# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Kung Wang' _publ_contact_author_email KUNG.WANG@MAIL.WVU.EDU loop_ _publ_author_name K.Wang J.L.Petersen B.Wen # Attachment 'meso8a.cif' data_bw4ccd _database_code_depnum_ccdc_archive 'CCDC 750093' #TrackingRef 'meso8a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H40 N2' _chemical_formula_weight 620.80 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.4736(7) _cell_length_b 5.9821(3) _cell_length_c 24.7092(14) _cell_angle_alpha 90.00 _cell_angle_beta 100.7890(10) _cell_angle_gamma 90.00 _cell_volume 1811.17(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5737 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 27.48 _exptl_crystal_description 'irregular fragment' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.138 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.974 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4 automated diffractometer' _diffrn_measurement_method 'Smart 1K CCD detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 11727 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0692 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4067 _reflns_number_gt 2850 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART version 5.6' _computing_cell_refinement 'SMART version 5.6' _computing_data_reduction 'SAINT version 5/6.0' _computing_structure_solution 'SHELXTL 6.1' _computing_structure_refinement 'SHELXTL 6.1' _computing_molecular_graphics ? _computing_publication_material 'SHELXTL 6.1' _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^)+(0.0799P)^2^+0.2633P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4067 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1768 _refine_ls_wR_factor_gt 0.1552 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.14292(16) 0.3341(3) -0.07769(7) 0.0751(5) Uani 1 1 d . . . C1 C 0.55243(14) 1.1012(3) -0.03772(7) 0.0539(4) Uani 1 1 d . . . H1 H 0.5885 1.1711 -0.0628 0.065 Uiso 1 1 calc R . . C2 C 0.55860(14) 1.1931(3) 0.01455(7) 0.0538(4) Uani 1 1 d . . . H2 H 0.5983 1.3237 0.0237 0.065 Uiso 1 1 calc R . . C3 C 0.50672(13) 1.0937(3) 0.05319(7) 0.0476(4) Uani 1 1 d . . . C4 C 0.51661(13) 1.1938(3) 0.11070(7) 0.0477(4) Uani 1 1 d . . . H4 H 0.5324 1.3531 0.1072 0.057 Uiso 1 1 calc R . . C5 C 0.61256(13) 1.0968(3) 0.15476(7) 0.0530(4) Uani 1 1 d . . . C6 C 0.60086(19) 0.8432(3) 0.16023(10) 0.0776(6) Uani 1 1 d . . . H6A H 0.6072 0.7726 0.1261 0.116 Uiso 1 1 calc R . . H6B H 0.5308 0.8095 0.1689 0.116 Uiso 1 1 calc R . . H6C H 0.6572 0.7887 0.1891 0.116 Uiso 1 1 calc R . . C7 C 0.72109(16) 1.1509(4) 0.13786(10) 0.0814(7) Uani 1 1 d . . . H7A H 0.7287 1.3100 0.1352 0.122 Uiso 1 1 calc R . . H7B H 0.7231 1.0839 0.1028 0.122 Uiso 1 1 calc R . . H7C H 0.7798 1.0928 0.1649 0.122 Uiso 1 1 calc R . . C8 C 0.61043(17) 1.2062(4) 0.21048(8) 0.0724(6) Uani 1 1 d . . . H8A H 0.6710 1.1530 0.2372 0.109 Uiso 1 1 calc R . . H8B H 0.5435 1.1687 0.2221 0.109 Uiso 1 1 calc R . . H8C H 0.6155 1.3655 0.2071 0.109 Uiso 1 1 calc R . . C9 C 0.41199(13) 1.1818(3) 0.12991(7) 0.0501(4) Uani 1 1 d . . . C10 C 0.32696(13) 1.1754(3) 0.14508(6) 0.0502(4) Uani 1 1 d . . . C11 C 0.22616(12) 1.1725(3) 0.16534(6) 0.0476(4) Uani 1 1 d . . . C12 C 0.21211(14) 1.3138(3) 0.20819(7) 0.0597(5) Uani 1 1 d . . . H12 H 0.2672 1.4137 0.2227 0.072 Uiso 1 1 calc R . . C13 C 0.11746(15) 1.3076(3) 0.22943(8) 0.0654(5) Uani 1 1 d . . . H13 H 0.1091 1.4031 0.2580 0.078 Uiso 1 1 calc R . . C14 C 0.03547(15) 1.1608(3) 0.20850(8) 0.0635(5) Uani 1 1 d . . . H14 H -0.0276 1.1555 0.2235 0.076 Uiso 1 1 calc R . . C15 C 0.04609(14) 1.0216(3) 0.16545(8) 0.0597(5) Uani 1 1 d . . . H15 H -0.0102 0.9241 0.1512 0.072 Uiso 1 1 calc R . . C16 C 0.14106(13) 1.0260(3) 0.14310(7) 0.0497(4) Uani 1 1 d . . . C17 C 0.14986(14) 0.8852(3) 0.09716(7) 0.0553(4) Uani 1 1 d . . . C18 C 0.15214(14) 0.7700(3) 0.05811(7) 0.0571(4) Uani 1 1 d . . . C19 C 0.15105(13) 0.6258(3) 0.01152(7) 0.0508(4) Uani 1 1 d . . . C20 C 0.08318(16) 0.6656(3) -0.03821(8) 0.0609(5) Uani 1 1 d . . . H20 H 0.0388 0.7917 -0.0431 0.073 Uiso 1 1 calc R . . C21 C 0.08185(18) 0.5160(3) -0.08070(8) 0.0708(5) Uani 1 1 d . . . H21 H 0.0347 0.5449 -0.1138 0.085 Uiso 1 1 calc R . . C22 C 0.2086(2) 0.2995(3) -0.02995(10) 0.0790(6) Uani 1 1 d . . . H22 H 0.2531 0.1736 -0.0267 0.095 Uiso 1 1 calc R . . C23 C 0.21591(18) 0.4361(3) 0.01528(8) 0.0686(5) Uani 1 1 d . . . H23 H 0.2636 0.4019 0.0479 0.082 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 N1 0.0927(13) 0.0662(9) 0.0672(11) -0.0174(8) 0.0168(10) -0.0037(9) C1 0.0542(10) 0.0624(9) 0.0500(9) -0.0016(7) 0.0225(7) -0.0105(7) C2 0.0540(9) 0.0569(9) 0.0540(10) -0.0052(7) 0.0191(8) -0.0128(7) C3 0.0428(8) 0.0554(8) 0.0476(9) -0.0031(7) 0.0159(7) -0.0009(6) C4 0.0456(8) 0.0508(8) 0.0496(9) -0.0048(7) 0.0165(7) -0.0030(6) C5 0.0421(8) 0.0633(9) 0.0535(10) -0.0062(8) 0.0090(7) -0.0018(7) C6 0.0768(14) 0.0688(11) 0.0813(15) 0.0063(10) -0.0003(11) 0.0069(10) C7 0.0425(10) 0.1174(17) 0.0865(15) -0.0152(13) 0.0175(10) -0.0079(10) C8 0.0623(12) 0.0978(14) 0.0549(11) -0.0126(10) 0.0053(9) -0.0045(10) C9 0.0474(9) 0.0619(9) 0.0421(8) -0.0035(7) 0.0115(7) 0.0021(7) C10 