# 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 _publ_contact_author_name 'Anne Gorden' _publ_contact_author_address ; Department of Chemistry and Biochemistry Auburn University 179 Chemistry Auburn AL 36849 UNITED STATES OF AMERICA ; _publ_contact_author_email GORDEAE@AUBURN.EDU _publ_contact_author_fax '334 844 6959' _publ_contact_author_phone ' 334 844 4063 ' loop_ _publ_author_name 'Mohan S. Bharara' 'Stephen Tonks' 'Anne Gorden' # Attachment 'Bharara_1_Rev.cif' data_p21n _database_code_depnum_ccdc_archive 'CCDC 656873' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H30 N4 O10 U2' _chemical_formula_weight 998.57 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' 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' U U -9.6767 9.6646 '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' _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 11.797(3) _cell_length_b 9.784(2) _cell_length_c 24.594(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.811(4) _cell_angle_gamma 90.00 _cell_volume 2828.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 3270 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour orange _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 11.495 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SHELXPREP-97 (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Bruker APEX' _diffrn_measurement_method 'w/ scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18601 _diffrn_reflns_av_R_equivalents 0.0687 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 23.29 _reflns_number_total 4058 _reflns_number_gt 3270 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART, SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ATOMS v6.1 (Shape Software, 2004)' _computing_publication_material 'SHELXCIF-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^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 4058 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0272 _refine_ls_wR_factor_ref 0.0557 _refine_ls_wR_factor_gt 0.0539 _refine_ls_goodness_of_fit_ref 0.858 _refine_ls_restrained_S_all 0.858 _refine_ls_shift/su_max 0.097 _refine_ls_shift/su_mean 0.001 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 U1 U 0.71998(2) 0.10007(3) 0.063179(11) 0.02639(9) Uani 1 1 d . . . U2 U 0.74456(2) 0.24145(3) -0.082291(11) 0.02850(9) Uani 1 1 d . . . O1 O 0.7295(4) -0.0765(4) 0.04471(19) 0.0325(11) Uani 1 1 d . . . O2 O 0.7111(4) 0.2747(4) 0.0831(2) 0.0382(13) Uani 1 1 d . . . O3 O 0.7207(4) 0.4045(5) -0.0535(2) 0.0405(13) Uani 1 1 d . . . O4 O 0.7677(4) 0.0771(4) -0.11181(19) 0.0362(12) Uani 1 1 d . . . O5 O 0.7887(4) 0.3346(5) -0.16074(19) 0.0379(12) Uani 1 1 d . . . O6 O 0.7323(4) 0.0447(5) 0.15189(18) 0.0351(12) Uani 1 1 d . . . O7 O 0.8487(4) 0.1674(5) -0.00135(18) 0.0352(12) Uani 1 1 d . . . O8 O 0.6245(4) 0.1442(5) -0.02164(18) 0.0325(12) Uani 1 1 d . . . H8A H 0.5462 0.1251 -0.0306 0.039 Uiso 1 1 calc R . . N1 N 0.9290(5) 0.0829(5) 0.0976(2) 0.0281(13) Uani 1 1 d . . . N2 N 0.9533(5) 0.3226(6) -0.0726(2) 0.0309(14) Uani 1 1 d . . . C1 C 0.9508(6) 0.2291(8) 0.0179(3) 0.043(2) Uani 1 1 d . . . H1 H 0.9290 0.3175 0.0346 0.052 Uiso 1 1 calc R . . C2 C 1.0229(6) 0.2664(7) -0.0256(3) 0.0355(18) Uani 1 1 d . . . H2A H 1.0797 0.3351 -0.0117 0.043 Uiso 1 1 calc R . . H2B H 1.0642 0.1846 -0.0370 0.043 Uiso 1 1 calc R . . C3 C 0.9952(6) 0.4216(7) -0.0989(3) 0.0339(18) Uani 1 1 d . . . H3 H 1.0677 0.4538 -0.0848 0.041 Uiso 1 1 calc R . . C4 C 0.9451(6) 0.4902(7) -0.1476(3) 0.0309(17) Uani 1 1 d . . . C5 C 1.0047(6) 0.6038(7) -0.1671(3) 0.0392(19) Uani 1 1 d . . . H5 H 1.0728 0.6343 -0.1475 0.047 Uiso 1 1 calc R . . C6 C 0.9647(7) 0.6699(8) -0.2140(3) 0.048(2) Uani 1 1 d . . . H6 H 1.0034 0.7476 -0.2263 0.058 Uiso 1 1 calc R . . C7 C 0.8677(8) 0.6220(8) -0.2430(3) 0.050(2) Uani 1 1 d . . . H7 H 0.8408 0.6666 -0.2758 0.060 Uiso 1 1 calc R . . C8 C 0.8088(7) 0.5110(8) -0.2254(3) 0.042(2) Uani 1 1 d . . . H8 H 0.7425 0.4798 -0.2464 0.051 Uiso 1 1 calc R . . C9 C 0.8464(6) 0.4439(8) -0.1768(3) 0.0354(18) Uani 1 1 d . . . C10 C 1.0112(6) 0.1478(7) 0.0639(3) 0.0339(18) Uani 1 1 d . . . H10A H 1.0588 0.0765 0.0485 0.041 Uiso 1 1 calc R . . H10B H 1.0618 0.2090 0.0869 0.041 Uiso 1 1 calc R . . O1D1 O 0.5596(4) 0.2469(5) -0.1310(2) 0.0457(14) Uani 1 1 d . . . O1D2 O 0.5193(4) 0.0613(5) 0.07902(19) 0.0359(12) Uani 1 1 d . . . N1D1 N 0.3975(5) 0.3708(6) -0.1325(2) 0.0347(15) Uani 1 1 d . . . N1D2 N 0.3945(5) 0.2120(8) 0.1067(3) 0.054(2) Uani 1 1 d . . . C1D1 C 0.4625(6) 0.2698(8) -0.1161(3) 0.0387(19) Uani 1 1 d . . . H1D1 H 0.4342 0.2080 -0.0906 0.046 Uiso 1 1 calc R . . C1D2 C 0.4603(6) 0.1087(8) 0.1136(3) 0.0403(19) Uani 1 1 d . . . H1D2 H 0.4641 0.0648 0.1481 0.048 Uiso 1 1 calc R . . C2D1 C 0.4353(8) 0.4696(9) -0.1707(4) 0.071(3) Uani 1 1 d . . . H2D4 H 0.5167 0.4568 -0.1745 0.107 Uiso 1 1 calc R . . H2D5 H 0.4222 0.5622 -0.1574 0.107 Uiso 1 1 calc R . . H2D6 H 0.3926 0.4570 -0.2063 0.107 Uiso 1 1 calc R . . C2D2 C 0.3223(7) 0.2571(11) 0.1498(5) 0.093(4) Uani 1 1 d . . . H2D1 H 0.2452 0.2206 0.1421 0.140 Uiso 1 1 calc R . . H2D2 H 0.3193 0.3571 0.1505 0.140 Uiso 1 1 calc R . . H2D3 H 0.3545 0.2233 0.1853 0.140 Uiso 1 1 calc R . . C3D1 C 0.2845(6) 0.3869(8) -0.1153(4) 0.054(2) Uani 1 1 d . . . H3D4 H 0.2688 0.3132 -0.0900 0.081 Uiso 1 1 calc R . . H3D5 H 0.2290 0.3831 -0.1473 0.081 Uiso 1 1 calc R . . H3D6 H 0.2786 0.4753 -0.0971 0.081 Uiso 1 1 calc R . . C3D2 C 0.3877(12) 0.2837(12) 0.0560(5) 0.128(6) Uani 1 1 d . . . H3D1 H 0.4613 0.2789 0.0404 0.192 Uiso 1 1 calc R . . H3D2 H 0.3681 0.3795 0.0621 0.192 Uiso 1 1 calc R . . H3D3 H 0.3290 0.2418 0.0308 0.192 Uiso 1 1 calc R . . C11 C 0.9702(6) 0.0055(7) 0.1359(3) 0.0348(18) Uani 1 1 d . . . H11 H 1.0508 -0.0009 0.1402 0.042 Uiso 1 1 calc R . . C12 C 0.9084(6) -0.0749(7) 0.1740(3) 0.0292(17) Uani 1 1 d . . . C13 C 0.7906(6) -0.0504(7) 0.1806(3) 0.0305(17) Uani 1 1 d . . . C14 C 0.7394(7) -0.1266(8) 0.2198(3) 0.042(2) Uani 1 1 d . . . H14 H 0.6627 -0.1081 0.2264 0.051 Uiso 1 1 calc R . . C15 C 0.7979(7) -0.2283(7) 0.2492(3) 0.045(2) Uani 1 1 d . . . H15 H 0.7605 -0.2811 0.2748 0.054 Uiso 1 1 calc R . . C16 C 0.9132(8) -0.2541(7) 0.2414(3) 0.048(2) Uani 1 1 d . . . H16 H 0.9537 -0.3247 0.2611 0.057 Uiso 1 1 calc R . . C17 C 0.9653(7) -0.1757(7) 0.2050(3) 0.0394(19) Uani 1 1 d . . . H17 H 1.0435 -0.1909 0.2007 0.047 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 U1 0.02391(15) 0.02625(16) 0.02918(16) 0.00009(12) 0.00323(11) 0.00187(12) U2 0.02394(15) 0.03129(16) 0.03023(16) 0.00227(12) 0.00208(12) 0.00153(12) O1 0.034(3) 0.019(3) 0.046(3) -0.005(2) 0.007(2) 0.001(2) O2 0.041(3) 0.017(3) 0.056(3) -0.003(2) -0.002(3) 0.004(2) O3 0.047(3) 0.028(3) 0.046(3) -0.005(2) 0.007(3) 0.007(2) O4 0.033(3) 0.028(3) 0.048(3) -0.007(2) 0.006(2) 0.000(2) O5 0.035(3) 0.044(3) 0.034(3) 0.007(2) 0.004(2) -0.011(2) O6 0.033(3) 0.042(3) 0.032(3) 0.008(2) 0.011(2) 0.007(2) O7 0.023(3) 0.046(3) 0.035(3) 0.010(2) -0.009(2) -0.008(2) O8 0.016(2) 0.046(3) 0.034(3) 0.004(2) -0.002(2) -0.003(2) N1 0.028(3) 0.031(3) 0.026(3) -0.002(3) 0.002(3) 0.002(3) N2 0.030(3) 0.034(3) 0.029(3) 0.000(3) 0.004(3) -0.004(3) C1 0.026(4) 0.061(6) 0.042(5) 0.011(4) -0.003(4) -0.005(4) C2 0.024(4) 0.043(5) 0.041(5) -0.002(4) 0.005(4) -0.003(3) C3 0.031(4) 0.030(4) 0.042(5) -0.006(4) 0.008(4) 0.004(3) C4 0.032(4) 0.034(4) 0.029(4) 0.000(3) 0.011(3) 0.008(3) C5 0.042(5) 0.032(4) 0.045(5) -0.003(4) 0.013(4) 0.003(4) C6 0.061(6) 0.039(5) 0.049(6) 0.008(4) 0.024(5) 0.004(4) C7 0.061(6) 0.058(6) 0.033(5) 0.015(4) 0.022(5) 0.019(5) C8 0.047(5) 0.059(5) 0.022(4) 0.007(4) 0.006(4) 0.018(4) C9 0.034(4) 0.042(5) 0.032(5) -0.005(4) 0.011(4) 0.013(4) C10 0.028(4) 0.043(5) 0.030(4) -0.001(3) -0.002(3) 0.003(3) O1D1 0.021(3) 0.077(4) 0.038(3) 0.010(3) 0.002(2) 0.007(3) O1D2 0.027(3) 0.040(3) 0.042(3) -0.006(2) 0.012(2) 0.003(2) N1D1 0.029(3) 0.027(3) 0.048(4) 0.003(3) -0.002(3) -0.002(3) N1D2 0.030(4) 0.067(5) 0.064(5) -0.033(4) -0.003(4) 0.015(4) C1D1 0.029(5) 0.044(5) 0.043(5) 0.010(4) -0.002(4) -0.003(4) C1D2 0.032(4) 0.043(5) 0.047(5) -0.004(4) 0.011(4) -0.006(4) C2D1 0.075(7) 0.056(6) 0.082(7) 0.031(5) 0.006(6) 0.005(5) C2D2 0.034(5) 0.118(9) 0.129(10) -0.079(8) 0.016(6) 0.014(6) C3D1 0.035(5) 0.044(5) 0.083(7) -0.012(5) 0.004(5) 0.007(4) C3D2 0.191(15) 0.101(10) 0.084(9) -0.022(8) -0.033(9) 0.099(10) C11 0.028(4) 0.035(4) 0.041(5) -0.012(4) 0.001(4) 0.010(3) C12 0.039(4) 0.025(4) 0.023(4) -0.005(3) 0.002(3) 0.007(3) C13 0.040(4) 0.032(4) 0.019(4) -0.006(3) -0.001(3) -0.003(4) C14 0.043(5) 0.051(5) 0.031(5) -0.002(4) 0.002(4) -0.011(4) C15 0.064(6) 0.030(5) 0.039(5) 0.008(4) -0.003(4) -0.010(4) C16 0.068(6) 0.030(4) 0.045(5) 0.006(4) 0.000(5) 0.001(4) C17 0.040(5) 0.040(5) 0.037(5) -0.003(4) -0.002(4) 0.005(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 U1 O2 1.783(4) . ? U1 O1 1.792(4) . ? U1 O6 2.241(5) . ? U1 O8 2.327(4) . ? U1 O7 2.380(5) . ? U1 O1D2 2.461(4) . ? U1 N1 2.544(5) . ? U1 U2 3.8693(8) . ? U2 O3 1.778(4) . ? U2 O4 1.794(4) . ? U2 O5 2.235(5) . ? U2 O8 2.343(4) . ? U2 O7 2.364(4) . ? U2 O1D1 2.400(5) . ? U2 N2 2.579(5) . ? O5 C9 1.344(8) . ? O6 C13 1.325(8) . ? O7 C1 1.394(8) . ? O8 H8A 0.9500 . ? N1 C11 1.272(8) . ? N1 C10 1.473(8) . ? N2 C3 1.286(8) . ? N2 C2 1.468(8) . ? C1 C2 1.467(10) . ? C1 C10 1.510(9) . ? C1 H1 1.0000 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.455(9) . ? C3 H3 0.9500 . ? C4 C9 1.392(10) . ? C4 C5 1.420(9) . ? C5 C6 1.370(10) . ? C5 H5 0.9500 . ? C6 C7 1.379(11) . ? C6 H6 0.9500 . ? C7 C8 1.377(11) . ? C7 H7 0.9500 . ? C8 C9 1.403(10) . ? C8 H8 0.9500 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? O1D1 C1D1 1.253(8) . ? O1D2 C1D2 1.234(8) . ? N1D1 C1D1 1.294(8) . ? N1D1 C3D1 1.441(9) . ? N1D1 C2D1 1.446(10) . ? N1D2 C1D2 1.277(9) . ? N1D2 C3D2 1.427(13) . ? N1D2 C2D2 1.481(11) . ? C1D1 H1D1 0.9500 . ? C1D2 H1D2 0.9500 . ? C2D1 H2D4 0.9800 . ? C2D1 H2D5 0.9800 . ? C2D1 H2D6 0.9800 . ? C2D2 H2D1 0.9800 . ? C2D2 H2D2 0.9800 . ? C2D2 H2D3 0.9800 . ? C3D1 H3D4 0.9800 . ? C3D1 H3D5 0.9800 . ? C3D1 H3D6 0.9800 . ? C3D2 H3D1 0.9800 . ? C3D2 H3D2 0.9800 . ? C3D2 H3D3 0.9800 . ? C11 C12 1.465(10) . ? C11 H11 0.9500 . ? C12 C17 1.384(9) . ? C12 C13 1.433(9) . ? C13 C14 1.395(10) . ? C14 C15 1.381(10) . ? C14 H14 0.9500 . ? C15 C16 1.412(11) . ? C15 H15 0.9500 . ? C16 C17 1.363(10) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 U1 O1 178.7(2) . . ? O2 U1 O6 88.0(2) . . ? O1 U1 O6 90.76(19) . . ? O2 U1 O8 91.90(19) . . ? O1 U1 O8 89.29(18) . . ? O6 U1 O8 154.81(16) . . ? O2 U1 O7 88.5(2) . . ? O1 U1 O7 92.34(18) . . ? O6 U1 O7 136.31(15) . . ? O8 U1 O7 68.84(14) . . ? O2 U1 O1D2 91.43(19) . . ? O1 U1 O1D2 88.44(18) . . ? O6 U1 O1D2 78.08(16) . . ? O8 U1 O1D2 76.74(15) . . ? O7 U1 O1D2 145.55(15) . . ? O2 U1 N1 92.83(19) . . ? O1 U1 N1 86.64(18) . . ? O6 U1 N1 71.19(17) . . ? O8 U1 N1 133.93(16) . . ? O7 U1 N1 65.52(16) . . ? O1D2 U1 N1 148.79(17) . . ? O2 U1 U2 85.53(16) . . ? O1 U1 U2 95.69(15) . . ? O6 U1 U2 169.38(12) . . ? O8 U1 U2 34.19(11) . . ? O7 U1 U2 35.21(10) . . ? O1D2 U1 U2 110.44(11) . . ? N1 U1 U2 100.71(12) . . ? O3 U2 O4 179.5(2) . . ? O3 U2 O5 92.0(2) . . ? O4 U2 O5 87.8(2) . . ? O3 U2 O8 89.20(19) . . ? O4 U2 O8 90.83(19) . . ? O5 U2 O8 155.83(16) . . ? O3 U2 O7 91.6(2) . . ? O4 U2 O7 88.85(19) . . ? O5 U2 O7 135.22(16) . . ? O8 U2 O7 68.83(15) . . ? O3 U2 O1D1 90.7(2) . . ? O4 U2 O1D1 88.90(19) . . ? O5 U2 O1D1 80.07(17) . . ? O8 U2 O1D1 75.77(16) . . ? O7 U2 O1D1 144.49(16) . . ? O3 U2 N2 82.5(2) . . ? O4 U2 N2 97.86(19) . . ? O5 U2 N2 70.39(17) . . ? O8 U2 N2 133.59(16) . . ? O7 U2 N2 65.89(16) . . ? O1D1 U2 N2 149.33(17) . . ? O3 U2 U1 85.72(16) . . ? O4 U2 U1 94.56(15) . . ? O5 U2 U1 170.12(12) . . ? O8 U2 U1 33.92(10) . . ? O7 U2 U1 35.49(11) . . ? O1D1 U2 U1 109.53(12) . . ? N2 U2 U1 99.76(12) . . ? C9 O5 U2 137.6(4) . . ? C13 O6 U1 132.6(4) . . ? C1 O7 U2 121.8(4) . . ? C1 O7 U1 118.3(4) . . ? U2 O7 U1 109.30(17) . . ? U1 O8 U2 111.89(17) . . ? U1 O8 H8A 124.1 . . ? U2 O8 H8A 124.1 . . ? C11 N1 C10 116.4(6) . . ? C11 N1 U1 125.8(5) . . ? C10 N1 U1 116.7(4) . . ? C3 N2 C2 117.7(6) . . ? C3 N2 U2 126.1(5) . . ? C2 N2 U2 115.1(4) . . ? O7 C1 C2 113.3(6) . . ? O7 C1 C10 111.5(6) . . ? C2 C1 C10 114.3(6) . . ? O7 C1 H1 105.6 . . ? C2 C1 H1 105.6 . . ? C10 C1 H1 105.6 . . ? N2 C2 C1 110.3(6) . . ? N2 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? N2 