Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _pbl_requested_journal ' JCS Chemical Communications ' _publ_contact_author_name ' Paul E. Kruger ' _publ_contact_author_address ; Department of Chemistry Trinity College Dublin Dublin 2 Ireland ; _publ_contact_author_phone ' 353 1 608 1422 ' _publ_contact_author_fax ' 353 1 671 2826 ' _publ_contact_author_email ' paul.kruger@tcd.ie ' loop_ _publ_author_name _publ_author_address ' Paul E. Kruger ' ; Department of Chemistry Trinity College Dublin Dublin 2 Ireland ; ' John O'Brien ' ; Department of Chemistry Trinity College Dublin Dublin 2 Ireland ; ' Noreen Martin ' ; Department of Chemistry Royal College of Surgeons in Ireland Dublin 2 Ireland ; ' Jennifer Keegan ' ; Department of Chemistry Royal College of Surgeons in Ireland Dublin 2 Ireland ; ' Mark Nieuwenhuyzen ' ; Chemistry Department Queen's University Belfast, BT9 5AG UK ; _publ_section_title ; 'Anion directed assembly of a dinuclear double helicate' ; data_rdapym_(L2) _database_code_CSD 169237 audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H24 N4' _chemical_formula_weight 380.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.5546(8) _cell_length_b 8.1809(5) _cell_length_c 21.5214(14) _cell_angle_alpha 90.00 _cell_angle_beta 97.8810(10) _cell_angle_gamma 90.00 _cell_volume 2015.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 1500 _cell_measurement_theta_min 4 _cell_measurement_theta_max 40 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9646 _exptl_absorpt_correction_T_max 0.9865 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 22756 _diffrn_reflns_av_R_equivalents 0.0604 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.74 _reflns_number_total 4724 _reflns_number_gt 3620 _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^)+(0.0707P)^2^+0.3199P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4724 _refine_ls_number_parameters 358 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1275 _refine_ls_wR_factor_gt 0.1156 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.02497(11) -1.31473(15) 0.16050(6) 0.0347(3) Uani 1 1 d . . . C2 C -0.01060(14) -1.3862(2) 0.21071(8) 0.0397(4) Uani 1 1 d . . . H2 H -0.0868(14) -1.440(2) 0.2030(8) 0.040(4) Uiso 1 1 d . . . C3 C 0.05341(14) -1.3854(2) 0.26982(7) 0.0383(4) Uani 1 1 d . . . H3 H 0.0245(14) -1.443(2) 0.3043(8) 0.043(5) Uiso 1 1 d . . . C4 C 0.15895(14) -1.3035(2) 0.27799(7) 0.0358(3) Uani 1 1 d . . . H4 H 0.2047(15) -1.297(2) 