0.0443(8) 0.0668(9) 0.0404(8) -0.0018(7) 0.0099(6) 0.0023(7) C11 0.0395(8) 0.0641(9) 0.0399(8) -0.0016(7) 0.0093(6) 0.0052(7) C12 0.0465(9) 0.0773(11) 0.0560(10) -0.0177(9) 0.0116(8) -0.0025(8) C13 0.0528(10) 0.0892(13) 0.0562(10) -0.0215(10) 0.0154(8) 0.0038(9) C14 0.0447(9) 0.0918(13) 0.0580(11) -0.0112(9) 0.0196(8) 0.0033(9) C15 0.0467(9) 0.0780(11) 0.0556(10) -0.0103(9) 0.0125(8) -0.0052(8) C16 0.0450(8) 0.0621(9) 0.0423(8) -0.0042(7) 0.0086(6) 0.0034(7) C17 0.0485(9) 0.0658(9) 0.0526(10) -0.0059(8) 0.0118(7) -0.0002(7) C18 0.0542(10) 0.0656(9) 0.0538(10) -0.0083(8) 0.0157(8) -0.0046(8) C19 0.0502(9) 0.0546(8) 0.0502(9) -0.0050(7) 0.0164(7) -0.0060(7) C20 0.0638(11) 0.0597(9) 0.0582(11) -0.0042(8) 0.0087(9) 0.0012(8) C21 0.0817(14) 0.0740(12) 0.0531(11) -0.0050(9) 0.0035(10) -0.0066(10) C22 0.0949(16) 0.0615(11) 0.0797(15) -0.0125(10) 0.0139(13) 0.0156(10) C23 0.0780(13) 0.0672(10) 0.0573(11) -0.0022(9) 0.0041(9) 0.0119(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 N1 C22 1.320(3) . ? N1 C21 1.322(3) . ? C1 C2 1.393(2) . ? C1 C3 1.394(2) 3_675 ? C2 C3 1.384(2) . ? C3 C1 1.394(2) 3_675 ? C3 C4 1.526(2) . ? C4 C9 1.471(2) . ? C4 C5 1.571(2) . ? C5 C7 1.524(2) . ? C5 C8 1.529(2) . ? C5 C6 1.532(3) . ? C9 C10 1.190(2) . ? C10 C11 1.438(2) . ? C11 C12 1.392(2) . ? C11 C16 1.407(2) . ? C12 C13 1.379(2) . ? C13 C14 1.373(3) . ? C14 C15 1.377(2) . ? C15 C16 1.398(2) . ? C16 C17 1.434(2) . ? C17 C18 1.190(2) . ? C18 C19 1.437(2) . ? C19 C20 1.376(3) . ? C19 C23 1.387(2) . ? C20 C21 1.377(3) . ? C22 C23 1.374(3) . ? 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 C22 N1 C21 115.69(17) . . ? C2 C1 C3 121.27(15) . 3_675 ? C3 C2 C1 121.23(15) . . ? C2 C3 C1 117.50(15) . 3_675 ? C2 C3 C4 120.49(14) . . ? C1 C3 C4 122.00(14) 3_675 . ? C9 C4 C3 111.06(13) . . ? C9 C4 C5 111.41(13) . . ? C3 C4 C5 114.76(13) . . ? C7 C5 C8 108.77(16) . . ? C7 C5 C6 109.79(17) . . ? C8 C5 C6 109.04(17) . . ? C7 C5 C4 109.40(15) . . ? C8 C5 C4 109.05(14) . . ? C6 C5 C4 110.75(15) . . ? C10 C9 C4 178.95(19) . . ? C9 C10 C11 177.72(18) . . ? C12 C11 C16 118.86(14) . . ? C12 C11 C10 120.04(15) . . ? C16 C11 C10 121.10(14) . . ? C13 C12 C11 120.78(16) . . ? C14 C13 C12 120.28(16) . . ? C13 C14 C15 120.34(16) . . ? C14 C15 C16 120.34(16) . . ? C15 C16 C11 119.38(15) . . ? C15 C16 C17 119.86(15) . . ? C11 C16 C17 120.74(14) . . ? C18 C17 C16 176.95(19) . . ? C17 C18 C19 177.58(18) . . ? C20 C19 C23 117.06(16) . . ? C20 C19 C18 121.59(16) . . ? C23 C19 C18 121.32(17) . . ? C19 C20 C21 119.08(17) . . ? N1 C21 C20 124.56(19) . . ? N1 C22 C23 124.71(19) . . ? C22 C23 C19 118.89(19) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.233 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.041 # Attachment 'rac8a.cif' data_bw5ccd _database_code_depnum_ccdc_archive 'CCDC 750094' #TrackingRef 'rac8a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H40 N2' _chemical_formula_weight 620.80 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 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 13.0021(11) _cell_length_b 18.4591(17) _cell_length_c 15.6235(14) _cell_angle_alpha 90.00 _cell_angle_beta 103.267(2) _cell_angle_gamma 90.00 _cell_volume 3649.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5155 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 27.24 _exptl_crystal_description 'irregular fragment' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.130 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4 automated diffractometer' _diffrn_measurement_method 'Smart 1K CCD detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 24767 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.0698 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.51 _reflns_number_total 8186 _reflns_number_gt 4978 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART version 5.6' _computing_cell_refinement 'SMART version 5.6' _computing_data_reduction 'SAINT version 5/6.0' _computing_structure_solution 'SHELXTL version 6.1' _computing_structure_refinement 'SHELXTL version 6.1' _computing_molecular_graphics ? _computing_publication_material 'SHELXTL version 6.1' _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^)+(0.0751P)^2^+0.3057P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8186 _refine_ls_number_parameters 439 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0905 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1694 _refine_ls_wR_factor_gt 0.1427 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.004 _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 0.70630(9) 0.37394(8) 0.94371(9) 0.0931(4) Uani 1 1 d . . . N2 N 0.25324(8) 0.09133(8) 0.73046(9) 0.0949(4) Uani 1 1 d . . . C1 C 0.47117(8) 0.39387(6) 0.65193(8) 0.0576(3) Uani 1 1 d . . . H1 H 0.5002 0.4387 0.6714 0.069 Uiso 1 1 calc R . . C2 C 0.36498(8) 0.38195(6) 0.64594(8) 0.0570(3) Uani 1 1 d . . . H2 H 0.3241 0.4182 0.6627 0.068 Uiso 1 1 calc R . . C3 C 0.31856(8) 0.31644(6) 0.61514(7) 0.0524(3) Uani 1 1 d . . . C4 C 0.38295(8) 0.26362(6) 0.59219(8) 0.0602(3) Uani 1 1 d . . . H4 H 0.3536 0.2193 0.5710 0.072 Uiso 1 1 calc R . . C5 C 0.48969(9) 0.27515(6) 0.60008(8) 0.0608(3) Uani 1 1 d . . . H5 