# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email zhangj@ecust.edu.cn _publ_contact_author_name 'Jun Zhang' loop_ _publ_author_name 'Jun Zhang' 'Xiaolong Su' 'Jun Fu' 'Min Shi' # Attachment 'web_deposit_cif_file_1_JunZhang_1314601021.a10707a.cif' data_a10707a _database_code_depnum_ccdc_archive 'CCDC 841928' #TrackingRef 'web_deposit_cif_file_1_JunZhang_1314601021.a10707a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H33 F3 N2 O3 S' _chemical_formula_weight 546.63 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.521(3) _cell_length_b 14.946(6) _cell_length_c 22.415(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2855(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 864 _cell_measurement_theta_min 2.272 _cell_measurement_theta_max 20.661 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.165 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9369 _exptl_absorpt_correction_T_max 0.9599 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 6.75 _diffrn_reflns_number 11878 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_sigmaI/netI 0.0717 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5023 _reflns_number_gt 3215 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1336P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(18) _refine_ls_number_reflns 5023 _refine_ls_number_parameters 352 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1151 _refine_ls_R_factor_gt 0.0774 _refine_ls_wR_factor_ref 0.2232 _refine_ls_wR_factor_gt 0.1995 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 1.030 _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 S1 S 0.38075(19) 0.65055(9) 0.19696(7) 0.0670(5) Uani 1 1 d . . . N1 N 0.1451(5) 0.9726(2) 0.24411(16) 0.0418(9) Uani 1 1 d . . . N2 N 0.1341(5) 0.9882(2) 0.34071(16) 0.0426(9) Uani 1 1 d . . . O1 O 0.5009(9) 0.5932(5) 0.1927(3) 0.166(3) Uani 1 1 d . . . O2 O 0.4256(12) 0.7216(4) 0.2375(3) 0.166(3) Uani 1 1 d . . . O3 O 0.2334(7) 0.6209(5) 0.2073(3) 0.161(3) Uani 1 1 d . . . F1 F 0.5047(7) 0.7346(4) 0.1068(3) 0.161(3) Uani 1 1 d . . . F2 F 0.3158(15) 0.6664(7) 0.0879(3) 0.287(6) Uani 1 1 d U . . F3 F 0.2988(11) 0.7793(6) 0.1307(4) 0.233(5) Uani 1 1 d . . . C1 C 0.0701(6) 1.0077(3) 0.2891(2) 0.0432(11) Uani 1 1 d . . . C2 C 0.2787(6) 0.9346(3) 0.3327(2) 0.0497(13) Uani 1 1 d . . . H2 H 0.3697 0.9711 0.3437 0.060 Uiso 1 1 calc R . . C3 C 0.2795(6) 0.9199(4) 0.2648(2) 0.0501(13) Uani 1 1 d . . . H3A H 0.3765 0.9414 0.2472 0.060 Uiso 1 1 calc R . . H3B H 0.2665 0.8571 0.2552 0.060 Uiso 1 1 calc R . . C4 C 0.0949(6) 0.9727(3) 0.18206(18) 0.0438(11) Uani 1 1 d . . . C5 C 0.1757(6) 1.0293(3) 0.1429(2) 0.0490(13) Uani 1 1 d . . . C6 C 0.1346(8) 1.0227(4) 0.0831(2) 0.0630(15) Uani 1 1 d . . . H6 H 0.1873 1.0573 0.0551 0.076 Uiso 1 1 calc R . . C7 C 0.0180(9) 0.9660(5) 0.0647(3) 0.0777(19) Uani 1 1 d . . . H7 H -0.0064 0.9624 0.0243 0.093 Uiso 1 1 calc R . . C8 C -0.0633(8) 0.9145(4) 0.1046(3) 0.0710(17) Uani 1 1 d . . . H8 H -0.1457 0.8788 0.0915 0.085 Uiso 1 1 calc R . . C9 C -0.0233(7) 0.9154(3) 0.1650(2) 0.0548(13) Uani 1 1 d . . . C10 C 0.3049(7) 1.0918(3) 0.1620(2) 0.0572(14) Uani 1 1 d . . . H10 H 0.3122 1.0886 0.2056 0.069 Uiso 1 1 calc R . . C11 C 0.4605(9) 1.0635(6) 0.1371(3) 0.093(2) Uani 1 1 d . . . H11A H 0.4755 1.0007 0.1441 0.140 Uiso 1 1 calc R . . H11B H 0.5428 1.0966 0.1564 0.140 Uiso 1 1 calc R . . H11C H 0.4629 1.0750 0.0950 0.140 Uiso 1 1 calc R . . C12 C 0.2680(12) 1.1882(4) 0.1457(4) 0.108(3) Uani 1 1 d . . . H12A H 0.2700 1.1948 0.1031 0.163 Uiso 1 1 calc R . . H12B H 0.3450 1.2270 0.1632 0.163 Uiso 1 1 calc R . . H12C H 0.1658 1.2037 0.1604 0.163 Uiso 1 1 calc R . . C13 C -0.1127(7) 0.8552(3) 0.2088(3) 0.0630(14) Uani 1 1 d . . . H13 H -0.0573 0.8571 0.2471 0.076 Uiso 1 1 calc R . . C14 C -0.2759(9) 0.8891(5) 0.2190(4) 0.092(2) Uani 1 1 d . . . H14A H -0.2719 0.9512 0.2299 0.137 Uiso 1 1 calc R . . H14B H -0.3243 0.8555 0.2505 0.137 Uiso 1 1 calc R . . H14C H -0.3361 0.8825 0.1831 0.137 Uiso 1 1 calc R . . C15 C -0.1131(9) 0.7577(4) 0.1874(4) 0.096(2) Uani 1 1 d . . . H15A H -0.1762 0.7527 0.1521 0.144 Uiso 1 1 calc R . . H15B H -0.1557 0.7201 0.2181 0.144 Uiso 1 1 calc R . . H15C H -0.0076 0.7393 0.1787 0.144 Uiso 1 1 calc R . . C16 C 0.0864(7) 1.0246(3) 0.39745(19) 0.0495(13) Uani 1 1 d . . . C17 C -0.0501(7) 0.9945(3) 0.4241(2) 0.0584(15) Uani 1 1 d . . . C18 C -0.0857(9) 1.0322(5) 0.4788(3) 0.0789(19) Uani 1 1 d . . . H18 H -0.1776 1.0148 0.4980 0.095 Uiso 1 1 calc R . . C19 C 0.0097(12) 1.0944(5) 0.5058(3) 0.095(3) Uani 1 1 d . . . H19 H -0.0171 1.1169 0.5431 0.114 Uiso 1 1 calc R . . C20 C 0.1429(11) 1.1234(4) 0.4784(3) 0.086(2) Uani 1 1 d . . . H20 H 0.2052 1.1669 0.4963 0.103 Uiso 1 1 calc R . . C21 C 0.1851(8) 1.0873(4) 0.4235(2) 0.0671(17) Uani 1 1 d . . . H21 H 0.2773 1.1049 0.4047 0.081 Uiso 1 1 calc R . . C22 C -0.1529(9) 0.9260(5) 0.3970(3) 0.091(2) Uani 1 1 d . . . H22A H -0.2155 0.8985 0.4275 0.136 Uiso 1 1 calc R . . H22B H -0.0897 0.8813 0.3778 0.136 Uiso 1 1 calc R . . H22C H -0.2203 0.9537 0.3681 0.136 Uiso 1 1 calc R . . C23 C 0.2755(6) 0.8515(4) 0.3715(2) 0.0501(13) Uani 1 1 d . . . C24 C 0.1927(8) 0.7769(4) 0.3565(3) 0.082(2) Uani 1 1 d . . . H24 H 0.1403 0.7749 0.3201 0.098 Uiso 1 1 calc R . . C25 C 0.1853(10) 0.7048(5) 0.3943(4) 0.103(3) Uani 1 1 d . . . H25 H 0.1245 0.6553 0.3843 0.124 Uiso 1 1 calc R . . C26 C 0.2668(14) 0.7060(6) 0.4459(4) 0.120(4) Uani 1 1 d . . . H26 H 0.2647 0.6564 0.4710 0.144 Uiso 1 1 calc R . . C27 C 0.3520(16) 0.7794(6) 0.4615(3) 0.127(4) Uani 1 1 d . . . H27 H 0.4047 0.7806 0.4978 0.153 Uiso 1 1 calc R . . C28 C 0.3609(9) 0.8519(5) 0.4238(3) 0.081(2) Uani 1 1 d . . . H28 H 0.4237 0.9007 0.4335 0.098 Uiso 1 