# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address 'Jun Yoshida' ; Department of Basic Science, Graduate School of Arts and Sciences, The University of Tokyo, 3-8-1 Komaba, Meguro-ku, Tokyo 153-8902, Japan ; 'Junta Fuchiwaki' ; Department of Basic Science, Graduate School of Arts and Sciences, The University of Tokyo, 3-8-1 Komaba, Meguro-ku, Tokyo 153-8902, Japan ; 'Shin-ichi Nishikiori' ; Department of Basic Science, Graduate School of Arts and Sciences, The University of Tokyo, 3-8-1 Komaba, Meguro-ku, Tokyo 153-8902, Japan ; _publ_contact_author_address ; Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa, 252-0329, Japan. ; _publ_contact_author_email yoshidaj@kitasato-u.ac.jp _publ_contact_author_fax '+81 042-778-7980' _publ_contact_author_phone '+81 042-778-9953' #TrackingRef '1.cif' _publ_contact_author_name 'Jun Yoshida' data_1-I- _database_code_depnum_ccdc_archive 'CCDC 814012' #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H12 N O, I' _chemical_formula_sum 'C13 H12 I N O' _chemical_formula_weight 325.14 #============================================================================== # CRYSTAL DATA _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 10.7451(7) _cell_length_b 8.1032(5) _cell_length_c 15.3586(10) _cell_angle_alpha 90 _cell_angle_beta 109.2790(10) _cell_angle_gamma 90 _cell_volume 1262.28(14) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2979 _cell_measurement_theta_min 2.8101 _cell_measurement_theta_max 27.0006 _cell_measurement_temperature 296(2) _exptl_crystal_colour 'light brown' _exptl_crystal_description plate _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.711 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 2.516 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.51 _exptl_absorpt_correction_T_max 0.7 #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 6819 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_unetI/netI 0.0279 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #============================================================================== # REFINEMENT DATA _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. ; _reflns_number_total 2837 _reflns_number_gt 2315 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0332 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.061 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_number_reflns 2837 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment noref _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0313P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.276 _refine_diff_density_min -0.563 _refine_diff_density_rms 0.082 _refine_ls_extinction_method none 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.7428(3) -0.0082(4) 0.48100(18) 0.0536(6) Uani d . 1 . . C H1 0.6791 -0.0837 0.4838 0.064 Uiso calc R 1 . . H C2 0.7667(3) 0.0172(4) 0.39939(19) 0.0626(8) Uani d . 