# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_requested_category FO _publ_contact_author_email Daniel.Fortin@usherbrooke.ca _publ_contact_author_name 'Daniel Fortin' loop_ _publ_author_name 'Simon Lamare' 'Shawkat M. Aly' 'Daniel Fortin' 'Pierre D. Harvey' data_tfqdidiodo _database_code_depnum_ccdc_archive 'CCDC 832795' #TrackingRef '2a.cif' _audit_creation_date 2010-03-23T14:33:27-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C18 H8 F4 I2 N2' _chemical_formula_weight 582.06 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 5.887(2) _cell_length_b 7.940(2) _cell_length_c 36.911(11) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1725.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 10 _cell_measurement_theta_max 12.5 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description Plate _exptl_crystal_colour Pink _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 2.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.69 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_process_details Empirical _exptl_absorpt_correction_T_min 0.3583 _exptl_absorpt_correction_T_max 0.8973 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CAD4 _diffrn_measurement_method Omega _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% 0 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.0923 _diffrn_reflns_number 1589 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 25.55 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.972 _diffrn_measured_fraction_theta_max 0.972 _reflns_number_total 1589 _reflns_number_gt 768 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection Difrac _computing_cell_refinement Difrac _computing_data_reduction NRCVAX _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0760P)^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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0009(2) _refine_ls_number_reflns 1589 _refine_ls_number_parameters 69 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1687 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1492 _refine_ls_wR_factor_gt 0.1179 _refine_ls_goodness_of_fit_ref 0.886 _refine_ls_restrained_S_all 0.887 _refine_ls_shift/su_max 0.092 _refine_ls_shift/su_mean 0.007 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(5) _refine_diff_density_max 1.726 _refine_diff_density_min -1.267 _refine_diff_density_rms 0.222 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.036(4) 1.002(3) 0.8508(7) 0.0284(10) Uani 1 1 d G . . C2 C -0.181(4) 1.070(3) 0.8487(8) 0.0284(10) Uani 1 1 d G . . H2 H -0.2471 1.121 0.8694 0.034 Uiso 1 1 calc R . . C3 C -0.301(3) 1.063(3) 0.8163(9) 0.0284(10) Uani 1 1 d G . . H3 H -0.4492 1.1096 0.8149 0.034 Uiso 1 1 calc R . . C4 C -0.204(4) 0.988(3) 0.7860(7) 0.0284(10) Uani 1 1 d G . . C5 C 0.013(4) 0.920(3) 0.7881(7) 0.0284(10) Uani 1 1 d G . . H5 H 0.0797 0.8688 0.7674 0.034 Uiso 1 1 calc R . . C6 C 0.133(3) 0.927(2) 0.8205(8) 0.0284(10) Uani 1 1 d G . . H6 H 0.2818 0.8801 0.8219 0.034 Uiso 1 1 calc R . . C7 C -0.284(4) 1.000(3) 0.5809(7) 0.0284(10) Uani 1 1 d G . . C8 C -0.487(3) 1.088(3) 0.5805(7) 0.0284(10) Uani 1 1 d G . . H8 H -0.5403 1.1418 0.6019 0.034 Uiso 1 1 calc R . . C9 C -0.614(3) 1.098(2) 0.5487(8) 0.0284(10) Uani 1 1 d G . . H9 H -0.7529 1.159 0.5484 0.034 Uiso 1 1 calc R . . C10 C -0.536(4) 1.020(3) 0.5174(7) 0.0284(10) Uani 1 1 d G . . C11 C -0.333(4) 0.932(3) 0.5178(8) 0.0284(10) Uani 1 1 d G . . H11 H -0.2797 0.878 0.4964 0.034 Uiso 1 1 calc R . . C12 C -0.206(3) 0.921(3) 0.5495(8) 0.0284(10) Uani 1 1 d G . . H12 H -0.0671 0.8609 0.5498 0.034 Uiso 1 1 calc R . . C13 C -0.206(5) 1.001(3) 0.6465(10) 0.0284(10) Uani 1 1 d GD . . C14 C -0.045(5) 1.064(3) 0.6706(10) 0.0284(10) Uani 1 1 d G . . C15 C -0.088(5) 1.060(3) 0.7077(10) 0.0284(10) Uani 1 1 d G . . C16 C -0.290(5) 0.993(3) 0.7206(10) 0.0284(10) Uani 1 1 d GD . . C17 C -0.451(5) 0.930(3) 0.6965(10) 0.0284(10) Uani 1 1 d G . . C18 C -0.409(5) 0.934(3) 0.6595(10) 0.0284(10) Uani 1 1 d G . . F1 F 0.135(4) 1.139(2) 0.6623(7) 0.0306(12) Uani 1 1 d D . . F2 F 0.065(4) 1.143(2) 0.7283(8) 0.0306(12) Uani 1 1 d D . . F3 F -0.649(4) 0.859(2) 0.7101(7) 0.0306(12) Uani 1 1 d D . . F4 F -0.552(4) 0.863(2) 0.6367(8) 0.0306(12) Uani 1 1 d D . . I1 I -0.7204(6) 1.0209(5) 0.46827(3) 0.0488(11) Uani 1 1 d . . . I2 I 0.2248(6) 0.9783(4) 0.89749(4) 0.0434(11) Uani 1 1 d . . . N1 N -0.353(7) 0.979(5) 0.7554(10) 0.0306(12) Uani 1 1 d D . . N2 N -0.140(7) 1.023(5) 0.6121(10) 0.0306(12) Uani 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C2 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C3 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C4 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C5 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C6 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C7 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C8 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C9 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C10 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C11 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C12 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C13 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C14 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C15 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C16 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C17 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) C18 0.022(2) 0.028(2) 0.035(2) -0.0008(17) 0.0006(18) -0.0032(18) F1 0.025(2) 0.033(2) 0.034(3) 0.002(2) -0.002(2) -0.0070(19) F2 0.025(2) 0.033(2) 0.034(3) 0.002(2) -0.002(2) -0.0070(19) F3 0.025(2) 0.033(2) 0.034(3) 0.002(2) -0.002(2) -0.0070(19) F4 0.025(2) 0.033(2) 0.034(3) 0.002(2) -0.002(2) -0.0070(19) I1 0.042(2) 0.077(2) 0.027(2) 0.0110(17) -0.002(3) -0.007(2) I2 0.051(2) 0.0533(16) 0.026(2) -0.0058(17) -0.003(3) -0.001(2) N1 0.025(2) 0.033(2) 0.034(3) 0.002(2) -0.002(2) -0.0070(19) N2 0.025(2) 0.033(2) 0.034(3) 0.002(2) -0.002(2) -0.0070(19) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.39 . ? C1 C6 1.39 . ? C1 I2 2.06(2) . ? C2 C3 1.39 . ? C3 C4 1.39 . ? C4 