# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _audit_creation_method 'SHELXL-97 with enCIFer 1.2' _publ_contact_author_name 'Kari Rissanen' _publ_contact_author_email kari.t.rissanen@jyu.fi _publ_contact_author_address ; Prof. Kari Rissanen Nanoscience Center, Department of Chemistry P.O. BOX 35 40014 University of Jyv\"askyl\"a, Finland ; _journal_date_accepted ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _publ_section_title ; Breathing Molecular Crystals: Halogen and Hydrogen Bonded Porous Molecular Crystals with Solvent Induced Adaptation of the Nano-sized Channels ; loop_ _publ_author_name K.Raatikainen K.Rissanen data_CCl4_NIS-HMTA _database_code_depnum_ccdc_archive 'CCDC 855771' _audit_creation_date 2010-10-18T16:05:43-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C Cl4), 4(C4 H4 I N O2), C6 H12 N4' _chemical_formula_sum 'C24 H28 Cl8 I4 N8 O8' _chemical_formula_weight 1347.74 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 42/n m c' _symmetry_space_group_name_Hall '-P 4ac 2a' _symmetry_Int_Tables_number 137 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z' '-x, y+1/2, -z' '-y, -x, -z+1/2' 'y+1/2, x+1/2, -z+1/2' 'y, -x+1/2, z+1/2' '-y+1/2, x, z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z' 'x, -y-1/2, z' 'y, x, z-1/2' '-y-1/2, -x-1/2, z-1/2' '-y, x-1/2, -z-1/2' 'y-1/2, -x, -z-1/2' _cell_length_a 18.1726(3) _cell_length_b 18.1726(3) _cell_length_c 7.0372(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2323.99(9) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 20549 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.7 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.926 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.189 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.6362 _exptl_absorpt_correction_T_max 0.7457 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.47845E-1 _diffrn_orient_matrix_ub_12 0.68719E-2 _diffrn_orient_matrix_ub_13 -0.679169E-1 _diffrn_orient_matrix_ub_21 -0.267305E-1 _diffrn_orient_matrix_ub_22 -0.215701E-1 _diffrn_orient_matrix_ub_23 0.11102 _diffrn_orient_matrix_ub_31 -0.49405E-2 _diffrn_orient_matrix_ub_32 0.501555E-1 _diffrn_orient_matrix_ub_33 0.570512E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_unetI/netI 0.028 _diffrn_reflns_number 10916 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.1 _diffrn_reflns_theta_max 28.52 _diffrn_reflns_theta_full 28.52 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 1568 _reflns_number_gt 1402 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _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^)+(0.0233P)^2^+15.1484P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1568 _refine_ls_number_parameters 115 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0981 _refine_ls_goodness_of_fit_ref 1.23 _refine_ls_restrained_S_all 1.262 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.274 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.133 #----------------------------------------------------------------------------# # 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' 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' Cl Cl 0.1484 0.1585 '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 0.75 0.07180(2) 0.41555(6) 0.02174(15) Uani 1 2 d S . . N2 N 0.75 -0.0204(3) 0.2353(8) 0.0228(12) Uani 1 2 d S . . C3 C 0.75 -0.0924(4) 0.2955(11) 0.0269(15) Uani 1 2 d S . . O4 O 0.75 -0.1107(3) 0.4639(9) 0.059(2) Uani 1 2 d S . . C5 C 0.75 -0.1431(4) 0.1283(11) 0.0317(17) Uani 1 2 d S . . H5A H 0.7128 -0.181 0.1422 0.038 Uiso 0.25 1 d PR . . H5B H 0.7977 -0.1663 0.1126 0.038 Uiso 0.25 1 d PR . . H5C H 0.7023 -0.1666 0.1112 0.038 Uiso 0.25 1 d PR . . H5D H 0.7873 -0.1813 0.1407 0.038 Uiso 0.25 1 d PR . . C6 C 0.7690(7) -0.0914(5) -0.0388(14) 0.037(4) Uani 0.5 1 d P . . H6A H 0.8202 -0.0942 -0.0707 0.044 Uiso 0.5 1 d PR . . H6B H 0.7383 -0.1019 -0.1445 0.044 Uiso 0.5 1 d PR . . C7 C 0.75 -0.0151(5) 0.0417(11) 0.051(3) Uani 1 2 d S . . O8 O 0.7683(5) 0.0426(4) -0.0420(10) 0.040(3) Uani 0.5 1 d PU . . N9 N 0.75 0.1830(3) 0.6296(8) 0.0183(11) Uani 1 2 d S . . C10 C 0.8163(2) 0.1837(2) 0.75 0.0213(12) Uani 1 2 d S . . H10A H 0.8171 0.1392 0.8312 0.026 Uiso 0.5 1 calc PR . . H10B H 0.8608 0.1829 0.6688 0.026 Uiso 0.5 1 calc PR . . C11 C 0.75 0.25 0.5099(13) 0.0203(17) Uani 1 4 d S . . H11A H 0.7941 0.25 0.4272 0.024 Uiso 0.5 2 calc SPR . . H11B H 0.7059 0.25 0.4272 0.024 Uiso 0.5 2 calc SPR . . C12 C 0.9731(8) -0.0252(7) -0.140(2) 0.050(4) Uani 0.25 1 d PDU A -1 Cl13 Cl 1.0568(11) -0.0499(12) -0.244(5) 0.067(3) Uani 0.25 1 d PDU A -1 Cl14 Cl 0.9001(5) -0.0432(5) -0.2951(14) 0.067(2) Uani 0.25 1 d PDU A -1 Cl15 Cl 0.9748(6) 0.0692(4) -0.0896(18) 0.097(3) Uani 0.25 1 d PDU A -1 Cl16 Cl 0.9606(5) -0.0756(5) 0.0702(12) 0.063(2) Uani 0.25 1 d PDU A -1 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 0.0260(2) 0.0169(2) 0.0223(2) -0.00254(17) 0 0 N2 0.035(3) 0.016(2) 0.018(3) -0.001(2) 0 0 C3 0.038(4) 0.016(3) 0.027(4) 0.004(3) 0 0 O4 0.125(7) 0.024(3) 0.028(3) 0.005(3) 0 0 C5 0.040(4) 0.018(3) 0.038(4) -0.007(3) 0 0 C6 0.059(11) 0.026(5) 0.025(5) -0.005(4) -0.005(5) 0.000(5) C7 0.114(9) 0.022(4) 0.018(4) -0.001(3) 0 0 O8 0.067(9) 0.027(3) 0.026(3) 0.008(3) -0.001(4) 0.002(4) N9 0.023(3) 0.013(2) 0.019(3) 0.001(2) 0 0 C10 0.0193(17) 0.0193(17) 0.025(3) 0.000(2) 0.000(2) 0.006(2) C11 0.027(5) 0.018(4) 0.016(4) 0 0 0 C12 0.044(11) 0.029(8) 0.077(13) -0.019(9) -0.015(8) 0.023(9) Cl13 0.030(5) 0.037(7) 0.135(7) 0.033(8) 0.019(6) 0.011(3) Cl14 0.052(4) 0.074(5) 0.076(6) -0.013(5) -0.020(4) 0.004(4) Cl15 0.102(6) 0.036(3) 0.153(8) -0.030(4) -0.052(6) 0.031(4) Cl16 0.072(5) 0.060(4) 0.057(4) -0.022(3) 0.006(4) 0.020(4) #----------------------------------------------------------------------------# # 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 N2 2.101(5) . ? I1 N9 2.520(5) . ? N2 C7 1.366(9) . ? N2 C3 1.375(8) . ? C3 O4 1.231(9) . ? C3 C5 1.495(10) . ? C5 C6 1.544(12) 11_755 ? C5 H5A 0.97 . ? C5 H5B 0.97 . ? C5 H5C 0.973 . ? C5 H5D 0.9732 . ? C6 C7 1.538(13) . ? C6 H6A 0.9592 . ? C6 H6B 0.9485 . ? C7 O8 1.247(10) . ? C7 O8 1.247(10) 11_755 ? C7 C6 1.538(13) 11_755 ? O8 O8 0.664(19) 11_755 ? N9 C10 1.474(5) . ? N9 C10 1.474(5) 11_755 ? N9 C11 1.481(7) . ? C10 N9 1.474(5) 5_666 ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 N9 1.481(7) 2_655 ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 Cl13 1.746(14) . ? C12 Cl14 1.748(13) . ? C12 Cl15 1.752(13) . ? C12 Cl16 1.755(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 I1 N9 179.6(2) . . ? C7 N2 C3 112.0(6) . . ? C7 N2 I1 123.1(5) . . ? C3 N2 I1 124.9(5) . . ? O4 C3 N2 123.6(7) . . ? O4 C3 C5 126.2(7) . . ? N2 C3 C5 110.1(6) . . ? C3 C5 C6 102.9(6) . 