# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 #TrackingRef '1-H2PO4-CIF.txt' #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2011-05-11 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ? #============================================================================== # # SUBMISSION DETAILS _publ_contact_author_name 'Pierangelo Metrangolo' # Name of author for correspondence _publ_contact_author_address ;Department of Chemistry University of Anywhere Sometown Somewhere, UK ; # Address of author for correspondence _publ_contact_author_email pierangelo.metrangolo@polimi.it _publ_contact_author_fax 00(000)0000000 _publ_contact_author_phone 00(000)0000000 _publ_contact_letter ; Submission dated :2011-05-11 Please consider this CIF for submission to the Cambridge Crystallographic Data Centre. I certify that all authors have seen and approved of this submission, that all have made significant scientific contributions to the work reported, and that all share responsibility and accountability for the results. This CIF is submitted as a personal communication This CIF is submitted as part of a journal submission Bloggs, Joe J. ; #============================================================================== # # TITLE AND AUTHOR LIST _publ_section_title ; ? ; _publ_section_title_footnote ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_footnote _publ_author_address #<--'Last name, first name' ; ? ; ;Department of Chemistry University of Anywhere Sometown Somewhere, UK ; loop_ _publ_author_name 'Massimo Cametti' 'Kari Raatikainen' 'Pierangelo Metrangolo' 'Giancarlo Terraneo' 'Tullio Pilati' 'Giu-seppe Resnati' # 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 '1-I-CIF.txt' data_mc02 _database_code_depnum_ccdc_archive 'CCDC 828713' #TrackingRef '1-I-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 I N2 1+, I 1-' _chemical_formula_sum 'C20 H18 I2 N2' _chemical_formula_weight 540.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.2333(4) _cell_length_b 10.2275(6) _cell_length_c 21.9756(12) _cell_angle_alpha 90.00 _cell_angle_beta 92.507(2) _cell_angle_gamma 90.00 _cell_volume 1848.71(17) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 9041 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 34.17 _exptl_crystal_description 'elongated table' _exptl_crystal_colour brown _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.941 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 3.406 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.6092 _exptl_absorpt_correction_T_max 0.7468 _exptl_special_details ; All the crystals were visibly twinned and any attempt to cut a single piece failed. Forthe data collection, at the end, we decided to use a piece having the most unbalanced ratio of reflection dureing the cell determination. For this crystal for the initial cell determination 4565 reflection were selected, 2225 in common, 1781 assigned exclusively to the major component and 459 to the minor one. The temperature was controlled by a Bruker KRYOFLEX low temperature device. ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 55642 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 0.93 _diffrn_reflns_theta_max 34.49 _reflns_number_total 6886 _reflns_number_gt 6520 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 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. The crystal was refined as TWIN with a final BASF = 0.02956. In spite of this the residue, especially around the iodine atoms were quite large and the second term of the SHELXL weighting scheme unusually large. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+47.6401P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6886 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1482 _refine_ls_wR_factor_gt 0.1467 _refine_ls_goodness_of_fit_ref 1.316 _refine_ls_restrained_S_all 1.316 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.25133(6) 0.71493(4) 0.551787(19) 0.01449(9) Uani 1 1 d . . . I2 I 0.24111(6) 0.42395(4) 0.488691(17) 0.01055(9) Uani 1 1 d . . . N1 N 0.1695(7) 0.2010(5) 0.3966(2) 0.0091(9) Uani 1 1 d . . . N2 N 0.2008(7) 0.1235(5) 0.4882(2) 0.0115(9) Uani 1 1 d . . . C1 C 0.3195(8) 0.1659(6) 0.2726(3) 0.0116(10) Uani 1 1 d . . . C2 C 0.4569(8) 0.1642(6) 0.3151(3) 0.0133(11) Uani 1 1 d . . . H2 H 0.4516 0.2102 0.3525 0.016 Uiso 1 1 calc R . . C3 C 0.5950(9) 0.0978(7) 0.3025(3) 0.0168(12) Uani 1 1 d . . . H3 H 0.6847 0.0987 0.3312 0.020 Uiso 1 1 calc R . . C4 C 0.6073(9) 0.0271(7) 0.2472(3) 0.0186(13) Uani 1 1 d . . . H4 H 0.7034 -0.0206 0.2398 0.022 Uiso 1 1 calc R . . C5 C 0.4819(9) 0.0278(7) 0.2050(3) 0.0174(12) Uani 1 1 d . . . H5 H 0.4917 -0.0183 0.1679 0.021 Uiso 1 1 calc R . . C6 C 0.3350(8) 0.0972(6) 0.2160(3) 0.0122(11) Uani 1 1 d . . . C7 C 0.2079(9) 0.1007(6) 0.1722(3) 0.0135(11) Uani 1 1 d . . . H7 H 0.2191 0.0568 0.1345 0.016 Uiso 1 1 calc R . . C8 C 0.0643(9) 0.1677(6) 0.1827(3) 0.0135(11) Uani 1 1 d . . . C9 C -0.0644(9) 0.1733(7) 0.1362(3) 0.0168(12) Uani 1 1 d . . . H9 H -0.0506 0.1301 0.0985 0.020 Uiso 1 1 calc R . . C10 C -0.2033(10) 0.2381(7) 0.1449(3) 0.0184(13) Uani 1 1 d . . . H10 H -0.2859 0.2416 0.1134 0.022 Uiso 1 1 calc R . . C11 C -0.2263(9) 0.3016(7) 0.2016(3) 0.0160(12) Uani 1 1 d . . . H11 H -0.3254 0.3462 0.2079 0.019 Uiso 1 1 calc R . . C12 C -0.1079(9) 0.2992(7) 0.2472(3) 0.0154(12) Uani 1 1 d . . . H12 H -0.1264 0.3424 0.2846 0.018 Uiso 1 1 calc R . . C13 C 0.0439(8) 0.2328(6) 0.2399(3) 0.0122(10) Uani 1 1 d . . . C14 C 0.1717(8) 0.2293(6) 0.2843(3) 0.0113(10) Uani 1 1 d . . . C15 C 0.1565(9) 0.2957(6) 0.3454(3) 0.0120(11) Uani 1 1 d . . . H15A H 0.2432 0.3623 0.3509 0.014 Uiso 1 1 calc R . . H15B H 0.0504 0.3411 0.3460 0.014 Uiso 1 1 calc R . . C16 C 0.2048(8) 0.2354(6) 0.4546(3) 0.0099(10) Uani 1 1 d . . . C17 C 0.1631(8) 0.0200(6) 0.4501(3) 0.0125(11) Uani 1 1 d . . . H17 H 0.1544 -0.0691 0.4616 0.015 Uiso 1 1 calc R . . C18 C 0.1407(9) 0.0690(6) 0.3930(3) 0.0130(11) Uani 1 1 d . . . H18 