1 calc R . . C29 C 0.3723(11) 0.7071(6) 0.1271(4) 0.094(2) Uani 1 1 d . . . H1 H -0.025(6) 1.040(3) 0.2863(18) 0.035(12) Uiso 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 S1 0.0577(9) 0.0526(7) 0.0906(11) 0.0182(7) 0.0059(9) 0.0057(7) N1 0.043(3) 0.0399(19) 0.042(2) 0.0008(16) 0.0038(18) 0.001(2) N2 0.049(2) 0.0411(19) 0.038(2) 0.0022(15) 0.0010(18) 0.001(2) O1 0.192(7) 0.171(6) 0.135(5) 0.058(5) 0.066(5) 0.113(6) O2 0.256(10) 0.118(4) 0.125(5) -0.028(4) 0.019(6) -0.038(6) O3 0.077(4) 0.233(8) 0.173(6) 0.122(6) -0.023(4) -0.060(5) F1 0.107(4) 0.200(6) 0.177(5) 0.107(5) 0.056(4) 0.015(4) F2 0.443(13) 0.319(9) 0.101(4) 0.053(5) -0.108(6) -0.248(10) F3 0.260(10) 0.228(8) 0.212(7) 0.136(7) 0.085(7) 0.146(8) C1 0.045(3) 0.035(2) 0.050(3) 0.003(2) 0.006(2) 0.004(2) C2 0.049(3) 0.052(3) 0.048(3) 0.006(2) -0.002(2) 0.005(2) C3 0.043(3) 0.061(3) 0.046(3) 0.010(2) 0.009(2) 0.014(3) C4 0.048(3) 0.048(2) 0.035(2) -0.003(2) -0.004(2) 0.013(2) C5 0.051(3) 0.056(3) 0.040(3) -0.003(2) -0.006(2) 0.012(3) C6 0.073(4) 0.072(3) 0.044(3) 0.000(3) -0.007(3) 0.010(3) C7 0.095(5) 0.097(5) 0.041(3) -0.014(3) -0.011(3) 0.005(4) C8 0.072(4) 0.071(4) 0.070(4) -0.014(3) -0.021(3) 0.005(3) C9 0.053(3) 0.048(3) 0.063(3) -0.006(2) 0.000(3) 0.000(3) C10 0.076(4) 0.055(3) 0.041(3) 0.006(2) -0.003(3) -0.008(3) C11 0.070(5) 0.129(6) 0.082(4) -0.026(4) 0.022(4) -0.026(4) C12 0.148(8) 0.061(4) 0.116(6) 0.008(4) -0.030(6) -0.008(5) C13 0.050(3) 0.053(3) 0.086(4) -0.005(3) -0.007(3) 0.001(3) C14 0.071(5) 0.083(5) 0.120(6) -0.008(4) 0.022(4) 0.002(4) C15 0.074(5) 0.061(4) 0.153(7) -0.017(4) 0.022(5) -0.013(3) C16 0.063(4) 0.047(3) 0.038(2) 0.005(2) 0.000(2) 0.014(3) C17 0.079(4) 0.053(3) 0.044(3) 0.004(2) 0.016(3) 0.013(3) C18 0.093(5) 0.085(4) 0.059(4) 0.014(3) 0.019(4) 0.011(4) C19 0.144(8) 0.098(5) 0.043(3) -0.010(4) 0.010(4) 0.028(6) C20 0.122(7) 0.073(4) 0.063(4) -0.017(3) -0.014(4) -0.002(4) C21 0.093(5) 0.054(3) 0.054(3) -0.008(3) -0.007(3) 0.005(3) C22 0.085(6) 0.095(5) 0.092(5) -0.016(4) 0.031(4) -0.019(4) C23 0.051(3) 0.058(3) 0.041(3) 0.005(2) 0.008(2) 0.022(3) C24 0.073(5) 0.069(4) 0.103(5) 0.025(4) -0.011(4) 0.002(4) C25 0.106(7) 0.069(4) 0.134(7) 0.042(5) 0.032(6) 0.022(4) C26 0.178(10) 0.090(6) 0.092(6) 0.047(5) 0.055(6) 0.075(7) C27 0.224(13) 0.107(6) 0.051(4) 0.012(4) 0.000(6) 0.063(8) C28 0.104(6) 0.086(4) 0.054(3) 0.000(3) -0.009(4) 0.042(5) C29 0.080(5) 0.095(5) 0.106(6) 0.032(4) -0.018(5) -0.014(5) _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 S1 O1 1.339(6) . ? S1 O3 1.351(6) . ? S1 O2 1.450(6) . ? S1 C29 1.781(8) . ? N1 C1 1.304(6) . ? N1 C4 1.455(6) . ? N1 C3 1.466(6) . ? N2 C1 1.312(6) . ? N2 C16 1.442(6) . ? N2 C2 1.481(6) . ? F1 C29 1.284(9) . ? F2 C29 1.172(10) . ? F3 C29 1.250(10) . ? C2 C23 1.517(7) . ? C2 C3 1.536(7) . ? C4 C9 1.376(7) . ? C4 C5 1.399(7) . ? C5 C6 1.389(7) . ? C5 C10 1.505(7) . ? C6 C7 1.370(9) . ? C7 C8 1.368(9) . ? C8 C9 1.396(8) . ? C9 C13 1.535(8) . ? C10 C11 1.500(9) . ? C10 C12 1.519(8) . ? C13 C14 1.498(9) . ? C13 C15 1.534(8) . ? C16 C17 1.383(8) . ? C16 C21 1.388(8) . ? C17 C18 1.382(8) . ? C17 C22 1.477(9) . ? C18 C19 1.377(11) . ? C19 C20 1.361(11) . ? C20 C21 1.390(9) . ? C23 C24 1.361(9) . ? C23 C28 1.381(8) . ? C24 C25 1.372(9) . ? C25 C26 1.350(13) . ? C26 C27 1.362(14) . ? C27 C28 1.375(10) . ? 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 O1 S1 O3 120.8(5) . . ? O1 S1 O2 108.2(6) . . ? O3 S1 O2 112.2(6) . . ? O1 S1 C29 105.8(4) . . ? O3 S1 C29 105.6(4) . . ? O2 S1 C29 102.4(4) . . ? C1 N1 C4 126.5(4) . . ? C1 N1 C3 110.7(4) . . ? C4 N1 C3 122.3(4) . . ? C1 N2 C16 125.2(4) . . ? C1 N2 C2 111.0(4) . . ? C16 N2 C2 123.1(4) . . ? N1 C1 N2 112.9(5) . . ? N2 C2 C23 111.0(4) . . ? N2 C2 C3 101.6(4) . . ? C23 C2 C3 116.8(4) . . ? N1 C3 C2 103.5(4) . . ? C9 C4 C5 124.2(4) . . ? C9 C4 N1 118.6(4) . . ? C5 C4 N1 117.1(4) . . ? C6 C5 C4 116.0(5) . . ? C6 C5 C10 120.2(5) . . ? C4 C5 C10 123.8(4) . . ? C7 C6 C5 121.2(6) . . ? C8 C7 C6 121.2(5) . . ? C7 C8 C9 120.3(6) . . ? C4 C9 C8 117.0(5) . . ? C4 C9 C13 123.5(5) . . ? C8 C9 C13 119.5(5) . . ? C11 C10 C5 111.5(5) . . ? C11 C10 C12 111.2(6) . . ? C5 C10 C12 111.6(5) . . ? C14 C13 C15 111.6(5) . . ? C14 C13 C9 111.1(5) . . ? C15 C13 C9 111.0(5) . . ? C17 C16 C21 123.2(5) . . ? C17 C16 N2 119.7(5) . . ? C21 C16 N2 117.1(5) . . ? C18 C17 C16 115.8(6) . . ? C18 C17 C22 121.1(6) . . ? C16 C17 C22 123.1(5) . . ? C19 C18 C17 122.4(7) . . ? C20 C19 C18 120.6(6) . . ? C19 C20 C21 119.5(7) . . ? C16 C21 C20 118.5(7) . . ? C24 C23 C28 119.2(6) . . ? C24 C23 C2 122.5(5) . . ? C28 C23 C2 118.3(6) . . ? C23 C24 C25 121.0(7) . . ? C26 C25 C24 119.7(8) . . ? C25 C26 C27 120.3(7) . . ? C26 C27 C28 120.5(8) . . ? C27 C28 C23 119.2(8) . . ? F2 C29 F3 107.0(10) . . ? F2 C29 F1 105.2(10) . . ? F3 C29 F1 100.7(7) . . ? F2 C29 S1 115.5(7) . . ? F3 C29 S1 111.8(7) . . ? F1 C29 S1 115.3(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1 O3 0.94(5) 2.15(5) 3.091(8) 172(4) 3 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.547 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.059 # Attachment 'web_deposit_cif_file_3_JunZhang_1314601021.mo_10727b.cif' data_mo_10727b _database_code_depnum_ccdc_archive 'CCDC 841930' #TrackingRef 'web_deposit_cif_file_3_JunZhang_1314601021.mo_10727b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H31 I N2' _chemical_formula_weight 510.44 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 15.2391(17) _cell_length_b 15.3799(18) _cell_length_c 22.066(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5171.8(10) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9924 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 24.25 _exptl_crystal_description