11_755 ? C3 C5 H5A 111 . . ? C6 C5 H5A 110.7 11_755 . ? C3 C5 H5B 111 . . ? C6 C5 H5B 112.2 11_755 . ? H5A C5 H5B 109 . . ? C3 C5 H5C 111.6 . . ? C6 C5 H5C 88.5 11_755 . ? H5A C5 H5C 23.2 . . ? H5B C5 H5C 126.2 . . ? C3 C5 H5D 111.6 . . ? C6 C5 H5D 131.1 11_755 . ? H5A C5 H5D 88.3 . . ? H5B C5 H5D 22.9 . . ? H5C C5 H5D 108.6 . . ? C7 C6 H6A 110.5 . . ? C7 C6 H6B 109.8 . . ? H6A C6 H6B 112 . . ? O8 C7 O8 30.9(9) . 11_755 ? O8 C7 N2 122.0(7) . . ? O8 C7 N2 122.0(7) 11_755 . ? O8 C7 C6 130.1(8) . 11_755 ? O8 C7 C6 121.7(7) 11_755 11_755 ? N2 C7 C6 107.7(7) . 11_755 ? O8 C7 C6 121.7(7) . . ? O8 C7 C6 130.1(8) 11_755 . ? N2 C7 C6 107.7(7) . . ? C6 C7 C6 25.9(9) 11_755 . ? O8 O8 C7 74.6(4) 11_755 . ? C10 N9 C10 109.8(4) . 11_755 ? C10 N9 C11 108.7(3) . . ? C10 N9 C11 108.7(3) 11_755 . ? C10 N9 I1 110.5(3) . . ? C10 N9 I1 110.5(3) 11_755 . ? C11 N9 I1 108.6(4) . . ? N9 C10 N9 110.1(6) 5_666 . ? N9 C10 H10A 109.6 5_666 . ? N9 C10 H10A 109.6 . . ? N9 C10 H10B 109.6 5_666 . ? N9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? N9 C11 N9 110.6(7) 2_655 . ? N9 C11 H11A 109.5 2_655 . ? N9 C11 H11A 109.5 . . ? N9 C11 H11B 109.5 2_655 . ? N9 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? Cl13 C12 Cl14 110.7(12) . . ? Cl13 C12 Cl15 108.7(11) . . ? Cl14 C12 Cl15 108.9(8) . . ? Cl13 C12 Cl16 109.3(13) . . ? Cl14 C12 Cl16 109.3(9) . . ? Cl15 C12 Cl16 109.9(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 N9 I1 N2 C7 0.00(2) . . . . ? N9 I1 N2 C3 180.00(2) . . . . ? C7 N2 C3 O4 180 . . . . ? I1 N2 C3 O4 0 . . . . ? C7 N2 C3 C5 0 . . . . ? I1 N2 C3 C5 180 . . . . ? O4 C3 C5 C6 166.8(5) . . . 11_755 ? N2 C3 C5 C6 -13.2(5) . . . 11_755 ? C3 N2 C7 O8 -161.7(5) . . . . ? I1 N2 C7 O8 18.3(5) . . . . ? C3 N2 C7 O8 161.7(5) . . . 11_755 ? I1 N2 C7 O8 -18.3(5) . . . 11_755 ? C3 N2 C7 C6 13.6(5) . . . 11_755 ? I1 N2 C7 C6 -166.4(5) . . . 11_755 ? C3 N2 C7 C6 -13.6(5) . . . . ? I1 N2 C7 C6 166.4(5) . . . . ? N2 C7 O8 O8 -100.0(4) . . . 11_755 ? C6 C7 O8 O8 85.9(7) 11_755 . . 11_755 ? C6 C7 O8 O8 116.3(7) . . . 11_755 ? N2 I1 N9 C10 -119.1(3) . . . . ? N2 I1 N9 C10 119.1(3) . . . 11_755 ? N2 I1 N9 C11 0.00(6) . . . . ? C10 N9 C10 N9 -59.6(3) 11_755 . . 5_666 ? C11 N9 C10 N9 59.2(4) . . . 5_666 ? I1 N9 C10 N9 178.3(3) . . . 5_666 ? C10 N9 C11 N9 -59.7(3) . . . 2_655 ? C10 N9 C11 N9 59.7(3) 11_755 . . 2_655 ? I1 N9 C11 N9 180.0000(10) . . . 2_655 ? data_CHCl3_NIS-HMTA _database_code_depnum_ccdc_archive 'CCDC 855772' _audit_creation_date 2010-11-01T12:46:25-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H12 N4, 4(C4 H4 I N O2), C H Cl3' _chemical_formula_sum 'C23 H29 Cl3 I4 N8 O8' _chemical_formula_weight 1159.49 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.3584(7) _cell_length_b 7.0340(2) _cell_length_c 21.0654(4) _cell_angle_alpha 90 _cell_angle_beta 109.2160(10) _cell_angle_gamma 90 _cell_volume 3688.03(16) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3158 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 26.733 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 2.088 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2200 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.65 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.6726 _exptl_absorpt_correction_T_max 0.7457 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.272426E-1 _diffrn_orient_matrix_ub_12 0.282175E-1 _diffrn_orient_matrix_ub_13 0.223759E-1 _diffrn_orient_matrix_ub_21 -0.287171E-1 _diffrn_orient_matrix_ub_22 -0.572145E-1 _diffrn_orient_matrix_ub_23 -0.389785E-1 _diffrn_orient_matrix_ub_31 0.68817E-2 _diffrn_orient_matrix_ub_32 -0.12705 _diffrn_orient_matrix_ub_33 0.225229E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_unetI/netI 0.0333 _diffrn_reflns_number 27051 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 28.33 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 4579 _reflns_number_gt 4000 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _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^)+(0.0172P)^2^+29.5200P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4579 _refine_ls_number_parameters 218 _refine_ls_number_restraints 37 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.032 _refine_ls_wR_factor_ref 0.0705 _refine_ls_wR_factor_gt 0.068 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.236 _refine_diff_density_min -1.455 _refine_diff_density_rms 0.131 #----------------------------------------------------------------------------# # 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' 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' Cl Cl 0.1484 0.1585 '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 0.871762(9) 0.83080(3) 0.221822(11) 0.02059(7) Uani 1 1 d . . . N2 N 0.80395(12) 1.0076(4) 0.19850(17) 0.0253(7) Uani 1 1 d . . . C3 C 0.75224(16) 0.9362(6) 0.1745(3) 0.0405(11) Uani 1 1 d U . . O4 O 0.74189(13) 0.7683(5) 0.1679(3) 0.0748(15) Uani 1 1 d U . . C5 C 0.71365(17) 1.1001(7) 0.1602(3) 0.0464(13) Uani 1 1 d U . . H5A H 0.6934 1.1021 0.1924 0.056 Uiso 1 1 calc R . . H5B H 0.6878 1.0923 0.114 0.056 Uiso 1 1 calc R . . C6 C 0.74878(18) 1.2747(7) 0.1686(3) 0.0433(11) Uani 1 1 d U . . H6A H 0.744 1.335 0.1245 0.052 Uiso 1 1 calc R . . H6B H 0.74 1.3688 0.1983 0.052 Uiso 1 1 calc R . . C7 C 0.80555(16) 1.2026(6) 0.1997(2) 0.0279(8) Uani 1 1 d U . . O8 O 0.84640(12) 1.2958(4) 0.22123(19) 0.0433(8) Uani 1 1 d . . . I9 I 0.959629(9) 0.14981(3) 0.085744(11) 0.02238(7) Uani 1 1 d . . . N10 N 0.93274(12) -0.0383(5) 0.00503(15) 0.0241(7) Uani 1 1 d . . . C11 C 0.90072(16) 0.0150(6) -0.0589(2) 0.0317(9) Uani 1 1 d . . . O12 O 0.88606(16) 0.1743(5) -0.07513(18) 0.0603(12) Uani 1 1 d . . . C13 C 0.88772(16) -0.1608(6) -0.1023(2) 0.0317(9) Uani 1 1 d . . . H13A H 0.9027 -0.1511 -0.1396 0.038 Uiso 1 1 calc R . . H13B H 0.8484 -0.1793 -0.1215 0.038 Uiso 1 1 calc R . . C14 C 0.91390(18) -0.3246(6) -0.0552(2) 0.0326(9) Uani 1 1 d . . . H14A H 0.8864 -0.4146 -0.0508 0.039 Uiso 1 1 calc R . . H14B H 0.9394 -0.3944 -0.0722 0.039 Uiso 1 1 calc R . . C15 C 0.94295(16) -0.2312(6) 0.01135(19) 0.0258(8) Uani 1 1 d . . . O16 O 0.97076(15) -0.3071(4) 0.06239(14) 0.0408(8) Uani 1 1 d . . . N17 N 0.95232(11) 0.6162(4) 0.24274(14) 0.0175(6) Uani 1 1 d . . . C18 C 0.96271(13) 0.4940(5) 0.30269(17) 0.0190(7) Uani 1 1 d . . . H18A H 0.931 0.4128 0.2979 0.023 Uiso 1 1 calc R . . H18B H 0.9689 0.5743 0.3431 0.023 Uiso 1 1 calc R . . N19 N 1.01047(12) 0.3725(4) 0.31087(14) 0.0191(6) Uani 1 1 d . . . C20 C 1 0.2531(7) 0.25 0.0225(10) Uani 1 2 d S . . H20A H 0.9686 0.1704 0.2452 0.027 Uiso 0.5 1 calc PR . . H20B H 1.0314 0.1704 0.2548 0.027 Uiso 0.5 1 calc PR . . C21 C 0.94243(13) 0.4938(5) 0.18231(17) 0.0195(7) Uani 1 1 d . . . H21A H 0.9105 0.413 0.1768 0.023 Uiso 1 1 calc R . . H21B H 0.9351 0.5746 0.1418 0.023 