# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_hphh _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C21 H14 I N O' _chemical_formula_sum 'C21 H14 I N O' _chemical_melting_point ? _exptl_crystal_description parallelepiped _exptl_crystal_colour yellow _diffrn_ambient_temperature 297(2) _chemical_formula_weight 423.23 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 'P 21/n' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.6456(3) _cell_length_b 20.4565(5) _cell_length_c 9.9640(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.672(4) _cell_angle_gamma 90.00 _cell_volume 1696.71(9) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 4337 _cell_measurement_theta_min 2.9056 _cell_measurement_theta_max 29.0728 _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.657 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 1.894 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.72875 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8278 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 29.13 _reflns_number_total 3962 _reflns_number_gt 2742 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _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^)+(0.0350P)^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 3962 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0699 _refine_ls_wR_factor_gt 0.0663 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 0.22524(3) 0.182324(9) 0.78009(2) 0.05487(9) Uani 1 1 d . . . O O 0.1917(2) 0.06919(8) 0.96243(19) 0.0474(5) Uani 1 1 d . . . N N 0.2153(3) -0.00187(10) 1.1492(3) 0.0465(6) Uani 1 1 d . . . C1 C 0.1512(3) 0.04673(12) 1.2179(3) 0.0403(6) Uani 1 1 d . . . C2 C 0.1248(4) 0.03108(13) 1.3457(3) 0.0518(8) Uani 1 1 d . . . H2A H 0.1538 -0.0100 1.3844 0.062 Uiso 1 1 calc R . . C3 C 0.0567(4) 0.07531(13) 1.4151(3) 0.0537(8) Uani 1 1 d . . . H3A H 0.0381 0.0641 1.4998 0.064 Uiso 1 1 calc R . . C4 C 0.0155(4) 0.13637(14) 1.3595(3) 0.0502(8) Uani 1 1 d . . . H4A H -0.0325 0.1662 1.4061 0.060 Uiso 1 1 calc R . . C5 C 0.0450(4) 0.15352(14) 1.2355(3) 0.0464(7) Uani 1 1 d . . . H5A H 0.0175 0.1952 1.1995 0.056 Uiso 1 1 calc R . . C6 C 0.1151(3) 0.10971(12) 1.1627(3) 0.0366(6) Uani 1 1 d . . . C7 C 0.1511(3) 0.12377(11) 1.0304(3) 0.0355(6) Uani 1 1 d . . . C8 C 0.2305(3) 0.01135(12) 1.0299(3) 0.0397(6) Uani 1 1 d . . . C9 C 0.1532(3) 0.18046(12) 0.9659(3) 0.0376(6) Uani 1 1 d . . . C10 C 0.1246(3) 0.24653(11) 1.0157(3) 0.0370(6) Uani 1 1 d . . . C11 C -0.0258(4) 0.27524(13) 0.9763(3) 0.0457(7) Uani 1 1 d . . . H11A H -0.1120 0.2527 0.9190 0.055 Uiso 1 1 calc R . . C12 C -0.0483(4) 0.33809(15) 1.0227(3) 0.0571(9) Uani 1 1 d . . . H12A H -0.1492 0.3575 0.9953 0.068 Uiso 1 1 calc R . . C13 C 0.0768(5) 0.37091(14) 1.1077(3) 0.0579(9) Uani 1 1 d . . . H13A H 0.0610 0.4125 1.1392 0.070 Uiso 1 1 calc R . . C14 C 0.2260(4) 0.34300(15) 1.1471(4) 0.0582(8) Uani 1 1 d . . . H14A H 0.3111 0.3657 1.2055 0.070 Uiso 1 1 calc R . . C15 C 0.2512(4) 0.28148(13) 1.1008(3) 0.0477(7) Uani 1 1 d . . . H15A H 0.3535 0.2633 1.1268 0.057 Uiso 1 1 calc R . . C16 C 0.2944(3) -0.03557(12) 0.9456(3) 0.0418(7) Uani 1 1 d . . . C17 C 0.3282(4) -0.01711(14) 0.8239(3) 0.0536(8) Uani 1 1 d . . . H17A H 0.3077 0.0255 0.7914 0.064 Uiso 1 1 calc R . . C18 C 0.3929(4) -0.06200(16) 0.7493(4) 0.0647(9) Uani 1 1 d . . . H18A H 0.4165 -0.0493 0.6674 0.078 Uiso 1 1 calc R . . C19 C 0.4216(4) -0.12464(17) 0.7964(4) 0.0673(10) Uani 1 1 d . . . H19A H 0.4633 -0.1549 0.7458 0.081 Uiso 1 1 calc R . . C20 C 0.3894(4) -0.14285(15) 0.9176(4) 0.0666(10) Uani 1 1 d . . . H20A H 0.4105 -0.1855 0.9499 0.080 Uiso 1 1 calc R . . C21 C 0.3258(4) -0.09866(13) 0.9930(3) 0.0544(8) Uani 1 1 d . . . H21A H 0.3041 -0.1115 1.0756 0.065 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 0.07895(17) 0.05162(13) 0.04076(12) 0.00547(9) 0.02769(11) 0.01234(10) O 0.0720(14) 0.0327(9) 0.0427(11) -0.0021(8) 0.0244(10) 0.0091(9) N 0.0586(16) 0.0333(12) 0.0546(15) 0.0020(11) 0.0269(13) 0.0031(11) C1 0.0441(17) 0.0352(13) 0.0455(16) -0.0026(13) 0.0186(14) -0.0046(12) C2 0.069(2) 0.0366(15) 0.0593(19) 0.0044(14) 0.0333(18) -0.0043(14) C3 0.063(2) 0.0539(18) 0.0536(18) 0.0031(15) 0.0327(17) -0.0109(15) C4 0.057(2) 0.0517(17) 0.0518(18) -0.0067(15) 0.0314(16) -0.0007(14) C5 0.0532(19) 0.0432(15) 0.0470(17) 0.0018(14) 0.0204(15) 0.0080(13) C6 0.0364(16) 0.0379(14) 0.0364(14) -0.0058(12) 0.0111(12) -0.0029(11) C7 0.0379(16) 0.0340(13) 0.0348(14) -0.0031(12) 0.0100(12) 0.0027(11) C8 0.0394(17) 0.0319(13) 0.0478(17) -0.0031(13) 0.0120(14) -0.0017(11) C9 0.0409(16) 0.0365(13) 0.0373(14) -0.0017(12) 0.0141(12) 0.0048(12) C10 0.0475(18) 0.0319(13) 0.0340(14) 0.0039(11) 0.0150(13) 0.0054(12) C11 0.0507(19) 0.0461(15) 0.0412(16) 0.0017(14) 0.0136(14) 0.0061(13) C12 0.065(2) 0.0587(18) 0.054(2) 0.0137(17) 0.0276(18) 0.0259(17) C13 0.085(3) 0.0394(16) 0.057(2) -0.0006(15) 0.031(2) 0.0056(17) C14 0.069(2) 0.0451(16) 0.063(2) -0.0110(17) 0.0225(19) -0.0083(16) C15 0.0474(19) 0.0439(16) 0.0535(18) -0.0005(15) 0.0167(15) 0.0039(13) C16 0.0377(17) 0.0358(14) 0.0509(17) -0.0092(13) 0.0105(14) -0.0007(11) C17 0.062(2) 0.0441(16) 0.060(2) -0.0085(15) 0.0253(17) 0.0019(14) C18 0.074(3) 0.068(2) 0.060(2) -0.0180(18) 0.0295(19) -0.0029(18) C19 0.063(2) 0.064(2) 0.073(3) -0.0277(19) 0.016(2) 0.0136(17) C20 0.074(3) 0.0436(17) 0.078(3) -0.0136(18) 0.014(2) 0.0159(16) C21 0.063(2) 0.0423(16) 0.0557(19) -0.0079(15) 0.0122(17) 0.0067(14) _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 C9 2.108(3) . ? O C8 1.357(3) . ? O C7 1.399(3) . ? N C8 1.260(3) . ? N C1 1.403(3) . ? C1 C6 1.403(3) . ? C1 C2 1.391(4) . ? C2 C3 1.365(4) . ? C2 H2A 0.9300 . ? C3 C4 1.374(4) . ? C3 H3A 0.9300 . ? C4 C5 1.373(4) . ? C4 H4A 0.9300 . ? C5 C6 1.391(3) . ? C5 H5A 0.9300 . ? C6 C7 1.462(3) . ? C7 C9 1.328(3) . ? C8 C16 1.477(4) . ? C9 C10 1.483(3) . ? C10 C11 1.384(4) . ? C10 C15 1.388(4) . ? C11 C12 1.397(4) . ? C11 H11A 0.9300 . ? C12 C13 1.357(5) . ? C12 H12A 0.9300 . ? C13 C14 1.368(5) . ? C13 H13A 0.9300 . ? C14 C15 1.377(4) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 C21 1.376(4) . ? C16 C17 1.374(4) . ? C17 C18 1.391(4) . ? C17 H17A 0.9300 . ? C18 C19 1.364(4) . ? C18 H18A 0.9300 . ? C19 C20 1.363(5) . ? C19 H19A 0.9300 . ? C20 C21 1.381(4) . ? C20 H20A 0.9300 . ? C21 H21A 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 C8 O C7 121.1(2) . . ? C8 N C1 117.7(2) . . ? C6 C1 C2 119.8(2) . . ? C6 C1 N 122.3(2) . . ? C2 C1 N 117.9(2) . . ? C3 C2 C1 120.7(3) . . ? C3 C2 H2A 119.6 . . ? C1 C2 H2A 119.6 . . ? C2 C3 C4 119.9(3) . . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.0 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4A 119.9 . . ? C3 C4 H4A 119.9 . . ? C4 C5 C6 121.2(3) . . ? C4 C5 H5A 119.4 . . ? C6 C5 H5A 119.4 . . ? C5 C6 C1 118.0(2) . . ? C5 C6 C7 124.9(2) . . ? C1 C6 C7 117.1(2) . . ? C9 C7 O 115.1(2) . . ? C9 C7 C6 129.9(2) . . ? O C7 C6 115.0(2) . . ? N C8 O 125.4(2) . . ? N C8 C16 123.2(2) . . ? O C8 C16 111.4(2) . . ? C7 C9 C10 127.5(2) . . ? C7 C9 I 119.11(18) . . ? C10 C9 I 113.11(17) . . ? C11 C10 C15 118.7(2) . . ? C11 C10 C9 121.4(3) . . ? C15 C10 C9 119.9(2) . . ? C10 C11 C12 120.0(3) . . ? C10 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? C13 C12 C11 120.2(3) . . ? C13 C12 H12A 119.9 . . ? C11 C12 H12A 119.9 . . ? C14 C13 C12 120.2(3) . . ? C14 C13 H13A 119.9 . . ? C12 C13 H13A 119.9 . . ? C13 C14 C15 120.5(3) . . ? C13 C14 H14A 119.8 . . ? C15 C14 H14A 119.8 . . ? C10 C15 C14 120.4(3) . . ? C10 C15 H15A 119.8 . . ? C14 C15 H15A 119.8 . . ? C21 C16 C17 119.4(3) . . ? C21 C16 C8 118.9(3) . . ? C17 C16 C8 121.6(2) . . ? C16 C17 C18 120.2(3) . . ? C16 C17 H17A 119.9 . . ? C18 C17 H17A 119.9 . . ? C19 C18 C17 119.9(3) . . ? C19 C18 H18A 120.0 . . ? C17 C18 H18A 120.0 . . ? C18 C19 C20 120.0(3) . . ? C18 C19 H19A 120.0 . . ? C20 C19 H19A 120.0 . . ? C19 C20 C21 120.7(3) . . ? C19 C20 H20A 119.7 . . ? C21 C20 H20A 119.7 . . ? C16 C21 C20 119.8(3) . . ? C16 C21 H21A 120.1 . . ? C20 C21 H21A 120.1 . . ? _diffrn_measured_fraction_theta_max 0.866 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.683 _refine_diff_density_min -0.750 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 834780' ####################################################################### # # 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_clph3m _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H13 Cl I N O' _chemical_formula_sum 'C21 H13 Cl I N O' _chemical_formula_weight 457.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and =.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and =.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and =.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and =.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and =.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and =.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_int_tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.6740(11) _cell_length_b 8.2808(6) _cell_length_c 28.5842(19) _cell_angle_alpha 90.00 _cell_angle_beta 101.6950(10) _cell_angle_gamma 90.00 _cell_volume 3633.