# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _audit_creation_method SHELXL-97 _publ_contact_author_name 'Jeffrey L. Katz' _publ_contact_author_email jlkatz@colby.edu _publ_contact_author_address ; Colby College Department of Chemistry 5754 Mayflower Hill Drive Waterville, ME 04901-8857 USA ; _publ_section_title ; Oxacalixarenes and Oxacyclophanes Containing 1,8-Naphthyridines: A New Class of Molecular Tweezers With Concave-Surface Functionality ; loop_ _publ_author_name 'Jeffrey L. Katz' 'Bram J. Geller' 'Peter D. Foster' data_624760 _database_code_depnum_ccdc_archive 'CCDC 624760' _chemical_name_systematic ; ? ; _chemical_name_common 'compound 3' _chemical_melting_point >533K _chemical_formula_moiety 'C32 H22 Cl4 N4 O4' _chemical_formula_sum 'C32 H22 Cl4 N4 O4' _chemical_formula_weight 668.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnnm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x, y, -z' 'x-1/2, -y-1/2, z-1/2' '-x-1/2, y-1/2, z-1/2' _cell_length_a 10.6659(9) _cell_length_b 16.1506(14) _cell_length_c 18.2407(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3142.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 174(2) _cell_measurement_reflns_used 9555 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.2 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.420 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 174(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_reflns_number 26939 _diffrn_reflns_av_R_equivalents 0.0973 _diffrn_reflns_av_sigmaI/netI 0.0451 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 28.27 _reflns_number_total 3942 _reflns_number_gt 3175 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0957P)^2^+1.0503P] 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 3942 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1685 _refine_ls_wR_factor_gt 0.1586 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.96233(16) 0.37881(10) 0.12421(9) 0.0330(4) Uani 1 1 d . . . C2 C 1.08552(17) 0.40979(13) 0.13118(11) 0.0398(4) Uani 1 1 d . . . H2 H 1.1218 0.4201 0.1779 0.048 Uiso 1 1 calc R . . C3 C 1.0926(2) 0.40849(16) 0.0000 0.0357(5) Uani 1 2 d S . . C4 C 1.14970(18) 0.42422(13) -0.06852(11) 0.0419(5) Uani 1 1 d . . . H4 H 1.2330 0.4449 -0.0706 0.050 Uiso 1 1 calc R . . C5 C 0.78317(17) 0.32848(12) 0.18630(9) 0.0346(4) Uani 1 1 d . . . C6 C 0.67481(18) 0.37461(12) 0.18982(10) 0.0369(4) Uani 1 1 d . . . H6 H 0.6792 0.4333 0.1918 0.044 Uiso 1 1 calc R . . C7 C 0.55906(18) 0.33522(12) 0.19043(10) 0.0398(4) Uani 1 1 d . . . C8 C 0.55500(18) 0.24881(12) 0.18908(10) 0.0379(4) Uani 1 1 d . . . H8 H 0.4768 0.2207 0.1902 0.045 Uiso 1 1 calc R . . C9 C 0.66602(18) 0.20463(11) 0.18608(9) 0.0348(4) Uani 1 1 d . . . C10 C 0.65538(18) -0.05682(11) -0.06868(11) 0.0413(5) Uani 1 1 d . . . H10 H 0.6527 -0.1156 -0.0708 0.050 Uiso 1 1 calc R . . C11 C 0.6581(2) -0.01626(15) 0.0000 0.0360(5) Uani 1 2 d S . . C12 C 0.65662(18) -0.01197(11) 0.13151(11) 0.0407(4) Uani 1 1 d . . . H12 H 0.6537 -0.0379 0.1782 0.049 Uiso 1 1 calc R . . C13 C 0.66244(16) 0.07542(11) 0.12439(10) 0.0344(4) Uani 1 1 d . . . C14 C 0.9692(2) 0.37658(14) 0.0000 0.0304(5) Uani 1 2 d S . . C15 C 0.78130(17) 0.24278(11) 0.18403(9) 0.0355(4) Uani 1 1 d . . . H15 H 0.8566 0.2116 0.1812 0.043 Uiso 1 1 calc R . . C16 C 0.6640(2) 0.07156(14) 0.0000 0.0315(5) Uani 1 2 d S . . C17 C 0.4397(2) 0.38551(15) 0.18992(14) 0.0542(6) Uani 1 1 d . . . H17A H 0.4316 0.4154 0.2364 0.081 Uiso 1 1 calc R . . H17B H 0.3677 0.3485 0.1836 0.081 Uiso 1 1 calc R . . H17C H 0.4423 0.4253 0.1494 0.081 Uiso 1 1 calc R . . N1 N 0.90501(13) 0.36101(9) 0.06309(7) 0.0310(3) Uani 1 1 d . . . N2 N 0.66655(14) 0.11656(9) 0.06318(8) 0.0331(3) Uani 1 1 d . . . O1 O 0.89960(12) 0.36886(9) 0.18904(7) 0.0391(3) Uani 1 1 d . . . O2 O 0.66131(14) 0.11762(8) 0.18919(7) 0.0416(3) Uani 1 1 d . . . C18 C 0.5986(3) 0.31131(16) 0.0000 0.0400(6) Uani 1 2 d S . . H18A H 0.6433 0.2908 0.0440 0.048 Uiso 0.50 1 calc PR . . H18B H 0.6433 0.2908 -0.0440 0.048 Uiso 0.50 1 calc PR . . Cl1 Cl 0.59697(7) 0.42042(4) 0.0000 0.0474(2) Uani 1 2 d S . . Cl2 Cl 0.44252(8) 0.27385(5) 0.0000 0.0572(2) Uani 1 2 d S . . C19 C -0.0314(5) 0.1549(3) 0.0000 0.1066(19) Uani 1 2 d S . . Cl3 Cl 0.0646(2) 0.1686(2) 0.07605(15) 0.1547(13) Uani 0.659(4) 1 d P . . Cl4 Cl -0.0060(5) 0.0832(4) 0.0724(3) 0.163(3) Uani 0.341(4) 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 C1 0.0324(9) 0.0348(8) 0.0318(9) 0.0021(7) -0.0011(6) -0.0018(7) C2 0.0334(9) 0.0489(10) 0.0371(10) -0.0003(8) -0.0095(7) -0.0048(7) C3 0.0268(11) 0.0398(12) 0.0406(14) 0.000 0.000 -0.0015(9) C4 0.0268(9) 0.0520(11) 0.0468(11) -0.0008(8) 0.0067(7) -0.0069(8) C5 0.0354(9) 0.0447(9) 0.0237(8) 0.0013(7) -0.0003(6) -0.0052(7) C6 0.0434(10) 0.0367(9) 0.0306(9) 0.0013(7) 0.0042(7) -0.0004(7) C7 0.0389(10) 0.0456(10) 0.0348(9) 0.0054(8) 0.0080(7) 0.0038(8) C8 0.0356(9) 0.0452(10) 0.0330(9) 0.0054(8) 0.0059(7) -0.0055(7) C9 0.0448(10) 0.0349(9) 0.0248(8) 0.0036(6) 0.0027(7) -0.0012(7) C10 0.0405(10) 0.0281(8) 0.0554(12) -0.0059(8) 0.0004(8) 0.0020(7) C11 0.0304(12) 0.0311(12) 0.0466(15) 0.000 0.000 0.0023(9) C12 0.0412(10) 0.0357(9) 0.0451(11) 0.0117(8) 0.0003(8) 0.0021(7) C13 0.0311(9) 0.0360(9) 0.0360(9) 0.0034(7) 0.0013(7) 0.0012(7) C14 0.0255(11) 0.0313(11) 0.0345(12) 0.000 0.000 -0.0014(9) C15 0.0360(9) 0.0440(9) 0.0265(8) 0.0020(7) 0.0003(7) 0.0035(7) C16 0.0277(11) 0.0298(11) 0.0370(13) 0.000 0.000 0.0011(9) C17 0.0414(11) 0.0545(12) 0.0666(15) 0.0134(11) 0.0130(10) 0.0084(10) N1 0.0271(7) 0.0357(7) 0.0302(8) -0.0001(6) -0.0007(5) -0.0019(6) N2 0.0346(8) 0.0294(7) 0.0352(8) 0.0018(6) 0.0005(6) -0.0002(6) O1 0.0371(7) 0.0509(8) 0.0292(6) -0.0003(5) -0.0034(5) -0.0087(6) O2 0.0557(8) 0.0365(7) 0.0326(7) 0.0061(5) 0.0032(6) -0.0024(6) C18 0.0454(15) 0.0325(12) 0.0421(14) 0.000 0.000 0.0028(11) Cl1 0.0530(4) 0.0352(3) 0.0539(4) 0.000 0.000 -0.0002(3) Cl2 0.0536(5) 0.0503(4) 0.0678(5) 0.000 0.000 -0.0113(3) C19 0.060(3) 0.080(3) 0.180(6) 0.000 0.000 0.013(2) Cl3 0.0900(13) 0.162(3) 0.212(2) -0.0352(17) -0.0246(13) 0.0728(16) Cl4 0.104(3) 0.198(6) 0.186(4) 0.033(4) 0.025(3) 0.082(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.304(2) . ? C1 O1 1.368(2) . ? C1 C2 1.412(2) . ? C2 C4 1.353(3) 6 ? C3 C4 1.413(2) 6 ? C3 C4 1.413(2) . ? C3 C14 1.414(3) . ? C4 C2 1.353(3) 6 ? C5 C6 1.376(3) . ? C5 C15 1.385(3) . ? C5 O1 1.404(2) . ? C6 C7 1.389(3) . ? C7 C8 1.396(3) . ? C7 C17 1.510(3) . ? C8 C9 1.384(3) . ? C9 C15 1.376(3) . ? C9 O2 1.407(2) . ? C10 C12 1.356(3) 6 ? C10 C11 1.414(2) . ? C11 C10 1.414(2) 6 ? C11 C16 1.420(3) . ? C12 C10 1.356(3) 6 ? C12 C13 1.419(2) . ? C13 N2 1.300(2) . ? C13 O2 1.364(2) . ? C14 N1 1.3625(18) 6 ? C14 N1 1.3625(18) . ? C16 N2 1.3627(19) . ? C16 N2 1.3627(19) 6 ? C18 Cl1 1.762(3) . ? C18 Cl2 1.771(3) . ? C19 Cl3 1.738(4) . ? C19 Cl3 1.738(4) 6 ? C19 Cl4 1.776(6) 6 ? C19 Cl4 1.776(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 O1 118.95(15) . . ? N1 C1 C2 126.27(16) . . ? O1 C1 C2 114.77(15) . . ? C4 C2 C1 117.14(17) 6 . ? C4 C3 C4 124.3(2) 6 . ? C4 C3 C14 117.82(12) 6 . ? C4 C3 C14 117.82(12) . . ? C2 C4 C3 119.89(17) 6 . ? C6 C5 C15 122.02(17) . . ? C6 C5 O1 119.33(16) . . ? C15 C5 O1 118.57(17) . . ? C5 C6 C7 119.92(17) . . ? C6 C7 C8 119.03(18) . . ? C6 C7 C17 120.20(18) . . ? C8 C7 C17 120.74(18) . . ? C9 C8 C7 119.31(17) . . ? C15 C9 C8 122.34(17) . . ? C15 C9 O2 118.70(16) . . ? C8 C9 O2 118.87(16) . . ? C12 C10 C11 120.07(17) 6 . ? C10 C11 C10 124.7(2) 6 . ? C10 C11 C16 117.63(12) 6 . ? C10 C11 C16 117.63(12) . . ? C10 C12 C13 117.04(17) 6 . ? N2 C13 O2 119.27(15) . . ? N2 C13 C12 126.06(17) . . ? O2 C13 C12 114.66(16) . . ? N1 C14 N1 115.3(2) 6 . ? N1 C14 C3 122.36(10) 6 . ? N1 C14 C3 122.36(10) . . ? C9 C15 C5 117.36(17) . . ? N2 C16 N2 115.5(2) . 6 ? N2 C16 C11 122.26(10) . . ? N2 C16 C11 122.26(10) 6 . ? C1 N1 C14 116.49(15) . . ? C13 N2 C16 116.94(15) . . ? C1 O1 C5 117.16(13) . . ? C13 O2 C9 117.62(14) . . ? Cl1 C18 Cl2 109.42(15) . . ? Cl3 C19 Cl3 105.9(3) . 6 ? Cl4 C19 Cl4 96.0(5) 6 . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.748 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.073 #===END data_624761 _database_code_depnum_ccdc_archive 'CCDC 624761' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'compound 6' _chemical_melting_point >533K _chemical_formula_moiety 'C36.50 H20 Cl N4 O5' _chemical_formula_sum 'C36.50 H20 Cl N4 O5' _chemical_formula_weight 630.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6887(8) _cell_length_b 13.1957(10) _cell_length_c 13.4844(10) _cell_angle_alpha 100.3880(10) _cell_angle_beta 107.1250(10) _cell_angle_gamma 111.1100(10) _cell_volume 1455.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5256 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 28.07 _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.186 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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_reflns_number 13087 _diffrn_reflns_av_R_equivalents 0.0512 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 28.29 _reflns_number_total 6628 _reflns_number_gt 4971 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0802P)^2^+0.1740P] 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 6628 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0661 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1533 _refine_ls_wR_factor_gt 0.1457 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 1.2753(2) 0.50790(15) 0.20934(14) 0.0357(4) Uani 1 1 d . . . C2 C 1.3431(2) 0.51235(16) 0.12950(15) 0.0392(4) Uani 1 1 d . . . H2 H 1.4554 0.5544 0.1496 0.047 Uiso 1 1 calc R . . C3 C 1.2418(2) 0.45443(16) 0.02346(15) 0.0395(4) Uani 1 1 d . . . H3 H 1.2828 0.4552 -0.0325 0.047 Uiso 1 1 calc R . . C4 C 1.0747(2) 0.39265(14) -0.00426(14) 0.0337(4) Uani 1 1 d . . . C5 C 0.9567(2) 0.33516(15) -0.11178(14) 0.0385(4) Uani 1 1 d . . . H5 H 0.9874 0.3333 -0.1726 0.046 Uiso 1 1 calc R . . C6 C 0.7987(2) 0.28227(15) -0.12845(14) 0.0372(4) Uani 1 1 d . . . H6 H 0.7170 0.2431 -0.2002 0.045 Uiso 1 1 calc R . . C7 C 0.7613(2) 0.28808(14) -0.03467(13) 0.0336(4) Uani 1 1 d . . . C8 C 0.55707(19) 0.21637(15) 0.03211(13) 0.0340(4) Uani 1 1 d . . . C9 C 0.4705(2) 0.26986(16) 0.06546(15) 0.0417(4) Uani 1 1 d . . . H9 H 0.4480 0.3231 0.0327 0.050 Uiso 1 1 calc R . . C10 C 0.4182(2) 0.24516(18) 0.14565(16) 0.0456(5) Uani 1 1 d . . . H10 H 0.3592 0.2817 0.1685 0.055 Uiso 1 1 calc R . . C11 C 0.4505(2) 0.16575(15) 0.19551(14) 0.0357(4) Uani 1 1 d . . . C12 C 0.3988(2) 0.13727(18) 0.27894(16) 0.0461(5) Uani 1 1 d . . . H12 H 0.3396 0.1725 0.3036 0.055 Uiso 1 1 calc R . . C13 C 0.4320(2) 0.06059(17) 0.32432(15) 0.0428(4) Uani 1 1 d . . . H13 H 0.3968 0.0425 0.3803 0.051 Uiso 1 1 calc R . . C14 C 0.51873(19) 0.00841(14) 0.28789(13) 0.0325(4) Uani 1 1 d . . . C15 C 0.67449(19) -0.04290(14) 0.42331(13) 0.0308(3) Uani 1 1 d . . . C16 C 0.6948(2) -0.13372(14) 0.45787(14) 0.0342(4) Uani 1 1 d . . . H16 H 0.6207 -0.2116 0.4180 0.041 Uiso 1 1 calc R . . C17 C 0.8247(2) -0.10484(14) 0.55029(14) 0.0341(4) Uani 1 1 d . . . H17 H 0.8435 -0.1630 0.5761 0.041 Uiso 1 1 calc R . . C18 C 0.93185(19) 0.01182(14) 0.60795(13) 0.0314(3) Uani 1 1 d . . . C19 C 1.0700(2) 0.05210(16) 0.70544(14) 0.0379(4) Uani 1 1 d . . . H19 H 1.0937 -0.0008 0.7382 0.045 Uiso 1 1 calc R . . C20 C 1.1685(2) 0.16578(16) 0.75214(14) 0.0381(4) Uani 1 1 d . . . H20 H 1.2617 0.1944 0.8176 0.046 Uiso 1 1 calc R . . C21 C 1.12685(19) 0.24041(14) 0.69945(13) 0.0317(4) Uani 1 1 d . . . C22 C 1.21976(19) 0.42729(14) 0.68343(13) 0.0334(4) Uani 1 1 d . . . C23 C 1.1704(2) 0.51034(16) 0.71550(15) 0.0403(4) Uani 1 1 d . . . H23 H 1.1375 0.5137 0.7753 0.048 Uiso 1 1 calc R . . C24 C 1.1703(2) 0.58686(16) 0.65935(16) 0.0440(4) Uani 1 1 d . . . H24 H 1.1370 0.6437 0.6808 0.053 Uiso 1 1 calc R . . C25 C 1.2185(2) 0.58337(14) 0.57025(14) 0.0358(4) Uani 1 1 d . . . C26 C 1.2215(2) 0.66271(16) 0.51158(16) 0.0450(4) Uani 1 1 d . . . H26 H 1.1888 0.7204 0.5318 0.054 Uiso 1 1 calc R . . C27 C 1.2705(2) 0.65737(16) 0.42649(16) 0.0445(4) Uani 1 1 d . . . H27 H 1.2723 0.7110 0.3878 0.053 Uiso 1 1 calc R . . C28 C 1.31784(19) 0.57223(16) 0.39690(14) 0.0378(4) Uani 1 1 d . . . C29 C 1.02188(19) 0.39210(14) 0.08288(13) 0.0317(4) Uani 1 1 d . . . C30 C 0.59102(19) 0.13916(15) 0.07686(13) 0.0337(4) Uani 1 1 d . . . H30 H 0.6497 0.1036 0.0520 0.040 Uiso 1 1 calc R . . C31 C 0.53909(18) 0.11208(14) 0.15999(13) 0.0308(3) Uani 1 1 d . . . C32 C 0.57104(19) 0.03218(14) 0.20821(13) 0.0334(4) Uani 1 1 d . . . H32 H 0.6291 -0.0049 0.1848 0.040 Uiso 1 1 calc R . . C33 C 0.90044(18) 0.09501(14) 0.56464(13) 0.0286(3) Uani 1 1 d . . . C34 C 1.2674(2) 0.41997(14) 0.59824(13) 0.0343(4) Uani 1 1 d . . . H34 H 1.3012 0.3627 0.5789 0.041 Uiso 1 1 calc R . . C35 C 1.26681(18) 0.49722(14) 0.53847(13) 0.0316(4) Uani 1 1 d . . . C36 C 1.3164(2) 0.49356(15) 0.44958(14) 0.0370(4) Uani 1 1 d . . . H36 H 1.3485 0.4363 0.4269 0.044 Uiso 1 1 calc R . . N1 N 1.12425(16) 0.44939(13) 0.18982(11) 0.0350(3) Uani 1 1 d . . . N2 N 0.86425(16) 0.33784(12) 0.06626(11) 0.0335(3) Uani 1 1 d . . . N3 N 0.76973(16) 0.06611(11) 0.47194(11) 0.0309(3) Uani 1 1 d . . . N4 N 0.99945(15) 0.20916(12) 0.61148(11) 0.0308(3) Uani 1 1 d . . . O1 O 1.37969(14) 0.57317(12) 0.31418(10) 0.0449(3) Uani 1 1 d . . . O2 O 0.60026(14) 0.23883(11) -0.05499(9) 0.0398(3) Uani 1 1 d . . . O3 O 0.54215(14) -0.07687(10) 0.32998(9) 0.0375(3) Uani 1 1 d . . . O4 O 1.23074(14) 0.35425(10) 0.74746(9) 0.0384(3) Uani 1 1 d . . . C37 C 0.0169(10) 1.0105(8) -0.0376(6) 0.115(3) Uani 0.50 1 d P . . Cl1 Cl -0.0496(3) 1.08734(16) -0.0294(2) 0.1141(7) Uani 0.50 1 d P . . Cl2 Cl -0.0424(4) 1.0900(3) 0.0593(3) 0.1496(10) Uani 0.50 1 d P . . O5 O 0.0262(4) 0.2253(3) 0.2558(3) 0.1608(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0349(9) 0.0371(9) 0.0362(9) 0.0174(8) 0.0134(7) 0.0147(7) C2 0.0331(8) 0.0444(10) 0.0479(10) 0.0232(8) 0.0204(8) 0.0175(8) C3 0.0435(10) 0.0446(10) 0.0443(10) 0.0218(8) 0.0268(8) 0.0229(8) C4 0.0414(9) 0.0328(9) 0.0354(9) 0.0152(7) 0.0209(7) 0.0187(7) C5 0.0508(10) 0.0382(9) 0.0335(9) 0.0145(7) 0.0228(8) 0.0206(8) C6 0.0453(10) 0.0336(9) 0.0263(8) 0.0093(7) 0.0119(7) 0.0126(8) C7 0.0370(9) 0.0292(8) 0.0326(9) 0.0132(7) 0.0140(7) 0.0107(7) C8 0.0288(8) 0.0358(9) 0.0258(8) 0.0091(7) 0.0063(6) 0.0057(7) C9 0.0451(10) 0.0419(10) 0.0422(10) 0.0218(8) 0.0147(8) 0.0216(9) C10 0.0511(11) 0.0513(12) 0.0518(11) 0.0242(9) 0.0251(9) 0.0331(10) C11 0.0343(8) 0.0391(9) 0.0360(9) 0.0145(7) 0.0146(7) 0.0167(7) C12 0.0541(11) 0.0582(12) 0.0497(11) 0.0266(10) 0.0324(9) 0.0355(10) C13 0.0486(10) 0.0514(11) 0.0395(10) 0.0222(9) 0.0247(8) 0.0240(9) C14 0.0293(8) 0.0303(8) 0.0289(8) 0.0099(7) 0.0049(6) 0.0084(7) C15 0.0330(8) 0.0321(8) 0.0302(8) 0.0125(7) 0.0148(7) 0.0142(7) C16 0.0399(9) 0.0282(8) 0.0382(9) 0.0129(7) 0.0193(7) 0.0146(7) C17 0.0411(9) 0.0339(9) 0.0391(9) 0.0197(7) 0.0214(7) 0.0206(7) C18 0.0365(8) 0.0364(9) 0.0321(8) 0.0178(7) 0.0178(7) 0.0208(7) C19 0.0423(9) 0.0446(10) 0.0368(9) 0.0231(8) 0.0166(7) 0.0241(8) C20 0.0376(9) 0.0466(10) 0.0295(9) 0.0166(8) 0.0087(7) 0.0196(8) C21 0.0338(8) 0.0340(9) 0.0277(8) 0.0098(7) 0.0137(7) 0.0141(7) C22 0.0304(8) 0.0299(8) 0.0290(8) 0.0070(7) 0.0049(6) 0.0083(7) C23 0.0428(9) 0.0378(10) 0.0362(9) 0.0063(8) 0.0170(8) 0.0150(8) C24 0.0505(11) 0.0357(10) 0.0485(11) 0.0082(8) 0.0210(9) 0.0231(9) C25 0.0343(8) 0.0283(8) 0.0360(9) 0.0063(7) 0.0075(7) 0.0115(7) C26 0.0494(11) 0.0341(10) 0.0508(11) 0.0144(8) 0.0158(9) 0.0205(9) C27 0.0441(10) 0.0378(10) 0.0456(11) 0.0194(8) 0.0104(8) 0.0145(8) C28 0.0286(8) 0.0413(10) 0.0305(9) 0.0105(7) 0.0054(7) 0.0070(7) C29 0.0366(8) 0.0309(8) 0.0315(8) 0.0143(7) 0.0157(7) 0.0151(7) C30 0.0312(8) 0.0348(9) 0.0312(8) 0.0087(7) 0.0114(7) 0.0118(7) C31 0.0261(7) 0.0309(8) 0.0287(8) 0.0078(7) 0.0075(6) 0.0089(7) C32 0.0304(8) 0.0344(9) 0.0333(9) 0.0100(7) 0.0102(7) 0.0143(7) C33 0.0308(8) 0.0306(8) 0.0294(8) 0.0123(6) 0.0145(6) 0.0154(7) C34 0.0359(8) 0.0311(8) 0.0332(9) 0.0070(7) 0.0099(7) 0.0166(7) C35 0.0277(8) 0.0284(8) 0.0299(8) 0.0056(7) 0.0051(6) 0.0097(6) C36 0.0360(9) 0.0366(9) 0.0345(9) 0.0085(7) 0.0105(7) 0.0159(7) N1 0.0332(7) 0.0382(8) 0.0311(7) 0.0141(6) 0.0125(6) 0.0119(6) N2 0.0347(7) 0.0343(8) 0.0277(7) 0.0115(6) 0.0130(6) 0.0101(6) N3 0.0326(7) 0.0292(7) 0.0302(7) 0.0109(6) 0.0104(6) 0.0138(6) N4 0.0320(7) 0.0309(7) 0.0293(7) 0.0101(6) 0.0105(6) 0.0147(6) O1 0.0321(6) 0.0545(8) 0.0362(7) 0.0166(6) 0.0106(5) 0.0078(6) O2 0.0356(6) 0.0436(7) 0.0301(6) 0.0149(5) 0.0100(5) 0.0075(5) O3 0.0389(6) 0.0297(6) 0.0340(6) 0.0117(5) 0.0068(5) 0.0100(5) O4 0.0391(6) 0.0363(7) 0.0294(6) 0.0102(5) 0.0066(5) 0.0112(5) C37 0.108(5) 0.121(6) 0.089(6) 0.025(5) 0.033(5) 0.031(5) Cl1 0.1299(16) 0.0726(11) 0.1216(16) 0.0296(11) 0.0184(13) 0.0505(11) Cl2 0.168(2) 0.187(3) 0.211(3) 0.122(2) 0.124(2) 0.135(2) O5 0.165(3) 0.107(2) 0.204(3) 0.087(2) 0.040(3) 0.062(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.301(2) . ? C1 O1 1.362(2) . ? C1 C2 1.416(2) . ? C2 C3 1.353(3) . ? C3 C4 1.417(2) . ? C4 C5 1.410(2) . ? C4 C29 1.413(2) . ? C5 C6 1.361(3) . ? C6 C7 1.411(2) . ? C7 N2 1.298(2) . ? C7 O2 1.374(2) . ? C8 C30 1.363(2) . ? C8 C9 1.392(3) . ? C8 O2 1.4029(19) . ? C9 C10 1.365(3) . ? C10 C11 1.419(2) . ? C11 C12 1.417(2) . ? C11 C31 1.423(2) . ? C12 C13 1.358(3) . ? C13 C14 1.400(3) . ? C14 C32 1.355(2) . ? C14 O3 1.4066(19) . ? C15 N3 1.303(2) . ? C15 O3 1.3641(19) . ? C15 C16 1.418(2) . ? C16 C17 1.357(2) . ? C17 C18 1.412(2) . ? C18 C19 1.415(2) . ? C18 C33 1.416(2) . ? C19 C20 1.353(3) . ? C20 C21 1.416(2) . ? C21 N4 1.302(2) . ? C21 O4 1.366(2) . ? C22 C34 1.359(2) . ? C22 C23 1.395(3) . ? C22 O4 1.416(2) . ? C23 C24 1.367(3) . ? C24 C25 1.411(3) . ? C25 C26 1.419(2) . ? C25 C35 1.421(2) . ? C26 C27 1.365(3) . ? C27 C28 1.396(3) . ? C28 C36 1.358(2) . ? C28 O1 1.413(2) . ? C29 N2 1.359(2) . ? C29 N1 1.363(2) . ? C30 C31 1.409(2) . ? C31 C32 1.412(2) . ? C33 N4 1.359(2) . ? C33 N3 1.3636(19) . ? C34 C35 1.409(2) . ? C35 C36 1.416(2) . ? C37 Cl1 1.768(10) 2_575 ? C37 Cl2 1.877(10) . ? Cl1 C37 1.768(10) 2_575 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 O1 118.91(15) . . ? N1 C1 C2 125.49(16) . . ? O1 C1 C2 115.59(15) . . ? C3 C2 C1 117.48(16) . . ? C2 C3 C4 120.06(16) . . ? C5 C4 C29 117.48(15) . . ? C5 C4 C3 125.23(16) . . ? C29 C4 C3 117.25(16) . . ? C6 C5 C4 119.95(16) . . ? C5 C6 C7 117.13(16) . . ? N2 C7 O2 118.67(15) . . ? N2 C7 C6 125.92(16) . . ? O2 C7 C6 115.38(14) . . ? C30 C8 C9 121.95(16) . . ? C30 C8 O2 120.25(15) . . ? C9 C8 O2 117.68(15) . . ? C10 C9 C8 119.46(16) . . ? C9 C10 C11 121.07(17) . . ? C12 C11 C10 123.17(16) . . ? C12 C11 C31 118.39(16) . . ? C10 C11 C31 118.45(15) . . ? C13 C12 C11 121.25(17) . . ? C12 C13 C14 119.46(16) . . ? C32 C14 C13 121.87(16) . . ? C32 C14 O3 119.24(15) . . ? C13 C14 O3 118.74(15) . . ? N3 C15 O3 119.35(14) . . ? N3 C15 C16 125.93(15) . . ? O3 C15 C16 114.73(14) . . ? C17 C16 C15 117.24(15) . . ? C16 C17 C18 119.84(15) . . ? C17 C18 C19 124.85(15) . . ? C17 C18 C33 117.86(14) . . ? C19 C18 C33 117.29(15) . . ? C20 C19 C18 120.20(15) . . ? C19 C20 C21 117.30(15) . . ? N4 C21 O4 118.77(14) . . ? N4 C21 C20 125.50(16) . . ? O4 C21 C20 115.72(14) . . ? C34 C22 C23 122.14(17) . . ? C34 C22 O4 119.64(15) . . ? C23 C22 O4 118.06(16) . . ? C24 C23 C22 118.80(17) . . ? C23 C24 C25 121.55(17) . . ? C24 C25 C26 122.63(17) . . ? C24 C25 C35 118.58(16) . . ? C26 C25 C35 118.78(17) . . ? C27 C26 C25 120.96(18) . . ? C26 C27 C28 119.28(18) . . ? C36 C28 C27 122.34(17) . . ? C36 C28 O1 118.98(17) . . ? C27 C28 O1 118.54(17) . . ? N2 C29 N1 114.78(14) . . ? N2 C29 C4 122.55(15) . . ? N1 C29 C4 122.63(15) . . ? C8 C30 C31 119.95(16) . . ? C30 C31 C32 121.79(15) . . ? C30 C31 C11 119.12(15) . . ? C32 C31 C11 119.09(15) . . ? C14 C32 C31 119.94(16) . . ? N4 C33 N3 115.18(13) . . ? N4 C33 C18 122.48(14) . . ? N3 C33 C18 122.33(14) . . ? C22 C34 C35 120.06(16) . . ? C34 C35 C36 122.16(15) . . ? C34 C35 C25 118.85(16) . . ? C36 C35 C25 118.97(16) . . ? C28 C36 C35 119.68(17) . . ? C1 N1 C29 117.00(15) . . ? C7 N2 C29 116.94(14) . . ? C15 N3 C33 116.78(14) . . ? C21 N4 C33 117.18(14) . . ? C1 O1 C28 117.81(13) . . ? C7 O2 C8 117.46(12) . . ? C15 O3 C14 117.80(12) . . ? C21 O4 C22 117.32(12) . . ? Cl1 C37 Cl1 137.3(5) . 2_575 ? Cl2 C37 Cl2 140.2(5) 2_575 . ? _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.917 _refine_diff_density_max 0.751 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.049 #===END data_624762 _database_code_depnum_ccdc_archive 'CCDC 624762' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'compound 7' _chemical_melting_point >533K _chemical_formula_moiety 'C40 H26 N6 O4' _chemical_formula_sum 'C40 H26 N6 O4' _chemical_formula_weight 654.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 19.4444(15) _cell_length_b 9.3321(7) _cell_length_c 20.5331(16) _cell_angle_alpha 90.00 _cell_angle_beta 118.0490(10) _cell_angle_gamma 90.00 _cell_volume 3288.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 178(2) _cell_measurement_reflns_used 5830 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.1 _exptl_crystal_description hexagonal _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 178(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_reflns_number 28816 _diffrn_reflns_av_R_equivalents 0.0685 _diffrn_reflns_av_sigmaI/netI 0.0585 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 28.30 _reflns_number_total 7790 _reflns_number_gt 4507 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0869P)^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 7790 _refine_ls_number_parameters 453 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0957 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1564 _refine_ls_wR_factor_gt 0.1343 _refine_ls_goodness_of_fit_ref 0.924 _refine_ls_restrained_S_all 0.924 _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 0.79539(13) -0.0034(2) 0.36089(10) 0.0576(5) Uani 1 1 d . . . C2 C 0.75117(16) -0.0762(3) 0.29362(11) 0.0732(7) Uani 1 1 d . . . H2 H 0.7511 -0.0458 0.2494 0.088 Uiso 1 1 calc R . . C3 C 0.70921(15) -0.1897(2) 0.29430(11) 0.0738(7) Uani 1 1 d . . . H3 H 0.6791 -0.2417 0.2501 0.089 Uiso 1 1 calc R . . C4 C 0.70968(12) -0.2324(2) 0.36085(10) 0.0545(5) Uani 1 1 d . . . C5 C 0.66408(12) -0.3437(2) 0.36724(12) 0.0635(6) Uani 1 1 d . . . H5 H 0.6295 -0.3966 0.3249 0.076 Uiso 1 1 calc R . . C6 C 0.66996(11) -0.3741(2) 0.43360(12) 0.0604(6) Uani 1 1 d . . . H6 H 0.6399 -0.4485 0.4393 0.073 Uiso 1 1 calc R . . C7 C 0.72200(11) -0.29249(19) 0.49419(10) 0.0481(4) Uani 1 1 d . . . C8 C 0.75292(11) -0.22207(18) 0.61565(10) 0.0466(4) Uani 1 1 d . . . C9 C 0.82514(11) -0.23144(19) 0.67405(11) 0.0485(5) Uani 1 1 d . . . H9 H 0.8595 -0.3053 0.6756 0.058 Uiso 1 1 calc R . . C10 C 0.84953(11) -0.13294(19) 0.73218(10) 0.0453(4) Uani 1 1 d . . . C11 C 0.92494(12) -0.1362(3) 0.79444(12) 0.0644(6) Uani 1 1 d . . . H11 H 0.9609 -0.2089 0.7982 0.077 Uiso 1 1 calc R . . C12 C 0.94599(14) -0.0358(3) 0.84872(12) 0.0808(7) Uani 1 1 d . . . H12 H 0.9963 -0.0402 0.8904 0.097 Uiso 1 1 calc R . . C13 C 0.89478(14) 0.0732(3) 0.84401(13) 0.0794(7) Uani 1 1 d . . . H13 H 0.9108 0.1436 0.8817 0.095 Uiso 1 1 calc R . . C14 C 0.82289(13) 0.0788(2) 0.78623(11) 0.0623(6) Uani 1 1 d . . . H14 H 0.7884 0.1531 0.7839 0.075 Uiso 1 1 calc R . . C15 C 0.79753(10) -0.0232(2) 0.72895(10) 0.0448(4) Uani 1 1 d . . . C16 C 0.72213(10) -0.01905(19) 0.66804(10) 0.0460(4) Uani 1 1 d . . . H16 H 0.6861 0.0518 0.6660 0.055 Uiso 1 1 calc R . . C17 C 0.70071(10) -0.11499(19) 0.61262(10) 0.0441(4) Uani 1 1 d . . . C18 C 0.60669(10) -0.03629(19) 0.49360(10) 0.0447(4) Uani 1 1 d . . . C19 C 0.53062(11) -0.0539(2) 0.43549(11) 0.0549(5) Uani 1 1 d . . . H19 H 0.4948 -0.1176 0.4397 0.066 Uiso 1 1 calc R . . C20 C 0.51060(11) 0.0232(2) 0.37364(11) 0.0566(5) Uani 1 1 d . . . H20 H 0.4593 0.0168 0.3337 0.068 Uiso 1 1 calc R . . C21 C 0.56581(10) 0.11337(19) 0.36821(10) 0.0463(4) Uani 1 1 d . . . C22 C 0.55254(11) 0.1933(2) 0.30495(10) 0.0562(5) Uani 1 1 d . . . H22 H 0.5024 0.1932 0.2630 0.067 Uiso 1 1 calc R . . C23 C 0.61125(12) 0.2702(2) 0.30417(10) 0.0549(5) Uani 1 1 d . . . H23 H 0.6037 0.3243 0.2621 0.066 Uiso 1 1 calc R . . C24 C 0.68398(10) 0.26639(19) 0.36838(9) 0.0438(4) Uani 1 1 d . . . C25 C 0.81872(10) 0.3227(2) 0.42045(10) 0.0461(4) Uani 1 1 d . . . C26 C 0.84951(11) 0.4216(2) 0.47444(10) 0.0477(5) Uani 1 1 d . . . H26 H 0.8179 0.4981 0.4757 0.057 Uiso 1 1 calc R . . C27 C 0.92819(11) 0.4127(2) 0.52915(10) 0.0501(5) Uani 1 1 d . . . C28 C 0.96251(13) 0.5132(3) 0.58709(12) 0.0682(6) Uani 1 1 d . . . H28 H 0.9323 0.5908 0.5896 0.082 Uiso 1 1 calc R . . C29 C 1.03810(17) 0.5004(4) 0.63923(14) 0.0897(9) Uani 1 1 d . . . H29 H 1.0600 0.5678 0.6784 0.108 Uiso 1 1 calc R . . C30 C 1.08371(16) 0.3888(4) 0.63555(17) 0.1009(11) Uani 1 1 d . . . H30 H 1.1366 0.3810 0.6722 0.121 Uiso 1 1 calc R . . C31 C 1.05360(14) 0.2915(3) 0.58045(16) 0.0839(8) Uani 1 1 d . . . H31 H 1.0857 0.2166 0.5786 0.101 Uiso 1 1 calc R . . C32 C 0.97468(11) 0.3002(2) 0.52547(12) 0.0570(5) Uani 1 1 d . . . C33 C 0.94083(13) 0.2003(2) 0.46734(12) 0.0620(6) Uani 1 1 d . . . H33 H 0.9719 0.1253 0.4637 0.074 Uiso 1 1 calc R . . C34 C 0.86474(13) 0.2099(2) 0.41672(10) 0.0532(5) Uani 1 1 d . . . C35 C 0.75978(10) -0.15657(18) 0.42547(9) 0.0434(4) Uani 1 1 d . . . C36 C 0.64071(9) 0.12185(17) 0.42992(9) 0.0372(4) Uani 1 1 d . . . N1 N 0.80266(9) -0.04194(15) 0.42478(7) 0.0460(4) Uani 1 1 d . . . N2 N 0.76652(8) -0.19098(15) 0.49251(8) 0.0425(3) Uani 1 1 d . . . N3 N 0.65948(8) 0.04798(14) 0.49330(7) 0.0390(3) Uani 1 1 d . . . N4 N 0.69924(8) 0.20086(15) 0.42960(7) 0.0400(3) Uani 1 1 d . . . O1 O 0.83147(10) 0.11810(16) 0.35607(8) 0.0743(5) Uani 1 1 d . . . O2 O 0.72566(9) -0.32730(14) 0.56086(8) 0.0639(4) Uani 1 1 d . . . O3 O 0.62426(7) -0.11807(14) 0.55490(7) 0.0577(4) Uani 1 1 d . . . O4 O 0.74255(7) 0.33882(15) 0.36336(7) 0.0569(4) Uani 1 1 d . . . C37 C 0.30104(15) 0.1216(2) 0.15787(13) 0.0637(6) Uani 1 1 d . . . C38 C 0.22790(17) 0.1641(2) 0.09652(13) 0.0959(10) Uani 1 1 d . . . H38A H 0.2193 0.1098 0.0525 0.144 Uiso 1 1 calc R . . H38B H 0.2293 0.2668 0.0872 0.144 Uiso 1 1 calc R . . H38C H 0.1854 0.1446 0.1082 0.144 Uiso 1 1 calc R . . N5 N 0.35732(14) 0.0880(2) 0.20481(13) 0.0984(8) Uani 1 1 d . . . C39 C 0.95656(16) -0.0104(3) 0.64473(13) 0.0703(6) Uani 1 1 d . . . C40 C 0.88707(13) 0.0760(2) 0.60681(12) 0.0638(6) Uani 1 1 d . . . H40A H 0.8488 0.0476 0.6228 0.096 Uiso 1 1 calc R . . H40B H 0.8649 0.0614 0.5535 0.096 Uiso 1 1 calc R . . H40C H 0.9004 0.1773 0.6185 0.096 Uiso 1 1 calc R . . N6 N 1.01110(15) -0.0782(3) 0.67605(14) 0.1119(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0844(15) 0.0540(12) 0.0396(11) 0.0037(9) 0.0335(11) 0.0187(11) C2 0.119(2) 0.0633(14) 0.0359(11) 0.0016(10) 0.0352(13) 0.0264(14) C3 0.1013(18) 0.0619(14) 0.0326(11) -0.0126(10) 0.0103(11) 0.0291(13) C4 0.0598(12) 0.0470(11) 0.0390(10) -0.0094(8) 0.0086(9) 0.0179(10) C5 0.0528(12) 0.0496(12) 0.0573(14) -0.0223(10) 0.0003(11) 0.0062(10) C6 0.0476(12) 0.0515(12) 0.0711(15) -0.0175(10) 0.0187(11) -0.0054(9) C7 0.0479(11) 0.0423(10) 0.0525(11) -0.0092(8) 0.0223(9) -0.0003(8) C8 0.0635(12) 0.0386(9) 0.0500(11) -0.0015(8) 0.0370(10) -0.0105(9) C9 0.0542(12) 0.0405(10) 0.0617(12) 0.0078(9) 0.0362(11) 0.0056(9) C10 0.0466(10) 0.0501(10) 0.0448(10) 0.0100(8) 0.0260(9) 0.0051(8) C11 0.0473(12) 0.0819(15) 0.0634(14) 0.0142(12) 0.0256(11) 0.0145(11) C12 0.0538(14) 0.122(2) 0.0513(14) -0.0114(14) 0.0118(11) -0.0003(14) C13 0.0667(15) 0.110(2) 0.0592(15) -0.0280(13) 0.0282(13) -0.0031(14) C14 0.0568(13) 0.0798(14) 0.0543(13) -0.0136(11) 0.0294(11) 0.0017(11) C15 0.0456(10) 0.0543(11) 0.0403(10) 0.0023(8) 0.0251(9) 0.0022(8) C16 0.0470(11) 0.0469(10) 0.0482(11) 0.0074(8) 0.0258(9) 0.0074(8) C17 0.0436(10) 0.0478(10) 0.0400(10) 0.0073(8) 0.0190(9) -0.0047(8) C18 0.0423(10) 0.0448(10) 0.0428(10) -0.0028(8) 0.0165(9) -0.0035(8) C19 0.0417(11) 0.0607(12) 0.0555(12) -0.0025(10) 0.0171(10) -0.0115(9) C20 0.0332(10) 0.0684(13) 0.0513(12) -0.0041(10) 0.0058(9) -0.0064(9) C21 0.0359(9) 0.0518(10) 0.0395(10) -0.0019(8) 0.0082(8) 0.0017(8) C22 0.0409(11) 0.0677(13) 0.0378(10) 0.0039(9) 0.0001(9) 0.0021(10) C23 0.0576(12) 0.0609(12) 0.0337(10) 0.0069(9) 0.0113(9) 0.0024(10) C24 0.0431(10) 0.0500(10) 0.0343(9) -0.0002(8) 0.0148(8) 0.0003(8) C25 0.0418(10) 0.0600(11) 0.0391(10) 0.0118(9) 0.0211(9) 0.0000(9) C26 0.0416(10) 0.0532(11) 0.0502(11) 0.0098(9) 0.0232(9) 0.0040(8) C27 0.0423(10) 0.0588(11) 0.0485(11) 0.0158(9) 0.0208(9) -0.0038(9) C28 0.0631(14) 0.0771(15) 0.0551(13) 0.0090(11) 0.0201(12) -0.0158(12) C29 0.0707(17) 0.120(2) 0.0551(15) 0.0184(15) 0.0104(14) -0.0366(17) C30 0.0459(15) 0.153(3) 0.0769(19) 0.048(2) 0.0067(14) -0.0166(18) C31 0.0470(13) 0.114(2) 0.0909(19) 0.0553(17) 0.0329(14) 0.0182(14) C32 0.0443(11) 0.0702(14) 0.0615(13) 0.0276(11) 0.0290(10) 0.0067(10) C33 0.0670(14) 0.0666(14) 0.0733(15) 0.0318(12) 0.0502(13) 0.0243(11) C34 0.0730(14) 0.0548(11) 0.0462(11) 0.0123(9) 0.0399(11) 0.0045(10) C35 0.0467(10) 0.0392(9) 0.0380(10) -0.0055(7) 0.0147(8) 0.0112(8) C36 0.0354(9) 0.0380(9) 0.0336(9) -0.0051(7) 0.0123(8) 0.0019(7) N1 0.0598(10) 0.0450(8) 0.0336(8) -0.0016(6) 0.0223(8) 0.0078(7) N2 0.0469(8) 0.0415(8) 0.0377(8) -0.0073(6) 0.0188(7) -0.0017(7) N3 0.0350(8) 0.0408(8) 0.0351(8) -0.0003(6) 0.0115(6) -0.0009(6) N4 0.0362(8) 0.0467(8) 0.0322(8) -0.0011(6) 