0.3184(9) 0.044(5) Uiso 1 1 d . . . C5 C 0.19723(12) -1.22778(17) 0.22681(7) 0.0298(3) Uani 1 1 d . . . H5 H 0.2703(14) -1.167(2) 0.2300(8) 0.036(4) Uiso 1 1 d . . . C6 C 0.12888(11) -1.23858(15) 0.16866(6) 0.0250(3) Uani 1 1 d . . . C7 C 0.16510(13) -1.16846(18) 0.10869(7) 0.0297(3) Uani 1 1 d . . . H7A H 0.1081(13) -1.0727(19) 0.0936(7) 0.031(4) Uiso 1 1 d . . . H7B H 0.1548(13) -1.2564(19) 0.0774(7) 0.031(4) Uiso 1 1 d . . . N8 N 0.28439(11) -1.11189(14) 0.11398(6) 0.0312(3) Uani 1 1 d . . . H8 H 0.3366(15) -1.179(2) 0.1041(8) 0.036(4) Uiso 1 1 d . . . C9 C 0.32192(11) -0.95673(15) 0.13240(6) 0.0239(3) Uani 1 1 d . . . C10 C 0.44143(11) -0.91804(16) 0.13419(6) 0.0260(3) Uani 1 1 d . . . H10 H 0.4944(13) -1.0022(19) 0.1223(7) 0.029(4) Uiso 1 1 d . . . C11 C 0.48201(12) -0.76402(17) 0.15210(6) 0.0267(3) Uani 1 1 d . . . H11 H 0.5632(14) -0.7399(19) 0.1538(7) 0.033(4) Uiso 1 1 d . . . C12 C 0.40823(11) -0.64136(16) 0.16907(6) 0.0249(3) Uani 1 1 d . . . C13 C 0.29009(12) -0.67972(17) 0.16626(6) 0.0274(3) Uani 1 1 d . . . H13 H 0.2360(13) -0.5962(19) 0.1793(7) 0.030(4) Uiso 1 1 d . . . C14 C 0.24682(12) -0.83449(17) 0.14864(6) 0.0271(3) Uani 1 1 d . . . H13' H 0.1624(14) -0.858(2) 0.1476(7) 0.037(4) Uiso 1 1 d . . . C15 C 0.45602(13) -0.47541(18) 0.19127(7) 0.0302(3) Uani 1 1 d . . . H15A H 0.5066(12) -0.4871(19) 0.2314(7) 0.028(4) Uiso 1 1 d . . . H15B H 0.3902(14) -0.4047(19) 0.1995(7) 0.031(4) Uiso 1 1 d . . . C16 C 0.52620(11) -0.39002(15) 0.14604(6) 0.0237(3) Uani 1 1 d . . . C17 C 0.63176(12) -0.31269(16) 0.16695(6) 0.0258(3) Uani 1 1 d . . . H17 H 0.6596(13) -0.3148(19) 0.2118(8) 0.033(4) Uiso 1 1 d . . . C18 C 0.69697(11) -0.23365(16) 0.12606(6) 0.0253(3) Uani 1 1 d . . . H18 H 0.7716(13) -0.1823(18) 0.1430(7) 0.027(4) Uiso 1 1 d . . . C19 C 0.65837(11) -0.23237(14) 0.06148(6) 0.0220(3) Uani 1 1 d . . . C20 C 0.54990(11) -0.30521(15) 0.04028(6) 0.0227(3) Uani 1 1 d . . . H20 H 0.5207(13) -0.3048(19) -0.0044(8) 0.032(4) Uiso 1 1 d . . . C21 C 0.48639(11) -0.38301(15) 0.08171(6) 0.0235(3) Uani 1 1 d . . . H21 H 0.4124(13) -0.4346(18) 0.0659(7) 0.027(4) Uiso 1 1 d . . . N22 N 0.72341(10) -0.16741(14) 0.01808(6) 0.0285(3) Uani 1 1 d . . . H22 H 0.6932(14) -0.171(2) -0.0214(8) 0.034(4) Uiso 1 1 d . . . C23 C 0.83763(12) -0.09501(16) 0.03351(7) 0.0263(3) Uani 1 1 d . . . H23A H 0.8839(13) -0.1542(19) 0.0695(7) 0.031(4) Uiso 1 1 d . . . H23B H 0.8785(13) -0.1121(18) -0.0019(7) 0.029(4) Uiso 1 1 d . . . C24 C 