polyhedral _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 1.253 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6682 _exptl_absorpt_correction_T_max 0.7877 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5.76 _diffrn_reflns_number 37272 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 27.50 _reflns_number_total 11769 _reflns_number_gt 8317 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.1094P)^2^+0.2708P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(2) _refine_ls_number_reflns 11769 _refine_ls_number_parameters 561 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1672 _refine_ls_wR_factor_gt 0.1444 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 I1 I 0.10531(3) 0.79529(2) 0.94684(2) 0.09361(18) Uani 1 1 d . . . N1 N 0.3351(2) 0.6082(3) 0.91465(16) 0.0557(9) Uani 1 1 d . . . N2 N 0.2976(2) 0.6145(2) 1.00992(15) 0.0454(7) Uani 1 1 d . . . C1 C 0.2735(3) 0.6262(3) 0.95416(18) 0.0452(8) Uani 1 1 d D . . H1 H 0.223(3) 0.656(4) 0.942(3) 0.10(2) Uiso 1 1 d D . . C2 C 0.3914(3) 0.5835(3) 1.0128(2) 0.0541(10) Uani 1 1 d . . . H2 H 0.4276 0.6289 1.0333 0.065 Uiso 1 1 calc R . . C3 C 0.4162(3) 0.5811(4) 0.9450(2) 0.0665(13) Uani 1 1 d . . . H3A H 0.4648 0.6219 0.9362 0.080 Uiso 1 1 calc R . . H3B H 0.4336 0.5218 0.9325 0.080 Uiso 1 1 calc R . . C4 C 0.3262(3) 0.6179(3) 0.84950(19) 0.0526(10) Uani 1 1 d . . . C5 C 0.3439(3) 0.6974(3) 0.8230(2) 0.0606(11) Uani 1 1 d . . . C6 C 0.3382(4) 0.7031(4) 0.7600(2) 0.0713(13) Uani 1 1 d . . . H6 H 0.3515 0.7567 0.7406 0.086 Uiso 1 1 calc R . . C7 C 0.3137(3) 0.6324(3) 0.7252(2) 0.0600(11) Uani 1 1 d . . . C8 C 0.2946(3) 0.5549(3) 0.7533(2) 0.0624(12) Uani 1 1 d . . . H8 H 0.2760 0.5070 0.7292 0.075 Uiso 1 1 calc R . . C9 C 0.3014(3) 0.5441(3) 0.8159(2) 0.0534(10) Uani 1 1 d . . . C10 C 0.3660(6) 0.7758(4) 0.8609(3) 0.101(2) Uani 1 1 d . . . H10A H 0.3301 0.7756 0.8978 0.151 Uiso 1 1 calc R . . H10B H 0.3540 0.8288 0.8377 0.151 Uiso 1 1 calc R . . H10C H 0.4283 0.7741 0.8720 0.151 Uiso 1 1 calc R . . C11 C 0.3075(5) 0.6403(4) 0.6580(2) 0.0820(17) Uani 1 1 d . . . H11A H 0.3021 0.7017 0.6469 0.123 Uiso 1 1 calc R . . H11B H 0.2559 0.6084 0.6436 0.123 Uiso 1 1 calc R . . H11C H 0.3604 0.6159 0.6394 0.123 Uiso 1 1 calc R . . C12 C 0.2816(4) 0.4582(4) 0.8454(3) 0.0795(15) Uani 1 1 d . . . H12A H 0.3363 0.4318 0.8599 0.119 Uiso 1 1 calc R . . H12B H 0.2536 0.4195 0.8160 0.119 Uiso 1 1 calc R . . H12C H 0.2419 0.4674 0.8798 0.119 Uiso 1 1 calc R . . C13 C 0.2428(2) 0.6284(2) 1.06202(17) 0.0430(8) Uani 1 1 d . . . C14 C 0.1725(3) 0.5723(3) 1.07193(18) 0.0455(8) Uani 1 1 d . . . C15 C 0.1207(3) 0.5858(3) 1.12310(19) 0.0557(10) Uani 1 1 d . . . H15 H 0.0716 0.5492 1.1305 0.067 Uiso 1 1 calc R . . C16 C 0.1404(3) 0.6537(3) 1.1641(2) 0.0570(11) Uani 1 1 d . . . C17 C 0.2105(3) 0.7073(3) 1.15179(19) 0.0544(10) Uani 1 1 d . . . H17 H 0.2242 0.7527 1.1795 0.065 Uiso 1 1 calc R . . C18 C 0.2618(3) 0.6975(3) 1.10044(18) 0.0484(8) Uani 1 1 d . . . C19 C 0.1509(3) 0.4974(3) 1.0304(2) 0.0611(11) Uani 1 1 d . . . H19A H 0.1343 0.5199 0.9905 0.092 Uiso 1 1 calc R . . H19B H 0.1020 0.4640 1.0474 0.092 Uiso 1 1 calc R . . H19C H 0.2024 0.4597 1.0263 0.092 Uiso 1 1 calc R . . C20 C 0.0859(4) 0.6666(4) 1.2202(3) 0.0815(16) Uani 1 1 d . . . H20A H 0.1244 0.6805 1.2544 0.122 Uiso 1 1 calc R . . H20B H 0.0532 0.6132 1.2290 0.122 Uiso 1 1 calc R . . H20C H 0.0446 0.7146 1.2136 0.122 Uiso 1 1 calc R . . C21 C 0.3320(4) 0.7620(3) 1.0859(3) 0.0713(13) Uani 1 1 d . . . H21A H 0.3189 0.8173 1.1060 0.107 Uiso 1 1 calc R . . H21B H 0.3345 0.7710 1.0419 0.107 Uiso 1 1 calc R . . H21C H 0.3887 0.7401 1.1002 0.107 Uiso 1 1 calc R . . C22 C 0.4002(3) 0.4999(3) 1.0470(2) 0.0591(11) Uani 1 1 d . . . C23 C 0.3874(4) 0.4181(4) 1.0222(3) 0.0800(15) Uani 1 1 d . . . H23 H 0.3686 0.4129 0.9813 0.096 Uiso 1 1 calc R . . C24 C 0.4016(5) 0.3447(5) 1.0557(5) 0.109(3) Uani 1 1 d . . . H24 H 0.3932 0.2887 1.0384 0.131 Uiso 1 1 calc R . . C25 C 0.4283(5) 0.3532(7) 1.1155(5) 0.119(3) Uani 1 1 d . . . H25 H 0.4383 0.3025 1.1391 0.143 Uiso 1 1 calc R . . C26 C 0.4404(6) 0.4326(8) 1.1407(4) 0.112(3) Uani 1 1 d . . . H26 H 0.4592 0.4374 1.1816 0.135 Uiso 1 1 calc R . . C27 C 0.4257(4) 0.5046(5) 1.1077(3) 0.0847(18) Uani 1 1 d . . . H27 H 0.4328 0.5600 1.1261 0.102 Uiso 1 1 calc R . . I2 I 0.94203(3) 0.29498(5) 0.10965(3) 0.1286(3) Uani 1 1 d . . . N3 N 0.1954(2) 0.1054(2) -0.05463(17) 0.0534(8) Uani 1 1 d . . . N4 N 0.2643(2) 0.0586(2) 0.02642(16) 0.0463(7) Uani 1 1 d . . . C28 C 0.2651(3) 0.1092(3) -0.0218(2) 0.0496(9) Uani 1 1 d D . . H28 H 0.315(2) 0.144(2) -0.0330(19) 0.047(11) Uiso 1 1 d D . . C29 C 0.1822(3) 0.0040(3) 0.0246(2) 0.0472(9) Uani 1 1 d . . . H29 H 0.1989 -0.0567 0.0133 0.057 Uiso 1 1 calc R . . C30 C 0.1317(3) 0.0442(3) -0.0281(2) 0.0545(10) Uani 1 1 d . . . H30A H 0.1141 -0.0007 -0.0579 0.065 Uiso 1 1 calc R . . H30B H 0.0786 0.0750 -0.0137 0.065 Uiso 1 1 calc R . . C31 C 0.1721(3) 0.1593(3) -0.1058(2) 0.0567(10) Uani 1 1 d . . . C32 C 0.1790(4) 0.1246(4) -0.1639(2) 0.0668(12) Uani 1 1 d . . . C33 C 0.1497(4) 0.1760(4) -0.2115(2) 0.0762(15) Uani 1 1 d . . . H33 H 0.1533 0.1540 -0.2517 0.091 Uiso 1 1 calc R . . C34 C 0.1153(4) 0.2586(4) -0.2024(3) 0.0736(14) Uani 1 1 d . . . C35 C 0.1102(4) 0.2893(3) -0.1453(3) 0.0720(13) Uani 1 1 d . . . H35 H 0.0857 0.3454 -0.1389 0.086 Uiso 1 1 calc R . . C36 C 0.1394(3) 0.2420(3) -0.0953(2) 0.0632(12) Uani 1 1 d . . . C37 C 0.2190(6) 0.0371(5) -0.1741(3) 0.101(2) Uani 1 1 d . . . H37A H 0.2818 0.0395 -0.1647 0.152 Uiso 1 1 calc R . . H37B H 0.2110 0.0201 -0.2165 0.152 Uiso 1 1 calc R . . H37C H 0.1904 -0.0056 -0.1477 0.152 Uiso 1 1 calc R . . C38 C 0.0819(6) 0.3094(7) -0.2559(4) 0.117(3) Uani 