Uiso 1 1 calc R . . C22 C 1 0.7371(7) 0.25 0.0181(9) Uani 1 2 d S . . H22A H 1.0069 0.8196 0.29 0.022 Uiso 0.5 1 calc PR . . H22B H 0.9931 0.8196 0.21 0.022 Uiso 0.5 1 calc PR . . Cl23 Cl 0.68474(13) 1.0664(7) -0.02937(17) 0.0821(11) Uani 0.5 1 d P . . C24 C 0.7263(5) 0.877(2) -0.0338(6) 0.072(4) Uani 0.5 1 d P . . H24 H 0.7264 0.8761 -0.0812 0.086 Uiso 0.5 1 calc PR . . Cl25 Cl 0.79519(10) 0.8810(6) 0.01738(13) 0.1448(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 0.01423(11) 0.02008(12) 0.02701(13) -0.00137(9) 0.00617(9) 0.00076(8) N2 0.0134(14) 0.0201(15) 0.0409(19) -0.0051(13) 0.0068(13) -0.0002(12) C3 0.0153(18) 0.030(2) 0.071(3) -0.018(2) 0.0068(19) 0.0006(16) O4 0.0183(16) 0.0300(18) 0.162(5) -0.031(2) 0.010(2) -0.0046(14) C5 0.0180(19) 0.032(2) 0.079(4) -0.012(2) 0.002(2) 0.0073(17) C6 0.031(2) 0.029(2) 0.063(3) -0.001(2) 0.004(2) 0.0104(18) C7 0.0253(19) 0.0229(19) 0.036(2) -0.0008(16) 0.0114(16) 0.0014(15) O8 0.0276(16) 0.0266(16) 0.072(2) -0.0018(15) 0.0116(15) -0.0065(13) I9 0.01886(12) 0.02523(13) 0.02130(12) -0.00558(9) 0.00424(9) -0.00174(9) N10 0.0225(15) 0.0291(17) 0.0187(14) -0.0067(12) 0.0042(12) -0.0036(13) C11 0.0219(19) 0.036(2) 0.030(2) -0.0055(17) -0.0016(16) 0.0045(17) O12 0.069(3) 0.043(2) 0.042(2) -0.0072(16) -0.0181(18) 0.0262(18) C13 0.0230(19) 0.042(2) 0.0248(19) -0.0113(17) 0.0013(15) -0.0051(17) C14 0.041(2) 0.031(2) 0.027(2) -0.0103(16) 0.0129(18) -0.0167(18) C15 0.030(2) 0.0264(19) 0.0229(19) -0.0041(15) 0.0117(16) -0.0095(16) O16 0.068(2) 0.0297(16) 0.0196(14) 0.0043(12) 0.0081(14) -0.0032(15) N17 0.0149(13) 0.0180(14) 0.0197(14) -0.0003(11) 0.0056(11) -0.0001(11) C18 0.0167(16) 0.0232(17) 0.0168(15) 0.0016(13) 0.0050(13) 0.0001(14) N19 0.0187(14) 0.0179(14) 0.0195(14) 0.0026(11) 0.0047(11) 0.0001(11) C20 0.029(3) 0.015(2) 0.022(2) 0 0.006(2) 0 C21 0.0158(16) 0.0228(17) 0.0175(16) -0.0004(13) 0.0019(13) -0.0005(13) C22 0.015(2) 0.015(2) 0.024(2) 0 0.0057(19) 0 Cl23 0.0525(17) 0.132(3) 0.0658(19) -0.031(2) 0.0249(15) 0.001(2) C24 0.062(8) 0.111(11) 0.043(6) -0.003(7) 0.019(6) -0.022(8) Cl25 0.0777(14) 0.258(4) 0.0903(16) 0.023(2) 0.0160(12) -0.0447(19) #----------------------------------------------------------------------------# # 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 N2 2.099(3) . ? I1 N17 2.523(3) . ? N2 C7 1.372(5) . ? N2 C3 1.383(5) . ? C3 O4 1.210(6) . ? C3 C5 1.501(6) . ? C5 C6 1.513(7) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.510(6) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 O8 1.214(5) . ? I9 N10 2.086(3) . ? N10 C15 1.381(5) . ? N10 C11 1.386(5) . ? C11 O12 1.198(5) . ? C11 C13 1.508(6) . ? C13 C14 1.529(6) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.509(5) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 O16 1.208(5) . ? N17 C18 1.477(4) . ? N17 C22 1.483(4) . ? N17 C21 1.487(4) . ? C18 N19 1.484(4) . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? N19 C21 1.474(4) 2_755 ? N19 C20 1.481(4) . ? C20 N19 1.481(4) 2_755 ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? C21 N19 1.474(4) 2_755 ? C21 H21A 0.99 . ? C21 H21B 0.99 . ? C22 N17 1.483(4) 2_755 ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? Cl23 C24 1.746(16) . ? C24 Cl25 1.782(13) . ? C24 Cl25 1.964(15) 7_665 ? C24 H24 1 . ? Cl25 C24 1.964(15) 7_665 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 I1 N17 176.72(11) . . ? C7 N2 C3 113.0(3) . . ? C7 N2 I1 124.7(2) . . ? C3 N2 I1 122.1(3) . . ? O4 C3 N2 123.7(4) . . ? O4 C3 C5 127.9(4) . . ? N2 C3 C5 108.4(4) . . ? C3 C5 C6 104.6(3) . . ? C3 C5 H5A 110.8 . . ? C6 C5 H5A 110.8 . . ? C3 C5 H5B 110.8 . . ? C6 C5 H5B 110.8 . . ? H5A C5 H5B 108.9 . . ? C7 C6 C5 105.0(4) . . ? C7 C6 H6A 110.7 . . ? C5 C6 H6A 110.7 . . ? C7 C6 H6B 110.7 . . ? C5 C6 H6B 110.7 . . ? H6A C6 H6B 108.8 . . ? O8 C7 N2 124.4(4) . . ? O8 C7 C6 127.7(4) . . ? N2 C7 C6 107.9(3) . . ? C15 N10 C11 113.4(3) . . ? C15 N10 I9 122.8(2) . . ? C11 N10 I9 123.8(3) . . ? O12 C11 N10 124.5(4) . . ? O12 C11 C13 127.4(4) . . ? N10 C11 C13 108.2(3) . . ? C11 C13 C14 105.1(3) . . ? C11 C13 H13A 110.7 . . ? C14 C13 H13A 110.7 . . ? C11 C13 H13B 110.7 . . ? C14 C13 H13B 110.7 . . ? H13A C13 H13B 108.8 . . ? C15 C14 C13 104.9(3) . . ? C15 C14 H14A 110.8 . . ? C13 C14 H14A 110.8 . . ? C15 C14 H14B 110.8 . . ? C13 C14 H14B 110.8 . . ? H14A C14 H14B 108.8 . . ? O16 C15 N10 124.2(4) . . ? O16 C15 C14 127.4(4) . . ? N10 C15 C14 108.4(3) . . ? C18 N17 C22 109.5(2) . . ? C18 N17 C21 109.0(3) . . ? C22 N17 C21 108.9(2) . . ? C18 N17 I1 114.0(2) . . ? C22 N17 I1 108.1(2) . . ? C21 N17 I1 107.25(19) . . ? N17 C18 N19 110.2(3) . . ? N17 C18 H18A 109.6 . . ? N19 C18 H18A 109.6 . . ? N17 C18 H18B 109.6 . . ? N19 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? C21 N19 C20 108.9(2) 2_755 . ? C21 N19 C18 109.5(3) 2_755 . ? C20 N19 C18 108.5(2) . . ? N19 C20 N19 110.9(4) . 2_755 ? N19 C20 H20A 109.5 . . ? N19 C20 H20A 109.5 2_755 . ? N19 C20 H20B 109.5 . . ? N19 C20 H20B 109.5 2_755 . ? H20A C20 H20B 108.1 . . ? N19 C21 N17 110.3(3) 2_755 . ? N19 C21 H21A 109.6 2_755 . ? N17 C21 H21A 109.6 . . ? N19 C21 H21B 109.6 2_755 . ? N17 C21 H21B 109.6 . . ? H21A C21 H21B 108.1 . . ? N17 C22 N17 110.0(4) . 2_755 ? N17 C22 H22A 109.7 . . ? N17 C22 H22A 109.7 2_755 . ? N17 C22 H22B 109.7 . . ? N17 C22 H22B 109.7 2_755 . ? H22A C22 H22B 108.2 . . ? Cl23 C24 Cl25 119.2(8) . . ? Cl23 C24 Cl25 118.3(7) . 7_665 ? Cl25 C24 Cl25 101.7(7) . 7_665 ? Cl23 C24 H24 105.4 . . ? Cl25 C24 H24 105.4 . . ? Cl25 C24 H24 105.4 7_665 . ? C24 Cl25 C24 78.3(7) . 7_665 ? 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 N17 I1 N2 C7 -99.1(19) . . . . ? N17 I1 N2 C3 75(2) . . . . ? C7 N2 C3 O4 178.4(5) . . . . ? I1 N2 C3 O4 3.4(8) . . . . ? C7 N2 C3 C5 -2.7(6) . . . . ? I1 N2 C3 C5 -177.6(3) . . . . ? O4 C3 C5 C6 -172.7(6) . . . . ? N2 C3 C5 C6 8.4(6) . . . . ? C3 C5 C6 C7 -10.5(6) . . . . ? C3 N2 C7 O8 177.1(4) . . . . ? I1 N2 C7 O8 -8.2(6) . . . . ? C3 N2 C7 C6 -4.3(5) . . . . ? I1 N2 C7 C6 170.4(3) . . . . ? C5 C6 C7 O8 -172.1(5) . . . . ? C5 C6 C7 N2 9.3(5) . . . . ? C15 N10 C11 O12 178.4(5) . . . . ? I9 N10 C11 O12 1.7(6) . . . . ? C15 N10 C11 C13 -0.8(5) . . . . ? I9 N10 C11 C13 -177.5(3) . . . . ? O12 C11 C13 C14 -176.7(5) . . . . ? N10 C11 C13 C14 2.5(5) . . . . ? C11 C13 C14 C15 -3.1(4) . . . . ? C11 N10 C15 O16 178.6(4) . . . . ? I9 N10 C15 O16 -4.7(6) . . . . ? C11 N10 C15 C14 -1.3(5) . . . . ? I9 N10 C15 C14 175.4(2) . . . . ? C13 C14 C15 O16 -177.1(4) . . . . ? C13 C14 C15 N10 2.8(4) . . . . ? N2 I1 N17 C18 -146.4(18) . . . . ? N2 I1 N17 C22 91.6(19) . . . . ? N2 I1 N17 C21 -26(2) . . . . ? C22 N17 C18 N19 -59.0(3) . . . . ? C21 N17 C18 N19 60.0(3) . . . . ? I1 N17 C18 N19 179.8(2) . . . . ? N17 C18 N19 C21 59.0(3) . . . 