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 6309 _cell_measurement_theta_min 2.756 _cell_measurement_theta_max 25.980 _exptl_crystal_description parallelepiped _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 1.918 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.650068 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details empirical _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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_% ? _diffrn_reflns_number 9855 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 26.03 _reflns_number_total 3551 _reflns_number_gt 3122 _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 =nd 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 =s not relevant to the choice of reflections for refinement. R-factors =ased on F^2^ are statistically about twice as large as those based on F, and =- 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^)+(0.0453P)^2^+2.6609P] where ==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constro _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3551 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.246401(12) 0.12612(3) 0.444462(7) 0.05628(9) Uani 1 1 d . . . Cl Cl 0.63356(6) 0.54673(10) 0.62688(3) 0.0640(2) Uani 1 1 d . . . O O 0.43687(12) 0.1004(2) 0.44409(6) 0.0413(4) Uani 1 1 d . . . N N 0.57349(15) 0.1175(3) 0.42280(9) 0.0468(5) Uani 1 1 d . . . C1 C 0.39601(16) 0.0342(3) 0.40065(8) 0.0362(5) Uani 1 1 d . . . C2 C 0.45507(16) -0.0347(3) 0.37200(8) 0.0376(5) Uani 1 1 d . . . C3 C 0.43057(19) -0.1509(3) 0.33649(10) 0.0457(6) Uani 1 1 d . . . H3A H 0.3734 -0.1878 0.3292 0.055 Uiso 1 1 calc R . . C4 C 0.4915(2) -0.2114(4) 0.31198(11) 0.0569(7) Uani 1 1 d . . . H4A H 0.4745 -0.2873 0.2879 0.068 Uiso 1 1 calc R . . C5 C 0.5768(2) -0.1602(4) 0.32293(13) 0.0647(9) Uani 1 1 d . . . H5A H 0.6170 -0.2010 0.3062 0.078 Uiso 1 1 calc R . . C6 C 0.6025(2) -0.0483(4) 0.35876(11) 0.0588(8) Uani 1 1 d . . . H6A H 0.6601 -0.0139 0.3661 0.071 Uiso 1 1 calc R . . C7 C 0.54262(17) 0.0131(3) 0.38393(9) 0.0424(5) Uani 1 1 d . . . C8 C 0.52180(17) 0.1508(3) 0.45034(9) 0.0379(5) Uani 1 1 d . . . C9 C 0.54748(16) 0.2471(3) 0.49420(9) 0.0366(5) Uani 1 1 d . . . C10 C 0.63363(17) 0.2964(3) 0.50818(10) 0.0459(6) Uani 1 1 d . . . H10A H 0.6737 0.2669 0.4898 0.055 Uiso 1 1 calc R . . C11 C 0.66095(19) 0.3881(3) 0.54875(11) 0.0504(7) Uani 1 1 d . . . H11A H 0.7187 0.4209 0.5578 0.060 Uiso 1 1 calc R . . C12 C 0.60012(19) 0.4299(3) 0.57544(9) 0.0441(6) Uani 1 1 d . . . C13 C 0.5142(2) 0.3831(3) 0.56283(10) 0.0470(6) Uani 1 1 d . . . H13A H 0.4745 0.4128 0.5815 0.056 Uiso 1 1 calc R . . C14 C 0.48780(17) 0.2912(3) 0.52199(9) 0.0430(6) Uani 1 1 d . . . H14A H 0.4300 0.2587 0.5131 0.052 Uiso 1 1 calc R . . C15 C 0.30874(16) 0.0362(3) 0.39119(9) 0.0390(5) Uani 1 1 d . . . C16 C 0.24940(16) -0.0078(3) 0.34556(9) 0.0415(5) Uani 1 1 d . . . C17 C 0.1821(2) -0.1175(4) 0.34407(12) 0.0594(8) Uani 1 1 d . . . H17A H 0.1734 -0.1659 0.3721 0.071 Uiso 1 1 calc R . . C18 C 0.1276(2) -0.1554(5) 0.30081(15) 0.0748(10) Uani 1 1 d . . . H18A H 0.0832 -0.2304 0.3000 0.090 Uiso 1 1 calc R . . C19 C 0.1386(2) -0.0832(5) 0.25920(13) 0.0699(10) Uani 1 1 d . . . H19A H 0.1015 -0.1088 0.2305 0.084 Uiso 1 1 calc R . . C20 C 0.2051(2) 0.0278(4) 0.26008(11) 0.0615(8) Uani 1 1 d . . . H20A H 0.2133 0.0763 0.2320 0.074 Uiso 1 1 calc R . . C21 C 0.2593(2) 0.0656(4) 0.30321(10) 0.0499(6) Uani 1 1 d . . . H21A H 0.3032 0.1416 0.3039 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 0.04436(13) 0.08270(17) 0.04595(13) -0.01302(9) 0.01901(9) -0.00560(9) =Cl 0.0834(5) 0.0630(4) 0.0432(4) -0.0151(3) 0.0073(3) -0.0199(4) O 0.0374(9) 0.0533(10) 0.0337(9) -0.0080(7) 0.0083(7) -0.0061(7) N 0.0372(12) 0.0596(14) 0.0437(13) -0.0104(10) 0.0088(9) -0.0023(9) C1 0.0408(13) 0.0388(12) 0.0296(11) -0.0002(9) 0.0083(9) -0.0051(10) C2 0.0415(13) 0.0401(12) 0.0315(12) 0.0006(10) 0.0084(9) 0.0035(10) C3 0.0489(15) 0.0473(14) 0.0406(14) -0.0069(11) 0.0084(11) -0.0010(11) C4 0.0644(19) 0.0593(17) 0.0470(16) -0.0158(13) 0.0116(13) 0.0077(14) C5 0.0549(19) 0.082(2) 0.060(2) -0.0209(17) 0.0187(15) 0.0149(16) C6 0.0410(15) 0.083(2) 0.0538(17) -0.0157(16) 0.0122(12) 0.0073(15) C7 0.0392(13) 0.0511(14) 0.0365(13) -0.0034(11) 0.0070(10) 0.0034(11) C8 0.0343(12) 0.0405(12) 0.0372(13) 0.0016(10) 0.0034(10) -0.0006(9) C9 0.0378(12) 0.0386(12) 0.0322(12) 0.0016(9) 0.0045(9) 0.0015(9) C10 0.0366(13) 0.0551(15) 0.0457(15) -0.0071(12) 0.0075(11) -0.0011(11) C11 0.0427(15) 0.0578(16) 0.0472(16) -0.0046(12) 0.0008(12) -0.0080(12) C12 0.0561(16) 0.0401(12) 0.0330(13) -0.0008(10) 0.0021(11) -0.0055(11) C13 0.0518(16) 0.0542(16) 0.0359(13) -0.0026(11) 0.0110(12) 0.0017(12) C14 0.0372(13) 0.0521(14) 0.0388(13) -0.0019(11) 0.0059(10) -0.0033(11) C15 0.0408(13) 0.0437(13) 0.0338(12) -0.0015(10) 0.0108(10) -0.0040(10) C16 0.0381(13) 0.0482(14) 0.0373(13) -0.0024(11) 0.0053(10) 0.0018(10) C17 0.0523(17) 0.073(2) 0.0513(18) 0.0016(14) 0.0055(14) -0.0131(14) C18 0.056(2) 0.088(2) 0.073(2) -0.010(2) -0.0060(17) -0.0200(17) C19 0.064(2) 0.085(2) 0.0500(19) -0.0146(17) -0.0136(15) 0.0079(17) C20 0.069(2) 0.076(2) 0.0361(14) 0.0037(14) 0.0026(13) 0.0155(17) C21 0.0542(17) 0.0557(15) 0.0398(14) 0.0009(12) 0.0096(12) 0.0022(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) = are estimated using the full covariance matrix. The cell esds are =aken into account individually in the estimation of esds in distances, =ngles and torsion angles; correlations between esds in cell parameters are =nly used when they are defined by crystal symmetry. An approximate =isotropic) treatment of cell esds is used for estimating esds involving l.s. =lanes. ; 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 2.105(2) . ? Cl C12 1.749(3) . ? O C8 1.372(3) . ? O C1 1.389(3) . ? N C8 1.269(4) . ? N C7 1.414(3) . ? C1 C15 1.340(4) . ? C1 C2 1.470(3) . ? C2 C3 1.395(4) . ? C2 C7 1.402(4) . ? C3 C4 1.388(4) . ? C3 H3A 0.9300 . ? C4 C5 1.377(5) . ? C4 H4A 0.9300 . ? C5 C6 1.379(5) . ? C5 H5A 0.9300 . ? C6 C7 1.390(4) . ? C6 H6A 0.9300 . ? C8 C9 1.471(3) . ? C9 C10 1.390(4) . ? C9 C14 1.393(4) . ? C10 C11 1.380(4) . ? C10 H10A 0.9300 . ? C11 C12 1.380(4) . ? C11 H11A 0.9300 . ? C12 C13 1.378(4) . ? C13 C14 1.385(4) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.486(3) . ? C16 C17 1.386(4) . ? C16 C21 1.391(4) . ? C17 C18 1.389(5) . ? C17 H17A 0.9300 . ? C18 C19 1.373(6) . ? C18 H18A 0.9300 . ? C19 C20 1.386(5) . ? C19 H19A 0.9300 . ? C20 C21 1.384(4) . ? C20 H20A 0.9300 . ? C21 H21A 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 C8 O C1 119.72(19) . . ? C8 N C7 117.4(2) . . ? C15 C1 O 116.3(2) . . ? C15 C1 C2 128.7(2) . . ? O C1 C2 115.0(2) . . ? C3 C2 C7 118.9(2) . . ? C3 C2 C1 124.2(2) . . ? C7 C2 C1 116.8(2) . . ? C4 C3 C2 120.0(3) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C5 C4 C3 120.7(3) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5A 120.0 . . ? C6 C5 H5A 120.0 . . ? C5 C6 C7 120.3(3) . . ? C5 C6 H6A 119.9 . . ? C7 C6 H6A 119.9 . . ? C6 C7 C2 120.1(2) . . ? C6 C7 N 118.1(2) . . ? C2 C7 N 121.7(2) . . ? N C8 O 125.3(2) . . ? N C8 C9 123.2(2) . . ? O C8 C9 111.5(2) . . ? C10 C9 C14 119.0(2) . . ? C10 C9 C8 119.1(2) . . ? C14 C9 C8 121.9(2) . . ? C11 C10 C9 121.4(3) . . ? C11 C10 H10A 119.3 . . ? C9 C10 H10A 119.3 . . ? C12 C11 C10 118.1(3) . . ? C12 C11 H11A 121.0 . . ? C10 C11 H11A 121.0 . . ? C13 C12 C11 122.2(2) . . ? C13 C12 Cl 119.1(2) . . ? C11 C12 Cl 118.7(2) . . ? C12 C13 C14 118.9(3) . . ? C12 C13 H13A 120.5 . . ? C14 C13 H13A 120.5 . . ? C13 C14 C9 120.3(3) . . ? C13 C14 H14A 119.8 . . ? C9 C14 H14A 119.8 . . ? C1 C15 C16 127.3(2) . . ? C1 C15 I 117.58(18) . . ? C16 C15 I 114.97(17) . . ? C17 C16 C21 118.5(3) . . ? C17 C16 C15 121.7(2) . . ? C21 C16 C15 119.8(2) . . ? C16 C17 C18 120.2(3) . . ? C16 C17 H17A 119.9 . . ? C18 C17 H17A 119.9 . . ? C17 C18 C19 120.7(3) . . ? C17 C18 H18A 119.7 . . ? C19 C18 H18A 119.7 . . ? C20 C19 C18 120.0(3) . . ? C20 C19 H19A 120.0 . . ? C18 C19 H19A 120.0 . . ? C21 C20 C19 119.3(3) . . ? C21 C20 H20A 120.3 . . ? C19 C20 H20A 120.3 . . ? C20 C21 C16 121.3(3) . . ? C20 C21 H21A 119.3 . . ? C16 C21 H21A 119.3 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.279 _refine_diff_density_min -0.759 _refine_diff_density_rms 0.098 _database_code_depnum_ccdc_archive 'CCDC 834782' ####################################################################### # # 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_cf3clphm _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C22 H12 Cl F3 I N O' _chemical_formula_sum 'C22 H12 Cl F3 I N O' _chemical_melting_point ? _exptl_crystal_description parallelepiped _exptl_crystal_colour yellow _diffrn_ambient_temperature 297(2) _chemical_formula_weight 525.68 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' Cl Cl 0.1484 0.1585 '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 'C 2/c' _symmetry_int_tables_number 15 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 31.568(5) _cell_length_b 5.7418(8) _cell_length_c 23.028(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.641(3) _cell_angle_gamma 90.00 _cell_volume 4019.5(10) _cell_formula_units_Z 8 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2938 _cell_measurement_theta_min 2.681 _cell_measurement_theta_max 22.743 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.737 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2048 _exptl_absorpt_coefficient_mu 1.766 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.751864 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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_reflns_number 10822 _diffrn_reflns_av_R_equivalents 0.0511 _diffrn_reflns_av_sigmaI/netI 0.0588 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.02 _reflns_number_total 3948 _reflns_number_gt 2524 _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^)+(0.0350P)^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 3948 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0832 _refine_ls_wR_factor_gt 0.0730 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _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 0.207523(9) 0.12922(6) 0.230282(14) 0.05340(13) Uani 1 1 d . . . Cl Cl 0.38124(4) -0.2459(3) 0.05458(6) 0.0722(4) Uani 1 1 d . . . F1 F 0.0010(4) -0.637(4) 0.1465(6) 0.129(8) Uani 0.669(15) 1 d P A 1 F2 F -0.0139(2) -0.395(2) 0.0792(6) 0.112(3) Uani 0.669(15) 1 d P A 1 F3 F -0.0180(3) -0.742(3) 0.0524(8) 0.141(5) Uani 0.669(15) 1 d P A 1 F1' F -0.0034(10) -0.483(8) 0.131(2) 0.19(3) Uani 0.331(15) 1 d P A 2 F2' F -0.0225(6) -0.596(6) 0.0465(11) 0.112(3) Uani 0.331(15) 1 d P A 2 F3' F -0.0022(5) -0.838(5) 0.1136(17) 0.125(8) Uani 0.331(15) 1 d P A 2 N N 0.18181(11) -0.5749(6) 0.07678(16) 0.0469(9) Uani 1 1 d . . . O O 0.19207(9) -0.2164(5) 0.12660(13) 0.0490(8) Uani 1 1 d . . . C1 C 0.20430(13) -0.3957(8) 0.09582(18) 0.0413(10) Uani 1 1 d . . . C2 C 0.15651(13) -0.2462(8) 0.15141(19) 0.0423(10) Uani 1 1 d . . . C3 C 0.12427(13) -0.4211(7) 0.11940(18) 0.0398(10) Uani 1 1 d . . . C4 C 0.13935(14) -0.5847(7) 0.08493(19) 0.0434(11) Uani 1 1 d . . . C5 C 0.11128(15) -0.7630(9) 0.0562(2) 0.0581(13) Uani 1 1 d . . . H5A H 0.1214 -0.8759 0.0343 0.070 Uiso 1 1 calc R . . C6 C 0.06859(15) -0.7717(10) 0.0604(2) 0.0604(13) Uani 1 1 d . . . H6A H 0.0502 -0.8926 0.0421 0.072 Uiso 1 1 calc R . . C7 C 0.05307(14) -0.6008(9) 0.0918(2) 0.0561(13) Uani 1 1 d . A . C8 C 0.08056(14) -0.4287(8) 0.1210(2) 0.0509(12) Uani 1 1 d . . . H8A H 0.0699 -0.3153 0.1423 0.061 Uiso 1 1 calc R . . C9 C 0.24821(13) -0.3544(8) 