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? N2 C3 C4 127.9(7) . . ? N2 C3 H3 116.0 . . ? C4 C3 H3 116.0 . . ? C9 C4 C5 119.8(7) . . ? C9 C4 C3 122.7(7) . . ? C5 C4 C3 117.4(7) . . ? C6 C5 C4 120.5(7) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 119.2(8) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C8 C7 C6 121.6(8) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C7 C8 C9 120.3(8) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? O5 C9 C4 121.9(6) . . ? O5 C9 C8 119.5(7) . . ? C4 C9 C8 118.6(7) . . ? N1 C10 C1 111.0(6) . . ? N1 C10 H10A 109.4 . . ? C1 C10 H10A 109.4 . . ? N1 C10 H10B 109.4 . . ? C1 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C1D1 O1D1 U2 132.3(5) . . ? C1D2 O1D2 U1 131.1(4) . . ? C1D1 N1D1 C3D1 122.1(7) . . ? C1D1 N1D1 C2D1 120.5(7) . . ? C3D1 N1D1 C2D1 117.4(7) . . ? C1D2 N1D2 C3D2 119.6(8) . . ? C1D2 N1D2 C2D2 121.4(9) . . ? C3D2 N1D2 C2D2 119.0(8) . . ? O1D1 C1D1 N1D1 125.2(7) . . ? O1D1 C1D1 H1D1 117.4 . . ? N1D1 C1D1 H1D1 117.4 . . ? O1D2 C1D2 N1D2 125.3(8) . . ? O1D2 C1D2 H1D2 117.3 . . ? N1D2 C1D2 H1D2 117.3 . . ? N1D1 C2D1 H2D4 109.5 . . ? N1D1 C2D1 H2D5 109.5 . . ? H2D4 C2D1 H2D5 109.5 . . ? N1D1 C2D1 H2D6 109.5 . . ? H2D4 C2D1 H2D6 109.5 . . ? H2D5 C2D1 H2D6 109.5 . . ? N1D2 C2D2 H2D1 109.5 . . ? N1D2 C2D2 H2D2 109.5 . . ? H2D1 C2D2 H2D2 109.5 . . ? N1D2 C2D2 H2D3 109.5 . . ? H2D1 C2D2 H2D3 109.5 . . ? H2D2 C2D2 H2D3 109.5 . . ? N1D1 C3D1 H3D4 109.5 . . ? N1D1 C3D1 H3D5 109.5 . . ? H3D4 C3D1 H3D5 109.5 . . ? N1D1 C3D1 H3D6 109.5 . . ? H3D4 C3D1 H3D6 109.5 . . ? H3D5 C3D1 H3D6 109.5 . . ? N1D2 C3D2 H3D1 109.5 . . ? N1D2 C3D2 H3D2 109.5 . . ? H3D1 C3D2 H3D2 109.5 . . ? N1D2 C3D2 H3D3 109.5 . . ? H3D1 C3D2 H3D3 109.5 . . ? H3D2 C3D2 H3D3 109.5 . . ? N1 C11 C12 127.8(7) . . ? N1 C11 H11 116.1 . . ? C12 C11 H11 116.1 . . ? C17 C12 C13 119.1(7) . . ? C17 C12 C11 119.4(7) . . ? C13 C12 C11 121.5(6) . . ? O6 C13 C14 120.5(7) . . ? O6 C13 C12 121.5(6) . . ? C14 C13 C12 118.0(7) . . ? C15 C14 C13 121.4(8) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C16 120.1(7) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C17 C16 C15 118.8(7) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C16 C17 C12 122.5(7) . . ? C16 C17 H17 118.7 . . ? C12 C17 H17 118.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 U1 U2 O3 -5.1(2) . . . . ? O1 U1 U2 O3 175.2(2) . . . . ? O6 U1 U2 O3 -57.6(7) . . . . ? O8 U1 U2 O3 94.9(3) . . . . ? O7 U1 U2 O3 -98.8(3) . . . . ? O1D2 U1 U2 O3 84.76(19) . . . . ? N1 U1 U2 O3 -97.1(2) . . . . ? O2 U1 U2 O4 175.3(2) . . . . ? O1 U1 U2 O4 -4.4(2) . . . . ? O6 U1 U2 O4 122.8(7) . . . . ? O8 U1 U2 O4 -84.7(2) . . . . ? O7 U1 U2 O4 81.6(2) . . . . ? O1D2 U1 U2 O4 -94.87(18) . . . . ? N1 U1 U2 O4 83.23(19) . . . . ? O2 U1 U2 O5 71.7(8) . . . . ? O1 U1 U2 O5 -107.9(8) . . . . ? O6 U1 U2 O5 19.2(10) . . . . ? O8 U1 U2 O5 171.8(8) . . . . ? O7 U1 U2 O5 -22.0(8) . . . . ? O1D2 U1 U2 O5 161.6(8) . . . . ? N1 U1 U2 O5 -20.3(8) . . . . ? O2 U1 U2 O8 -100.0(2) . . . . ? O1 U1 U2 O8 80.3(2) . . . . ? O6 U1 U2 O8 -152.5(7) . . . . ? O7 U1 U2 O8 166.3(3) . . . . ? O1D2 U1 U2 O8 -10.2(2) . . . . ? N1 U1 U2 O8 167.9(2) . . . . ? O2 U1 U2 O7 93.7(3) . . . . ? O1 U1 U2 O7 -86.0(2) . . . . ? O6 U1 U2 O7 41.2(7) . . . . ? O8 U1 U2 O7 -166.3(3) . . . . ? O1D2 U1 U2 O7 -176.4(2) . . . . ? N1 U1 U2 O7 1.7(2) . . . . ? O2 U1 U2 O1D1 -94.3(2) . . . . ? O1 U1 U2 O1D1 86.04(19) . . . . ? O6 U1 U2 O1D1 -146.8(7) . . . . ? O8 U1 U2 O1D1 5.8(2) . . . . ? O7 U1 U2 O1D1 172.0(2) . . . . ? O1D2 U1 U2 O1D1 -4.42(17) . . . . ? N1 U1 U2 O1D1 173.68(18) . . . . ? O2 U1 U2 N2 76.5(2) . . . . ? O1 U1 U2 N2 -103.20(19) . . . . ? O6 U1 U2 N2 24.0(6) . . . . ? O8 U1 U2 N2 176.5(2) . . . . ? O7 U1 U2 N2 -17.2(2) . . . . ? O1D2 U1 U2 N2 166.34(17) . . . . ? N1 U1 U2 N2 -15.56(18) . . . . ? O3 U2 O5 C9 39.3(6) . . . . ? O4 U2 O5 C9 -141.1(6) . . . . ? O8 U2 O5 C9 131.8(6) . . . . ? O7 U2 O5 C9 -54.9(7) . . . . ? O1D1 U2 O5 C9 129.6(6) . . . . ? N2 U2 O5 C9 -41.9(6) . . . . ? U1 U2 O5 C9 -37.0(12) . . . . ? O2 U1 O6 C13 -143.4(6) . . . . ? O1 U1 O6 C13 36.5(6) . . . . ? O8 U1 O6 C13 126.5(6) . . . . ? O7 U1 O6 C13 -57.7(7) . . . . ? O1D2 U1 O6 C13 124.7(6) . . . . ? N1 U1 O6 C13 -49.7(6) . . . . ? U2 U1 O6 C13 -91.1(9) . . . . ? O3 U2 O7 C1 -63.6(5) . . . . ? O4 U2 O7 C1 116.6(5) . . . . ? O5 U2 O7 C1 30.8(6) . . . . ? O8 U2 O7 C1 -152.1(6) . . . . ? O1D1 U2 O7 C1 -156.9(5) . . . . ? N2 U2 O7 C1 17.4(5) . . . . ? U1 U2 O7 C1 -143.9(6) . . . . ? O3 U2 O7 U1 80.3(2) . . . . ? O4 U2 O7 U1 -99.5(2) . . . . ? O5 U2 O7 U1 174.77(19) . . . . ? O8 U2 O7 U1 -8.18(17) . . . . ? O1D1 U2 O7 U1 -13.0(4) . . . . ? N2 U2 O7 U1 161.4(3) . . . . ? O2 U1 O7 C1 61.0(5) . . . . ? O1 U1 O7 C1 -118.1(5) . . . . ? O6 U1 O7 C1 -24.5(6) . . . . ? O8 U1 O7 C1 153.6(5) . . . . ? O1D2 U1 O7 C1 151.3(4) . . . . ? N1 U1 O7 C1 -32.8(5) . . . . ? U2 U1 O7 C1 145.4(6) . . . . ? O2 U1 O7 U2 -84.4(2) . . . . ? O1 U1 O7 U2 96.6(2) . . . . ? O6 U1 O7 U2 -169.88(18) . . . . ? O8 U1 O7 U2 8.23(17) . . . . ? O1D2 U1 O7 U2 5.9(4) . . . . ? N1 U1 O7 U2 -178.2(3) . . . . ? O2 U1 O8 U2 79.2(2) . . . . ? O1 U1 O8 U2 -101.2(2) . . . . ? O6 U1 O8 U2 168.5(3) . . . . ? O7 U1 O8 U2 -8.45(17) . . . . ? O1D2 U1 O8 U2 170.2(2) . . . . ? N1 U1 O8 U2 -16.6(3) . . . . ? O3 U2 O8 U1 -83.5(2) . . . . ? O4 U2 O8 U1 97.0(2) . . . . ? O5 U2 O8 U1 -176.6(3) . . . . ? O7 U2 O8 U1 8.51(17) . . . . ? O1D1 U2 O8 U1 -174.4(2) . . . . ? N2 U2 O8 U1 -4.7(3) . . . . ? O2 U1 N1 C11 116.9(6) . . . . ? O1 U1 N1 C11 -62.0(5) . . . . ? O6 U1 N1 C11 30.0(5) . . . . ? O8 U1 N1 C11 -147.7(5) . . . . ? O7 U1 N1 C11 -156.1(6) . . . . ? O1D2 U1 N1 C11 19.4(7) . . . . ? U2 U1 N1 C11 -157.1(5) . . . . ? O2 U1 N1 C10 -75.5(5) . . . . ? O1 U1 N1 C10 105.7(5) . . . . ? O6 U1 N1 C10 -162.4(5) . . . . ? O8 U1 N1 C10 19.9(5) . . . . ? O7 U1 N1 C10 11.6(4) . . . . ? O1D2 U1 N1 C10 -172.9(4) . . . . ? U2 U1 N1 C10 10.5(4) . . . . ? O3 U2 N2 C3 -66.7(6) . . . . ? O4 U2 N2 C3 113.0(6) . . . . ? O5 U2 N2 C3 28.2(5) . . . . ? O8 U2 N2 C3 -148.3(5) . . . . ? O7 U2 N2 C3 -161.8(6) . . . . ? O1D1 U2 N2 C3 11.8(8) . . . . ? U1 U2 N2 C3 -151.0(5) . . . . ? O3 U2 N2 C2 101.2(5) . . . . ? O4 U2 N2 C2 -79.1(5) . . . . ? O5 