H 0.1108 0.0209 0.3573 0.016 Uiso 1 1 calc R . . C19 C 0.2362(9) 0.1141(6) 0.5544(3) 0.0155(12) Uani 1 1 d . . . H19A H 0.1886 0.0326 0.5701 0.019 Uiso 1 1 calc R . . H19B H 0.1864 0.1890 0.5751 0.019 Uiso 1 1 calc R . . C20 C 0.4205(11) 0.1143(9) 0.5680(4) 0.0275(17) Uani 1 1 d . . . H20A H 0.4689 0.1902 0.5485 0.041 Uiso 1 1 calc R . . H20B H 0.4676 0.0339 0.5521 0.041 Uiso 1 1 calc R . . H20C H 0.4427 0.1188 0.6121 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0191(2) 0.01026(16) 0.01396(17) -0.00126(13) -0.00061(14) -0.00022(14) I2 0.01388(18) 0.00950(15) 0.00820(14) -0.00117(11) -0.00041(12) -0.00011(13) N1 0.015(2) 0.0072(19) 0.0054(18) -0.0010(15) 0.0004(16) -0.0003(17) N2 0.015(3) 0.008(2) 0.012(2) 0.0008(16) 0.0061(18) -0.0043(17) C1 0.019(3) 0.008(2) 0.008(2) 0.0006(18) 0.002(2) -0.001(2) C2 0.014(3) 0.014(3) 0.012(2) -0.001(2) 0.000(2) -0.002(2) C3 0.016(3) 0.017(3) 0.017(3) 0.001(2) 0.000(2) -0.001(2) C4 0.018(3) 0.016(3) 0.022(3) 0.000(2) 0.003(2) 0.004(2) C5 0.020(3) 0.016(3) 0.017(3) -0.003(2) 0.005(2) 0.001(2) C6 0.018(3) 0.009(2) 0.010(2) -0.0018(18) 0.003(2) 0.000(2) C7 0.018(3) 0.013(2) 0.010(2) -0.0022(19) 0.002(2) -0.001(2) C8 0.021(3) 0.011(2) 0.008(2) -0.0006(19) 0.001(2) 0.000(2) C9 0.023(4) 0.017(3) 0.010(2) 0.000(2) -0.003(2) -0.006(2) C10 0.023(4) 0.018(3) 0.014(3) 0.004(2) -0.002(2) -0.006(2) C11 0.017(3) 0.015(3) 0.016(3) 0.002(2) 0.000(2) 0.001(2) C12 0.019(3) 0.014(3) 0.014(3) -0.001(2) 0.003(2) 0.001(2) C13 0.017(3) 0.010(2) 0.010(2) 0.0003(18) 0.000(2) 0.000(2) C14 0.017(3) 0.009(2) 0.008(2) -0.0010(18) 0.001(2) 0.000(2) C15 0.021(3) 0.009(2) 0.005(2) -0.0001(18) 0.0009(19) 0.001(2) C16 0.011(3) 0.012(2) 0.007(2) -0.0006(18) -0.0014(18) 0.0011(19) C17 0.019(3) 0.010(2) 0.009(2) -0.0007(18) 0.004(2) -0.001(2) C18 0.019(3) 0.009(2) 0.011(2) 0.0004(19) 0.001(2) -0.001(2) C19 0.023(3) 0.012(2) 0.012(2) 0.001(2) 0.002(2) -0.008(2) C20 0.022(4) 0.035(4) 0.025(4) 0.007(3) -0.002(3) -0.010(3) _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 I2 C16 2.086(6) . ? N1 C16 1.341(7) . ? N1 C18 1.372(8) . ? N1 C15 1.486(8) . ? N2 C16 1.364(8) . ? N2 C17 1.377(8) . ? N2 C19 1.473(8) . ? C1 C14 1.413(9) . ? C1 C2 1.435(9) . ? C1 C6 1.439(8) . ? C2 C3 1.363(10) . ? C2 H2 0.9500 . ? C3 C4 1.421(10) . ? C3 H3 0.9500 . ? C4 C5 1.357(11) . ? C4 H4 0.9500 . ? C5 C6 1.432(10) . ? C5 H5 0.9500 . ? C6 C7 1.391(9) . ? C7 C8 1.395(10) . ? C7 H7 0.9500 . ? C8 C13 1.440(9) . ? C8 C9 1.440(10) . ? C9 C10 1.343(11) . ? C9 H9 0.9500 . ? C10 C11 1.426(10) . ? C10 H10 0.9500 . ? C11 C12 1.367(10) . ? C11 H11 0.9500 . ? C12 C13 1.438(10) . ? C12 H12 0.9500 . ? C13 C14 1.403(9) . ? C14 C15 1.515(8) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C17 C18 1.355(9) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.533(11) . ? 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 C16 N1 C18 110.0(5) . . ? C16 N1 C15 123.6(5) . . ? C18 N1 C15 126.3(5) . . ? C16 N2 C17 109.0(5) . . ? C16 N2 C19 125.5(5) . . ? C17 N2 C19 125.5(5) . . ? C14 C1 C2 123.2(6) . . ? C14 C1 C6 119.4(6) . . ? C2 C1 C6 117.3(6) . . ? C3 C2 C1 121.0(6) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 121.2(7) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 120.1(7) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.7(6) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C6 C5 120.8(6) . . ? C7 C6 C1 119.5(6) . . ? C5 C6 C1 119.7(6) . . ? C6 C7 C8 121.1(6) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C7 C8 C13 120.2(6) . . ? C7 C8 C9 120.3(6) . . ? C13 C8 C9 119.5(6) . . ? C10 C9 C8 121.5(6) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C9 C10 C11 119.8(7) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 121.0(7) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 121.5(6) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? C14 C13 C12 124.3(6) . . ? C14 C13 C8 118.9(6) . . ? C12 C13 C8 116.8(6) . . ? C13 C14 C1 120.7(5) . . ? C13 C14 C15 121.1(6) . . ? C1 C14 C15 118.2(6) . . ? N1 C15 C14 111.9(5) . . ? N1 C15 H15A 109.2 . . ? C14 C15 H15A 109.2 . . ? N1 C15 H15B 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? N1 C16 N2 106.6(5) . . ? N1 C16 I2 127.3(4) . . ? N2 C16 I2 126.0(4) . . ? C18 C17 N2 107.3(6) . . ? C18 C17 H17 126.3 . . ? N2 C17 H17 126.3 . . ? C17 C18 N1 107.1(6) . . ? C17 C18 H18 126.5 . . ? N1 C18 H18 126.5 . . ? N2 C19 C20 110.1(6) . . ? N2 C19 H19A 109.6 . . ? C20 C19 H19A 109.6 . . ? N2 C19 H19B 109.6 . . ? C20 C19 H19B 109.6 . . ? H19A C19 H19B 108.2 . . ? 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 . . ? 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 C14 C1 C2 C3 177.7(6) . . . . ? C6 C1 C2 C3 -1.4(9) . . . . ? C1 C2 C3 C4 -0.4(10) . . . . ? C2 C3 C4 C5 1.8(11) . . . . ? C3 C4 C5 C6 -1.2(11) . . . . ? C4 C5 C6 C7 178.4(7) . . . . ? C4 C5 C6 C1 -0.7(10) . . . . ? C14 C1 C6 C7 3.7(9) . . . . ? C2 C1 C6 C7 -177.2(6) . . . . ? C14 C1 C6 C5 -177.2(6) . . . . ? C2 C1 C6 C5 1.9(9) . . . . ? C5 C6 C7 C8 179.7(6) . . . . ? C1 C6 C7 C8 -1.2(9) . . . . ? C6 C7 C8 C13 -1.1(10) . . . . ? C6 C7 C8 C9 178.3(6) . . . . ? C7 C8 C9 C10 -179.4(7) . . . . ? C13 C8 C9 C10 0.1(10) . . . . ? C8 C9 C10 C11 -0.9(10) . . . . ? C9 C10 C11 C12 0.9(11) . . . . ? C10 C11 C12 C13 0.0(10) . . . . ? C11 C12 C13 C14 178.5(6) . . . . ? C11 C12 C13 C8 -0.8(9) . . . . ? C7 C8 C13 C14 0.9(9) . . . . ? C9 C8 C13 C14 -178.5(6) . . . . ? C7 C8 C13 C12 -179.7(6) . . . . ? C9 C8 C13 C12 0.8(9) . . . . ? C12 C13 C14 C1 -177.6(6) . . . . ? C8 C13 C14 C1 1.6(9) . . . . ? C12 C13 C14 C15 1.0(10) . . . . ? C8 C13 C14 C15 -179.7(6) . . . . ? C2 C1 C14 C13 177.0(6) . . . . ? C6 C1 C14 C13 -3.9(9) . . . . ? C2 C1 C14 C15 -1.7(9) . . . . ? C6 C1 C14 C15 177.4(5) . . . . ? C16 N1 C15 C14 160.9(6) . . . . ? C18 N1 C15 C14 -22.3(9) . . . . ? C13 C14 C15 N1 118.4(6) . . . . ? C1 C14 C15 N1 -62.9(8) . . . . ? C18 N1 C16 N2 0.9(7) . . . . ? C15 N1 C16 N2 178.1(6) . . . . ? C18 N1 C16 I2 -174.7(5) . . . . ? C15 N1 C16 I2 2.5(9) . . . . ? C17 N2 C16 N1 0.2(7) . . . . ? C19 N2 C16 N1 178.4(6) . . . . ? C17 N2 C16 I2 175.9(5) . . . . ? C19 N2 C16 I2 -5.9(9) . . . . ? C16 N2 C17 C18 -1.2(8) . . . . ? C19 N2 C17 C18 -179.4(6) . . . . ? N2 C17 C18 N1 1.7(8) . . . . ? C16 N1 C18 C17 -1.6(8) . . . . ? C15 N1 C18 C17 -178.8(6) . . . . ? C16 N2 C19 C20 -79.3(8) . . . . ? C17 N2 C19 C20 98.