0.08614(17) 0.0404(10) Uani 1 1 d . . . C10 C 0.27123(15) -0.1495(9) 0.1040(2) 0.0563(12) Uani 1 1 d . . . H10A H 0.2592 -0.0336 0.1229 0.068 Uiso 1 1 calc R . . C11 C 0.31210(15) -0.1168(9) 0.0940(2) 0.0576(12) Uani 1 1 d . . . H11A H 0.3274 0.0215 0.1054 0.069 Uiso 1 1 calc R . . C12 C 0.32982(14) -0.2895(9) 0.0671(2) 0.0500(12) Uani 1 1 d . . . C13 C 0.30769(16) -0.4910(9) 0.0489(2) 0.0638(14) Uani 1 1 d . . . H13A H 0.3199 -0.6062 0.0300 0.077 Uiso 1 1 calc R . . C14 C 0.26689(15) -0.5223(9) 0.0589(2) 0.0561(13) Uani 1 1 d . . . H14A H 0.2518 -0.6607 0.0468 0.067 Uiso 1 1 calc R . . C15 C 0.15627(13) -0.1141(7) 0.19866(19) 0.0437(10) Uani 1 1 d . . . C16 C 0.12361(13) -0.1215(8) 0.23399(18) 0.0437(10) Uani 1 1 d . . . C17 C 0.09500(16) 0.0588(8) 0.2332(2) 0.0623(14) Uani 1 1 d . . . H17A H 0.0962 0.1905 0.2101 0.075 Uiso 1 1 calc R . . C18 C 0.06440(18) 0.0473(10) 0.2662(3) 0.0786(18) Uani 1 1 d . . . H18A H 0.0451 0.1709 0.2647 0.094 Uiso 1 1 calc R . . C19 C 0.06204(17) -0.1394(12) 0.3004(2) 0.0762(16) Uani 1 1 d . . . H19A H 0.0416 -0.1443 0.3229 0.091 Uiso 1 1 calc R . . C20 C 0.09030(19) -0.3235(10) 0.3017(3) 0.0775(17) Uani 1 1 d . . . H20A H 0.0885 -0.4553 0.3244 0.093 Uiso 1 1 calc R . . C21 C 0.12129(16) -0.3123(9) 0.2693(2) 0.0623(14) Uani 1 1 d . . . H21A H 0.1408 -0.4352 0.2714 0.075 Uiso 1 1 calc R . . C22 C 0.00674(18) -0.6073(16) 0.0950(3) 0.0820(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I 0.04433(18) 0.05222(19) 0.0618(2) -0.01151(17) 0.01112(13) -0.00177(16) Cl 0.0444(7) 0.0978(10) 0.0821(10) -0.0153(8) 0.0305(6) -0.0168(7) F1 0.071(5) 0.22(2) 0.116(9) 0.064(13) 0.054(5) 0.011(9) F2 0.060(3) 0.150(8) 0.134(7) 0.022(6) 0.040(4) 0.032(5) F3 0.046(4) 0.149(10) 0.229(10) -0.104(9) 0.039(5) -0.034(5) F1' 0.11(2) 0.22(4) 0.28(6) -0.19(4) 0.14(3) -0.10(2) F2' 0.060(3) 0.150(8) 0.134(7) 0.022(6) 0.040(4) 0.032(5) F3' 0.072(9) 0.127(17) 0.20(2) 0.061(17) 0.072(12) -0.024(9) N 0.042(2) 0.050(3) 0.052(2) -0.0105(18) 0.0197(17) -0.0069(17) O 0.0452(18) 0.0484(19) 0.062(2) -0.0128(15) 0.0286(15) -0.0093(14) C1 0.043(2) 0.047(3) 0.036(3) -0.002(2) 0.0140(19) 0.003(2) C2 0.036(2) 0.046(3) 0.046(3) 0.002(2) 0.012(2) 0.000(2) C3 0.037(2) 0.045(3) 0.039(3) 0.0033(19) 0.0134(19) -0.0048(19) C4 0.042(2) 0.047(3) 0.043(3) -0.003(2) 0.016(2) -0.005(2) C5 0.054(3) 0.065(3) 0.059(3) -0.016(3) 0.022(2) -0.013(3) C6 0.052(3) 0.069(3) 0.062(4) -0.013(3) 0.019(2) -0.019(3) C7 0.039(3) 0.070(4) 0.060(3) -0.003(3) 0.014(2) -0.010(3) C8 0.049(3) 0.059(3) 0.047(3) -0.001(2) 0.017(2) -0.001(2) C9 0.040(2) 0.049(3) 0.034(2) -0.001(2) 0.0143(18) -0.002(2) C10 0.054(3) 0.057(3) 0.066(3) -0.015(3) 0.031(2) -0.006(3) C11 0.053(3) 0.054(3) 0.069(3) -0.012(3) 0.023(2) -0.016(3) C12 0.034(2) 0.067(3) 0.049(3) 0.000(2) 0.012(2) -0.002(2) C13 0.060(3) 0.059(3) 0.083(4) -0.021(3) 0.037(3) -0.005(3) C14 0.050(3) 0.055(3) 0.070(4) -0.019(3) 0.028(2) -0.016(2) C15 0.041(2) 0.040(2) 0.048(3) -0.003(2) 0.0089(19) 0.002(2) C16 0.048(3) 0.041(2) 0.044(3) 0.000(2) 0.015(2) 0.002(2) C17 0.062(3) 0.050(3) 0.085(4) 0.011(2) 0.038(3) 0.010(2) C18 0.079(4) 0.058(4) 0.120(5) 0.007(3) 0.064(4) 0.020(3) C19 0.067(4) 0.096(5) 0.080(4) -0.003(4) 0.046(3) -0.003(4) C20 0.082(4) 0.083(5) 0.080(4) 0.023(3) 0.042(3) 0.009(3) C21 0.063(3) 0.061(4) 0.065(4) 0.010(3) 0.022(3) 0.014(2) C22 0.045(3) 0.117(6) 0.083(5) -0.016(5) 0.015(3) -0.014(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 2.113(4) . ? Cl C12 1.742(4) . ? F1 C22 1.259(12) . ? F2 C22 1.386(12) . ? F3 C22 1.327(11) . ? F1' C22 1.19(2) . ? F2' C22 1.24(2) . ? F3' C22 1.443(19) . ? N C1 1.260(5) . ? N C4 1.404(5) . ? O C1 1.363(5) . ? O C2 1.400(5) . ? C1 C9 1.481(5) . ? C2 C15 1.328(6) . ? C2 C3 1.478(6) . ? C3 C4 1.394(5) . ? C3 C8 1.391(6) . ? C4 C5 1.398(6) . ? C5 C6 1.378(6) . ? C5 H5A 0.9300 . ? C6 C7 1.384(7) . ? C6 H6A 0.9300 . ? C7 C8 1.367(6) . ? C7 C22 1.484(7) . ? C8 H8A 0.9300 . ? C9 C14 1.368(6) . ? C9 C10 1.386(6) . ? C10 C11 1.384(6) . ? C10 H10A 0.9300 . ? C11 C12 1.366(6) . ? C11 H11A 0.9300 . ? C12 C13 1.358(6) . ? C13 C14 1.380(6) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.476(6) . ? C16 C17 1.371(6) . ? C16 C21 1.378(6) . ? C17 C18 1.383(7) . ? C17 H17A 0.9300 . ? C18 C19 1.345(7) . ? C18 H18A 0.9300 . ? C19 C20 1.378(7) . ? C19 H19A 0.9300 . ? C20 C21 1.383(7) . ? C20 H20A 0.9300 . ? C21 H21A 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 C1 N C4 117.0(4) . . ? C1 O C2 119.3(3) . . ? N C1 O 125.9(4) . . ? N C1 C9 122.7(4) . . ? O C1 C9 111.4(4) . . ? C15 C2 O 116.5(4) . . ? C15 C2 C3 129.9(4) . . ? O C2 C3 113.6(4) . . ? C4 C3 C8 119.2(4) . . ? C4 C3 C2 116.5(4) . . ? C8 C3 C2 124.2(4) . . ? C3 C4 C5 119.5(4) . . ? C3 C4 N 122.3(4) . . ? C5 C4 N 118.2(4) . . ? C6 C5 C4 120.1(5) . . ? C6 C5 H5A 120.0 . . ? C4 C5 H5A 120.0 . . ? C7 C6 C5 120.1(5) . . ? C7 C6 H6A 120.0 . . ? C5 C6 H6A 120.0 . . ? C8 C7 C6 120.2(4) . . ? C8 C7 C22 119.8(5) . . ? C6 C7 C22 120.0(5) . . ? C7 C8 C3 120.8(4) . . ? C7 C8 H8A 119.6 . . ? C3 C8 H8A 119.6 . . ? C14 C9 C10 118.6(4) . . ? C14 C9 C1 119.5(4) . . ? C10 C9 C1 121.9(4) . . ? C11 C10 C9 120.2(4) . . ? C11 C10 H10A 119.9 . . ? C9 C10 H10A 119.9 . . ? C10 C11 C12 119.5(4) . . ? C10 C11 H11A 120.3 . . ? C12 C11 H11A 120.3 . . ? C13 C12 C11 121.2(4) . . ? C13 C12 Cl 119.8(4) . . ? C11 C12 Cl 119.0(4) . . ? C12 C13 C14 119.0(5) . . ? C12 C13 H13A 120.5 . . ? C14 C13 H13A 120.5 . . ? C9 C14 C13 121.5(4) . . ? C9 C14 H14A 119.3 . . ? C13 C14 H14A 119.3 . . ? C2 C15 C16 126.5(4) . . ? C2 C15 I 119.1(3) . . ? C16 C15 I 114.4(3) . . ? C17 C16 C21 118.0(4) . . ? C17 C16 C15 121.7(4) . . ? C21 C16 C15 120.3(4) . . ? C16 C17 C18 120.8(5) . . ? C16 C17 H17A 119.6 . . ? C18 C17 H17A 119.6 . . ? C19 C18 C17 121.2(5) . . ? C19 C18 H18A 119.4 . . ? C17 C18 H18A 119.4 . . ? C18 C19 C20 119.1(5) . . ? C18 C19 H19A 120.4 . . ? C20 C19 H19A 120.4 . . ? C19 C20 C21 120.0(5) . . ? C19 C20 H20A 120.0 . . ? C21 C20 H20A 120.0 . . ? C16 C21 C20 120.9(5) . . ? C16 C21 H21A 119.5 . . ? C20 C21 H21A 119.5 . . ? F2' C22 F1 126.4(11) . . ? F2' C22 F1' 108(2) . . ? F1 C22 F1' 45(2) . . ? F2' C22 F3 38.7(9) . . ? F1 C22 F3 114.4(10) . . ? F1' C22 F3 130.0(13) . . ? F2' C22 F2 62.3(14) . . ? F1 C22 F2 100.8(10) . . ? F1' C22 F2 57(3) . . ? F3 C22 F2 100.3(10) . . ? F2' C22 F3' 99.1(12) . . ? F1 C22 F3' 60.5(10) . . ? F1' C22 F3' 103(2) . . ? F3 C22 F3' 64.0(11) . . ? F2 C22 F3' 140.4(8) . . ? F2' C22 C7 117.1(10) . . ? F1 C22 C7 116.3(8) . . ? F1' C22 C7 118.0(11) . . ? F3 C22 C7 111.7(6) . . ? F2 C22 C7 111.4(7) . . ? F3' C22 C7 108.2(9) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.570 _refine_diff_density_min -0.551 _refine_diff_density_rms 0.080 _database_code_depnum_ccdc_archive 'CCDC 834785' ####################################################################### # # 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_no2c43 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C19 H17 I N2 O3' _chemical_formula_sum 'C19 H17 I N2 O3' _chemical_melting_point ? _exptl_crystal_description parallelepiped _exptl_crystal_colour red _diffrn_ambient_temperature 110(2) _chemical_formula_weight 448.25 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 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 6.8137(3) _cell_length_b 10.3948(5) _cell_length_c 24.8522(12) _cell_angle_alpha 90.00 _cell_angle_beta 96.933(4) _cell_angle_gamma 90.00 _cell_volume 1747.34(14) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5933 _cell_measurement_theta_min 3.0044 _cell_measurement_theta_max 29.1277 _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.704 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 1.853 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.88798 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7521 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 29.21 _reflns_number_total 4021 _reflns_number_gt 3774 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0366P)^2^+48.1422P] 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 4021 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0700 _refine_ls_wR_factor_ref 0.1996 _refine_ls_wR_factor_gt 0.1984 _refine_ls_goodness_of_fit_ref 1.288 _refine_ls_restrained_S_all 1.288 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I I 0.31633(10) 0.12254(5) 0.08872(2) 0.01939(19) Uani 1 1 d . . . O1 O 0.2861(9) 0.3114(6) -0.0024(2) 0.0135(12) Uani 1 1 d . . . O2 O 0.0703(12) -0.1493(6) -0.1940(3) 0.0293(17) Uani 1 1 d . . . O3 O 0.0092(11) -0.0070(7) -0.2563(3) 0.0257(15) Uani 1 1 d . . . N1 N 0.1723(11) 0.4754(7) -0.0630(3) 0.0133(14) Uani 1 1 d . . . N2 N 0.0578(12) -0.0368(8) -0.2099(3) 0.0195(16) Uani 1 1 d . . . C1 C 0.2921(12) 0.3896(8) 0.0438(3) 0.0124(15) Uani 1 1 d . . . C2 C 0.2820(12) 0.5256(8) 0.0326(3) 0.0119(15) Uani 1 1 d . . . C3 C 0.3331(14) 0.6207(9) 0.0708(3) 0.0179(17) Uani 1 1 d . . . H3A H 0.3882 0.5958 0.1062 0.021 Uiso 1 1 calc R . . C4 C 0.3070(13) 0.7507(8) 0.0595(4) 0.0169(17) Uani 1 1 d . . . H4A H 0.3374 0.8134 0.0870 0.020 Uiso 1 1 calc R . . C5 C 0.2338(13) 0.7884(8) 0.0057(4) 0.0171(17) Uani 1 1 d . . . H5A H 0.2132 0.8768 -0.0031 0.020 Uiso 1 1 calc R . . C6 C 0.1931(13) 0.6947(9) -0.0338(4) 0.0196(18) Uani 1 1 d . . . H6A H 0.1481 0.7185 -0.0701 0.024 Uiso 1 1 calc R . . C7 C 0.2184(12) 0.5652(8) -0.0199(4) 0.0133(16) Uani 1 1 d . . . C8 C 0.2097(13) 0.3584(8) -0.0516(3) 0.0147(16) Uani 1 1 d . . . C9 C 0.1746(13) 0.2558(8) -0.0929(3) 0.0118(15) Uani 1 1 d . . . C10 C 0.2125(13) 0.1261(9) -0.0782(3) 0.0169(17) Uani 1 1 d . . . H10A H 0.2649 0.1047 -0.0422 0.020 Uiso 1 1 calc R . . C11 C 0.1731(13) 0.0310(8) -0.1165(4) 0.0168(17) Uani 1 1 d . . . H11A H 0.1956 -0.0569 -0.1072 0.020 Uiso 1 1 calc R . . C12 C 0.1002(13) 0.0661(9) -0.1686(4) 0.0166(17) Uani 1 1 d . . . C13 C 0.0625(14) 0.1916(9) -0.1848(4) 0.0182(18) Uani 1 1 d . . . H13A H 0.0124 0.2116 -0.2211 0.022 Uiso 1 1 calc R . . C14 C 0.1003(14) 0.2877(9) -0.1461(3) 0.0177(17) Uani 1 1 d . . . H14A H 0.0756 0.3751 -0.1558 0.021 Uiso 1 1 calc R . . C15 C 0.3022(13) 0.3238(8) 0.0910(4) 0.0142(16) Uani 1 1 d . . . C16 C 0.3081(14) 0.3763(9) 0.1475(4) 0.0190(17) Uani 1 1 d . . . H16A H 0.2304 0.3192 0.1687 0.023 Uiso 1 1 calc R . . H16B H 0.2448 0.4622 0.1458 0.023 Uiso 1 1 calc R . . C17 C 0.5196(14) 0.3883(9) 0.1769(4) 0.0205(18) Uani 1 1 d . . . H17A H 0.5846 