U2 N2 C2 -164.0(5) . . . . ? O8 U2 N2 C2 19.6(5) . . . . ? O7 U2 N2 C2 6.0(4) . . . . ? O1D1 U2 N2 C2 179.6(4) . . . . ? U1 U2 N2 C2 16.9(4) . . . . ? U2 O7 C1 C2 -38.9(8) . . . . ? U1 O7 C1 C2 -179.8(5) . . . . ? U2 O7 C1 C10 -169.5(4) . . . . ? U1 O7 C1 C10 49.6(8) . . . . ? C3 N2 C2 C1 143.0(7) . . . . ? U2 N2 C2 C1 -25.9(7) . . . . ? O7 C1 C2 N2 40.6(8) . . . . ? C10 C1 C2 N2 169.7(6) . . . . ? C2 N2 C3 C4 177.4(6) . . . . ? U2 N2 C3 C4 -15.0(10) . . . . ? N2 C3 C4 C9 -8.1(11) . . . . ? N2 C3 C4 C5 175.7(7) . . . . ? C9 C4 C5 C6 1.2(10) . . . . ? C3 C4 C5 C6 177.4(6) . . . . ? C4 C5 C6 C7 -2.0(11) . . . . ? C5 C6 C7 C8 1.2(12) . . . . ? C6 C7 C8 C9 0.4(11) . . . . ? U2 O5 C9 C4 36.8(10) . . . . ? U2 O5 C9 C8 -145.5(5) . . . . ? C5 C4 C9 O5 178.2(6) . . . . ? C3 C4 C9 O5 2.2(10) . . . . ? C5 C4 C9 C8 0.5(10) . . . . ? C3 C4 C9 C8 -175.6(6) . . . . ? C7 C8 C9 O5 -179.1(7) . . . . ? C7 C8 C9 C4 -1.3(10) . . . . ? C11 N1 C10 C1 176.3(6) . . . . ? U1 N1 C10 C1 7.4(7) . . . . ? O7 C1 C10 N1 -34.5(8) . . . . ? C2 C1 C10 N1 -164.6(6) . . . . ? O3 U2 O1D1 C1D1 -51.1(7) . . . . ? O4 U2 O1D1 C1D1 129.0(7) . . . . ? O5 U2 O1D1 C1D1 -143.0(7) . . . . ? O8 U2 O1D1 C1D1 37.9(6) . . . . ? O7 U2 O1D1 C1D1 42.5(8) . . . . ? N2 U2 O1D1 C1D1 -127.4(6) . . . . ? U1 U2 O1D1 C1D1 34.6(7) . . . . ? O2 U1 O1D2 C1D2 -35.2(7) . . . . ? O1 U1 O1D2 C1D2 143.5(7) . . . . ? O6 U1 O1D2 C1D2 52.4(7) . . . . ? O8 U1 O1D2 C1D2 -126.8(7) . . . . ? O7 U1 O1D2 C1D2 -124.6(7) . . . . ? N1 U1 O1D2 C1D2 62.6(8) . . . . ? U2 U1 O1D2 C1D2 -121.0(6) . . . . ? U2 O1D1 C1D1 N1D1 117.0(7) . . . . ? C3D1 N1D1 C1D1 O1D1 177.1(7) . . . . ? C2D1 N1D1 C1D1 O1D1 -0.6(12) . . . . ? U1 O1D2 C1D2 N1D2 95.5(9) . . . . ? C3D2 N1D2 C1D2 O1D2 -1.5(13) . . . . ? C2D2 N1D2 C1D2 O1D2 176.8(7) . . . . ? C10 N1 C11 C12 -177.7(6) . . . . ? U1 N1 C11 C12 -10.0(10) . . . . ? N1 C11 C12 C17 165.9(7) . . . . ? N1 C11 C12 C13 -14.9(11) . . . . ? U1 O6 C13 C14 -136.6(6) . . . . ? U1 O6 C13 C12 45.6(9) . . . . ? C17 C12 C13 O6 -179.8(6) . . . . ? C11 C12 C13 O6 1.0(10) . . . . ? C17 C12 C13 C14 2.4(10) . . . . ? C11 C12 C13 C14 -176.8(6) . . . . ? O6 C13 C14 C15 178.4(7) . . . . ? C12 C13 C14 C15 -3.8(10) . . . . ? C13 C14 C15 C16 2.2(11) . . . . ? C14 C15 C16 C17 0.9(11) . . . . ? C15 C16 C17 C12 -2.2(11) . . . . ? C13 C12 C17 C16 0.6(10) . . . . ? C11 C12 C17 C16 179.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.177 _refine_diff_density_min -0.691 _refine_diff_density_rms 0.147 # Attachment 'Bharara_2_Rev.cif' data_pca _database_code_depnum_ccdc_archive 'CCDC 656874' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H19 N3 O4 U' _chemical_formula_weight 615.42 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' 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' U U -9.6767 9.6646 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 18.427(2) _cell_length_b 9.0712(12) _cell_length_c 11.8143(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1974.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 2458 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour orange _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.070 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 8.252 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SHELXPREP-97 (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Bruker APEX' _diffrn_measurement_method 'w/ scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10662 _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 23.28 _reflns_number_total 2838 _reflns_number_gt 2458 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART, SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ATOMS v6.1 (Shape Software, 2004)' _computing_publication_material 'SHELXCIF-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^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 SHELXL _refine_ls_extinction_coef 0.00229(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.001(10) _refine_ls_number_reflns 2838 _refine_ls_number_parameters 263 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0286 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0589 _refine_ls_wR_factor_gt 0.0574 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.002 _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 U1 U 0.498314(8) 0.23171(2) 0.53915(14) 0.02260(11) Uani 1 1 d . . . O1 O 0.42341(18) 0.3479(4) 0.5735(3) 0.0329(11) Uani 1 1 d . . . O2 O 0.57098(18) 0.1141(4) 0.4987(3) 0.0333(10) Uani 1 1 d . . . O3 O 0.44169(18) 0.0359(4) 0.6142(3) 0.0309(9) Uani 1 1 d . . . O4 O 0.57517(18) 0.4213(4) 0.5485(4) 0.0377(10) Uani 1 1 d . . . N1 N 0.4134(2) 0.1211(5) 0.3920(4) 0.0248(11) Uani 1 1 d . . . N2 N 0.5063(2) 0.3530(6) 0.3454(4) 0.0251(12) Uani 1 1 d . . . N3 N 0.5340(3) 0.2449(5) 0.7533(4) 0.0280(12) Uani 1 1 d . . . C1 C 0.3743(3) -0.0113(6) 0.6177(5) 0.0310(14) Uani 1 1 d D . . C2 C 0.3474(3) -0.0853(6) 0.7122(4) 0.0301(13) Uani 1 1 d D . . H2 H 0.3780 -0.0982 0.7762 0.036 Uiso 1 1 calc R . . C3 C 0.2781(3) -0.1399(7) 0.7156(5) 0.0395(16) Uani 1 1 d D . . H3 H 0.2619 -0.1923 0.7804 0.047 Uiso 1 1 calc R . . C4 C 0.2314(3) -0.1189(8) 0.6246(5) 0.0444(18) Uani 1 1 d D . . H4 H 0.1827 -0.1530 0.6280 0.053 Uiso 1 1 calc R . . C5 C 0.2566(3) -0.0486(7) 0.5304(7) 0.0399(15) Uani 1 1 d D . . H5 H 0.2251 -0.0359 0.4675 0.048 Uiso 1 1 calc R . . C6 C 0.3274(3) 0.0051(6) 0.5237(5) 0.0303(14) Uani 1 1 d D . . C7 C 0.3528(3) 0.0575(6) 0.4157(5) 0.0267(12) Uani 1 1 d D . . H7 H 0.3207 0.0433 0.3538 0.032 Uiso 1 1 calc R . . C8 C 0.4285(3) 0.1600(6) 0.2736(5) 0.0311(14) Uani 1 1 d . . . H8A H 0.3858 0.1378 0.2258 0.037 Uiso 1 1 calc R . . H8B H 0.4703 0.1022 0.2450 0.037 Uiso 1 1 calc R . . C9 C 0.4454(3) 0.3212(6) 0.2691(4) 0.0289(14) Uani 1 1 d . . . H9A H 0.4583 0.3499 0.1908 0.035 Uiso 1 1 calc R . . H9B H 0.4023 0.3789 0.2923 0.035 Uiso 1 1 calc R . . C10 C 0.5584(3) 0.4317(6) 0.3067(5) 0.0267(13) Uani 1 1 d D . . H10 H 0.5555 0.4564 0.2287 0.032 Uiso 1 1 calc R . . C11 C 0.6213(3) 0.4878(6) 0.3670(4) 0.0271(13) Uani 1 1 d D . . C12 C 0.6270(3) 0.4791(6) 0.4852(5) 0.0296(14) Uani 1 1 d D . . C13 C 0.6885(3) 0.5454(6) 0.5363(7) 0.0383(14) Uani 1 1 d D . . H13 H 0.6935 0.5427 0.6163 