1 . . C H2 0.7197 -0.0416 0.3468 0.075 Uiso calc R 1 . . H C3 0.8607(3) 0.1300(4) 0.39605(19) 0.0591(7) Uani d . 1 . . C H3 0.8785 0.147 0.3414 0.071 Uiso calc R 1 . . H C4 0.9277(3) 0.2171(3) 0.4736(2) 0.0564(7) Uani d . 1 . . C H4 0.9901 0.2954 0.4718 0.068 Uiso calc R 1 . . H C5 0.9024(3) 0.1884(3) 0.55389(18) 0.0487(6) Uani d . 1 . . C H5 0.9482 0.2468 0.6069 0.058 Uiso calc R 1 . . H N1 0.8120(2) 0.0766(2) 0.55668(13) 0.0408(4) Uani d . 1 . . N C6 0.7930(3) 0.0414(3) 0.64545(17) 0.0478(6) Uani d . 1 . . C H6 0.8636 0.0929 0.6946 0.057 Uiso calc R 1 . . H H6A 0.7988 -0.0768 0.656 0.057 Uiso calc R 1 . . H C7 0.6617(2) 0.1027(3) 0.64959(16) 0.0406(5) Uani d . 1 . . C C8 0.6444(2) 0.0853(3) 0.74154(17) 0.0415(5) Uani d . 1 . . C C9 0.7255(2) -0.0157(3) 0.81038(16) 0.0473(6) Uani d . 1 . . C H9 0.7927 -0.0758 0.7996 0.057 Uiso calc R 1 . . H C10 0.7059(3) -0.0265(4) 0.89462(18) 0.0566(7) Uani d . 1 . . C H10 0.7606 -0.0934 0.9406 0.068 Uiso calc R 1 . . H C11 0.6066(3) 0.0605(4) 0.9111(2) 0.0628(8) Uani d . 1 . . C H11 0.5937 0.0515 0.9679 0.075 Uiso calc R 1 . . H C12 0.5255(3) 0.1616(4) 0.8434(2) 0.0665(8) Uani d . 1 . . C H12 0.4584 0.221 0.8547 0.08 Uiso calc R 1 . . H C13 0.5445(3) 0.1743(4) 0.75862(18) 0.0540(6) Uani d . 1 . . C H13 0.4901 0.2424 0.7131 0.065 Uiso calc R 1 . . H O1 0.57797(18) 0.1589(3) 0.58298(12) 0.0594(5) Uani d . 1 . . O I1 0.861141(16) -0.08344(2) 0.170011(11) 0.05165(8) Uani d . 1 . . I loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0479(16) 0.0592(17) 0.0528(15) -0.0032(13) 0.0155(12) -0.0075(13) C2 0.0625(19) 0.077(2) 0.0456(15) 0.0076(16) 0.0143(13) -0.0105(15) C3 0.0688(19) 0.0662(19) 0.0511(15) 0.0224(15) 0.0316(14) 0.0122(14) C4 0.0598(17) 0.0486(16) 0.0717(18) 0.0051(12) 0.0363(15) 0.0099(13) C5 0.0492(15) 0.0440(14) 0.0543(14) 0.0024(11) 0.0190(12) -0.0020(12) N1 0.0399(11) 0.0448(12) 0.0397(10) 0.0070(9) 0.0160(8) 0.0013(9) C6 0.0448(15) 0.0600(16) 0.0416(12) 0.0097(12) 0.0183(11) 0.0075(11) C7 0.0390(13) 0.0415(14) 0.0411(12) -0.0009(10) 0.0130(10) -0.0001(10) C8 0.0362(12) 0.0469(14) 0.0429(12) -0.0047(10) 0.0151(10) -0.0043(10) C9 0.0466(15) 0.0512(15) 0.0452(14) 0.0019(11) 0.0166(11) 0.0023(12) C10 0.0609(18) 0.0654(18) 0.0446(14) -0.0091(14) 0.0192(13) 0.0028(13) C11 0.070(2) 0.078(2) 0.0498(15) -0.0229(16) 0.0332(15) -0.0077(14) C12 0.0594(18) 0.082(2) 0.0714(19) -0.0023(16) 0.0401(16) -0.0088(18) C13 0.0448(14) 0.0659(18) 0.0544(15) 0.0066(13) 0.0207(12) 0.0012(13) O1 0.0472(11) 0.0822(13) 0.0473(10) 0.0158(10) 0.0135(8) 0.0114(10) I1 0.05499(13) 0.05572(13) 0.04580(11) -0.00214(8) 0.01876(8) -0.00023(7) #============================================================================== # 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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 N1 . 1.343(3) ? C1 C2 . 1.375(4) ? C1 H1 . 0.93 ? C2 C3 . 1.376(4) ? C2 H2 . 0.93 ? C3 C4 . 1.367(4) ? C3 H3 . 0.93 ? C4 C5 . 1.368(4) ? C4 H4 . 0.93 ? C5 N1 . 1.339(3) ? C5 H5 . 