0.3030 0.1773 0.025 Uiso 1 1 calc R . . H17B H 0.5959 0.4479 0.1562 0.025 Uiso 1 1 calc R . . C18 C 0.5260(15) 0.4369(10) 0.2346(4) 0.024(2) Uani 1 1 d . . . H18A H 0.6560 0.4153 0.2549 0.029 Uiso 1 1 calc R . . H18B H 0.4228 0.3924 0.2525 0.029 Uiso 1 1 calc R . . C19 C 0.4932(17) 0.5837(11) 0.2372(5) 0.031(2) Uani 1 1 d . . . H19A H 0.4979 0.6105 0.2752 0.047 Uiso 1 1 calc R . . H19B H 0.3638 0.6054 0.2177 0.047 Uiso 1 1 calc R . . H19C H 0.5970 0.6282 0.2205 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I 0.0304(3) 0.0106(3) 0.0168(3) 0.0021(2) 0.0014(2) 0.0002(2) O1 0.022(3) 0.008(3) 0.011(3) 0.001(2) 0.001(2) 0.003(2) O2 0.050(5) 0.009(3) 0.029(4) -0.007(3) 0.002(3) 0.000(3) O3 0.033(4) 0.023(4) 0.020(3) -0.009(3) 0.000(3) 0.002(3) N1 0.016(3) 0.013(3) 0.011(3) 0.003(3) 0.001(3) -0.001(3) N2 0.020(4) 0.018(4) 0.021(4) -0.006(3) 0.003(3) -0.005(3) C1 0.017(4) 0.006(4) 0.014(4) -0.002(3) 0.000(3) 0.001(3) C2 0.011(4) 0.006(3) 0.019(4) 0.002(3) 0.002(3) 0.000(3) C3 0.027(5) 0.012(4) 0.014(4) -0.008(3) 0.000(3) -0.001(4) C4 0.019(4) 0.013(4) 0.018(4) -0.006(3) 0.001(3) -0.002(3) C5 0.019(4) 0.007(4) 0.025(4) 0.004(3) -0.001(3) 0.008(3) C6 0.014(4) 0.020(5) 0.023(5) 0.010(4) 0.001(3) 0.002(3) C7 0.014(4) 0.005(3) 0.021(4) 0.001(3) 0.004(3) 0.000(3) C8 0.017(4) 0.014(4) 0.014(4) 0.000(3) 0.003(3) -0.004(3) C9 0.017(4) 0.006(3) 0.013(4) -0.002(3) 0.005(3) 0.001(3) C10 0.023(4) 0.013(4) 0.013(4) 0.002(3) -0.003(3) -0.002(3) C11 0.020(4) 0.010(4) 0.021(4) 0.006(3) 0.006(3) -0.001(3) C12 0.019(4) 0.017(4) 0.014(4) -0.005(3) 0.000(3) -0.003(3) C13 0.020(4) 0.020(4) 0.013(4) 0.003(3) -0.001(3) 0.004(4) C14 0.026(5) 0.015(4) 0.013(4) 0.003(3) 0.004(3) 0.002(3) C15 0.015(4) 0.010(4) 0.018(4) -0.002(3) 0.004(3) -0.001(3) C16 0.023(4) 0.017(4) 0.017(4) 0.005(4) 0.004(3) 0.000(4) C17 0.022(4) 0.019(4) 0.020(4) -0.002(4) 0.001(3) 0.001(4) C18 0.025(5) 0.028(5) 0.018(4) -0.003(4) 0.001(4) -0.006(4) C19 0.034(6) 0.024(5) 0.036(6) -0.010(4) 0.007(5) -0.005(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I C15 2.095(8) . ? O1 C8 1.359(10) . ? O1 C1 1.403(10) . ? O2 N2 1.235(11) . ? O3 N2 1.201(11) . ? N1 C8 1.268(11) . ? N1 C7 1.427(11) . ? N2 C12 1.485(11) . ? C1 C15 1.353(12) . ? C1 C2 1.441(11) . ? C2 C3 1.385(12) . ? C2 C7 1.386(12) . ? C3 C4 1.388(13) . ? C3 H3A 0.9500 . ? C4 C5 1.425(12) . ? C4 H4A 0.9500 . ? C5 C6 1.387(14) . ? C5 H5A 0.9500 . ? C6 C7 1.395(12) . ? C6 H6A 0.9500 . ? C8 C9 1.479(11) . ? C9 C14 1.399(12) . ? C9 C10 1.412(12) . ? C10 C11 1.376(13) . ? C10 H10A 0.9500 . ? C11 C12 1.380(12) . ? C11 H11A 0.9500 . ? C12 C13 1.380(13) . ? C13 C14 1.388(13) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 C16 1.502(12) . ? C16 C17 1.540(13) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.518(13) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.545(15) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? 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 C8 O1 C1 119.8(6) . . ? C8 N1 C7 116.1(7) . . ? O3 N2 O2 123.5(8) . . ? O3 N2 C12 119.0(8) . . ? O2 N2 C12 117.5(8) . . ? C15 C1 O1 114.2(7) . . ? C15 C1 C2 131.3(8) . . ? O1 C1 C2 114.5(7) . . ? C3 C2 C7 117.2(8) . . ? C3 C2 C1 124.5(8) . . ? C7 C2 C1 118.4(8) . . ? C2 C3 C4 122.7(8) . . ? C2 C3 H3A 118.6 . . ? C4 C3 H3A 118.6 . . ? C3 C4 C5 118.7(8) . . ? C3 C4 H4A 120.7 . . ? C5 C4 H4A 120.7 . . ? C6 C5 C4 119.2(8) . . ? C6 C5 H5A 120.4 . . ? C4 C5 H5A 120.4 . . ? C5 C6 C7 119.6(8) . . ? C5 C6 H6A 120.2 . . ? C7 C6 H6A 120.2 . . ? C2 C7 C6 122.4(8) . . ? C2 C7 N1 121.8(7) . . ? C6 C7 N1 115.8(8) . . ? N1 C8 O1 126.2(8) . . ? N1 C8 C9 121.7(8) . . ? O1 C8 C9 112.1(7) . . ? C14 C9 C10 120.3(8) . . ? C14 C9 C8 119.7(7) . . ? C10 C9 C8 120.0(8) . . ? C11 C10 C9 119.6(8) . . ? C11 C10 H10A 120.2 . . ? C9 C10 H10A 120.2 . . ? C10 C11 C12 118.5(8) . . ? C10 C11 H11A 120.8 . . ? C12 C11 H11A 120.8 . . ? C13 C12 C11 123.8(8) . . ? C13 C12 N2 117.8(8) . . ? C11 C12 N2 118.4(8) . . ? C12 C13 C14 117.8(8) . . ? C12 C13 H13A 121.1 . . ? C14 C13 H13A 121.1 . . ? C13 C14 C9 120.0(8) . . ? C13 C14 H14A 120.0 . . ? C9 C14 H14A 120.0 . . ? C1 C15 C16 128.3(8) . . ? C1 C15 I 118.6(6) . . ? C16 C15 I 113.1(6) . . ? C15 C16 C17 113.0(7) . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C18 C17 C16 113.2(8) . . ? C18 C17 H17A 108.9 . . ? C16 C17 H17A 108.9 . . ? C18 C17 H17B 108.9 . . ? C16 C17 H17B 108.9 . . ? H17A C17 H17B 107.8 . . ? C17 C18 C19 112.4(9) . . ? C17 C18 H18A 109.1 . . ? C19 C18 H18A 109.1 . . ? C17 C18 H18B 109.1 . . ? C19 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.848 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.408 _refine_diff_density_min -2.202 _refine_diff_density_rms 0.229 _database_code_depnum_ccdc_archive 'CCDC 834787' ####################################################################### # # 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_hcf3c43 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C20 H17 F3 I N O' _chemical_formula_sum 'C20 H17 F3 I N O' _chemical_melting_point ? _exptl_crystal_description parallelepiped _exptl_crystal_colour yellow _diffrn_ambient_temperature 100(2) _chemical_formula_weight 471.25 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' 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' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.3560(2) _cell_length_b 11.4646(7) _cell_length_c 15.8424(10) _cell_angle_alpha 107.043(6) _cell_angle_beta 96.345(4) _cell_angle_gamma 98.308(4) _cell_volume 908.22(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6368 _cell_measurement_theta_min 3.5883 _cell_measurement_theta_max 29.1144 _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.723 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 1.801 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.88597 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7973 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 29.17 _reflns_number_total 4162 _reflns_number_gt 3744 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _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^)+(0.0280P)^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 4162 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0237 _refine_ls_R_factor_gt 0.0201 _refine_ls_wR_factor_ref 0.0486 _refine_ls_wR_factor_gt 0.0480 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 I I 1.08013(2) 0.408992(11) 0.387242(9) 0.01998(5) Uani 1 1 d . . . F1 F 1.3480(3) 0.52256(11) 0.88504(8) 0.0327(3) Uani 1 1 d . . . F2 F 1.2767(3) 0.33979(11) 0.89621(9) 0.0365(3) Uani 1 1 d . . . F3 F 1.6596(2) 0.44235(13) 0.92500(9) 0.0385(3) Uani 1 1 d . . . O O 1.3496(2) 0.22443(11) 0.44417(9) 0.0153(3) Uani 1 1 d . . . N N 1.7081(3) 0.13959(13) 0.47793(11) 0.0152(3) Uani 1 1 d . . . C1 C 1.3860(3) 0.20797(16) 0.35583(12) 0.0133(3) Uani 1 1 d . . . C2 C 1.5359(3) 0.11144(15) 0.32153(12) 0.0134(3) Uani 1 1 d . . . C3 C 1.5211(3) 0.04520(16) 0.23127(13) 0.0160(4) Uani 1 1 d . . . H3A H 1.4007 0.0578 0.1876 0.019 Uiso 1 1 calc R . . C4 C 1.6812(3) -0.03894(16) 0.20506(13) 0.0177(4) Uani 1 1 d . . . H4A H 1.6719 -0.0828 0.1435 0.021 Uiso 1 1 calc R . . C5 C 1.8553(3) -0.05928(16) 0.26871(13) 0.0174(4) Uani 1 1 d . . . H5A H 1.9692 -0.1146 0.2502 0.021 Uiso 1 1 calc R . . C6 C 1.8636(3) 0.00048(16) 0.35870(13) 0.0159(4) Uani 1 1 d . . . H6A H 1.9791 -0.0157 0.4020 0.019 Uiso 1 1 calc R . . C7 C 1.7016(3) 0.08492(16) 0.38595(13) 0.0137(3) Uani 1 1 d . . . C8 C 1.5324(3) 0.20093(15) 0.50121(12) 0.0130(3) Uani 1 1 d . . . C9 C 1.5035(3) 0.25566(15) 0.59523(12) 0.0134(3) Uani 1 1 d . . . C10 C 1.6711(3) 0.23857(17) 0.66275(13) 0.0168(4) Uani 1 1 d . . . H10A H 1.7981 0.1897 0.6474 0.020 Uiso 1 1 calc R . . C11 C 1.6537(3) 0.29207(17) 0.75147(13) 0.0189(4) Uani 1 1 d . . . H11A H 1.7692 0.2807 0.7971 0.023 Uiso 1 1 calc R . . C12 C 1.4666(3) 0.36264(16) 0.77383(12) 0.0149(4) Uani 1 1 d . . . C13 C 1.2975(3) 0.37898(17) 0.70691(13) 0.0174(4) Uani 1 1 d . . . H13A H 1.1691 0.4269 0.7224 0.021 Uiso 1 1 calc R . . C14 C 1.3154(3) 0.32585(16) 0.61810(13) 0.0163(4) Uani 1 1 d . . . H14A H 1.1994 0.3372 0.5726 0.020 Uiso 1 1 calc R . . C15 C 1.4392(4) 0.41718(17) 0.86945(14) 0.0208(4) Uani 1 1 d . . . C16 C 1.2882(3) 0.28200(16) 0.31522(12) 0.0142(4) Uani 1 1 d . . . C17 C 1.3077(3) 0.28816(16) 0.22283(13) 0.0159(4) Uani 1 1 d . . . H17A H 1.4540 0.2503 0.2024 0.019 Uiso 1 1 calc R . . H17B H 1.3444 0.3765 0.2256 0.019 Uiso 1 1 calc R . . C18 C 1.0678(3) 0.22291(17) 0.15377(13) 0.0189(4) Uani 1 1 d . . . H18A H 0.9227 0.2633 0.1724 0.023 Uiso 1 1 calc R . . H18B H 1.0260 0.1354 0.1526 0.023 Uiso 1 1 calc R . . C19 C 1.0983(4) 0.2258(2) 0.05962(14) 0.0269(5) Uani 1 1 d . . . H19A H 1.1449 0.3132 0.0610 0.032 Uiso 1 1 calc R . . H19B H 1.2400 0.1831 0.0402 0.032 Uiso 1 1 calc R . . C20 C 0.8572(4) 0.1641(2) -0.00789(15) 0.0336(5) Uani 1 1 d . . . H20A H 0.8867 0.1680 -0.0670 0.050 Uiso 1 1 calc R . . H20B H 0.7172 0.2072 0.0101 0.050 Uiso 1 1 calc R . . H20C H 0.8119 0.0770 -0.0104 0.050 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 0.02469(8) 0.01904(7) 0.01966(8) 0.00679(5) 0.00562(5) 0.01198(5) F1 0.0572(8) 0.0257(6) 0.0183(7) 0.0034(5) 0.0128(6) 0.0197(6) F2 0.0575(8) 0.0274(6) 0.0216(7) 0.0043(6) 0.0200(6) -0.0047(6) F3 0.0354(7) 0.0568(9) 0.0125(7) -0.0037(6) -0.0040(6) 0.0111(6) O 0.0172(6) 0.0200(6) 0.0107(7) 0.0058(5) 0.0022(5) 0.0074(5) N 0.0165(8) 0.0162(7) 0.0119(8) 0.0029(6) 0.0013(6) 0.0042(6) C1 0.0128(8) 0.0150(8) 0.0106(9) 0.0025(7) 0.0025(7) 0.0009(6) C2 0.0131(8) 0.0129(8) 0.0142(9) 0.0047(7) 0.0018(7) 0.0022(6) C3 0.0165(9) 0.0178(9) 0.0144(9) 0.0064(7) 0.0014(7) 0.0031(7) C4 0.0220(10) 0.0160(9) 0.0142(10) 0.0024(7) 0.0058(8) 0.0034(7) C5 0.0189(9) 0.0147(8) 0.0188(10) 0.0037(8) 0.0061(8) 0.0050(7) C6 0.0154(9) 0.0150(8) 0.0175(10) 0.0053(8) 0.0007(7) 0.0043(7) C7 0.0146(8) 0.0134(8) 0.0125(9) 0.0036(7) 0.0023(7) 0.0017(6) C8 0.0138(8) 0.0131(8) 0.0121(9) 0.0049(7) 0.0005(7) 0.0016(6) C9 0.0142(8) 0.0125(8) 0.0126(9) 0.0036(7) 0.0011(7) 0.0014(6) C10 0.0188(9) 0.0190(9) 0.0138(10) 0.0055(8) 0.0028(8) 0.0071(7) C11 0.0193(9) 0.0231(9) 0.0140(10) 0.0061(8) -0.0013(8) 0.0057(7) C12 0.0183(9) 0.0142(8) 0.0112(9) 0.0032(7) 0.0035(7) 0.0012(7) C13 0.0196(9) 0.0170(9) 0.0168(10) 0.0045(8) 0.0049(8) 0.0071(7) C14 0.0173(9) 0.0195(9) 0.0133(9) 0.0060(8) 0.0013(7) 0.0064(7) C15 0.0277(11) 