2_755 ? N17 C18 N19 C20 -59.7(3) . . . . ? C21 N19 C20 N19 -59.5(2) 2_755 . . 2_755 ? C18 N19 C20 N19 59.5(2) . . . 2_755 ? C18 N17 C21 N19 -59.8(3) . . . 2_755 ? C22 N17 C21 N19 59.6(3) . . . 2_755 ? I1 N17 C21 N19 176.4(2) . . . 2_755 ? C18 N17 C22 N17 59.6(2) . . . 2_755 ? C21 N17 C22 N17 -59.5(2) . . . 2_755 ? I1 N17 C22 N17 -175.74(18) . . . 2_755 ? Cl23 C24 Cl25 C24 132.1(11) . . . 7_665 ? Cl25 C24 Cl25 C24 0 7_665 . . 7_665 ? data_DCM_NIS-HMTA _database_code_depnum_ccdc_archive 'CCDC 855773' _audit_creation_date 2009-11-20T16:51:45-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H12 N4, 4(C4 H4 I N O2), 4(C H2 Cl2)' _chemical_formula_sum 'C26 H36 Cl8 I4 N8 O8' _chemical_formula_weight 1379.83 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 43 21 2' _symmetry_space_group_name_Hall '-P 4nw 2abw' _symmetry_Int_Tables_number 96 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/4' '-x+1/2, y+1/2, -z+3/4' '-y, -x, -z+1/2' 'y, x, -z' 'y+1/2, -x+1/2, z+1/4' '-y+1/2, x+1/2, z+3/4' _cell_length_a 17.2587(3) _cell_length_b 17.2587(3) _cell_length_c 15.5855(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4642.34(16) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4504 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.283 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.974 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2640 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.195 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.6279 _exptl_absorpt_correction_T_max 0.7456 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.35808E-1 _diffrn_orient_matrix_ub_12 -0.155643E-1 _diffrn_orient_matrix_ub_13 -0.474071E-1 _diffrn_orient_matrix_ub_21 0.388713E-1 _diffrn_orient_matrix_ub_22 -0.388315E-1 _diffrn_orient_matrix_ub_23 -0.203701E-1 _diffrn_orient_matrix_ub_31 -0.237499E-1 _diffrn_orient_matrix_ub_32 -0.400889E-1 _diffrn_orient_matrix_ub_33 0.381367E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_unetI/netI 0.0406 _diffrn_reflns_number 24097 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 27.84 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.95 _reflns_number_total 5080 _reflns_number_gt 4436 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _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^)+(0.0103P)^2^+8.5870P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5080 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0641 _refine_ls_wR_factor_gt 0.0612 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.46(3) _refine_diff_density_max 0.48 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.099 #----------------------------------------------------------------------------# # 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' 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' Cl Cl 0.1484 0.1585 '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 0.189238(14) 0.00640(2) 0.161572(16) 0.02394(8) Uani 1 1 d . . . N2 N 0.27294(18) 0.0055(3) 0.2591(2) 0.0249(9) Uani 1 1 d . . . C3 C 0.2547(2) -0.0039(4) 0.3444(3) 0.0308(11) Uani 1 1 d . . . O4 O 0.18856(17) -0.0116(3) 0.3708(2) 0.0468(11) Uani 1 1 d . . . C5 C 0.3278(2) -0.0016(4) 0.3958(3) 0.0395(13) Uani 1 1 d . . . H5A H 0.3348 -0.0504 0.4283 0.047 Uiso 1 1 calc R . . H5B H 0.3271 0.0423 0.4367 0.047 Uiso 1 1 calc R . . C6 C 0.3922(3) 0.0086(4) 0.3302(3) 0.0429(14) Uani 1 1 d . . . H6A H 0.4214 0.057 0.3413 0.051 Uiso 1 1 calc R . . H6B H 0.4286 -0.0357 0.3322 0.051 Uiso 1 1 calc R . . C7 C 0.3521(3) 0.0124(3) 0.2446(3) 0.0321(12) Uani 1 1 d . . . O8 O 0.3805(2) 0.0204(3) 0.1746(2) 0.0481(11) Uani 1 1 d . . . I9 I 0.00517(2) -0.174117(13) -0.153184(15) 0.02224(8) Uani 1 1 d . . . N10 N 0.0017(3) -0.26982(18) -0.2366(2) 0.0253(9) Uani 1 1 d . . . C11 C 0.0068(4) -0.3453(2) -0.2072(3) 0.0302(11) Uani 1 1 d . . . O12 O 0.0124(3) -0.36258(18) -0.1324(2) 0.0441(10) Uani 1 1 d . . . C13 C 0.0045(4) -0.3986(2) -0.2840(3) 0.0317(11) Uani 1 1 d . . . H13A H -0.0413 -0.4332 -0.2813 0.038 Uiso 1 1 calc R . . H13B H 0.0519 -0.4309 -0.2867 0.038 Uiso 1 1 calc R . . C14 C -0.0005(4) -0.3452(2) -0.3616(3) 0.0332(12) Uani 1 1 d . . . H14A H 0.0451 -0.352 -0.3993 0.04 Uiso 1 1 calc R . . H14B H -0.048 -0.3558 -0.3952 0.04 Uiso 1 1 calc R . . C15 C -0.0025(4) -0.2645(2) -0.3246(3) 0.0306(11) Uani 1 1 d . . . O16 O -0.0076(3) -0.20368(18) -0.36360(19) 0.0458(10) Uani 1 1 d . . . N17 N 0.0092(3) -0.06018(18) -0.0557(2) 0.0190(8) Uani 1 1 d . . . C18 C 0.0797(3) -0.0610(3) -0.0017(3) 0.0199(13) Uani 1 1 d . . . H18A H 0.1263 -0.0615 -0.0386 0.024 Uiso 1 1 calc R . . H18B H 0.0803 -0.1082 0.0343 0.024 Uiso 1 1 calc R . . N19 N 0.08041(18) 0.0094(3) 0.0542(2) 0.0212(8) Uani 1 1 d . . . C20 C 0.0789(3) 0.0789(3) 0 0.0241(18) Uani 1 2 d S . . H20A H 0.0798 0.1257 0.0368 0.029 Uiso 0.5 1 calc PR . . H20B H 0.1257 0.0798 -0.0368 0.029 Uiso 0.5 1 calc PR . . C21 C 0.0101(2) 0.0092(2) 0.1096(2) 0.0203(8) Uani 1 1 d . . . H21A H 0.0104 -0.0373 0.1468 0.024 Uiso 1 1 calc R . . H21B H 0.0102 0.0556 0.1469 0.024 Uiso 1 1 calc R . . C22 C -0.0603(3) -0.0603(3) 0 0.0199(17) Uani 1 2 d S . . H22A H -0.0605 -0.1076 0.0359 0.024 Uiso 0.5 1 calc PR . . H22B H -0.1076 -0.0605 -0.0359 0.024 Uiso 0.5 1 calc PR . . C1A C 0.2229(5) 0.2233(4) 0.2501(4) 0.058(3) Uani 1 1 d . . . H1A1 H 0.2122 0.1858 0.2035 0.07 Uiso 1 1 calc R . . H1A2 H 0.1883 0.211 0.2988 0.07 Uiso 1 1 calc R . . Cl1A Cl 0.20366(13) 0.31768(12) 0.21357(13) 0.0582(6) Uani 1 1 d . . . Cl2A Cl 0.32056(14) 0.21391(14) 0.28317(15) 0.0691(7) Uani 1 1 d . . . C1B C 0.2790(4) 0.2790(4) 0 0.048(3) Uani 1 2 d S . . H1B1 H 0.2912 0.3144 0.0481 0.058 Uiso 0.5 1 calc PR . . H1B2 H 0.3144 0.2912 -0.0481 0.058 Uiso 0.5 1 calc PR . . Cl1B Cl 0.29393(13) 0.18219(12) 0.03310(14) 0.0571(6) Uani 1 1 d . . . C1C C 0.2822(5) 0.2822(5) 0.5 0.062(3) Uani 1 2 d S . . H1C1 H 0.2941 0.3182 0.5477 0.075 Uiso 0.5 1 calc PR . . H1C2 H 0.3182 0.2941 0.4523 0.075 Uiso 0.5 1 calc PR . . Cl1C Cl 0.18705(14) 0.29849(15) 0.46554(16) 0.0740(7) 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 0.02625(14) 0.0264(2) 0.01916(14) 0.00075(16) -0.00075(10) -0.00168(13) N2 0.0207(16) 0.036(3) 0.0176(18) -0.006(2) -0.0002(13) 0.000(2) C3 0.026(2) 0.045(3) 0.021(2) -0.002(3) -0.0018(18) -0.001(3) O4 0.0285(17) 0.086(3) 0.0260(17) 0.010(2) 0.0040(14) -0.003(2) C5 0.032(2) 0.059(4) 0.028(3) -0.006(3) -0.007(2) 0.001(3) C6 0.021(2) 0.053(4) 0.054(3) -0.002(4) -0.003(2) -0.003(3) C7 0.028(2) 0.033(3) 0.036(3) -0.002(3) 0.005(2) 0.000(3) O8 0.0372(19) 0.066(3) 0.041(2) 0.000(2) 0.0177(17) -0.005(2) I9 0.0282(2) 0.02006(13) 0.01850(14) -0.00213(10) 0.00052(16) 0.00032(12) N10 0.037(3) 0.0203(16) 0.0186(18) -0.0037(13) -0.001(2) 0.000(2) C11 0.040(3) 0.021(2) 0.030(3) -0.0006(18) 0.000(3) 0.005(3) O12 0.081(3) 0.0253(16) 0.0263(18) 