0.046 Uiso 1 1 calc R . . C14 C 0.7401(3) 0.6125(7) 0.4733(6) 0.0413(16) Uani 1 1 d D . . H14 H 0.7808 0.6555 0.5100 0.050 Uiso 1 1 calc R . . C15 C 0.7349(3) 0.6198(7) 0.3554(6) 0.0448(17) Uani 1 1 d D . . H15 H 0.7713 0.6669 0.3114 0.054 Uiso 1 1 calc R . . C16 C 0.6753(3) 0.5567(7) 0.3056(5) 0.0365(15) Uani 1 1 d D . . H16 H 0.6711 0.5604 0.2255 0.044 Uiso 1 1 calc R . . C17 C 0.5950(3) 0.3059(7) 0.7920(5) 0.0339(14) Uani 1 1 d D . . H17 H 0.6305 0.3358 0.7383 0.041 Uiso 1 1 calc R . . C18 C 0.6098(3) 0.3281(6) 0.9046(5) 0.0393(15) Uani 1 1 d D . . H18 H 0.6542 0.3719 0.9279 0.047 Uiso 1 1 calc R . . C19 C 0.5591(4) 0.2858(6) 0.9822(6) 0.0424(17) Uani 1 1 d D . . H19 H 0.5678 0.2998 1.0607 0.051 Uiso 1 1 calc R . . C20 C 0.4955(3) 0.2227(8) 0.9461(8) 0.036(2) Uani 1 1 d D . . H20 H 0.4595 0.1928 0.9988 0.044 Uiso 1 1 calc R . . C21 C 0.4851(4) 0.2039(8) 0.8323(6) 0.0350(17) Uani 1 1 d D . . H21 H 0.4412 0.1596 0.8076 0.042 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 U1 0.02300(15) 0.02492(15) 0.01988(14) 0.0000(5) -0.00079(13) -0.00128(7) O1 0.030(2) 0.037(3) 0.032(3) 0.0014(19) -0.0033(17) 0.0061(18) O2 0.029(2) 0.036(3) 0.035(2) -0.0001(19) -0.0031(17) 0.0071(18) O3 0.028(2) 0.028(2) 0.036(2) 0.0077(19) -0.0015(18) -0.0073(17) O4 0.047(2) 0.042(2) 0.024(2) 0.002(3) 0.002(2) -0.0156(18) N1 0.028(3) 0.025(3) 0.022(3) 0.000(2) -0.0024(19) 0.000(2) N2 0.026(3) 0.023(3) 0.026(3) 0.001(2) 0.0016(19) -0.0002(19) N3 0.032(3) 0.027(3) 0.026(3) -0.001(2) 0.000(3) 0.001(2) C1 0.041(4) 0.022(4) 0.031(3) -0.004(3) 0.004(3) 0.000(3) C2 0.036(3) 0.028(3) 0.026(3) -0.002(3) -0.001(3) 0.000(3) C3 0.044(4) 0.040(4) 0.035(4) 0.007(3) 0.006(3) -0.009(3) C4 0.026(3) 0.066(5) 0.042(4) 0.000(4) 0.002(3) -0.007(3) C5 0.028(3) 0.053(4) 0.039(4) 0.007(5) -0.008(3) -0.006(2) C6 0.029(3) 0.033(3) 0.029(4) -0.003(3) 0.000(3) -0.003(2) C7 0.027(3) 0.027(3) 0.025(3) -0.004(3) -0.004(3) -0.001(3) C8 0.032(3) 0.033(4) 0.029(3) -0.002(3) 0.000(3) -0.006(3) C9 0.030(3) 0.040(4) 0.017(3) 0.000(3) -0.001(2) -0.002(3) C10 0.033(3) 0.025(3) 0.023(3) -0.002(3) 0.001(3) 0.004(3) C11 0.023(3) 0.027(3) 0.031(3) 0.004(3) 0.001(3) 0.002(2) C12 0.035(3) 0.021(3) 0.032(3) 0.003(3) 0.002(3) -0.002(3) C13 0.045(3) 0.040(4) 0.030(3) 0.003(4) -0.011(4) -0.014(3) C14 0.031(4) 0.040(4) 0.053(4) 0.000(3) -0.008(3) -0.005(3) C15 0.036(4) 0.054(5) 0.045(4) 0.001(4) 0.008(3) -0.008(3) C16 0.035(4) 0.042(4) 0.032(3) 0.003(3) 0.002(3) -0.005(3) C17 0.035(4) 0.029(3) 0.037(4) -0.003(3) -0.005(3) 0.005(3) C18 0.046(4) 0.032(4) 0.040(4) -0.005(3) -0.013(3) 0.004(3) C19 0.077(5) 0.028(4) 0.022(3) -0.001(3) -0.010(4) 0.011(3) C20 0.058(6) 0.028(5) 0.023(4) 0.004(3) 0.008(3) 0.000(3) C21 0.037(4) 0.032(4) 0.037(4) -0.001(3) -0.002(3) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag U1 O2 1.778(4) . ? U1 O1 1.783(4) . ? U1 O4 2.230(3) . ? U1 O3 2.243(4) . ? U1 N2 2.544(5) . ? U1 N1 2.544(5) . ? U1 N3 2.617(6) . ? O3 C1 1.314(6) . ? O4 C12 1.322(6) . ? N1 C7 1.288(6) . ? N1 C8 1.470(7) . ? N2 C10 1.281(7) . ? N2 C9 1.467(6) . ? N3 C17 1.333(7) . ? N3 C21 1.350(9) . ? C1 C2 1.394(7) . ? C1 C6 1.416(8) . ? C2 C3 1.370(7) . ? C2 H2 0.9500 . ? C3 C4 1.390(8) . ? C3 H3 0.9500 . ? C4 C5 1.364(9) . ? C4 H4 0.9500 . ? C5 C6 1.394(7) . ? C5 H5 0.9500 . ? C6 C7 1.439(8) . ? C7 H7 0.9500 . ? C8 C9 1.497(8) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.453(8) . ? C10 H10 0.9500 . ? C11 C16 1.381(8) . ? C11 C12 1.402(7) . ? C12 C13 1.418(7) . ? C13 C14 1.352(8) . ? C13 H13 0.9500 . ? C14 C15 1.398(8) . ? C14 H14 0.9500 . ? C15 C16 1.371(8) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.373(8) . ? C17 H17 0.9500 . ? C18 C19 1.365(9) . ? C18 H18 0.9500 . ? C19 C20 1.373(9) . ? C19 H19 0.9500 . ? C20 C21 1.369(12) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 U1 O1 177.3(2) . . ? O2 U1 O4 89.88(17) . . ? O1 U1 O4 91.40(16) . . ? O2 U1 O3 88.93(15) . . ? O1 U1 O3 91.04(17) . . ? O4 U1 O3 152.41(18) . . ? O2 U1 N2 88.53(19) . . ? O1 U1 N2 89.63(17) . . ? O4 U1 N2 71.02(16) . . ? O3 U1 N2 136.48(17) . . ? O2 U1 N1 92.44(18) . . ? O1 U1 N1 84.99(16) . . ? O4 U1 N1 136.74(18) . . ? O3 U1 N1 70.85(14) . . ? N2 U1 N1 65.87(16) . . ? O2 U1 N3 95.61(18) . . ? O1 U1 N3 87.02(18) . . ? O4 U1 N3 75.93(17) . . ? O3 U1 N3 76.76(16) . . ? N2 U1 N3 146.68(16) . . ? N1 U1 N3 146.42(15) . . ? C1 O3 U1 135.3(3) . . ? C12 O4 U1 137.4(4) . . ? C7 N1 C8 118.6(4) . . ? C7 N1 U1 124.1(4) . . ? C8 N1 U1 116.1(3) . . ? C10 N2 C9 117.5(5) . . ? C10 N2 U1 127.3(4) . . ? C9 N2 U1 115.1(3) . . ? C17 N3 C21 116.1(6) . . ? C17 N3 U1 124.2(4) . . ? C21 N3 U1 119.2(4) . . ? O3 C1 C2 121.2(5) . . ? O3 C1 C6 121.2(5) . . ? C2 C1 C6 117.5(5) . . ? C3 C2 C1 121.9(5) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C2 C3 C4 120.3(5) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 119.0(5) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 121.9(6) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C5 C6 C1 119.3(6) . . ? C5 C6 C7 118.1(6) . . ? C1 C6 C7 122.1(5) . . ? N1 C7 C6 128.5(5) . . ? N1 C7 H7 115.7 . . ? C6 C7 H7 115.7 . . ? N1 C8 C9 107.9(4) . . ? N1 C8 H8A 110.1 . . ? C9 C8 H8A 110.1 . . ? N1 C8 H8B 110.1 . . ? C9 C8 H8B 110.1 . . ? H8A C8 H8B 108.4 . . ? N2 C9 C8 109.2(5) . . ? N2 C9 H9A 109.8 . . ? C8 C9 H9A 109.8 . . ? N2 C9 H9B 109.8 . . ? C8 C9 H9B 109.8 . . ? H9A C9 H9B 108.3 . . ? N2 C10 C11 128.2(5) . . ? N2 C10 H10 115.9 . . ? C11 C10 H10 115.9 . . ? C16 C11 C12 119.6(5) . . ? C16 C11 C10 118.4(5) . . ? C12 C11 C10 121.9(5) . . ? O4 C12 C11 122.1(5) . . ? O4 C12 C13 120.3(5) . . ? C11 C12 C13 117.4(6) . . ? C14 C13 C12 121.2(6) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 121.4(6) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C16 C15 C14 117.6(6) . . ? C16 C15 H15 121.2 . . ? C14 C15 H15 121.2 . . ? C15 C16 C11 122.8(5) . . ? C15 C16 H16 118.6 . . ? C11 C16 H16 118.6 . . ? N3 C17 C18 124.1(6) . . ? N3 C17 H17 117.9 . . ? C18 C17 H17 117.9 . . ? C19 C18 C17 118.3(6) . . ? C19 C18 H18 120.9 . . ? C17 C18 H18 120.9 . . ? C18 C19 C20 119.6(7) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C21 C20 C19 118.5(7) . . ? C21 C20 H20 120.8 . . ? C19 C20 H20 120.8 . . ? N3 C21 C20 123.5(7) . . ? N3 C21 H21 118.3 . . ? C20 C21 H21 118.