# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_b #TrackingRef '20120410.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 I N3 O' _chemical_formula_weight 377.18 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.870(3) _cell_length_b 15.196(3) _cell_length_c 6.0290(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.95(3) _cell_angle_gamma 90.00 _cell_volume 1453.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 12 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.723 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 2.202 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.5580 _exptl_absorpt_correction_T_max 0.8099 _exptl_absorpt_process_details ? _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 'Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 2779 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 25.40 _reflns_number_total 2683 _reflns_number_gt 1859 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 EXPRESS(Enraf-Nonius,1994)' _computing_cell_refinement 'CAD4 EXPRESS' _computing_data_reduction 'XCAD4(Harms & Wocadlo,1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^2^+1.9000P] 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 2683 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0941 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1704 _refine_ls_wR_factor_gt 0.1537 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 I I 0.35309(4) 0.82744(4) 0.23488(9) 0.0559(3) Uani 1 1 d . . . O O -0.0436(4) 0.8356(4) 0.5119(12) 0.0729(19) Uani 1 1 d . . . C1 C 0.3793(6) 1.0777(6) 1.0241(14) 0.056(2) Uani 1 1 d . . . N1 N 0.2502(4) 1.0375(4) 0.9054(11) 0.0505(17) Uani 1 1 d . . . N2 N 0.3113(4) 1.0030(4) 0.7857(10) 0.0436(15) Uani 1 1 d . . . C2 C 0.4382(7) 1.1202(6) 1.1635(16) 0.065(3) Uani 1 1 d . . . H2A H 0.4956 1.1159 1.1375 0.078 Uiso 1 1 calc R . . C3 C 0.4095(8) 1.1674(6) 1.3361(17) 0.070(3) Uani 1 1 d . . . H3A H 0.4474 1.1965 1.4299 0.084 Uiso 1 1 calc R . . N3 N 0.3883(5) 1.0233(5) 0.8469(12) 0.0540(18) Uani 1 1 d . . . C4 C 0.3226(9) 1.1730(6) 1.3747(16) 0.080(4) Uani 1 1 d . . . H4A H 0.3057 1.2031 1.5006 0.096 Uiso 1 1 calc R . . C5 C 0.2608(7) 1.1374(6) 1.2412(16) 0.061(2) Uani 1 1 d . . . H5A H 0.2036 1.1455 1.2656 0.074 Uiso 1 1 calc R . . C6 C 0.2926(6) 1.0860(5) 1.0588(13) 0.054(2) Uani 1 1 d . . . C7 C 0.2924(6) 0.9437(5) 0.6083(13) 0.052(2) Uani 1 1 d . . . C8 C 0.2064(6) 0.9143(5) 0.5842(13) 0.050(2) Uani 1 1 d . . . C9 C 0.1629(6) 0.8688(6) 0.7471(13) 0.055(2) Uani 1 1 d . . . H9A H 0.1909 0.8553 0.8794 0.066 Uiso 1 1 calc R . . C10 C 0.0818(7) 0.8434(6) 0.7209(14) 0.059(2) Uani 1 1 d . . . H10A H 0.0551 0.8125 0.8328 0.070 Uiso 1 1 calc R . . C11 C 0.0383(6) 0.8641(6) 0.5244(14) 0.054(2) Uani 1 1 d . . . C12 C 0.0801(6) 0.9087(6) 0.3617(14) 0.055(2) Uani 1 1 d . . . H12A H 0.0520 0.9225 0.2297 0.066 Uiso 1 1 calc R . . C13 C 0.1607(7) 0.9327(6) 0.3905(14) 0.062(3) Uani 1 1 d . . . H13A H 0.1873 0.9629 0.2769 0.075 Uiso 1 1 calc R . . C14 C -0.0922(6) 0.8534(7) 0.3172(16) 0.067(3) Uani 1 1 d . . . H14A H -0.1477 0.8294 0.3328 0.100 Uiso 1 1 calc R . . H14B H -0.0657 0.8270 0.1917 0.100 Uiso 1 1 calc R . . H14C H -0.0960 0.9159 0.2955 0.100 Uiso 1 1 calc R . . C15 C 0.3604(6) 0.9205(5) 0.4843(13) 0.050(2) Uani 1 1 d . . . H15A H 0.4118 0.9478 0.5134 0.060 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 I 0.0710(4) 0.0504(4) 0.0463(4) -0.0066(3) 0.0013(3) 0.0062(3) O 0.073(5) 0.068(5) 0.078(5) 0.003(4) 0.000(4) -0.005(4) C1 0.079(6) 0.043(5) 0.047(5) 0.001(4) 0.011(4) 0.001(5) N1 0.053(4) 0.046(4) 0.053(4) 0.004(3) 0.011(3) 0.006(3) N2 0.050(4) 0.041(4) 0.040(3) -0.003(3) -0.004(3) 0.006(3) C2 0.080(7) 0.059(6) 0.055(5) -0.009(5) -0.003(5) -0.003(5) C3 0.100(8) 0.051(6) 0.060(6) -0.007(5) -0.001(6) -0.028(6) N3 0.066(5) 0.045(4) 0.051(4) 0.001(3) 0.001(4) -0.002(4) C4 0.147(11) 0.047(6) 0.047(5) -0.009(4) 0.018(6) -0.034(7) C5 0.075(6) 0.042(5) 0.068(6) -0.008(5) 0.010(5) -0.002(5) C6 0.085(7) 0.033(4) 0.043(5) 0.007(4) 0.010(4) -0.004(4) C7 0.075(6) 0.042(5) 0.038(4) 0.004(4) 0.005(4) 0.011(4) C8 0.078(6) 0.037(4) 0.035(4) 0.000(3) 0.007(4) -0.004(4) C9 0.073(7) 0.054(5) 0.038(4) 0.001(4) 0.001(4) -0.005(5) C10 0.087(7) 0.054(6) 0.035(4) 0.004(4) -0.003(4) -0.009(5) C11 0.070(6) 0.043(5) 0.048(5) 0.000(4) 0.002(4) 0.007(5) C12 0.069(6) 0.048(5) 0.048(5) 0.005(4) 0.003(4) -0.001(5) C13 0.100(8) 0.045(5) 0.042(5) 0.004(4) 0.008(5) -0.004(5) C14 0.056(5) 0.077(7) 0.066(6) -0.008(5) -0.008(5) 0.003(5) C15 0.063(5) 0.048(5) 0.039(4) 0.001(4) 0.004(4) -0.001(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 I C15 2.066(8) . ? O C11 1.371(11) . ? O C14 1.419(11) . ? C1 N3 1.360(11) . ? C1 C6 1.401(13) . ? C1 C2 1.403(13) . ? N1 N2 1.326(9) . ? N1 C6 1.353(11) . ? N2 N3 1.307(10) . ? N2 C7 1.427(10) . ? C2 C3 1.350(14) . ? C2 H2A 0.9300 . ? C3 C4 1.406(17) . ? C3 H3A 0.9300 . ? C4 C5 1.369(15) . ? C4 H4A 0.9300 . ? C5 C6 1.446(12) . ? C5 H5A 0.9300 . ? C7 C15 1.368(11) . ? C7 C8 1.442(12) . ? C8 C13 1.392(12) . ? C8 C9 1.393(11) . ? C9 C10 1.350(13) . ? C9 H9A 0.9300 . ? C10 C11 1.397(12) . ? C10 H10A 0.9300 . ? C11 C12 1.372(12) . ? C12 C13 1.340(13) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 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 C11 O C14 119.1(8) . . ? N3 C1 C6 106.7(8) . . ? N3 C1 C2 132.3(9) . . ? C6 C1 C2 121.0(8) . . ? N2 N1 C6 103.1(7) . . ? N3 N2 N1 116.2(6) . . ? N3 N2 C7 123.0(7) . . ? N1 N2 C7 120.8(7) . . ? C3 C2 C1 118.5(10) . . ? C3 C2 H2A 120.8 . . ? C1 C2 H2A 120.8 . . ? C2 C3 C4 120.2(10) . . ? C2 C3 H3A 119.9 . . ? C4 C3 H3A 119.9 . . ? N2 N3 C1 104.8(7) . . ? C5 C4 C3 125.0(10) . . ? C5 C4 H4A 117.5 . . ? C3 C4 H4A 117.5 . . ? C4 C5 C6 113.9(10) . . ? C4 C5 H5A 123.1 . . ? C6 C5 H5A 123.1 . . ? N1 C6 C1 109.2(7) . . ? N1 C6 C5 129.6(9) . . ? C1 C6 C5 121.2(9) . . ? C15 C7 N2 114.5(8) . . ? C15 C7 C8 128.3(8) . . ? N2 C7 C8 117.2(7) . . ? C13 C8 C9 115.8(9) . . ? C13 C8 C7 120.0(8) . . ? C9 C8 C7 124.2(8) . . ? C10 C9 C8 122.8(9) . . ? C10 C9 H9A 118.6 . . ? C8 C9 H9A 118.6 . . ? C9 C10 C11 119.5(9) . . ? C9 C10 H10A 120.3 . . ? C11 C10 H10A 120.3 . . ? O C11 C12 125.8(9) . . ? O C11 C10 115.5(8) . . ? C12 C11 