0.0054(14) -0.002(2) 0.003(2) C13 0.041(3) 0.0189(19) 0.035(3) -0.0094(18) -0.003(3) -0.002(3) C14 0.048(4) 0.028(2) 0.023(2) -0.0074(18) -0.002(3) 0.000(3) C15 0.042(3) 0.028(2) 0.021(2) -0.0002(18) 0.002(3) -0.005(3) O16 0.083(3) 0.0316(17) 0.0225(16) 0.0034(14) 0.001(2) -0.002(2) N17 0.020(2) 0.0215(16) 0.0152(18) 0.0006(13) -0.002(2) -0.0025(18) C18 0.020(3) 0.023(3) 0.016(3) -0.001(2) -0.001(2) 0.0019(19) N19 0.0227(17) 0.026(2) 0.0152(18) -0.005(2) 0.0004(13) -0.0003(19) C20 0.024(2) 0.024(2) 0.024(5) 0.000(2) 0.000(2) -0.002(3) C21 0.0212(18) 0.0253(19) 0.0143(19) -0.0010(17) -0.0005(16) -0.003(2) C22 0.022(2) 0.022(2) 0.015(4) -0.004(2) 0.004(2) -0.005(3) C1A 0.075(6) 0.054(5) 0.046(6) -0.011(4) 0.012(5) -0.026(4) Cl1A 0.0652(13) 0.0599(14) 0.0496(14) -0.0026(9) 0.0049(10) 0.0100(9) Cl2A 0.0734(16) 0.0699(15) 0.0639(16) -0.0096(11) -0.0038(11) 0.0189(10) C1B 0.036(3) 0.036(3) 0.073(9) -0.001(4) 0.001(4) 0.004(4) Cl1B 0.0609(12) 0.0489(12) 0.0615(15) 0.0004(9) 0.0047(10) 0.0079(9) C1C 0.053(4) 0.053(4) 0.080(10) -0.006(5) 0.006(5) 0.003(5) Cl1C 0.0652(14) 0.0854(17) 0.0714(18) 0.0006(13) 0.0130(12) 0.0084(12) #----------------------------------------------------------------------------# # 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 N2 2.096(3) . ? I1 N19 2.516(3) . ? N2 C3 1.376(5) . ? N2 C7 1.390(5) . ? C3 O4 1.221(5) . ? C3 C5 1.496(6) . ? C5 C6 1.520(7) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.503(7) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 O8 1.204(5) . ? I9 N10 2.103(3) . ? I9 N17 2.486(3) . ? N10 C15 1.376(5) . ? N10 C11 1.384(5) . ? C11 O12 1.206(5) . ? C11 C13 1.511(6) . ? C13 C14 1.524(6) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.509(6) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 O16 1.216(5) . ? N17 C21 1.476(5) 6 ? N17 C18 1.479(6) . ? N17 C22 1.479(5) . ? C18 N19 1.495(6) . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? N19 C20 1.467(6) . ? N19 C21 1.490(5) . ? C20 N19 1.467(6) 6 ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? C21 N17 1.476(5) 6 ? C21 H21A 0.99 . ? C21 H21B 0.99 . ? C22 N17 1.479(5) 6 ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? C1A Cl1A 1.757(7) . ? C1A Cl2A 1.769(8) . ? C1A H1A1 0.99 . ? C1A H1A2 0.99 . ? C1B Cl1B 1.767(6) 6 ? C1B Cl1B 1.767(6) . ? C1B H1B1 0.99 . ? C1B H1B2 0.99 . ? C1C Cl1C 1.751(7) . ? C1C Cl1C 1.751(7) 6_556 ? C1C H1C1 0.99 . ? C1C H1C2 0.99 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 I1 N19 175.20(11) . . ? C3 N2 C7 113.0(3) . . ? C3 N2 I1 122.9(3) . . ? C7 N2 I1 124.0(3) . . ? O4 C3 N2 123.6(4) . . ? O4 C3 C5 127.6(4) . . ? N2 C3 C5 108.8(4) . . ? C3 C5 C6 105.0(4) . . ? C3 C5 H5A 110.7 . . ? C6 C5 H5A 110.7 . . ? C3 C5 H5B 110.7 . . ? C6 C5 H5B 110.7 . . ? H5A C5 H5B 108.8 . . ? C7 C6 C5 105.4(4) . . ? C7 C6 H6A 110.7 . . ? C5 C6 H6A 110.7 . . ? C7 C6 H6B 110.7 . . ? C5 C6 H6B 110.7 . . ? H6A C6 H6B 108.8 . . ? O8 C7 N2 123.8(4) . . ? O8 C7 C6 128.4(4) . . ? N2 C7 C6 107.8(4) . . ? N10 I9 N17 179.48(12) . . ? C15 N10 C11 113.4(3) . . ? C15 N10 I9 124.4(3) . . ? C11 N10 I9 122.1(3) . . ? O12 C11 N10 124.0(4) . . ? O12 C11 C13 128.0(4) . . ? N10 C11 C13 108.0(4) . . ? C11 C13 C14 105.2(3) . . ? C11 C13 H13A 110.7 . . ? C14 C13 H13A 110.7 . . ? C11 C13 H13B 110.7 . . ? C14 C13 H13B 110.7 . . ? H13A C13 H13B 108.8 . . ? C15 C14 C13 104.9(3) . . ? C15 C14 H14A 110.8 . . ? C13 C14 H14A 110.8 . . ? C15 C14 H14B 110.8 . . ? C13 C14 H14B 110.8 . . ? H14A C14 H14B 108.8 . . ? O16 C15 N10 124.1(4) . . ? O16 C15 C14 127.4(4) . . ? N10 C15 C14 108.6(3) . . ? C21 N17 C18 109.3(4) 6 . ? C21 N17 C22 109.6(3) 6 . ? C18 N17 C22 109.4(3) . . ? C21 N17 I9 107.6(2) 6 . ? C18 N17 I9 111.3(3) . . ? C22 N17 I9 109.6(3) . . ? N17 C18 N19 109.3(4) . . ? N17 C18 H18A 109.8 . . ? N19 C18 H18A 109.8 . . ? N17 C18 H18B 109.8 . . ? N19 C18 H18B 109.8 . . ? H18A C18 H18B 108.3 . . ? C20 N19 C21 108.7(3) . . ? C20 N19 C18 109.2(3) . . ? C21 N19 C18 109.2(4) . . ? C20 N19 I1 114.4(3) . . ? C21 N19 I1 102.9(2) . . ? C18 N19 I1 112.2(3) . . ? N19 C20 N19 111.1(5) 6 . ? N19 C20 H20A 109.4 6 . ? N19 C20 H20A 109.4 . . ? N19 C20 H20B 109.4 6 . ? N19 C20 H20B 109.4 . . ? H20A C20 H20B 108 . . ? N17 C21 N19 109.8(3) 6 . ? N17 C21 H21A 109.7 6 . ? N19 C21 H21A 109.7 . . ? N17 C21 H21B 109.7 6 . ? N19 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? N17 C22 N17 110.0(5) . 6 ? N17 C22 H22A 109.7 . . ? N17 C22 H22A 109.7 6 . ? N17 C22 H22B 109.7 . . ? N17 C22 H22B 109.7 6 . ? H22A C22 H22B 108.2 . . ? Cl1A C1A Cl2A 111.1(4) . . ? Cl1A C1A H1A1 109.4 . . ? Cl2A C1A H1A1 109.4 . . ? Cl1A C1A H1A2 109.4 . . ? Cl2A C1A H1A2 109.4 . . ? H1A1 C1A H1A2 108 . . ? Cl1B C1B Cl1B 111.2(5) 6 . ? Cl1B C1B H1B1 109.4 6 . ? Cl1B C1B H1B1 109.4 . . ? Cl1B C1B H1B2 109.4 6 . ? Cl1B C1B H1B2 109.4 . . ? H1B1 C1B H1B2 108 . . ? Cl1C C1C Cl1C 113.2(6) . 6_556 ? Cl1C C1C H1C1 108.9 . . ? Cl1C C1C H1C1 108.9 6_556 . ? Cl1C C1C H1C2 108.9 . . ? Cl1C C1C H1C2 108.9 6_556 . ? H1C1 C1C H1C2 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N19 I1 N2 C3 17(2) . . . . ? N19 I1 N2 C7 -164.5(19) . . . . ? C7 N2 C3 O4 -179.4(6) . . . . ? I1 N2 C3 O4 -0.8(10) . . . . ? C7 N2 C3 C5 1.4(8) . . . . ? I1 N2 C3 C5 -180.0(4) . . . . ? O4 C3 C5 C6 179.7(7) . . . . ? N2 C3 C5 C6 -1.2(7) . . . . ? C3 C5 C6 C7 0.6(7) . . . . ? C3 N2 C7 O8 179.4(6) . . . . ? I1 N2 C7 O8 0.8(9) . . . . ? C3 N2 C7 C6 -1.1(8) . . . . ? I1 N2 C7 C6 -179.6(4) . . . . ? C5 C6 C7 O8 179.8(7) . . . . ? C5 C6 C7 N2 0.2(7) . . . . ? N17 I9 N10 C15 0E1(2) . . . . ? N17 I9 N10 C11 18E1(10) . . . . ? C15 N10 C11 O12 178.7(7) . . . . ? I9 N10 C11 O12 1.2(9) . . . . ? C15 N10 C11 C13 -1.1(8) . . . . ? I9 N10 C11 C13 -178.6(4) . . . . ? O12 C11 C13 C14 -178.4(7) . . . . ? N10 C11 C13 C14 1.4(7) . . . . ? C11 C13 C14 C15 -1.2(7) . . . . ? C11 N10 C15 O16 179.8(6) . . . . ? I9 N10 C15 O16 -2.8(10) . . . . ? C11 N10 C15 C14 0.2(8) . . . . ? I9 N10 C15 C14 177.7(4) . . . . ? C13 C14 C15 O16 -178.9(7) . . . . ? C13 C14 C15 N10 0.6(8) . . . . ? N10 I9 N17 C21 -0E1(2) . . . 6 ? N10 I9 N17 C18 -12E1(2) . . . . ? N10 I9 N17 C22 12E1(2) . . . . ? C21 N17 C18 N19 60.0(4) 6 . . . ? C22 N17 C18 N19 -60.1(4) . . . . ? I9 N17 C18 N19 178.7(3) . . . . ? N17 C18 N19 C20 -59.0(4) . . . . ? N17 C18 N19 C21 59.7(4) . . . . ? N17 C18 N19 I1 173.1(3) . . . . ? N2 I1 N19 C20 108(2) . . . . ? N2 I1 N19 C21 -10(2) . . . . ? N2 I1 N19 C18 -127(2) . . . . ? C21 N19 C20 N19 -59.5(2) . . . 6 ? C18 N19 C20 N19 59.5(2) . . . 6 ? I1 N19 C20 N19 -173.9(2) . . . 6 ? C20 N19 C21 N17 59.6(4) . . . 6 ? C18 N19 C21 N17 -59.5(4) . . . 6 ? I1 N19 C21 N17 -178.8(3) . . . 6 ? C21 N17 C22 N17 -59.7(2) 6 . . 6 ? C18 N17 C22 N17 60.2(3) . . . 6 ? I9 N17 C22 N17 -177.5(2) . . . 