H 0.5312 0.2383 0.5853 0.073 Uiso 1 1 calc R . . C6 C 0.53569(8) 0.34071(6) 0.62967(7) 0.0533(3) Uani 1 1 d . . . C7 C 0.20102(8) 0.30156(6) 0.60582(7) 0.0547(3) Uani 1 1 d . . . H7 H 0.1923 0.2489 0.6002 0.066 Uiso 1 1 calc R . . C8 C 0.16677(8) 0.32210(6) 0.68610(8) 0.0579(3) Uani 1 1 d . . . C9 C 0.13837(8) 0.33933(6) 0.75043(8) 0.0577(3) Uani 1 1 d . . . C10 C 0.10073(8) 0.36214(6) 0.82576(8) 0.0570(3) Uani 1 1 d . . . C11 C -0.00658(9) 0.35990(7) 0.82408(9) 0.0693(4) Uani 1 1 d . . . H11 H -0.0536 0.3428 0.7741 0.083 Uiso 1 1 calc R . . C12 C -0.04465(11) 0.38244(8) 0.89464(11) 0.0864(4) Uani 1 1 d . . . H12 H -0.1168 0.3806 0.8919 0.104 Uiso 1 1 calc R . . C13 C 0.02347(13) 0.40776(9) 0.96925(11) 0.0979(5) Uani 1 1 d . . . H13 H -0.0025 0.4231 1.0170 0.118 Uiso 1 1 calc R . . C14 C 0.12935(13) 0.41031(9) 0.97308(10) 0.0891(5) Uani 1 1 d . . . H14 H 0.1751 0.4278 1.0236 0.107 Uiso 1 1 calc R . . C15 C 0.17038(10) 0.38711(7) 0.90227(8) 0.0664(3) Uani 1 1 d . . . C16 C 0.28210(11) 0.38679(7) 0.90959(9) 0.0723(4) Uani 1 1 d . . . C17 C 0.37595(11) 0.38430(8) 0.91919(9) 0.0724(4) Uani 1 1 d . . . C18 C 0.48744(10) 0.37972(7) 0.92845(8) 0.0649(3) Uani 1 1 d . . . C19 C 0.55861(10) 0.41194(8) 0.99861(8) 0.0721(4) Uani 1 1 d . . . H19 H 0.5343 0.4359 1.0425 0.087 Uiso 1 1 calc R . . C20 C 0.66432(11) 0.40786(9) 1.00211(9) 0.0830(5) Uani 1 1 d . . . H20 H 0.7101 0.4305 1.0489 0.100 Uiso 1 1 calc R . . C21 C 0.63784(12) 0.34185(9) 0.87790(10) 0.0915(5) Uani 1 1 d . . . H21 H 0.6650 0.3166 0.8365 0.110 Uiso 1 1 calc R . . C22 C 0.53013(11) 0.34359(8) 0.86713(9) 0.0771(4) Uani 1 1 d . . . H22 H 0.4864 0.3208 0.8192 0.093 Uiso 1 1 calc R . . C23 C 0.12720(9) 0.33518(7) 0.52115(8) 0.0634(3) Uani 1 1 d . . . C24 C 0.17307(12) 0.31821(11) 0.44242(9) 0.0983(5) Uani 1 1 d . . . H24A H 0.1249 0.3340 0.3896 0.147 Uiso 1 1 calc R . . H24B H 0.1840 0.2669 0.4394 0.147 Uiso 1 1 calc R . . H24C H 0.2393 0.3429 0.4484 0.147 Uiso 1 1 calc R . . C25 C 0.11596(11) 0.41675(8) 0.52960(10) 0.0840(5) Uani 1 1 d . . . H25A H 0.1841 0.4392 0.5373 0.126 Uiso 1 1 calc R . . H25B H 0.0870 0.4272 0.5795 0.126 Uiso 1 1 calc R . . H25C H 0.0697 0.4353 0.4773 0.126 Uiso 1 1 calc R . . C26 C 0.01860(10) 0.30057(9) 0.50881(11) 0.0918(5) Uani 1 1 d . . . H26A H -0.0291 0.3227 0.4597 0.138 Uiso 1 1 calc R . . H26B H -0.0073 0.3075 0.5610 0.138 Uiso 1 1 calc R . . H26C H 0.0237 0.2497 0.4979 0.138 Uiso 1 1 calc R . . C27 C 0.65404(8) 0.35496(6) 0.64096(8) 0.0571(3) Uani 1 1 d . . . H27 H 0.6736 0.3912 0.6877 0.068 Uiso 1 1 calc R . . C28 C 0.71552(8) 0.28940(6) 0.67230(7) 0.0557(3) Uani 1 1 d . . . C29 C 0.76445(8) 0.23515(6) 0.69323(7) 0.0544(3) Uani 1 1 d . . . C30 C 0.82602(7) 0.17054(6) 0.71469(7) 0.0499(3) Uani 1 1 d . . . C31 C 0.93178(8) 0.16973(7) 0.71043(8) 0.0630(3) Uani 1 1 d . . . H31 H 0.9627 0.2118 0.6952 0.076 Uiso 1 1 calc R . . C32 C 0.99129(8) 0.10744(7) 0.72846(9) 0.0718(4) Uani 1 1 d . . . H32 H 1.0617 0.1077 0.7249 0.086 Uiso 1 1 calc R . . C33 C 0.94707(9) 0.04505(7) 0.75169(10) 0.0779(4) Uani 1 1 d . . . H33 H 0.9879 0.0034 0.7648 0.093 Uiso 1 1 calc R . . C34 C 0.84280(9) 0.04402(7) 0.75559(9) 0.0700(4) Uani 1 1 d . . . H34 H 0.8131 0.0014 0.7705 0.084 Uiso 1 1 calc R . . C35 C 0.78100(8) 0.10599(6) 0.73752(7) 0.0527(3) Uani 1 1 d . . . C36 C 0.67123(8) 0.10308(7) 0.73957(8) 0.0591(3) Uani 1 1 d . . . C37 C 0.57987(8) 0.09919(7) 0.73946(8) 0.0611(3) Uani 1 1 d . . . C38 C 0.46907(8) 0.09621(6) 0.73768(7) 0.0553(3) Uani 1 1 d . . . C39 C 0.40670(8) 0.03983(7) 0.69673(8) 0.0646(3) Uani 1 1 d . . . H39 H 0.4359 0.0025 0.6701 0.078 Uiso 1 1 calc R . . C40 C 0.30147(10) 0.03990(9) 0.69598(10) 0.0837(5) Uani 1 1 d . . . H40 H 0.2610 0.0010 0.6693 0.100 Uiso 1 1 calc R . . C41 C 0.31289(11) 0.14533(9) 0.76841(11) 0.0939(5) Uani 1 1 d . . . H41 H 0.2804 0.1827 0.7922 0.113 Uiso 1 1 calc R . . C42 C 0.42101(10) 0.15014(8) 0.77525(10) 0.0759(4) Uani 1 1 d . . . H42 H 0.4599 0.1887 0.8044 0.091 Uiso 1 1 calc R . . C43 C 0.68766(9) 0.38661(7) 0.55837(10) 0.0745(4) Uani 1 1 d . . . C44 C 0.80328(10) 0.40995(9) 0.58719(13) 0.1038(6) Uani 1 1 d . . . H44A H 0.8261 0.4294 0.5377 0.156 Uiso 1 1 calc R . . H44B H 0.8461 0.3688 0.6099 0.156 Uiso 1 1 calc R . . H44C H 0.8102 0.4463 0.6321 0.156 Uiso 1 1 calc R . . C45 C 0.62082(12) 0.45264(10) 0.52484(14) 0.1218(6) Uani 1 1 d . . . H45A H 0.6256 0.4869 0.5718 0.183 Uiso 1 1 calc R . . H45B H 0.5485 0.4382 0.5037 0.183 Uiso 1 1 calc R . . H45C H 0.6461 0.4746 0.4778 0.183 Uiso 1 1 calc R . . C46 C 0.67543(14) 0.32949(11) 0.48583(11) 0.1086(6) Uani 1 1 d . . . H46A H 0.6945 0.3502 0.4352 0.163 Uiso 1 1 calc R . . H46B H 0.6034 0.3134 0.4701 0.163 Uiso 1 1 calc R . . H46C H 0.7208 0.2891 0.5066 0.163 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 N1 0.0825(7) 0.1166(10) 0.0812(8) 0.0181(7) 0.0208(6) 0.0124(7) N2 0.0573(5) 0.1232(11) 0.1074(9) 0.0242(8) 0.0252(6) 0.0086(6) C1 0.0589(5) 0.0437(6) 0.0663(7) -0.0063(5) 0.0066(5) 0.0043(5) C2 0.0588(5) 0.0467(6) 0.0638(7) -0.0101(5) 0.0103(5) 0.0103(5) C3 0.0575(5) 0.0485(6) 0.0487(6) -0.0019(5) 0.0071(5) 0.0060(5) C4 0.0647(6) 0.0444(6) 0.0680(7) -0.0095(5) 0.0083(5) 0.0037(5) C5 