1 1 d . . . H38A H 0.0357 0.2761 -0.2763 0.176 Uiso 1 1 calc R . . H38B H 0.1302 0.3199 -0.2843 0.176 Uiso 1 1 calc R . . H38C H 0.0581 0.3651 -0.2420 0.176 Uiso 1 1 calc R . . C39 C 0.1313(6) 0.2775(4) -0.0319(3) 0.097(2) Uani 1 1 d . . . H39A H 0.0894 0.2421 -0.0089 0.145 Uiso 1 1 calc R . . H39B H 0.1104 0.3377 -0.0336 0.145 Uiso 1 1 calc R . . H39C H 0.1887 0.2757 -0.0120 0.145 Uiso 1 1 calc R . . C40 C 0.3397(2) 0.0321(2) 0.06146(19) 0.0447(8) Uani 1 1 d . . . C41 C 0.3984(3) -0.0271(3) 0.0350(2) 0.0504(9) Uani 1 1 d . . . C42 C 0.4658(3) -0.0597(3) 0.0709(2) 0.0602(11) Uani 1 1 d . . . H42 H 0.5054 -0.1008 0.0540 0.072 Uiso 1 1 calc R . . C43 C 0.4768(3) -0.0341(4) 0.1306(3) 0.0665(13) Uani 1 1 d . . . C44 C 0.4197(3) 0.0273(4) 0.1537(2) 0.0640(12) Uani 1 1 d . . . H44 H 0.4282 0.0473 0.1940 0.077 Uiso 1 1 calc R . . C45 C 0.3501(3) 0.0612(3) 0.1202(2) 0.0560(10) Uani 1 1 d . . . C46 C 0.3888(4) -0.0557(4) -0.0293(2) 0.0705(13) Uani 1 1 d . . . H46A H 0.3284 -0.0754 -0.0363 0.106 Uiso 1 1 calc R . . H46B H 0.4295 -0.1035 -0.0375 0.106 Uiso 1 1 calc R . . H46C H 0.4019 -0.0068 -0.0564 0.106 Uiso 1 1 calc R . . C47 C 0.5499(5) -0.0739(6) 0.1682(3) 0.099(2) Uani 1 1 d . . . H47A H 0.5889 -0.1077 0.1419 0.149 Uiso 1 1 calc R . . H47B H 0.5246 -0.1121 0.1991 0.149 Uiso 1 1 calc R . . H47C H 0.5836 -0.0276 0.1879 0.149 Uiso 1 1 calc R . . C48 C 0.2910(4) 0.1299(4) 0.1481(3) 0.0870(18) Uani 1 1 d . . . H48A H 0.2469 0.1018 0.1738 0.131 Uiso 1 1 calc R . . H48B H 0.2616 0.1625 0.1158 0.131 Uiso 1 1 calc R . . H48C H 0.3264 0.1698 0.1726 0.131 Uiso 1 1 calc R . . C49 C 0.1354(3) 0.0013(3) 0.0849(2) 0.0499(9) Uani 1 1 d . . . C50 C 0.0866(3) 0.0720(3) 0.1061(2) 0.0601(11) Uani 1 1 d . . . H50 H 0.0819 0.1231 0.0822 0.072 Uiso 1 1 calc R . . C51 C 0.0455(4) 0.0681(4) 0.1612(3) 0.0720(14) Uani 1 1 d . . . H51 H 0.0131 0.1170 0.1751 0.086 Uiso 1 1 calc R . . C52 C 0.0500(5) -0.0045(4) 0.1964(3) 0.0842(17) Uani 1 1 d . . . H52 H 0.0214 -0.0064 0.2347 0.101 Uiso 1 1 calc R . . C53 C 0.0969(5) -0.0757(4) 0.1756(3) 0.0873(18) Uani 1 1 d . . . H53 H 0.1008 -0.1268 0.1996 0.105 Uiso 1 1 calc R . . C54 C 0.1383(3) -0.0723(3) 0.1197(3) 0.0652(12) Uani 1 1 d . . . H54 H 0.1691 -0.1218 0.1053 0.078 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 I1 0.0630(2) 0.0616(2) 0.1563(4) -0.0296(2) -0.0099(2) 0.01082(16) N1 0.0484(19) 0.076(2) 0.0425(19) -0.0040(17) 0.0060(15) 0.0107(18) N2 0.0352(15) 0.0599(19) 0.0409(18) 0.0008(15) 0.0077(13) 0.0067(14) C1 0.0386(18) 0.051(2) 0.045(2) -0.0047(17) 0.0015(17) 0.0020(16) C2 0.0395(19) 0.070(3) 0.053(2) -0.0069(19) 0.0034(18) 0.0044(19) C3 0.042(2) 0.106(4) 0.052(2) 0.000(3) 0.0049(19) 0.014(2) C4 0.045(2) 0.069(3) 0.044(2) -0.0024(19) 0.0098(17) 0.0063(19) C5 0.068(3) 0.061(3) 0.053(3) -0.009(2) 0.010(2) -0.002(2) C6 0.097(4) 0.063(3) 0.054(3) 0.008(2) 0.014(3) 0.006(3) C7 0.062(3) 0.069(3) 0.049(2) -0.005(2) 0.007(2) 0.019(2) C8 0.063(3) 0.066(3) 0.058(3) -0.018(2) -0.005(2) 0.008(2) C9 0.049(2) 0.056(2) 0.055(3) -0.0030(19) 0.0044(19) 0.0085(18) C10 0.141(7) 0.076(4) 0.085(4) -0.025(3) 0.016(4) -0.040(4) C11 0.098(4) 0.091(4) 0.057(3) -0.005(3) -0.005(3) 0.019(3) C12 0.085(4) 0.070(3) 0.084(4) -0.006(3) 0.008(3) -0.010(3) C13 0.0414(18) 0.0474(19) 0.040(2) 0.0012(15) 0.0076(15) 0.0088(15) C14 0.0424(19) 0.048(2) 0.046(2) 0.0059(16) 0.0009(16) 0.0061(16) C15 0.051(2) 0.066(3) 0.050(2) 0.0140(19) 0.0109(18) 0.0003(19) C16 0.059(2) 0.062(3) 0.050(2) 0.015(2) 0.0120(19) 0.011(2) C17 0.066(2) 0.052(2) 0.045(2) -0.0023(18) 0.0030(19) 0.014(2) C18 0.0476(19) 0.052(2) 0.046(2) 0.0041(17) 0.0065(16) 0.0016(17) C19 0.060(3) 0.062(3) 0.062(3) -0.005(2) -0.005(2) -0.006(2) C20 0.092(4) 0.085(4) 0.068(3) 0.000(3) 0.036(3) 0.001(3) C21 0.072(3) 0.056(3) 0.085(3) -0.005(2) 0.015(3) -0.009(2) C22 0.0378(19) 0.078(3) 0.061(3) 0.003(2) 0.004(2) 0.014(2) C23 0.050(3) 0.087(4) 0.103(4) -0.007(3) 0.000(3) 0.009(3) C24 0.070(4) 0.077(4) 0.180(9) 0.007(5) 0.009(5) 0.008(3) C25 0.069(4) 0.127(7) 0.162(8) 0.075(7) 0.014(5) 0.033(4) C26 0.092(5) 0.160(8) 0.085(4) 0.045(5) 0.001(4) 0.033(6) C27 0.071(3) 0.126(5) 0.056(3) 0.009(3) -0.001(3) 0.026(3) I2 0.0865(3) 0.1747(6) 0.1246(4) 0.0579(4) -0.0089(3) 0.0473(4) N3 0.0491(18) 0.0524(18) 0.059(2) -0.0013(16) 0.0073(16) -0.0104(14) N4 0.0398(16) 0.0428(16) 0.0564(19) -0.0035(14) 0.0011(14) -0.0085(13) C28 0.043(2) 0.047(2) 0.058(2) -0.0090(18) 0.0067(18) -0.0128(17) C29 0.0402(19) 0.0434(19) 0.058(2) -0.0042(17) 0.0039(17) -0.0085(16) C30 0.048(2) 0.057(2) 0.059(3) 0.0057(19) 0.0005(18) -0.0129(19) C31 0.050(2) 0.059(3) 0.061(3) 0.003(2) 0.001(2) -0.0086(19) C32 0.068(3) 0.068(3) 0.064(3) -0.003(2) 0.011(2) 0.004(2) C33 0.081(4) 0.098(4) 0.050(3) 0.004(3) 0.010(2) -0.006(3) C34 0.067(3) 0.087(4) 0.067(3) 0.020(3) 0.012(2) 0.002(3) C35 0.071(3) 0.057(3) 0.088(4) 0.012(2) 0.009(3) -0.003(3) C36 0.062(3) 0.054(2) 0.073(3) 0.006(2) 0.004(2) -0.013(2) C37 0.143(7) 0.087(4) 0.074(4) -0.013(3) 0.021(4) 0.035(4) C38 0.110(5) 0.140(7) 0.102(5) 0.053(5) 0.013(4) 0.029(5) C39 0.157(7) 0.055(3) 0.078(4) -0.020(3) -0.008(4) -0.004(3) C40 0.0383(17) 0.0398(17) 0.056(2) -0.0055(16) 0.0021(17) -0.0076(14) C41 0.0370(18) 0.050(2) 0.064(3) -0.0094(17) 0.0017(18) -0.0113(17) C42 0.047(2) 0.050(2) 0.083(3) -0.004(2) 0.005(2) 0.0003(18) C43 0.045(2) 0.071(3) 0.083(4) -0.002(3) -0.004(2) -0.007(2) C44 0.054(3) 0.074(3) 0.064(3) -0.016(2) -0.007(2) -0.013(2) C45 0.058(2) 0.056(2) 0.054(3) -0.0127(19) 0.007(2) -0.014(2) C46 0.059(3) 0.078(3) 0.075(3) -0.026(3) 0.018(2) -0.004(2) C47 0.082(4) 0.120(5) 0.097(4) 0.003(4) -0.026(4) 0.016(4) C48 0.071(3) 0.083(4) 0.107(5) -0.040(3) -0.004(3) 0.003(3) C49 0.0339(17) 0.050(2) 0.066(3) 