6 ? data_MeNO2_NIS-HMTA _database_code_depnum_ccdc_archive 'CCDC 855774' _audit_creation_date 2009-11-06T15:39:00-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H12 N4, 4(C4 H4 I N O2), 4(C H3 N O2)' _chemical_formula_sum 'C26 H40 I4 N12 O16' _chemical_formula_weight 1284.3 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'I -4 c 2' _symmetry_space_group_name_Hall 'I -4 -2c' _symmetry_Int_Tables_number 120 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, -x, -z+1/2' 'y, x, -z+1/2' '-x, y, z+1/2' 'x, -y, z+1/2' '-y, x, -z' 'y, -x, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-y+1/2, -x+1/2, -z+1' 'y+1/2, x+1/2, -z+1' '-x+1/2, y+1/2, z+1' 'x+1/2, -y+1/2, z+1' '-y+1/2, x+1/2, -z+1/2' 'y+1/2, -x+1/2, -z+1/2' _cell_length_a 16.8566(2) _cell_length_b 16.8566(2) _cell_length_c 14.5819(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4143.37(11) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2279 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.283 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 2.059 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2480 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.5611 _exptl_absorpt_correction_T_max 0.7456 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.527894E-1 _diffrn_orient_matrix_ub_12 0.104549E-1 _diffrn_orient_matrix_ub_13 0.288607E-1 _diffrn_orient_matrix_ub_21 0.211024E-1 _diffrn_orient_matrix_ub_22 -0.501643E-1 _diffrn_orient_matrix_ub_23 -0.272962E-1 _diffrn_orient_matrix_ub_31 0.01695 _diffrn_orient_matrix_ub_32 0.298925E-1 _diffrn_orient_matrix_ub_33 -0.559012E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_unetI/netI 0.04 _diffrn_reflns_number 9984 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.974 _reflns_number_total 2236 _reflns_number_gt 2052 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _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^)+(0.0169P)^2^+5.0560P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2236 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0308 _refine_ls_R_factor_gt 0.026 _refine_ls_wR_factor_ref 0.0488 _refine_ls_wR_factor_gt 0.0477 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(3) _refine_diff_density_max 0.534 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.097 #----------------------------------------------------------------------------# # 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' 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' 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 0.689386(12) 0.980908(13) 0.58252(2) 0.01804(8) Uani 1 1 d . . . N2 N 0.7809(2) 0.97147(19) 0.4836(2) 0.0188(7) Uani 1 1 d . . . C3 C 0.7723(2) 0.9995(2) 0.3953(3) 0.0187(9) Uani 1 1 d . . . O4 O 0.71557(17) 1.03797(17) 0.3692(2) 0.0254(7) Uani 1 1 d . . . C5 C 0.8423(3) 0.9732(3) 0.3388(3) 0.0237(10) Uani 1 1 d . . . H5A H 0.8718 1.0195 0.3146 0.028 Uiso 1 1 calc R . . H5B H 0.8249 0.9398 0.2867 0.028 Uiso 1 1 calc R . . C6 C 0.8933(2) 0.9258(2) 0.4049(3) 0.0257(10) Uani 1 1 d . . . H6A H 0.9001 0.8706 0.3829 0.031 Uiso 1 1 calc R . . H6B H 0.9464 0.9504 0.4115 0.031 Uiso 1 1 calc R . . C7 C 0.8493(2) 0.9271(2) 0.4953(3) 0.0197(9) Uani 1 1 d . . . O8 O 0.86877(15) 0.89573(17) 0.5663(2) 0.0303(8) Uani 1 1 d . . . N9 N 0.57181(17) 0.99180(19) 0.6909(2) 0.0164(7) Uani 1 1 d . . . C10 C 0.5799(2) 1.0632(2) 0.7510(3) 0.0162(8) Uani 1 1 d . . . H10A H 0.6274 1.0576 0.7904 0.019 Uiso 1 1 calc R . . H10B H 0.5867 1.1112 0.7127 0.019 Uiso 1 1 calc R . . C11 C 0.5 1 0.6336(4) 0.0171(11) Uani 1 2 d S . . H11A H 0.4946 0.9528 0.5937 0.02 Uiso 0.5 1 calc PR . . H11B H 0.5054 1.0472 0.5937 0.02 Uiso 0.5 1 calc PR . . C12 C 0.7980(3) 0.7020(3) 0.5 0.050(2) Uani 1 2 d S . . H12A H 0.8237 0.7003 0.4398 0.075 Uiso 0.5 1 calc PR . . H12B H 0.7737 0.6504 0.5131 0.075 Uiso 0.5 1 calc PR . . H12C H 0.8376 0.7142 0.5471 0.075 Uiso 0.5 1 calc PR . . N13 N 0.7359(3) 0.7641(3) 0.5 0.0427(15) Uani 1 2 d S . . O14 O 0.7306(2) 0.8075(2) 0.4333(3) 0.0586(12) Uani 1 1 d . . . C15 C 0.8003(2) 0.8003(2) 0.75 0.0291(14) Uani 1 2 d S . . H15A H 0.7798 0.8481 0.7201 0.044 Uiso 0.5 1 calc PR . . H15B H 0.8469 0.781 0.7166 0.044 Uiso 0.5 1 calc PR . . H15C H 0.8152 0.8127 0.8133 0.044 Uiso 0.5 1 calc PR . . N16 N 0.7384(2) 0.7384(2) 0.75 0.0431(16) Uani 1 2 d S . . O17 O 0.7569(2) 0.6707(2) 0.7254(3) 0.0549(11) 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 0.01412(12) 0.01712(12) 0.02289(12) 0.00115(11) 0.00081(13) 0.00096(9) N2 0.0149(16) 0.0169(17) 0.0247(19) -0.0009(15) 0.0009(16) 0.0027(13) C3 0.019(2) 0.0178(18) 0.020(2) -0.0006(16) -0.0025(16) -0.0020(17) O4 0.0199(14) 0.0278(15) 0.0284(16) 0.0051(13) -0.0066(12) 0.0025(12) C5 0.027(2) 0.022(3) 0.022(2) -0.0033(19) -0.001(2) 0.0005(16) C6 0.0210(19) 0.027(2) 0.029(3) -0.003(2) 0.008(2) 0.0052(17) C7 0.014(2) 0.016(2) 0.029(2) 0.0031(18) -0.0035(18) -0.0016(18) O8 0.0221(14) 0.0343(16) 0.034(2) 0.0086(14) -0.0001(14) 0.0089(12) N9 0.0122(15) 0.0171(16) 0.0200(19) 0.0014(14) -0.0024(14) -0.0013(13) C10 0.0138(18) 0.0134(18) 0.021(2) -0.0016(16) 0.0010(17) -0.0029(15) C11 0.016(3) 0.020(3) 0.015(3) 0 0 0.002(3) C12 0.042(3) 0.042(3) 0.065(6) 0.009(3) 0.009(3) 0.015(4) N13 0.036(2) 0.036(2) 0.056(4) -0.003(2) -0.003(2) -0.006(3) O14 0.073(3) 0.041(2) 0.062(3) -0.002(2) -0.024(2) 0.003(2) C15 0.0238(19) 0.0238(19) 0.040(4) 0.004(2) -0.004(2) -0.003(3) N16 0.0261(19) 0.0261(19) 0.077(5) -0.004(2) 0.004(2) 0.005(2) O17 0.048(2) 0.0255(19) 0.091(3) -0.005(2) 0.017(2) -0.0004(16) #----------------------------------------------------------------------------# # 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 N2 2.118(3) . ? N2 C3 1.379(5) . ? N2 C7 1.385(5) . ? C3 O4 1.217(5) . ? C3 C5 1.506(6) . ? C5 C6 1.520(6) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.513(6) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 O8 1.208(5) . ? N9 C11 1.477(4) . ? N9 C10 1.484(5) 16_466 ? N9 C10 1.495(5) . ? C10 N9 1.484(5) 15_656 ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 N9 1.477(4) 2_675 ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 N13 1.480(10) . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? N13 O14 1.220(5) . ? N13 O14 1.220(5) 11_665 ? C15 N16 1.476(8) . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? N16 O17 1.235(4) . ? N16 O17 1.235(4) 4_556 ? 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 C3 N2 C7 112.8(3) . . ? C3 N2 I1 122.3(3) . . ? C7 N2 I1 124.3(3) . . ? O4 C3 N2 123.9(4) . . ? O4 C3 C5 126.9(4) . . ? N2 C3 C5 109.1(3) . . ? C3 C5 C6 104.5(3) . . ? C3 C5 H5A 110.8 . . ? C6 C5 H5A 110.8 . . ? C3 C5 H5B 110.8 . . ? C6 C5 H5B 110.8 . . ? H5A C5 H5B 108.9 . . ? C7 C6 C5 105.5(3) . . ? C7 C6 H6A 110.6 . . ? C5 C6 H6A 110.6 . . ? C7 C6 H6B 110.6 . . ? C5 C6 H6B 110.6 . . ? H6A C6 H6B 108.8 . . ? O8 C7 N2 124.6(4) . . ? O8 C7 C6 127.3(3) . . ? N2 C7 C6 108.0(3) . . ? C11 N9 C10 108.6(3) . 16_466 ? C11 N9 C10 109.3(3) . . ? C10 N9 C10 109.2(2) 16_466 . ? N9 C10 N9 109.8(3) 15_656 . ? N9 C10 H10A 109.7 15_656 . ? N9 C10 H10A 109.7 . . ? N9 C10 H10B 109.7 15_656 . ? N9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? N9 C11 N9 111.2(4) . 2_675 ? N9 C11 H11A 109.4 . . ? N9 C11 H11A 109.4 2_675 . ? N9 C11 H11B 109.4 . . ? N9 C11 H11B 109.4 2_675 . ? H11A C11 H11B 108 . . ? N13 C12 H12A 109.5 . . ? N13 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N13 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O14 N13 O14 123.2(7) . 11_665 ? O14 N13 C12 118.4(3) . . ? O14 N13 C12 118.4(3) 11_665 . ? N16 C15 H15A 109.5 . . ? N16 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N16 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O17 N16 O17 123.5(5) . 4_556 ? O17 N16 C15 118.3(3) . . ? O17 N16 C15 118.3(3) 4_556 . ? 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 C7 N2 C3 O4 178.0(4) . . . . ? I1 N2 C3 O4 7.0(5) . . . . ? C7 N2 C3 C5 -0.8(4) . . . . ? I1 N2 C3 C5 -171.7(3) . . . . ? O4 C3 C5 C6 -178.5(4) . . . . ? N2 C3 C5 C6 0.1(4) . . . . ? C3 C5 C6 C7 0.5(4) . . . . ? C3 N2 C7 O8 -179.0(4) . . . . ? I1 N2 C7 O8 -8.3(6) . . . . ? C3 N2 C7 C6 1.1(4) . . . . ? I1 N2 C7 C6 171.8(2) . . . . ? C5 C6 C7 O8 179.2(4) . . . . ? C5 C6 C7 N2 -0.9(4) . . . . ? C11 N9 C10 N9 58.3(4) . . . 15_656 ? C10 N9 C10 N9 -60.4(3) 16_466 . . 15_656 ? C10 N9 C11 N9 60.0(2) 16_466 . . 2_675 ? C10 N9 C11 N9 -59.1(2) . . . 2_675 ? data_Tolu_NIS-HMTA _database_code_depnum_ccdc_archive 'CCDC 855775' _audit_creation_date 2010-10-28T10:22:00-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H12 N4, C7 H8, 4(C4 H4 I N O2)' _chemical_formula_sum 'C29 H36 I4 N8 O8' _chemical_formula_weight 1132.26 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.0769(5) _cell_length_b 7.06250(10) _cell_length_c 20.9842(4) _cell_angle_alpha 90 _cell_angle_beta 108.6220(10) _cell_angle_gamma 90 _cell_volume 3662.29(11) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4485 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.7 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 2.054 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2168 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.462 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.6055 _exptl_absorpt_correction_T_max 0.7457 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.128985E-1 _diffrn_orient_matrix_ub_12 0.326441E-1 _diffrn_orient_matrix_ub_13 -0.386943E-1 _diffrn_orient_matrix_ub_21 0.36312E-1 _diffrn_orient_matrix_ub_22 0.338437E-1 _diffrn_orient_matrix_ub_23 0.320912E-1 _diffrn_orient_matrix_ub_31 0.123542E-1 _diffrn_orient_matrix_ub_32 -0.133557 _diffrn_orient_matrix_ub_33 -0.13257E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_unetI/netI 0.0347 _diffrn_reflns_number 15851 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3 _diffrn_reflns_theta_max 28.52 _diffrn_reflns_theta_full 28.52 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _reflns_number_total 4606 _reflns_number_gt 4076 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _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^)+(0.0000P)^2^+16.2220P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4606 _refine_ls_number_parameters 209 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0316 _refine_ls_R_factor_gt 0.0259 _refine_ls_wR_factor_ref 0.055 _refine_ls_wR_factor_gt 0.053 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.879 _refine_diff_density_min -0.602 _refine_diff_density_rms 0.117 #----------------------------------------------------------------------------# # 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' 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' 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 0.538020(7) 0.17865(3) 0.916081(9) 0.01756(5) Uani 1 1 d . . . N2 N 0.56618(10) -0.0011(3) 0.99934(12) 0.0184(5) Uani 1 1 d . . . C3 C 0.56983(13) -0.1938(4) 0.99174(16) 0.0233(6) Uani 1 1 d . . . O4 O 0.55157(12) -0.2769(4) 0.93880(12) 0.0393(7) Uani 1 1 d . . . C5 C 0.60020(14) -0.2790(4) 1.05944(16) 0.0258(7) Uani 1 1 d . . . H5A H 0.6339 -0.3414 1.0582 0.031 Uiso 1 1 calc R . . H5B H 0.5775 -0.3732 1.073 0.031 Uiso 1 1 calc R . . C6 C 0.61298(13) -0.1112(4) 1.10771(16) 0.0240(7) Uani 1 1 d . . . H6A H 0.5966 -0.1293 1.1438 0.029 Uiso 1 1 calc R . . H6B H 0.6526 -0.0962 1.1285 0.029 Uiso 1 1 calc R . . C7 C 0.58893(12) 0.0597(4) 1.06548(15) 0.0206(6) Uani 1 1 d . . . O8 O 0.58895(10) 0.2215(3) 1.08361(12) 0.0330(6) Uani 1 1 d . . . I9 I 0.369541(7) 0.84523(2) 0.718523(9) 0.01611(5) Uani 1 1 d . . . N10 N 0.30203(9) 1.0256(3) 0.69201(12) 0.0175(5) Uani 1 1 d . . . C11 C 0.30430(12) 1.2169(4) 0.70632(15) 0.0186(6) Uani 1 1 d . . . O12 O 0.34560(9) 1.3017(3) 0.73494(12) 0.0258(5) Uani 1 1 d . . . C13 C 0.24755(13) 1.2960(5) 0.68097(17) 0.0257(7) Uani 1 1 d . . . H13A H 0.2455 1.4025 0.6496 0.031 Uiso 1 1 calc R . . H13B H 0.236 1.3416 0.7188 0.031 Uiso 1 1 calc R . . C14 C 0.21216(13) 1.1315(5) 0.64499(18) 0.0282(7) Uani 1 1 d . . . H14A H 0.1828 1.1072 0.6643 0.034 Uiso 1 1 calc R . . H14B H 0.1959 1.1587 0.5964 0.034 Uiso 1 1 calc R . . C15 C 0.25001(12) 0.9640(4) 0.65610(15) 0.0209(6) Uani 1 1 d . . . O16 O 0.23856(9) 0.8022(3) 0.63833(12) 0.0304(5) Uani 1 1 d . . . N17 N 0.54794(9) 0.6315(3) 0.75558(12) 0.0145(5) Uani 1 1 d . . . C18 C 0.5 0.7494(5) 0.75 0.0176(8) Uani 1 2 d S . . H18A H 0.5075 0.8318 0.7901 0.021 Uiso 0.5 1 calc PR . . H18B H 0.4925 0.8318 0.7099 0.021 Uiso 0.5 1 calc PR . . C19 C 0.53617(11) 0.5117(4) 0.69437(14) 0.0155(5) Uani 1 1 d . . . H19A H 0.5681 0.4325 0.6968 0.019 Uiso 1 1 calc R . . H19B H 0.5284 0.5932 0.654 0.019 Uiso 1 1 calc R . . C20 C 0.55883(11) 0.5080(4) 0.81528(13) 0.0148(5) Uani 1 1 d . . . H20A H 0.5677 0.587 0.8563 0.018 Uiso 1 1 calc R . . H20B H 0.5904 0.4263 0.8186 0.018 Uiso 1 1 calc R . . N21 N 0.48873(9) 0.3884(3) 0.68912(11) 0.0140(5) Uani 1 1 d . . . C22 C 0.5 0.2690(5) 0.75 0.0164(8) Uani 1 2 d S . . H22A H 0.4684 0.1867 0.7462 0.02 Uiso 0.5 1 calc PR . . H22B H 0.5316 0.1867 0.7538 0.02 Uiso 0.5 1 calc PR . . C23 C 0.1975(4) 1.5524(15) 0.4825(5) 0.066(3) Uiso 0.5 1 d PD A -1 H23A H 0.2017 1.5998 0.5278 0.1 Uiso 0.5 1 calc PR A -1 H23B H 0.1589 1.5391 0.4574 0.1 Uiso 0.5 1 calc PR A -1 H23C H 0.214 1.6418 0.4591 0.1 Uiso 0.5 1 calc PR A -1 C24 C 0.2240(2) 1.3684(5) 0.4872(3) 0.0383(17) Uiso 0.5 1 d PG A -1 C25 C 0.2773(2) 1.3474(6) 0.5280(3) 0.051(2) Uiso 0.5 1 d PGD A -1 H25 H 0.2967 1.4531 0.5519 0.061 Uiso 0.5 1 calc PR A -1 C26 C 0.30244(17) 1.1717(8) 0.5338(3) 0.052(2) Uiso 0.5 1 d PG A -1 H26 H 0.3389 1.1573 0.5616 0.063 Uiso 0.5 1 calc PR A -1 C27 C 0.2741(2) 