C10 118.7(9) . . ? C13 C12 C11 120.9(9) . . ? C13 C12 H12A 119.5 . . ? C11 C12 H12A 119.5 . . ? C12 C13 C8 122.4(9) . . ? C12 C13 H13A 118.8 . . ? C8 C13 H13A 118.8 . . ? O C14 H14A 109.5 . . ? O C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7 C15 I 122.6(7) . . ? C7 C15 H15A 118.7 . . ? I C15 H15A 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 C6 N1 N2 N3 0.7(9) . . . . ? C6 N1 N2 C7 177.5(7) . . . . ? N3 C1 C2 C3 -176.6(9) . . . . ? C6 C1 C2 C3 1.8(14) . . . . ? C1 C2 C3 C4 0.5(15) . . . . ? N1 N2 N3 C1 -0.7(9) . . . . ? C7 N2 N3 C1 -177.5(7) . . . . ? C6 C1 N3 N2 0.4(9) . . . . ? C2 C1 N3 N2 179.0(9) . . . . ? C2 C3 C4 C5 -3.9(16) . . . . ? C3 C4 C5 C6 4.5(14) . . . . ? N2 N1 C6 C1 -0.4(8) . . . . ? N2 N1 C6 C5 -177.9(8) . . . . ? N3 C1 C6 N1 0.0(9) . . . . ? C2 C1 C6 N1 -178.8(8) . . . . ? N3 C1 C6 C5 177.8(7) . . . . ? C2 C1 C6 C5 -1.0(13) . . . . ? C4 C5 C6 N1 175.3(8) . . . . ? C4 C5 C6 C1 -2.0(12) . . . . ? N3 N2 C7 C15 -10.0(11) . . . . ? N1 N2 C7 C15 173.4(7) . . . . ? N3 N2 C7 C8 168.7(7) . . . . ? N1 N2 C7 C8 -7.9(10) . . . . ? C15 C7 C8 C13 -62.6(12) . . . . ? N2 C7 C8 C13 118.9(8) . . . . ? C15 C7 C8 C9 118.9(10) . . . . ? N2 C7 C8 C9 -59.6(11) . . . . ? C13 C8 C9 C10 0.3(13) . . . . ? C7 C8 C9 C10 178.8(8) . . . . ? C8 C9 C10 C11 -0.8(14) . . . . ? C14 O C11 C12 -0.7(13) . . . . ? C14 O C11 C10 -179.6(8) . . . . ? C9 C10 C11 O 179.9(8) . . . . ? C9 C10 C11 C12 0.9(13) . . . . ? O C11 C12 C13 -179.3(8) . . . . ? C10 C11 C12 C13 -0.4(13) . . . . ? C11 C12 C13 C8 -0.1(14) . . . . ? C9 C8 C13 C12 0.2(13) . . . . ? C7 C8 C13 C12 -178.4(8) . . . . ? N2 C7 C15 I 174.6(5) . . . . ? C8 C7 C15 I -4.0(12) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.437 _refine_diff_density_min -0.669 _refine_diff_density_rms 0.134 # Attachment '20120410.pdf' _database_code_depnum_ccdc_archive 'CCDC 875380' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_b #TrackingRef '20121019.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 I N3 O2' _chemical_formula_weight 447.26 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.964(3) _cell_length_b 7.6020(15) _cell_length_c 16.564(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.44(3) _cell_angle_gamma 90.00 _cell_volume 1832.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 13 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.621 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 1.764 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.7192 _exptl_absorpt_correction_T_max 0.8433 _exptl_absorpt_process_details '(North, Phillips, Mathews,1968)' _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 'Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 3488 _diffrn_reflns_av_R_equivalents 0.0568 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 25.42 _reflns_number_total 3353 _reflns_number_gt 2317 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^2^+1.5000P] 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 3353 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0939 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1690 _refine_ls_wR_factor_gt 0.1521 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I I 0.19817(4) 0.14746(8) 0.83516(3) 0.0742(3) Uani 1 1 d . . . N1 N 0.2873(3) -0.1241(6) 1.0700(3) 0.0373(11) Uani 1 1 d . . . O1 O -0.1018(3) -0.4187(7) 0.8721(3) 0.0526(11) Uani 1 1 d . . . C1 C 0.3727(4) -0.2681(8) 1.1646(4) 0.0429(14) Uani 1 1 d . . . O2 O 0.0175(3) -0.4304(7) 0.7821(3) 0.0590(13) Uani 1 1 d . . . N2 N 0.3463(3) -0.2563(7) 1.0807(3) 0.0448(13) Uani 1 1 d . . . C2 C 0.4336(5) -0.3849(10) 1.2163(5) 0.063(2) Uani 1 1 d . . . H2B H 0.4657 -0.4704 1.1944 0.076 Uiso 1 1 calc R . . N3 N 0.2724(4) -0.0459(7) 1.1372(3) 0.0451(13) Uani 1 1 d . . . C3 C 0.4433(6) -0.3665(11) 1.2999(5) 0.074(2) Uani 1 1 d . . . H3B H 0.4819 -0.4432 1.3357 0.088 Uiso 1 1 calc R . . C4 C 0.3971(5) -0.2363(13) 1.3334(4) 0.066(2) Uani 1 1 d . . . H4A H 0.4073 -0.2277 1.3908 0.079 Uiso 1 1 calc R . . C5 C 0.3378(5) -0.1216(11) 1.2859(4) 0.0584(19) Uani 1 1 d . . . H5A H 0.3066 -0.0368 1.3091 0.070 Uiso 1 1 calc R . . C6 C 0.3263(4) -0.1387(8) 1.1992(4) 0.0402(14) Uani 1 1 d . . . C7 C 0.2377(4) -0.0718(8) 0.9860(3) 0.0410(14) Uani 1 1 d . . . C8 C 0.1493(4) -0.1702(8) 0.9587(4) 0.0399(14) Uani 1 1 d . . . C9 C 0.0868(4) -0.1741(9) 1.0072(4) 0.0460(15) Uani 1 1 d . . . H9A H 0.1016 -0.1212 1.0593 0.055 Uiso 1 1 calc R . . C10 C 0.0019(4) -0.2551(9) 0.9806(4) 0.0453(15) Uani 1 1 d . . . H10A H -0.0403 -0.2520 1.0139 0.054 Uiso 1 1 calc R . . C11 C -0.0199(4) -0.3398(8) 0.9055(4) 0.0412(14) Uani 1 1 d . . . C12 C 0.0443(4) -0.3418(8) 0.8565(4) 0.0397(14) Uani 1 1 d . . . C13 C 0.1285(4) -0.2591(9) 0.8826(4) 0.0449(15) Uani 1 1 d . . . H13A H 0.1710 -0.2626 0.8496 0.054 Uiso 1 1 calc R . . C14 C -0.1725(5) -0.4008(10) 0.9152(5) 0.061(2) Uani 1 1 d . . . H14A H -0.2267 -0.4597 0.8850 0.092 Uiso 1 1 calc R . . H14B H -0.1856 -0.2783 0.9205 0.092 Uiso 1 1 calc R . . H14C H -0.1530 -0.4522 0.9694 0.092 Uiso 1 1 calc R . . C15 C 0.0689(5) -0.4039(11) 0.7210(4) 0.063(2) Uani 1 1 d . . . H15A H 0.0428 -0.4728 0.6727 0.095 Uiso 1 1 calc R . . H15B H 0.1314 -0.4392 0.7428 0.095 Uiso 1 1 calc R . . H15C H 0.0671 -0.2817 0.7061 0.095 Uiso 1 1 calc R . . C16 C 0.2725(4) 0.0570(8) 0.9511(3) 0.0415(14) Uani 1 1 d . . . C17 C 0.3701(4) 0.1578(7) 0.9909(3) 0.0379(14) Uani 1 1 d . . . H17A H 0.4077 0.1049 1.0415 0.045 Uiso 1 1 calc R . . C18 C 0.3709(6) 0.3442(10) 0.9880(5) 0.065(2) Uani 1 1 d . . . H18A H 0.4078 0.4066 1.0352 0.078 Uiso 1 1 calc R . . H18B H 0.3149 0.4036 0.9600 0.078 Uiso 1 1 calc R . . C19 C 0.4194(5) 0.2343(10) 0.9369(5) 0.063(2) Uani 1 1 d . . . H19A H 0.3931 0.2271 0.8777 0.076 Uiso 1 1 calc R . . H19B H 0.4860 0.2301 0.9529 0.076 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 I 0.0685(4) 0.0839(4) 0.0566(4) 0.0326(3) -0.0135(2) -0.0174(3) N1 0.042(3) 0.036(3) 0.032(3) 0.004(2) 0.004(2) 0.000(2) O1 0.040(2) 0.069(3) 0.050(3) 0.000(2) 0.013(2) -0.014(2) C1 0.049(4) 0.040(3) 0.036(3) 0.007(3) 0.000(3) -0.001(3) O2 0.059(3) 0.084(3) 0.036(2) -0.017(2) 0.013(2) -0.026(3) N2 0.045(3) 0.043(3) 0.043(3) -0.002(2) 0.002(2) 0.015(3) C2 0.063(4) 0.053(5) 