0.83816(11) 0.08619(15) 0.04902(6) 0.0227(3) Uani 1 1 d . . . C25 C 0.73657(12) 0.17853(17) 0.04617(6) 0.0262(3) Uani 1 1 d . . . H25 H 0.6619(14) 0.1229(19) 0.0363(8) 0.035(4) Uiso 1 1 d . . . C26 C 0.74585(12) 0.34572(17) 0.05657(7) 0.0295(3) Uani 1 1 d . . . H26 H 0.6746(14) 0.412(2) 0.0556(8) 0.037(4) Uiso 1 1 d . . . C27 C 0.85566(13) 0.41543(17) 0.06940(7) 0.0314(3) Uani 1 1 d . . . H27 H 0.8693(15) 0.530(2) 0.0777(9) 0.050(5) Uiso 1 1 d . . . C28 C 0.95212(12) 0.31379(18) 0.07272(7) 0.0316(3) Uani 1 1 d . . . H28 H 1.0344(14) 0.3599(19) 0.0815(8) 0.036(4) Uiso 1 1 d . . . N29 N 0.94533(9) 0.15156(14) 0.06326(6) 0.0277(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0316(6) 0.0375(7) 0.0333(7) 0.0055(5) -0.0012(5) -0.0102(5) C2 0.0343(8) 0.0436(9) 0.0409(9) 0.0059(7) 0.0039(7) -0.0122(7) C3 0.0430(9) 0.0412(9) 0.0322(8) 0.0059(7) 0.0108(7) -0.0024(7) C4 0.0380(8) 0.0440(9) 0.0246(7) -0.0017(6) 0.0017(6) 0.0007(7) C5 0.0271(7) 0.0314(7) 0.0305(7) -0.0045(6) 0.0020(6) -0.0016(6) C6 0.0260(7) 0.0210(6) 0.0279(7) -0.0013(5) 0.0029(5) -0.0004(5) C7 0.0318(7) 0.0286(7) 0.0281(7) -0.0001(6) 0.0021(6) -0.0070(6) N8 0.0286(6) 0.0272(6) 0.0391(7) -0.0029(5) 0.0095(5) -0.0020(5) C9 0.0256(6) 0.0255(6) 0.0203(6) 0.0049(5) 0.0020(5) -0.0016(5) C10 0.0242(7) 0.0269(7) 0.0273(7) 0.0030(5) 0.0052(5) 0.0034(5) C11 0.0207(6) 0.0322(7) 0.0272(7) 0.0035(5) 0.0034(5) -0.0016(5) C12 0.0268(7) 0.0281(7) 0.0201(6) 0.0030(5) 0.0042(5) -0.0015(5) C13 0.0267(7) 0.0285(7) 0.0277(7) 0.0015(5) 0.0064(5) 0.0026(5) C14 0.0212(6) 0.0309(7) 0.0295(7) 0.0030(6) 0.0040(5) -0.0004(5) C15 0.0335(8) 0.0303(7) 0.0279(7) -0.0044(6) 0.0086(6) -0.0058(6) C16 0.0243(6) 0.0211(6) 0.0257(7) -0.0029(5) 0.0036(5) 0.0005(5) C17 0.0278(7) 0.0273(7) 0.0209(7) -0.0025(5) -0.0013(5) -0.0001(5) C18 0.0220(6) 0.0253(6) 0.0273(7) -0.0022(5) -0.0013(5) -0.0031(5) C19 0.0228(6) 0.0170(6) 0.0261(6) 0.0000(5) 0.0025(5) 0.0017(5) C20 0.0238(6) 0.0205(6) 0.0226(7) -0.0019(5) -0.0013(5) 0.0024(5) C21 0.0205(6) 0.0208(6) 0.0284(7) -0.0041(5) 0.0009(5) 0.0004(5) N22 0.0302(6) 0.0302(6) 0.0246(6) 0.0019(5) 0.0016(5) -0.0068(5) C23 0.0245(7) 0.0237(6) 0.0314(7) 0.0017(5) 0.0062(6) -0.0001(5) C24 0.0234(6) 0.0243(6) 0.0206(6) 0.0024(5) 0.0032(5) 0.0000(5) C25 0.0222(7) 0.0296(7) 0.0262(7) 0.0008(5) 0.0009(5) 0.0008(5) C26 0.0282(7) 0.0294(7) 0.0297(7) -0.0007(5) 0.0003(6) 0.0072(6) C27 0.0349(8) 0.0239(7) 0.0341(8) -0.0021(6) -0.0001(6) 0.0000(6) C28 0.0264(7) 0.0294(7) 0.0381(8) -0.0020(6) 0.0010(6) -0.0034(6) N29 0.0223(6) 0.0268(6) 0.0335(6) 0.0000(5) 0.0025(5) -0.0003(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 N1 C2 1.3418(19) . ? N1 C6 1.3425(17) . ? C2 C3 1.381(2) . ? C3 C4 1.381(2) . ? C4 C5 1.388(2) . ? C5 C6 1.388(2) . ? C6 C7 1.5225(19) . ? C7 N8 1.4437(18) . ? N8 C9 1.3817(17) . ? C9 C14 1.3995(18) . ? C9 C10 1.4120(18) . ? C10 C11 1.3808(19) . ? C11 C12 1.3973(19) . ? C12 C13 1.3939(18) . ? C12 C15 1.5179(19) . ? C13 C14 1.395(2) . ? C15 C16 1.5197(18) . ? C16 C17 1.3928(18) . ? C16 C21 1.3988(18) . ? C17 C18 1.3937(19) . ? C18 C19 1.4002(18) . ? C19 N22 1.3828(17) . ? C19 C20 1.4062(18) . ? C20 C21 1.3850(18) . ? N22 C23 1.4431(17) . ? C23 C24 1.5193(18) . ? C24 N29 1.3450(16) . ? C24 C25 1.3902(17) . ? C25 C26 1.3878(19) . ? C26 C27 1.384(2) . ? C27 C28 1.385(2) . ? C28 N29 1.3434(18) . ? 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 N1 C6 117.65(13) . . ? N1 C2 C3 123.72(14) . . ? C2 C3 C4 118.14(14) . . ? C3 C4 C5 119.17(14) . . ? C4 C5 C6 118.89(13) . . ? N1 C6 C5 122.38(13) . . ? N1 C6 C7 114.13(12) . . ? C5 C6 C7 123.48(12) . . ? N8 C7 C6 115.12(12) . . ? C9 N8 C7 125.16(12) . . ? N8 C9 C14 123.17(12) . . ? N8 C9 C10 118.75(12) . . ? C14 C9 C10 118.07(12) . . ? C11 C10 C9 120.37(12) . . ? C10 C11 C12 122.17(12) . . ? C13 C12 C11 117.12(12) . . ? C13 C12 C15 121.80(12) . . ? C11 C12 C15 121.06(12) . . ? C12 C13 C14 121.92(13) . . ? C13 C14 C9 120.35(12) . . ? C12 C15 C16 114.37(11) . . ? C17 C16 C21 117.11(12) . . ? C17 C16 C15 121.49(12) . . ? C21 C16 C15 121.39(12) . . ? C16 C17 C18 122.14(12) . . ? C17 C18 C19 120.27(12) . . ? N22 C19 C18 123.00(12) . . ? N22 C19 C20 119.11(12) . . ? C18 C19 C20 117.86(12) . . ? C21 C20 C19 120.87(12) . . ? C20 C21 C16 121.65(12) . . ? C19 N22 C23 124.53(12) . . ? N22 C23 C24 115.28(11) . . ? N29 C24 C25 122.64(12) . . ? N29 C24 C23 114.45(11) . . ? C25 C24 C23 122.85(12) . . ? C26 C25 C24 118.83(12) . . ? C27 C26 C25 119.13(13) . . ? C26 C27 C28 118.19(13) . . ? N29 C28 C27 123.75(13) . . ? C28 N29 C24 117.40(11) . . ? _diffrn_measured_fraction_theta_max 0.905 _diffrn_reflns_theta_full 28.74 _diffrn_measured_fraction_theta_full 0.905 _refine_diff_density_max 0.291 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.057 #---END data_rdapy1m_(1) _database_code_CSD 169238 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H29 Cl4 N4 O0.50' _chemical_formula_weight 535.31 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' 'Cl' 'Cl' 0.1484 0.1585 '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 Pnna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x+1/2, y+1/2, -z+1/2' 'x, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x-1/2, -y-1/2, z-1/2' '-x, y-1/2, z-1/2' _cell_length_a 17.656(4) _cell_length_b 24.275(6) _cell_length_c 12.263(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5256(2) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2361 _cell_measurement_theta_min 2 _cell_measurement_theta_max 38 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2232 _exptl_absorpt_coefficient_mu 0.474 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.510 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 48268 _diffrn_reflns_av_R_equivalents 0.1325 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4638 _reflns_number_gt 2488 _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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4638 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1092 _refine_ls_R_factor_gt 0.0662 _refine_ls_wR_factor_ref 0.1878 _refine_ls_wR_factor_gt 0.1625 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.961 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_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_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 0.10473(5) 0.36187(4) 0.93672(7) 0.0477(3) Uani 1 1 d . . . Cl2 Cl 0.11274(5) 0.63712(4) 0.56522(7) 0.0460(3) Uani 1 1 d . . . Cl3 Cl 0.12308(6) 0.49726(3) 0.74793(8) 0.0525(3) Uani 1 1 d . . . Cl4 Cl 0.08323(8) 0.2500 0.2500 0.0583(4) Uani 1 2 d S . . Cl5 Cl 0.09348(8) 0.7500 0.2500 0.0731(5) Uani 1 2 d S . . N1A N 0.13834(16) 0.61331(11) 0.8382(2) 0.0434(8) Uani 1 1 d . . . H1A H 0.1368 0.5800 0.8100 0.052 Uiso 1 1 calc R . . C2A C 0.2058(2) 0.63492(16) 0.8608(3) 0.0578(11) Uani 1 1 d . . . H2A H 0.2509 0.6147 0.8474 0.069 Uiso 1 1 calc R . . C3A C 0.2086(3) 0.68704(18) 0.9040(5) 0.0899(18) Uani 1 1 d . . . H3A H 0.2562 0.7034 0.9203 0.108 Uiso 1 1 calc R . . C4A C 0.1427(3) 0.71549(18) 0.9236(5) 0.0919(18) Uani 1 1 d . . . H4A H 0.1443 0.7515 0.9537 0.110 Uiso 1 1 calc R . . C5A C 0.0741(2) 0.69119(17) 0.8992(4) 0.0678(13) Uani 1 1 d . . . H5A H 0.0280 0.7102 0.9125 0.081 Uiso 1 1 calc R . . C6A C 0.0734(2) 0.63906(15) 0.8555(3) 0.0425(9) Uani 1 1 d . . . C7A C 0.00191(18) 0.61027(14) 0.8230(3) 0.0426(9) Uani 1 1 d . . . H7A H -0.0380 0.6176 0.8778 0.051 Uiso 1 1 calc R . . H7BB H 0.0108 0.5700 0.8206 