C5 1.39 . ? C4 N1 1.43(4) . ? C5 C6 1.39 . ? C7 C8 1.39 . ? C7 C12 1.39 . ? C7 N2 1.44(4) . ? C8 C9 1.39 . ? C9 C10 1.39 . ? C10 C11 1.39 . ? C10 I1 2.11(2) . ? C11 C12 1.39 . ? C13 N2 1.338(16) . ? C13 C14 1.39 . ? C13 C18 1.39 . ? C14 F1 1.26(4) . ? C14 C15 1.39 . ? C15 F2 1.35(3) . ? C15 C16 1.39 . ? C16 N1 1.340(16) . ? C16 C17 1.39 . ? C17 F3 1.39(4) . ? C17 C18 1.39 . ? C18 F4 1.32(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120 . . ? C2 C1 I2 125.2(13) . . ? C6 C1 I2 114.5(12) . . ? C3 C2 C1 120 . . ? C4 C3 C2 120 . . ? C3 C4 C5 120 . . ? C3 C4 N1 114(2) . . ? C5 C4 N1 126(2) . . ? C6 C5 C4 120 . . ? C5 C6 C1 120 . . ? C8 C7 C12 120 . . ? C8 C7 N2 117(2) . . ? C12 C7 N2 122(2) . . ? C9 C8 C7 120 . . ? C10 C9 C8 120 . . ? C9 C10 C11 120 . . ? C9 C10 I1 123.0(12) . . ? C11 C10 I1 117.0(12) . . ? C12 C11 C10 120 . . ? C11 C12 C7 120 . . ? N2 C13 C14 111(2) . . ? N2 C13 C18 129(2) . . ? C14 C13 C18 120 . . ? F1 C14 C15 113.7(16) . . ? F1 C14 C13 126.0(17) . . ? C15 C14 C13 120.00(9) . . ? F2 C15 C14 115.1(15) . . ? F2 C15 C16 124.3(15) . . ? C14 C15 C16 120.00(8) . . ? N1 C16 C15 127(2) . . ? N1 C16 C17 113(2) . . ? C15 C16 C17 120 . . ? F3 C17 C18 121.0(16) . . ? F3 C17 C16 119.0(17) . . ? C18 C17 C16 120.00(9) . . ? F4 C18 C17 120.1(16) . . ? F4 C18 C13 119.7(16) . . ? C17 C18 C13 120.00(8) . . ? C16 N1 C4 126(3) . . ? C13 N2 C7 125(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0 . . . . ? I2 C1 C2 C3 -173.3(16) . . . . ? C1 C2 C3 C4 0 . . . . ? C2 C3 C4 C5 0 . . . . ? C2 C3 C4 N1 176(3) . . . . ? C3 C4 C5 C6 0 . . . . ? N1 C4 C5 C6 -175(3) . . . . ? C4 C5 C6 C1 0 . . . . ? C2 C1 C6 C5 0 . . . . ? I2 C1 C6 C5 174.0(15) . . . . ? C12 C7 C8 C9 0 . . . . ? N2 C7 C8 C9 168(3) . . . . ? C7 C8 C9 C10 0 . . . . ? C8 C9 C10 C11 0 . . . . ? C8 C9 C10 I1 177.9(16) . . . . ? C9 C10 C11 C12 0 . . . . ? I1 C10 C11 C12 -178.0(15) . . . . ? C10 C11 C12 C7 0 . . . . ? C8 C7 C12 C11 0 . . . . ? N2 C7 C12 C11 -167(3) . . . . ? N2 C13 C14 F1 3(2) . . . . ? C18 C13 C14 F1 -173.8(19) . . . . ? N2 C13 C14 C15 177(3) . . . . ? C18 C13 C14 C15 0 . . . . ? F1 C14 C15 F2 2.7(8) . . . . ? C13 C14 C15 F2 -171.8(16) . . . . ? F1 C14 C15 C16 174.5(17) . . . . ? C13 C14 C15 C16 0 . . . . ? F2 C15 C16 N1 -10(3) . . . . ? C14 C15 C16 N1 179(3) . . . . ? F2 C15 C16 C17 171.0(18) . . . . ? C14 C15 C16 C17 0 . . . . ? N1 C16 C17 F3 -1(2) . . . . ? C15 C16 C17 F3 178.0(16) . . . . ? N1 C16 C17 C18 -179(3) . . . . ? C15 C16 C17 C18 0 . . . . ? F3 C17 C18 F4 -3.4(9) . . . . ? C16 C17 C18 F4 174.5(17) . . . . ? F3 C17 C18 C13 -177.9(16) . . . . ? C16 C17 C18 C13 0 . . . . ? N2 C13 C18 F4 9(3) . . . . ? C14 C13 C18 F4 -174.6(17) . . . . ? N2 C13 C18 C17 -176(3) . . . . ? C14 C13 C18 C17 0 . . . . ? C15 C16 N1 C4 -17(6) . . . . ? C17 C16 N1 C4 162(3) . . . . ? C3 C4 N1 C16 146(3) . . . . ? C5 C4 N1 C16 -39(6) . . . . ? C14 C13 N2 C7 -168(3) . . . . ? C18 C13 N2 C7 8(6) . . . . ? C8 C7 N2 C13 54(5) . . . . ? C12 C7 N2 C13 -139(3) . . . . ? # Attachment '5a.