0.066(5) 0.008(4) -0.002(4) 0.016(4) N3 0.053(3) 0.049(3) 0.029(2) -0.006(2) 0.002(2) 0.009(3) C3 0.081(6) 0.072(6) 0.055(5) 0.027(4) -0.010(4) 0.006(5) C4 0.064(5) 0.095(6) 0.030(3) 0.018(4) -0.006(3) -0.016(5) C5 0.053(4) 0.085(6) 0.036(4) -0.004(4) 0.007(3) -0.004(4) C6 0.042(3) 0.044(4) 0.032(3) -0.002(3) 0.002(3) 0.001(3) C7 0.052(4) 0.041(3) 0.024(3) -0.001(3) -0.002(3) 0.002(3) C8 0.047(3) 0.041(4) 0.031(3) 0.007(3) 0.008(3) -0.003(3) C9 0.052(4) 0.054(4) 0.030(3) -0.001(3) 0.004(3) -0.005(3) C10 0.045(3) 0.051(4) 0.044(4) 0.008(3) 0.019(3) 0.001(3) C11 0.041(3) 0.047(4) 0.036(3) 0.003(3) 0.009(3) -0.008(3) C12 0.040(3) 0.045(4) 0.032(3) -0.003(3) 0.003(3) -0.001(3) C13 0.050(4) 0.051(4) 0.034(3) -0.004(3) 0.011(3) -0.007(3) C14 0.044(4) 0.057(5) 0.080(5) 0.010(4) 0.011(4) -0.011(3) C15 0.069(5) 0.085(5) 0.038(4) -0.020(4) 0.017(3) -0.018(4) C16 0.045(3) 0.042(4) 0.031(3) 0.007(3) -0.004(3) -0.005(3) C17 0.056(4) 0.032(3) 0.023(3) 0.013(2) 0.005(3) 0.010(3) C18 0.078(5) 0.054(5) 0.064(5) -0.004(4) 0.015(4) -0.013(4) C19 0.054(4) 0.063(5) 0.070(5) -0.009(4) 0.009(4) -0.008(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 I C16 2.098(5) . ? N1 N2 1.322(7) . ? N1 N3 1.325(7) . ? N1 C7 1.470(7) . ? O1 C11 1.360(7) . ? O1 C14 1.414(8) . ? C1 N2 1.357(7) . ? C1 C6 1.401(9) . ? C1 C2 1.410(9) . ? O2 C12 1.380(7) . ? O2 C15 1.420(8) . ? C2 C3 1.367(12) . ? C2 H2B 0.9300 . ? N3 C6 1.348(8) . ? C3 C4 1.394(12) . ? C3 H3B 0.9300 . ? C4 C5 1.357(11) . ? C4 H4A 0.9300 . ? C5 C6 1.412(9) . ? C5 H5A 0.9300 . ? C7 C16 1.306(9) . ? C7 C8 1.495(9) . ? C8 C9 1.368(9) . ? C8 C13 1.400(8) . ? C9 C10 1.388(9) . ? C9 H9A 0.9300 . ? C10 C11 1.372(9) . ? C10 H10A 0.9300 . ? C11 C12 1.394(9) . ? C12 C13 1.384(9) . ? C13 H13A 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.645(8) . ? C17 C19 1.410(10) . ? C17 C18 1.418(9) . ? C17 H17A 0.9800 . ? C18 C19 1.492(11) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? 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 N2 N1 N3 117.7(5) . . ? N2 N1 C7 120.5(5) . . ? N3 N1 C7 121.8(5) . . ? C11 O1 C14 117.4(5) . . ? N2 C1 C6 108.5(5) . . ? N2 C1 C2 131.0(6) . . ? C6 C1 C2 120.4(6) . . ? C12 O2 C15 118.4(5) . . ? N1 N2 C1 102.4(5) . . ? C3 C2 C1 116.8(7) . . ? C3 C2 H2B 121.6 . . ? C1 C2 H2B 121.6 . . ? N1 N3 C6 102.6(5) . . ? C2 C3 C4 122.1(7) . . ? C2 C3 H3B 119.0 . . ? C4 C3 H3B 119.0 . . ? C5 C4 C3 122.9(7) . . ? C5 C4 H4A 118.5 . . ? C3 C4 H4A 118.5 . . ? C4 C5 C6 116.1(7) . . ? C4 C5 H5A 122.0 . . ? C6 C5 H5A 122.0 . . ? N3 C6 C1 108.7(5) . . ? N3 C6 C5 129.6(6) . . ? C1 C6 C5 121.7(6) . . ? C16 C7 N1 117.1(5) . . ? C16 C7 C8 131.0(5) . . ? N1 C7 C8 111.6(5) . . ? C9 C8 C13 118.7(6) . . ? C9 C8 C7 120.7(5) . . ? C13 C8 C7 120.7(5) . . ? C8 C9 C10 121.5(6) . . ? C8 C9 H9A 119.2 . . ? C10 C9 H9A 119.2 . . ? C11 C10 C9 120.2(6) . . ? C11 C10 H10A 119.9 . . ? C9 C10 H10A 119.9 . . ? O1 C11 C10 125.3(6) . . ? O1 C11 C12 115.8(5) . . ? C10 C11 C12 118.8(6) . . ? O2 C12 C13 123.6(5) . . ? O2 C12 C11 115.4(5) . . ? C13 C12 C11 121.0(5) . . ? C12 C13 C8 119.7(6) . . ? C12 C13 H13A 120.1 . . ? C8 C13 H13A 120.1 . . ? O1 C14 H14A 109.5 . . ? O1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O2 C15 H15A 109.5 . . ? O2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C7 C16 C17 125.4(5) . . ? C7 C16 I 118.0(4) . . ? C17 C16 I 116.6(4) . . ? C19 C17 C18 63.7(5) . . ? C19 C17 C16 118.9(5) . . ? C18 C17 C16 117.7(6) . . ? C19 C17 H17A 115.5 . . ? C18 C17 H17A 115.5 . . ? C16 C17 H17A 115.5 . . ? C17 C18 C19 57.9(5) . . ? C17 C18 H18A 118.0 . . ? C19 C18 H18A 118.0 . . ? C17 C18 H18B 118.0 . . ? C19 C18 H18B 118.0 . . ? H18A C18 H18B 115.2 . . ? C17 C19 C18 58.4(5) . . ? C17 C19 H19A 117.9 . . ? C18 C19 H19A 117.9 . . ? C17 C19 H19B 117.9 . . ? C18 C19 H19B 117.9 . . ? H19A C19 H19B 115.1 . . ? 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 N3 N1 N2 C1 0.7(7) . . . . ? C7 N1 N2 C1 -176.9(5) . . . . ? C6 C1 N2 N1 0.1(7) . . . . ? C2 C1 N2 N1 178.8(7) . . . . ? N2 C1 C2 C3 -177.6(7) . . . . ? C6 C1 C2 C3 1.0(11) . . . . ? N2 N1 N3 C6 -1.1(7) . . . . ? C7 N1 N3 C6 176.4(5) . . . . ? C1 C2 C3 C4 -1.4(13) . . . . ? C2 C3 C4 C5 1.6(14) . . . . ? C3 C4 C5 C6 -1.2(12) . . . . ? N1 N3 C6 C1 1.1(7) . . . . ? N1 N3 C6 C5 -177.8(7) . . . . ? N2 C1 C6 N3 -0.8(7) . . . . ? C2 C1 C6 N3 -179.7(6) . . . . ? N2 C1 C6 C5 178.2(6) . . . . ? C2 C1 C6 C5 -0.7(10) . . . . ? C4 C5 C6 N3 179.5(7) . . . . ? C4 C5 C6 C1 0.7(10) . . . . ? N2 N1 C7 C16 -95.7(7) . . . . ? N3 N1 C7 C16 86.8(7) . . . . ? N2 N1 C7 C8 89.2(7) . . . . ? N3 N1 C7 C8 -88.2(7) . . . . ? C16 C7 C8 C9 -121.5(8) . . . . ? N1 C7 C8 C9 52.6(8) . . . . ? C16 C7 C8 C13 58.0(10) . . . . ? N1 C7 C8 C13 -127.9(6) . . . . ? C13 C8 C9 C10 -3.7(10) . . . . ? C7 C8 C9 C10 175.8(6) . . . . ? C8 C9 C10 C11 2.5(10) . . . . ? C14 O1 C11 C10 5.1(9) . . . . ? C14 O1 C11 C12 -172.5(6) . . . . ? C9 C10 C11 O1 -177.9(6) . . . . ? C9 C10 C11 C12 -0.4(10) . . . . ? C15 O2 C12 C13 -14.5(10) . . . . ? C15 O2 C12 C11 165.5(6) . . . . ? O1 C11 C12 O2 -2.7(8) . . . . ? C10 C11 C12 O2 179.6(6) . . . . ? O1 C11 C12 C13 177.3(6) . . . . ? C10 C11 C12 C13 -0.4(9) . . . . ? O2 C12 C13 C8 179.2(6) . . . . ? C11 C12 C13 C8 -0.8(10) . . . . ? C9 C8 C13 C12 2.8(9) . . . . ? C7 C8 C13 C12 -176.7(6) . . . . ? N1 C7 C16 C17 3.7(9) . . . . ? C8 C7 C16 C17 177.6(6) . . . . ? N1 C7 C16 I -175.4(4) . . . . ? C8 C7 C16 I -1.6(10) . . . . ? C7 C16 C17 C19 152.3(7) . . . . ? I C16 C17 C19 -28.5(7) . . . . ? C7 C16 C17 C18 -134.1(7) . . . . ? I C16 C17 C18 45.1(7) . . . . ? C16 C17 C18 C19 -110.5(6) . . . . ? C16 C17 C19 C18 108.6(7) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.42 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.773 _refine_diff_density_min -0.693 _refine_diff_density_rms 0.121 # Attachment '20121019.pdf' _database_code_depnum_ccdc_archive 'CCDC 906775' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_b #TrackingRef '20121110.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H36 I2 N6 O4' _chemical_formula_weight 966.59 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.665(2) _cell_length_b 11.535(2) _cell_length_c 18.711(4) _cell_angle_alpha 89.19(3) _cell_angle_beta 82.80(3) _cell_angle_gamma 64.40(3) _cell_volume 2057.4(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 13 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.560 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 1.578 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.7431 _exptl_absorpt_correction_T_max 0.8581 _exptl_absorpt_process_details ? _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 'Nonius cad4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 7996 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0514 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.10 _diffrn_reflns_theta_max 25.38 _reflns_number_total 7556 _reflns_number_gt 5119 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^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 7556 _refine_ls_number_parameters 505 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0946 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1735 _refine_ls_wR_factor_gt 0.1529 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.84166(5) -0.27445(5) 0.91300(3) 0.05893(19) Uani 1 1 d . . . O1 O 1.3882(5) -0.6204(4) 1.0430(3) 0.0538(12) Uani 1 1 d . . . N1 N 1.1324(6) -0.0660(6) 0.8024(3) 0.0510(15) Uani 1 1 d . . . C1 C 1.1991(7) 0.0105(6) 0.8011(4) 0.0479(17) Uani 1 1 d . . . N2 N 1.1946(6) -0.0595(5) 0.9138(3) 0.0535(15) Uani 1 1 d . . . O2 O 1.1672(5) -0.4430(4) 1.1116(3) 0.0536(13) Uani 1 1 d . . . C2 C 1.2280(8) 0.0811(7) 0.7456(5) 0.062(2) Uani 1 1 d . . . H2B H 1.2012 0.0802 0.7003 0.075 Uiso 1 1 calc R . . N3 N 1.1322(5) -0.1023(5) 0.8695(3) 0.0455(14) Uani 1 1 d . . . C3 C 1.2971(10) 0.1515(8) 0.7608(6) 0.082(3) Uani 1 1 d . . . H3A H 1.3185 0.1992 0.7249 0.099 Uiso 1 1 calc R . . C4 C 1.3365(10) 0.1532(9) 0.8293(7) 0.086(3) Uani 1 1 d . . . H4A H 1.3834 0.2027 0.8370 0.103 Uiso 1 1 calc R . . C5 C 1.3105(9) 0.0875(8) 0.8848(6) 0.075(3) Uani 1 1 d . . . H5A H 1.3386 0.0893 0.9297 0.090 Uiso 1 1 calc R . . C6 C 1.2363(7) 0.0146(7) 0.8695(4) 0.0515(18) Uani 1 1 d . . . C7 C 1.0665(7) -0.1825(6) 0.8971(4) 0.0416(15) Uani 1 1 d . . . C8 C 0.9337(7) -0.1485(6) 0.8850(4) 0.0457(16) Uani 1 1 d . . . C9 C 0.8437(7) -0.0308(6) 0.8505(4) 0.0444(16) Uani 1 1 d . . . C10 C 0.7837(9) -0.0374(8) 0.7912(4) 0.063(2) Uani 1 1 d . . . H10A H 0.7986 -0.1173 0.7726 0.076 Uiso 1 1 calc R . . C11 C 0.7009(9) 0.0732(10) 0.7586(5) 0.080(3) Uani 1 1 d . . . H11A H 0.6613 0.0669 0.7181 0.096 Uiso 1 1 calc R . . C12 C 0.6773(9) 0.1906(9) 0.7855(5) 0.071(2) Uani 1 1 d . . . H12A H 0.6236 0.2646 0.7628 0.085 Uiso 1 1 calc R . . C13 C 0.7321(8) 0.1994(8) 0.8453(5) 0.064(2) Uani 1 1 d . . . H13A H 0.7144 0.2800 0.8641 0.077 Uiso 1 1 calc R . . C14 C 0.8146(8) 0.0900(7) 0.8791(4) 0.0550(19) Uani 1 1 d . . . H14A H 0.8503 0.0976 0.9208 0.066 Uiso 1 1 calc R . . C15 C 1.1577(7) -0.2972(6) 0.9350(4) 0.0431(16) Uani 1 1 d . . . C16 C 1.2806(7) -0.3891(7) 0.8994(4) 0.0523(18) Uani 1 1 d . . . H16A H 1.3101 -0.3783 0.8519 0.063 Uiso 1 1 calc R . . C17 C 1.3616(7) -0.4996(7) 0.9347(4) 0.0510(18) Uani 1 1 d . . . H17A H 1.4445 -0.5618 0.9102 0.061 Uiso 1 1 calc R . . C18 C 1.3201(7) -0.5168(6) 1.0045(4) 0.0416(15) Uani 1 1 d . . . C19 C 1.1976(7) -0.4208(6) 1.0413(4) 0.0418(15) Uani 1 1 d . . . C20 C 1.1154(7) -0.3118(6) 1.0070(4) 0.0500(18) Uani 1 1 d . . . H20A H 1.0331 -0.2491 1.0316 0.060 Uiso 1 1 calc R . . C21 C 1.5105(8) -0.7251(7) 1.0073(5) 0.067(2) Uani 1 1 d . . . H21A H 1.5483 -0.7916 1.0406 0.100 Uiso 1 1 calc R . . H21B H 1.5795 -0.6953 0.9899 0.100 Uiso 1 1 calc R . . H21C H 1.4858 -0.7588 0.9675 0.100 Uiso 1 1 calc R . . C22 C 1.0341(9) -0.3585(8) 1.1490(4) 0.071(2) Uani 1 1 d . . . H22A H 1.0257 -0.3847 1.1977 0.106 Uiso 1 1 calc R . . H22B H 0.9610 -0.3616 1.1251 0.106 Uiso 1 1 calc R . . H22C H 1.0257 -0.2722 1.1496 0.106 Uiso 1 1 calc R . . I2 I 0.89588(5) 0.27765(5) 0.61877(3) 0.05832(19) Uani 1 1 d . . . O3 O 0.8580(6) 0.0404(5) 0.3969(3) 0.0703(16) Uani 1 1 d . . . O4 O 0.7673(6) -0.1196(4) 0.4479(3) 0.0673(15) Uani 1 1 d . . . N4 N 0.3878(6) 0.4453(6) 0.6866(3) 0.0488(14) Uani 1 1 d . . . N5 N 0.3619(6) 0.4595(5) 0.5685(3) 0.0443(13) Uani 1 1 d . . . N6 N 0.4484(5) 0.4237(5) 0.6181(3) 0.0398(12) Uani 1 1 d . . . C23 C 0.2488(7) 0.5019(6) 0.6801(4) 0.0460(16) Uani 1 1 d . . . C24 C 0.1316(8) 0.5437(8) 0.7331(4) 0.059(2) Uani 1 1 d . . . H24A H 0.1411 0.5391 0.7819 0.070 Uiso 1 1 calc R . . C25 C 0.0038(8) 0.5912(8) 0.7102(5) 0.066(2) Uani 1 1 d . . . H25A H -0.0759 0.6194 0.7442 0.080 Uiso 1 1 calc R . . C26 C -0.0116(8) 0.5989(7) 0.6363(5) 0.060(2) Uani 1 1 d . . . H26A H -0.1013 0.6310 0.6231 0.072 Uiso 1 1 calc R . . C27 C 0.0998(8) 0.5612(7) 0.5839(4) 0.0557(19) Uani 1 1 d . . . H27A H 0.0884 0.5685 0.5353 0.067 Uiso 1 1 calc R . . C28 C 0.2346(7) 0.5101(6) 0.6067(4) 0.0428(16) Uani 1 1 d . . . C29 C 0.5965(7) 0.3533(6) 0.6005(3) 0.0411(15) Uani 1 1 d . . . C30 C 0.6784(7) 0.3976(6) 0.6272(4) 0.0415(15) Uani 1 1 d . . . C31 C 0.6311(7) 0.5246(6) 0.6640(4) 0.0414(15) Uani 1 1 d . . . C32 C 0.5538(8) 0.6369(7) 0.6294(4) 0.0541(18) Uani 1 1 d . . . H32A H 0.5324 0.6311 0.5833 0.065 Uiso 1 1 calc R . . C33 C 0.5091(9) 0.7565(8) 0.6636(5) 0.069(2) Uani 1 1 d . . . H33A H 0.4593 0.8307 0.6400 0.083 Uiso 1 1 calc R . . C34 C 0.5380(9) 0.7656(8) 0.7317(5) 0.070(2) Uani 1 1 d . . . H34A H 0.5069 0.8460 0.7547 0.084 Uiso 1 1 calc R . . C35 C 0.6139(8) 0.6546(8) 0.7670(5) 0.064(2) Uani 1 1 d . . . H35A H 0.6334 0.6607 0.8135 0.077 Uiso 1 1 calc R . . C36 C 0.6600(8) 0.5354(7) 0.7326(4) 0.0524(18) Uani 1 1 d . . . H36A H 0.7112 0.4615 0.7561 0.063 Uiso 1 1 calc R . . C37 C 0.6372(7) 0.2291(6) 0.5594(4) 0.0406(15) Uani 1 1 d . . . C38 C 0.7291(7) 0.1968(6) 0.4952(4) 0.0464(17) Uani 1 1 d . . . H38A H 0.7628 0.2546 0.4765 0.056 Uiso 1 1 calc R . . C39 C 0.7709(7) 0.0796(6) 0.4591(4) 0.0461(16) Uani 1 1 d . . . C40 C 0.7197(7) -0.0069(6) 0.4873(4) 0.0482(17) Uani 1 1 d . . . C41 C 0.6278(8) 0.0262(7) 0.5490(4) 0.0517(18) Uani 1 1 d . . . H41A H 0.5928 -0.0310 0.5671 0.062 Uiso 1 1 calc R . . C42 C 0.5841(7) 0.1459(7) 0.5862(4) 0.0513(18) Uani 1 1 d . . . H42A H 0.5205 0.1678 0.6282 0.062 Uiso 1 1 calc R . . C43 C 0.9312(12) 0.1150(10) 0.3712(5) 0.095(4) Uani 1 1 d . . . H43A H 0.9889 0.0768 0.3264 0.142 Uiso 1 1 calc R . . H43B H 0.9891 0.1170 0.4061 0.142 Uiso 1 1 calc R . . H43C H 0.8646 0.2012 0.3638 0.142 Uiso 1 1 calc R . . C44 C 0.7455(9) -0.2224(7) 0.4806(6) 0.075(3) Uani 1 1 d . . . H44A H 0.7835 -0.2955 0.4472 0.112 Uiso 1 1 calc R . . H44B H 0.6468 -0.1961 0.4935 0.112 Uiso 1 1 calc R . . H44C H 0.7915 -0.2449 0.5231 0.112 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 0.0652(4) 0.0654(4) 0.0665(4) 0.0110(3) -0.0136(3) -0.0461(3) O1 0.049(3) 0.043(3) 0.066(3) 0.014(2) -0.012(2) -0.016(2) N1 0.053(4) 0.051(4) 0.052(4) 0.011(3) -0.005(3) -0.027(3) C1 0.038(4) 0.042(4) 0.061(5) -0.001(3) 0.006(3) -0.018(3) N2 0.051(4) 0.048(4) 0.070(4) 0.002(3) -0.018(3) -0.026(3) O2 0.054(3) 0.040(3) 0.060(3) 0.012(2) -0.003(2) -0.015(2) C2 0.063(5) 0.050(5) 0.065(5) 0.000(4) 0.013(4) -0.021(4) N3 0.038(3) 0.038(3) 0.065(4) 0.008(3) -0.011(3) -0.019(3) C3 0.082(7) 0.062(6) 0.099(8) 0.001(5) 0.034(6) -0.040(5) C4 0.076(6) 0.082(7) 0.116(9) -0.009(6) 0.015(6) -0.057(6) C5 0.062(5) 0.078(6) 0.104(7) -0.010(5) -0.002(5) -0.051(5) C6 0.042(4) 0.050(4) 0.066(5) -0.003(4) 0.002(4) -0.025(3) C7 0.042(4) 0.038(4) 0.049(4) 0.007(3) -0.008(3) -0.022(3) C8 0.052(4) 0.046(4) 0.047(4) 0.003(3) -0.003(3) -0.030(3) C9 0.035(3) 0.050(4) 0.051(4) 0.009(3) -0.004(3) -0.021(3) C10 0.064(5) 0.059(5) 0.064(5) 0.004(4) -0.023(4) -0.020(4) C11 0.064(6) 0.098(8) 0.072(6) 0.012(6) -0.027(5) -0.026(5) C12 0.058(5) 0.076(6) 0.072(6) 0.032(5) -0.011(4) -0.023(5) C13 0.058(5) 0.050(5) 0.080(6) 0.011(4) -0.007(4) -0.020(4) C14 0.053(4) 0.047(4) 0.067(5) 0.007(4) -0.017(4) -0.022(4) C15 0.044(4) 0.038(4) 0.053(4) 0.004(3) -0.011(3) -0.022(3) C16 0.045(4) 0.055(4) 0.059(5) 0.008(4) 0.000(3) -0.025(4) C17 0.038(4) 0.047(4) 0.067(5) 0.001(4) -0.007(3) -0.017(3) C18 0.038(4) 0.038(4) 0.052(4) 0.007(3) -0.007(3) -0.020(3) C19 0.041(4) 0.033(3) 0.057(4) 0.008(3) -0.008(3) -0.022(3) C20 0.046(4) 0.036(4) 0.067(5) -0.001(3) -0.007(4) -0.017(3) C21 0.047(4) 0.037(4) 0.100(7) 0.011(4) -0.009(4) -0.004(3) C22 0.067(5) 0.064(5) 0.062(5) 0.002(4) 0.021(4) -0.018(4) I2 0.0366(3) 0.0578(3) 0.0759(4) -0.0050(3) -0.0102(2) -0.0151(2) O3 0.086(4) 0.053(3) 0.072(4) -0.025(3) 0.027(3) -0.039(3) O4 0.072(4) 0.033(3) 0.100(4) -0.009(3) -0.008(3) -0.026(3) N4 0.045(3) 0.059(4) 0.047(4) -0.001(3) -0.006(3) -0.027(3) N5 0.042(3) 0.043(3) 0.050(3) -0.004(3) -0.012(3) -0.019(3) N6 0.039(3) 0.043(3) 0.039(3) -0.005(2) -0.005(3) -0.019(3) C23 0.043(4) 0.045(4) 0.053(4) -0.006(3) -0.006(3) -0.022(3) C24 0.050(5) 0.071(5) 0.056(5) 0.000(4) 0.001(4) -0.029(4) C25 0.040(4) 0.059(5) 0.088(7) -0.003(4) 0.016(4) -0.017(4) C26 0.039(4) 0.051(5) 0.087(6) 0.002(4) -0.010(4) -0.017(3) C27 0.058(5) 0.058(5) 0.058(5) 0.002(4) -0.019(4) -0.028(4) C28 0.039(4) 0.034(3) 0.055(4) -0.001(3) -0.008(3) -0.015(3) C29 0.037(4) 0.040(4) 0.043(4) -0.004(3) -0.006(3) -0.013(3) C30 0.037(4) 0.040(4) 0.045(4) -0.002(3) -0.006(3) -0.014(3) C31 0.038(4) 0.041(4) 0.045(4) -0.004(3) -0.002(3) -0.018(3) C32 0.058(5) 0.048(4) 0.055(5) -0.001(3) -0.016(4) -0.020(4) C33 0.062(5) 0.044(4) 0.089(7) -0.006(4) -0.017(5) -0.010(4) C34 0.059(5) 0.056(5) 0.091(7) -0.030(5) -0.001(5) -0.024(4) C35 0.055(5) 0.078(6) 0.063(5) -0.019(4) -0.011(4) -0.030(4) C36 0.054(4) 0.051(4) 0.055(5) -0.002(4) -0.015(4) -0.022(4) C37 0.043(4) 0.032(3) 0.047(4) -0.003(3) -0.013(3) -0.015(3) C38 0.049(4) 0.037(4) 0.056(4) 0.000(3) -0.002(3) -0.022(3) C39 0.042(4) 0.041(4) 0.052(4) -0.004(3) 0.000(3) -0.017(3) C40 0.048(4) 0.037(4) 0.065(5) -0.003(3) -0.011(4) -0.023(3) C41 0.057(5) 0.050(4) 0.064(5) 0.005(4) -0.013(4) -0.036(4) C42 0.049(4) 0.058(5) 0.055(4) -0.004(4) -0.004(3) -0.032(4) C43 0.123(9) 0.093(7) 0.081(7) -0.032(5) 0.046(6) -0.073(7) C44 0.066(5) 0.036(4) 0.125(8) 0.000(5) -0.026(5) -0.022(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 I1 C8 2.104(6) . ? O1 C18 1.353(8) . ? O1 C21 1.432(8) . ? N1 N3 1.318(8) . ? N1 C1 1.351(9) . ? C1 C6 1.393(10) . ? C1 C2 1.396(10) . ? N2 N3 1.344(8) . ? N2 C6 1.352(9) . ? O2 C19 1.362(8) . ? O2 C22 1.425(8) . ? C2 C3 1.363(13) . ? C2 H2B 0.9300 . ? N3 C7 1.439(8) . ? C3 C4 1.403(14) . ? C3 H3A 0.9300 . ? C4 C5 1.349(13) . ? C4 H4A 0.9300 . ? C5 C6 1.433(10) . ? C5 H5A 0.9300 . ? C7 C8 1.345(9) . ? C7 C15 1.495(9) . ? C8 C9 1.479(9) . ? C9 C10 1.368(10) . ? C9 C14 1.389(10) . ? C10 C11 1.385(12) . ? C10 H10A 0.9300 . ? C11 C12 1.359(13) . ? C11 H11A 0.9300 . ? C12 C13 1.350(12) . ? C12 H12A 0.9300 . ? C13 C14 1.387(10) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.373(9) . ? C15 C20 1.397(10) . ? C16 C17 1.406(10) . ? C16 H16A 0.9300 . ? C17 C18 1.366(10) . ? C17 H17A 0.9300 . ? C18 C19 1.398(9) . ? C19 C20 1.389(9) . ? C20 H20A 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? I2 C30 2.112(6) . ? O3 C39 1.342(8) . ? O3 C43 1.434(10) . ? O4 C40 1.361(8) . ? O4 C44 1.420(9) . ? N4 N6 1.335(7) . ? N4 C23 1.358(8) . ? N5 N6 1.327(7) . ? N5 C28 1.334(8) . ? N6 C29 1.425(8) . ? C23 C28 1.399(9) . ? C23 C24 1.399(10) . ? C24 C25 1.355(11) . ? C24 H24A 0.9300 . ? C25 C26 1.410(12) . ? C25 H25A 0.9300 . ? C26 C27 1.355(10) . ? C26 H26A 0.9300 . ? C27 C28 1.418(9) . ? C27 H27A 0.9300 . ? C29 C30 1.334(9) . ? C29 C37 1.496(9) . ? C30 C31 1.475(9) . ? C31 C36 1.377(9) . ? C31 C32 1.401(9) . ? C32 C33 1.385(10) . ? C32 H32A 0.9300 . ? C33 C34 1.365(12) . ? C33 H33A 0.9300 . ? C34 C35 1.395(12) . ? C34 H34A 0.9300 . ? C35 C36 1.381(10) . ? C35 H35A 0.9300 . ? C36 H36A 0.9300 . ? C37 C42 1.369(9) . ? C37 C38 1.395(9) . ? C38 C39 1.383(9) . ? C38 H38A 0.9300 . ? C39 C40 1.399(9) . ? C40 C41 1.357(10) . ? C41 C42 1.414(10) . ? C41 H41A 0.9300 . ? C42 H42A 0.9300 . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? 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 C18 O1 C21 118.2(6) . . ? N3 N1 C1 103.1(6) . . ? N1 C1 C6 108.1(6) . . ? N1 C1 C2 130.5(8) . . ? C6 C1 C2 121.3(7) . . ? N3 N2 C6 101.3(6) . . ? C19 O2 C22 117.8(5) . . ? C3 C2 C1 117.1(9) . . ? C3 C2 H2B 121.4 . . ? C1 C2 H2B 121.4 . . ? N1 N3 N2 117.5(6) . . ? N1 N3 C7 123.1(6) . . ? N2 N3 C7 119.4(6) . . ? C2 C3 C4 121.2(8) . . ? C2 C3 H3A 119.4 . . ? C4 C3 H3A 119.4 . . ? C5 C4 C3 124.0(9) . . ? C5 C4 H4A 118.0 . . ? C3 C4 H4A 118.0 . . ? C4 C5 C6 115.0(9) . . ? C4 C5 H5A 122.5 . . ? C6 C5 H5A 122.5 . . ? N2 C6 C1 110.0(6) . . ? N2 C6 C5 128.8(8) . . ? C1 C6 C5 121.3(7) . . ? C8 C7 N3 117.6(6) . . ? C8 C7 C15 127.6(6) . . ? N3 C7 C15 114.8(5) . . ? C7 C8 C9 126.3(6) . . ? C7 C8 I1 118.9(5) . . ? C9 C8 I1 114.8(5) . . ? C10 C9 C14 118.2(7) . . ? C10 C9 C8 121.2(7) . . ? C14 C9 C8 120.6(6) . . ? C9 C10 C11 121.0(8) . . ? C9 C10 H10A 119.5 . . ? C11 C10 H10A 119.5 . . ? C12 C11 C10 120.2(9) . . ? C12 C11 H11A 119.9 . . ? C10 C11 H11A 119.9 . . ? C13 C12 C11 119.7(8) . . ? C13 C12 H12A 120.1 . . ? C11 C12 H12A 120.1 . . ? C12 C13 C14 121.0(8) . . ? C12 C13 H13A 119.5 . . ? C14 C13 H13A 119.5 . . ? C13 C14 C9 119.7(8) . . ? C13 C14 H14A 120.1 . . ? C9 C14 H14A 120.1 . . ? C16 C15 C20 120.0(6) . . ? C16 C15 C7 120.7(6) . . ? C20 C15 C7 119.3(6) . . ? C15 C16 C17 120.0(7) . . ? C15 C16 H16A 120.0 . . ? C17 C16 H16A 120.0 . . ? C18 C17 C16 120.8(7) . . ? C18 C17 H17A 119.6 . . ? C16 C17 H17A 119.6 . . ? O1 C18 C17 125.6(6) . . ? O1 C18 C19 115.4(6) . . ? C17 C18 C19 119.0(6) . . ? O2 C19 C20 123.9(6) . . ? O2 C19 C18 115.2(5) . . ? C20 C19 C18 120.9(6) . . ? C19 C20 C15 119.3(6) . . ? C19 C20 H20A 120.3 . . ? C15 C20 H20A 120.3 . . ? O1 C21 H21A 109.5 . . ? O1 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O1 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O2 C22 H22A 109.5 . . ? O2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C39 O3 C43 118.1(6) . . ? C40 O4 C44 117.9(7) . . ? N6 N4 C23 103.0(5) . . ? N6 N5 C28 103.9(5) . . ? N5 N6 N4 115.9(5) . . ? N5 N6 C29 122.5(5) . . ? N4 N6 C29 121.2(5) . . ? N4 C23 C28 108.2(6) . . ? N4 C23 C24 130.3(7) . . ? C28 C23 C24 121.4(6) . . ? C25 C24 C23 117.2(7) . . ? C25 C24 H24A 121.4 . . ? C23 C24 H24A 121.4 . . ? C24 C25 C26 121.8(7) . . ? C24 C25 H25A 119.1 . . ? C26 C25 H25A 119.1 . . ? C27 C26 C25 122.3(7) . . ? C27 C26 H26A 118.9 . . ? C25 C26 H26A 118.9 . . ? C26 C27 C28 116.8(7) . . ? C26 C27 H27A 121.6 . . ? C28 C27 H27A 121.6 . . ? N5 C28 C23 108.9(6) . . ? N5 C28 C27 130.5(7) . . ? C23 C28 C27 120.5(6) . . ? C30 C29 N6 118.1(6) . . ? C30 C29 C37 129.0(6) . . ? N6 C29 C37 112.6(5) . . ? C29 C30 C31 125.9(6) . . ? C29 C30 I2 118.6(5) . . ? C31 C30 I2 115.5(4) . . ? C36 C31 C32 118.8(6) . . ? C36 C31 C30 121.1(6) . . ? C32 C31 C30 120.1(6) . . ? C33 C32 C31 120.4(7) . . ? C33 C32 H32A 119.8 . . ? C31 C32 H32A 119.8 . . ? C34 C33 C32 120.1(8) . . ? C34 C33 H33A 119.9 . . ? C32 C33 H33A 119.9 . . ? C33 C34 C35 120.2(7) . . ? C33 C34 H34A 119.9 . . ? C35 C34 H34A 119.9 . . ? C36 C35 C34 119.7(8) . . ? C36 C35 H35A 120.2 . . ? C34 C35 H35A 120.2 . . ? C31 C36 C35 120.9(7) . . ? C31 C36 H36A 119.6 . . ? C35 C36 H36A 119.6 . . ? C42 C37 C38 120.0(6) . . ? C42 C37 C29 119.1(6) . . ? C38 C37 C29 120.9(6) . . ? C39 C38 C37 120.7(6) . . ? C39 C38 H38A 119.6 . . ? C37 C38 H38A 119.6 . . ? O3 C39 C38 125.0(6) . . ? O3 C39 C40 115.5(6) . . ? C38 C39 C40 119.4(6) . . ? C41 C40 O4 125.5(6) . . ? C41 C40 C39 119.6(6) . . ? O4 C40 C39 114.9(6) . . ? C40 C41 C42 121.4(7) . . ? C40 C41 H41A 119.3 . . ? C42 C41 H41A 119.3 . . ? C37 C42 C41 118.8(7) . . ? C37 C42 H42A 120.6 . . ? C41 C42 H42A 120.6 . . ? O3 C43 H43A 109.5 . . ? O3 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? O3 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? O4 C44 H44A 109.5 . . ? O4 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? O4 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? 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 N3 N1 C1 C6 0.3(7) . . . . ? N3 N1 C1 C2 -177.7(7) . . . . ? N1 C1 C2 C3 179.4(7) . . . . ? C6 C1 C2 C3 1.6(11) . . . . ? C1 N1 N3 N2 -1.1(8) . . . . ? C1 N1 N3 C7 177.6(6) . . . . ? C6 N2 N3 N1 1.4(8) . . . . ? C6 N2 N3 C7 -177.4(6) . . . . ? C1 C2 C3 C4 -0.4(13) . . . . ? C2 C3 C4 C5 0.0(15) . . . . ? C3 C4 C5 C6 -0.8(14) . . . . ? N3 N2 C6 C1 -1.0(7) . . . . ? N3 N2 C6 C5 -179.7(8) . . . . ? N1 C1 C6 N2 0.5(8) . . . . ? C2 C1 C6 N2 178.7(7) . . . . ? N1 C1 C6 C5 179.3(7) . . . . ? C2 C1 C6 C5 -2.4(11) . . . . ? C4 C5 C6 N2 -179.5(8) . . . . ? C4 C5 C6 C1 1.9(12) . . . . ? N1 N3 C7 C8 -49.8(9) . . . . ? N2 N3 C7 C8 128.9(7) . . . . ? N1 N3 C7 C15 129.0(6) . . . . ? N2 N3 C7 C15 -52.3(8) . . . . ? N3 C7 C8 C9 -4.8(11) . . . . ? C15 C7 C8 C9 176.6(7) . . . . ? N3 C7 C8 I1 172.6(5) . . . . ? C15 C7 C8 I1 -5.9(10) . . . . ? C7 C8 C9 C10 124.2(8) . . . . ? I1 C8 C9 C10 -53.4(8) . . . . ? C7 C8 C9 C14 -57.8(10) . . . . ? I1 C8 C9 C14 124.6(6) . . . . ? C14 C9 C10 C11 2.8(12) . . . . ? C8 C9 C10 C11 -179.2(8) . . . . ? C9 C10 C11 C12 -0.4(14) . . . . ? C10 C11 C12 C13 -1.6(14) . . . . ? C11 C12 C13 C14 1.2(13) . . . . ? C12 C13 C14 C9 1.2(12) . . . . ? C10 C9 C14 C13 -3.1(11) . . . . ? C8 C9 C14 C13 178.8(7) . . . . ? C8 C7 C15 C16 118.1(8) . . . . ? N3 C7 C15 C16 -60.4(9) . . . . ? C8 C7 C15 C20 -60.4(10) . . . . ? N3 C7 C15 C20 121.0(7) . . . . ? C20 C15 C16 C17 1.8(11) . . . . ? C7 C15 C16 C17 -176.8(6) . . . . ? C15 C16 C17 C18 -0.3(11) . . . . ? C21 O1 C18 C17 -3.7(10) . . . . ? C21 O1 C18 C19 176.8(6) . . . . ? C16 C17 C18 O1 178.5(7) . . . . ? C16 C17 C18 C19 -2.0(10) . . . . ? C22 O2 C19 C20 9.0(10) . . . . ? C22 O2 C19 C18 -171.1(6) . . . . ? O1 C18 C19 O2 2.4(9) . . . . ? C17 C18 C19 O2 -177.1(6) . . . . ? O1 C18 C19 C20 -177.7(6) . . . . ? C17 C18 C19 C20 2.8(10) . . . . ? O2 C19 C20 C15 178.7(6) . . . . ? C18 C19 C20 C15 -1.2(10) . . . . ? C16 C15 C20 C19 -1.1(10) . . . . ? C7 C15 C20 C19 177.5(6) . . . . ? C28 N5 N6 N4 0.8(7) . . . . ? C28 N5 N6 C29 173.9(6) . . . . ? C23 N4 N6 N5 -0.8(7) . . . . ? C23 N4 N6 C29 -173.9(6) . . . . ? N6 N4 C23 C28 0.4(7) . . . . ? N6 N4 C23 C24 177.9(7) . . . . ? N4 C23 C24 C25 -176.5(7) . . . . ? C28 C23 C24 C25 0.7(11) . . . . ? C23 C24 C25 C26 -0.2(12) . . . . ? C24 C25 C26 C27 -0.9(13) . . . . ? C25 C26 C27 C28 1.5(11) . . . . ? N6 N5 C28 C23 -0.4(7) . . . . ? N6 N5 C28 C27 -177.8(7) . . . . ? N4 C23 C28 N5 0.0(8) . . . . ? C24 C23 C28 N5 -177.7(7) . . . . ? N4 C23 C28 C27 177.7(6) . . . . ? C24 C23 C28 C27 -0.1(10) . . . . ? C26 C27 C28 N5 176.1(7) . . . . ? C26 C27 C28 C23 -1.0(10) . . . . ? N5 N6 C29 C30 128.7(7) . . . . ? N4 N6 C29 C30 -58.6(9) . . . . ? N5 N6 C29 C37 -57.5(8) . . . . ? N4 N6 C29 C37 115.2(6) . . . . ? N6 C29 C30 C31 -10.8(10) . . . . ? C37 C29 C30 C31 176.6(7) . . . . ? N6 C29 C30 I2 168.4(4) . . . . ? C37 C29 C30 I2 -4.3(10) . . . . ? C29 C30 C31 C36 123.6(8) . . . . ? I2 C30 C31 C36 -55.6(8) . . . . ? C29 C30 C31 C32 -55.5(10) . . . . ? I2 C30 C31 C32 125.3(6) . . . . ? C36 C31 C32 C33 0.8(11) . . . . ? C30 C31 C32 C33 -180.0(7) . . . . ? C31 C32 C33 C34 -1.2(13) . . . . ? C32 C33 C34 C35 0.7(13) . . . . ? C33 C34 C35 C36 0.1(13) . . . . ? C32 C31 C36 C35 0.0(11) . . . . ? C30 C31 C36 C35 -179.2(7) . . . . ? C34 C35 C36 C31 -0.5(12) . . . . ? C30 C29 C37 C42 121.4(8) . . . . ? N6 C29 C37 C42 -51.6(8) . . . . ? C30 C29 C37 C38 -57.8(10) . . . . ? N6 C29 C37 C38 129.2(7) . . . . ? C42 C37 C38 C39 -1.8(10) . . . . ? C29 C37 C38 C39 177.3(6) . . . . ? C43 O3 C39 C38 10.3(12) . . . . ? C43 O3 C39 C40 -170.3(8) . . . . ? C37 C38 C39 O3 179.6(7) . . . . ? C37 C38 C39 C40 0.2(11) . . . . ? C44 O4 C40 C41 -14.8(11) . . . . ? C44 O4 C40 C39 166.4(7) . . . . ? O3 C39 C40 C41 -178.2(7) . . . . ? C38 C39 C40 C41 1.3(11) . . . . ? O3 C39 C40 O4 0.7(10) . . . . ? C38 C39 C40 O4 -179.8(6) . . . . ? O4 C40 C41 C42 -179.9(7) . . . . ? C39 C40 C41 C42 -1.1(11) . . . . ? C38 C37 C42 C41 2.0(10) . . . . ? C29 C37 C42 C41 -177.2(6) . . . . ? C40 C41 C42 C37 -0.5(11) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.38 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.183 _refine_diff_density_min -1.581 _refine_diff_density_rms 0.122 # Attachment '20121110.pdf' _database_code_depnum_ccdc_archive 'CCDC 910377' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_b #TrackingRef '20120921.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 I N3 O Si' _chemical_formula_weight 475.40 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' Si Si 0.0817 0.0704 '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 Monoclinic _symmetry_space_group_name_H-M P21/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.3720(17) _cell_length_b 16.816(3) _cell_length_c 15.350(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.16(3) _cell_angle_gamma 90.00 _cell_volume 2155.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 13 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 1.554 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.7463 _exptl_absorpt_correction_T_max 0.8601 _exptl_absorpt_process_details ? _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 'Nonious CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 4254 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_av_sigmaI/netI 0.0765 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.38 _reflns_number_total 3968 _reflns_number_gt 2120 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0500P)^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 3968 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1245 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1284 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I I 0.26632(7) 0.72667(3) 0.86551(4) 0.0828(2) Uani 1 1 d . . . Si Si 0.5103(2) 0.74770(10) 0.70191(12) 0.0526(5) Uani 1 1 d . . . O1 O 0.8164(6) 0.4245(3) 0.5576(3) 0.0649(13) Uani 1 1 d . . . N1 N 0.1691(6) 0.5282(3) 0.8057(4) 0.0578(15) Uani 1 1 d . . . C1 C 0.2771(9) 0.4125(4) 0.9972(4) 0.075(2) Uani 1 1 d . . . H1B H 0.3695 0.4034 1.0333 0.090 Uiso 1 1 calc R . . N2 N 0.3212(6) 0.5439(3) 0.8242(3) 0.0445(12) Uani 1 1 d . . . C2 C 0.1381(10) 0.3779(4) 1.0113(4) 0.068(2) Uani 1 1 d . . . H2A H 0.1337 0.3440 1.0590 0.081 Uiso 1 1 calc R . . N3 N 0.3942(7) 0.5071(3) 0.8917(4) 0.0579(15) Uani 1 1 d . . . C3 C 0.0010(10) 0.3902(4) 0.9583(5) 0.075(2) Uani 1 1 d . . . H3B H -0.0918 0.3639 0.9716 0.090 Uiso 1 1 calc R . . C4 C -0.0062(9) 0.4390(4) 0.8874(5) 0.069(2) Uani 1 1 d . . . H4A H -0.1007 0.4471 0.8529 0.083 Uiso 1 1 calc R . . C5 C 0.1373(8) 0.4762(4) 0.8695(4) 0.0508(16) Uani 1 1 d . . . C6 C 0.2755(8) 0.4645(4) 0.9233(4) 0.0538(17) Uani 1 1 d . . . C7 C 0.4175(7) 0.5937(3) 0.7702(4) 0.0433(15) Uani 1 1 d . . . C8 C 0.5233(7) 0.5481(3) 0.7152(4) 0.0431(15) Uani 1 1 d . . . C9 C 0.6854(8) 0.5543(3) 0.7319(4) 0.0532(17) Uani 1 1 d . . . H9A H 0.7263 0.5860 0.7778 0.064 Uiso 1 1 calc R . . C10 C 0.7914(7) 0.5135(4) 0.6808(4) 0.0471(16) Uani 1 1 d . . . H10A H 0.9016 0.5189 0.6915 0.056 Uiso 1 1 calc R . . C11 C 0.7288(8) 0.4659(3) 0.6151(4) 0.0461(16) Uani 1 1 d . . . C12 C 0.5641(9) 0.4580(4) 0.5990(4) 0.0591(18) Uani 1 1 d . . . H12A H 0.5223 0.4258 0.5537 0.071 Uiso 1 1 calc R . . C13 C 0.4635(8) 0.4981(4) 0.6508(4) 0.0536(17) Uani 1 1 d . . . H13A H 0.3534 0.4910 0.6418 0.064 Uiso 1 1 calc R . . C14 C 0.9855(8) 0.4173(4) 0.5791(4) 0.0632(19) Uani 1 1 d . . . H14A H 1.0053 0.3940 0.6367 0.076 Uiso 1 1 calc R . . H14B H 1.0357 0.4693 0.5792 0.076 Uiso 1 1 calc R . . C15 C 0.4062(7) 0.6733(3) 0.7723(4) 0.0468(16) Uani 1 1 d . . . C20 C 0.6944(9) 0.7825(4) 0.7656(5) 0.094(3) Uani 1 1 d . . . H20A H 0.7497 0.8200 0.7314 0.142 Uiso 1 1 calc R . . H20B H 0.7630 0.7380 0.7799 0.142 Uiso 1 1 calc R . . H20C H 0.6657 0.8076 0.8184 0.142 Uiso 1 1 calc R . . C19 C 0.5564(8) 0.7050(4) 0.5963(4) 0.067(2) Uani 1 1 d . . . H19A H 0.6090 0.7442 0.5631 0.100 Uiso 1 1 calc R . . H19B H 0.4589 0.6886 0.5646 0.100 Uiso 1 1 calc R . . H19C H 0.6255 0.6598 0.6062 0.100 Uiso 1 1 calc R . . C18 C 0.3699(9) 0.8318(4) 0.6767(5) 0.075(2) Uani 1 1 d . . . H18A H 0.4199 0.8701 0.6410 0.113 Uiso 1 1 calc R . . H18B H 0.3434 0.8566 0.7301 0.113 Uiso 1 1 calc R . . H18C H 0.2741 0.8122 0.6458 0.113 Uiso 1 1 calc R . . C16 C 0.9760(12) 0.3342(5) 0.4456(7) 0.115(4) Uani 1 1 d . . . H16A H 0.8667 0.3431 0.4348 0.138 Uiso 1 1 calc R . . H16C H 1.0303 0.3026 0.4078 0.138 Uiso 1 1 calc R . . C17 C 1.0524(11) 0.3659(5) 0.5129(6) 0.091(3) Uani 1 1 d . . . H15A H 1.1614 0.3551 0.5205 0.109 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 I 0.1132(5) 0.0530(3) 0.0881(4) -0.0147(3) 0.0473(3) 0.0002(3) Si 0.0584(11) 0.0382(10) 0.0613(11) 0.0020(8) 0.0059(9) -0.0014(9) O1 0.068(3) 0.063(3) 0.067(3) -0.002(2) 0.018(3) 0.011(3) N1 0.038(3) 0.060(4) 0.074(4) 0.010(3) -0.004(3) -0.009(3) C1 0.079(5) 0.086(6) 0.056(5) 0.024(4) -0.020(4) -0.023(5) N2 0.049(3) 0.040(3) 0.044(3) 0.005(2) 0.000(3) -0.001(3) C2 0.087(6) 0.067(5) 0.048(4) 0.011(4) -0.003(4) -0.027(4) N3 0.057(4) 0.060(4) 0.057(4) 0.004(3) 0.008(3) -0.011(3) C3 0.078(5) 0.075(5) 0.071(5) 0.011(4) 0.003(5) -0.035(5) C4 0.061(5) 0.078(5) 0.066(5) 0.019(4) -0.011(4) -0.025(4) C5 0.055(4) 0.048(4) 0.048(4) 0.011(3) -0.001(3) -0.015(3) C6 0.063(4) 0.046(4) 0.053(4) 0.000(3) 0.008(4) -0.014(4) C7 0.044(4) 0.039(3) 0.047(4) 0.004(3) 0.002(3) 0.002(3) C8 0.045(4) 0.032(3) 0.052(4) 0.003(3) 0.002(3) -0.001(3) C9 0.070(5) 0.041(4) 0.048(4) -0.004(3) 0.001(4) -0.004(3) C10 0.036(4) 0.051(4) 0.056(4) 0.006(3) 0.009(3) -0.006(3) C11 0.062(5) 0.038(3) 0.040(4) 0.009(3) 0.011(4) 0.001(4) C12 0.068(5) 0.045(4) 0.063(5) -0.009(3) 0.000(4) 0.003(4) C13 0.049(4) 0.046(4) 0.066(4) -0.007(3) 0.002(4) -0.003(3) C14 0.061(5) 0.062(5) 0.068(5) 0.007(4) 0.013(4) 0.008(4) C15 0.055(4) 0.040(4) 0.046(4) -0.007(3) 0.004(3) 0.000(3) C20 0.091(6) 0.072(6) 0.118(7) 0.018(5) -0.010(5) -0.029(5) C19 0.080(5) 0.049(4) 0.074(5) 0.016(3) 0.019(4) 0.011(4) C18 0.096(6) 0.052(4) 0.079(5) 0.006(4) 0.010(5) 0.012(4) C16 0.123(9) 0.080(7) 0.150(10) -0.031(7) 0.071(8) -0.002(6) C17 0.080(6) 0.074(6) 0.122(8) 0.003(5) 0.037(6) 0.026(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 I C15 2.113(6) . ? Si C19 1.839(6) . ? Si C20 1.859(8) . ? Si C18 1.862(7) . ? Si C15 1.905(6) . ? O1 C11 1.378(7) . ? O1 C14 1.435(7) . ? N1 N2 1.312(6) . ? N1 C5 1.354(7) . ? C1 C2 1.332(9) . ? C1 C6 1.433(8) . ? C1 H1B 0.9300 . ? N2 N3 1.319(6) . ? N2 C7 1.460(7) . ? C2 C3 1.374(9) . ? C2 H2A 0.9300 . ? N3 C6 1.344(7) . ? C3 C4 1.360(9) . ? C3 H3B 0.9300 . ? C4 C5 1.399(9) . ? C4 H4A 0.9300 . ? C5 C6 1.386(8) . ? C7 C15 1.343(8) . ? C7 C8 1.481(7) . ? C8 C13 1.365(8) . ? C8 C9 1.367(8) . ? C9 C10 1.404(8) . ? C9 H9A 0.9300 . ? C10 C11 1.362(8) . ? C10 H10A 0.9300 . ? C11 C12 1.389(8) . ? C12 C13 1.376(8) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 C17 1.474(10) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C16 C17 1.290(11) . ? C16 H16A 0.9300 . ? C16 H16C 0.9300 . ? C17 H15A 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 C19 Si C20 111.5(4) . . ? C19 Si C18 106.5(3) . . ? C20 Si C18 110.9(3) . . ? C19 Si C15 112.2(3) . . ? C20 Si C15 107.7(3) . . ? C18 Si C15 108.0(3) . . ? C11 O1 C14 117.2(5) . . ? N2 N1 C5 102.3(5) . . ? C2 C1 C6 115.9(7) . . ? C2 C1 H1B 122.0 . . ? C6 C1 H1B 122.0 . . ? N1 N2 N3 117.6(5) . . ? N1 N2 C7 124.1(5) . . ? N3 N2 C7 118.1(5) . . ? C1 C2 C3 122.7(7) . . ? C1 C2 H2A 118.7 . . ? C3 C2 H2A 118.7 . . ? N2 N3 C6 102.8(5) . . ? C4 C3 C2 123.5(7) . . ? C4 C3 H3B 118.3 . . ? C2 C3 H3B 118.3 . . ? C3 C4 C5 116.0(7) . . ? C3 C4 H4A 122.0 . . ? C5 C4 H4A 122.0 . . ? N1 C5 C6 108.9(5) . . ? N1 C5 C4 130.4(6) . . ? C6 C5 C4 120.7(6) . . ? N3 C6 C5 108.5(6) . . ? N3 C6 C1 130.3(7) . . ? C5 C6 C1 121.2(6) . . ? C15 C7 N2 121.0(5) . . ? C15 C7 C8 125.2(5) . . ? N2 C7 C8 113.8(5) . . ? C13 C8 C9 119.3(6) . . ? C13 C8 C7 121.9(6) . . ? C9 C8 C7 118.8(6) . . ? C8 C9 C10 121.2(6) . . ? C8 C9 H9A 119.4 . . ? C10 C9 H9A 119.4 . . ? C11 C10 C9 118.4(6) . . ? C11 C10 H10A 120.8 . . ? C9 C10 H10A 120.8 . . ? C10 C11 O1 125.3(6) . . ? C10 C11 C12 120.8(6) . . ? O1 C11 C12 113.9(6) . . ? C13 C12 C11 119.4(6) . . ? C13 C12 H12A 120.3 . . ? C11 C12 H12A 120.3 . . ? C8 C13 C12 120.9(6) . . ? C8 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? O1 C14 C17 107.9(6) . . ? O1 C14 H14A 110.1 . . ? C17 C14 H14A 110.1 . . ? O1 C14 H14B 110.1 . . ? C17 C14 H14B 110.1 . . ? H14A C14 H14B 108.4 . . ? C7 C15 Si 127.2(4) . . ? C7 C15 I 118.9(4) . . ? Si C15 I 113.8(3) . . ? Si C20 H20A 109.5 . . ? Si C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? Si C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? Si C19 H19A 109.5 . . ? Si C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? Si C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? Si C18 H18A 109.5 . . ? Si C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? Si C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C16 H16A 120.0 . . ? C17 C16 H16C 120.0 . . ? H16A C16 H16C 120.0 . . ? C16 C17 C14 127.1(9) . . ? C16 C17 H15A 116.5 . . ? C14 C17 H15A 116.5 . . ? 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 C5 N1 N2 N3 1.4(7) . . . . ? C5 N1 N2 C7 175.5(5) . . . . ? C6 C1 C2 C3 0.5(11) . . . . ? N1 N2 N3 C6 -2.4(7) . . . . ? C7 N2 N3 C6 -176.9(5) . . . . ? C1 C2 C3 C4 -0.5(13) . . . . ? C2 C3 C4 C5 0.9(12) . . . . ? N2 N1 C5 C6 0.3(7) . . . . ? N2 N1 C5 C4 178.0(7) . . . . ? C3 C4 C5 N1 -178.9(7) . . . . ? C3 C4 C5 C6 -1.5(10) . . . . ? N2 N3 C6 C5 2.4(7) . . . . ? N2 N3 C6 C1 -179.1(7) . . . . ? N1 C5 C6 N3 -1.8(7) . . . . ? C4 C5 C6 N3 -179.7(6) . . . . ? N1 C5 C6 C1 179.5(6) . . . . ? C4 C5 C6 C1 1.6(10) . . . . ? C2 C1 C6 N3 -179.5(7) . . . . ? C2 C1 C6 C5 -1.1(10) . . . . ? N1 N2 C7 C15 77.7(8) . . . . ? N3 N2 C7 C15 -108.2(6) . . . . ? N1 N2 C7 C8 -102.0(6) . . . . ? N3 N2 C7 C8 72.1(7) . . . . ? C15 C7 C8 C13 -116.0(7) . . . . ? N2 C7 C8 C13 63.7(7) . . . . ? C15 C7 C8 C9 66.4(8) . . . . ? N2 C7 C8 C9 -113.9(6) . . . . ? C13 C8 C9 C10 3.6(9) . . . . ? C7 C8 C9 C10 -178.8(5) . . . . ? C8 C9 C10 C11 -1.5(9) . . . . ? C9 C10 C11 O1 177.5(5) . . . . ? C9 C10 C11 C12 0.1(9) . . . . ? C14 O1 C11 C10 13.8(8) . . . . ? C14 O1 C11 C12 -168.6(5) . . . . ? C10 C11 C12 C13 -0.7(9) . . . . ? O1 C11 C12 C13 -178.5(5) . . . . ? C9 C8 C13 C12 -4.2(9) . . . . ? C7 C8 C13 C12 178.2(5) . . . . ? C11 C12 C13 C8 2.8(10) . . . . ? C11 O1 C14 C17 175.6(5) . . . . ? N2 C7 C15 Si -175.6(4) . . . . ? C8 C7 C15 Si 4.1(9) . . . . ? N2 C7 C15 I 6.9(8) . . . . ? C8 C7 C15 I -173.4(4) . . . . ? C19 Si C15 C7 26.7(7) . . . . ? C20 Si C15 C7 -96.5(6) . . . . ? C18 Si C15 C7 143.7(6) . . . . ? C19 Si C15 I -155.7(3) . . . . ? C20 Si C15 I 81.2(4) . . . . ? C18 Si C15 I -38.7(4) . . . . ? O1 C14 C17 C16 1.9(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.38 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.518 _refine_diff_density_min -0.532 _refine_diff_density_rms 0.086 # Attachment '20120921.pdf' _database_code_depnum_ccdc_archive 'CCDC 902448'