 0.0635(11) Uani 1 d . . H34A H 0.6859 1.0769 0.6719 0.095 Uiso 1 calc R . H34B H 0.6528 1.0567 0.5375 0.095 Uiso 1 calc R . H34C H 0.5969 1.0428 0.6590 0.095 Uiso 1 calc R . C35 C 0.5869(2) 1.13031(12) 0.6038(2) 0.0294(6) Uani 1 d . . C36 C 0.1332(2) 0.7443(2) 0.3524(3) 0.0552(9) Uani 1 d . . H36A H 0.1486 0.7701 0.4241 0.066 Uiso 1 calc R . Cl1 Cl 0.02893(7) 0.71323(5) 0.38237(10) 0.0734(3) Uani 1 d . . Cl2 Cl 0.21145(8) 0.68781(5) 0.34216(12) 0.0851(4) Uani 1 d . . Cl3 Cl 0.13335(10) 0.78699(6) 0.21384(11) 0.1014(5) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0244(11) 0.0370(12) 0.0240(11) 0.0071(10) 0.0002(8) -0.0039(9) N2 0.0156(10) 0.0501(14) 0.0270(11) 0.0112(10) -0.0017(8) -0.0047(9) N3 0.0210(11) 0.0346(12) 0.0261(11) 0.0057(10) 0.0004(8) -0.0031(9) N4 0.0203(10) 0.0269(11) 0.0245(10) 0.0031(9) 0.0007(8) -0.0056(8) N5 0.0159(10) 0.0335(12) 0.0302(11) 0.0104(10) -0.0036(8) -0.0044(9) N6 0.0228(11) 0.0284(11) 0.0257(10) 0.0054(9) -0.0017(8) -0.0054(9) O1 0.0194(8) 0.0296(9) 0.0220(8) 0.0069(7) -0.0038(6) -0.0057(7) C1 0.0309(14) 0.037(2) 0.0287(13) 0.0017(12) 0.0050(11) -0.0073(12) C2 0.049(2) 0.036(2) 0.0220(13) 0.0076(12) 0.0005(11) -0.0003(13) C3 0.038(2) 0.049(2) 0.0312(14) 0.0091(14) -0.0106(12) -0.0001(13) C4 0.0246(14) 0.049(2) 0.0350(15) 0.0115(13) -0.0036(11) -0.0020(12) C5 0.0263(13) 0.0291(13) 0.0228(12) 0.0038(11) -0.0006(9) -0.0005(10) C6 0.0180(12) 0.0338(14) 0.0247(12) 0.0036(11) -0.0026(9) -0.0028(10) C7 0.0203(12) 0.0237(12) 0.0236(12) 0.0032(10) 0.0010(9) 0.0004(10) C8 0.0225(13) 0.0298(13) 0.0227(12) 0.0014(11) -0.0019(9) 0.0000(10) C9 0.0198(12) 0.0264(13) 0.0264(12) -0.0007(11) -0.0020(9) -0.0004(10) C10 0.0180(12) 0.0319(14) 0.0299(13) 0.0008(11) 0.0012(9) -0.0033(10) C11 0.0210(12) 0.0243(13) 0.0244(12) 0.0008(10) 0.0001(9) 0.0005(10) C12 0.0147(11) 0.0241(12) 0.0244(12) 0.0016(10) -0.0026(9) -0.0011(9) C13 0.0179(12) 0.0366(14) 0.0237(12) 0.0013(11) 0.0011(9) -0.0034(10) C14 0.0208(12) 0.0234(12) 0.0200(11) -0.0014(10) 0.0006(9) -0.0017(9) C15 0.0251(12) 0.0233(12) 0.0209(12) -0.0011(10) 0.0047(9) -0.0044(10) C16 0.0288(13) 0.0213(12) 0.0181(11) 0.0003(10) 0.0009(9) 0.0022(10) C17 0.0219(12) 0.0259(13) 0.0246(12) -0.0012(11) -0.0031(9) 0.0012(10) C18 0.0221(12) 0.0196(12) 