0.93 ? N1 C6 . 1.472(3) ? C6 C7 . 1.517(3) ? C6 H6 . 0.97 ? C6 H6A . 0.97 ? C7 O1 . 1.206(3) ? C7 C8 . 1.490(3) ? C8 C13 . 1.389(3) ? C8 C9 . 1.392(3) ? C9 C10 . 1.381(3) ? C9 H9 . 0.93 ? C10 C11 . 1.370(4) ? C10 H10 . 0.93 ? C11 C12 . 1.383(5) ? C11 H11 . 0.93 ? C12 C13 . 1.386(4) ? C12 H12 . 0.93 ? C13 H13 . 0.93 ? 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 N1 C1 C2 119.7(3) . . ? N1 C1 H1 120.1 . . ? C2 C1 H1 120.1 . . ? C1 C2 C3 119.6(3) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 119.5(3) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 119.6(3) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 120.4(3) . . ? N1 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 N1 C1 121.2(2) . . ? C5 N1 C6 119.0(2) . . ? C1 N1 C6 119.7(2) . . ? N1 C6 C7 113.0(2) . . ? N1 C6 H6 109 . . ? C7 C6 H6 109 . . ? N1 C6 H6A 109 . . ? C7 C6 H6A 109 . . ? H6 C6 H6A 107.8 . . ? O1 C7 C8 123.2(2) . . ? O1 C7 C6 122.1(2) . . ? C8 C7 C6 114.6(2) . . ? C13 C8 C9 119.4(2) . . ? C13 C8 C7 118.4(2) . . ? C9 C8 C7 122.2(2) . . ? C10 C9 C8 119.9(3) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C11 C10 C9 120.7(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.0(3) . . ? C10 C11 H11 120 . . ? C12 C11 H11 120 . . ? C11 C12 C13 119.9(3) . . ? C11 C12 H12 120 . . ? C13 C12 H12 120 . . ? C12 C13 C8 120.1(3) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? 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 N1 C1 C2 C3 -0.4(4) . . . . ? C1 C2 C3 C4 -0.9(4) . . . . ? C2 C3 C4 C5 1.4(4) . . . . ? C3 C4 C5 N1 -0.4(4) . . . . ? C4 C5 N1 C1 -0.9(4) . . . . ? C4 C5 N1 C6 176.3(2) . . . . ? C2 C1 N1 C5 1.4(4) . . . . ? C2 C1 N1 C6 -175.8(2) . . . . ? C5 N1 C6 C7 110.7(3) . . . . ? C1 N1 C6 C7 -72.0(3) . . . . ? N1 C6 C7 O1 7.0(4) . . . . ? N1 C6 C7 C8 -173.9(2) . . . . ? O1 C7 C8 C13 -17.1(4) . . . . ? C6 C7 C8 C13 163.8(2) . . . . ? O1 C7 C8 C9 163.3(2) . . . . ? C6 C7 C8 C9 -15.7(3) . . . . ? C13 C8 C9 C10 0.0(4) . . . . ? C7 C8 C9 C10 179.5(2) . . . . ? C8 C9 C10 C11 0.5(4) . . . . ? C9 C10 C11 C12 -0.6(5) . . . . ? C10 C11 C12 C13 0.3(5) . . . . ? C11 C12 C13 C8 0.2(5) . . . . ? C9 C8 C13 C12 -0.3(4) . . . . ? C7 C8 C13 C12 -179.9(3) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF # Attachment '2.cif' data_1-I-I3- _database_code_depnum_ccdc_archive 'CCDC 814013' #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_formula_sum 'C13 H12 I2 N O' _chemical_formula_moiety 'C13 H12 N O, 0.5(I3), 0.5(I)' _chemical_formula_weight 452.04 _chemical_absolute_configuration ad #============================================================================== # CRYSTAL DATA _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P 21 21 2' _space_group_name_Hall 'P 2 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 9.1134(3) _cell_length_b 11.0264(4) _cell_length_c 14.6077(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1467.90(9) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9974 _cell_measurement_theta_min 2.7888 _cell_measurement_theta_max 27.4528 _cell_measurement_temperature 100(2) _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 2.045 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 4.27 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.55 _exptl_absorpt_correction_T_max 0.76 #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 16391 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_unetI/netI 0.0196 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #============================================================================== # REFINEMENT DATA _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. ; _reflns_number_total 3360 _reflns_number_gt 3271 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0145 _refine_ls_R_factor_gt 0.0136 _refine_ls_wR_factor_ref 0.0306 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_number_reflns 3360 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment noref _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0087P)^2^+0.5580P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.324 _refine_diff_density_min -0.35 _refine_diff_density_rms 0.064 _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.014(17) 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' _computing_data_collection ? _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.0575(3) 0.2267(2) 0.30194(17) 0.0178(5) Uani d . 1 . . C H1 -0.0001 0.2889 0.329 0.021 Uiso calc R 1 . . H C2 0.0509(3) 0.2078(2) 0.20946(17) 0.0199(5) Uani d . 1 . . C H2 -0.0116 0.2563 0.1725 0.024 Uiso calc R 1 . . H C3 0.1354(3) 0.1178(2) 0.16997(18) 0.0232(5) Uani d . 1 . . C H3 0.1312 0.1036 0.1059 0.028 Uiso calc R 1 . . H C4 0.2267(3) 0.0485(2) 0.22541(18) 0.0240(5) Uani d . 1 . . C H4 0.2867 -0.0129 0.1993 0.029 Uiso calc R 1 . . H C5 0.2296(3) 0.06914(19) 0.31810(16) 0.0188(5) Uani d . 1 . . C H5 0.2909 0.0212 0.3563 0.023 Uiso calc R 1 . . H N1 0.14572(19) 0.15736(17) 0.35516(13) 0.0139(4) Uani d . 1 . . N C6 0.1537(2) 0.1805(2) 0.45361(15) 0.0151(4) Uani d . 1 . . C H6 0.1793 0.2667 0.4639 0.018 Uiso calc R 1 . . H H7 0.2328 0.1302 0.4804 0.018 Uiso calc R 1 . . H C7 0.0096(2) 0.15223(17) 0.50217(14) 0.0139(4) Uani d . 1 . . C C8 0.0103(3) 0.16573(18) 0.60320(13) 0.0143(4) Uani d . 1 . . C C9 0.1283(3) 0.2180(2) 0.64992(17) 0.0184(5) Uani d . 1 . . C H8 0.2101 0.2481 0.6166 0.022 Uiso calc R 1 . . H C10 0.1265(3) 0.2260(3) 0.74413(17) 0.0229(6) Uani d . 1 . . C H9 0.2069 0.262 0.7754 0.027 Uiso calc R 1 . . H C11 0.0077(3) 0.1815(2) 0.79365(15) 0.0225(5) Uani d . 1 . . C H10 0.0066 0.1875 0.8585 0.027 Uiso calc R 1 . . H C12 -0.1094(3) 0.1284(2) 0.74788(16) 0.0194(5) Uani d . 1 . . C H11 -0.1901 0.0972 0.7816 0.023 Uiso calc R 1 . . H C13 -0.1090(2) 0.1207(2) 0.65373(17) 0.0160(5) Uani d . 1 . . C H12 -0.1898 0.0848 0.6229 0.019 Uiso calc R 1 . . H O1 -0.09795(16) 0.11951(14) 0.45948(11) 0.0181(3) Uani d . 