0.0192(9) 0.0148(10) 0.0050(8) 0.0036(8) 0.0028(8) C16 0.0144(8) 0.0142(8) 0.0136(9) 0.0030(7) 0.0027(7) 0.0037(6) C17 0.0171(9) 0.0169(9) 0.0162(10) 0.0086(8) 0.0034(7) 0.0032(7) C18 0.0186(9) 0.0230(9) 0.0164(10) 0.0086(8) 0.0029(8) 0.0031(7) C19 0.0280(11) 0.0346(12) 0.0171(11) 0.0109(9) 0.0005(9) -0.0008(9) C20 0.0341(12) 0.0413(13) 0.0217(12) 0.0094(10) -0.0019(10) 0.0018(10) _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 2.1070(17) . ? F1 C15 1.335(2) . ? F2 C15 1.343(2) . ? F3 C15 1.332(2) . ? O C8 1.368(2) . ? O C1 1.396(2) . ? N C8 1.277(2) . ? N C7 1.402(2) . ? C1 C16 1.335(2) . ? C1 C2 1.471(2) . ? C2 C3 1.396(3) . ? C2 C7 1.408(2) . ? C3 C4 1.386(3) . ? C3 H3A 0.9500 . ? C4 C5 1.391(3) . ? C4 H4A 0.9500 . ? C5 C6 1.382(3) . ? C5 H5A 0.9500 . ? C6 C7 1.399(2) . ? C6 H6A 0.9500 . ? C8 C9 1.472(3) . ? C9 C14 1.392(2) . ? C9 C10 1.396(2) . ? C10 C11 1.379(3) . ? C10 H10A 0.9500 . ? C11 C12 1.389(3) . ? C11 H11A 0.9500 . ? C12 C13 1.390(3) . ? C12 C15 1.493(3) . ? C13 C14 1.380(3) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C16 C17 1.500(2) . ? C17 C18 1.529(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.528(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.516(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 C8 O C1 118.69(13) . . ? C8 N C7 116.86(16) . . ? C16 C1 O 116.96(16) . . ? C16 C1 C2 129.16(17) . . ? O C1 C2 113.86(15) . . ? C3 C2 C7 119.12(16) . . ? C3 C2 C1 124.59(16) . . ? C7 C2 C1 116.28(16) . . ? C2 C3 C4 120.30(17) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C5 C4 C3 120.18(18) . . ? C5 C4 H4A 119.9 . . ? C3 C4 H4A 119.9 . . ? C4 C5 C6 120.37(17) . . ? C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C5 C6 C7 119.90(17) . . ? C5 C6 H6A 120.1 . . ? C7 C6 H6A 120.1 . . ? C6 C7 C2 119.90(17) . . ? C6 C7 N 118.13(16) . . ? C2 C7 N 121.96(16) . . ? N C8 O 125.58(17) . . ? N C8 C9 122.98(16) . . ? O C8 C9 111.43(14) . . ? C14 C9 C10 119.45(17) . . ? C14 C9 C8 121.28(16) . . ? C10 C9 C8 119.26(16) . . ? C11 C10 C9 120.52(17) . . ? C11 C10 H10A 119.7 . . ? C9 C10 H10A 119.7 . . ? C10 C11 C12 119.72(17) . . ? C10 C11 H11A 120.1 . . ? C12 C11 H11A 120.1 . . ? C11 C12 C13 120.05(17) . . ? C11 C12 C15 120.32(17) . . ? C13 C12 C15 119.59(16) . . ? C12 C13 C14 120.27(17) . . ? C12 C13 H13A 119.9 . . ? C14 C13 H13A 119.9 . . ? C9 C14 C13 119.99(17) . . ? C9 C14 H14A 120.0 . . ? C13 C14 H14A 120.0 . . ? F3 C15 F1 106.79(16) . . ? F3 C15 F2 106.24(17) . . ? F1 C15 F2 105.93(16) . . ? F3 C15 C12 112.70(16) . . ? F1 C15 C12 112.90(16) . . ? F2 C15 C12 111.78(15) . . ? C1 C16 C17 128.23(16) . . ? C1 C16 I 117.75(14) . . ? C17 C16 I 114.02(12) . . ? C16 C17 C18 114.34(15) . . ? C16 C17 H17A 108.7 . . ? C18 C17 H17A 108.7 . . ? C16 C17 H17B 108.7 . . ? C18 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C17 C18 C19 112.99(15) . . ? C17 C18 H18A 109.0 . . ? C19 C18 H18A 109.0 . . ? C17 C18 H18B 109.0 . . ? C19 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C20 C19 C18 112.62(17) . . ? C20 C19 H19A 109.1 . . ? C18 C19 H19A 109.1 . . ? C20 C19 H19B 109.1 . . ? C18 C19 H19B 109.1 . . ? H19A C19 H19B 107.8 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.845 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.383 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.069 _database_code_depnum_ccdc_archive 'CCDC 834788' ####################################################################### # # 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_no2h3ym _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C18 H17 I N2 O3 Si' _chemical_formula_sum 'C18 H17 I N2 O3 Si' _chemical_melting_point ? _exptl_crystal_description parallelepiped _exptl_crystal_colour yellow _diffrn_ambient_temperature 297(2) _chemical_formula_weight 464.33 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 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 6.6498(4) _cell_length_b 20.2549(11) _cell_length_c 14.0362(8) _cell_angle_alpha 90.00 _cell_angle_beta 98.4040(10) _cell_angle_gamma 90.00 _cell_volume 1870.25(19) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 6322 _cell_measurement_theta_min 2.489 _cell_measurement_theta_max 25.982 _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 1.795 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.778417 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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_reflns_number 10400 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 26.02 _reflns_number_total 3668 _reflns_number_gt 3129 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0446P)^2^+0.7617P] 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 3668 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0786 _refine_ls_wR_factor_gt 0.0746 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 I I 0.24964(3) 0.511557(10) 0.924062(16) 0.05829(10) Uani 1 1 d . . . Si Si -0.09671(12) 0.53925(4) 0.73422(6) 0.05005(19) Uani 1 1 d . . . O1 O 0.0889(3) 0.37432(8) 0.90700(12) 0.0426(4) Uani 1 1 d . . . O2 O 0.9003(4) 0.14561(13) 1.0539(2) 0.0872(8) Uani 1 1 d . . . O3 O 0.9950(3) 0.24317(14) 1.09926(18) 0.0731(7) Uani 1 1 d . . . N1 N -0.0280(3) 0.27223(10) 0.84199(15) 0.0392(4) Uani 1 1 d . . . N2 N 0.8685(4) 0.20431(14) 1.06068(17) 0.0542(6) Uani 1 1 d . . . C1 C -0.0464(3) 0.41086(12) 0.84151(17) 0.0383(5) Uani 1 1 d . . . C2 C -0.2251(3) 0.37293(13) 0.80052(17) 0.0385(5) Uani 1 1 d . . . C3 C -0.4135(4) 0.40148(15) 0.7661(2) 0.0487(6) Uani 1 1 d . . . H3A H -0.4301 0.4470 0.7697 0.058 Uiso 1 1 calc R . . C4 C -0.5741(4) 0.36269(17) 0.7271(2) 0.0542(7) Uani 1 1 d . . . H4A H -0.6979 0.3822 0.7033 0.065 Uiso 1 1 calc R . . C5 C -0.5531(4) 0.29493(17) 0.7229(2) 0.0526(7) Uani 1 1 d . . . H5A H -0.6618 0.2692 0.6950 0.063 Uiso 1 1 calc R . . C6 C -0.3719(4) 0.26539(14) 0.76000(18) 0.0462(6) Uani 1 1 d . . . H6A H -0.3590 0.2197 0.7581 0.055 Uiso 1 1 calc R . . C7 C -0.2079(3) 0.30392(12) 0.80032(17) 0.0377(5) Uani 1 1 d . . . C8 C 0.1032(4) 0.30775(12) 0.89279(17) 0.0363(5) Uani 1 1 d . . . C9 C 0.2973(4) 0.28071(12) 0.94228(16) 0.0361(5) Uani 1 1 d . . . C10 C 0.3307(4) 0.21314(13) 0.94301(19) 0.0433(6) Uani 1 1 d . . . H10A H 0.2264 0.1848 0.9175 0.052 Uiso 1 1 calc R . . C11 C 0.5181(4) 0.18750(13) 0.98141(19) 0.0467(6) Uani 1 1 d . . . H11A H 0.5417 0.1423 0.9812 0.056 Uiso 1 1 calc R . . C12 C 0.6685(4) 0.23036(13) 1.01990(18) 0.0412(5) Uani 1 1 d . . . C13 C 0.6381(4) 0.29740(14) 1.02302(19) 0.0447(6) Uani 1 1 d . . . H13A H 0.7416 0.3252 1.0510 0.054 Uiso 1 1 calc R . . C14 C 0.4510(4) 0.32295(13) 0.98386(18) 0.0423(5) Uani 1 1 d . . . H14A H 0.4280 0.3682 0.9853 0.051 Uiso 1 1 calc R . . C15 C -0.0010(4) 0.47426(12) 0.8266(2) 0.0426(6) Uani 1 1 d . . . C16 C -0.2605(7) 0.50671(17) 0.6243(3) 0.0755(11) Uani 1 1 d . . . H16A H -0.3030 0.5426 0.5814 0.113 Uiso 1 1 calc R . . H16B H -0.3779 0.4854 0.6428 0.113 Uiso 1 1 calc R . . H16C H -0.1846 0.4754 0.5925 0.113 Uiso 1 1 calc R . . C17 C -0.2359(6) 0.60218(19) 0.7951(3) 0.0814(11) Uani 1 1 d . . . H17A H -0.2867 0.6358 0.7497 0.122 Uiso 1 1 calc R . . H17B H -0.1455 0.6217 0.8471 0.122 Uiso 1 1 calc R . . H17C H -0.3475 0.5816 0.8200 0.122 Uiso 1 1 calc R . . C18 C 0.1313(6) 0.5766(3) 0.6920(4) 0.1036(16) Uani 1 1 d . . . H18A H 0.0888 0.6100 0.6448 0.155 Uiso 1 1 calc R . . H18B H 0.2056 0.5430 0.6638 0.155 Uiso 1 1 calc R . . H18C H 0.2169 0.5961 0.7457 0.155 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 0.04882(13) 0.04140(13) 0.07870(17) -0.00636(8) -0.01062(10) -0.00559(7) Si 0.0474(4) 0.0409(4) 0.0608(5) 0.0092(3) 0.0043(3) 0.0059(3) O1 0.0400(9) 0.0338(9) 0.0487(10) -0.0011(7) -0.0109(7) 0.0006(7) O2 0.0648(15) 0.0647(16) 0.125(2) 0.0151(15) -0.0089(15) 0.0248(12) O3 0.0411(11) 0.0904(18) 0.0810(16) 0.0025(13) -0.0144(11) 0.0060(11) N1 0.0360(10) 0.0377(11) 0.0418(11) -0.0011(9) -0.0018(8) -0.0024(8) N2 0.0410(12) 0.0678(17) 0.0526(14) 0.0142(12) 0.0027(10) 0.0096(12) C1 0.0333(12) 0.0402(13) 0.0399(12) 0.0006(10) 0.0008(10) 0.0049(9) C2 0.0316(11) 0.0454(13) 0.0377(12) 0.0023(10) 0.0019(9) 0.0012(10) C3 0.0380(13) 0.0548(16) 0.0521(15) 0.0070(12) 0.0027(11) 0.0063(11) C4 0.0310(13) 0.080(2) 0.0493(15) 0.0088(14) -0.0018(11) 0.0039(13) C5 0.0358(13) 0.074(2) 0.0455(15) -0.0036(13) -0.0033(11) -0.0104(13) C6 0.0422(14) 0.0527(15) 0.0421(13) -0.0026(12) 0.0003(11) -0.0080(11) C7 0.0340(12) 0.0447(13) 0.0336(12) 0.0002(10) 0.0027(9) -0.0043(10) C8 0.0354(12) 0.0354(12) 0.0373(12) 0.0008(10) 0.0027(9) 0.0001(9) C9 0.0348(12) 0.0395(13) 0.0327(12) 0.0018(9) 0.0004(9) 0.0002(10) C10 0.0416(13) 0.0368(13) 0.0491(14) -0.0026(11) -0.0015(11) -0.0041(10) C11 0.0485(15) 0.0376(13) 0.0527(15) 0.0037(11) 0.0034(12) 0.0047(11) C12 0.0358(12) 0.0497(14) 0.0369(12) 0.0066(11) 0.0011(10) 0.0053(11) C13 0.0379(13) 0.0477(15) 0.0448(14) 0.0005(11) -0.0060(10) -0.0048(11) C14 0.0422(13) 0.0365(13) 0.0455(14) -0.0005(10) -0.0030(10) -0.0004(10) C15 0.0357(12) 0.0373(13) 0.0525(15) -0.0003(11) -0.0011(10) 0.0036(10) C16 0.110(3) 0.0583(19) 0.0520(19) 0.0130(15) -0.0105(18) 0.0057(19) C17 0.094(3) 0.062(2) 0.086(3) 0.0001(19) 0.006(2) 0.030(2) C18 0.068(2) 0.118(4) 0.125(4) 0.065(3) 0.016(2) -0.006(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 I C15 2.134(3) . ? Si C17 1.855(4) . ? Si C16 1.873(4) . ? Si C18 1.867(4) . ? Si C15 1.892(3) . ? O1 C8 1.368(3) . ? O1 C1 1.400(3) . ? O2 N2 1.214(4) . ? O3 N2 1.219(3) . ? N1 C8 1.267(3) . ? N1 C7 1.407(3) . ? N2 C12 1.467(3) . ? C1 C15 1.342(4) . ? C1 C2 1.461(3) . ? C2 C3 1.401(3) . ? C2 C7 1.403(4) . ? C3 C4 1.373(4) . ? C3 H3A 0.9300 . ? C4 C5 1.382(5) . ? C4 H4A 0.9300 . ? C5 C6 1.378(4) . ? C5 H5A 0.9300 . ? C6 C7 1.392(3) . ? C6 H6A 0.9300 . ? C8 C9 1.479(3) . ? C9 C10 1.386(4) . ? C9 C14 1.394(3) . ? C10 C11 1.385(4) . ? C10 H10A 0.9300 . ? C11 C12 1.374(4) . ? C11 H11A 0.9300 . ? C12 C13 1.374(4) . ? C13 C14 1.385(4) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 C17 Si C16 110.6(2) . . ? C17 Si C18 110.5(2) . . ? C16 Si C18 106.4(2) . . ? C17 Si C15 107.63(15) . . ? C16 Si C15 114.61(14) . . ? C18 Si C15 106.98(16) . . ? C8 O1 C1 118.47(19) . . ? C8 N1 C7 116.6(2) . . ? O3 N2 O2 123.4(3) . . ? O3 N2 C12 117.9(3) . . ? O2 N2 C12 118.7(3) . . ? C15 C1 O1 118.1(2) . . ? C15 C1 C2 129.1(2) . . ? O1 C1 C2 112.8(2) . . ? C3 C2 C7 118.7(2) . . ? C3 C2 C1 123.7(2) . . ? C7 C2 C1 117.6(2) . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C3 C4 C5 120.5(3) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? C5 C6 C7 120.0(3) . . ? C5 C6 H6A 120.0 . . ? C7 C6 H6A 120.0 . . ? C6 C7 N1 118.8(2) . . ? C6 C7 C2 120.0(2) . . ? N1 C7 C2 121.2(2) . . ? N1 C8 O1 125.8(2) . . ? N1 C8 C9 122.4(2) . . ? O1 C8 C9 111.8(2) . . ? C10 C9 C14 119.7(2) . . ? C10 C9 C8 119.8(2) . . ? C14 C9 C8 120.4(2) . . ? C9 C10 C11 120.5(2) . . ? C9 C10 H10A 119.8 . . ? C11 C10 H10A 119.8 . . ? C12 C11 C10 118.6(2) . . ? C12 C11 H11A 120.7 . . ? C10 C11 H11A 120.7 . . ? C11 C12 C13 122.3(2) . . ? C11 C12 N2 119.5(2) . . ? C13 C12 N2 118.1(2) . . ? C12 C13 C14 119.0(2) . . ? C12 C13 H13A 120.5 . . ? C14 C13 H13A 120.5 . . ? C9 C14 C13 119.9(2) . . ? C9 C14 H14A 120.1 . . ? C13 C14 H14A 120.1 . . ? C1 C15 Si 135.4(2) . . ? C1 C15 I 114.28(19) . . ? Si C15 I 110.25(12) . . ? Si C16 H16A 109.5 . . ? Si C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? Si C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? Si C17 H17A 109.5 . . ? Si C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? Si C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.638 _refine_diff_density_min -0.646 _refine_diff_density_rms 0.072 _database_code_depnum_ccdc_archive 'CCDC 834789' ####################################################################### # # 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_4f _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C22 H13 F3 I N O' _chemical_formula_sum 'C22 H13 F3 I N O' _chemical_melting_point ? _exptl_crystal_description parallelepiped _exptl_crystal_colour yellow _diffrn_ambient_temperature 110(2) _chemical_formula_weight 491.23 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' 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' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1298(2) _cell_length_b 10.6900(3) _cell_length_c 11.1738(3) _cell_angle_alpha 80.375(2) _cell_angle_beta 87.307(2) _cell_angle_gamma 73.916(2) _cell_volume 919.94(4) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 6245 _cell_measurement_theta_min 2.9351 _cell_measurement_theta_max 29.2175 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.773 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 1.782 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.85697 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8019 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 29.28 _reflns_number_total 4233 _reflns_number_gt 3716 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0371P)^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 4233 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0299 _refine_ls_R_factor_gt 0.0243 _refine_ls_wR_factor_ref 0.0611 _refine_ls_wR_factor_gt 0.0599 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _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 0.37326(2) 0.712260(15) 0.726843(14) 0.02075(6) Uani 1 1 d . . . F1 F 0.1975(2) 0.76738(15) 0.08186(14) 0.0359(4) Uani 1 1 d . . . F2 F 0.34000(19) 0.58494(17) 0.02828(14) 0.0334(4) Uani 1 1 d . . . F3 F 0.06694(19) 0.64466(17) 0.01301(13) 0.0340(4) Uani 1 1 d . . . O O 0.3282(2) 0.47551(15) 0.63396(14) 0.0171(3) Uani 1 1 d . . . N N 0.1901(2) 0.34340(19) 0.55219(18) 0.0177(4) Uani 1 1 d . . . C1 C 0.2912(3) 0.5770(2) 0.5340(2) 0.0152(4) Uani 1 1 d . . . C2 C 0.2431(3) 0.5380(2) 0.4233(2) 0.0149(4) Uani 1 1 d . . . C3 C 0.2478(3) 0.6085(2) 0.3068(2) 0.0168(5) Uani 1 1 d . . . H3A H 0.2939 0.6822 0.2940 0.020 Uiso 1 1 calc R . . C4 C 0.1845(3) 0.5699(2) 0.2097(2) 0.0169(5) Uani 1 1 d . . . C5 C 0.1175(3) 0.4620(2) 0.2266(2) 0.0191(5) Uani 1 1 d . . . H5A H 0.0705 0.4389 0.1600 0.023 Uiso 1 1 calc R . . C6 C 0.1197(3) 0.3886(2) 0.3407(2) 0.0187(5) Uani 1 1 d . . . H6A H 0.0768 0.3133 0.3524 0.022 Uiso 1 1 calc R . . C7 C 0.1849(3) 0.4250(2) 0.4391(2) 0.0158(5) Uani 1 1 d . . . C8 C 0.2622(3) 0.3702(2) 0.6392(2) 0.0162(5) Uani 1 1 d . . . C9 C 0.2870(3) 0.2870(2) 0.7595(2) 0.0198(5) Uani 1 1 d . . . C10 C 0.2529(3) 0.1648(3) 0.7737(2) 0.0272(6) Uani 1 1 d . . . H10A H 0.2167 0.1356 0.7063 0.033 Uiso 1 1 calc R . . C11 C 0.2720(4) 0.0858(3) 0.8868(3) 0.0325(6) Uani 1 1 d . . . H11A H 0.2495 0.0021 0.8965 0.039 Uiso 1 1 calc R . . C12 C 0.3235(3) 0.1277(3) 0.9852(2) 0.0312(6) Uani 1 1 d . . . H12A H 0.3350 0.0736 1.0626 0.037 Uiso 1 1 calc R . . C13 C 0.3580(3) 0.2482(3) 0.9710(2) 0.0300(6) Uani 1 1 d . . . H13A H 0.3956 0.2759 1.0388 0.036 Uiso 1 1 calc R . . C14 C 0.3389(3) 0.3300(3) 0.8590(2) 0.0241(5) Uani 1 1 d . . . H14A H 0.3608 0.4138 0.8504 0.029 Uiso 1 1 calc R . . C15 C 0.3041(3) 0.6945(2) 0.5528(2) 0.0162(5) Uani 1 1 d . . . C16 C 0.2600(3) 0.8193(2) 0.4649(2) 0.0168(5) Uani 1 1 d . . . C17 C 0.3804(3) 0.8898(3) 0.4319(2) 0.0242(5) Uani 1 1 d . . . H17A H 0.4916 0.8588 0.4666 0.029 Uiso 1 1 calc R . . C18 C 0.3373(4) 1.0054(3) 0.3480(3) 0.0300(6) Uani 1 1 d . . . H18A H 0.4199 1.0528 0.3250 0.036 Uiso 1 1 calc R . . C19 C 0.1755(4) 1.0517(3) 0.2979(2) 0.0272(6) Uani 1 1 d . . . H19A H 0.1468 1.1305 0.2403 0.033 Uiso 1 1 calc R . . C20 C 0.0552(3) 0.9826(2) 0.3321(2) 0.0245(5) Uani 1 1 d . . . H20A H -0.0562 1.0144 0.2977 0.029 Uiso 1 1 calc R . . C21 C 0.0960(3) 0.8681(2) 0.4156(2) 0.0204(5) Uani 1 1 d . . . H21A H 0.0120 0.8223 0.4396 0.025 Uiso 1 1 calc R . . C22 C 0.1959(3) 0.6425(3) 0.0846(2) 0.0225(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I 0.02443(9) 0.02188(9) 0.01677(9) -0.00615(6) -0.00503(6) -0.00509(6) F1 0.0609(11) 0.0262(9) 0.0203(8) 0.0021(7) -0.0026(8) -0.0146(8) F2 0.0269(8) 0.0473(10) 0.0197(8) -0.0033(7) 0.0078(6) -0.0022(7) F3 0.0301(8) 0.0517(11) 0.0200(8) 0.0018(7) -0.0106(7) -0.0138(8) O 0.0207(8) 0.0172(8) 0.0138(8) -0.0009(6) -0.0042(7) -0.0065(7) N 0.0183(9) 0.0171(10) 0.0179(10) -0.0026(8) -0.0008(8) -0.0049(8) C1 0.0136(10) 0.0190(12) 0.0127(10) -0.0004(9) 0.0004(8) -0.0052(9) C2 0.0126(10) 0.0156(11) 0.0163(11) -0.0053(9) -0.0002(9) -0.0019(9) C3 0.0166(11) 0.0171(12) 0.0173(11) -0.0056(9) 0.0014(9) -0.0040(9) C4 0.0146(10) 0.0183(12) 0.0155(11) -0.0036(9) 0.0009(9) -0.0005(9) C5 0.0168(11) 0.0225(13) 0.0189(12) -0.0092(10) -0.0034(9) -0.0030(9) C6 0.0190(11) 0.0185(12) 0.0213(12) -0.0086(10) -0.0003(10) -0.0066(9) C7 0.0132(10) 0.0161(11) 0.0172(11) -0.0046(9) -0.0007(9) -0.0011(9) C8 0.0137(10) 0.0135(11) 0.0204(12) -0.0021(9) 0.0002(9) -0.0026(9) C9 0.0160(11) 0.0207(12) 0.0195(12) 0.0019(10) -0.0002(9) -0.0026(9) C10 0.0337(14) 0.0244(14) 0.0231(13) 0.0020(11) -0.0053(11) -0.0098(11) C11 0.0377(15) 0.0254(15) 0.0310(15) 0.0080(12) -0.0025(13) -0.0098(12) C12 0.0270(13) 0.0365(16) 0.0207(13) 0.0089(11) -0.0007(11) -0.0009(12) C13 0.0280(13) 0.0406(17) 0.0171(12) 0.0014(11) -0.0037(11) -0.0051(12) C14 0.0246(12) 0.0259(14) 0.0204(12) -0.0018(10) -0.0014(10) -0.0054(11) C15 0.0159(10) 0.0207(12) 0.0131(11) -0.0038(9) -0.0009(9) -0.0060(9) C16 0.0218(11) 0.0157(11) 0.0150(11) -0.0064(9) 0.0009(9) -0.0062(9) C17 0.0275(13) 0.0247(14) 0.0235(13) -0.0054(11) 0.0007(11) -0.0114(11) C18 0.0407(15) 0.0244(14) 0.0311(15) -0.0041(11) 0.0041(13) -0.0197(12) C19 0.0461(16) 0.0162(13) 0.0186(12) -0.0038(10) 0.0009(12) -0.0072(12) C20 0.0305(13) 0.0189(13) 0.0217(13) -0.0043(10) -0.0034(11) -0.0014(10) C21 0.0217(12) 0.0173(12) 0.0219(12) -0.0050(10) 0.0010(10) -0.0037(10) C22 0.0234(12) 0.0256(14) 0.0183(12) -0.0033(10) -0.0015(10) -0.0065(10) _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 2.103(2) . ? F1 C22 1.334(3) . ? F2 C22 1.345(3) . ? F3 C22 1.341(3) . ? O C8 1.367(3) . ? O C1 1.400(3) . ? N C8 1.269(3) . ? N C7 1.405(3) . ? C1 C15 1.340(3) . ? C1 C2 1.472(3) . ? C2 C7 1.397(3) . ? C2 C3 1.395(3) . ? C3 C4 1.390(3) . ? C3 H3A 0.9500 . ? C4 C5 1.389(3) . ? C4 C22 1.492(3) . ? C5 C6 1.379(3) . ? C5 H5A 0.9500 . ? C6 C7 1.398(3) . ? C6 H6A 0.9500 . ? C8 C9 1.471(3) . ? C9 C10 1.392(4) . ? C9 C14 1.396(3) . ? C10 C11 1.387(4) . ? C10 H10A 0.9500 . ? C11 C12 1.377(4) . ? C11 H11A 0.9500 . ? C12 C13 1.375(4) . ? C12 H12A 0.9500 . ? C13 C14 1.389(4) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 C16 1.484(3) . ? C16 C21 1.393(3) . ? C16 C17 1.394(3) . ? C17 C18 1.390(4) . ? C17 H17A 0.9500 . ? C18 C19 1.380(4) . ? C18 H18A 0.9500 . ? C19 C20 1.385(4) . ? C19 H19A 0.9500 . ? C20 C21 1.379(3) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O C1 119.61(17) . . ? C8 N C7 117.4(2) . . ? C15 C1 O 115.9(2) . . ? C15 C1 C2 129.6(2) . . ? O C1 C2 114.51(19) . . ? C7 C2 C3 119.4(2) . . ? C7 C2 C1 116.5(2) . . ? C3 C2 C1 124.1(2) . . ? C4 C3 C2 119.4(2) . . ? C4 C3 H3A 120.3 . . ? C2 C3 H3A 120.3 . . ? C5 C4 C3 121.1(2) . . ? C5 C4 C22 119.7(2) . . ? C3 C4 C22 119.2(2) . . ? C4 C5 C6 119.6(2) . . ? C4 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? C5 C6 C7 120.0(2) . . ? C5 C6 H6A 120.0 . . ? C7 C6 H6A 120.0 . . ? C6 C7 C2 120.3(2) . . ? C6 C7 N 117.4(2) . . ? C2 C7 N 122.3(2) . . ? N C8 O 125.5(2) . . ? N C8 C9 122.7(2) . . ? O C8 C9 111.78(19) . . ? C10 C9 C14 119.9(2) . . ? C10 C9 C8 118.7(2) . . ? C14 C9 C8 121.4(2) . . ? C11 C10 C9 119.7(3) . . ? C11 C10 H10A 120.1 . . ? C9 C10 H10A 120.1 . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H11A 119.8 . . ? C10 C11 H11A 119.8 . . ? C11 C12 C13 119.8(3) . . ? C11 C12 H12A 120.1 . . ? C13 C12 H12A 120.1 . . ? C14 C13 C12 121.0(3) . . ? C14 C13 H13A 119.5 . . ? C12 C13 H13A 119.5 . . ? C13 C14 C9 119.0(2) . . ? C13 C14 H14A 120.5 . . ? C9 C14 H14A 120.5 . . ? C1 C15 C16 126.3(2) . . ? C1 C15 I 118.31(17) . . ? C16 C15 I 115.16(15) . . ? C21 C16 C17 119.3(2) . . ? C21 C16 C15 120.0(2) . . ? C17 C16 C15 120.8(2) . . ? C18 C17 C16 119.9(2) . . ? C18 C17 H17A 120.1 . . ? C16 C17 H17A 120.1 . . ? C19 C18 C17 120.5(2) . . ? C19 C18 H18A 119.8 . . ? C17 C18 H18A 119.8 . . ? C18 C19 C20 119.6(2) . . ? C18 C19 H19A 120.2 . . ? C20 C19 H19A 120.2 . . ? C21 C20 C19 120.5(2) . . ? C21 C20 H20A 119.8 . . ? C19 C20 H20A 119.8 . . ? C20 C21 C16 120.2(2) . . ? C20 C21 H21A 119.9 . . ? C16 C21 H21A 119.9 . . ? F1 C22 F3 107.0(2) . . ? F1 C22 F2 106.0(2) . . ? F3 C22 F2 105.62(19) . . ? F1 C22 C4 113.7(2) . . ? F3 C22 C4 112.6(2) . . ? F2 C22 C4 111.3(2) . . ? _diffrn_measured_fraction_theta_max 0.841 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.621 _refine_diff_density_min -0.634 _refine_diff_density_rms 0.091 _database_code_depnum_ccdc_archive 'CCDC 837880' ####################################################################### # # 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_nhnphm _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H17 N3 O3' _chemical_formula_sum 'C26 H17 N3 O3' _chemical_formula_weight 419.