0.051 Uiso 1 1 calc R . . N8A N -0.02404(14) 0.62987(11) 0.7133(2) 0.0359(7) Uani 1 1 d . . . H8A1 H -0.0427 0.6651 0.7199 0.043 Uiso 1 1 calc R . . H8A2 H 0.0169 0.6311 0.6669 0.043 Uiso 1 1 calc R . . C9A C -0.08244(17) 0.59481(13) 0.6654(3) 0.0341(8) Uani 1 1 d . . . C10A C -0.15733(18) 0.60950(15) 0.6741(3) 0.0466(10) Uani 1 1 d . . . H10A H -0.1716 0.6413 0.7143 0.056 Uiso 1 1 calc R . . C11A C -0.21184(18) 0.57733(16) 0.6235(3) 0.0496(10) Uani 1 1 d . . . H11A H -0.2638 0.5872 0.6288 0.060 Uiso 1 1 calc R . . C12A C -0.19115(18) 0.53091(15) 0.5652(3) 0.0395(9) Uani 1 1 d . . . C13A C -0.11640(19) 0.51615(15) 0.5607(3) 0.0421(9) Uani 1 1 d . . . H13A H -0.1021 0.4838 0.5224 0.050 Uiso 1 1 calc R . . C14A C -0.06103(18) 0.54783(14) 0.6114(3) 0.0409(9) Uani 1 1 d . . . H14A H -0.0093 0.5371 0.6086 0.049 Uiso 1 1 calc R . . C15A C -0.2500 0.5000 0.5002(4) 0.0503(15) Uani 1 2 d S . . H15A H -0.2765 0.5266 0.4524 0.060 Uiso 0.50 1 calc PR . . H15B H -0.2235 0.4734 0.4524 0.060 Uiso 0.50 1 calc PR . . N1B N 0.12601(16) 0.38302(11) 0.6483(2) 0.0428(7) Uani 1 1 d . . . H1B H 0.1277 0.4148 0.6828 0.051 Uiso 1 1 calc R . . C2B C 0.1900(2) 0.36188(17) 0.6114(4) 0.0596(12) Uani 1 1 d . . . H2B H 0.2364 0.3811 0.6211 0.072 Uiso 1 1 calc R . . C3B C 0.1887(2) 0.31224(18) 0.5594(4) 0.0710(14) Uani 1 1 d . . . H3B H 0.2346 0.2966 0.5331 0.085 Uiso 1 1 calc R . . C4B C 0.1219(2) 0.28492(17) 0.5450(4) 0.0667(13) Uani 1 1 d . . . H4B H 0.1208 0.2504 0.5085 0.080 Uiso 1 1 calc R . . C5B C 0.0555(2) 0.30833(15) 0.5844(3) 0.0518(10) Uani 1 1 d . . . H5B H 0.0084 0.2899 0.5758 0.062 Uiso 1 1 calc R . . C6B C 0.0587(2) 0.35838(14) 0.6358(3) 0.0407(9) Uani 1 1 d . . . C7B C -0.00915(18) 0.38833(14) 0.6785(3) 0.0402(9) Uani 1 1 d . . . H7C H 0.0020 0.4283 0.6820 0.048 Uiso 1 1 calc R . . H7D H -0.0522 0.3829 0.6280 0.048 Uiso 1 1 calc R . . N8B N -0.03052(14) 0.36822(11) 0.7891(2) 0.0355(7) Uani 1 1 d . . . H8B1 H -0.0488 0.3329 0.7836 0.043 Uiso 1 1 calc R . . H8B2 H 0.0120 0.3673 0.8325 0.043 Uiso 1 1 calc R . . C9B C -0.08795(17) 0.40306(13) 0.8412(3) 0.0346(8) Uani 1 1 d . . . C10B C -0.06535(19) 0.45217(14) 0.8876(3) 0.0430(9) Uani 1 1 d . . . H10B H -0.0140 0.4637 0.8834 0.052 Uiso 1 1 calc R . . C11B C -0.1189(2) 0.48425(15) 0.9403(3) 0.0433(9) Uani 1 1 d . . . H11B H -0.1041 0.5182 0.9724 0.052 Uiso 1 1 calc R . . C12B C -0.19337(18) 0.46751(15) 0.9467(3) 0.0400(9) Uani 1 1 d . . . C13B C -0.21449(19) 0.41886(16) 0.8976(3) 0.0513(10) Uani 