1 . . O I1 0 0.5 0.466725(13) 0.01648(5) Uani d S 1 . . I I2 0.258054(18) 0.342184(14) 0.990830(10) 0.02563(4) Uani d . 1 . . I I3 0 0.5 0.992396(14) 0.02163(5) Uani d S 1 . . I loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0148(11) 0.0196(11) 0.0191(13) -0.0003(9) -0.0009(9) 0.0014(10) C2 0.0203(12) 0.0219(12) 0.0175(13) -0.0057(9) -0.0030(9) 0.0034(10) C3 0.0310(14) 0.0235(13) 0.0152(12) -0.0096(10) 0.0018(10) -0.0040(10) C4 0.0301(14) 0.0206(11) 0.0214(12) -0.0008(11) 0.0081(12) -0.0036(10) C5 0.0205(12) 0.0160(11) 0.0198(11) 0.0015(9) 0.0037(10) -0.0012(9) N1 0.0138(9) 0.0145(9) 0.0134(9) -0.0022(8) 0.0013(7) -0.0001(8) C6 0.0140(10) 0.0179(11) 0.0134(11) -0.0005(8) 0.0002(8) -0.0022(9) C7 0.0144(9) 0.0097(8) 0.0177(10) 0.0017(9) 0.0003(10) 0.0012(8) C8 0.0147(10) 0.0125(9) 0.0156(10) 0.0033(10) 0.0017(10) 0.0009(8) C9 0.0155(11) 0.0219(12) 0.0179(12) -0.0046(10) 0.0008(9) 0.0004(10) C10 0.0185(13) 0.0301(13) 0.0200(14) -0.0038(11) -0.0017(10) -0.0015(11) C11 0.0258(12) 0.0291(12) 0.0127(10) 0.0003(13) 0.0009(11) -0.0016(9) C12 0.0166(12) 0.0224(13) 0.0192(13) 0.0020(9) 0.0052(9) 0.0035(9) C13 0.0127(11) 0.0146(11) 0.0207(12) 0.0031(8) -0.0004(9) -0.0003(9) O1 0.0153(8) 0.0211(8) 0.0180(9) -0.0010(6) -0.0014(7) -0.0012(7) I1 0.01340(8) 0.01467(8) 0.02137(10) 0.00080(8) 0 0 I2 0.02686(8) 0.03457(8) 0.01546(7) 0.00285(7) -0.00099(7) 0.00523(6) I3 0.02339(10) 0.02641(10) 0.01510(10) -0.00466(9) 0 0 #============================================================================== # 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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 N1 . 1.355(3) ? C1 C2 . 1.368(4) ? C1 H1 . 0.95 ? C2 C3 . 1.382(4) ? C2 H2 . 0.95 ? C3 C4 . 1.390(4) ? C3 H3 . 0.95 ? C4 C5 . 1.373(3) ? C4 H4 . 0.95 ? C5 N1 . 1.350(3) ? C5 H5 . 0.95 ? N1 C6 . 1.462(3) ? C6 C7 . 1.525(3) ? C6 H6 . 0.99 ? C6 H7 . 0.99 ? C7 O1 . 1.217(3) ? C7 C8 . 1.483(3) ? C8 C9 . 1.398(3) ? C8 C13 . 1.405(3) ? C9 C10 . 1.379(3) ? C9 H8 . 0.95 ? C10 C11 . 1.392(4) ? C10 H9 . 0.95 ? C11 C12 . 1.389(4) ? C11 H10 . 0.95 ? C12 C13 . 1.378(3) ? C12 H11 . 0.95 ? C13 H12 . 0.95 ? I2 I3 . 2.92563(17) ? I3 I2 2_565 2.92563(17) ? 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 N1 C1 C2 120.4(2) . . ? N1 C1 H1 119.8 . . ? C2 C1 H1 119.8 . . ? C1 C2 C3 119.8(2) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 119.0(2) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 119.7(2) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? N1 C5 C4 120.3(2) . . ? N1 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 N1 C1 120.8(2) . . ? C5 N1 C6 119.44(19) . . ? C1 N1 C6 119.71(19) . . ? N1 C6 C7 112.26(17) . . ? N1 C6 H6 109.2 . . ? C7 C6 H6 109.2 . . ? N1 C6 H7 109.2 . . ? C7 C6 H7 109.2 . . ? H6 C6 H7 107.9 . . ? O1 C7 C8 122.9(2) . . ? O1 C7 C6 121.08(19) . . ? C8 C7 C6 116.03(19) . . ? C9 C8 C13 119.0(2) . . ? C9 C8 C7 122.0(2) . . ? C13 C8 C7 118.9(2) . . ? C10 C9 C8 120.3(2) . . ? C10 C9 H8 119.8 . . ? C8 C9 H8 119.8 . . ? C9 C10 C11 120.4(2) . . ? C9 C10 H9 119.8 . . ? C11 C10 H9 119.8 . . ? C12 C11 C10 119.8(2) . . ? C12 C11 H10 120.1 . . ? C10 C11 H10 120.1 . . ? C13 C12 C11 120.3(2) . . ? C13 C12 H11 119.8 . . ? C11 C12 H11 119.8 . . ? C12 C13 C8 120.3(2) . . ? C12 C13 H12 119.9 . . ? C8 C13 H12 119.9 . . ? I2 I3 I2 179.105(9) 2_565 . ? 