0.0616(6) 0.0496(6) 0.0688(7) -0.0081(5) 0.0098(5) 0.0119(5) C6 0.0554(5) 0.0476(6) 0.0538(6) 0.0017(5) 0.0059(5) 0.0079(5) C7 0.0588(5) 0.0493(6) 0.0547(6) -0.0030(5) 0.0103(5) 0.0000(5) C8 0.0582(5) 0.0540(6) 0.0597(7) 0.0020(5) 0.0095(5) -0.0001(5) C9 0.0596(5) 0.0533(6) 0.0588(7) 0.0029(5) 0.0107(5) 0.0006(5) C10 0.0645(6) 0.0485(6) 0.0585(6) 0.0043(5) 0.0150(5) 0.0025(5) C11 0.0655(6) 0.0642(8) 0.0797(8) 0.0066(6) 0.0200(6) 0.0040(6) C12 0.0829(7) 0.0778(9) 0.1099(10) 0.0110(8) 0.0455(7) 0.0137(7) C13 0.1239(10) 0.0894(11) 0.0962(10) -0.0069(8) 0.0576(8) 0.0083(9) C14 0.1163(10) 0.0856(10) 0.0673(8) -0.0161(7) 0.0252(8) -0.0051(9) C15 0.0757(7) 0.0610(7) 0.0621(7) 0.0023(6) 0.0147(6) -0.0030(6) C16 0.0804(7) 0.0694(8) 0.0616(7) 0.0012(6) 0.0051(6) -0.0092(7) C17 0.0772(7) 0.0706(8) 0.0639(8) 0.0066(6) 0.0051(6) -0.0085(6) C18 0.0772(7) 0.0605(7) 0.0534(6) 0.0108(5) 0.0075(6) -0.0018(6) C19 0.0743(7) 0.0868(9) 0.0533(7) 0.0007(6) 0.0105(6) -0.0023(7) C20 0.0790(8) 0.1023(11) 0.0620(8) 0.0071(8) 0.0041(7) -0.0060(8) C21 0.1150(10) 0.0921(11) 0.0729(9) 0.0082(8) 0.0329(8) 0.0225(9) C22 0.0987(9) 0.0693(8) 0.0591(7) 0.0029(6) 0.0097(7) 0.0034(7) C23 0.0603(6) 0.0677(8) 0.0581(7) -0.0040(6) 0.0048(5) 0.0056(6) C24 0.0939(9) 0.1405(14) 0.0558(8) -0.0046(9) 0.0073(7) 0.0225(10) C25 0.0873(8) 0.0697(9) 0.0845(9) 0.0126(7) -0.0017(7) 0.0110(7) C26 0.0657(7) 0.0992(11) 0.0991(11) -0.0133(9) -0.0047(7) -0.0037(7) C27 0.0547(5) 0.0482(6) 0.0639(7) 0.0021(5) 0.0044(5) 0.0096(5) C28 0.0519(5) 0.0563(6) 0.0563(6) 0.0027(5) 0.0073(5) 0.0060(5) C29 0.0487(5) 0.0543(6) 0.0582(6) 0.0038(5) 0.0083(5) 0.0039(5) C30 0.0452(4) 0.0503(6) 0.0514(6) 0.0010(5) 0.0052(4) 0.0053(4) C31 0.0482(5) 0.0617(7) 0.0783(8) -0.0008(6) 0.0128(5) -0.0006(5) C32 0.0428(5) 0.0767(8) 0.0933(9) -0.0139(7) 0.0098(6) 0.0095(5) C33 0.0613(6) 0.0599(7) 0.1039(10) -0.0017(7) 0.0012(7) 0.0165(6) C34 0.0652(6) 0.0517(7) 0.0886(9) 0.0088(6) 0.0083(6) 0.0055(6) C35 0.0474(5) 0.0541(6) 0.0540(6) 0.0037(5) 0.0063(4) 0.0029(5) C36 0.0576(5) 0.0612(7) 0.0580(6) 0.0057(5) 0.0127(5) 0.0008(5) C37 0.0559(5) 0.0653(7) 0.0633(7) 0.0064(6) 0.0158(5) -0.0002(5) C38 0.0524(5) 0.0603(7) 0.0544(6) 0.0115(5) 0.0144(5) 0.0017(5) C39 0.0604(6) 0.0663(7) 0.0663(7) 0.0039(6) 0.0128(5) 0.0004(6) C40 0.0601(6) 0.1004(11) 0.0853(9) 0.0122(8) 0.0060(6) -0.0105(7) C41 0.0871(7) 0.1016(11) 0.1057(10) 0.0141(9) 0.0484(7) 0.0286(8) C42 0.0763(7) 0.0714(8) 0.0859(9) -0.0051(7) 0.0309(6) 0.0018(6) C43 0.0653(6) 0.0698(8) 0.0878(9) 0.0299(7) 0.0164(6) 0.0159(6) C44 0.0678(7) 0.1006(11) 0.1458(14) 0.0448(10) 0.0304(8) 0.0101(8) C45 0.0895(8) 0.1120(11) 0.1694(15) 0.0839(10) 0.0412(9) 0.0398(8) C46 0.1307(12) 0.1305(15) 0.0688(9) 0.0198(9) 0.0314(9) 0.0191(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 N1 C20 1.323(2) . ? N1 C21 1.334(2) . ? N2 C41 1.317(2) . ? N2 C40 1.319(2) . ? C1 C2 1.3800(15) . ? C1 C6 1.3862(15) . ? C2 C3 1.3874(15) . ? C3 C4 1.3849(16) . ? C3 C7 1.5266(15) . ? C4 C5 1.3814(16) . ? C5 C6 1.3816(16) . ? C6 C27 1.5309(14) . ? C7 C8 1.4736(17) . ? C7 C23 1.5728(16) . ? C8 C9 1.1908(17) . ? C9 C10 1.4374(17) . ? C10 C11 1.3901(16) . ? C10 C15 1.4017(16) . ? C11 C12 1.372(2) . ? C12 C13 1.374(2) . ? C13 C14 1.365(2) . ? C14 C15 1.401(2) . ? C15 C16 1.4308(18) . ? C16 C17 1.1956(19) . ? C17 C18 1.4259(18) . ? C18 C22 1.384(2) . ? C18 C19 1.3949(17) . ? C19 C20 1.3649(19) . ? C21 C22 1.372(2) . ? C23 C24 1.518(2) . ? C23 C26 1.5212(18) . ? C23 C25 1.5214(19) . ? C27 C28 1.4708(15) . ? C27 C43 1.5673(19) . ? C28 C29 1.1913(15) . ? C29 C30 1.4326(15) . ? C30 C31 1.3919(14) . ? C30 C35 1.4091(15) . ? C31 C32 1.3784(17) . ? C32 C33 1.373(2) . ? C33 C34 1.3712(17) . ? C34 C35 1.3892(16) . ? C35 C36 1.4358(15) . ? C36 C37 1.1897(15) . ? C37 C38 1.4355(15) . ? C38 C42 1.3762(18) . ? C38 C39 1.3828(17) . ? C39 C40 1.3656(17) . ? C41 C42 1.3881(19) . ? C43 C45 1.519(2) . ? C43 C44 1.5290(18) . ? C43 C46 1.529(2) . ? 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 C20 N1 C21 115.69(13) . . ? C41 N2 C40 116.26(12) . . ? C2 C1 C6 121.58(10) . . ? C1 C2 C3 120.75(10) . . ? C4 C3 C2 117.57(10) . . ? C4 C3 C7 120.00(10) . . ? C2 C3 C7 122.43(10) . . ? C5 C4 C3 121.53(11) . . ? C4 C5 C6 120.92(10) . . ? C5 C6 C1 117.62(10) . . ? C5 C6 C27 122.38(10) . . ? C1 C6 C27 119.97(10) . . ? C8 C7 C3 111.35(9) . . ? C8 C7 C23 111.66(9) . . ? C3 C7 C23 114.43(9) . . ? C9 C8 C7 179.22(13) . . ? C8 C9 C10 177.52(12) . . ? C11 C10 C15 118.36(12) . . ? C11 C10 C9 120.31(11) . . ? C15 C10 C9 121.32(10) . . ? C12 C11 C10 121.42(12) . . ? C11 C12 C13 120.23(13) . . ? C14 C13 C12 119.75(15) . . ? C13 C14 C15 121.18(14) . . ? C14 C15 C10 119.04(12) . . ? C14 C15 C16 120.12(12) . . ? C10 C15 C16 120.81(12) . . ? C17 C16 C15 176.77(15) . . ? C16 C17 C18 178.21(16) . . ? C22 C18 C19 116.77(12) . . ? C22 C18 C17 121.21(12) . . ? C19 C18 C17 122.02(12) . . ? C20 C19 C18 119.23(13) . . ? N1 C20 C19 124.70(13) . . ? N1 C21 C22 124.46(15) . . ? C21 C22 C18 119.12(13) . . ? C24 C23 C26 109.67(12) . . ? C24 C23 C25 109.76(13) . . ? C26 C23 C25 108.77(11) . . ? C24 C23 C7 108.83(10) . . ? C26 C23 C7 108.08(11) . . ? C25 C23 C7 111.70(10) . . ? C28 