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_int_tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 31.297(3) _cell_length_b 8.1567(7) _cell_length_c 18.7872(16) _cell_angle_alpha 90.00 _cell_angle_beta 119.988(2) _cell_angle_gamma 90.00 _cell_volume 4153.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3370 _cell_measurement_theta_min 2.504 _cell_measurement_theta_max 25.430 _exptl_crystal_description parallelepiped _exptl_crystal_colour red _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.788340 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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_% ? _diffrn_reflns_number 11428 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 26.04 _reflns_number_total 4083 _reflns_number_gt 2579 _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^)+(0.0676P)^2^+0.7162P] 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 constro _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4083 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1128 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 O1 O 0.18775(4) 0.40132(15) 0.47631(7) 0.0506(3) Uani 1 1 d . . . O2 O 0.34085(7) 0.8654(2) 0.40073(11) 0.0864(5) Uani 1 1 d . . . O3 O 0.40388(6) 0.7742(2) 0.51128(11) 0.0914(5) Uani 1 1 d . . . N1 N 0.24958(5) 0.35010(17) 0.61067(8) 0.0444(4) Uani 1 1 d . . . N2 N 0.05617(7) 0.6363(3) 0.24088(13) 0.0953(7) Uani 1 1 d . . . N3 N 0.35949(7) 0.7841(2) 0.46394(13) 0.0635(5) Uani 1 1 d . . . C1 C 0.21577(6) 0.25782(19) 0.62302(9) 0.0397(4) Uani 1 1 d . . . C2 C 0.23384(7) 0.1833(2) 0.69950(10) 0.0494(4) Uani 1 1 d . . . H2B H 0.2666 0.1983 0.7398 0.059 Uiso 1 1 calc R . . C3 C 0.20361(7) 0.0879(2) 0.71566(11) 0.0545(5) Uani 1 1 d . . . H3A H 0.2155 0.0406 0.7672 0.065 Uiso 1 1 calc R . . C4 C 0.15548(7) 0.0627(2) 0.65501(12) 0.0570(5) Uani 1 1 d . . . H4A H 0.1351 -0.0034 0.6656 0.068 Uiso 1 1 calc R . . C5 C 0.13711(7) 0.1343(2) 0.57880(11) 0.0508(5) Uani 1 1 d . . . H5A H 0.1046 0.1145 0.5384 0.061 Uiso 1 1 calc R . . C6 C 0.16655(6) 0.23622(19) 0.56116(9) 0.0397(4) Uani 1 1 d . . . C7 C 0.15013(6) 0.3197(2) 0.48253(10) 0.0397(4) Uani 1 1 d . . . C8 C 0.10547(6) 0.3347(2) 0.41464(10) 0.0465(4) Uani 1 1 d . . . C9 C 0.05983(6) 0.2682(3) 0.41057(12) 0.0593(5) Uani 1 1 d . . . C10 C 0.04023(8) 0.3399(3) 0.45481(17) 0.0853(7) Uani 1 1 d . . . H10A H 0.0546 0.4344 0.4851 0.102 Uiso 1 1 calc R . . C11 C -0.00019(11) 0.2736(5) 0.4547(2) 0.1214(12) Uani 1 1 d . . . H11A H -0.0128 0.3224 0.4851 0.146 Uiso 1 1 calc R . . C12 C -0.02173(11) 0.1355(6) 0.4097(3) 0.1377(17) Uani 1 1 d . . . H12A H -0.0489 0.0901 0.4101 0.165 Uiso 1 1 calc R . . C13 C -0.00368(12) 0.0621(5) 0.3633(2) 0.1331(15) Uani 1 1 d . . . H13A H -0.0188 -0.0312 0.3324 0.160 Uiso 1 1 calc R . . C14 C 0.03759(9) 0.1300(4) 0.36344(15) 0.0955(9) Uani 1 1 d . . . H14A H 0.0499 0.0828 0.3323 0.115 Uiso 1 1 calc R . . C15 C 0.09886(6) 0.4226(2) 0.34039(10) 0.0516(5) Uani 1 1 d . . . C16 C 0.12645(8) 0.3889(3) 0.30292(12) 0.0684(6) Uani 1 1 d . . . H16A H 0.1503 0.3070 0.3234 0.082 Uiso 1 1 calc R . . C17 C 0.11798(10) 0.4792(4) 0.23455(14) 0.0893(8) Uani 1 1 d . . . H17A H 0.1356 0.4577 0.2078 0.107 Uiso 1 1 calc R . . C18 C 0.08303(10) 0.6009(4) 0.20704(15) 0.0973(9) Uani 1 1 d . . . H18A H 0.0781 0.6621 0.1617 0.117 Uiso 1 1 calc R . . C19 C 0.06404(7) 0.5460(3) 0.30540(12) 0.0712(6) Uani 1 1 d . . . H19A H 0.0446 0.5677 0.3289 0.085 Uiso 1 1 calc R . . C20 C 0.23405(6) 0.41339(19) 0.54056(9) 0.0373(4) Uani 1 1 d . . . C21 C 0.26609(6) 0.51172(19) 0.52036(10) 0.0387(4) Uani 1 1 d . . . C22 C 0.24866(6) 0.5746(2) 0.44200(10) 0.0443(4) Uani 1 1 d . . . H22A H 0.2162 0.5548 0.4014 0.053 Uiso 1 1 calc R . . C23 C 0.27902(7) 0.6663(2) 0.42388(11) 0.0492(4) Uani 1 1 d . . . H23A H 0.2674 0.7094 0.3716 0.059 Uiso 1 1 calc R . . C24 C 0.32682(7) 0.6923(2) 0.48491(12) 0.0486(4) Uani 1 1 d . . . C25 C 0.34527(7) 0.6332(2) 0.56347(12) 0.0530(5) Uani 1 1 d . . . H25A H 0.3778 0.6536 0.6037 0.064 Uiso 1 1 calc R . . C26 C 0.31462(6) 0.5433(2) 0.58115(11) 0.0473(4) Uani 1 1 d . . . H26A H 0.3263 0.5033 0.6341 0.057 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 O1 0.0381(6) 0.0687(8) 0.0407(7) 0.0096(6) 0.0163(5) -0.0070(6) O2 0.1121(13) 0.0790(11) 0.0918(12) 0.0119(9) 0.0687(11) -0.0179(10) O3 0.0689(11) 0.0976(13) 0.1247(14) 0.0058(11) 0.0612(11) -0.0175(9) N1 0.0444(8) 0.0496(8) 0.0389(8) -0.0005(6) 0.0206(7) -0.0047(7) N2 0.0719(13) 0.1270(19) 0.0778(14) 0.0503(13) 0.0305(11) 0.0130(12) N3 0.0733(12) 0.0522(10) 0.0889(13) -0.0099(10) 0.0586(11) -0.0121(9) C1 0.0483(9) 0.0371(9) 0.0378(9) -0.0021(7) 0.0245(8) 0.0009(7) C2 0.0540(10) 0.0529(11) 0.0395(9) 0.0011(8) 0.0219(8) -0.0006(9) C3 0.0710(13) 0.0535(11) 0.0452(10) 0.0079(8) 0.0337(10) 0.0033(9) C4 0.0649(12) 0.0563(12) 0.0590(12) 0.0078(9) 0.0380(10) -0.0047(10) C5 0.0482(10) 0.0529(11) 0.0531(11) 0.0059(9) 0.0267(9) -0.0036(8) C6 0.0438(9) 0.0379(9) 0.0414(9) -0.0007(7) 0.0243(8) 0.0021(7) C7 0.0408(9) 0.0404(9) 0.0433(9) -0.0008(7) 0.0249(8) -0.0024(7) C8 0.0411(9) 0.0520(10) 0.0458(10) 0.0028(8) 0.0212(8) -0.0016(8) C9 0.0375(10) 0.0756(14) 0.0548(11) 0.0215(10) 0.0155(9) -0.0022(10) C10 0.0685(15) 0.0819(16) 0.129(2) 0.0277(15) 0.0672(15) 0.0124(13) C11 0.0794(19) 0.133(3) 0.187(3) 0.064(3) 0.093(2) 0.023(2) C12 0.0572(18) 0.195(4) 0.139(3) 0.062(3) 0.0330(19) -0.027(2) C13 0.092(2) 0.169(4) 0.091(2) 0.020(2) 0.0103(18) -0.074(2) C14 0.0750(16) 0.124(2) 0.0622(14) 0.0017(14) 0.0154(12) -0.0462(16) C15 0.0388(9) 0.0664(12) 0.0420(10) 0.0035(9) 0.0144(8) -0.0073(9) C16 0.0665(13) 0.0896(16) 0.0492(11) 0.0020(11) 0.0291(10) -0.0005(12) C17 0.0840(17) 0.137(2) 0.0562(14) 0.0040(15) 0.0421(13) -0.0120(18) C18 0.0747(17) 0.143(3) 0.0594(15) 0.0363(16) 0.0225(13) -0.0075(17) C19 0.0496(11) 0.0971(16) 0.0610(13) 0.0283(12) 0.0233(10) 0.0055(11) C20 0.0385(9) 0.0380(9) 0.0369(9) -0.0062(7) 0.0199(7) -0.0001(7) C21 0.0431(9) 0.0362(9) 0.0432(9) -0.0039(7) 0.0263(8) 0.0016(7) C22 0.0473(10) 0.0436(10) 0.0458(10) -0.0019(8) 0.0261(8) 0.0003(8) C23 0.0632(12) 0.0447(10) 0.0523(11) 0.0034(8) 0.0383(10) 0.0029(9) C24 0.0566(11) 0.0383(9) 0.0675(12) -0.0062(8) 0.0434(10) -0.0053(8) C25 0.0444(10) 0.0529(11) 0.0623(12) -0.0051(9) 0.0271(9) -0.0064(8) C26 0.0454(10) 0.0500(10) 0.0474(10) 0.0004(8) 0.0239(8) -0.0032(8) _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 O1 C20 1.3482(19) . ? O1 C7 1.4076(19) . ? O2 N3 1.224(2) . ? O3 N3 1.222(2) . ? N1 C20 1.264(2) . ? N1 C1 1.409(2) . ? N2 C18 1.315(3) . ? N2 C19 1.332(3) . ? N3 C24 1.471(2) . ? C1 C2 1.393(2) . ? C1 C6 1.402(2) . ? C2 C3 1.371(2) . ? C2 H2B 0.9300 . ? C3 C4 1.376(3) . ? C3 H3A 0.9300 . ? C4 C5 1.378(2) . ? C4 H4A 0.9300 . ? C5 C6 1.398(2) . ? C5 H5A 0.9300 . ? C6 C7 1.467(2) . ? C7 C8 1.347(2) . ? C8 C15 1.488(2) . ? C8 C9 1.494(2) . ? C9 C14 1.387(3) . ? C9 C10 1.385(3) . ? C10 C11 1.375(3) . ? C10 H10A 0.9300 . ? C11 C12 1.367(5) . ? C11 H11A 0.9300 . ? C12 C13 1.389(5) . ? C12 H12A 0.9300 . ? C13 C14 1.404(4) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C19 1.385(3) . ? C15 C16 1.387(3) . ? C16 C17 1.386(3) . ? C16 H16A 0.9300 . ? C17 C18 1.373(4) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C20 C21 1.474(2) . ? C21 C22 1.388(2) . ? C21 C26 1.394(2) . ? C22 C23 1.379(2) . ? C22 H22A 0.9300 . ? C23 C24 1.372(2) . ? C23 H23A 0.9300 . ? C24 C25 1.376(3) . ? C25 C26 1.373(2) . ? C25 H25A 0.9300 . ? C26 H26A 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 C20 O1 C7 121.97(12) . . ? C20 N1 C1 117.41(14) . . ? C18 N2 C19 116.5(2) . . ? O3 N3 O2 124.03(18) . . ? O3 N3 C24 117.44(19) . . ? O2 N3 C24 118.53(19) . . ? C2 C1 C6 120.77(16) . . ? C2 C1 N1 116.85(15) . . ? C6 C1 N1 122.35(14) . . ? C3 C2 C1 120.44(17) . . ? C3 C2 H2B 119.8 . . ? C1 C2 H2B 119.8 . . ? C2 C3 C4 119.49(17) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C3 C4 C5 120.83(18) . . ? C3 C4 H4A 119.6 . . ? C5 C4 H4A 119.6 . . ? C4 C5 C6 121.08(17) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C1 C6 C5 117.35(15) . . ? C1 C6 C7 117.61(14) . . ? C5 C6 C7 125.03(15) . . ? C8 C7 O1 113.18(14) . . ? C8 C7 C6 132.19(15) . . ? O1 C7 C6 114.62(13) . . ? C7 C8 C15 121.59(15) . . ? C7 C8 C9 121.92(15) . . ? C15 C8 C9 116.47(14) . . ? C14 C9 C10 119.7(2) . . ? C14 C9 C8 119.3(2) . . ? C10 C9 C8 121.0(2) . . ? C11 C10 C9 121.1(3) . . ? C11 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? C12 C11 C10 119.6(3) . . ? C12 C11 H11A 120.2 . . ? C10 C11 H11A 120.2 . . ? C11 C12 C13 120.9(3) . . ? C11 C12 H12A 119.5 . . ? C13 C12 H12A 119.5 . . ? C12 C13 C14 119.4(3) . . ? C12 C13 H13A 120.3 . . ? C14 C13 H13A 120.3 . . ? C9 C14 C13 119.3(3) . . ? C9 C14 H14A 120.4 . . ? C13 C14 H14A 120.4 . . ? C19 C15 C16 116.41(18) . . ? C19 C15 C8 120.19(17) . . ? C16 C15 C8 123.40(17) . . ? C15 C16 C17 119.1(2) . . ? C15 C16 H16A 120.5 . . ? C17 C16 H16A 120.5 . . ? C18 C17 C16 118.7(2) . . ? C18 C17 H17A 120.6 . . ? C16 C17 H17A 120.6 . . ? N2 C18 C17 124.0(2) . . ? N2 C18 H18A 118.0 . . ? C17 C18 H18A 118.0 . . ? N2 C19 C15 125.3(2) . . ? N2 C19 H19A 117.4 . . ? C15 C19 H19A 117.4 . . ? N1 C20 O1 125.77(15) . . ? N1 C20 C21 122.25(14) . . ? O1 C20 C21 111.98(13) . . ? C22 C21 C26 119.37(16) . . ? C22 C21 C20 121.12(14) . . ? C26 C21 C20 119.51(15) . . ? C23 C22 C21 120.55(16) . . ? C23 C22 H22A 119.7 . . ? C21 C22 H22A 119.7 . . ? C24 C23 C22 118.41(16) . . ? C24 C23 H23A 120.8 . . ? C22 C23 H23A 120.8 . . ? C23 C24 C25 122.66(17) . . ? C23 C24 N3 117.94(18) . . ? C25 C24 N3 119.38(17) . . ? C26 C25 C24 118.51(17) . . ? C26 C25 H25A 120.7 . . ? C24 C25 H25A 120.7 . . ? C25 C26 C21 120.47(17) . . ? C25 C26 H26A 119.8 . . ? C21 C26 H26A 119.8 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.231 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.034 _database_code_depnum_ccdc_archive 'CCDC 951676' ####################################################################### # # 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_nppcy _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H18 N2 O4' _chemical_formula_sum 'C27 H18 N2 O4' _chemical_formula_weight 434.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.0042(3) _cell_length_b 14.4363(3) _cell_length_c 12.4330(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.177(3) _cell_angle_gamma 90.00 _cell_volume 2069.28(9) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 7388 _cell_measurement_theta_min 2.5128 _cell_measurement_theta_max 29.1272 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98997 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17616 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 29.20 _reflns_number_total 4858 _reflns_number_gt 3064 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _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^)+(0.0250P)^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 constro _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4858 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0660 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0698 _refine_ls_wR_factor_gt 0.0674 _refine_ls_goodness_of_fit_ref 1.182 _refine_ls_restrained_S_all 1.182 _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 O1 O 0.21259(7) 0.08340(6) 0.13668(7) 0.0544(2) Uani 1 1 d . . . O2 O 0.66794(7) 0.21084(6) 0.17929(8) 0.0629(3) Uani 1 1 d . . . O3 O 0.56218(10) 0.62752(7) 0.42813(12) 0.0928(4) Uani 1 1 d . . . O4 O 0.53559(9) 0.66666(7) 0.25462(11) 0.0887(4) Uani 1 1 d . . . N1 N 0.50169(7) 0.16551(6) 0.21499(7) 0.0340(2) Uani 1 1 d . . . N2 N 0.55194(9) 0.60940(9) 0.32978(14) 0.0636(3) Uani 1 1 d . . . C1 C 0.51292(9) 0.07174(8) 0.18638(9) 0.0359(3) Uani 1 1 d . . . C2 C 0.61300(10) 0.02254(9) 0.18882(10) 0.0472(3) Uani 1 1 d . . . H2A H 0.6855 0.0508 0.2090 0.057 Uiso 1 1 calc R . . C3 C 0.60066(12) -0.06966(9) 0.16014(11) 0.0582(4) Uani 1 1 d . . . H3A H 0.6668 -0.1041 0.1626 0.070 Uiso 1 1 calc R . . C4 C 0.49428(12) -0.11313(9) 0.12792(12) 0.0616(4) Uani 1 1 d . . . H4A H 0.4898 -0.1756 0.1088 0.074 Uiso 1 1 calc R . . C5 C 0.39507(11) -0.06446(9) 0.12400(11) 0.0524(3) Uani 1 1 d . . . H5A H 0.3227 -0.0927 0.1011 0.063 Uiso 1 1 calc R . . C6 C 0.40577(9) 0.02791(8) 0.15506(9) 0.0387(3) Uani 1 1 d . . . C7 C 0.31650(10) 0.09399(8) 0.16185(9) 0.0382(3) Uani 1 1 d . . . C8 C 0.37901(8) 0.18456(7) 0.21623(9) 0.0335(3) Uani 1 1 d . . . C9 C 0.36528(9) 0.18185(7) 0.33457(9) 0.0340(3) Uani 1 1 d . . . C10 C 0.45307(9) 0.14990(8) 0.42498(10) 0.0419(3) Uani 1 1 d . . . H10A H 0.5245 0.1336 0.4149 0.050 Uiso 1 1 calc R . . C11 C 0.43538(11) 0.14202(8) 0.52964(10) 0.0499(3) Uani 1 1 d . . . H11A H 0.4950 0.1207 0.5896 0.060 Uiso 1 1 calc R . . C12 C 0.33094(11) 0.16539(8) 0.54572(11) 0.0513(3) Uani 1 1 d . . . H12A H 0.3200 0.1618 0.6168 0.062 Uiso 1 1 calc R . . C13 C 0.24251(10) 0.19407(9) 0.45648(11) 0.0502(3) Uani 1 1 d . . . H13A H 0.1708 0.2086 0.4670 0.060 Uiso 1 1 calc R . . C14 C 0.25822(9) 0.20168(8) 0.35127(10) 0.0425(3) Uani 1 1 d . . . H14A H 0.1969 0.2202 0.2912 0.051 Uiso 1 1 calc R . . C15 C 0.33105(8) 0.26829(7) 0.14332(9) 0.0340(3) Uani 1 1 d . . . C16 C 0.29782(9) 0.35020(8) 0.18326(10) 0.0416(3) Uani 1 1 d . . . H16A H 0.2989 0.3550 0.2581 0.050 Uiso 1 1 calc R . . C17 C 0.26287(9) 0.42529(9) 0.11204(12) 0.0515(3) Uani 1 1 d . . . H17A H 0.2404 0.4800 0.1395 0.062 Uiso 1 1 calc R . . C18 C 0.26121(10) 0.41928(10) 0.00161(12) 0.0551(4) Uani 1 1 d . . . H18A H 0.2386 0.4700 -0.0455 0.066 Uiso 1 1 calc R . . C19 C 0.29313(10) 0.33788(10) -0.03953(11) 0.0519(3) Uani 1 1 d . . . H19A H 0.2918 0.3334 -0.1145 0.062 Uiso 1 1 calc R . . C20 C 0.32694(9) 0.26320(8) 0.03096(10) 0.0425(3) Uani 1 1 d . . . H20A H 0.3475 0.2082 0.0026 0.051 Uiso 1 1 calc R . . C21 C 0.58329(9) 0.23115(8) 0.20962(9) 0.0388(3) Uani 1 1 d . . . C22 C 0.56950(8) 0.32869(8) 0.24326(10) 0.0374(3) Uani 1 1 d . . . C23 C 0.56953(9) 0.35292(8) 0.35110(10) 0.0426(3) Uani 1 1 d . . . H23A H 0.5719 0.3070 0.4042 0.051 Uiso 1 1 calc R . . C24 C 0.56604(9) 0.44507(9) 0.38002(11) 0.0468(3) Uani 1 1 d . . . H24A H 0.5681 0.4619 0.4528 0.056 Uiso 1 1 calc R . . C25 C 0.55944(9) 0.51109(8) 0.29943(11) 0.0450(3) Uani 1 1 d . . . C26 C 0.55989(9) 0.48956(9) 0.19222(11) 0.0490(3) Uani 1 1 d . . . H26A H 0.5551 0.5359 0.1391 0.059 Uiso 1 1 calc R . . C27 C 0.56758(9) 0.39784(9) 0.16479(10) 0.0454(3) Uani 1 1 d . . . H27A H 0.5715 0.3820 0.0934 0.054 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 O1 0.0386(5) 0.0591(6) 0.0633(6) -0.0087(4) 0.0105(4) -0.0081(4) O2 0.0554(6) 0.0601(6) 0.0895(8) -0.0029(5) 0.0472(5) -0.0013(4) O3 0.1274(9) 0.0592(8) 0.1002(10) -0.0282(7) 0.0455(8) -0.0185(6) O4 0.1005(8) 0.0470(7) 0.1125(10) 0.0114(7) 0.0194(7) -0.0002(5) N1 0.0326(5) 0.0345(6) 0.0373(6) -0.0027(4) 0.0139(4) 0.0014(4) N2 0.0589(7) 0.0445(8) 0.0865(11) -0.0058(8) 0.0187(7) -0.0097(5) C1 0.0433(7) 0.0354(7) 0.0311(7) 0.0003(5) 0.0137(5) 0.0047(5) C2 0.0478(7) 0.0489(8) 0.0460(8) -0.0054(6) 0.0147(6) 0.0095(6) C3 0.0661(9) 0.0535(9) 0.0579(9) -0.0051(7) 0.0221(7) 0.0194(7) C4 0.0804(10) 0.0388(8) 0.0706(10) -0.0107(7) 0.0293(8) 0.0053(7) C5 0.0624(8) 0.0442(8) 0.0544(9) -0.0061(6) 0.0224(6) -0.0075(6) C6 0.0466(7) 0.0356(7) 0.0363(7) -0.0009(5) 0.0158(5) -0.0003(5) C7 0.0399(7) 0.0421(7) 0.0337(7) 0.0004(5) 0.0120(5) -0.0042(5) C8 0.0297(6) 0.0368(7) 0.0354(7) -0.0011(5) 0.0113(5) 0.0010(5) C9 0.0358(6) 0.0333(7) 0.0351(7) -0.0008(5) 0.0132(5) -0.0013(5) C10 0.0402(6) 0.0444(8) 0.0411(8) 0.0017(6) 0.0114(5) 0.0014(5) C11 0.0566(8) 0.0547(9) 0.0362(8) 0.0049(6) 0.0095(6) -0.0009(6) C12 0.0710(9) 0.0489(8) 0.0412(8) 0.0012(6) 0.0276(7) -0.0018(6) C13 0.0539(8) 0.0505(8) 0.0559(9) 0.0044(7) 0.0317(7) 0.0049(6) C14 0.0405(7) 0.0459(8) 0.0444(8) 0.0052(6) 0.0175(5) 0.0040(5) C15 0.0300(6) 0.0389(7) 0.0341(7) -0.0003(5) 0.0102(5) -0.0008(5) C16 0.0421(7) 0.0422(8) 0.0447(8) -0.0002(6) 0.0187(5) 0.0038(5) C17 0.0494(8) 0.0407(8) 0.0673(10) 0.0049(7) 0.0209(7) 0.0084(6) C18 0.0527(8) 0.0516(9) 0.0573(10) 0.0181(7) 0.0090(6) 0.0032(6) C19 0.0546(8) 0.0595(9) 0.0376(8) 0.0072(7) 0.0064(6) -0.0079(6) C20 0.0455(7) 0.0426(8) 0.0390(8) -0.0030(6) 0.0113(5) -0.0016(5) C21 0.0368(7) 0.0450(8) 0.0374(7) 0.0015(5) 0.0149(5) -0.0001(5) C22 0.0307(6) 0.0402(7) 0.0418(8) -0.0017(6) 0.0109(5) -0.0053(5) C23 0.0427(7) 0.0431(8) 0.0415(8) 0.0018(6) 0.0108(5) -0.0027(5) C24 0.0463(7) 0.0491(8) 0.0440(8) -0.0076(7) 0.0113(5) -0.0050(6) C25 0.0389(7) 0.0374(8) 0.0580(9) -0.0060(7) 0.0121(6) -0.0072(5) C26 0.0456(7) 0.0446(9) 0.0564(9) 0.0089(7) 0.0136(6) -0.0086(5) C27 0.0435(7) 0.0511(9) 0.0441(8) 0.0010(6) 0.0164(5) -0.0084(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 O1 C7 1.2082(12) . ? O2 C21 1.2142(12) . ? O3 N2 1.2228(15) . ? O4 N2 1.2219(15) . ? N1 C21 1.3778(13) . ? N1 C1 1.4157(13) . ? N1 C8 1.5024(12) . ? N2 C25 1.4777(16) . ? C1 C6 1.3883(14) . ? C1 C2 1.3886(14) . ? C2 C3 1.3751(17) . ? C2 H2A 0.9300 . ? C3 C4 1.3784(17) . ? C3 H3A 0.9300 . ? C4 C5 1.3719(17) . ? C4 H4A 0.9300 . ? C5 C6 1.3843(16) . ? C5 H5A 0.9300 . ? C6 C7 1.4546(15) . ? C7 C8 1.5643(15) . ? C8 C9 1.5260(15) . ? C8 C15 1.5244(14) . ? C9 C14 1.3876(14) . ? C9 C10 1.3881(14) . ? C10 C11 1.3802(16) . ? C10 H10A 0.9300 . ? C11 C12 1.3658(16) . ? C11 H11A 0.9300 . ? C12 C13 1.3686(17) . ? C12 H12A 0.9300 . ? C13 C14 1.3771(16) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C20 1.3859(15) . ? C15 C16 1.3836(15) . ? C16 C17 1.3886(16) . ? C16 H16A 0.9300 . ? C17 C18 1.3703(17) . ? C17 H17A 0.9300 . ? C18 C19 1.3779(18) . ? C18 H18A 0.9300 . ? C19 C20 1.3773(16) . ? C19 H19A 0.9300 . ? C20 H20A 0.9300 . ? C21 C22 1.4912(16) . ? C22 C23 1.3855(15) . ? C22 C27 1.3916(16) . ? C23 C24 1.3817(16) . ? C23 H23A 0.9300 . ? C24 C25 1.3691(17) . ? C24 H24A 0.9300 . ? C25 C26 1.3702(16) . ? C26 C27 1.3768(16) . ? C26 H26A 0.9300 . ? C27 H27A 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 C21 N1 C1 121.78(9) . . ? C21 N1 C8 125.93(9) . . ? C1 N1 C8 109.87(8) . . ? O4 N2 O3 124.75(14) . . ? O4 N2 C25 117.57(14) . . ? O3 N2 C25 117.68(13) . . ? C6 C1 C2 120.09(11) . . ? C6 C1 N1 111.14(9) . . ? C2 C1 N1 128.76(10) . . ? C3 C2 C1 117.35(11) . . ? C3 C2 H2A 121.3 . . ? C1 C2 H2A 121.3 . . ? C2 C3 C4 122.69(12) . . ? C2 C3 H3A 118.7 . . ? C4 C3 H3A 118.7 . . ? C5 C4 C3 120.13(13) . . ? C5 C4 H4A 119.9 . . ? C3 C4 H4A 119.9 . . ? C4 C5 C6 118.12(12) . . ? C4 C5 H5A 120.9 . . ? C6 C5 H5A 120.9 . . ? C1 C6 C5 121.60(10) . . ? C1 C6 C7 108.96(10) . . ? C5 C6 C7 129.44(10) . . ? O1 C7 C6 128.77(11) . . ? O1 C7 C8 123.64(10) . . ? C6 C7 C8 107.50(9) . . ? N1 C8 C9 112.01(8) . . ? N1 C8 C15 110.36(8) . . ? C9 C8 C15 117.99(9) . . ? N1 C8 C7 101.31(8) . . ? C9 C8 C7 103.16(8) . . ? C15 C8 C7 110.46(8) . . ? C14 C9 C10 118.25(10) . . ? C14 C9 C8 119.49(9) . . ? C10 C9 C8 121.85(9) . . ? C11 C10 C9 120.62(11) . . ? C11 C10 H10A 119.7 . . ? C9 C10 H10A 119.7 . . ? C12 C11 C10 120.42(11) . . ? C12 C11 H11A 119.8 . . ? C10 C11 H11A 119.8 . . ? C11 C12 C13 119.50(12) . . ? C11 C12 H12A 120.3 . . ? C13 C12 H12A 120.3 . . ? C14 C13 C12 120.91(11) . . ? C14 C13 H13A 119.5 . . ? C12 C13 H13A 119.5 . . ? C13 C14 C9 120.22(11) . . ? C13 C14 H14A 119.9 . . ? C9 C14 H14A 119.9 . . ? C20 C15 C16 118.31(11) . . ? C20 C15 C8 117.31(10) . . ? C16 C15 C8 124.27(10) . . ? C15 C16 C17 120.29(11) . . ? C15 C16 H16A 119.9 . . ? C17 C16 H16A 119.9 . . ? C16 C17 C18 120.46(12) . . ? C16 C17 H17A 119.8 . . ? C18 C17 H17A 119.8 . . ? C19 C18 C17 119.87(12) . . ? C19 C18 H18A 120.1 . . ? C17 C18 H18A 120.1 . . ? C18 C19 C20 119.64(12) . . ? C18 C19 H19A 120.2 . . ? C20 C19 H19A 120.2 . . ? C19 C20 C15 121.42(12) . . ? C19 C20 H20A 119.3 . . ? C15 C20 H20A 119.3 . . ? O2 C21 N1 121.12(11) . . ? O2 C21 C22 118.88(10) . . ? N1 C21 C22 119.99(9) . . ? C23 C22 C27 119.53(11) . . ? C23 C22 C21 122.66(11) . . ? C27 C22 C21 117.53(11) . . ? C24 C23 C22 120.20(12) . . ? C24 C23 H23A 119.9 . . ? C22 C23 H23A 119.9 . . ? C25 C24 C23 118.65(12) . . ? C25 C24 H24A 120.7 . . ? C23 C24 H24A 120.7 . . ? C24 C25 C26 122.61(11) . . ? C24 C25 N2 118.49(13) . . ? C26 C25 N2 118.90(12) . . ? C27 C26 C25 118.54(12) . . ? C27 C26 H26A 120.7 . . ? C25 C26 H26A 120.7 . . ? C26 C27 C22 120.36(12) . . ? C26 C27 H27A 119.8 . . ? C22 C27 H27A 119.8 . . ? _diffrn_measured_fraction_theta_max 0.867 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.154 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.031 _database_code_depnum_ccdc_archive 'CCDC 951677'