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 N1 C1 C2 C3 -0.4(4) . . . . ? C1 C2 C3 C4 -0.4(4) . . . . ? C2 C3 C4 C5 1.0(4) . . . . ? C3 C4 C5 N1 -0.8(4) . . . . ? C4 C5 N1 C1 0.0(3) . . . . ? C4 C5 N1 C6 -178.1(2) . . . . ? C2 C1 N1 C5 0.6(3) . . . . ? C2 C1 N1 C6 178.7(2) . . . . ? C5 N1 C6 C7 -115.0(2) . . . . ? C1 N1 C6 C7 66.8(3) . . . . ? N1 C6 C7 O1 -3.0(3) . . . . ? N1 C6 C7 C8 176.35(17) . . . . ? O1 C7 C8 C9 -171.7(2) . . . . ? C6 C7 C8 C9 9.1(3) . . . . ? O1 C7 C8 C13 10.7(3) . . . . ? C6 C7 C8 C13 -168.63(19) . . . . ? C13 C8 C9 C10 -0.6(3) . . . . ? C7 C8 C9 C10 -178.3(2) . . . . ? C8 C9 C10 C11 0.4(4) . . . . ? C9 C10 C11 C12 0.3(4) . . . . ? C10 C11 C12 C13 -0.7(4) . . . . ? C11 C12 C13 C8 0.5(3) . . . . ? C9 C8 C13 C12 0.2(3) . . . . ? C7 C8 C13 C12 177.9(2) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF # Attachment '3.cif' data_1-I3- _database_code_depnum_ccdc_archive 'CCDC 814014' #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H12 N O, I3' _chemical_formula_sum 'C13 H12 I3 N O' _chemical_formula_weight 578.94 #============================================================================== # CRYSTAL DATA _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5788(8) _cell_length_b 7.8985(7) _cell_length_c 42.819(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3239.6(5) _cell_formula_units_Z 8 _cell_measurement_reflns_used 5941 _cell_measurement_theta_min 2.3293 _cell_measurement_theta_max 27.4493 _cell_measurement_temperature 120(2) _exptl_crystal_description rod _exptl_crystal_colour red-black _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.17 _exptl_crystal_density_diffrn 2.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2112 _exptl_absorpt_coefficient_mu 5.778 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.37 _exptl_absorpt_correction_T_max 0.44 #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 16677 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_unetI/netI 0.0236 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -55 _diffrn_reflns_limit_l_max 32 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #============================================================================== # REFINEMENT DATA _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. ; _reflns_number_total 3671 _reflns_number_gt 3026 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.0772 _refine_ls_goodness_of_fit_ref 1.191 _refine_ls_restrained_S_all 1.191 _refine_ls_number_reflns 3671 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment noref _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+35.8779P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.457 _refine_diff_density_min -1.447 _refine_diff_density_rms 0.167 _refine_ls_extinction_method none 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.2820(8) -0.0265(9) 0.29953(16) 0.0301(15) Uani d . 