0.0119(6) -0.0008(6) O1 0.1243(14) 0.0656(9) 0.0512(9) 0.0070(7) 0.0565(10) 0.0022(9) O2 0.0852(10) 0.0497(8) 0.0688(10) -0.0152(7) 0.0461(9) -0.0238(7) O3 0.0487(8) 0.0639(8) 0.0518(8) 0.0099(7) 0.0163(7) -0.0140(6) O4 0.0489(8) 0.0759(9) 0.0392(7) 0.0134(6) 0.0153(6) -0.0054(7) C37 0.0739(16) 0.0443(11) 0.0568(13) 0.0064(10) 0.0173(12) -0.0039(11) C38 0.114(2) 0.0543(13) 0.0629(15) 0.0062(12) -0.0052(15) 0.0146(14) N5 0.0791(16) 0.0888(15) 0.0869(16) 0.0076(13) 0.0056(13) -0.0120(13) C39 0.0716(16) 0.0923(18) 0.0581(14) -0.0133(13) 0.0397(14) -0.0151(14) C40 0.0786(16) 0.0617(13) 0.0573(13) -0.0023(10) 0.0371(12) -0.0135(12) N6 0.0865(17) 0.164(3) 0.0903(18) 0.0032(17) 0.0460(15) 0.0284(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.302(2) . ? C1 O1 1.361(3) . ? C1 C2 1.411(3) . ? C2 C3 1.341(3) . ? C3 C4 1.419(3) . ? C4 C5 1.411(3) . ? C4 C35 1.412(2) . ? C5 C6 1.343(3) . ? C6 C7 1.403(3) . ? C7 N2 1.295(2) . ? C7 O2 1.376(2) . ? C8 C9 1.354(2) . ? C8 O2 1.396(2) . ? C8 C17 1.405(3) . ? C9 C10 1.401(3) . ? C10 C15 1.419(2) . ? C10 C11 1.422(3) . ? C11 C12 1.363(3) . ? C12 C13 1.395(3) . ? C13 C14 1.343(3) . ? C14 C15 1.410(3) . ? C15 C16 1.411(2) . ? C16 C17 1.351(2) . ? C17 O3 1.399(2) . ? C18 N3 1.295(2) . ? C18 O3 1.371(2) . ? C18 C19 1.407(2) . ? C19 C20 1.348(3) . ? C20 C21 1.409(3) . ? C21 C22 1.413(3) . ? C21 C36 1.413(2) . ? C22 C23 1.355(3) . ? C23 C24 1.409(2) . ? C24 N4 1.301(2) . ? C24 O4 1.369(2) . ? C25 C26 1.347(3) . ? C25 O4 1.399(2) . ? C25 C34 1.407(3) . ? C26 C27 1.412(2) . ? C27 C32 1.411(3) . ? C27 C28 1.412(3) . ? C28 C29 1.357(3) . ? C29 C30 1.393(4) . ? C30 C31 1.350(4) . ? C31 C32 1.417(3) . ? C32 C33 1.410(3) . ? C33 C34 1.353(3) . ? C34 O1 1.395(2) . ? C35 N2 1.359(2) . ? C35 N1 1.360(2) . ? C36 N4 1.359(2) . ? C36 N3 1.362(2) . ? C37 N5 1.110(3) . ? C37 C38 1.443(3) . ? C39 N6 1.139(3) . ? C39 C40 1.446(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 N1 C1 O1 119.21(18) . . ? N1 C1 C2 125.5(2) . . ? O1 C1 C2 115.30(18) . . ? C3 C2 C1 117.6(2) . . ? C2 C3 C4 120.23(19) . . ? C5 C4 C35 117.87(18) . . ? C5 C4 C3 125.20(19) . . ? C35 C4 C3 116.9(2) . . ? C6 C5 C4 119.52(18) . . ? C5 C6 C7 117.8(2) . . ? N2 C7 O2 118.48(16) . . ? N2 C7 C6 125.88(19) . . ? O2 C7 C6 115.63(18) . . ? C9 C8 O2 120.71(17) . . ? C9 C8 C17 120.79(16) . . ? O2 C8 C17 118.16(17) . . ? C8 C9 C10 120.45(17) . . ? C9 C10 C15 119.05(17) . . ? C9 C10 C11 122.99(18) . . ? C15 C10 C11 117.95(18) . . ? C12 C11 C10 120.4(2) . . ? C11 C12 C13 121.0(2) . . ? C14 C13 C12 120.1(2) . . ? C13 C14 C15 121.4(2) . . ? C14 C15 C16 122.07(18) . . ? C14 C15 C10 119.12(18) . . ? C16 C15 C10 118.82(17) . . ? C17 C16 C15 120.58(17) . . ? C16 C17 O3 120.73(17) . . ? C16 C17 C8 120.28(17) . . ? O3 C17 C8 118.73(16) . . ? N3 C18 O3 119.11(16) . . ? N3 C18 C19 125.90(17) . . ? O3 C18 C19 114.99(16) . . ? C20 C19 C18 117.35(18) . . ? C19 C20 C21 120.00(17) . . ? C20 C21 C22 124.87(17) . . ? C20 C21 C36 117.69(17) . . ? C22 C21 C36 117.42(17) . . ? C23 C22 C21 120.00(17) . . ? C22 C23 C24 117.15(17) . . ? N4 C24 O4 119.02(15) . . ? N4 C24 C23 126.05(17) . . ? O4 C24 C23 114.92(16) . . ? C26 C25 O4 120.09(17) . . ? C26 C25 C34 120.63(18) . . ? O4 C25 C34 119.00(17) . . ? C25 C26 C27 120.70(18) . . ? C32 C27 C28 118.60(19) . . ? C32 C27 C26 118.88(19) . . ? C28 C27 C26 122.5(2) . . ? C29 C28 C27 120.9(3) . . ? C28 C29 C30 120.3(3) . . ? C31 C30 C29 120.8(3) . . ? C30 C31 C32 120.7(3) . . ? C33 C32 C27 118.79(18) . . ? C33 C32 C31 122.5(2) . . ? C27 C32 C31 118.8(2) . . ? C34 C33 C32 120.87(19) . . ? C33 C34 O1 121.71(19) . . ? C33 C34 C25 120.10(19) . . ? O1 C34 C25 117.93(19) . . ? N2 C35 N1 115.39(15) . . ? N2 C35 C4 121.92(18) . . ? N1 C35 C4 122.66(17) . . ? N4 C36 N3 115.49(14) . . ? N4 C36 C21 122.58(15) . . ? N3 C36 C21 121.90(16) . . ? C1 N1 C35 116.81(17) . . ? C7 N2 C35 116.92(15) . . ? C18 N3 C36 117.05(15) . . ? C24 N4 C36 116.67(14) . . ? C1 O1 C34 119.02(14) . . ? C7 O2 C8 117.26(13) . . ? C18 O3 C17 118.23(13) . . ? C24 O4 C25 118.29(13) . . ? N5 C37 C38 179.5(3) . . ? N6 C39 C40 178.4(3) . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.484 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.046 #===END