1 1 d . . . H13B H -0.2660 0.4077 0.9001 0.062 Uiso 1 1 calc R . . C14B C -0.16215(18) 0.38605(15) 0.8449(3) 0.0475(10) Uani 1 1 d . . . H14B H -0.1771 0.3524 0.8119 0.057 Uiso 1 1 calc R . . C15B C -0.2500 0.5000 1.0124(4) 0.0535(16) Uani 1 2 d S . . H15C H -0.2220 0.5258 1.0602 0.064 Uiso 0.50 1 calc PR . . H15D H -0.2780 0.4742 1.0602 0.064 Uiso 0.50 1 calc PR . . O1W O 0.2468(4) 0.2464(3) 0.3544(9) 0.132(3) Uiso 0.50 1 d P . . 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 0.0377(5) 0.0572(6) 0.0483(6) 0.0030(5) -0.0016(4) 0.0068(4) Cl2 0.0366(5) 0.0569(6) 0.0443(6) 0.0023(5) 0.0000(4) -0.0060(4) Cl3 0.0581(7) 0.0490(6) 0.0503(6) -0.0073(5) -0.0034(5) -0.0032(4) Cl4 0.0558(9) 0.0430(8) 0.0762(10) -0.0075(8) 0.000 0.000 Cl5 0.0609(10) 0.0415(8) 0.1168(14) -0.0098(9) 0.000 0.000 N1A 0.0475(18) 0.0353(17) 0.0475(19) 0.0035(14) -0.0089(15) -0.0045(14) C2A 0.050(2) 0.050(3) 0.074(3) 0.005(2) -0.023(2) -0.0047(19) C3A 0.068(3) 0.047(3) 0.155(5) -0.005(3) -0.061(3) -0.005(2) C4A 0.078(3) 0.047(3) 0.151(5) -0.026(3) -0.059(3) -0.001(2) C5A 0.066(3) 0.051(3) 0.086(3) -0.021(2) -0.033(2) 0.005(2) C6A 0.046(2) 0.042(2) 0.039(2) 0.0001(17) -0.0080(17) -0.0071(18) C7A 0.048(2) 0.046(2) 0.034(2) -0.0034(17) -0.0011(17) -0.0135(16) N8A 0.0319(15) 0.0361(16) 0.0396(18) -0.0059(13) 0.0002(12) -0.0070(13) C9A 0.0317(17) 0.040(2) 0.0309(19) -0.0005(16) -0.0002(15) -0.0075(15) C10A 0.035(2) 0.052(2) 0.053(2) -0.0172(19) 0.0051(18) -0.0013(17) C11A 0.0229(18) 0.069(3) 0.057(3) -0.012(2) 0.0061(16) -0.0066(17) C12A 0.0368(19) 0.049(2) 0.033(2) 0.0049(18) 0.0012(16) -0.0136(16) C13A 0.042(2) 0.039(2) 0.045(2) -0.0060(18) -0.0008(17) -0.0067(16) C14A 0.0282(18) 0.045(2) 0.050(2) -0.0079(18) -0.0004(16) -0.0003(16) C15A 0.039(3) 0.071(4) 0.041(3) 0.000 0.000 -0.023(3) N1B 0.0487(19) 0.0385(17) 0.0412(18) 0.0007(14) 0.0029(15) 0.0033(14) C2B 0.046(2) 0.055(3) 0.078(3) 0.013(2) 0.022(2) 0.009(2) C3B 0.054(3) 0.059(3) 0.100(4) 0.006(3) 0.034(3) 0.016(2) C4B 0.074(3) 0.042(2) 0.084(3) -0.008(2) 0.025(3) 0.013(2) C5B 0.049(2) 0.045(2) 0.061(3) -0.009(2) 0.0075(19) 0.0004(18) C6B 0.044(2) 0.041(2) 0.038(2) 0.0007(17) 0.0037(16) 0.0052(17) C7B 0.041(2) 0.045(2) 0.035(2) -0.0008(17) 0.0008(16) 0.0120(16) N8B 0.0323(15) 0.0350(16) 0.0391(18) -0.0012(13) 0.0011(12) 0.0076(12) C9B 0.0334(18) 0.038(2) 0.0324(19) -0.0028(16) 0.0017(15) 0.0086(15) C10B 0.0346(19) 0.044(2) 0.051(2) -0.0038(18) 0.0037(17) 0.0013(16) C11B 0.049(2) 0.039(2) 