C27 C6 110.61(9) . . ? C28 C27 C43 110.36(10) . . ? C6 C27 C43 115.60(9) . . ? C29 C28 C27 176.57(12) . . ? C28 C29 C30 176.99(13) . . ? C31 C30 C35 118.38(10) . . ? C31 C30 C29 120.19(10) . . ? C35 C30 C29 121.39(9) . . ? C32 C31 C30 120.91(12) . . ? C33 C32 C31 120.28(11) . . ? C34 C33 C32 120.11(12) . . ? C33 C34 C35 120.76(12) . . ? C34 C35 C30 119.55(10) . . ? C34 C35 C36 119.75(11) . . ? C30 C35 C36 120.67(10) . . ? C37 C36 C35 178.13(14) . . ? C36 C37 C38 178.39(14) . . ? C42 C38 C39 117.79(10) . . ? C42 C38 C37 121.06(11) . . ? C39 C38 C37 121.14(11) . . ? C40 C39 C38 118.90(13) . . ? N2 C40 C39 124.50(14) . . ? N2 C41 C42 124.35(15) . . ? C38 C42 C41 118.15(13) . . ? C45 C43 C44 108.76(12) . . ? C45 C43 C46 110.10(13) . . ? C44 C43 C46 109.91(13) . . ? C45 C43 C27 109.73(12) . . ? C44 C43 C27 107.68(11) . . ? C46 C43 C27 110.61(12) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.166 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.036 # Attachment 'cmpd2c.cif' data_bw6plt _database_code_depnum_ccdc_archive 'CCDC 750095' #TrackingRef 'cmpd2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C68 H56 Cl4 N6' _chemical_formula_weight 1098.99 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' _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 27.005(2) _cell_length_b 14.7364(12) _cell_length_c 17.7781(15) _cell_angle_alpha 90.00 _cell_angle_beta 128.084(2) _cell_angle_gamma 90.00 _cell_volume 5568.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8183 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 27.40 _exptl_crystal_description 'irregular fragment' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2296 _exptl_absorpt_coefficient_mu 0.262 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.867 _exptl_absorpt_correction_T_max 0.954 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4 automated diffractometer' _diffrn_measurement_method 'Smart 1K CCD detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 18930 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0812 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.54 _reflns_number_total 6323 _reflns_number_gt 3872 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART version 5.6' _computing_cell_refinement 'SMART version 5.6' _computing_data_reduction 'SAINT version 5/6.0' _computing_structure_solution 'SHELXTL 6.1' _computing_structure_refinement 'SHELXTL 6.1' _computing_molecular_graphics ? _computing_publication_material 'SHELXTL 6.1' _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. The crystallographic asymmetric unit contains a badly disordered molecule of methylene chloride located in a general position. It was treated as a diffuse electron density contribution with the aid of the SQUEEZE routine in the program PLATON. Although specific positions for the independent carbon, hydrogen, and chlorine atoms of the methylene chloride molecule were not determined, the calculated density, absorption coefficient, and empirical formula weight reflect their presence within the crystal lattice. ; _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^)+(0.1252P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6323 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0951 _refine_ls_R_factor_gt 0.0665 _refine_ls_wR_factor_ref 0.2032 _refine_ls_wR_factor_gt 0.1843 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _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 N1 N 1.01724(7) 0.70953(11) 0.93604(10) 0.0486(4) Uani 1 1 d . . . N2 N 1.07154(8) 0.91571(14) 1.07469(13) 0.0678(5) Uani 1 1 d . . . N3 N 0.93135(8) 0.55579(12) 0.73590(12) 0.0608(4) Uani 1 1 d . . . C1 C 0.92915(7) 0.90611(12) 0.70898(11) 0.0411(4) Uani 1 1 d . . . C2 C 0.86412(7) 0.91147(12) 0.63704(12) 0.0438(4) Uani 1 1 d . . . C3 C 0.81229(7) 0.85825(13) 0.62194(12) 0.0481(4) Uani 1 1 d . . . C4 C 0.80946(9) 0.79551(15) 0.67721(15) 0.0564(5) Uani 1 1 d . . . H4 H 0.8459 0.7783 0.7366 0.068 Uiso 1 1 calc R . . C5 C 0.75142(10) 0.75838(18) 0.64292(18) 0.0692(6) Uani 1 1 d . . . H5 H 0.7491 0.7170 0.6802 0.083 Uiso 1 1 calc R . . C6 C 0.69735(10) 0.7826(2) 0.55393(19) 0.0767(7) Uani 1 1 d . . . H6 H 0.6594 0.7551 0.5307 0.092 Uiso 1 1 calc R . . C7 C 0.69887(9) 0.84697(18) 0.49923(17) 0.0694(6) Uani 1 1 d . . . H7 H 0.6622 0.8642 0.4402 0.083 Uiso 1 1 calc R . . C8 C 0.75625(8) 0.88568(15) 0.53383(14) 0.0551(5) Uani 1 1 d . . . C9 C 0.76868(8) 0.95834(16) 0.48926(14) 0.0597(5) Uani 1 1 d . . . H9A H 0.7434 1.0117 0.4759 0.072 Uiso 1 1 calc R . . H9B H 0.7597 0.9373 0.4303 0.072 Uiso 1 1 calc R . . C10 C 0.83859(8) 0.97883(13) 0.56432(12) 0.0481(4) Uani 1 1 d . . . C11 C 0.87357(8) 1.05362(14) 0.57307(14) 0.0515(5) Uani 1 1 d . . . C12 C 0.93654(8) 1.05879(13) 0.66085(14) 0.0487(4) Uani 1 1 d . . . C13 C 0.96549(7) 0.97890(12) 0.71543(12) 0.0430(4) Uani 1 1 d . . . C14 C 0.97218(10) 1.14056(14) 0.70591(16) 0.0599(5) Uani 1 1 d . . . H14 H 0.9562 1.1952 0.6730 0.072 Uiso 1 1 calc R . . C15 C 0.95893(7) 0.83638(12) 0.78645(11) 0.0415(4) Uani 1 1 d . . . C16 C 0.99652(7) 0.86367(13) 0.88190(12) 0.0447(4) Uani 1 1 d . . . H16 H 1.0025 0.9250 0.8974 0.054 Uiso 1 1 calc R . . C17 C 1.02504(7) 0.79852(13) 0.95380(12) 0.0459(4) Uani 1 1 d . . . C18 C 0.98028(8) 0.68216(13) 0.84392(12) 0.0456(4) Uani 1 1 d . . . C19 C 0.95079(7) 0.74371(12) 0.76782(12) 0.0431(4) Uani 1 1 d . . . H19 H 0.9259 0.7228 0.7051 0.052 Uiso 1 1 calc R . . C20 C 0.84794(10) 1.12796(17) 0.49610(17) 0.0679(6) Uani 1 1 d . . . C21 C 0.82090(17) 1.2065(2) 0.5183(3) 0.1100(12) Uani 1 1 d . . . H21A H 0.7873 1.1841 0.5178 0.165 Uiso 1 1 calc R . . H21B H 0.8051 1.2530 0.4708 0.165 Uiso 1 1 calc R . . H21C H 0.8535 1.2311 0.5802 0.165 Uiso 1 1 calc R . . C22 C 0.79639(14) 1.0926(3) 0.3955(2) 0.1023(11) Uani 1 1 d . . . H22A H 0.8102 1.0374 0.3850 0.153 Uiso 1 1 calc R . . H22B H 0.7877 1.1372 0.3494 0.153 Uiso 1 1 calc R . . H22C H 0.7589 1.0811 0.3890 0.153 Uiso 1 1 calc R . . C23 C 0.90008(13) 1.1623(2) 0.4906(2) 0.0851(8) Uani 1 1 d . . . H23A H 0.9325 1.1920 0.5494 0.128 Uiso 1 1 calc R . . H23B H 0.8822 1.2045 0.4387 0.128 Uiso 1 1 calc R . . H23C H 0.9177 1.1118 0.4804 0.128 Uiso 1 1 calc R . . C24 C 1.06691(8) 0.82666(14) 1.05650(12) 0.0493(4) Uani 1 1 d . . . C25 C 1.10080(10) 0.76301(18) 1.12878(14) 0.0654(6) Uani 1 1 d . . . H25 H 1.0973 0.7014 1.1148 0.078 Uiso 1 1 calc R . . C26 C 1.14027(12) 0.7936(2) 1.22278(17) 0.0830(8) Uani 1 1 d . . . H26 H 1.1641 0.7523 1.2726 0.100 Uiso 1 1 calc R . . C27 C 1.14393(11) 0.8829(2) 1.24156(16) 0.0779(7) Uani 1 1 d . . . H27 H 1.1693 0.9042 1.3041 0.093 Uiso 1 1 calc R . . C28 C 1.10935(11) 0.9412(2) 1.16632(17) 0.0758(7) Uani 1 1 d . . . H28 H 1.1123 1.0029 1.1797 0.091 Uiso 1 1 calc R . . C29 C 0.97233(9) 0.58293(13) 0.82724(13) 0.0503(4) Uani 1 1 d . . . C30 C 1.00530(12) 0.52145(15) 0.90213(17) 0.0660(6) Uani 1 1 d . . . H30 H 1.0335 0.5422 0.9647 0.079 Uiso 1 1 calc R . . C31 C 0.99634(14) 0.42973(16) 0.8839(2) 0.0794(7) Uani 1 1 d . . . H31 H 1.0180 0.3878 0.9335 0.095 Uiso 1 1 calc R . . C32 C 0.95439(14) 0.40160(17) 0.7900(2) 0.0807(7) Uani 1 1 d . . . H32 H 0.9471 0.3402 0.7748 0.097 Uiso 1 1 calc R . . C33 C 0.92383(13) 0.46641(17) 0.71994(18) 0.0727(6) Uani 1 1 d . . . H33 H 0.8959 0.4468 0.6569 0.087 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 N1 0.0498(7) 0.0505(9) 0.0425(8) 0.0025(7) 0.0270(6) 0.0011(6) N2 0.0681(10) 0.0701(13) 0.0511(9) -0.0125(8) 0.0297(8) 0.0020(9) N3 0.0755(10) 0.0491(10) 0.0584(10) -0.0057(8) 0.0417(9) -0.0081(8) C1 0.0392(7) 0.0411(9) 0.0398(8) -0.0007(7) 0.0227(6) 0.0009(6) C2 0.0388(7) 0.0490(10) 0.0404(8) -0.0004(7) 0.0228(7) 0.0008(7) C3 0.0394(7) 0.0566(11) 0.0454(9) -0.0051(8) 0.0246(7) -0.0033(7) C4 0.0507(9) 0.0651(13) 0.0571(10) -0.0039(9) 0.0351(8) -0.0074(9) C5 0.0617(11) 0.0762(16) 0.0818(15) -0.0074(12) 0.0503(11) -0.0144(11) C6 0.0489(10) 0.0914(19) 0.0881(16) -0.0173(14) 0.0413(11) -0.0202(11) C7 0.0398(8) 0.0856(17) 0.0656(12) -0.0118(12) 0.0238(9) -0.0073(9) C8 0.0411(8) 0.0646(13) 0.0519(10) -0.0061(9) 0.0248(8) -0.0014(8) C9 0.0400(8) 0.0745(14) 0.0498(10) 0.0062(9) 0.0202(8) 0.0092(8) C10 0.0416(8) 0.0556(11) 0.0445(9) 0.0038(8) 0.0252(7) 0.0080(7) C11 0.0486(8) 0.0515(11) 0.0562(10) 0.0116(8) 0.0332(8) 0.0134(8) C12 0.0492(8) 0.0426(10) 0.0590(10) 0.0063(8) 0.0358(8) 0.0069(7) C13 0.0404(8) 0.0404(9) 0.0466(9) -0.0013(7) 0.0260(7) 0.0017(7) C14 0.0636(10) 0.0388(10) 0.0824(14) 0.0056(9) 0.0476(10) 0.0054(8) C15 0.0371(7) 0.0426(9) 0.0411(8) -0.0001(7) 0.0223(6) -0.0013(6) C16 0.0423(7) 0.0457(10) 0.0416(8) -0.0014(7) 0.0236(7) -0.0013(7) C17 0.0393(7) 0.0530(11) 0.0424(8) 0.0010(7) 0.0236(7) 0.0007(7) C18 0.0476(8) 0.0450(10) 0.0453(9) 0.0022(7) 0.0292(7) -0.0008(7) C19 0.0417(7) 0.0431(10) 0.0409(8) -0.0006(7) 0.0236(7) -0.0032(7) C20 0.0641(11) 0.0686(15) 0.0731(13) 0.0294(11) 0.0434(11) 0.0236(10) C21 0.129(2) 0.089(2) 0.144(3) 0.063(2) 0.100(2) 0.0683(19) C22 0.0829(16) 0.137(3) 0.0678(15) 0.0454(17) 0.0368(13) 0.0133(17) C23 0.0923(17) 0.0897(19) 0.0902(17) 0.0317(15) 0.0647(15) 0.0131(14) C24 0.0435(8) 0.0594(12) 0.0450(9) -0.0019(8) 0.0273(7) -0.0004(8) C25 0.0674(11) 0.0725(15) 0.0458(10) 0.0046(10) 0.0296(9) 0.0019(10) C26 0.0801(14) 0.101(2) 0.0450(11) 0.0059(12) 0.0273(10) 0.0005(14) C27 0.0706(13) 0.109(2) 0.0447(11) -0.0164(12) 0.0310(10) -0.0095(13) C28 0.0727(13) 0.0859(17) 0.0581(13) -0.0221(12) 0.0349(11) -0.0028(12) C29 0.0587(9) 0.0464(11) 0.0516(10) 0.0023(8) 0.0369(8) -0.0015(8) C30 0.0848(14) 0.0521(12) 0.0601(12) 0.0078(10) 0.0442(11) 0.0042(10) C31 0.118(2) 0.0490(13) 0.0853(17) 0.0120(12) 0.0696(16) 0.0091(13) C32 0.125(2) 0.0436(12) 0.0976(19) -0.0053(12) 0.0811(18) -0.0058(13) C33 0.0979(16) 0.0541(13) 0.0734(14) -0.0098(11) 0.0565(13) -0.0132(12) _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 C17 1.335(2) . ? N1 C18 1.351(2) . ? N2 C28 1.336(3) . ? N2 C24 1.339(3) . ? N3 C33 1.336(3) . ? N3 C29 1.343(3) . ? C1 C2 1.398(2) . ? C1 C13 1.410(2) . ? C1 C15 1.494(2) . ? C2 C10 1.426(3) . ? C2 C3 1.478(2) . ? C3 C4 1.385(3) . ? C3 C8 1.408(2) . ? C4 C5 1.396(3) . ? C5 C6 1.383(3) . ? C6 C7 1.377(4) . ? C7 C8 1.389(3) . ? C8 C9 1.488(3) . ? C9 C10 1.526(2) . ? C10 C11 1.396(3) . ? C11 C12 1.435(2) . ? C11 C20 1.544(3) . ? C12 C13 1.415(3) . ? C12 C14 1.438(3) . ? C13 C13 1.469(3) 2_756 ? C14 C14 1.345(4) 