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.880 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 3.775 _refine_diff_density_min -2.434 _refine_diff_density_rms 0.304 #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_mc09 _database_code_depnum_ccdc_archive 'CCDC 828714' #TrackingRef '1-Br-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 I N2 1+, C H Cl3, Br 1-' _chemical_formula_sum 'C21 H19 Br Cl3 I N2' _chemical_formula_weight 612.54 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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_space_group_name_Hall '-P 2ybc' 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 7.0749(6) _cell_length_b 12.5777(15) _cell_length_c 26.548(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.531(12) _cell_angle_gamma 90.00 _cell_volume 2362.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9910 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.81 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.722 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 3.396 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.2463 _exptl_absorpt_correction_T_max 0.3171 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 23152 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 33.48 _reflns_number_total 6948 _reflns_number_gt 5282 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 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 'w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+2.1808P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6948 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0989 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.19085(3) 0.666643(16) 0.290485(7) 0.04687(7) Uani 1 1 d . . . Br2 Br 0.06748(5) 0.97036(3) 0.225752(12) 0.05220(10) Uani 1 1 d . . . N1 N 0.3261(3) 0.8795(2) 0.33419(9) 0.0392(5) Uani 1 1 d . . . N2 N 0.5197(4) 0.8259(2) 0.27730(10) 0.0456(6) Uani 1 1 d . . . C1 C 0.2418(4) 0.9213(3) 0.45652(12) 0.0499(7) Uani 1 1 d . . . C2 C 0.2978(5) 0.8143(4) 0.46412(17) 0.0665(10) Uani 1 1 d . . . H2 H 0.2976 0.7671 0.4372 0.080 Uiso 1 1 calc R . . C3 C 0.3524(6) 0.7802(5) 0.5112(2) 0.0868(16) Uani 1 1 d . . . H3 H 0.3884 0.7097 0.5159 0.104 Uiso 1 1 calc R . . C4 C 0.3542(6) 0.8513(5) 0.55262(18) 0.0869(16) Uani 1 1 d . . . H4 H 0.3892 0.8267 0.5844 0.104 Uiso 1 1 calc R . . C5 C 0.3064(5) 0.9529(5) 0.54653(15) 0.0756(13) Uani 1 1 d . . . H5 H 0.3096 0.9981 0.5742 0.091 Uiso 1 1 calc R . . C6 C 0.2508(4) 0.9939(4) 0.49900(12) 0.0575(9) Uani 1 1 d . . . C7 C 0.2052(5) 1.0987(4) 0.49235(13) 0.0606(10) Uani 1 1 d . . . H7 H 0.2126 1.1441 0.5199 0.073 Uiso 1 1 calc R . . C8 C 0.1487(4) 1.1400(3) 0.44631(13) 0.0524(8) Uani 1 1 d . . . C9 C 0.1051(6) 1.2514(3) 0.43921(19) 0.0720(12) Uani 1 1 d . . . H9 H 0.1185 1.2981 0.4662 0.086 Uiso 1 1 calc R . . C10 C 0.0451(6) 1.2889(4) 0.39390(19) 0.0757(12) Uani 1 1 d . . . H10 H 0.0187 1.3608 0.3900 0.091 Uiso 1 1 calc R . . C11 C 0.0232(6) 1.2206(3) 0.35367(17) 0.0676(10) Uani 1 1 d . . . H11 H -0.0209 1.2471 0.3230 0.081 Uiso 1 1 calc R . . C12 C 0.0648(5) 1.1148(3) 0.35774(13) 0.0538(8) Uani 1 1 d . . . H12 H 0.0503 1.0712 0.3297 0.065 Uiso 1 1 calc R . . C13 C 0.1304(4) 1.0695(3) 0.40433(11) 0.0443(6) Uani 1 1 d . . . C14 C 0.1775(4) 0.9617(3) 0.40979(11) 0.0420(6) Uani 1 1 d . . . C15 C 0.1530(4) 0.8878(3) 0.36535(11) 0.0450(7) Uani 1 1 d . . . H15A H 0.1197 0.8176 0.3775 0.054 Uiso 1 1 calc R . . H15B H 0.0494 0.9131 0.3444 0.054 Uiso 1 1 calc R . . C16 C 0.3591(4) 0.8019(2) 0.30120(11) 0.0407(6) Uani 1 1 d . . . C17 C 0.5876(4) 0.9214(3) 0.29514(12) 0.0492(7) Uani 1 1 d . . . H17 H 0.6963 0.9563 0.2846 0.059 Uiso 1 1 calc R . . C18 C 0.4666(4) 0.9549(3) 0.33082(12) 0.0465(7) Uani 1 1 d . . . H18 H 0.4763 1.0171 0.3496 0.056 Uiso 1 1 calc R . . C19 C 0.6070(5) 0.7640(3) 0.23620(13) 0.0601(9) Uani 1 1 d . . . H19A H 0.5870 0.6888 0.2420 0.072 Uiso 1 1 calc R . . H19B H 0.7421 0.7770 0.2360 0.072 Uiso 1 1 calc R . . C20 C 0.5237(7) 0.7943(6) 0.18659(16) 0.1002(19) Uani 1 1 d . . . H20A H 0.3896 0.7827 0.1870 0.150 Uiso 1 1 calc R . . H20B H 0.5790 0.7517 0.1606 0.150 Uiso 1 1 calc R . . H20C H 0.5487 0.8681 0.1801 0.150 Uiso 1 1 calc R . . C21 C 0.7586(8) 0.5770(4) 0.39502(18) 0.0881(14) Uani 1 1 d . . . H21 H 0.7954 0.5410 0.3639 0.106 Uiso 1 1 calc R . . Cl1 Cl 0.7122(2) 0.71019(13) 0.38181(6) 0.1030(4) Uani 1 1 d . . . Cl2 Cl 0.9462(4) 0.57192(18) 0.43758(8) 0.1664(11) Uani 1 1 d . . . Cl3 Cl 0.5592(5) 0.5166(2) 0.41835(12) 0.1968(13) 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 I1 0.05280(12) 0.04139(12) 0.04649(12) -0.00701(8) 0.00414(8) -0.00159(8) Br2 0.0653(2) 0.04603(18) 0.04525(17) 0.00315(13) 0.00211(14) 0.01367(14) N1 0.0417(12) 0.0409(13) 0.0350(11) -0.0015(9) 0.0044(9) -0.0025(10) N2 0.0416(13) 0.0534(15) 0.0418(13) -0.0047(11) 0.0086(10) 0.0007(11) C1 0.0358(14) 0.069(2) 0.0448(16) 0.0022(15) 0.0091(12) -0.0036(14) C2 0.053(2) 0.077(3) 0.069(2) 0.018(2) 0.0092(17) 0.0018(18) C3 0.055(2) 0.102(4) 0.103(4) 0.047(3) 0.010(2) 0.004(2) C4 0.051(2) 0.152(5) 0.058(2) 0.034(3) 0.0020(17) -0.008(3) C5 0.0470(19) 0.135(5) 0.0450(19) 0.008(2) 0.0009(15) -0.008(2) C6 0.0323(14) 0.105(3) 0.0357(15) -0.0023(17) 0.0067(11) -0.0111(16) C7 0.0432(17) 0.088(3) 0.0513(19) -0.0263(19) 0.0107(14) -0.0108(17) C8 0.0405(15) 0.064(2) 0.0526(18) -0.0190(16) 0.0115(13) -0.0073(14) C9 0.063(2) 0.062(2) 0.091(3) -0.037(2) 0.023(2) -0.0058(19) C10 0.076(3) 0.059(2) 0.092(3) 0.000(2) 0.022(2) 0.005(2) C11 0.062(2) 0.067(2) 0.074(3) 0.012(2) 0.0196(19) 0.0074(18) C12 0.0532(18) 0.057(2) 0.0510(18) -0.0008(15) 0.0100(14) -0.0032(15) C13 0.0373(14) 0.0535(17) 0.0422(15) -0.0084(13) 0.0093(11) -0.0053(12) C14 0.0380(14) 0.0527(17) 0.0355(14) -0.0070(12) 0.0086(11) -0.0052(12) C15 0.0407(14) 0.0507(17) 0.0439(15) -0.0085(13) 0.0107(12) -0.0074(12) C16 0.0408(14) 0.0430(15) 0.0385(14) -0.0018(12) 0.0029(11) 0.0017(12) C17 0.0438(16) 0.0540(19) 0.0501(17) 0.0007(14) 0.0066(13) -0.0073(14) C18 0.0483(16) 0.0453(16) 0.0462(16) -0.0041(13) 0.0051(13) -0.0105(13) C19 0.0484(18) 0.076(2) 0.056(2) -0.0167(18) 0.0147(15) 0.0057(17) C20 0.077(3) 0.176(6) 0.048(2) -0.027(3) 0.008(2) 0.033(3) C21 0.120(4) 0.081(3) 0.063(3) -0.016(2) -0.002(3) 0.020(3) Cl1 0.1014(10) 0.0982(10) 0.1094(10) 0.0129(8) 0.0024(8) 0.0234(8) Cl2 0.232(2) 0.1503(17) 0.1156(13) -0.0516(12) -0.0837(15) 0.1006(17) Cl3 0.246(3) 0.1376(19) 0.209(3) 0.0016(17) 0.089(2) -0.055(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 I1 C16 2.094(3) . ? N1 C16 1.333(4) . ? N1 C18 1.377(4) . ? N1 C15 1.488(4) . ? N2 C16 1.341(4) . ? N2 C17 1.376(4) . ? N2 C19 1.480(4) . ? C1 C14 1.412(5) . ? C1 C2 1.417(6) . ? C1 C6 1.452(5) . ? C2 C3 1.373(6) . ? C2 H2 0.9300 . ? C3 C4 1.418(8) . ? C3 H3 0.9300 . ? C4 C5 1.332(7) . ? C4 H4 0.9300 . ? C5 C6 1.415(5) . ? C5 H5 0.9300 . ? C6 C7 1.368(6) . ? C7 C8 1.384(6) . ? C7 H7 0.9300 . ? C8 C13 1.430(4) . ? C8 C9 1.446(6) . ? C9 C10 1.356(7) . ? C9 H9 0.9300 . ? C10 C11 1.378(6) . ? C10 H10 0.9300 . ? C11 C12 1.367(5) . ? C11 H11 0.9300 . ? C12 C13 1.435(5) . ? C12 H12 0.9300 . ? C13 C14 1.403(5) . ? C14 C15 1.511(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C17 C18 1.350(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.487(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 Cl3 1.722(6) . ? C21 Cl2 1.737(6) . ? C21 Cl1 1.742(5) . ? C21 H21 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 C16 N1 C18 109.3(2) . . ? C16 N1 C15 124.5(2) . . ? C18 N1 C15 125.9(2) . . ? C16 N2 C17 109.2(2) . . ? C16 N2 C19 126.2(3) . . ? C17 N2 C19 124.5(3) . . ? C14 C1 C2 123.7(3) . . ? C14 C1 C6 117.8(3) . . ? C2 C1 C6 118.5(3) . . ? C3 C2 C1 120.2(5) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 120.6(5) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 120.7(4) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 121.8(5) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C7 C6 C5 122.0(4) . . ? C7 C6 C1 119.8(3) . . ? C5 C6 C1 118.2(4) . . ? C6 C7 C8 122.8(3) . . ? C6 C7 H7 118.6 . . ? C8 C7 H7 118.6 . . ? C7 C8 C13 118.6(4) . . ? C7 C8 C9 122.6(3) . . ? C13 C8 C9 118.8(4) . . ? C10 C9 C8 121.1(4) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 120.2(4) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 121.5(4) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C11 C12 C13 121.5(3) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C14 C13 C8 119.9(3) . . ? C14 C13 C12 123.2(3) . . ? C8 C13 C12 116.9(3) . . ? C13 C14 C1 120.9(3) . . ? C13 C14 C15 119.2(3) . . ? C1 C14 C15 119.9(3) . . ? N1 C15 C14 112.8(2) . . ? N1 C15 H15A 109.0 . . ? C14 C15 H15A 109.0 . . ? N1 C15 H15B 109.0 . . ? C14 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? N1 C16 N2 107.4(3) . . ? N1 C16 I1 125.5(2) . . ? N2 C16 I1 127.0(2) . . ? C18 C17 N2 107.0(3) . . ? C18 C17 H17 126.5 . . ? N2 C17 H17 126.5 . . ? C17 C18 N1 107.1(3) . . ? C17 C18 H18 126.5 . . ? N1 C18 H18 126.5 . . ? N2 C19 C20 110.7(3) . . ? N2 C19 H19A 109.5 . . ? C20 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 108.1 . . ? 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 . . ? Cl3 C21 Cl2 111.9(3) . . ? Cl3 C21 Cl1 110.1(3) . . ? Cl2 C21 Cl1 107.9(3) . . ? Cl3 C21 H21 109.0 . . ? Cl2 C21 H21 109.0 . . ? Cl1 C21 H21 109.0 . . ? 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 C14 C1 C2 C3 -177.7(3) . . . . ? C6 C1 C2 C3 2.3(5) . . . . ? C1 C2 C3 C4 -0.3(6) . . . . ? C2 C3 C4 C5 -1.2(7) . . . . ? C3 C4 C5 C6 0.5(6) . . . . ? C4 C5 C6 C7 -178.6(4) . . . . ? C4 C5 C6 C1 1.6(5) . . . . ? C14 C1 C6 C7 -2.7(4) . . . . ? C2 C1 C6 C7 177.3(3) . . . . ? C14 C1 C6 C5 177.0(3) . . . . ? C2 C1 C6 C5 -3.0(4) . . . . ? C5 C6 C7 C8 -179.3(3) . . . . ? C1 C6 C7 C8 0.4(5) . . . . ? C6 C7 C8 C13 2.4(5) . . . . ? C6 C7 C8 C9 -178.5(3) . . . . ? C7 C8 C9 C10 -178.2(4) . . . . ? C13 C8 C9 C10 1.0(5) . . . . ? C8 C9 C10 C11 0.5(6) . . . . ? C9 C10 C11 C12 -1.5(6) . . . . ? C10 C11 C12 C13 1.0(6) . . . . ? C7 C8 C13 C14 -2.8(4) . . . . ? C9 C8 C13 C14 178.0(3) . . . . ? C7 C8 C13 C12 177.8(3) . . . . ? C9 C8 C13 C12 -1.4(4) . . . . ? C11 C12 C13 C14 -178.9(3) . . . . ? C11 C12 C13 C8 0.5(5) . . . . ? C8 C13 C14 C1 0.5(4) . . . . ? C12 C13 C14 C1 179.9(3) . . . . ? C8 C13 C14 C15 178.6(3) . . . . ? C12 C13 C14 C15 -2.1(4) . . . . ? C2 C1 C14 C13 -177.8(3) . . . . ? C6 C1 C14 C13 2.2(4) . . . . ? C2 C1 C14 C15 4.2(4) . . . . ? C6 C1 C14 C15 -175.8(3) . . . . ? C16 N1 C15 C14 162.4(3) . . . . ? C18 N1 C15 C14 -24.7(4) . . . . ? C13 C14 C15 N1 91.2(3) . . . . ? C1 C14 C15 N1 -90.7(3) . . . . ? C18 N1 C16 N2 0.8(3) . . . . ? C15 N1 C16 N2 174.7(3) . . . . ? C18 N1 C16 I1 179.7(2) . . . . ? C15 N1 C16 I1 -6.4(4) . . . . ? C17 N2 C16 N1 -0.9(4) . . . . ? C19 N2 C16 N1 -177.7(3) . . . . ? C17 N2 C16 I1 -179.8(2) . . . . ? C19 N2 C16 I1 3.4(5) . . . . ? C16 N2 C17 C18 0.6(4) . . . . ? C19 N2 C17 C18 177.5(3) . . . . ? N2 C17 C18 N1 -0.2(4) . . . . ? C16 N1 C18 C17 -0.4(4) . . . . ? C15 N1 C18 C17 -174.2(3) . . . . ? C16 N2 C19 C20 85.2(5) . . . . ? C17 N2 C19 C20 -91.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.752 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.016 _refine_diff_density_min -1.157 _refine_diff_density_rms 0.080 # Attachment '1-Cl-CIF.txt' data_mc01 _database_code_depnum_ccdc_archive 'CCDC 828715' #TrackingRef '1-Cl-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 N2 I 1+, H2 O, Cl 1-' _chemical_formula_sum 'C20 H20 Cl I N2 O' _chemical_formula_weight 466.73 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 12.3454(12) _cell_length_b 10.2075(10) _cell_length_c 15.1939(15) _cell_angle_alpha 90.00 _cell_angle_beta 91.473(10) _cell_angle_gamma 90.00 _cell_volume 1914.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 9783 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 34.15 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 1.823 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.6581 _exptl_absorpt_correction_T_max 0.7057 _exptl_special_details ; Bruker KRYOFLEX low temperature device. ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 31778 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 34.36 _reflns_number_total 6582 _reflns_number_gt 5842 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 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. H atoms of antracene, ethyl, and water were refined with soft restraints on the distance X-H ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+0.9294P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6582 _refine_ls_number_parameters 306 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0277 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0710 _refine_ls_wR_factor_gt 0.0692 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.615841(8) -0.124312(10) 0.820084(7) 0.01791(4) Uani 1 1 d . . . N1 N 0.75044(11) 0.09259(14) 0.73803(9) 0.0151(2) Uani 1 1 d . . . N2 N 0.62387(10) 0.17695(15) 0.81663(9) 0.0166(3) Uani 1 1 d . . . C1 C 0.66809(12) 0.06400(16) 0.79038(10) 0.0158(3) Uani 1 1 d . . . C2 C 0.67825(13) 0.27988(17) 0.77923(11) 0.0185(3) Uani 1 1 d . . . H2 H 0.6521(19) 0.362(2) 0.7948(15) 0.014(5) Uiso 1 1 d . . . C3 C 0.75685(13) 0.22751(17) 0.73006(11) 0.0179(3) Uani 1 1 d . . . H3 H 0.806(2) 0.272(3) 0.6969(17) 0.035(7) Uiso 1 1 d . . . C4 C 0.81865(13) -0.00308(17) 0.69175(11) 0.0164(3) Uani 1 1 d . . . H4A H 0.7806(19) -0.026(2) 0.6393(16) 0.029(6) Uiso 1 1 d . . . H4B H 0.8206(16) -0.079(2) 0.7265(13) 0.012(5) Uiso 1 1 d . . . C5 C 0.93141(12) 0.04892(16) 0.67820(10) 0.0141(3) Uani 1 1 d . . . C6 C 1.01141(12) 0.03325(15) 0.74557(10) 0.0139(3) Uani 1 1 d . . . C7 C 0.99062(14) -0.02640(16) 0.82860(11) 0.0180(3) Uani 1 1 d D . . H7 H 0.9200(9) -0.056(2) 0.8414(13) 0.013(5) Uiso 1 1 d D . . C8 C 1.07041(15) -0.03761(18) 0.89231(11) 0.0214(3) Uani 1 1 d D . . H8 H 1.056(2) -0.080(2) 0.9457(10) 0.033(6) Uiso 1 1 d D . . C9 C 1.17675(15) 0.01032(18) 0.87753(12) 0.0222(3) Uani 1 1 d D . . H9 H 1.2314(14) 0.007(2) 0.9220(12) 0.026(6) Uiso 1 1 d D . . C10 C 1.20035(13) 0.06532(17) 0.79939(11) 0.0193(3) Uani 1 1 d D . . H10 H 1.2706(12) 0.097(3) 0.7906(19) 0.044(8) Uiso 1 1 d D . . C11 C 1.11964(12) 0.07799(16) 0.73051(10) 0.0147(3) Uani 1 1 d . . . C12 C 1.14497(13) 0.13177(15) 0.64918(11) 0.0159(3) Uani 1 1 d D . . H12 H 1.2178(9) 0.152(2) 0.6376(15) 0.020(5) Uiso 1 1 d D . . C13 C 1.06608(13) 0.14909(16) 0.58303(10) 0.0148(3) Uani 1 1 d . . . C14 C 1.09344(14) 0.20429(17) 0.49992(11) 0.0194(3) Uani 1 1 d D . . H14 H 1.1660(9) 0.228(2) 0.4906(14) 0.023(5) Uiso 1 1 d D . . C15 C 1.01653(16) 0.22069(17) 0.43536(11) 0.0215(3) Uani 1 1 d D . . H15 H 1.037(2) 0.258(2) 0.3819(10) 0.041(7) Uiso 1 1 d D . . C16 C 0.90763(15) 0.18449(18) 0.45033(11) 0.0221(3) Uani 1 1 d D . . H16 H 0.8499(16) 0.184(3) 0.4092(14) 0.043(7) Uiso 1 1 d D . . C17 C 0.87817(14) 0.13053(16) 0.52810(12) 0.0185(3) Uani 1 1 d D . . H17 H 0.8050(9) 0.107(2) 0.5365(15) 0.019(6) Uiso 1 1 d D . . C18 C 0.95648(12) 0.10884(15) 0.59798(11) 0.0144(3) Uani 1 1 d . . . C19 C 0.53531(14) 0.1918(2) 0.87828(12) 0.0231(3) Uani 1 1 d D . . H19A H 0.4904(19) 0.1187(17) 0.8626(18) 0.030(7) Uiso 1 1 d D . . H19B H 0.502(2) 0.2740(17) 0.8642(17) 0.044(7) Uiso 1 1 d D . . C20 C 0.5772(2) 0.1904(3) 0.97218(14) 0.0382(5) Uani 1 1 d D . . H20A H 0.603(2) 0.1044(15) 0.9856(18) 0.035(7) Uiso 1 1 d D . . H20B H 0.5219(18) 0.205(3) 1.0141(15) 0.054(9) Uiso 1 1 d D . . H20C H 0.6283(19) 0.260(2) 0.9782(19) 0.049(8) Uiso 1 1 d D . . Cl1 Cl 0.44637(3) 0.09247(4) 0.65225(3) 0.02043(8) Uani 1 1 d . . . O1 O 0.63585(11) 0.9495(2) 0.54726(11) 0.0375(4) Uani 1 1 d D . . H1A H 0.619(2) 0.929(3) 0.4966(9) 0.048(8) Uiso 1 1 d D . . H1B H 0.5911(19) 0.996(3) 0.5706(18) 0.053(9) Uiso 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 I1 0.01633(5) 0.01505(7) 0.02256(6) 0.00315(4) 0.00453(4) -0.00014(3) N1 0.0147(5) 0.0117(6) 0.0189(6) 0.0004(5) 0.0034(5) 0.0000(5) N2 0.0148(5) 0.0149(7) 0.0204(6) 0.0010(5) 0.0040(5) 0.0017(5) C1 0.0141(6) 0.0143(8) 0.0191(7) 0.0017(6) 0.0025(5) 0.0005(5) C2 0.0188(6) 0.0128(8) 0.0241(8) 0.0010(6) 0.0026(6) 0.0003(6) C3 0.0189(6) 0.0128(7) 0.0222(7) 0.0009(6) 0.0036(6) -0.0013(6) C4 0.0153(6) 0.0134(7) 0.0206(7) -0.0022(6) 0.0045(5) -0.0008(5) C5 0.0141(6) 0.0107(7) 0.0178(7) -0.0010(5) 0.0027(5) -0.0006(5) C6 0.0166(6) 0.0095(7) 0.0157(6) -0.0007(5) 0.0037(5) 0.0008(5) C7 0.0233(7) 0.0130(7) 0.0181(7) 0.0013(6) 0.0056(6) 0.0014(6) C8 0.0315(8) 0.0153(8) 0.0175(7) 0.0022(6) 0.0031(6) 0.0056(6) C9 0.0264(8) 0.0182(8) 0.0217(8) -0.0021(6) -0.0046(6) 0.0059(6) C10 0.0179(7) 0.0160(8) 0.0237(8) -0.0030(6) -0.0016(6) 0.0027(6) C11 0.0154(6) 0.0113(7) 0.0176(7) -0.0013(5) 0.0019(5) 0.0006(5) C12 0.0146(6) 0.0138(7) 0.0195(7) -0.0008(5) 0.0041(5) -0.0018(5) C13 0.0176(6) 0.0097(7) 0.0173(7) -0.0014(5) 0.0049(5) -0.0009(5) C14 0.0255(7) 0.0137(7) 0.0193(7) 0.0001(6) 0.0074(6) -0.0014(6) C15 0.0360(9) 0.0128(8) 0.0158(7) 0.0003(6) 0.0051(6) 0.0015(7) C16 0.0326(8) 0.0164(8) 0.0173(7) -0.0018(6) -0.0030(6) 0.0030(7) C17 0.0205(7) 0.0156(8) 0.0194(7) -0.0022(6) -0.0021(6) 0.0000(6) C18 0.0157(6) 0.0109(7) 0.0166(7) -0.0016(5) 0.0018(5) 0.0005(5) C19 0.0186(7) 0.0236(9) 0.0276(9) 0.0000(7) 0.0094(6) 0.0043(6) C20 0.0396(11) 0.0501(15) 0.0252(9) -0.0018(9) 0.0104(8) 0.0096(11) Cl1 0.02051(16) 0.01675(18) 0.02420(19) -0.00248(15) 0.00373(14) 0.00042(14) O1 0.0187(6) 0.0607(12) 0.0329(8) -0.0130(8) -0.0018(5) 0.0061(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.0808(17) . ? N1 C1 1.339(2) . ? N1 C3 1.385(2) . ? N1 C4 1.479(2) . ? N2 C1 1.341(2) . ? N2 C2 1.377(2) . ? N2 C19 1.466(2) . ? C2 C3 1.350(2) . ? C2 H2 0.93(2) . ? C3 H3 0.92(3) . ? C4 C5 1.509(2) . ? C4 H4A 0.95(2) . ? C4 H4B 0.94(2) . ? C5 C18 1.405(2) . ? C5 C6 1.413(2) . ? C6 C7 1.430(2) . ? C6 C11 1.436(2) . ? C7 C8 1.368(2) . ? C7 H7 0.947(9) . ? C8 C9 1.424(3) . ? C8 H8 0.941(10) . ? C9 C10 1.352(3) . ? C9 H9 0.944(9) . ? C10 C11 1.432(2) . ? C10 H10 0.938(10) . ? C11 C12 1.395(2) . ? C12 C13 1.393(2) . ? C12 H12 0.944(9) . ? C13 C14 1.431(2) . ? C13 C18 1.438(2) . ? C14 C15 1.358(3) . ? C14 H14 0.942(9) . ? C15 C16 1.418(3) . ? C15 H15 0.939(10) . ? C16 C17 1.362(3) . ? C16 H16 0.935(10) . ? C17 C18 1.435(2) . ? C17 H17 0.947(9) . ? C19 C20 1.505(3) . ? C19 H19A 0.956(13) . ? C19 H19B 0.958(13) . ? C20 H20A 0.956(13) . ? C20 H20B 0.957(13) . ? C20 H20C 0.953(13) . ? O1 H1A 0.818(10) . ? O1 H1B 0.814(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C3 108.34(14) . . ? C1 N1 C4 126.07(14) . . ? C3 N1 C4 125.49(14) . . ? C1 N2 C2 109.07(13) . . ? C1 N2 C19 126.52(15) . . ? C2 N2 C19 124.36(15) . . ? N1 C1 N2 108.09(14) . . ? N1 C1 I1 125.06(12) . . ? N2 C1 I1 126.80(12) . . ? C3 C2 N2 106.92(15) . . ? C3 C2 H2 139.3(15) . . ? N2 C2 H2 113.8(15) . . ? C2 C3 N1 107.57(15) . . ? C2 C3 H3 126.9(17) . . ? N1 C3 H3 125.5(17) . . ? N1 C4 C5 111.79(14) . . ? N1 C4 H4A 106.9(15) . . ? C5 C4 H4A 114.5(15) . . ? N1 C4 H4B 106.6(13) . . ? C5 C4 H4B 110.9(12) . . ? H4A C4 H4B 105.8(19) . . ? C18 C5 C6 120.81(14) . . ? C18 C5 C4 119.73(14) . . ? C6 C5 C4 119.44(14) . . ? C5 C6 C7 123.32(14) . . ? C5 C6 C11 118.97(14) . . ? C7 C6 C11 117.71(14) . . ? C8 C7 C6 121.17(16) . . ? C8 C7 H7 118.5(12) . . ? C6 C7 H7 120.3(12) . . ? C7 C8 C9 120.63(16) . . ? C7 C8 H8 120.0(16) . . ? C9 C8 H8 119.4(15) . . ? C10 C9 C8 120.10(16) . . ? C10 C9 H9 118.6(15) . . ? C8 C9 H9 121.2(15) . . ? C9 C10 C11 121.18(16) . . ? C9 C10 H10 119.3(18) . . ? C11 C10 H10 119.5(18) . . ? C12 C11 C10 121.01(15) . . ? C12 C11 C6 119.81(14) . . ? C10 C11 C6 119.18(15) . . ? C13 C12 C11 121.38(14) . . ? C13 C12 H12 119.3(14) . . ? C11 C12 H12 119.2(14) . . ? C12 C13 C14 120.68(15) . . ? C12 C13 C18 119.55(15) . . ? C14 C13 C18 119.76(14) . . ? C15 C14 C13 120.62(16) . . ? C15 C14 H14 120.7(13) . . ? C13 C14 H14 118.7(13) . . ? C14 C15 C16 120.01(16) . . ? C14 C15 H15 118.6(16) . . ? C16 C15 H15 121.4(16) . . ? C17 C16 C15 121.33(16) . . ? C17 C16 H16 111.1(17) . . ? C15 C16 H16 127.2(17) . . ? C16 C17 C18 120.98(16) . . ? C16 C17 H17 119.8(14) . . ? C18 C17 H17 119.2(14) . . ? C5 C18 C17 123.35(15) . . ? C5 C18 C13 119.38(14) . . ? C17 C18 C13 117.26(15) . . ? N2 C19 C20 111.17(15) . . ? N2 C19 H19A 101.4(17) . . ? C20 C19 H19A 114.3(16) . . ? N2 C19 H19B 105.8(17) . . ? C20 C19 H19B 110.9(16) . . ? H19A C19 H19B 113(2) . . ? C19 C20 H20A 108.5(17) . . ? C19 C20 H20B 113.3(18) . . ? H20A C20 H20B 104(3) . . ? C19 C20 H20C 107.2(18) . . ? H20A C20 H20C 116(2) . . ? H20B C20 H20C 108(3) . . ? H1A O1 H1B 113(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 C3 N1 C1 N2 -1.02(17) . . . . ? C4 N1 C1 N2 -177.36(14) . . . . ? C3 N1 C1 I1 176.60(11) . . . . ? C4 N1 C1 I1 0.3(2) . . . . ? C2 N2 C1 N1 0.84(17) . . . . ? C19 N2 C1 N1 -176.54(15) . . . . ? C2 N2 C1 I1 -176.72(11) . . . . ? C19 N2 C1 I1 5.9(2) . . . . ? C1 N2 C2 C3 -0.33(18) . . . . ? C19 N2 C2 C3 177.12(15) . . . . ? N2 C2 C3 N1 -0.30(18) . . . . ? C1 N1 C3 C2 0.82(19) . . . . ? C4 N1 C3 C2 177.18(15) . . . . ? C1 N1 C4 C5 -150.99(15) . . . . ? C3 N1 C4 C5 33.3(2) . . . . ? N1 C4 C5 C18 -95.81(17) . . . . ? N1 C4 C5 C6 86.02(18) . . . . ? C18 C5 C6 C7 179.73(15) . . . . ? C4 C5 C6 C7 -2.1(2) . . . . ? C18 C5 C6 C11 -0.8(2) . . . . ? C4 C5 C6 C11 177.32(14) . . . . ? C5 C6 C7 C8 -179.01(16) . . . . ? C11 C6 C7 C8 1.5(2) . . . . ? C6 C7 C8 C9 0.1(3) . . . . ? C7 C8 C9 C10 -1.3(3) . . . . ? C8 C9 C10 C11 0.7(3) . . . . ? C9 C10 C11 C12 -178.36(17) . . . . ? C9 C10 C11 C6 1.0(3) . . . . ? C5 C6 C11 C12 -2.2(2) . . . . ? C7 C6 C11 C12 177.30(15) . . . . ? C5 C6 C11 C10 178.44(15) . . . . ? C7 C6 C11 C10 -2.1(2) . . . . ? C10 C11 C12 C13 -177.50(15) . . . . ? C6 C11 C12 C13 3.1(2) . . . . ? C11 C12 C13 C14 -179.93(15) . . . . ? C11 C12 C13 C18 -1.1(2) . . . . ? C12 C13 C14 C15 179.77(16) . . . . ? C18 C13 C14 C15 0.9(2) . . . . ? C13 C14 C15 C16 0.8(3) . . . . ? C14 C15 C16 C17 -1.4(3) . . . . ? C15 C16 C17 C18 0.3(3) . . . . ? C6 C5 C18 C17 -178.34(15) . . . . ? C4 C5 C18 C17 3.5(2) . . . . ? C6 C5 C18 C13 2.9(2) . . . . ? C4 C5 C18 C13 -175.27(14) . . . . ? C16 C17 C18 C5 -177.44(16) . . . . ? C16 C17 C18 C13 1.4(2) . . . . ? C12 C13 C18 C5 -2.0(2) . . . . ? C14 C13 C18 C5 176.93(15) . . . . ? C12 C13 C18 C17 179.18(15) . . . . ? C14 C13 C18 C17 -1.9(2) . . . . ? C1 N2 C19 C20 84.4(2) . . . . ? C2 N2 C19 C20 -92.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.820 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.224 _refine_diff_density_min -0.577 _refine_diff_density_rms 0.100 # Attachment '1-H2PO4-CIF.txt' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-05-11 at 15:48:52 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : C:\Program Files (x86)\wingx\files\archive.reqdat # CIF files read : kra004 dreduc sadabs sortav struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_kra004 _database_code_depnum_ccdc_archive 'CCDC 828717' #TrackingRef '1-H2PO4-CIF.txt' _audit_creation_date 2011-05-11T15:48:52-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H18 I N2, C3 H7 N O, H2 O4 P' _chemical_formula_sum 'C23 H27 I N3 O5 P' _chemical_formula_weight 583.35 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_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 16.8192(13) _cell_length_b 16.3863(13) _cell_length_c 8.5845(6) _cell_angle_alpha 90 _cell_angle_beta 90.086(3) _cell_angle_gamma 90 _cell_volume 2365.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 7911 _cell_measurement_theta_min 2.4219 _cell_measurement_theta_max 21.0704 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.638 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.461 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction ; _exptl_absorpt_correction_T_min 0.905 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'sealed x-ray tube' _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'APEX-II CCD' _diffrn_orient_matrix_type 'x-axis to radiation source' _diffrn_orient_matrix_ub_11 -0.61962E-2 _diffrn_orient_matrix_ub_12 0.538596E-1 _diffrn_orient_matrix_ub_13 0.277607E-1 _diffrn_orient_matrix_ub_21 0.198443E-1 _diffrn_orient_matrix_ub_22 -0.276384E-1 _diffrn_orient_matrix_ub_23 0.520509E-1 _diffrn_orient_matrix_ub_31 0.114619 _diffrn_orient_matrix_ub_32 0.771275E-2 _diffrn_orient_matrix_ub_33 -0.741991E-2 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II' _diffrn_measurement_method '\f or \w oscillation scans' _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_unetI/netI 0.0999 _diffrn_reflns_number 29610 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.975 _diffrn_measured_fraction_theta_max 0.973 _reflns_number_total 29610 _reflns_number_gt 22598 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 software' _computing_cell_refinement 'SAINT V7.56A integration software' _computing_data_reduction 'SORTAV (Blessing, 1995)' _computing_structure_solution 'SUPERFLIP (L. Palatinus et al, J. Appl. Cryst, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(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^)+(0.0377P)^2^+24.7575P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 29610 _refine_ls_number_parameters 204 _refine_ls_number_restraints 175 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1559 _refine_ls_wR_factor_gt 0.1398 _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 3.375 _refine_diff_density_min -2.143 _refine_diff_density_rms 0.207 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 I1 I 0.284755(16) -0.040310(14) 0.25894(5) 0.01990(7) Uani 1 1 d U . . C2 C 0.2402(2) 0.0790(2) 0.2508(8) 0.0149(9) Uani 1 1 d U . . N3 N 0.2807(2) 0.14662(19) 0.2179(5) 0.0276(11) Uani 1 1 d U . . C4 C 0.3651(3) 0.1508(3) 0.1660(6) 0.0308(13) Uani 1 1 d U . . H4A H 0.393 0.1004 0.199 0.037 Uiso 1 1 calc R . . H4B H 0.3914 0.1976 0.2178 0.037 Uiso 1 1 calc R . . C5 C 0.3731(4) 0.1602(4) -0.0099(6) 0.0461(16) Uani 1 1 d U . . H5A H 0.3439 0.1162 -0.0621 0.069 Uiso 1 1 calc R . . H5B H 0.4293 0.1575 -0.0389 0.069 Uiso 1 1 calc R . . H5C H 0.3511 0.213 -0.0419 0.069 Uiso 1 1 calc R . . C6 C 0.2320(2) 0.2129(2) 0.2258(7) 0.0242(12) Uani 1 1 d U . . H6 H 0.2465 0.268 0.2066 0.029 Uiso 1 1 calc R . . C7 C 0.1606(2) 0.1860(2) 0.2653(8) 0.0291(12) Uani 1 1 d U . . H7 H 0.1141 0.2183 0.2779 0.035 Uiso 1 1 calc R . . N8 N 0.1658(2) 0.10284(19) 0.2847(6) 0.0302(13) Uani 1 1 d U . . C9 C 0.1002(3) 0.0474(3) 0.3367(6) 0.0336(13) Uani 1 1 d U . . H9A H 0.1234 0.0017 0.397 0.04 Uiso 1 1 calc R . . H9B H 0.0736 0.0241 0.2438 0.04 Uiso 1 1 calc R . . C10 C 0.0379(3) 0.0909(3) 0.4374(7) 0.0333(14) Uani 1 1 d U . . C17 C -0.0759(3) 0.1651(3) 0.6200(7) 0.0459(15) Uiso 1 1 d U . . H17 H -0.115 0.1909 0.6829 0.055 Uiso 1 1 calc R . . C11 C 0.0532(2) 0.1156(3) 0.5891(4) 0.0527(7) Uiso 1 1 d GU . . C12 C 0.1266(2) 0.0932(2) 0.6501(5) 0.0527(7) Uiso 1 1 d GU . . H12 H 0.1665 0.0715 0.5836 0.063 Uiso 1 1 calc R . . C13 C 0.14176(17) 0.1027(2) 0.8083(5) 0.0527(7) Uiso 1 1 d GU . . H13 H 0.1919 0.0874 0.85 0.063 Uiso 1 1 calc R . . C14 C 0.0835(2) 0.1345(2) 0.9055(4) 0.0527(7) Uiso 1 1 d GU . . H14 H 0.0938 0.1409 1.0136 0.063 Uiso 1 1 calc R . . C15 C 0.01003(19) 0.1568(2) 0.8445(5) 0.0527(7) Uiso 1 1 d GU . . H15 H -0.0298 0.1786 0.9109 0.063 Uiso 1 1 calc R . . C16 C -0.00510(17) 0.1474(2) 0.6863(5) 0.0527(7) Uiso 1 1 d GU . . C18 C -0.0957(2) 0.1480(2) 0.4651(4) 0.0558(7) Uiso 1 1 d GU . . C19 C -0.1696(2) 0.1693(2) 0.4047(4) 0.0558(7) Uiso 1 1 d GU . . H19 H -0.2079 0.1949 0.4695 0.067 Uiso 1 1 calc R . . C20 C -0.18730(16) 0.1532(2) 0.2495(5) 0.0558(7) Uiso 1 1 d GU . . H20 H -0.2378 0.1678 0.2083 0.067 Uiso 1 1 calc R . . C21 C -0.1312(2) 0.1158(2) 0.1547(3) 0.0558(7) Uiso 1 1 d GU . . H21 H -0.1433 0.1048 0.0487 0.067 Uiso 1 1 calc R . . C22 C -0.05732(19) 0.0944(2) 0.2151(4) 0.0558(7) Uiso 1 1 d GU . . H22 H -0.019 0.0689 0.1503 0.067 Uiso 1 1 calc R . . C23 C -0.03958(18) 0.1105(2) 0.3703(5) 0.0558(7) Uiso 1 1 d GU . . P1 P 0.60419(7) 0.26872(7) 0.12169(16) 0.0234(3) Uani 1 1 d U . . O3 O 0.65647(16) 0.31278(14) 0.2398(5) 0.0265(7) Uani 1 1 d U . . O4 O 0.53797(17) 0.2218(2) 0.2179(5) 0.0398(10) Uani 1 1 d U . . H4 H 0.5551 0.2118 0.3079 0.06 Uiso 1 1 calc R . . O5 O 0.6560(2) 0.2010(2) 0.0419(4) 0.0464(10) Uani 1 1 d U . . H5 H 0.6521 0.2052 -0.0553 0.07 Uiso 1 1 calc R . . O6 O 0.5659(2) 0.32035(17) -0.0019(4) 0.0313(9) Uani 1 1 d U . . O1A O 0.31529(19) 0.12937(19) 0.5722(4) 0.0327(9) Uani 1 1 d U . . N2A N 0.4041(2) 0.0358(2) 0.6603(5) 0.0358(11) Uani 1 1 d U . . C3A C 0.3834(3) 0.1067(3) 0.5958(6) 0.0266(12) Uani 1 1 d U . . H3A H 0.425 0.1425 0.5657 0.032 Uiso 1 1 calc R . . C4A C 0.4858(3) 0.0161(4) 0.7039(13) 0.097(4) Uani 1 1 d U . . H4A1 H 0.5225 0.0506 0.6445 0.146 Uiso 1 1 calc R . . H4A2 H 0.4965 -0.0414 0.6809 0.146 Uiso 1 1 calc R . . H4A3 H 0.4932 0.0261 0.8155 0.146 Uiso 1 1 calc R . . C5A C 0.3454(3) -0.0230(3) 0.7124(8) 0.0505(19) Uani 1 1 d U . . H5A1 H 0.293 -0.0078 0.6717 0.076 Uiso 1 1 calc R . . H5A2 H 0.3439 -0.0236 0.8265 0.076 Uiso 1 1 calc R . . H5A3 H 0.3597 -0.0774 0.6741 0.076 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.01891(12) 0.01298(11) 0.02782(13) -0.00019(18) 0.0049(2) 0.00397(13) C2 0.0128(18) 0.0111(17) 0.021(2) 0.000(3) 0.011(3) 0.0034(14) N3 0.0203(18) 0.0094(16) 0.053(3) -0.0023(17) 0.007(3) -0.0002(16) C4 0.016(2) 0.023(3) 0.054(4) 0.004(2) 0.005(2) -0.002(2) C5 0.046(4) 0.054(4) 0.039(4) 0.001(3) 0.008(3) -0.005(3) C6 0.012(2) 0.0105(19) 0.050(4) 0.007(2) 0.006(3) 0.0005(15) C7 0.024(2) 0.0081(18) 0.056(4) -0.007(3) 0.011(3) 0.0037(17) N8 0.0163(18) 0.0098(17) 0.065(4) 0.001(2) 0.009(2) 0.0005(14) C9 0.022(3) 0.013(2) 0.066(4) 0.001(2) 0.017(2) -0.006(2) C10 0.026(3) 0.006(2) 0.069(4) 0.001(2) 0.012(3) -0.001(2) P1 0.0218(7) 0.0176(7) 0.0307(8) -0.0010(6) 0.0005(6) 0.0020(6) O3 0.0355(16) 0.0193(14) 0.0248(18) -0.0001(19) -0.002(2) -0.0151(12) O4 0.0276(18) 0.045(2) 0.047(3) 0.0108(19) -0.0064(18) -0.0203(16) O5 0.065(3) 0.044(2) 0.030(2) -0.0066(18) -0.005(2) 0.029(2) O6 0.042(2) 0.0191(19) 0.033(2) 0.0058(16) -0.0067(16) 0.0121(15) O1A 0.029(2) 0.027(2) 0.042(2) -0.0039(16) -0.0031(17) 0.0145(16) N2A 0.021(2) 0.026(2) 0.059(3) -0.007(2) -0.018(2) 0.006(2) C3A 0.017(3) 0.030(3) 0.033(3) -0.019(2) -0.002(2) -0.001(2) C4A 0.032(3) 0.058(4) 0.202(12) -0.037(5) -0.024(5) 0.026(3) C5A 0.050(3) 0.030(3) 0.072(6) -0.001(3) -0.019(3) 0.004(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C2 2.095(3) . ? C2 N3 1.332(5) . ? C2 N8 1.344(4) . ? N3 C6 1.363(5) . ? N3 C4 1.490(5) . ? C4 C5 1.524(7) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 C7 1.324(5) . ? C6 H6 0.95 . ? C7 N8 1.376(5) . ? C7 H7 0.95 . ? N8 C9 1.497(5) . ? C9 C10 1.534(6) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.387(6) . ? C10 C23 1.460(6) . ? C17 C16 1.351(6) . ? C17 C18 1.398(6) . ? C17 H17 0.95 . ? C11 C12 1.39 . ? C11 C16 1.39 . ? C12 C13 1.39 . ? C12 H12 0.95 . ? C13 C14 1.39 . ? C13 H13 0.95 . ? C14 C15 1.39 . ? C14 H14 0.95 . ? C15 C16 1.39 . ? C15 H15 0.95 . ? C18 C19 1.39 . ? C18 C23 1.39 . ? C19 C20 1.39 . ? C19 H19 0.95 . ? C20 C21 1.39 . ? C20 H20 0.95 . ? C21 C22 1.39 . ? C21 H21 0.95 . ? C22 C23 1.39 . ? C22 H22 0.95 . ? P1 O6 1.501(3) . ? P1 O3 1.523(4) . ? P1 O5 1.569(3) . ? P1 O4 1.586(3) . ? O4 H4 0.84 . ? O5 H5 0.84 . ? O1A C3A 1.221(5) . ? N2A C3A 1.333(6) . ? N2A C5A 1.450(6) . ? N2A C4A 1.459(7) . ? C3A H3A 0.95 . ? C4A H4A1 0.98 . ? C4A H4A2 0.98 . ? C4A H4A3 0.98 . ? C5A H5A1 0.98 . ? C5A H5A2 0.98 . ? C5A H5A3 0.98 . ? 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 N3 C2 N8 106.3(3) . . ? N3 C2 I1 126.9(3) . . ? N8 C2 I1 126.7(3) . . ? C2 N3 C6 110.2(3) . . ? C2 N3 C4 126.2(3) . . ? C6 N3 C4 123.5(3) . . ? N3 C4 C5 112.7(4) . . ? N3 C4 H4A 109.1 . . ? C5 C4 H4A 109.1 . . ? N3 C4 H4B 109.1 . . ? C5 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 N3 107.0(3) . . ? C7 C6 H6 126.5 . . ? N3 C6 H6 126.5 . . ? C6 C7 N8 107.7(3) . . ? C6 C7 H7 126.2 . . ? N8 C7 H7 126.2 . . ? C2 N8 C7 108.7(3) . . ? C2 N8 C9 125.1(3) . . ? C7 N8 C9 126.2(3) . . ? N8 C9 C10 113.0(4) . . ? N8 C9 H9A 109 . . ? C10 C9 H9A 109 . . ? N8 C9 H9B 109 . . ? C10 C9 H9B 109 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C23 118.0(4) . . ? C11 C10 C9 122.6(5) . . ? C23 C10 C9 119.3(5) . . ? C16 C17 C18 124.5(5) . . ? C16 C17 H17 117.8 . . ? C18 C17 H17 117.8 . . ? C10 C11 C12 116.1(3) . . ? C10 C11 C16 122.9(3) . . ? C12 C11 C16 120 . . ? C13 C12 C11 120 . . ? C13 C12 H12 120 . . ? C11 C12 H12 120 . . ? C12 C13 C14 120 . . ? C12 C13 H13 120 . . ? C14 C13 H13 120 . . ? C15 C14 C13 120 . . ? C15 C14 H14 120 . . ? C13 C14 H14 120 . . ? C14 C15 C16 120 . . ? C14 C15 H15 120 . . ? C16 C15 H15 120 . . ? C17 C16 C15 123.2(4) . . ? C17 C16 C11 116.7(4) . . ? C15 C16 C11 120 . . ? C19 C18 C23 120 . . ? C19 C18 C17 121.0(4) . . ? C23 C18 C17 119.0(4) . . ? C20 C19 C18 120 . . ? C20 C19 H19 120 . . ? C18 C19 H19 120 . . ? C19 C20 C21 120 . . ? C19 C20 H20 120 . . ? C21 C20 H20 120 . . ? C22 C21 C20 120 . . ? C22 C21 H21 120 . . ? C20 C21 H21 120 . . ? C23 C22 C21 120 . . ? C23 C22 H22 120 . . ? C21 C22 H22 120 . . ? C22 C23 C18 120 . . ? C22 C23 C10 121.8(3) . . ? C18 C23 C10 118.2(3) . . ? O6 P1 O3 116.74(18) . . ? O6 P1 O5 109.2(2) . . ? O3 P1 O5 107.8(2) . . ? O6 P1 O4 109.9(2) . . ? O3 P1 O4 106.8(2) . . ? O5 P1 O4 106.0(2) . . ? P1 O4 H4 109.5 . . ? P1 O5 H5 109.5 . . ? C3A N2A C5A 122.0(4) . . ? C3A N2A C4A 122.9(5) . . ? C5A N2A C4A 114.5(5) . . ? O1A C3A N2A 125.3(5) . . ? O1A C3A H3A 117.3 . . ? N2A C3A H3A 117.3 . . ? N2A C4A H4A1 109.5 . . ? N2A C4A H4A2 109.5 . . ? H4A1 C4A H4A2 109.5 . . ? N2A C4A H4A3 109.5 . . ? H4A1 C4A H4A3 109.5 . . ? H4A2 C4A H4A3 109.5 . . ? N2A C5A H5A1 109.5 . . ? N2A C5A H5A2 109.5 . . ? H5A1 C5A H5A2 109.5 . . ? N2A C5A H5A3 109.5 . . ? H5A1 C5A H5A3 109.5 . . ? H5A2 C5A H5A3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N8 C2 N3 C6 -1.9(7) . . . . ? I1 C2 N3 C6 -179.2(5) . . . . ? N8 C2 N3 C4 -176.9(5) . . . . ? I1 C2 N3 C4 5.8(8) . . . . ? C2 N3 C4 C5 98.7(6) . . . . ? C6 N3 C4 C5 -75.6(6) . . . . ? C2 N3 C6 C7 0.5(7) . . . . ? C4 N3 C6 C7 175.6(5) . . . . ? N3 C6 C7 N8 1.1(7) . . . . ? N3 C2 N8 C7 2.6(8) . . . . ? I1 C2 N8 C7 179.9(4) . . . . ? N3 C2 N8 C9 -176.7(5) . . . . ? I1 C2 N8 C9 0.6(10) . . . . ? C6 C7 N8 C2 -2.3(8) . . . . ? C6 C7 N8 C9 176.9(5) . . . . ? C2 N8 C9 C10 152.7(6) . . . . ? C7 N8 C9 C10 -26.5(8) . . . . ? N8 C9 C10 C11 -71.7(6) . . . . ? N8 C9 C10 C23 105.5(5) . . . . ? C23 C10 C11 C12 177.9(3) . . . . ? C9 C10 C11 C12 -4.9(5) . . . . ? C23 C10 C11 C16 9.5(5) . . . . ? C9 C10 C11 C16 -173.3(3) . . . . ? C10 C11 C12 C13 -168.8(4) . . . . ? C16 C11 C12 C13 0 . . . . ? C11 C12 C13 C14 0 . . . . ? C12 C13 C14 C15 0 . . . . ? C13 C14 C15 C16 0 . . . . ? C18 C17 C16 C15 -172.7(4) . . . . ? C18 C17 C16 C11 4.9(6) . . . . ? C14 C15 C16 C17 177.5(4) . . . . ? C14 C15 C16 C11 0 . . . . ? C10 C11 C16 C17 -9.7(5) . . . . ? C12 C11 C16 C17 -177.7(4) . . . . ? C10 C11 C16 C15 168.0(4) . . . . ? C12 C11 C16 C15 0 . . . . ? C16 C17 C18 C19 -178.9(4) . . . . ? C16 C17 C18 C23 -0.2(7) . . . . ? C23 C18 C19 C20 0 . . . . ? C17 C18 C19 C20 178.7(4) . . . . ? C18 C19 C20 C21 0 . . . . ? C19 C20 C21 C22 0 . . . . ? C20 C21 C22 C23 0 . . . . ? C21 C22 C23 C18 0 . . . . ? C21 C22 C23 C10 -178.6(4) . . . . ? C19 C18 C23 C22 0 . . . . ? C17 C18 C23 C22 -178.7(4) . . . . ? C19 C18 C23 C10 178.6(4) . . . . ? C17 C18 C23 C10 -0.1(4) . . . . ? C11 C10 C23 C22 174.3(3) . . . . ? C9 C10 C23 C22 -3.1(5) . . . . ? C11 C10 C23 C18 -4.3(5) . . . . ? C9 C10 C23 C18 178.4(3) . . . . ? C5A N2A C3A O1A -0.8(8) . . . . ? C4A N2A C3A O1A -171.9(6) . . . . ?