0.041(2) -0.0031(18) 0.0003(18) 0.0081(17) C12B 0.0370(19) 0.051(2) 0.032(2) 0.0051(17) -0.0007(15) 0.0175(17) C13B 0.032(2) 0.068(3) 0.054(2) -0.007(2) -0.0032(18) 0.0068(19) C14B 0.032(2) 0.053(2) 0.058(3) -0.0129(19) -0.0037(18) -0.0005(17) C15B 0.050(3) 0.077(4) 0.034(3) 0.000 0.000 0.033(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 N1A C6A 1.322(4) . ? N1A C2A 1.330(4) . ? C2A C3A 1.372(6) . ? C3A C4A 1.375(6) . ? C4A C5A 1.379(6) . ? C5A C6A 1.374(5) . ? C6A C7A 1.497(4) . ? C7A N8A 1.498(4) . ? N8A C9A 1.460(4) . ? C9A C14A 1.372(4) . ? C9A C10A 1.374(4) . ? C10A C11A 1.386(5) . ? C11A C12A 1.383(5) . ? C12A C13A 1.369(5) . ? C12A C15A 1.510(4) . ? C13A C14A 1.390(4) . ? C15A C12A 1.510(4) 2_465 ? N1B C2B 1.321(4) . ? N1B C6B 1.339(4) . ? C2B C3B 1.364(6) . ? C3B C4B 1.365(6) . ? C4B C5B 1.391(5) . ? C5B C6B 1.370(5) . ? C6B C7B 1.496(4) . ? C7B N8B 1.490(4) . ? N8B C9B 1.467(4) . ? C9B C14B 1.374(4) . ? C9B C10B 1.380(4) . ? C10B C11B 1.384(4) . ? C11B C12B 1.379(5) . ? C12B C13B 1.377(5) . ? C12B C15B 1.507(4) . ? C13B C14B 1.381(5) . ? C15B C12B 1.507(4) 2_465 ? 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 C6A N1A C2A 123.7(3) . . ? N1A C2A C3A 118.5(4) . . ? C2A C3A C4A 120.0(4) . . ? C3A C4A C5A 119.4(4) . . ? C6A C5A C4A 119.1(4) . . ? N1A C6A C5A 119.4(3) . . ? N1A C6A C7A 117.9(3) . . ? C5A C6A C7A 122.8(4) . . ? C6A C7A N8A 110.4(3) . . ? C9A N8A C7A 113.1(2) . . ? C14A C9A C10A 121.2(3) . . ? C14A C9A N8A 119.0(3) . . ? C10A C9A N8A 119.8(3) . . ? C9A C10A C11A 119.2(3) . . ? C12A C11A C10A 120.5(3) . . ? C13A C12A C11A 119.3(3) . . ? C13A C12A C15A 120.8(3) . . ? C11A C12A C15A 119.7(3) . . ? C12A C13A C14A 121.0(3) . . ? C9A C14A C13A 118.8(3) . . ? C12A C15A C12A 116.2(4) 2_465 . ? C2B N1B C6B 123.1(3) . . ? N1B C2B C3B 119.3(4) . . ? C2B C3B C4B 120.3(4) . . ? C3B C4B C5B 119.1(4) . . ? C6B C5B C4B 119.1(4) . . ? N1B C6B C5B 119.1(3) . . ? N1B C6B C7B 117.0(3) . . ? C5B C6B C7B 123.9(3) . . ? N8B C7B C6B 111.2(3) . . ? C9B N8B C7B 112.5(2) . . ? C14B C9B C10B 121.5(3) . . ? C14B C9B N8B 120.0(3) . . ? C10B C9B N8B 118.5(3) . . ? C9B C10B C11B 118.7(3) . . ? C12B C11B C10B 120.8(3) . . ? C13B C12B C11B 119.1(3) . . ? C13B C12B C15B 120.2(3) . . ? C11B C12B C15B 120.6(3) . . ? C12B C13B C14B 121.2(3) . . ? C9B C14B C13B 118.7(3) . . ? C12B C15B C12B 115.4(4) . 2_465 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.462 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.091