0.0029(18) 0.0055(17) -0.0007(15) C50 0.053(2) 0.053(2) 0.075(3) 0.002(2) 0.007(2) 0.0013(19) C51 0.060(3) 0.080(3) 0.076(3) -0.005(3) 0.020(2) 0.013(3) C52 0.080(4) 0.100(4) 0.073(3) 0.008(3) 0.027(3) 0.015(3) C53 0.099(4) 0.083(4) 0.080(4) 0.033(3) 0.027(3) 0.014(3) C54 0.061(3) 0.054(3) 0.081(3) 0.005(2) 0.013(2) 0.009(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 N1 C1 1.312(5) . ? N1 C4 1.452(6) . ? N1 C3 1.465(6) . ? N2 C1 1.297(5) . ? N2 C13 1.437(5) . ? N2 C2 1.508(5) . ? C2 C22 1.497(7) . ? C2 C3 1.542(6) . ? C4 C5 1.381(7) . ? C4 C9 1.408(7) . ? C5 C6 1.396(7) . ? C5 C10 1.505(7) . ? C6 C7 1.383(8) . ? C7 C8 1.375(8) . ? C7 C11 1.491(7) . ? C8 C9 1.395(7) . ? C9 C12 1.504(8) . ? C13 C18 1.389(6) . ? C13 C14 1.393(6) . ? C14 C15 1.394(6) . ? C14 C19 1.508(6) . ? C15 C16 1.414(7) . ? C16 C17 1.377(7) . ? C16 C20 1.503(7) . ? C17 C18 1.385(6) . ? C18 C21 1.495(7) . ? C22 C23 1.387(8) . ? C22 C27 1.398(8) . ? C23 C24 1.367(10) . ? C24 C25 1.386(14) . ? C25 C26 1.355(14) . ? C26 C27 1.344(11) . ? N3 C28 1.287(6) . ? N3 C31 1.445(6) . ? N3 C30 1.475(5) . ? N4 C28 1.317(6) . ? N4 C40 1.444(5) . ? N4 C29 1.508(5) . ? C29 C49 1.510(6) . ? C29 C30 1.526(6) . ? C31 C36 1.386(7) . ? C31 C32 1.392(7) . ? C32 C33 1.390(8) . ? C32 C37 1.494(8) . ? C33 C34 1.389(9) . ? C34 C35 1.348(9) . ? C34 C38 1.504(9) . ? C35 C36 1.395(8) . ? C36 C39 1.507(8) . ? C40 C45 1.381(6) . ? C40 C41 1.404(6) . ? C41 C42 1.391(7) . ? C41 C46 1.493(7) . ? C42 C43 1.384(8) . ? C43 C44 1.383(8) . ? C43 C47 1.518(8) . ? C44 C45 1.393(7) . ? C45 C48 1.518(7) . ? C49 C54 1.367(7) . ? C49 C50 1.399(6) . ? C50 C51 1.368(7) . ? C51 C52 1.363(9) . ? C52 C53 1.386(9) . ? C53 C54 1.386(8) . ? 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 C1 N1 C4 124.7(4) . . ? C1 N1 C3 111.1(3) . . ? C4 N1 C3 124.2(3) . . ? C1 N2 C13 125.0(3) . . ? C1 N2 C2 110.6(3) . . ? C13 N2 C2 124.4(3) . . ? N2 C1 N1 113.5(4) . . ? C22 C2 N2 112.2(4) . . ? C22 C2 C3 116.5(4) . . ? N2 C2 C3 101.5(3) . . ? N1 C3 C2 103.3(3) . . ? C5 C4 C9 122.9(4) . . ? C5 C4 N1 119.5(4) . . ? C9 C4 N1 117.6(4) . . ? C4 C5 C6 117.7(5) . . ? C4 C5 C10 121.2(5) . . ? C6 C5 C10 121.1(5) . . ? C7 C6 C5 121.4(5) . . ? C8 C7 C6 119.3(4) . . ? C8 C7 C11 120.3(5) . . ? C6 C7 C11 120.4(5) . . ? C7 C8 C9 122.2(5) . . ? C8 C9 C4 116.5(4) . . ? C8 C9 C12 121.3(5) . . ? C4 C9 C12 122.3(4) . . ? C18 C13 C14 122.5(3) . . ? C18 C13 N2 118.8(3) . . ? C14 C13 N2 118.7(4) . . ? C13 C14 C15 118.1(4) . . ? C13 C14 C19 123.1(4) . . ? C15 C14 C19 118.8(4) . . ? C14 C15 C16 120.5(4) . . ? C17 C16 C15 118.7(4) . . ? C17 C16 C20 120.8(5) . . ? C15 C16 C20 120.5(5) . . ? C16 C17 C18 122.3(4) . . ? C17 C18 C13 117.8(4) . . ? C17 C18 C21 120.5(4) . . ? C13 C18 C21 121.7(4) . . ? C23 C22 C27 117.7(6) . . ? C23 C22 C2 124.6(5) . . ? C27 C22 C2 117.7(5) . . ? C24 C23 C22 120.9(7) . . ? C23 C24 C25 118.9(8) . . ? C26 C25 C24 121.1(7) . . ? C27 C26 C25 119.9(8) . . ? C26 C27 C22 121.5(8) . . ? C28 N3 C31 128.2(4) . . ? C28 N3 C30 110.4(4) . . ? C31 N3 C30 120.9(4) . . ? C28 N4 C40 126.3(3) . . ? C28 N4 C29 108.4(3) . . ? C40 N4 C29 121.1(3) . . ? N3 C28 N4 114.9(4) . . ? N4 C29 C49 112.6(3) . . ? N4 C29 C30 102.3(3) . . ? C49 C29 C30 116.5(4) . . ? N3 C30 C29 103.2(3) . . ? C36 C31 C32 122.2(5) . . ? C36 C31 N3 118.9(4) . . ? C32 C31 N3 118.8(4) . . ? C33 C32 C31 117.0(5) . . ? C33 C32 C37 122.0(5) . . ? C31 C32 C37 121.0(5) . . ? C34 C33 C32 122.1(5) . . ? C35 C34 C33 118.6(5) . . ? C35 C34 C38 122.2(6) . . ? C33 C34 C38 119.2(6) . . ? C34 C35 C36 122.5(5) . . ? C31 C36 C35 117.5(5) . . ? C31 C36 C39 121.2(5) . . ? C35 C36 C39 121.3(5) . . ? C45 C40 C41 121.8(4) . . ? C45 C40 N4 120.2(4) . . ? C41 C40 N4 117.9(4) . . ? C42 C41 C40 117.9(4) . . ? C42 C41 C46 120.6(4) . . ? C40 C41 C46 121.5(4) . . ? C43 C42 C41 121.9(5) . . ? C44 C43 C42 118.0(5) . . ? C44 C43 C47 122.4(5) . . ? C42 C43 C47 119.6(5) . . ? C43 C44 C45 122.7(5) . . ? C40 C45 C44 117.6(4) . . ? C40 C45 C48 122.5(5) . . ? C44 C45 C48 119.8(4) . . ? C54 C49 C50 118.2(4) . . ? C54 C49 C29 120.2(4) . . ? C50 C49 C29 121.6(4) . . ? C51 C50 C49 120.4(5) . . ? C52 C51 C50 121.3(5) . . ? C51 C52 C53 119.0(5) . . ? C52 C53 C54 120.0(5) . . ? C49 C54 C53 121.0(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C28 H28 I2 0.960(19) 2.74(2) 3.634(4) 155(3) 4_455 C2 H2 I1 1.00 2.98 3.860(5) 147.3 4_567 C1 H1 I1 0.93(2) 2.80(4) 3.655(4) 153(6) . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.100 _refine_diff_density_min -0.678 _refine_diff_density_rms 0.081 # Attachment 'web_deposit_cif_file_4_JunZhang_1314601021.mo_10726a.cif' data_mo_10726a _database_code_depnum_ccdc_archive 'CCDC 841931' #TrackingRef 'web_deposit_cif_file_4_JunZhang_1314601021.mo_10726a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H37 I N2' _chemical_formula_weight 552.52 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 13.2441(17) _cell_length_b 15.930(2) _cell_length_c 27.319(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5763.9(13) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9917 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 24.58 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2272 _exptl_absorpt_coefficient_mu 1.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6021 _exptl_absorpt_correction_T_max 0.8056 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 6.64 _diffrn_reflns_number 41229 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0539 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 27.43 _reflns_number_total 13047 _reflns_number_gt 8191 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.1098P)^2^+4.6863P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(3) _refine_ls_number_reflns 13047 _refine_ls_number_parameters 617 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1057 _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_ref 0.2095 _refine_ls_wR_factor_gt 0.1781 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 I1 I 0.92462(3) 0.49968(3) 0.91565(2) 0.0843(2) Uani 1 1 d . . . N1 N 0.1737(4) 0.8457(3) 0.01361(17) 0.0452(11) Uani 1 1 d . . . N2 N 0.1399(4) 0.8395(3) 0.09241(17) 0.0483(11) Uani 1 1 d . . . C1 C 0.1065(4) 0.8553(4) 0.0477(2) 0.0456(13) Uani 1 1 d . . . H1 H 0.036(5) 0.875(4) 0.037(2) 0.046(16) Uiso 1 1 d . . . C2 C 0.2500(4) 0.8166(4) 0.0905(2) 0.0457(12) Uani 1 1 d . . . H2 H 0.2889 0.8640 0.1053 0.055 Uiso 1 1 calc R . . C3 C 0.2704(5) 0.8168(5) 0.0357(2) 0.0527(14) Uani 1 1 d . . . H3A H 0.3262 0.8557 0.0275 0.063 Uiso 1 1 calc R . . H3B H 0.2882 0.7598 0.0241 0.063 Uiso 1 1 calc R . . C4 C 0.1566(4) 0.8443(4) -0.0383(2) 0.0475(13) Uani 1 1 d . . . C5 C 0.1895(5) 0.9127(4) -0.0659(2) 0.0505(14) Uani 1 1 d . . . C6 C 0.1769(7) 0.9079(5) -0.1159(3) 0.070(2) Uani 1 1 d . . . H6 H 0.2019 0.9525 -0.1355 0.084 Uiso 1 1 calc R . . C7 C 0.1300(7) 0.8415(6) -0.1387(3) 0.073(2) Uani 1 1 d . . . C8 C 0.0968(6) 0.7771(5) -0.1096(3) 0.070(2) Uani 1 1 d . . . H8 H 0.0619 0.7318 -0.1246 0.084 Uiso 1 1 calc R . . C9 C 0.1121(6) 0.7748(5) -0.0586(3) 0.0632(17) Uani 1 1 d . . . C10 C 0.2364(7) 0.9885(5) -0.0421(3) 0.078(2) Uani 1 1 d . . . H10A H 0.1984 1.0031 -0.0126 0.117 Uiso 1 1 calc R . . H10B H 0.2349 1.0358 -0.0650 0.117 Uiso 1 1 calc R . . H10C H 0.3066 0.9759 -0.0333 0.117 Uiso 1 1 calc R . . C11 C 0.1177(10) 0.8387(9) -0.1940(3) 0.116(4) Uani 1 1 d . . . H11A H 0.0518 0.8621 -0.2030 0.175 Uiso 1 1 calc R . . H11B H 0.1219 0.7804 -0.2053 0.175 Uiso 1 1 calc R . . H11C H 0.1713 0.8718 -0.2094 0.175 Uiso 1 1 calc R . . C12 C 0.0787(11) 0.6998(7) -0.0284(4) 0.120(5) Uani 1 1 d . . . H12A H 0.1379 0.6734 -0.0134 0.181 Uiso 1 1 calc R . . H12B H 0.0447 0.6591 -0.0497 0.181 Uiso 1 1 calc R . . H12C H 0.0321 0.7184 -0.0028 0.181 Uiso 1 1 calc R . . C13 C 0.0797(4) 0.8441(4) 0.1364(2) 0.0495(13) Uani 1 1 d . . . C14 C 0.0165(5) 0.7789(5) 0.1476(2) 0.0581(16) Uani 1 1 d . . . C15 C -0.0404(5) 0.7850(5) 0.1910(3) 0.0660(18) Uani 1 1 d . . . H15 H -0.0858 0.7413 0.1998 0.079 Uiso 1 1 calc R . . C16 C -0.0305(6) 0.8538(6) 0.2207(3) 0.076(2) Uani 1 1 d . . . H16 H -0.0690 0.8571 0.2499 0.091 Uiso 1 1 calc R . . C17 C 0.0329(6) 0.9170(6) 0.2090(3) 0.076(2) Uani 1 1 d . . . H17 H 0.0386 0.9637 0.2305 0.091 Uiso 1 1 calc R . . C18 C 0.0908(5) 0.9153(5) 0.1660(3) 0.0624(17) Uani 1 1 d . . . C19 C 0.0018(5) 0.7034(5) 0.1156(3) 0.068(2) Uani 1 1 d . . . H19 H 0.0605 0.7017 0.0926 0.081 Uiso 1 1 calc R . . C20 C -0.0914(7) 0.7132(8) 0.0846(4) 0.109(4) Uani 1 1 d . . . H20A H -0.1510 0.7166 0.1057 0.164 Uiso 1 1 calc R . . H20B H -0.0978 0.6647 0.0627 0.164 Uiso 1 1 calc R . . H20C H -0.0860 0.7646 0.0651 0.164 Uiso 1 1 calc R . . C21 C 0.0018(9) 0.6201(6) 0.1431(3) 0.095(3) Uani 1 1 d . . . H21A H 0.0697 0.6088 0.1556 0.143 Uiso 1 1 calc R . . H21B H -0.0185 0.5750 0.1208 0.143 Uiso 1 1 calc R . . H21C H -0.0459 0.6231 0.1704 0.143 Uiso 1 1 calc R . . C22 C 0.1557(6) 0.9907(5) 0.1525(3) 0.076(2) Uani 1 1 d . . . H22 H 0.2028 0.9731 0.1258 0.092 Uiso 1 1 calc R . . C23 C 0.0907(11) 1.0603(7) 0.1333(5) 0.136(5) Uani 1 1 d . . . H23A H 0.0545 1.0409 0.1041 0.204 Uiso 1 1 calc R . . H23B H 0.1332 1.1085 0.1247 0.204 Uiso 1 1 calc R . . H23C H 0.0419 1.0769 0.1584 0.204 Uiso 1 1 calc R . . C24 C 0.2185(11) 1.0191(10) 0.1955(4) 0.149(6) Uani 1 1 d . . . H24A H 0.1827 1.0065 0.2260 0.223 Uiso 1 1 calc R . . H24B H 0.2302 1.0797 0.1932 0.223 Uiso 1 1 calc R . . H24C H 0.2834 0.9896 0.1952 0.223 Uiso 1 1 calc R . . C25 C 0.2774(4) 0.7374(4) 0.1184(2) 0.0480(14) Uani 1 1 d . . . C26 C 0.2862(6) 0.7414(5) 0.1678(3) 0.0674(18) Uani 1 1 d . . . H26 H 0.2739 0.7931 0.1841 0.081 Uiso 1 1 calc R . . C27 C 0.3131(7) 0.6710(6) 0.1951(3) 0.084(2) Uani 1 1 d . . . H27 H 0.3195 0.6750 0.2297 0.101 Uiso 1 1 calc R . . C28 C 0.3299(7) 0.5980(6) 0.1725(4) 0.090(3) Uani 1 1 d . . . H28 H 0.3470 0.5498 0.1912 0.108 Uiso 1 1 calc R . . C29 C 0.3230(8) 0.5924(5) 0.1234(4) 0.092(3) Uani 1 1 d . . . H29 H 0.3367 0.5405 0.1076 0.111 Uiso 1 1 calc R . . C30 C 0.2960(6) 0.6617(5) 0.0957(3) 0.0690(18) Uani 1 1 d . . . H30 H 0.2903 0.6571 0.0612 0.083 Uiso 1 1 calc R . . I2 I 0.93919(6) 0.02416(6) 0.00029(3) 0.1273(3) Uani 1 1 d . . . N3 N 0.1657(4) 0.3317(3) 0.97871(16) 0.0438(11) Uani 1 1 d . . . N4 N 0.2027(3) 0.3345(3) 0.90043(16) 0.0417(10) Uani 1 1 d . . . C31 C 0.2336(5) 0.3456(3) 0.9464(2) 0.0442(12) Uani 1 1 d . . . H31 H 0.307(4) 0.356(3) 0.9492(18) 0.031(13) Uiso 1 1 d . . . C32 C 0.0922(4) 0.3105(3) 0.9007(2) 0.0442(12) Uani 1 1 d . . . H32 H 0.0530 0.3590 0.8874 0.053 Uiso 1 1 calc R . . C33 C 0.0704(5) 0.3047(4) 0.9555(2) 0.0525(14) Uani 1 1 d . . . H33A H 0.0141 0.3424 0.9649 0.063 Uiso 1 1 calc R . . H33B H 0.0531 0.2465 0.9651 0.063 Uiso 1 1 calc R . . C34 C 0.1858(5) 0.3304(4) 1.0306(2) 0.0502(14) Uani 1 1 d . . . C35 C 0.1650(5) 0.4013(5) 1.0584(3) 0.0608(17) Uani 1 1 d . . . C36 C 0.1888(6) 0.3962(6) 1.1078(3) 0.080(2) Uani 1 1 d . . . H36 H 0.1747 0.4434 1.1279 0.096 Uiso 1 1 calc R . . C37 C 0.2311(6) 0.3274(6) 1.1292(3) 0.073(2) Uani 1 1 d . . . C38 C 0.2514(7) 0.2580(6) 1.1005(3) 0.079(2) Uani 1 1 d . . . H38 H 0.2806 0.2094 1.1149 0.095 Uiso 1 1 calc R . . C39 C 0.2290(6) 0.2589(4) 1.0503(2) 0.0628(17) Uani 1 1 d . . . C40 C 0.1244(7) 0.4787(5) 1.0353(4) 0.084(2) Uani 1 1 d . . . H40A H 0.1598 0.4891 1.0044 0.127 Uiso 1 1 calc R . . H40B H 0.1346 0.5265 1.0574 0.127 Uiso 1 1 calc R . . H40C H 0.0521 0.4716 1.0289 0.127 Uiso 1 1 calc R . . C41 C 0.2570(10) 0.3267(10) 1.1828(3) 0.134(5) Uani 1 1 d . . . H41A H 0.2456 0.3827 1.1966 0.201 Uiso 1 1 calc R . . H41B H 0.3280 0.3111 1.1870 0.201 Uiso 1 1 calc R . . H41C H 0.2141 0.2859 1.1998 0.201 Uiso 1 1 calc R . . C42 C 0.2462(10) 0.1810(6) 1.0202(3) 0.109(4) Uani 1 1 d . . . H42A H 0.1973 0.1792 0.9933 0.164 Uiso 1 1 calc R . . H42B H 0.2377 0.1313 1.0409 0.164 Uiso 1 1 calc R . . H42C H 0.3149 0.1818 1.0068 0.164 Uiso 1 1 calc R . . C43 C 0.2651(4) 0.3457(4) 0.8576(2) 0.0444(12) Uani 1 1 d . . . C44 C 0.3280(5) 0.2804(4) 0.8437(2) 0.0545(15) Uani 1 1 d . . . C45 C 0.3889(6) 0.2940(5) 0.8020(3) 0.074(2) Uani 1 1 d . . . H45 H 0.4338 0.2513 0.7912 0.089 Uiso 1 1 calc R . . C46 C 0.3836(7) 0.3686(6) 0.7768(3) 0.077(2) Uani 1 1 d . . . H46 H 0.4223 0.3758 0.7479 0.092 Uiso 1 1 calc R . . C47 C 0.3241(6) 0.4320(5) 0.7927(3) 0.072(2) Uani 1 1 d . . . H47 H 0.3249 0.4839 0.7756 0.086 Uiso 1 1 calc R . . C48 C 0.2614(5) 0.4232(4) 0.8335(2) 0.0528(14) Uani 1 1 d . . . C49 C 0.3372(5) 0.1998(5) 0.8716(3) 0.0668(18) Uani 1 1 d . . . H49 H 0.2770 0.1960 0.8936 0.080 Uiso 1 1 calc R . . C50 C 0.4301(8) 0.2053(8) 0.9043(5) 0.121(4) Uani 1 1 d . . . H50A H 0.4869 0.2278 0.8855 0.182 Uiso 1 1 calc R . . H50B H 0.4472 0.1491 0.9164 0.182 Uiso 1 1 calc R . . H50C H 0.4158 0.2423 0.9321 0.182 Uiso 1 1 calc R . . C51 C 0.3335(10) 0.1242(6) 0.8374(4) 0.106(3) Uani 1 1 d . . . H51A H 0.2663 0.1203 0.8225 0.160 Uiso 1 1 calc R . . H51B H 0.3475 0.0729 0.8560 0.160 Uiso 1 1 calc R . . H51C H 0.3843 0.1308 0.8116 0.160 Uiso 1 1 calc R . . C52 C 0.1967(6) 0.4970(5) 0.8511(2) 0.0672(17) Uani 1 1 d . . . H52 H 0.1482 0.4751 0.8760 0.081 Uiso 1 1 calc R . . C53 C 0.1358(10) 0.5327(8) 0.8090(3) 0.115(4) Uani 1 1 d . . . H53A H 0.1760 0.5749 0.7917 0.173 Uiso 1 1 calc R . . H53B H 0.0741 0.5588 0.8217 0.173 Uiso 1 1 calc R . . H53C H 0.1177 0.4874 0.7864 0.173 Uiso 1 1 calc R . . C54 C 0.2603(9) 0.5625(7) 0.8753(5) 0.115(4) Uani 1 1 d . . . H54A H 0.2991 0.5369 0.9019 0.172 Uiso 1 1 calc R . . H54B H 0.2167 0.6067 0.8886 0.172 Uiso 1 1 calc R . . H54C H 0.3067 0.5869 0.8512 0.172 Uiso 1 1 calc R . . C55 C 0.0718(5) 0.2360(4) 0.8687(2) 0.0476(13) Uani 1 1 d . . . C56 C 0.0540(6) 0.1559(4) 0.8872(3) 0.0628(17) Uani 1 1 d . . . H56 H 0.0555 0.1465 0.9215 0.075 Uiso 1 1 calc R . . C57 C 0.0342(6) 0.0900(5) 0.8557(4) 0.080(2) Uani 1 1 d . . . H57 H 0.0216 0.0357 0.8688 0.096 Uiso 1 1 calc R . . C58 C 0.0326(7) 0.1016(6) 0.8059(4) 0.089(3) Uani 1 1 d . . . H58 H 0.0221 0.0554 0.7844 0.107 Uiso 1 1 calc R . . C59 C 0.0465(8) 0.1810(7) 0.7876(3) 0.090(3) Uani 1 1 d . . . H59 H 0.0446 0.1902 0.7533 0.108 Uiso 1 1 calc R . . C60 C 0.0632(6) 0.2470(5) 0.8186(2) 0.0683(19) Uani 1 1 d . . . H60 H 0.0690 0.3019 0.8054 0.082 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0520(2) 0.0606(2) 0.1403(5) 0.0005(3) 0.0021(3) 0.0159(2) N1 0.039(2) 0.045(2) 0.052(3) -0.001(2) 0.004(2) -0.0028(19) N2 0.038(2) 0.059(3) 0.048(3) 0.004(2) 0.005(2) 0.001(2) C1 0.032(3) 0.049(3) 0.056(4) 0.000(3) 0.004(3) -0.003(2) C2 0.033(3) 0.053(3) 0.052(3) 0.002(3) 0.002(2) -0.007(2) C3 0.036(3) 0.070(4) 0.052(3) 0.001(3) 0.008(3) -0.003(3) C4 0.041(3) 0.055(3) 0.047(3) -0.003(3) 0.003(3) 0.002(3) C5 0.048(3) 0.043(3) 0.060(4) -0.006(3) -0.002(3) 0.015(3) C6 0.088(5) 0.067(4) 0.056(4) 0.008(3) -0.004(4) 0.009(4) C7 0.075(5) 0.092(6) 0.051(4) -0.011(4) -0.010(4) 0.010(4) C8 0.055(4) 0.083(5) 0.071(5) -0.030(4) -0.003(3) -0.004(4) C9 0.054(4) 0.064(4) 0.073(4) -0.013(3) -0.001(3) -0.005(3) C10 0.116(6) 0.053(4) 0.065(4) 0.012(3) -0.004(4) -0.014(4) C11 0.122(9) 0.163(11) 0.064(5) -0.016(6) -0.024(6) 0.015(8) C12 0.171(12) 0.102(7) 0.089(6) -0.015(5) 0.021(7) -0.078(8) C13 0.036(3) 0.065(4) 0.048(3) 0.003(3) 0.005(3) 0.004(3) C14 0.037(3) 0.085(5) 0.053(4) 0.010(3) -0.003(3) 0.007(3) C15 0.048(4) 0.084(5) 0.066(4) 0.015(4) 0.004(3) -0.001(3) C16 0.077(5) 0.094(6) 0.057(4) 0.020(4) 0.026(4) 0.028(4) C17 0.068(5) 0.100(6) 0.059(4) -0.005(4) 0.022(4) 0.015(4) C18 0.054(4) 0.076(4) 0.057(4) 0.006(3) 0.002(3) 0.008(3) C19 0.046(4) 0.094(5) 0.064(4) 0.012(4) -0.008(3) -0.027(4) C20 0.072(6) 0.147(9) 0.108(7) 0.014(7) -0.031(6) -0.052(6) C21 0.120(8) 0.089(6) 0.077(5) -0.005(4) 0.005(5) -0.036(6) C22 0.084(5) 0.063(5) 0.082(5) -0.019(4) 0.023(4) -0.007(4) C23 0.170(13) 0.085(7) 0.153(10) 0.036(7) 0.048(10) -0.009(8) C24 0.155(12) 0.182(15) 0.108(8) -0.020(8) -0.009(8) -0.081(12) C25 0.032(3) 0.050(3) 0.062(4) 0.003(3) 0.000(3) -0.007(2) C26 0.069(5) 0.070(4) 0.064(4) -0.001(3) -0.008(4) -0.007(4) C27 0.085(6) 0.097(7) 0.071(5) 0.019(5) -0.015(4) -0.009(5) C28 0.084(6) 0.074(6) 0.113(7) 0.030(5) -0.022(5) 0.005(4) C29 0.122(8) 0.055(4) 0.100(7) 0.004(4) -0.008(6) 0.003(5) C30 0.079(5) 0.061(4) 0.067(4) -0.004(3) -0.007(4) -0.001(4) I2 0.1150(5) 0.1733(7) 0.0935(4) 0.0145(5) 0.0152(4) 0.0838(5) N3 0.043(3) 0.045(3) 0.043(2) 0.001(2) 0.002(2) -0.003(2) N4 0.034(2) 0.043(2) 0.048(3) -0.0001(19) 0.0045(19) 0.0007(18) C31 0.041(3) 0.042(3) 0.050(3) 0.001(2) 0.000(3) 0.001(2) C32 0.036(3) 0.045(3) 0.052(3) 0.005(2) -0.004(2) 0.002(2) C33 0.033(3) 0.072(4) 0.053(3) 0.006(3) 0.012(3) -0.004(3) C34 0.053(3) 0.056(3) 0.042(3) 0.002(3) 0.009(3) -0.014(3) C35 0.048(4) 0.074(4) 0.061(4) -0.010(3) 0.010(3) -0.007(3) C36 0.065(5) 0.110(7) 0.064(5) -0.038(5) 0.015(4) -0.014(5) C37 0.062(4) 0.103(6) 0.053(4) 0.008(4) -0.002(4) -0.020(4) C38 0.092(6) 0.087(6) 0.058(4) 0.019(4) -0.015(4) -0.016(5) C39 0.070(4) 0.064(4) 0.055(4) -0.001(3) -0.004(3) 0.003(3) C40 0.087(6) 0.057(5) 0.110(6) -0.010(4) 0.000(5) 0.000(4) C41 0.117(10) 0.232(15) 0.053(5) -0.013(7) -0.002(5) -0.039(10) C42 0.172(12) 0.076(6) 0.080(5) -0.001(4) -0.017(6) 