1 . . C H1 0.2056 -0.0936 0.3063 0.036 Uiso calc R 1 . . H C2 0.2986(9) 0.0086(10) 0.26820(17) 0.0387(18) Uani d . 1 . . C H2 0.2339 -0.035 0.2534 0.046 Uiso calc R 1 . . H C3 0.4090(9) 0.1070(10) 0.25829(17) 0.042(2) Uani d . 1 . . C H3 0.4203 0.1302 0.2367 0.05 Uiso calc R 1 . . H C4 0.5029(9) 0.1716(10) 0.27946(18) 0.0400(19) Uani d . 1 . . C H4 0.5785 0.2394 0.2724 0.048 Uiso calc R 1 . . H C5 0.4875(7) 0.1381(9) 0.31099(17) 0.0297(15) Uani d . 1 . . C H5 0.5515 0.1837 0.3257 0.036 Uiso calc R 1 . . H C6 0.3761(7) 0.0357(8) 0.32105(15) 0.0252(14) Uani d . 1 . . C C7 0.3566(6) -0.0064(8) 0.35458(15) 0.0228(14) Uani d . 1 . . C C8 0.4532(7) 0.0862(8) 0.37753(14) 0.0241(14) Uani d . 1 . . C H6 0.5515 0.0565 0.3729 0.029 Uiso calc R 1 . . H H7 0.4424 0.21 0.3749 0.029 Uiso calc R 1 . . H N1 0.4201(5) 0.0397(7) 0.40984(12) 0.0208(11) Uani d . 1 . . N C9 0.5083(7) -0.0567(8) 0.42689(15) 0.0230(13) Uani d . 1 . . C H8 0.5941 -0.0931 0.418 0.028 Uiso calc R 1 . . H C10 0.4754(7) -0.1027(9) 0.45685(17) 0.0291(15) Uani d . 1 . . C H9 0.5384 -0.1695 0.4688 0.035 Uiso calc R 1 . . H C11 0.3498(7) -0.0511(8) 0.46963(15) 0.0275(15) Uani d . 1 . . C H10 0.3257 -0.0825 0.4904 0.033 Uiso calc R 1 . . H C12 0.2596(8) 0.0470(9) 0.45193(15) 0.0268(14) Uani d . 1 . . C H11 0.1731 0.0835 0.4604 0.032 Uiso calc R 1 . . H C13 0.2961(7) 0.0908(8) 0.42199(16) 0.0240(14) Uani d . 1 . . C H12 0.2342 0.1572 0.4097 0.029 Uiso calc R 1 . . H O1 0.2689(5) -0.1034(6) 0.36414(10) 0.0298(11) Uani d . 1 . . O I1 0.11244(5) 0.12792(6) 0.537933(10) 0.03043(12) Uani d . 1 . . I I2 0.11064(4) -0.01671(5) 0.601814(10) 0.02338(10) Uani d . 1 . . I I3 0.11197(6) -0.16053(7) 0.663109(11) 0.03967(14) Uani d . 1 . . I loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.034(4) 0.027(4) 0.029(4) 0.001(3) -0.002(3) -0.001(3) C2 0.047(5) 0.039(4) 0.030(4) 0.006(4) -0.007(3) -0.003(3) C3 0.060(6) 0.043(5) 0.023(4) 0.017(4) 0.010(4) 0.006(3) C4 0.043(5) 0.040(4) 0.037(4) 0.002(4) 0.014(4) 0.008(4) C5 0.024(4) 0.034(4) 0.031(4) 0.000(3) 0.006(3) 0.001(3) C6 0.029(4) 0.019(3) 0.028(3) -0.001(3) 0.005(3) 0.003(3) C7 0.019(3) 0.020(3) 0.029(3) 0.002(2) 0.000(3) 0.000(3) C8 0.023(3) 0.025(3) 0.024(3) -0.006(3) 0.002(3) -0.001(3) N1 0.019(3) 0.020(3) 0.023(3) -0.005(2) -0.002(2) -0.002(2) C9 0.018(3) 0.020(3) 0.031(3) -0.001(3) 0.000(3) -0.005(3) C10 0.027(4) 0.023(3) 0.037(4) 0.005(3) -0.008(3) 0.002(3) C11 0.035(4) 0.026(3) 0.022(3) 0.000(3) -0.002(3) 0.000(3) C12 0.025(3) 0.026(3) 0.030(3) 0.000(3) 0.004(3) -0.002(3) C13 0.022(3) 0.020(3) 0.030(3) -0.001(3) -0.003(3) -0.002(3) O1 0.029(3) 