0.0208(11) 0.0005(10) 0.0005(9) -0.0014(9) C19 0.0234(12) 0.0176(11) 0.0181(11) -0.0006(10) -0.0007(9) -0.0016(9) C20 0.0186(12) 0.0284(13) 0.0248(12) 0.0015(11) -0.0018(9) -0.0020(10) C21 0.0240(12) 0.0255(13) 0.0224(12) 0.0003(10) 0.0003(9) -0.0029(10) C22 0.0196(12) 0.0336(14) 0.0351(14) 0.0059(12) -0.0047(10) -0.0017(10) C23 0.0287(14) 0.039(2) 0.040(2) 0.0054(13) -0.0062(11) 0.0060(12) C24 0.043(2) 0.0273(14) 0.0336(14) 0.0113(12) -0.0020(12) -0.0031(12) C25 0.0285(14) 0.0316(14) 0.0329(14) 0.0048(12) 0.0014(11) -0.0082(11) C26 0.0333(14) 0.0284(13) 0.0213(12) 0.0024(11) 0.0015(10) 0.0015(11) C27 0.054(2) 0.084(3) 0.039(2) 0.032(2) 0.0127(14) 0.014(2) C28 0.075(3) 0.073(3) 0.038(2) 0.024(2) -0.023(2) -0.021(2) C29 0.130(4) 0.034(2) 0.030(2) 0.0089(15) 0.007(2) 0.028(2) C30 0.031(2) 0.055(2) 0.0352(15) -0.0100(14) -0.0002(12) 0.0150(14) C31 0.030(2) 0.069(2) 0.0302(14) 0.0114(15) -0.0014(11) -0.0193(14) C32 0.037(2) 0.086(3) 0.046(2) -0.020(2) -0.0094(14) -0.003(2) C33 0.050(2) 0.103(3) 0.054(2) 0.017(2) -0.022(2) -0.045(2) C34 0.052(2) 0.063(2) 0.076(2) -0.011(2) -0.034(2) 0.019(2) C35 0.0215(13) 0.0372(15) 0.0294(13) -0.0008(12) -0.0040(10) -0.0027(11) C36 0.071(2) 0.048(2) 0.046(2) -0.004(2) -0.006(2) -0.016(2) Cl1 0.0686(7) 0.0768(7) 0.0747(7) -0.0132(5) 0.0001(5) -0.0205(5) Cl2 0.0766(8) 0.0731(7) 0.1058(9) 0.0002(6) -0.0044(6) 0.0007(6) Cl3 0.1576(13) 0.0788(8) 0.0680(7) 0.0284(6) -0.0230(7) -0.0336(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.346(3) . ? N1 C5 1.349(3) . ? N2 N3 1.375(3) . ? N2 C5 1.377(3) . ? N3 C6 1.284(3) . ? N4 C20 1.285(3) . ? N4 N5 1.374(3) . ? N5 C21 1.378(3) . ? N6 C25 1.340(3) . ? N6 C21 1.352(3) . ? O1 C12 1.376(3) . ? O1 C19 1.382(3) . ? C1 C2 1.363(4) . ? C2 C3 1.401(4) . ? C3 C4 1.374(4) . ? C4 C5 1.393(3) . ? C6 C7 1.472(3) . ? C7 C8 1.390(3) . ? C7 C12 1.405(3) . ? C8 C9 1.405(3) . ? C9 C10 1.404(3) . ? C9 C35 1.530(3) . ? C10 C11 1.387(3) . ? C11 C12 1.401(3) . ? C11 C13 1.537(3) . ? C13 C14 1.529(3) . ? C13 C31 1.539(4) . ? C13 C30 1.552(4) . ? C14 C15 1.397(3) . ? C14 C19 1.407(3) . ? C15 C16 1.394(3) . ? C16 C17 1.398(3) . ? C16 C26 1.532(3) . ? C17 C18 1.403(3) . ? C18 C19 1.397(3) . ? C18 C20 1.474(3) . ? C21 C22 1.389(3) . ? C22 C23 1.381(4) . ? C23 C24 1.386(4) . ? C24 C25 1.372(4) . ? C26 C29 1.524(4) . ? C26 C28 1.529(4) . ? C26 C27 1.535(4) . ? C32 C35 1.538(4) . ? C33 C35 1.545(4) . ? C34 C35 1.532(4) . ? C36 Cl3 1.745(4) . ? C36 Cl2 1.751(4) . ? C36 Cl1 1.769(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 C1 N1 C5 118.1(2) . . ? N3 N2 C5 120.5(2) . . ? C6 N3 N2 117.7(2) . . ? C20 N4 N5 116.0(2) . . ? N4 N5 C21 120.0(2) . . ? C25 N6 C21 117.5(2) . . ? C12 O1 C19 116.2(2) . . ? N1 C1 C2 123.8(2) . . ? C1 C2 C3 117.1(2) . . ? C4 C3 C2 120.8(2) . . ? C3 C4 C5 117.8(3) . . ? N1 C5 N2 116.2(2) . . ? N1 C5 C4 122.2(2) . . ? N2 C5 C4 121.5(2) . . ? N3 C6 C7 121.1(2) . . ? C8 C7 C12 117.4(2) . . ? C8 C7 C6 121.5(2) . . ? C12 C7 C6 121.1(2) . . ? C7 C8 C9 121.8(2) . . ? C10 C9 C8 118.4(2) . . ? C10 C9 C35 121.2(2) . . ? C8 C9 C35 120.3(2) . . ? C11 C10 C9 121.9(2) . . ? C10 C11 C12 117.6(2) . . ? C10 C11 C13 123.1(2) . . ? C12 C11 C13 119.1(2) . . ? O1 C12 C11 121.5(2) . . ? O1 C12 C7 115.6(2) . . ? C11 C12 C7 122.8(2) . . ? C14 C13 C11 107.1(2) . . ? C14 C13 C31 112.2(2) . . ? C11 C13 C31 112.5(2) . . ? C14 C13 C30 107.6(2) . . ? C11 C13 C30 108.3(2) . . ? C31 C13 C30 108.9(2) . . ? C15 C14 C19 118.8(2) . . ? C15 C14 C13 122.4(2) . . ? C19 C14 C13 118.7(2) . . ? C16 C15 C14 121.7(2) . . ? C15 C16 C17 117.1(2) . . ? C15 C16 C26 121.1(2) . . ? C17 C16 C26 121.7(2) . . ? C16 C17 C18 123.9(2) . . ? C19 C18 C17 116.5(2) . . ? C19 C18 C20 125.7(2) . . ? C17 C18 C20 117.7(2) . . ? O1 C19 C18 116.7(2) . . ? O1 C19 C14 121.5(2) . . ? C18 C19 C14 121.8(2) . . ? N4 C20 C18 125.3(2) . . ? N6 C21 N5 115.0(2) . . ? N6 C21 C22 122.6(2) . . ? N5 C21 C22 122.3(2) . . ? C23 C22 C21 117.7(2) . . ? C22 C23 C24 120.6(2) . . ? C25 C24 C23 117.3(2) . . ? N6 C25 C24 124.1(2) . . ? C29 C26 C28 108.9(3) . . ? C29 C26 C16 108.7(2) . . ? C28 C26 C16 110.1(2) . . ? C29 C26 C27 110.0(3) . . ? C28 C26 C27 106.4(3) . . ? C16 C26 C27 112.6(2) . . ? C34 C35 C9 107.2(2) . . ? C34 C35 C32 108.9(3) . . ? C9 C35 C32 111.5(2) . . ? C34 C35 C33 109.6(3) . . ? C9 C35 C33 111.8(2) . . ? C32 C35 C33 107.8(3) . . ? Cl3 C36 Cl2 110.4(2) . . ? Cl3 C36 Cl1 111.6(2) . . ? Cl2 C36 Cl1 109.7(2) . . ? _refine_diff_density_max 0.452 _refine_diff_density_min -0.616 _refine_diff_density_rms 0.109