2_756 ? C15 C19 1.390(3) . ? C15 C16 1.395(2) . ? C16 C17 1.391(3) . ? C17 C24 1.496(2) . ? C18 C19 1.399(3) . ? C18 C29 1.481(3) . ? C20 C22 1.528(4) . ? C20 C21 1.544(4) . ? C20 C23 1.555(4) . ? C24 C25 1.385(3) . ? C25 C26 1.391(3) . ? C26 C27 1.347(4) . ? C27 C28 1.363(4) . ? C29 C30 1.387(3) . ? C30 C31 1.376(3) . ? C31 C32 1.382(4) . ? C32 C33 1.370(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 C17 N1 C18 118.10(15) . . ? C28 N2 C24 117.2(2) . . ? C33 N3 C29 117.01(19) . . ? C2 C1 C13 116.74(15) . . ? C2 C1 C15 122.69(15) . . ? C13 C1 C15 119.75(14) . . ? C1 C2 C10 120.05(16) . . ? C1 C2 C3 130.61(16) . . ? C10 C2 C3 109.31(14) . . ? C4 C3 C8 119.28(17) . . ? C4 C3 C2 133.31(16) . . ? C8 C3 C2 107.30(17) . . ? C3 C4 C5 119.35(19) . . ? C6 C5 C4 120.5(2) . . ? C7 C6 C5 121.0(2) . . ? C6 C7 C8 118.8(2) . . ? C7 C8 C3 121.0(2) . . ? C7 C8 C9 128.03(18) . . ? C3 C8 C9 110.99(16) . . ? C8 C9 C10 103.91(15) . . ? C11 C10 C2 122.21(15) . . ? C11 C10 C9 129.84(17) . . ? C2 C10 C9 107.50(16) . . ? C10 C11 C12 115.44(17) . . ? C10 C11 C20 123.96(17) . . ? C12 C11 C20 120.60(18) . . ? C13 C12 C11 118.97(17) . . ? C13 C12 C14 114.72(16) . . ? C11 C12 C14 125.95(17) . . ? C1 C13 C12 120.97(14) . . ? C1 C13 C13 121.89(12) . 2_756 ? C12 C13 C13 116.93(12) . 2_756 ? C14 C14 C12 122.12(12) 2_756 . ? C19 C15 C16 117.53(16) . . ? C19 C15 C1 122.66(15) . . ? C16 C15 C1 119.81(16) . . ? C17 C16 C15 119.60(17) . . ? N1 C17 C16 122.93(16) . . ? N1 C17 C24 116.83(16) . . ? C16 C17 C24 120.24(17) . . ? N1 C18 C19 122.20(17) . . ? N1 C18 C29 116.43(16) . . ? C19 C18 C29 121.37(16) . . ? C15 C19 C18 119.62(16) . . ? C22 C20 C11 112.5(2) . . ? C22 C20 C21 108.8(2) . . ? C11 C20 C21 109.2(2) . . ? C22 C20 C23 104.1(2) . . ? C11 C20 C23 111.01(17) . . ? C21 C20 C23 111.2(2) . . ? N2 C24 C25 122.00(18) . . ? N2 C24 C17 117.02(17) . . ? C25 C24 C17 120.94(19) . . ? C24 C25 C26 118.3(2) . . ? C27 C26 C25 119.9(2) . . ? C26 C27 C28 118.2(2) . . ? N2 C28 C27 124.4(3) . . ? N3 C29 C30 121.88(19) . . ? N3 C29 C18 116.46(17) . . ? C30 C29 C18 121.65(18) . . ? C31 C30 C29 120.0(2) . . ? C30 C31 C32 118.2(2) . . ? C33 C32 C31 118.3(2) . . ? N3 C33 C32 124.5(2) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.325 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.057 data_bw7ccd _database_code_depnum_ccdc_archive 'CCDC 750096' #TrackingRef 'cmpd2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H40 N2' _chemical_formula_weight 620.80 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 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 17.9360(11) _cell_length_b 10.3982(7) _cell_length_c 20.0030(13) _cell_angle_alpha 90.00 _cell_angle_beta 116.370(1) _cell_angle_gamma 90.00 _cell_volume 3342.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6470 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 27.51 _exptl_crystal_description 'irregular crstyalline fragment' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.969 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4 automated diffractometer' _diffrn_measurement_method 'Smart 1K CCD detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 11121 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0718 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3820 _reflns_number_gt 3052 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART version 5.6' _computing_cell_refinement 'SMART version 5.6' _computing_data_reduction 'SAINT version 5/6.0' _computing_structure_solution 'SHELXTL 6.1' _computing_structure_refinement 'SHELXTL 6.1' _computing_molecular_graphics ? _computing_publication_material 'SHELXTL 6.1' _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^)+(0.0635P)^2^+1.8237P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3820 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0683 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1605 _refine_ls_wR_factor_gt 0.1495 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.16446(13) 0.16880(19) 0.39840(12) 0.0695(5) Uani 1 1 d . . . C1 C 0.00610(11) 0.78913(14) 0.21912(10) 0.0422(4) Uani 1 1 d . . . H1 H 0.0046 0.8671 0.1958 0.051 Uiso 1 1 calc R . . C2 C 0.02139(9) 0.67353(13) 0.18782(9) 0.0344(3) Uani 1 1 d . . . C3 C 0.04584(10) 0.67354(14) 0.12838(9) 0.0369(3) Uani 1 1 d . . . C4 C 0.08749(9) 0.56451(14) 0.12276(9) 0.0364(3) Uani 1 1 d . . . C5 C 0.13119(11) 0.54096(16) 0.07389(10) 0.0467(4) Uani 1 1 d . . . H5A H 0.0912 0.5277 0.0223 0.056 Uiso 1 1 calc R . . H5B H 0.1669 0.6128 0.0765 0.056 Uiso 1 1 calc R . . C6 C 0.18113(10) 0.42207(16) 0.10598(10) 0.0430(4) Uani 1 1 d . . . C7 C 0.23647(12) 0.36343(18) 0.08427(12) 0.0538(5) Uani 1 1 d . . . H7 H 0.2449 0.3968 0.0450 0.065 Uiso 1 1 calc R . . C8 C 0.27863(12) 0.2552(2) 0.12167(12) 0.0588(5) Uani 1 1 d . . . H8 H 0.3149 0.2138 0.1070 0.071 Uiso 1 1 calc R . . C9 C 0.26702(12) 0.2080(2) 0.18104(12) 0.0577(5) Uani 1 1 d . . . H9 H 0.2965 0.1356 0.2064 0.069 Uiso 1 1 calc R . . C10 C 0.21240(11) 0.26645(18) 0.20330(11) 0.0492(4) Uani 1 1 d . . . H10 H 0.2058 0.2343 0.2437 0.059 Uiso 1 1 calc R . . C11 C 0.16730(9) 0.37404(15) 0.16463(9) 0.0380(4) Uani 1 1 d . . . C12 C 0.10512(9) 