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2010-07-12 at 10:58:08 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : qf4i2nh2 data_qf4i2nh2 _database_code_depnum_ccdc_archive 'CCDC 832796' #TrackingRef '5a.cif' _audit_creation_date 2010-07-12T10:58:08-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C18 H10 F4 I2 N2' _chemical_formula_weight 584.08 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnaa loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x, y-1/2, z-1/2' 'x-1/2, -y-1/2, z' _cell_length_a 5.793(2) _cell_length_b 8.312(5) _cell_length_c 36.680(13) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1766.0(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 30 _cell_measurement_theta_max 35 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 2.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.606 _exptl_absorpt_correction_type Psi-Scan _exptl_absorpt_process_details Empirical _exptl_absorpt_correction_T_min 0.2417 _exptl_absorpt_correction_T_max 0.6138 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CAD4 _diffrn_measurement_method Omega _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% 0 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.0476 _diffrn_reflns_number 1654 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 1.11 _diffrn_reflns_theta_max 25.56 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 1654 _reflns_number_gt 876 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection Difrac _computing_cell_refinement Difrac _computing_data_reduction NRCVAX _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0636P)^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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0016(3) _refine_ls_number_reflns 1654 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1149 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.133 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_restrained_S_all 1.02 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.748 _refine_diff_density_min -0.614 _refine_diff_density_rms 0.146 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1978(16) 0.9799(10) 0.3334(2) 0.048(2) Uani 1 1 d . . . C2 C 0.1271(15) 0.9087(10) 0.36546(18) 0.044(2) Uani 1 1 d . . . H2 H -0.0113 0.8522 0.3664 0.053 Uiso 1 1 calc R . . C3 C 0.2647(13) 0.9224(9) 0.3962(2) 0.040(2) Uani 1 1 d . . . H3 H 0.2195 0.8722 0.4177 0.048 Uiso 1 1 calc R . . C4 C 0.4663(13) 1.0087(9) 0.3955(2) 0.0348(19) Uani 1 1 d . . . C5 C 0.5311(15) 1.0805(10) 0.3630(2) 0.047(2) Uani 1 1 d . . . H5 H 0.6671 1.1399 0.362 0.057 Uiso 1 1 calc R . . C6 C 0.3977(15) 1.0656(10) 0.3322(2) 0.049(2) Uani 1 1 d . . . H6 H 0.4441 1.114 0.3105 0.058 Uiso 1 1 calc R . . C7 C 0.5488(13) 1.0084(9) 0.4618(2) 0.036(2) Uani 1 1 d . . . C8 C 0.6962(13) 0.9391(9) 0.4870(2) 0.0374(19) Uani 1 1 d . . . C9 C 0.3488(14) 1.0706(9) 0.47711(19) 0.035(2) Uani 1 1 d . . . F1 F 0.8946(8) 0.8706(6) 0.47458(11) 0.0505(12) Uani 1 1 d . . . F2 F 0.1997(8) 1.1496(6) 0.45486(11) 0.0545(13) Uani 1 1 d . . . I1 I -0.00840(12) 0.95870(10) 0.286519(14) 0.0682(3) Uani 1 1 d . . . N1 N 0.6135(12) 1.0212(8) 0.42554(17) 0.0448(18) Uani 1 1 d . . . H1 H 0.7572 1.0385 0.4211 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 C1 0.048(6) 0.059(6) 0.038(4) -0.004(4) -0.005(4) 0.011(5) C2 0.036(5) 0.060(6) 0.035(4) -0.003(4) 0.004(4) -0.007(5) C3 0.043(5) 0.044(5) 0.034(4) -0.001(4) 0.005(4) -0.005(4) C4 0.035(5) 0.029(4) 0.040(4) -0.003(3) 0.005(4) -0.001(4) C5 0.039(5) 0.059(6) 0.043(4) 0.006(4) 0.003(4) -0.011(5) C6 0.045(5) 0.073(7) 0.028(4) 0.006(4) 0.005(4) -0.001(5) C7 0.032(5) 0.036(5) 0.040(4) 0.001(3) -0.003(4) 0.005(4) C8 0.034(5) 0.038(5) 0.039(4) -0.008(4) 0.002(4) 0.013(4) C9 0.034(5) 0.033(5) 0.039(4) -0.005(4) 0.000(4) 0.004(4) F1 0.036(3) 0.065(3) 0.050(3) -0.007(3) 0.002(2) 0.010(3) F2 0.054(3) 0.059(3) 0.051(3) 0.000(3) -0.010(2) 0.021(3) I1 0.0508(4) 0.1167(7) 0.0371(3) -0.0090(3) -0.0044(3) 0.0053(5) N1 0.032(4) 0.069(5) 0.034(4) -0.005(3) 0.004(3) -0.005(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.360(12) . ? C1 C2 1.378(11) . ? C1 I1 2.101(9) . ? C2 C3 1.387(10) . ? C3 C4 1.371(10) . ? C4 C5 1.385(11) . ? C4 N1 1.397(10) . ? C5 C6 1.375(11) . ? C7 C8 1.385(10) . ? C7 N1 1.386(10) . ? C7 C9 1.388(10) . ? C8 C9 1.344(10) 5_676 ? C8 F1 1.361(8) . ? C9 C8 1.344(10) 5_676 ? C9 F2 1.358(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.4(8) . . ? C6 C1 I1 120.1(6) . . ? C2 C1 I1 119.5(7) . . ? C1 C2 C3 119.2(8) . . ? C4 C3 C2 121.1(7) . . ? C3 C4 C5 118.3(8) . . ? C3 C4 N1 122.9(7) . . ? C5 C4 N1 118.8(7) . . ? C6 C5 C4 121.1(8) . . ? C1 C6 C5 119.9(8) . . ? C8 C7 N1 120.4(7) . . ? C8 C7 C9 113.5(7) . . ? N1 C7 C9 125.9(7) . . ? C9 C8 F1 117.8(7) 5_676 . ? C9 C8 C7 124.0(7) 5_676 . ? F1 C8 C7 118.1(7) . . ? C8 C9 F2 119.6(7) 5_676 . ? C8 C9 C7 122.4(7) 5_676 . ? F2 C9 C7 117.9(6) . . ? C7 N1 C4 125.9(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.4(13) . . . . ? I1 C1 C2 C3 179.6(6) . . . . ? C1 C2 C3 C4 1.6(12) . . . . ? C2 C3 C4 C5 -0.8(12) . . . . ? C2 C3 C4 N1 -177.9(7) . . . . ? C3 C4 C5 C6 -0.2(12) . . . . ? N1 C4 C5 C6 177.0(7) . . . . ? C2 C1 C6 C5 0.4(13) . . . . ? I1 C1 C6 C5 179.4(6) . . . . ? C4 C5 C6 C1 0.4(13) . . . . ? N1 C7 C8 C9 176.5(7) . . . 5_676 ? C9 C7 C8 C9 1.1(13) . . . 5_676 ? N1 C7 C8 F1 -6.2(12) . . . . ? C9 C7 C8 F1 178.3(6) . . . . ? C8 C7 C9 C8 -1.0(13) . . . 5_676 ? N1 C7 C9 C8 -176.2(7) . . . 5_676 ? C8 C7 C9 F2 176.1(7) . . . . ? N1 C7 C9 F2 0.9(12) . . . . ? C8 C7 N1 C4 145.5(8) . . . . ? C9 C7 N1 C4 -39.6(12) . . . . ? C3 C4 N1 C7 -26.6(12) . . . . ? C5 C4 N1 C7 156.3(8) . . . . ? # Attachment '5b.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-06-20 at 11:49:29 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : tmdai2 data_tmdai2 _database_code_depnum_ccdc_archive 'CCDC 832797' #TrackingRef '5b.cif' _audit_creation_date 2011-06-20T11:49:29-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C22 H22 I2 N2' _chemical_formula_weight 568.22 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.632(2) _cell_length_b 10.136(5) _cell_length_c 13.097(6) _cell_angle_alpha 72.46(4) _cell_angle_beta 78.12(3) _cell_angle_gamma 79.22(4) _cell_volume 1059.5(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 10 _cell_measurement_theta_max 12.5 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.781 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.976 _exptl_absorpt_correction_type Psi-Scan _exptl_absorpt_process_details Empirical _exptl_absorpt_correction_T_min 0.3823 _exptl_absorpt_correction_T_max 0.5875 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CAD4 _diffrn_measurement_method Omega _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% 0 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.0489 _diffrn_reflns_number 3953 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.54 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 3953 _reflns_number_gt 2360 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection difrac _computing_cell_refinement difrac _computing_data_reduction nrcvax _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0934P)^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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0026(10) _refine_ls_number_reflns 3953 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1141 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1639 _refine_ls_wR_factor_gt 0.1439 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.048 _refine_diff_density_min -1.108 _refine_diff_density_rms 0.153 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C21 C 0.7258(12) 0.0403(12) 0.3948(9) 0.083(3) Uani 1 1 d . . . H21A H 0.7518 -0.0105 0.341 0.125 Uiso 1 1 calc R . . H21B H 0.6983 0.1377 0.3605 0.125 Uiso 1 1 calc R . . H21C H 0.6367 0.0059 0.4472 0.125 Uiso 1 1 calc R . . C1 C 0.4196(10) 0.5815(8) 0.8536(7) 0.051(2) Uani 1 1 d . . . C2 C 0.4678(11) 0.7143(9) 0.8243(8) 0.061(2) Uani 1 1 d . . . H2 H 0.4145 0.7809 0.8595 0.073 Uiso 1 1 calc R . . C3 C 0.5939(11) 0.7439(8) 0.7436(7) 0.056(2) Uani 1 1 d . . . H3 H 0.6254 0.8322 0.7238 0.068 Uiso 1 1 calc R . . C4 C 0.6757(9) 0.6483(8) 0.6906(6) 0.0479(19) Uani 1 1 d . . . C5 C 0.6266(11) 0.5170(9) 0.7209(7) 0.061(2) Uani 1 1 d . . . H5 H 0.6809 0.4504 0.686 0.073 Uiso 1 1 calc R . . C6 C 0.4997(11) 0.4844(9) 0.8013(8) 0.064(2) Uani 1 1 d . . . H6 H 0.4679 0.3963 0.8204 0.077 Uiso 1 1 calc R . . C7 C 0.9012(10) 0.5899(8) 0.5539(6) 0.048(2) Uani 1 1 d . . . C8 C 0.8499(10) 0.5601(8) 0.4681(7) 0.053(2) Uani 1 1 d . . . C9 C 1.0475(10) 0.5298(8) 0.5855(6) 0.0488(19) Uani 1 1 d . . . C10 C 0.6893(11) 0.6241(11) 0.4384(8) 0.074(3) Uani 1 1 d . . . H10A H 0.6735 0.5945 0.3787 0.111 Uiso 1 1 calc R . . H10B H 0.683 0.724 0.4179 0.111 Uiso 1 1 calc R . . H10C H 0.6082 0.5949 0.4995 0.111 Uiso 1 1 calc R . . C11 C 1.0913(12) 0.5583(11) 0.6824(8) 0.076(3) Uani 1 1 d . . . H11A H 1.1957 0.5101 0.6942 0.114 Uiso 1 1 calc R . . H11B H 1.0147 0.5261 0.7455 0.114 Uiso 1 1 calc R . . H11C H 1.0915 0.6568 0.6687 0.114 Uiso 1 1 calc R . . C12 C 1.2262(11) 0.0318(9) 0.0175(7) 0.055(2) Uani 1 1 d . . . C13 C 1.1915(14) 0.1146(10) 0.0862(7) 0.077(3) Uani 1 1 d . . . H13 H 1.2164 0.2054 0.0624 0.092 Uiso 1 1 calc R . . C14 C 1.1179(13) 0.0616(9) 0.1930(7) 0.070(3) Uani 1 1 d . . . H14 H 1.0934 0.1184 0.2397 0.085 Uiso 1 1 calc R . . C15 C 1.0811(10) -0.0729(8) 0.2304(6) 0.050(2) Uani 1 1 d . . . C16 C 1.1152(12) -0.1519(8) 0.1572(7) 0.066(3) Uani 1 1 d . . . H16 H 1.0896 -0.2425 0.1797 0.079 Uiso 1 1 calc R . . C17 C 1.1854(12) -0.1005(9) 0.0530(7) 0.067(3) Uani 1 1 d . . . H17 H 1.2059 -0.1559 0.0054 0.08 Uiso 1 1 calc R . . C18 C 1.0063(10) -0.0635(8) 0.4195(6) 0.0459(19) Uani 1 1 d . . . C19 C 0.8655(10) 0.0212(9) 0.4499(7) 0.052(2) Uani 1 1 d . . . C20 C 0.8602(9) 0.0827(8) 0.5321(7) 0.050(2) Uani 1 1 d . . . C22 C 0.7110(10) 0.1718(10) 0.5693(8) 0.075(3) Uani 1 1 d . . . H22A H 0.6294 0.1758 0.5281 0.112 Uiso 1 1 calc R . . H22B H 0.7344 0.2644 0.5586 0.112 Uiso 1 1 calc R . . H22C H 0.6744 0.1317 0.6449 0.112 Uiso 1 1 calc R . . I1 I 0.21754(8) 0.53624(7) 0.97168(5) 0.0697(3) Uani 1 1 d . . . I2 I 1.34467(10) 0.10663(7) -0.13926(5) 0.0849(3) Uani 1 1 d . . . N1 N 0.7998(8) 0.6840(7) 0.6068(6) 0.062(2) Uani 1 1 d . . . H1 H 0.8166 0.7698 0.5853 0.074 Uiso 1 1 calc R . . N2 N 1.0115(9) -0.1284(7) 0.3365(5) 0.062(2) Uani 1 1 d . . . H2A H 0.9702 -0.2044 0.3525 0.075 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 C21 0.064(7) 0.106(9) 0.092(8) -0.036(7) -0.034(6) -0.003(6) C1 0.046(5) 0.045(5) 0.058(5) -0.007(4) 0.002(4) -0.015(4) C2 0.061(6) 0.043(5) 0.078(6) -0.021(4) 0.001(5) -0.012(4) C3 0.069(6) 0.040(4) 0.058(5) -0.012(4) 0.009(4) -0.025(4) C4 0.046(5) 0.045(4) 0.050(4) -0.011(4) -0.002(4) -0.009(4) C5 0.059(5) 0.048(5) 0.072(6) -0.020(4) 0.013(5) -0.018(4) C6 0.064(6) 0.050(5) 0.080(6) -0.027(5) 0.012(5) -0.025(4) C7 0.049(5) 0.041(4) 0.047(4) -0.001(4) 0.003(4) -0.017(4) C8 0.048(5) 0.043(5) 0.050(5) 0.009(4) 0.000(4) -0.007(4) C9 0.051(5) 0.052(5) 0.043(4) -0.006(4) -0.003(4) -0.024(4) C10 0.053(6) 0.084(7) 0.080(7) -0.020(6) -0.013(5) 0.001(5) C11 0.077(7) 0.088(7) 0.066(6) -0.024(6) -0.009(5) -0.016(6) C12 0.067(6) 0.053(5) 0.045(4) -0.007(4) -0.004(4) -0.023(4) C13 0.131(9) 0.044(5) 0.048(5) -0.003(4) 0.000(6) -0.023(5) C14 0.112(8) 0.050(5) 0.054(5) -0.019(4) -0.002(5) -0.025(5) C15 0.055(5) 0.049(5) 0.047(5) -0.011(4) -0.006(4) -0.013(4) C16 0.091(7) 0.037(4) 0.070(6) -0.020(4) 0.017(5) -0.031(5) C17 0.099(7) 0.046(5) 0.058(5) -0.025(4) 0.004(5) -0.016(5) C18 0.054(5) 0.036(4) 0.041(4) -0.004(3) -0.001(4) -0.010(4) C19 0.048(5) 0.049(5) 0.052(5) -0.004(4) 0.000(4) -0.013(4) C20 0.041(5) 0.043(4) 0.058(5) -0.010(4) 0.006(4) -0.009(4) C22 0.054(6) 0.081(7) 0.081(7) -0.025(6) 0.005(5) -0.002(5) I1 0.0611(4) 0.0741(5) 0.0694(4) -0.0215(3) 0.0167(3) -0.0246(3) I2 0.1263(7) 0.0748(5) 0.0528(4) -0.0150(3) 0.0119(4) -0.0444(4) N1 0.060(5) 0.038(4) 0.075(5) -0.011(3) 0.019(4) -0.015(3) N2 0.085(5) 0.055(4) 0.050(4) -0.018(3) 0.006(4) -0.030(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C21 C19 1.483(12) . ? C1 C6 1.368(11) . ? C1 C2 1.402(11) . ? C1 I1 2.099(8) . ? C2 C3 1.360(11) . ? C3 C4 1.367(11) . ? C4 N1 1.380(10) . ? C4 C5 1.389(11) . ? C5 C6 1.366(11) . ? C7 C9 