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 U1 O3 C1 -139.8(5) . . . . ? O1 U1 O3 C1 37.5(5) . . . . ? O4 U1 O3 C1 132.5(5) . . . . ? N2 U1 O3 C1 -53.1(6) . . . . ? N1 U1 O3 C1 -46.8(5) . . . . ? N3 U1 O3 C1 124.2(5) . . . . ? O2 U1 O4 C12 47.5(5) . . . . ? O1 U1 O4 C12 -130.1(5) . . . . ? O3 U1 O4 C12 135.0(5) . . . . ? N2 U1 O4 C12 -41.0(5) . . . . ? N1 U1 O4 C12 -45.9(6) . . . . ? N3 U1 O4 C12 143.3(5) . . . . ? O2 U1 N1 C7 120.4(4) . . . . ? O1 U1 N1 C7 -60.4(4) . . . . ? O4 U1 N1 C7 -147.1(4) . . . . ? O3 U1 N1 C7 32.4(4) . . . . ? N2 U1 N1 C7 -152.3(5) . . . . ? N3 U1 N1 C7 16.5(6) . . . . ? O2 U1 N1 C8 -72.3(4) . . . . ? O1 U1 N1 C8 106.9(4) . . . . ? O4 U1 N1 C8 20.1(5) . . . . ? O3 U1 N1 C8 -160.3(4) . . . . ? N2 U1 N1 C8 15.0(4) . . . . ? N3 U1 N1 C8 -176.2(3) . . . . ? O2 U1 N2 C10 -67.0(5) . . . . ? O1 U1 N2 C10 115.0(5) . . . . ? O4 U1 N2 C10 23.4(5) . . . . ? O3 U1 N2 C10 -153.9(4) . . . . ? N1 U1 N2 C10 -160.4(5) . . . . ? N3 U1 N2 C10 31.0(7) . . . . ? O2 U1 N2 C9 109.6(4) . . . . ? O1 U1 N2 C9 -68.4(4) . . . . ? O4 U1 N2 C9 -160.0(4) . . . . ? O3 U1 N2 C9 22.7(5) . . . . ? N1 U1 N2 C9 16.3(4) . . . . ? N3 U1 N2 C9 -152.4(4) . . . . ? O2 U1 N3 C17 64.9(4) . . . . ? O1 U1 N3 C17 -115.7(4) . . . . ? O4 U1 N3 C17 -23.5(4) . . . . ? O3 U1 N3 C17 152.5(5) . . . . ? N2 U1 N3 C17 -31.0(6) . . . . ? N1 U1 N3 C17 167.9(4) . . . . ? O2 U1 N3 C21 -123.2(4) . . . . ? O1 U1 N3 C21 56.2(5) . . . . ? O4 U1 N3 C21 148.4(5) . . . . ? O3 U1 N3 C21 -35.6(4) . . . . ? N2 U1 N3 C21 140.9(4) . . . . ? N1 U1 N3 C21 -20.2(6) . . . . ? U1 O3 C1 C2 -145.4(4) . . . . ? U1 O3 C1 C6 37.5(8) . . . . ? O3 C1 C2 C3 -177.6(5) . . . . ? C6 C1 C2 C3 -0.4(7) . . . . ? C1 C2 C3 C4 -1.9(8) . . . . ? C2 C3 C4 C5 2.7(10) . . . . ? C3 C4 C5 C6 -1.2(10) . . . . ? C4 C5 C6 C1 -1.0(9) . . . . ? C4 C5 C6 C7 170.7(6) . . . . ? O3 C1 C6 C5 179.0(5) . . . . ? C2 C1 C6 C5 1.8(8) . . . . ? O3 C1 C6 C7 7.6(8) . . . . ? C2 C1 C6 C7 -169.6(5) . . . . ? C8 N1 C7 C6 177.7(5) . . . . ? U1 N1 C7 C6 -15.3(8) . . . . ? C5 C6 C7 N1 174.4(5) . . . . ? C1 C6 C7 N1 -14.1(9) . . . . ? C7 N1 C8 C9 125.0(5) . . . . ? U1 N1 C8 C9 -43.1(5) . . . . ? C10 N2 C9 C8 132.1(5) . . . . ? U1 N2 C9 C8 -44.9(5) . . . . ? N1 C8 C9 N2 56.6(5) . . . . ? C9 N2 C10 C11 174.7(5) . . . . ? U1 N2 C10 C11 -8.8(8) . . . . ? N2 C10 C11 C16 172.7(6) . . . . ? N2 C10 C11 C12 -9.8(9) . . . . ? U1 O4 C12 C11 39.0(8) . . . . ? U1 O4 C12 C13 -146.0(4) . . . . ? C16 C11 C12 O4 176.4(5) . . . . ? C10 C11 C12 O4 -1.0(8) . . . . ? C16 C11 C12 C13 1.3(8) . . . . ? C10 C11 C12 C13 -176.1(5) . . . . ? O4 C12 C13 C14 -176.2(5) . . . . ? C11 C12 C13 C14 -1.0(8) . . . . ? C12 C13 C14 C15 0.3(10) . . . . ? C13 C14 C15 C16 0.1(10) . . . . ? C14 C15 C16 C11 0.2(10) . . . . ? C12 C11 C16 C15 -0.9(9) . . . . ? C10 C11 C16 C15 176.6(5) . . . . ? C21 N3 C17 C18 0.0(8) . . . . ? U1 N3 C17 C18 172.1(4) . . . . ? N3 C17 C18 C19 -0.2(8) . . . . ? C17 C18 C19 C20 0.1(8) . . . . ? C18 C19 C20 C21 0.2(9) . . . . ? C17 N3 C21 C20 0.4(9) . . . . ? U1 N3 C21 C20 -172.2(5) . . . . ? C19 C20 C21 N3 -0.4(10) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.28 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.146 _refine_diff_density_min -0.605 _refine_diff_density_rms 0.110 # Attachment 'Salen.cif' data_p-1_salen _database_code_depnum_ccdc_archive 'CCDC 656875' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H32 N4 O4' _chemical_formula_weight 536.62 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #_symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.0089(9) _cell_length_b 7.4921(11) _cell_length_c 30.372(5) _cell_angle_alpha 90.000(3) _cell_angle_beta 93.286(3) _cell_angle_gamma 90.000(3) _cell_volume 1365.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2273 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SHELXPREP-97 (Sheldrick, 1997)' _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 'Bruker APEX' _diffrn_measurement_method 'w/ scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9409 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 23.29 _reflns_number_total 3942 _reflns_number_gt 2273 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART, SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ATOMS v6.1 (Shape Software, 2004)' _computing_publication_material 'SHELXCIF-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0597P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0038(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3942 _refine_ls_number_parameters 362 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1137 _refine_ls_wR_factor_gt 0.1029 _refine_ls_goodness_of_fit_ref 0.867 _refine_ls_restrained_S_all 0.866 _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 0.2922(3) 0.6050(2) 0.20623(5) 0.0365(4) Uani 1 1 d . . . N2 N 0.7108(3) 0.6978(2) 0.29774(6) 0.0378(4) Uani 1 1 d . . . N3 N -0.2111(3) 0.1978(2) 0.20223(5) 0.0375(4) Uani 1 1 d . . . N4 N 0.2074(3) 0.10499(19) 0.29387(5) 0.0368(4) Uani 1 1 d . . . O1 O -0.0970(2) 0.72164(19) 0.17728(5) 0.0505(4) Uani 1 1 d . . . H1 H 0.0025 0.6927 0.1955 0.076 Uiso 1 1 calc R . . O2 O 1.1001(2) 0.57602(18) 0.32457(4) 0.0486(4) Uani 1 1 d . . . H2 H 0.9995 0.6079 0.3069 0.073 Uiso 1 1 calc R . . O3 O -0.6000(2) 0.07626(18) 0.17535(4) 0.0491(4) Uani 1 1 d . . . H3 H -0.5000 0.1085 0.1931 0.074 Uiso 1 1 calc R . . O4 O 0.5976(2) 0.22194(18) 0.32281(5) 0.0503(4) Uani 1 1 d . . . H4 H 0.4986 0.1924 0.3046 0.075 Uiso 1 1 calc R . . C1 C -0.0317(3) 0.6888(2) 0.13635(7) 0.0367(5) Uani 1 1 d D . . C2 C -0.1759(4) 0.7281(3) 0.10054(8) 0.0470(6) Uani 1 1 d D . . H2A H -0.3148 0.7776 0.1049 0.056 Uiso 1 1 calc R . . C3 C -0.1138(4) 0.6939(3) 0.05841(8) 0.0539(6) Uani 1 1 d D . . H3A H -0.2108 0.7221 0.0345 0.065 Uiso 1 1 calc R . . C4 C 0.0911(4) 0.6182(3) 0.05121(7) 0.0522(6) Uani 1 1 d D . . H4A H 0.1310 0.5937 0.0227 0.063 Uiso 1 1 calc R . . C5 C 0.2346(4) 0.5797(3) 0.08675(7) 0.0442(5) Uani 1 1 d D . . H5 H 0.3727 0.5296 0.0820 0.053 Uiso 1 1 calc R . . C6 C 0.1787(3) 0.6137(2) 0.12954(6) 0.0333(5) Uani 1 1 d D . . C7 C 0.3368(3) 0.5768(2) 0.16649(7) 0.0357(5) Uani 1 1 d D . . H7 H 0.4759 