0.047(7) C43 0.040(3) 0.053(3) 0.040(3) 0.004(2) 0.004(2) -0.007(2) C44 0.045(3) 0.057(3) 0.062(4) -0.006(3) 0.009(3) 0.001(3) C45 0.073(5) 0.080(5) 0.069(4) -0.010(4) 0.026(4) -0.004(4) C46 0.077(5) 0.094(6) 0.059(4) 0.002(4) 0.025(4) -0.006(4) C47 0.079(5) 0.076(5) 0.062(4) 0.016(4) 0.010(4) -0.017(4) C48 0.050(3) 0.057(3) 0.051(3) 0.008(3) 0.002(3) -0.011(3) C49 0.046(4) 0.069(4) 0.085(5) 0.010(4) 0.006(3) 0.013(3) C50 0.069(6) 0.126(8) 0.168(10) 0.049(8) -0.031(7) 0.018(6) C51 0.132(9) 0.071(5) 0.116(7) -0.007(5) 0.039(7) 0.005(5) C52 0.078(4) 0.058(3) 0.066(4) 0.015(3) 0.010(3) 0.005(4) C53 0.135(9) 0.122(8) 0.088(6) 0.023(6) -0.006(6) 0.064(7) C54 0.120(9) 0.085(7) 0.139(9) -0.037(6) -0.015(7) 0.000(6) C55 0.041(3) 0.046(3) 0.056(3) 0.009(2) -0.004(3) 0.000(3) C56 0.065(4) 0.053(4) 0.070(4) 0.008(3) -0.013(4) 0.004(3) C57 0.074(5) 0.047(4) 0.119(7) -0.008(4) -0.029(5) -0.006(3) C58 0.077(6) 0.075(5) 0.115(7) -0.030(5) -0.021(5) -0.014(4) C59 0.088(6) 0.108(7) 0.074(5) -0.020(5) -0.006(5) -0.025(5) C60 0.086(5) 0.062(4) 0.057(4) 0.004(3) -0.010(4) -0.016(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.297(7) . ? N1 C4 1.437(8) . ? N1 C3 1.489(8) . ? N2 C1 1.324(8) . ? N2 C13 1.445(7) . ? N2 C2 1.503(7) . ? C2 C25 1.517(8) . ? C2 C3 1.521(8) . ? C4 C9 1.370(9) . ? C4 C5 1.394(9) . ? C5 C6 1.379(10) . ? C5 C10 1.505(10) . ? C6 C7 1.376(12) . ? C7 C8 1.369(12) . ? C7 C11 1.522(11) . ? C8 C9 1.410(11) . ? C9 C12 1.518(12) . ? C13 C14 1.369(9) . ? C13 C18 1.400(10) . ? C14 C15 1.409(9) . ? C14 C19 1.499(11) . ? C15 C16 1.369(11) . ? C16 C17 1.348(13) . ? C17 C18 1.404(10) . ? C18 C22 1.522(11) . ? C19 C20 1.506(11) . ? C19 C21 1.523(12) . ? C22 C23 1.499(15) . ? C22 C24 1.508(13) . ? C25 C26 1.356(10) . ? C25 C30 1.378(10) . ? C26 C27 1.393(12) . ? C27 C28 1.335(14) . ? C28 C29 1.348(14) . ? C29 C30 1.385(12) . ? N3 C31 1.279(8) . ? N3 C34 1.442(7) . ? N3 C33 1.476(8) . ? N4 C31 1.334(7) . ? N4 C43 1.443(7) . ? N4 C32 1.512(7) . ? C32 C55 1.497(8) . ? C32 C33 1.528(8) . ? C34 C39 1.383(10) . ? C34 C35 1.389(10) . ? C35 C36 1.388(11) . ? C35 C40 1.485(11) . ? C36 C37 1.363(13) . ? C37 C38 1.380(13) . ? C37 C41 1.505(11) . ? C38 C39 1.405(10) . ? C39 C42 1.506(11) . ? C43 C44 1.386(9) . ? C43 C48 1.401(9) . ? C44 C45 1.414(9) . ? C44 C49 1.497(10) . ? C45 C46 1.375(12) . ? C46 C47 1.352(12) . ? C47 C48 1.396(10) . ? C48 C52 1.532(10) . ? C49 C50 1.523(12) . ? C49 C51 1.526(12) . ? C52 C54 1.494(13) . ? C52 C53 1.516(11) . ? C55 C60 1.385(9) . ? C55 C56 1.392(9) . ? C56 C57 1.382(10) . ? C57 C58 1.375(13) . ? C58 C59 1.372(14) . ? C59 C60 1.367(11) . ? 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 C1 N1 C4 127.0(5) . . ? C1 N1 C3 109.6(5) . . ? C4 N1 C3 122.1(5) . . ? C1 N2 C13 125.0(5) . . ? C1 N2 C2 109.8(5) . . ? C13 N2 C2 125.1(5) . . ? N1 C1 N2 114.2(5) . . ? N2 C2 C25 114.6(4) . . ? N2 C2 C3 101.9(5) . . ? C25 C2 C3 117.0(5) . . ? N1 C3 C2 104.3(5) . . ? C9 C4 C5 123.2(6) . . ? C9 C4 N1 118.6(6) . . ? C5 C4 N1 118.2(5) . . ? C6 C5 C4 117.0(6) . . ? C6 C5 C10 121.4(6) . . ? C4 C5 C10 121.6(6) . . ? C7 C6 C5 123.0(7) . . ? C8 C7 C6 117.3(6) . . ? C8 C7 C11 121.3(9) . . ? C6 C7 C11 121.4(9) . . ? C7 C8 C9 123.1(7) . . ? C4 C9 C8 116.1(7) . . ? C4 C9 C12 122.9(7) . . ? C8 C9 C12 121.0(7) . . ? C14 C13 C18 123.4(6) . . ? C14 C13 N2 119.0(6) . . ? C18 C13 N2 117.6(6) . . ? C13 C14 C15 117.6(7) . . ? C13 C14 C19 123.9(6) . . ? C15 C14 C19 118.5(6) . . ? C16 C15 C14 120.1(7) . . ? C17 C16 C15 121.2(7) . . ? C16 C17 C18 121.5(8) . . ? C13 C18 C17 116.2(7) . . ? C13 C18 C22 124.0(6) . . ? C17 C18 C22 119.7(7) . . ? C14 C19 C20 110.6(8) . . ? C14 C19 C21 114.3(6) . . ? C20 C19 C21 111.5(7) . . ? C23 C22 C24 111.5(10) . . ? C23 C22 C18 110.1(8) . . ? C24 C22 C18 111.1(8) . . ? C26 C25 C30 118.2(6) . . ? C26 C25 C2 118.8(6) . . ? C30 C25 C2 123.0(6) . . ? C25 C26 C27 121.2(8) . . ? C28 C27 C26 119.7(8) . . ? C27 C28 C29 120.4(8) . . ? C28 C29 C30 120.5(8) . . ? C25 C30 C29 119.9(7) . . ? C31 N3 C34 123.4(5) . . ? C31 N3 C33 110.9(5) . . ? C34 N3 C33 125.1(5) . . ? C31 N4 C43 124.8(5) . . ? C31 N4 C32 109.0(4) . . ? C43 N4 C32 126.1(4) . . ? N3 C31 N4 114.3(5) . . ? C55 C32 N4 111.8(5) . . ? C55 C32 C33 119.4(5) . . ? N4 C32 C33 101.7(4) . . ? N3 C33 C32 104.0(4) . . ? C39 C34 C35 122.7(6) . . ? C39 C34 N3 118.0(6) . . ? C35 C34 N3 119.3(6) . . ? C36 C35 C34 116.0(7) . . ? C36 C35 C40 123.0(7) . . ? C34 C35 C40 121.0(6) . . ? C37 C36 C35 123.9(8) . . ? C36 C37 C38 118.7(7) . . ? C36 C37 C41 121.1(10) . . ? C38 C37 C41 120.1(10) . . ? C37 C38 C39 120.3(8) . . ? C34 C39 C38 118.4(7) . . ? C34 C39 C42 122.0(6) . . ? C38 C39 C42 119.5(7) . . ? C44 C43 C48 123.6(5) . . ? C44 C43 N4 118.2(5) . . ? C48 C43 N4 118.1(5) . . ? C43 C44 C45 116.6(6) . . ? C43 C44 C49 123.6(6) . . ? C45 C44 C49 119.7(6) . . ? C46 C45 C44 120.5(7) . . ? C47 C46 C45 121.0(7) . . ? C46 C47 C48 121.9(7) . . ? C47 C48 C43 116.3(6) . . ? C47 C48 C52 120.4(6) . . ? C43 C48 C52 123.2(5) . . ? C44 C49 C50 108.4(7) . . ? C44 C49 C51 111.2(7) . . ? C50 C49 C51 115.5(8) . . ? C54 C52 C53 112.0(9) . . ? C54 C52 C48 111.1(7) . . ? C53 C52 C48 110.3(7) . . ? C60 C55 C56 117.3(6) . . ? C60 C55 C32 119.5(5) . . ? C56 C55 C32 123.1(5) . . ? C57 C56 C55 120.3(7) . . ? C58 C57 C56 121.1(8) . . ? C59 C58 C57 118.8(8) . . ? C60 C59 C58 120.4(8) . . ? C59 C60 C55 121.9(7) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2 I1 1.00 2.88 3.735(5) 144.4 4_466 C32 H32 I1 1.00 2.92 3.765(5) 143.1 1_455 C1 H1 I2 1.03(6) 2.88(6) 3.718(6) 140(4) 1_465 C31 H31 I2 0.99(6) 2.93(5) 3.720(6) 137(4) 4_456 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.863 _refine_diff_density_min -1.113 _refine_diff_density_rms 0.092