1.383(11) . ? C7 N1 1.412(10) . ? C7 C8 1.417(12) . ? C8 C9 1.391(12) 2_766 ? C8 C10 1.492(13) . ? C9 C8 1.391(12) 2_766 ? C9 C11 1.515(12) . ? C12 C13 1.361(12) . ? C12 C17 1.368(11) . ? C12 I2 2.079(8) . ? C13 C14 1.399(12) . ? C14 C15 1.377(11) . ? C15 C16 1.380(11) . ? C15 N2 1.385(10) . ? C16 C17 1.360(11) . ? C18 C20 1.382(11) 2_756 ? C18 C19 1.410(11) . ? C18 N2 1.420(10) . ? C19 C20 1.388(11) . ? C20 C18 1.382(11) 2_756 ? C20 C22 1.511(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 119.8(8) . . ? C6 C1 I1 120.4(6) . . ? C2 C1 I1 119.7(6) . . ? C3 C2 C1 118.9(8) . . ? C2 C3 C4 122.2(8) . . ? C3 C4 N1 120.4(7) . . ? C3 C4 C5 118.2(8) . . ? N1 C4 C5 121.4(7) . . ? C6 C5 C4 121.0(8) . . ? C5 C6 C1 120.0(8) . . ? C9 C7 N1 120.0(8) . . ? C9 C7 C8 121.5(7) . . ? N1 C7 C8 118.5(8) . . ? C9 C8 C7 118.1(8) 2_766 . ? C9 C8 C10 122.0(9) 2_766 . ? C7 C8 C10 119.8(8) . . ? C7 C9 C8 120.4(7) . 2_766 ? C7 C9 C11 119.1(8) . . ? C8 C9 C11 120.5(8) 2_766 . ? C13 C12 C17 119.6(8) . . ? C13 C12 I2 119.6(6) . . ? C17 C12 I2 120.8(6) . . ? C12 C13 C14 119.4(8) . . ? C15 C14 C13 121.4(8) . . ? C14 C15 C16 117.3(8) . . ? C14 C15 N2 122.3(8) . . ? C16 C15 N2 120.5(7) . . ? C17 C16 C15 121.6(8) . . ? C16 C17 C12 120.8(8) . . ? C20 C18 C19 121.2(7) 2_756 . ? C20 C18 N2 119.5(7) 2_756 . ? C19 C18 N2 119.3(8) . . ? C20 C19 C18 119.1(8) . . ? C20 C19 C21 121.5(8) . . ? C18 C19 C21 119.3(8) . . ? C18 C20 C19 119.7(7) 2_756 . ? C18 C20 C22 119.1(8) 2_756 . ? C19 C20 C22 121.1(8) . . ? C4 N1 C7 124.8(6) . . ? C15 N2 C18 122.0(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.3(14) . . . . ? I1 C1 C2 C3 -176.6(7) . . . . ? C1 C2 C3 C4 -0.5(15) . . . . ? C2 C3 C4 N1 177.9(9) . . . . ? C2 C3 C4 C5 0.2(14) . . . . ? C3 C4 C5 C6 0.2(14) . . . . ? N1 C4 C5 C6 -177.5(9) . . . . ? C4 C5 C6 C1 -0.4(15) . . . . ? C2 C1 C6 C5 0.1(15) . . . . ? I1 C1 C6 C5 176.9(7) . . . . ? C9 C7 C8 C9 -1.2(12) . . . 2_766 ? N1 C7 C8 C9 178.3(7) . . . 2_766 ? C9 C7 C8 C10 178.4(8) . . . . ? N1 C7 C8 C10 -2.1(11) . . . . ? N1 C7 C9 C8 -178.2(7) . . . 2_766 ? C8 C7 C9 C8 1.3(12) . . . 2_766 ? N1 C7 C9 C11 4.4(11) . . . . ? C8 C7 C9 C11 -176.1(8) . . . . ? C17 C12 C13 C14 1.5(16) . . . . ? I2 C12 C13 C14 -177.3(8) . . . . ? C12 C13 C14 C15 0.5(17) . . . . ? C13 C14 C15 C16 -1.9(15) . . . . ? C13 C14 C15 N2 178.5(9) . . . . ? C14 C15 C16 C17 1.3(15) . . . . ? N2 C15 C16 C17 -179.1(9) . . . . ? C15 C16 C17 C12 0.7(16) . . . . ? C13 C12 C17 C16 -2.1(16) . . . . ? I2 C12 C17 C16 176.6(8) . . . . ? C20 C18 C19 C20 -1.9(13) 2_756 . . . ? N2 C18 C19 C20 179.1(7) . . . . ? C20 C18 C19 C21 179.2(8) 2_756 . . . ? N2 C18 C19 C21 0.2(12) . . . . ? C18 C19 C20 C18 1.9(12) . . . 2_756 ? C21 C19 C20 C18 -179.3(8) . . . 2_756 ? C18 C19 C20 C22 -178.6(7) . . . . ? C21 C19 C20 C22 0.2(13) . . . . ? C3 C4 N1 C7 173.7(8) . . . . ? C5 C4 N1 C7 -8.7(14) . . . . ? C9 C7 N1 C4 -96.3(10) . . . . ? C8 C7 N1 C4 84.1(10) . . . . ? C14 C15 N2 C18 -14.5(14) . . . . ? C16 C15 N2 C18 166.0(8) . . . . ? C20 C18 N2 C15 -80.3(10) 2_756 . . . ? C19 C18 N2 C15 98.8(10) . . . . ?