0.5307 0.1608 0.043 Uiso 1 1 calc R . . C8 C 0.4632(3) 0.5662(3) 0.24087(6) 0.0408(5) Uani 1 1 d . . . H8A H 0.5897 0.5092 0.2282 0.049 Uiso 1 1 calc R . . H8B H 0.4043 0.4848 0.2622 0.049 Uiso 1 1 calc R . . C9 C 0.5372(3) 0.7366(3) 0.26357(6) 0.0417(5) Uani 1 1 d . . . H9A H 0.5940 0.8187 0.2422 0.050 Uiso 1 1 calc R . . H9B H 0.4113 0.7926 0.2766 0.050 Uiso 1 1 calc R . . C10 C 0.6710(3) 0.7251(2) 0.33780(7) 0.0369(5) Uani 1 1 d D . . H10 H 0.5332 0.7715 0.3443 0.044 Uiso 1 1 calc R . . C11 C 0.8333(3) 0.6862(2) 0.37395(6) 0.0330(5) Uani 1 1 d D . . C12 C 0.7842(3) 0.7185(3) 0.41734(7) 0.0414(5) Uani 1 1 d D . . H12 H 0.6475 0.7690 0.4231 0.050 Uiso 1 1 calc R . . C13 C 0.9318(4) 0.6778(3) 0.45202(7) 0.0477(6) Uani 1 1 d D . . H13 H 0.8967 0.7014 0.4809 0.057 Uiso 1 1 calc R . . C14 C 1.1355(4) 0.6003(3) 0.44319(7) 0.0454(6) Uani 1 1 d D . . H14 H 1.2357 0.5703 0.4665 0.054 Uiso 1 1 calc R . . C15 C 1.1905(3) 0.5678(2) 0.40086(7) 0.0405(5) Uani 1 1 d D . . H15 H 1.3281 0.5180 0.3956 0.049 Uiso 1 1 calc R . . C16 C 1.0415(3) 0.6090(2) 0.36586(6) 0.0345(5) Uani 1 1 d D . . C17 C -0.5409(3) 0.1095(2) 0.13425(6) 0.0343(5) Uani 1 1 d D . . C18 C -0.6896(3) 0.0678(2) 0.09907(7) 0.0403(5) Uani 1 1 d D . . H18 H -0.8268 0.0173 0.1044 0.048 Uiso 1 1 calc R . . C19 C -0.6363(4) 0.1003(3) 0.05676(7) 0.0465(6) Uani 1 1 d D . . H19 H -0.7370 0.0705 0.0335 0.056 Uiso 1 1 calc R . . C20 C -0.4326(4) 0.1776(3) 0.04791(7) 0.0477(6) Uani 1 1 d D . . H20 H -0.3975 0.2011 0.0190 0.057 Uiso 1 1 calc R . . C21 C -0.2840(3) 0.2186(3) 0.08280(7) 0.0423(5) Uani 1 1 d D . . H21 H -0.1473 0.2694 0.0771 0.051 Uiso 1 1 calc R . . C22 C -0.3334(3) 0.1861(2) 0.12601(6) 0.0331(5) Uani 1 1 d D . . C23 C -0.1709(3) 0.2255(2) 0.16225(7) 0.0357(5) Uani 1 1 d D . . H23 H -0.0332 0.2726 0.1558 0.043 Uiso 1 1 calc R . . C24 C -0.0371(3) 0.2361(3) 0.23644(6) 0.0413(5) Uani 1 1 d . . . H24A H -0.0937 0.3183 0.2578 0.050 Uiso 1 1 calc R . . H24B H 0.0888 0.2920 0.2233 0.050 Uiso 1 1 calc R . . C25 C 0.0366(3) 0.0667(3) 0.25905(6) 0.0404(5) Uani 1 1 d . . . H25A H -0.0900 0.0096 0.2716 0.048 Uiso 1 1 calc R . . H25B H 0.0959 -0.0145 0.2378 0.048 Uiso 1 1 calc R . . C26 C 0.1630(3) 0.0764(2) 0.33340(7) 0.0352(5) Uani 1 1 d D . . H26 H 0.0243 0.0293 0.3390 0.042 Uiso 1 1 calc R . . C27 C 0.3208(3) 0.1142(2) 0.37064(6) 0.0338(5) Uani 1 1 d D . . C28 C 0.2654(3) 0.0799(3) 0.41325(7) 0.0437(5) Uani 1 1 d D . . H28 H 0.1273 0.0296 0.4180 0.052 Uiso 1 1 calc R . . C29 C 0.4087(4) 0.1181(3) 0.44882(7) 0.0529(6) Uani 1 1 d D . . H29 H 0.3688 0.0938 0.4773 0.063 Uiso 1 1 calc R . . C30 C 0.6153(4) 0.1939(3) 0.44143(8) 0.0530(6) Uani 1 1 d D . . H30 H 0.7131 0.2214 0.4653 0.064 Uiso 1 1 calc R . . C31 C 0.6760(4) 0.2283(3) 0.39948(8) 0.0461(6) Uani 1 1 d D . . H31 H 0.8144 0.2787 0.3951 0.055 Uiso 1 1 calc R . . C32 C 0.5323(3) 0.1884(2) 0.36348(7) 0.0369(5) Uani 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0347(10) 0.0304(10) 0.0443(11) 0.0008(7) 0.0010(8) -0.0028(7) N2 0.0341(10) 0.0302(10) 0.0487(11) -0.0003(8) -0.0004(8) -0.0026(7) N3 0.0337(10) 0.0318(10) 0.0463(11) -0.0005(8) -0.0027(8) 0.0013(7) N4 0.0342(10) 0.0295(10) 0.0463(11) -0.0009(8) -0.0014(8) 0.0018(7) O1 0.0356(9) 0.0576(10) 0.0580(10) -0.0104(7) 0.0014(7) 0.0062(7) O2 0.0369(8) 0.0611(10) 0.0479(10) -0.0088(7) 0.0038(7) 0.0086(7) O3 0.0373(9) 0.0601(10) 0.0499(10) 0.0070(7) 0.0029(7) -0.0088(7) O4 0.0371(9) 0.0567(10) 0.0571(10) 0.0090(7) 0.0021(7) -0.0072(7) C1 0.0338(12) 0.0266(11) 0.0496(13) -0.0028(9) 0.0010(10) -0.0042(9) C2 0.0353(13) 0.0352(13) 0.0690(16) 0.0030(11) -0.0113(12) -0.0020(10) C3 0.0576(17) 0.0431(14) 0.0584(17) 0.0106(11) -0.0205(13) -0.0148(12) C4 0.0546(16) 0.0565(16) 0.0454(14) 0.0005(10) 0.0017(12) -0.0194(12) C5 0.0405(13) 0.0427(14) 0.0496(14) -0.0056(10) 0.0027(11) -0.0102(10) C6 0.0316(12) 0.0246(11) 0.0435(13) -0.0002(8) 0.0009(9) -0.0049(9) C7 0.0304(11) 0.0252(11) 0.0517(14) -0.0027(9) 0.0025(10) -0.0015(9) C8 0.0392(12) 0.0359(12) 0.0466(13) -0.0007(9) -0.0040(10) 0.0029(10) C9 0.0384(12) 0.0328(12) 0.0529(13) 0.0003(10) -0.0063(10) 0.0002(10) C10 0.0304(11) 0.0258(12) 0.0546(14) -0.0006(9) 0.0043(10) -0.0001(9) C11 0.0310(12) 0.0234(11) 0.0449(13) 0.0011(8) 0.0038(9) -0.0041(9) C12 0.0371(12) 0.0367(13) 0.0510(14) -0.0030(10) 0.0063(10) 0.0001(10) C13 0.0535(15) 0.0463(14) 0.0438(13) -0.0025(10) 0.0069(11) -0.0020(11) C14 0.0484(14) 0.0382(13) 0.0483(14) 0.0033(10) -0.0076(11) -0.0015(11) C15 0.0319(12) 0.0327(13) 0.0562(14) -0.0035(10) -0.0021(11) 0.0021(9) C16 0.0335(12) 0.0270(12) 0.0433(13) -0.0028(9) 0.0042(10) -0.0038(9) C17 0.0338(12) 0.0282(12) 0.0412(12) 0.0042(9) 0.0042(10) 0.0031(9) C18 0.0325(12) 0.0323(12) 0.0553(14) 0.0018(10) -0.0036(10) -0.0019(9) C19 0.0481(14) 0.0397(14) 0.0504(15) -0.0039(10) -0.0087(11) 0.0020(11) C20 0.0552(15) 0.0474(14) 0.0409(13) 0.0016(10) 0.0058(11) 0.0014(11) C21 0.0378(13) 0.0379(13) 0.0516(14) 0.0027(10) 0.0067(10) -0.0001(10) C22 0.0302(11) 0.0243(11) 0.0450(13) 0.0002(9) 0.0035(9) 0.0038(9) C23 0.0302(11) 0.0246(12) 0.0526(14) -0.0002(9) 0.0043(10) -0.0001(9) C24 0.0371(12) 0.0355(13) 0.0505(13) -0.0015(10) -0.0037(10) 0.0000(10) C25 0.0385(12) 0.0345(12) 0.0475(13) -0.0008(9) -0.0038(10) -0.0025(10) C26 0.0304(11) 0.0253(11) 0.0498(14) 0.0021(9) 0.0026(10) 0.0013(9) C27 0.0318(11) 0.0232(11) 0.0462(13) -0.0002(9) 0.0011(10) 0.0047(9) C28 0.0379(13) 0.0414(14) 0.0516(14) 0.0033(10) 0.0013(11) 0.0090(10) C29 0.0569(16) 0.0542(16) 0.0474(14) 0.0003(11) 0.0020(12) 0.0184(13) C30 0.0546(16) 0.0441(15) 0.0578(16) -0.0102(11) -0.0188(13) 0.0133(12) C31 0.0369(13) 0.0333(13) 0.0662(16) -0.0026(10) -0.0124(12) 0.0026(10) C32 0.0338(12) 0.0270(12) 0.0497(13) 0.0023(9) 0.0002(10) 0.0050(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 C7 1.269(2) . ? N1 C8 1.457(2) . ? N2 C10 1.270(2) . ? N2 C9 1.458(2) . ? N3 C23 1.269(2) . ? N3 C24 1.459(2) . ? N4 C26 1.263(2) . ? N4 C25 1.459(2) . ? O1 C1 1.347(2) . ? O1 H1 0.8200 . ? O2 C16 1.345(2) . ? O2 H2 0.8200 . ? O3 C17 1.340(2) . ? O3 H3 0.8200 . ? O4 C32 1.341(2) . ? O4 H4 0.8200 . ? C1 C2 1.383(3) . ? C1 C6 1.410(3) . ? C2 C3 1.377(3) . ? C2 H2A 0.9300 . ? C3 C4 1.384(3) . ? C3 H3A 0.9300 . ? C4 C5 1.373(3) . ? C4 H4A 0.9300 . ? C5 C6 1.384(3) . ? C5 H5 0.9300 . ? C6 C7 1.455(3) . ? C7 H7 0.9300 . ? C8 C9 1.506(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.455(3) . ? C10 H10 0.9300 . ? C11 C12 1.388(3) . ? C11 C16 1.413(3) . ? C12 C13 1.372(3) . ? C12 H12 0.9300 . ? C13 C14 1.394(3) . ? C13 H13 0.9300 . ? C14 C15 1.367(3) . ? C14 H14 0.9300 . ? C15 C16 1.385(3) . ? C15 H15 0.9300 . ? C17 C18 1.388(3) . ? C17 C22 1.408(3) . ? C18 C19 1.364(3) . ? C18 H18 0.9300 . ? C19 C20 1.394(3) . ? C19 H19 0.9300 . ? C20 C21 1.381(3) . ? C20 H20 0.9300 . ? C21 C22 1.384(3) . ? C21 H21 0.9300 . ? C22 C23 1.459(3) . ? C23 H23 0.9300 . ? C24 C25 1.498(3) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.461(3) . ? C26 H26 0.9300 . ? C27 C28 1.379(3) . ? C27 C32 1.416(3) . ? C28 C29 1.373(3) . ? C28 H28 0.9300 . ? C29 C30 1.395(3) . ? C29 H29 0.9300 . ? C30 C31 1.370(3) . ? C30 H30 0.9300 . ? C31 C32 1.386(3) . ? C31 H31 0.9300 . ? 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 C7 N1 C8 118.35(17) . . ? C10 N2 C9 118.94(17) . . ? C23 N3 C24 118.76(17) . . ? C26 N4 C25 118.51(17) . . ? C1 O1 H1 109.5 . . ? C16 O2 H2 109.5 . . ? C17 O3 H3 109.5 . . ? C32 O4 H4 109.5 . . ? O1 C1 C2 118.96(19) . . ? O1 C1 C6 121.28(17) . . ? C2 C1 C6 119.8(2) . . ? C3 C2 C1 120.0(2) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C2 C3 C4 120.91(19) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? C5 C4 C3 119.1(2) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? C4 C5 C6 121.6(2) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C5 C6 C1 118.61(18) . . ? C5 C6 C7 120.43(18) . . ? C1 C6 C7 120.94(18) . . ? N1 C7 C6 122.55(18) . . ? N1 C7 H7 118.7 . . ? C6 C7 H7 118.7 . . ? N1 C8 C9 109.79(15) . . ? N1 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? N1 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? N2 C9 C8 109.70(15) . . ? N2 C9 H9A 109.7 . . ? C8 C9 H9A 109.7 . . ? N2 C9 H9B 109.7 . . ? C8 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? N2 C10 C11 122.40(18) . . ? N2 C10 H10 118.8 . . ? C11 C10 H10 118.8 . . ? C12 C11 C16 118.34(17) . . ? C12 C11 C10 120.79(18) . . ? C16 C11 C10 120.83(18) . . ? C13 C12 C11 121.8(2) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C12 C13 C14 118.7(2) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C15 C14 C13 121.13(19) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C16 120.12(19) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? O2 C16 C15 118.87(18) . . ? O2 C16 C11 121.28(16) . . ? C15 C16 C11 119.85(19) . . ? O3 C17 C18 118.81(18) . . ? O3 C17 C22 121.73(17) . . ? C18 C17 C22 119.47(18) . . ? C19 C18 C17 120.64(19) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C20 120.80(19) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C21 C20 C19 118.7(2) . . ? C21 C20 H20 120.6 . . ? C19 C20 H20 120.6 . . ? C20 C21 C22 121.6(2) . . ? C20 C21 H21 119.2 . . ? C22 C21 H21 119.2 . . ? C21 C22 C17 118.74(18) . . ? C21 C22 C23 120.60(18) . . ? C17 C22 C23 120.64(18) . . ? N3 C23 C22 122.19(18) . . ? N3 C23 H23 118.9 . . ? C22 C23 H23 118.9 . . ? N3 C24 C25 109.90(15) . . ? N3 C24 H24A 109.7 . . ? C25 C24 H24A 109.7 . . ? N3 C24 H24B 109.7 . . ? C25 C24 H24B 109.7 . . ? H24A C24 H24B 108.2 . . ? N4 C25 C24 110.06(15) . . ? N4 C25 H25A 109.6 . . ? C24 C25 H25A 109.6 . . ? N4 C25 H25B 109.6 . . ? C24 C25 H25B 109.6 . . ? H25A C25 H25B 108.2 . . ? N4 C26 C27 122.67(18) . . ? N4 C26 H26 118.7 . . ? C27 C26 H26 118.7 . . ? C28 C27 C32 118.99(18) . . ? C28 C27 C26 120.63(18) . . ? C32 C27 C26 120.37(18) . . ? C29 C28 C27 121.7(2) . . ? C29 C28 H28 119.1 . . ? C27 C28 H28 119.1 . . ? C28 C29 C30 118.8(2) . . ? C28 C29 H29 120.6 . . ? C30 C29 H29 120.6 . . ? C31 C30 C29 120.9(2) . . ? C31 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? C30 C31 C32 120.4(2) . . ? C30 C31 H31 119.8 . . ? C32 C31 H31 119.8 . . ? O4 C32 C31 118.97(19) . . ? O4 C32 C27 121.86(17) . . ? C31 C32 C27 119.2(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -179.29(17) . . . . ? C6 C1 C2 C3 -0.1(3) . . . . ? C1 C2 C3 C4 0.9(3) . . . . ? C2 C3 C4 C5 -1.0(3) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C4 C5 C6 C7 -178.07(17) . . . . ? O1 C1 C6 C5 178.68(16) . . . . ? C2 C1 C6 C5 -0.5(3) . . . . ? O1 C1 C6 C7 -2.9(3) . . . . ? C2 C1 C6 C7 177.87(16) . . . . ? C8 N1 C7 C6 -179.05(16) . . . . ? C5 C6 C7 N1 -179.62(17) . . . . ? C1 C6 C7 N1 2.0(3) . . . . ? C7 N1 C8 C9 114.5(2) . . . . ? C10 N2 C9 C8 -114.7(2) . . . . ? N1 C8 C9 N2 -179.11(17) . . . . ? C9 N2 C10 C11 178.64(16) . . . . ? N2 C10 C11 C12 179.74(17) . . . . ? N2 C10 C11 C16 -2.5(3) . . . . ? C16 C11 C12 C13 0.2(3) . . . . ? C10 C11 C12 C13 177.92(17) . . . . ? C11 C12 C13 C14 -0.6(3) . . . . ? C12 C13 C14 C15 1.1(3) . . . . ? C13 C14 C15 C16 -1.1(3) . . . . ? C14 C15 C16 O2 179.83(17) . . . . ? C14 C15 C16 C11 0.6(3) . . . . ? C12 C11 C16 O2 -179.33(16) . . . . ? C10 C11 C16 O2 2.9(3) . . . . ? C12 C11 C16 C15 -0.1(3) . . . . ? C10 C11 C16 C15 -177.91(16) . . . . ? O3 C17 C18 C19 179.71(16) . . . . ? C22 C17 C18 C19 0.0(3) . . . . ? C17 C18 C19 C20 -0.6(3) . . . . ? C18 C19 C20 C21 0.9(3) . . . . ? C19 C20 C21 C22 -0.5(3) . . . . ? C20 C21 C22 C17 -0.1(3) . . . . ? C20 C21 C22 C23 178.09(18) . . . . ? O3 C17 C22 C21 -179.33(16) . . . . ? C18 C17 C22 C21 0.3(3) . . . . ? O3 C17 C22 C23 2.5(3) . . . . ? C18 C17 C22 C23 -177.85(16) . . . . ? C24 N3 C23 C22 178.29(16) . . . . ? C21 C22 C23 N3 179.81(17) . . . . ? C17 C22 C23 N3 -2.0(3) . . . . ? C23 N3 C24 C25 -114.8(2) . . . . ? C26 N4 C25 C24 114.54(19) . . . . ? N3 C24 C25 N4 -178.87(16) . . . . ? C25 N4 C26 C27 -178.56(15) . . . . ? N4 C26 C27 C28 -179.66(17) . . . . ? N4 C26 C27 C32 1.0(3) . . . . ? C32 C27 C28 C29 0.9(3) . . . . ? C26 C27 C28 C29 -178.47(17) . . . . ? C27 C28 C29 C30 0.1(3) . . . . ? C28 C29 C30 C31 -0.6(3) . . . . ? C29 C30 C31 C32 0.1(3) . . . . ? C30 C31 C32 O4 -179.29(17) . . . . ? C30 C31 C32 C27 0.9(3) . . . . ? C28 C27 C32 O4 178.82(16) . . . . ? C26 C27 C32 O4 -1.8(3) . . . . ? C28 C27 C32 C31 -1.4(3) . . . . ? C26 C27 C32 C31 177.95(16) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.181 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.044