0.45884(14) 0.17341(8) 0.0332(3) Uani 1 1 d . . . C13 C 0.06972(8) 0.45178(13) 0.22275(8) 0.0306(3) Uani 1 1 d . . . C14 C 0.02172(8) 0.55848(13) 0.22618(8) 0.0302(3) Uani 1 1 d . . . C15 C 0.09697(9) 0.35056(14) 0.28206(9) 0.0339(3) Uani 1 1 d . . . C16 C 0.08908(10) 0.21948(15) 0.26807(11) 0.0448(4) Uani 1 1 d . . . H16 H 0.0609 0.1891 0.2194 0.054 Uiso 1 1 calc R . . C17 C 0.12366(13) 0.13374(18) 0.32749(14) 0.0597(5) Uani 1 1 d . . . H17 H 0.1178 0.0462 0.3168 0.072 Uiso 1 1 calc R . . C18 C 0.17095(14) 0.2953(2) 0.41121(11) 0.0642(6) Uani 1 1 d . . . H18 H 0.1991 0.3229 0.4604 0.077 Uiso 1 1 calc R . . C19 C 0.13869(11) 0.38735(17) 0.35633(9) 0.0460(4) Uani 1 1 d . . . H19 H 0.1448 0.4741 0.3690 0.055 Uiso 1 1 calc R . . C20 C 0.02981(11) 0.79470(16) 0.07810(10) 0.0466(4) Uani 1 1 d . . . C21 C 0.03073(17) 0.7670(2) 0.00274(13) 0.0703(6) Uani 1 1 d . . . H21A H 0.0870 0.7535 0.0106 0.105 Uiso 1 1 calc R . . H21B H 0.0074 0.8389 -0.0301 0.105 Uiso 1 1 calc R . . H21C H -0.0016 0.6914 -0.0192 0.105 Uiso 1 1 calc R . . C22 C 0.09782(14) 0.89559(19) 0.11957(14) 0.0680(6) Uani 1 1 d . . . H22A H 0.1002 0.9121 0.1677 0.102 Uiso 1 1 calc R . . H22B H 0.0849 0.9739 0.0912 0.102 Uiso 1 1 calc R . . H22C H 0.1507 0.8636 0.1256 0.102 Uiso 1 1 calc R . . C23 C -0.05873(13) 0.8482(2) 0.05485(13) 0.0616(5) Uani 1 1 d . . . H23A H -0.0991 0.7832 0.0283 0.092 Uiso 1 1 calc R . . H23B H -0.0677 0.9218 0.0232 0.092 Uiso 1 1 calc R . . H23C H -0.0644 0.8730 0.0986 0.092 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 N1 0.0806(12) 0.0660(11) 0.0713(13) 0.0338(10) 0.0421(11) 0.0302(9) C1 0.0542(9) 0.0271(7) 0.0529(10) 0.0046(6) 0.0305(8) 0.0009(6) C2 0.0371(7) 0.0291(7) 0.0399(8) 0.0029(6) 0.0196(6) 0.0011(5) C3 0.0416(8) 0.0341(7) 0.0381(8) 0.0070(6) 0.0204(7) 0.0009(6) C4 0.0409(8) 0.0371(8) 0.0362(8) 0.0031(6) 0.0217(6) -0.0004(6) C5 0.0581(10) 0.0454(9) 0.0512(10) 0.0068(7) 0.0375(9) 0.0041(7) C6 0.0444(8) 0.0436(9) 0.0488(9) -0.0001(7) 0.0276(7) 0.0001(7) C7 0.0589(11) 0.0565(11) 0.0638(12) -0.0006(9) 0.0432(10) 0.0026(8) C8 0.0559(11) 0.0617(11) 0.0751(13) -0.0025(10) 0.0440(11) 0.0102(9) C9 0.0529(10) 0.0588(11) 0.0694(13) 0.0117(9) 0.0345(10) 0.0204(8) C10 0.0483(9) 0.0553(10) 0.0505(10) 0.0095(8) 0.0277(8) 0.0140(8) C11 0.0363(7) 0.0417(8) 0.0395(8) -0.0024(6) 0.0200(7) 0.0010(6) C12 0.0339(7) 0.0328(7) 0.0337(8) -0.0003(6) 0.0158(6) 0.0009(5) C13 0.0321(7) 0.0282(6) 0.0317(7) 0.0007(5) 0.0143(6) 0.0000(5) C14 0.0324(7) 0.0275(7) 0.0313(7) -0.0006(5) 0.0147(6) -0.0011(5) C15 0.0330(7) 0.0333(7) 0.0399(8) 0.0057(6) 0.0203(6) 0.0044(5) C16 0.0451(9) 0.0334(8) 0.0585(10) 0.0037(7) 0.0253(8) 0.0034(6) C17 0.0614(11) 0.0373(9) 0.0878(16) 0.0201(10) 0.0398(12) 0.0123(8) C18 0.0751(14) 0.0765(14) 0.0428(10) 0.0190(9) 0.0277(10) 0.0318(11) C19 0.0522(9) 0.0470(9) 0.0396(9) 0.0051(7) 0.0212(8) 0.0118(7) C20 0.0579(10) 0.0390(8) 0.0508(10) 0.0143(7) 0.0312(9) 0.0059(7) C21 0.1020(17) 0.0651(13) 0.0604(12) 0.0277(11) 0.0511(13) 0.0253(12) C22 0.0763(14) 0.0470(11) 0.0843(16) 0.0204(10) 0.0389(12) -0.0070(9) C23 0.0666(12) 0.0592(12) 0.0625(12) 0.0243(10) 0.0320(10) 0.0182(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 N1 C17 1.326(3) . ? N1 C18 1.335(3) . ? C1 C1 1.347(3) 2 ? C1 C2 1.437(2) . ? C2 C14 1.4198(19) . ? C2 C3 1.439(2) . ? C3 C4 1.389(2) . ? C3 C20 1.557(2) . ? C4 C12 1.431(2) . ? C4 C5 1.520(2) . ? C5 C6 1.494(2) . ? C6 C7 1.389(2) . ? C6 C11 1.395(2) . ? C7 C8 1.376(3) . ? C8 C9 1.384(3) . ? C9 C10 1.384(2) . ? C10 C11 1.396(2) . ? C11 C12 1.4919(19) . ? C12 C13 1.3926(19) . ? C13 C14 1.4246(18) . ? C13 C15 1.4964(19) . ? C14 C14 1.475(3) 2 ? C15 C16 1.386(2) . ? C15 C19 1.388(2) . ? C16 C17 1.392(3) . ? C18 C19 1.376(3) . ? C20 C22 1.542(3) . ? C20 C21 1.542(3) . ? C20 C23 1.547(3) . ? 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 C17 N1 C18 115.84(17) . . ? C1 C1 C2 122.67(9) 2 . ? C14 C2 C1 115.16(13) . . ? C14 C2 C3 121.14(13) . . ? C1 C2 C3 123.19(13) . . ? C4 C3 C2 116.04(13) . . ? C4 C3 C20 124.03(14) . . ? C2 C3 C20 119.82(13) . . ? C3 C4 C12 121.79(13) . . ? C3 C4 C5 129.25(13) . . ? C12 C4 C5 108.45(13) . . ? C6 C5 C4 103.82(13) . . ? C7 C6 C11 121.64(16) . . ? C7 C6 C5 127.18(16) . . ? C11 C6 C5 111.17(13) . . ? C8 C7 C6 119.05(17) . . ? C7 C8 C9 120.05(16) . . ? C8 C9 C10 121.21(18) . . ? C9 C10 C11 119.51(17) . . ? C6 C11 C10 118.51(14) . . ? C6 C11 C12 107.99(13) . . ? C10 C11 C12 133.47(14) . . ? C13 C12 C4 121.00(13) . . ? C13 C12 C11 130.71(13) . . ? C4 C12 C11 108.18(12) . . ? C12 C13 C14 117.95(12) . . ? C12 C13 C15 120.51(12) . . ? C14 C13 C15 120.07(12) . . ? C2 C14 C13 119.18(12) . . ? C2 C14 C14 118.21(9) . 2 ? C13 C14 C14 122.36(9) . 2 ? C16 C15 C19 116.45(15) . . ? C16 C15 C13 124.30(15) . . ? C19 C15 C13 119.07(14) . . ? C15 C16 C17 119.38(18) . . ? N1 C17 C16 124.21(18) . . ? N1 C18 C19 124.2(2) . . ? C18 C19 C15 119.88(18) . . ? C22 C20 C21 107.67(17) . . ? C22 C20 C23 112.21(16) . . ? C21 C20 C23 103.22(17) . . ? C22 C20 C3 109.15(15) . . ? C21 C20 C3 113.67(15) . . ? C23 C20 C3 110.84(14) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.260 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.044