0.036(3) 0.025(2) -0.013(2) 0.002(2) -0.001(2) I1 0.0290(2) 0.0335(2) 0.0287(2) 0.0039(2) 0.0018(2) 0.00231(19) I2 0.01936(19) 0.0222(2) 0.0286(2) -0.00068(17) 0.00281(18) -0.00423(16) I3 0.0410(3) 0.0468(3) 0.0313(3) -0.0106(3) 0.0011(2) 0.0060(2) #============================================================================== # 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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C6 . 1.379(10) ? C1 C2 . 1.379(10) ? C1 H1 . 0.95 ? C2 C3 . 1.380(11) ? C2 H2 . 0.95 ? C3 C4 . 1.375(12) ? C3 H3 . 0.95 ? C4 C5 . 1.384(10) ? C4 H4 . 0.95 ? C5 C6 . 1.407(9) ? C5 H5 . 0.95 ? C6 C7 . 1.486(9) ? C7 O1 . 1.209(8) ? C7 C8 . 1.535(9) ? C8 N1 . 1.466(8) ? C8 H6 . 0.99 ? C8 H7 . 0.99 ? N1 C9 . 1.352(8) ? N1 C13 . 1.359(8) ? C9 C10 . 1.370(9) ? C9 H8 . 0.95 ? C10 C11 . 1.383(10) ? C10 H9 . 0.95 ? C11 C12 . 1.386(9) ? C11 H10 . 0.95 ? C12 C13 . 1.373(9) ? C12 H11 . 0.95 ? C13 H12 . 0.95 ? I1 I2 . 2.9644(7) ? I2 I3 . 2.8599(7) ? 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 120.2(7) . . ? C6 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C1 C2 C3 120.0(7) . . ? C1 C2 H2 120 . . ? C3 C2 H2 120 . . ? C4 C3 C2 120.5(7) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 120.2(8) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 119.3(7) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C1 C6 C5 119.7(6) . . ? C1 C6 C7 119.0(6) . . ? C5 C6 C7 121.3(6) . . ? O1 C7 C6 123.8(6) . . ? O1 C7 C8 120.3(6) . . ? C6 C7 C8 115.9(5) . . ? N1 C8 C7 110.8(5) . . ? N1 C8 H6 109.5 . . ? C7 C8 H6 109.5 . . ? N1 C8 H7 109.5 . . ? C7 C8 H7 109.5 . . ? H6 C8 H7 108.1 . . ? C9 N1 C13 120.5(6) . . ? C9 N1 C8 121.0(5) . . ? C13 N1 C8 118.4(5) . . ? N1 C9 C10 120.7(6) . . ? N1 C9 H8 119.6 . . ? C10 C9 H8 119.6 . . ? C9 C10 C11 119.5(6) . . ? C9 C10 H9 120.2 . . ? C11 C10 H9 120.2 . . ? C10 C11 C12 119.4(6) . . ? C10 C11 H10 120.3 . . ? C12 C11 H10 120.3 . . ? C13 C12 C11 119.5(7) . . ? C13 C12 H11 120.2 . . ? C11 C12 H11 120.2 . . ? N1 C13 C12 120.4(6) . . ? N1 C13 H12 119.8 . . ? C12 C13 H12 119.8 . . ? I3 I2 I1 179.06(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.4(11) . . . . ? C1 C2 C3 C4 -0.4(12) . . . . ? C2 C3 C4 C5 0.2(12) . . . . ? C3 C4 C5 C6 0.8(11) . . . . ? C2 C1 C6 C5 1.3(11) . . . . ? C2 C1 C6 C7 -179.1(6) . . . . ? C4 C5 C6 C1 -1.5(11) . . . . ? C4 C5 C6 C7 178.9(7) . . . . ? C1 C6 C7 O1 6.0(10) . . . . ? C5 C6 C7 O1 -174.4(7) . . . . ? C1 C6 C7 C8 -172.1(6) . . . . ? C5 C6 C7 C8 7.5(9) . . . . ? O1 C7 C8 N1 -0.6(9) . . . . ? C6 C7 C8 N1 177.6(5) . . . . ? C7 C8 N1 C9 109.8(6) . . . . ? C7 C8 N1 C13 -67.9(7) . . . . ? C13 N1 C9 C10 -1.0(9) . . . . ? C8 N1 C9 C10 -178.6(6) . . . . ? N1 C9 C10 C11 0.6(10) . . . . ? C9 C10 C11 C12 -0.2(10) . . . . ? C10 C11 C12 C13 0.2(10) . . . . ? C9 N1 C13 C12 0.9(9) . . . . ? C8 N1 C13 C12 178.6(6) . . . . ? C11 C12 C13 N1 -0.5(10) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF