data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C80 H120 Cl8 N32' _chemical_formula_weight 1813.68 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' 'Cl' 'Cl' 0.1484 0.1585 '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.489(3) _cell_length_b 8.687(2) _cell_length_c 19.035(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.485(4) _cell_angle_gamma 90.00 _cell_volume 2229.8(9) _cell_formula_units_Z 1 _cell_measurement_temperature 108(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.316 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.7498 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details Crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 108(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn 724' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8308 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1925 _reflns_number_gt 1723 _reflns_threshold_expression >2sigma(I) _computing_data_collection Crystalclear _computing_cell_refinement Crystalclear _computing_data_reduction Crystalclear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Shelxtl _computing_publication_material 'Shelxtl and Mercury' _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^)+(0.1379P)^2^+0.4513P] 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 1925 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1992 _refine_ls_wR_factor_gt 0.1355 _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_restrained_S_all 1.171 _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 0.5461(2) 0.7679(3) 0.83286(13) 0.0207(6) Uani 1 1 d . . . H1A H 0.5010 0.6831 0.8185 0.025 Uiso 1 1 calc R . . H1B H 0.5907 0.7890 0.7935 0.025 Uiso 1 1 calc R . . C2 C 0.4854(2) 0.9121(3) 0.84829(14) 0.0183(6) Uani 1 1 d . . . H2A H 0.5302 1.0022 0.8511 0.022 Uiso 1 1 calc R . . H2B H 0.4371 0.9299 0.8091 0.022 Uiso 1 1 calc R . . C3 C 0.4303(2) 0.8987(3) 0.91600(14) 0.0151(6) Uani 1 1 d . . . C4 C 0.34858(19) 0.9941(3) 0.92846(13) 0.0169(6) Uani 1 1 d . . . H4 H 0.3279 1.0678 0.8942 0.020 Uiso 1 1 calc R . . C5 C 0.29812(19) 0.9808(3) 0.99048(13) 0.0178(6) Uani 1 1 d . . . H5 H 0.2421 1.0433 0.9995 0.021 Uiso 1 1 calc R . . C6 C 0.33275(19) 0.8720(3) 1.03945(13) 0.0154(6) Uani 1 1 d . . . C7 C 0.45713(19) 0.7914(3) 0.96751(13) 0.0164(6) Uani 1 1 d . . . C8 C 0.5403(2) 0.6790(3) 0.95802(14) 0.0199(6) Uani 1 1 d . . . H8A H 0.5119 0.5754 0.9497 0.024 Uiso 1 1 calc R . . H8B H 0.5810 0.6746 1.0020 0.024 Uiso 1 1 calc R . . C9 C 0.60741(19) 0.7194(3) 0.89741(14) 0.0189(6) Uani 1 1 d . . . H9A H 0.6525 0.8043 0.9118 0.023 Uiso 1 1 calc R . . H9B H 0.6485 0.6290 0.8857 0.023 Uiso 1 1 calc R . . C10 C 0.3096(2) 0.7826(3) 1.16189(14) 0.0186(6) Uani 1 1 d . . . Cl1 Cl 0.37349(5) 0.59966(7) 0.33465(3) 0.0210(3) Uani 1 1 d . . . N1 N 0.25560(17) 0.8046(3) 1.21869(12) 0.0253(6) Uani 1 1 d . . . H1C H 0.2701 0.7542 1.2577 0.030 Uiso 1 1 calc R . . H1D H 0.2055 0.8694 1.2171 0.030 Uiso 1 1 calc R . . N2 N 0.38447(17) 0.6867(3) 1.16313(12) 0.0221(6) Uani 1 1 d . . . H2C H 0.3998 0.6356 1.2018 0.026 Uiso 1 1 calc R . . H2D H 0.4195 0.6732 1.1253 0.026 Uiso 1 1 calc R . . N3 N 0.40874(16) 0.7792(3) 1.02878(11) 0.0172(6) Uani 1 1 d . . . N4 N 0.28345(17) 0.8630(3) 1.10363(12) 0.0182(6) Uani 1 1 d . . . H4A H 0.2284 0.9169 1.1061 0.022 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 C1 0.0251(15) 0.0210(15) 0.0163(13) -0.0009(11) 0.0068(11) 0.0012(11) C2 0.0192(15) 0.0208(15) 0.0147(13) 0.0028(10) -0.0001(11) -0.0005(10) C3 0.0131(13) 0.0176(15) 0.0143(13) -0.0020(10) -0.0022(11) -0.0030(9) C4 0.0194(14) 0.0165(14) 0.0145(12) 0.0025(10) -0.0032(10) 0.0013(10) C5 0.0151(13) 0.0211(15) 0.0172(13) 0.0001(10) -0.0019(10) 0.0049(10) C6 0.0138(13) 0.0168(13) 0.0155(13) -0.0014(10) 0.0006(10) -0.0032(10) C7 0.0212(14) 0.0137(13) 0.0143(12) -0.0018(10) 0.0027(10) -0.0023(10) C8 0.0237(15) 0.0193(15) 0.0169(13) 0.0028(10) 0.0058(11) 0.0034(11) C9 0.0183(14) 0.0200(14) 0.0188(13) -0.0018(11) 0.0053(10) 0.0022(11) C10 0.0222(14) 0.0159(14) 0.0178(13) -0.0002(10) 0.0060(11) -0.0035(11) Cl1 0.0211(5) 0.0226(5) 0.0195(5) 0.0032(2) 0.0021(3) -0.0033(2) N1 0.0280(14) 0.0289(14) 0.0195(12) 0.0078(10) 0.0106(10) 0.0085(11) N2 0.0302(13) 0.0200(13) 0.0163(11) 0.0037(9) 0.0074(10) 0.0050(10) N3 0.0209(12) 0.0146(12) 0.0163(11) -0.0015(9) 0.0043(9) -0.0008(9) N4 0.0161(12) 0.0206(12) 0.0182(11) 0.0014(9) 0.0039(9) 0.0038(9) _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 C9 1.523(4) . ? C1 C2 1.529(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.509(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C7 1.394(4) . ? C3 C4 1.404(4) . ? C4 C5 1.383(4) . ? C4 H4 0.9500 . ? C5 C6 1.400(4) . ? C5 H5 0.9500 . ? C6 N3 1.323(4) . ? C6 N4 1.408(3) . ? C7 N3 1.355(3) . ? C7 C8 1.502(4) . ? C8 C9 1.525(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N2 1.310(4) . ? C10 N1 1.333(3) . ? C10 N4 1.349(4) . ? N1 H1C 0.8800 . ? N1 H1D 0.8800 . ? N2 H2C 0.8800 . ? N2 H2D 0.8800 . ? N4 H4A 0.8800 . ? 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 C9 C1 C2 110.8(2) . . ? C9 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? C9 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? C3 C2 C1 112.3(2) . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C7 C3 C4 117.8(2) . . ? C7 C3 C2 121.9(2) . . ? C4 C3 C2 120.3(2) . . ? C5 C4 C3 120.1(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 117.5(2) . . ? C4 C5 H5 121.2 . . ? C6 C5 H5 121.2 . . ? N3 C6 C5 123.7(2) . . ? N3 C6 N4 119.0(2) . . ? C5 C6 N4 117.3(2) . . ? N3 C7 C3 122.4(2) . . ? N3 C7 C8 115.5(2) . . ? C3 C7 C8 122.1(2) . . ? C7 C8 C9 113.7(2) . . ? C7 C8 H8A 108.8 . . ? C9 C8 H8A 108.8 . . ? C7 C8 H8B 108.8 . . ? C9 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C1 C9 C8 110.7(2) . . ? C1 C9 H9A 109.5 . . ? C8 C9 H9A 109.5 . . ? C1 C9 H9B 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? N2 C10 N1 120.9(2) . . ? N2 C10 N4 121.9(2) . . ? N1 C10 N4 117.2(2) . . ? C10 N1 H1C 120.0 . . ? C10 N1 H1D 120.0 . . ? H1C N1 H1D 120.0 . . ? C10 N2 H2C 120.0 . . ? C10 N2 H2D 120.0 . . ? H2C N2 H2D 120.0 . . ? C6 N3 C7 118.5(2) . . ? C10 N4 C6 128.5(2) . . ? C10 N4 H4A 115.7 . . ? C6 N4 H4A 115.7 . . ? 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 C9 C1 C2 C3 -48.3(3) . . . . ? C1 C2 C3 C7 18.9(3) . . . . ? C1 C2 C3 C4 -160.2(2) . . . . ? C7 C3 C4 C5 0.6(4) . . . . ? C2 C3 C4 C5 179.7(2) . . . . ? C3 C4 C5 C6 1.0(4) . . . . ? C4 C5 C6 N3 -1.9(4) . . . . ? C4 C5 C6 N4 177.6(2) . . . . ? C4 C3 C7 N3 -1.5(4) . . . . ? C2 C3 C7 N3 179.4(2) . . . . ? C4 C3 C7 C8 177.1(2) . . . . ? C2 C3 C7 C8 -2.0(4) . . . . ? N3 C7 C8 C9 -166.6(2) . . . . ? C3 C7 C8 C9 14.7(4) . . . . ? C2 C1 C9 C8 61.8(3) . . . . ? C7 C8 C9 C1 -44.0(3) . . . . ? C5 C6 N3 C7 1.1(4) . . . . ? N4 C6 N3 C7 -178.4(2) . . . . ? C3 C7 N3 C6 0.7(4) . . . . ? C8 C7 N3 C6 -178.0(2) . . . . ? N2 C10 N4 C6 -6.5(4) . . . . ? N1 C10 N4 C6 173.6(3) . . . . ? N3 C6 N4 C10 8.5(4) . . . . ? C5 C6 N4 C10 -171.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.741 _refine_diff_density_min -0.844 _refine_diff_density_rms 0.220