1.0170(6) 0.4987(3) 0.053(2) Uiso 0.5 1 d PG A -1 H27 H 0.2913 0.8969 0.5027 0.063 Uiso 0.5 1 calc PR A -1 C28 C 0.2208(2) 1.0380(6) 0.4579(3) 0.053(2) Uiso 0.5 1 d PG A -1 H28 H 0.2014 0.9323 0.434 0.063 Uiso 0.5 1 calc PR A -1 C29 C 0.19566(16) 1.2137(7) 0.4521(2) 0.0348(16) Uiso 0.5 1 d PGD A -1 H29 H 0.1592 1.2281 0.4243 0.042 Uiso 0.5 1 calc PR A -1 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 0.01604(10) 0.02024(9) 0.01543(10) 0.00349(7) 0.00365(7) 0.00162(7) N2 0.0229(13) 0.0179(11) 0.0121(11) 0.0034(9) 0.0025(10) 0.0015(10) C3 0.0288(17) 0.0220(15) 0.0202(15) 0.0011(12) 0.0096(14) 0.0051(13) O4 0.0648(19) 0.0284(13) 0.0202(13) -0.0058(10) 0.0070(13) 0.0075(12) C5 0.0297(17) 0.0240(15) 0.0217(16) 0.0043(13) 0.0055(14) 0.0094(13) C6 0.0229(16) 0.0264(15) 0.0183(15) 0.0058(12) 0.0003(13) 0.0003(13) C7 0.0157(14) 0.0259(15) 0.0172(14) -0.0007(12) 0.0011(12) -0.0046(12) O8 0.0460(15) 0.0206(11) 0.0246(12) -0.0025(9) 0.0004(11) -0.0048(11) I9 0.01359(9) 0.01692(9) 0.01696(10) 0.00073(7) 0.00368(7) 0.00127(7) N10 0.0120(11) 0.0176(11) 0.0205(12) 0.0004(10) 0.0019(10) 0.0031(9) C11 0.0205(15) 0.0179(13) 0.0174(14) 0.0020(11) 0.0059(12) -0.0003(12) O12 0.0237(12) 0.0199(10) 0.0309(13) -0.0006(9) 0.0047(10) -0.0035(9) C13 0.0196(15) 0.0248(15) 0.0314(18) -0.0006(13) 0.0060(14) 0.0084(13) C14 0.0167(15) 0.0362(18) 0.0281(18) -0.0039(14) 0.0020(14) 0.0053(14) C15 0.0152(14) 0.0281(16) 0.0175(14) 0.0001(12) 0.0026(12) 0.0021(12) O16 0.0214(12) 0.0269(12) 0.0381(14) -0.0086(10) 0.0029(11) -0.0028(10) N17 0.0121(11) 0.0153(11) 0.0154(12) -0.0002(9) 0.0035(10) 0.0006(9) C18 0.019(2) 0.0113(17) 0.022(2) 0 0.0063(17) 0 C19 0.0146(13) 0.0177(13) 0.0151(13) -0.0020(11) 0.0058(11) -0.0004(11) C20 0.0128(13) 0.0181(13) 0.0115(12) -0.0002(10) 0.0013(10) 0.0006(11) N21 0.0142(11) 0.0160(11) 0.0107(11) -0.0016(9) 0.0022(9) 0.0000(9) C22 0.020(2) 0.0122(17) 0.0149(19) 0 0.0027(17) 0 #----------------------------------------------------------------------------# # 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 N2 2.094(2) . ? N2 C3 1.377(4) . ? N2 C7 1.392(4) . ? C3 O4 1.211(4) . ? C3 C5 1.513(4) . ? C5 C6 1.525(4) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.510(4) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 O8 1.204(4) . ? I9 N10 2.099(2) . ? N10 C11 1.382(4) . ? N10 C15 1.394(4) . ? C11 O12 1.211(4) . ? C11 C13 1.510(4) . ? C13 C14 1.526(5) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.510(4) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 O16 1.209(4) . ? N17 C18 1.476(3) . ? N17 C20 1.477(3) . ? N17 C19 1.486(3) . ? C18 N17 1.476(3) 2_656 ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? C19 N21 1.488(3) . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? C20 N21 1.479(3) 2_656 ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? N21 C20 1.479(3) 2_656 ? N21 C22 1.480(3) . ? C22 N21 1.480(3) 2_656 ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? C23 C24 1.460(11) . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? C24 C25 1.39 . ? C24 C29 1.39 . ? C25 C26 1.39 . ? C25 H25 0.95 . ? C26 C27 1.39 . ? C26 H26 0.95 . ? C27 C28 1.39 . ? C27 H27 0.95 . ? C28 C29 1.39 . ? C28 H28 0.95 . ? C29 H29 0.95 . ? 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 C3 N2 C7 113.4(2) . . ? C3 N2 I1 121.42(19) . . ? C7 N2 I1 124.7(2) . . ? O4 C3 N2 124.3(3) . . ? O4 C3 C5 127.1(3) . . ? N2 C3 C5 108.6(3) . . ? C3 C5 C6 104.6(2) . . ? C3 C5 H5A 110.8 . . ? C6 C5 H5A 110.8 . . ? C3 C5 H5B 110.8 . . ? C6 C5 H5B 110.8 . . ? H5A C5 H5B 108.9 . . ? C7 C6 C5 105.7(2) . . ? C7 C6 H6A 110.6 . . ? C5 C6 H6A 110.6 . . ? C7 C6 H6B 110.6 . . ? C5 C6 H6B 110.6 . . ? H6A C6 H6B 108.7 . . ? O8 C7 N2 124.4(3) . . ? O8 C7 C6 127.9(3) . . ? N2 C7 C6 107.6(3) . . ? C11 N10 C15 112.9(2) . . ? C11 N10 I9 124.2(2) . . ? C15 N10 I9 122.88(19) . . ? O12 C11 N10 124.1(3) . . ? O12 C11 C13 127.4(3) . . ? N10 C11 C13 108.4(3) . . ? C11 C13 C14 105.2(2) . . ? C11 C13 H13A 110.7 . . ? C14 C13 H13A 110.7 . . ? C11 C13 H13B 110.7 . . ? C14 C13 H13B 110.7 . . ? H13A C13 H13B 108.8 . . ? C15 C14 C13 104.9(3) . . ? C15 C14 H14A 110.8 . . ? C13 C14 H14A 110.8 . . ? C15 C14 H14B 110.8 . . ? C13 C14 H14B 110.8 . . ? H14A C14 H14B 108.8 . . ? O16 C15 N10 124.3(3) . . ? O16 C15 C14 127.4(3) . . ? N10 C15 C14 108.3(3) . . ? C18 N17 C20 109.20(19) . . ? C18 N17 C19 108.47(19) . . ? C20 N17 C19 109.1(2) . . ? N17 C18 N17 111.3(3) 2_656 . ? N17 C18 H18A 109.4 2_656 . ? N17 C18 H18A 109.4 . . ? N17 C18 H18B 109.4 2_656 . ? N17 C18 H18B 109.4 . . ? H18A C18 H18B 108 . . ? N17 C19 N21 109.6(2) . . ? N17 C19 H19A 109.8 . . ? N21 C19 H19A 109.8 . . ? N17 C19 H19B 109.8 . . ? N21 C19 H19B 109.8 . . ? H19A C19 H19B 108.2 . . ? N17 C20 N21 110.7(2) . 2_656 ? N17 C20 H20A 109.5 . . ? N21 C20 H20A 109.5 2_656 . ? N17 C20 H20B 109.5 . . ? N21 C20 H20B 109.5 2_656 . ? H20A C20 H20B 108.1 . . ? C20 N21 C22 108.10(18) 2_656 . ? C20 N21 C19 109.3(2) 2_656 . ? C22 N21 C19 109.77(19) . . ? N21 C22 N21 110.6(3) 2_656 . ? N21 C22 H22A 109.5 2_656 . ? N21 C22 H22A 109.5 . . ? N21 C22 H22B 109.5 2_656 . ? N21 C22 H22B 109.5 . . ? H22A C22 H22B 108.1 . . ? C25 C24 C29 120 . . ? C25 C24 C23 119.7(5) . . ? C29 C24 C23 120.3(5) . . ? C26 C25 C24 120 . . ? C26 C25 H25 120 . . ? C24 C25 H25 120 . . ? C25 C26 C27 120 . . ? C25 C26 H26 120 . . ? C27 C26 H26 120 . . ? C28 C27 C26 120 . . ? C28 C27 H27 120 . . ? C26 C27 H27 120 . . ? C27 C28 C29 120 . . ? C27 C28 H28 120 . . ? C29 C28 H28 120 . . ? C28 C29 C24 120 . . ? C28 C29 H29 120 . . ? C24 C29 H29 120 . . ? 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 C7 N2 C3 O4 178.2(3) . . . . ? I1 N2 C3 O4 -9.3(5) . . . . ? C7 N2 C3 C5 -2.2(4) . . . . ? I1 N2 C3 C5 170.34(19) . . . . ? O4 C3 C5 C6 -179.5(3) . . . . ? N2 C3 C5 C6 0.9(3) . . . . ? C3 C5 C6 C7 0.5(3) . . . . ? C3 N2 C7 O8 -178.0(3) . . . . ? I1 N2 C7 O8 9.7(4) . . . . ? C3 N2 C7 C6 2.5(3) . . . . ? I1 N2 C7 C6 -169.72(19) . . . . ? C5 C6 C7 O8 178.8(3) . . . . ? C5 C6 C7 N2 -1.8(3) . . . . ? C15 N10 C11 O12 -177.3(3) . . . . ? I9 N10 C11 O12 1.0(4) . . . . ? C15 N10 C11 C13 3.2(3) . . . . ? I9 N10 C11 C13 -178.48(19) . . . . ? O12 C11 C13 C14 176.1(3) . . . . ? N10 C11 C13 C14 -4.4(3) . . . . ? C11 C13 C14 C15 4.0(3) . . . . ? C11 N10 C15 O16 -179.8(3) . . . . ? I9 N10 C15 O16 1.8(4) . . . . ? C11 N10 C15 C14 -0.5(3) . . . . ? I9 N10 C15 C14 -178.90(19) . . . . ? C13 C14 C15 O16 177.0(3) . . . . ? C13 C14 C15 N10 -2.3(3) . . . . ? C20 N17 C18 N17 -58.75(16) . . . 2_656 ? C19 N17 C18 N17 60.09(16) . . . 2_656 ? C18 N17 C19 N21 -60.2(3) . . . . ? C20 N17 C19 N21 58.7(3) . . . . ? C18 N17 C20 N21 57.8(3) . . . 2_656 ? C19 N17 C20 N21 -60.7(3) . . . 2_656 ? N17 C19 N21 C20 60.0(3) . . . 2_656 ? N17 C19 N21 C22 -58.4(3) . . . . ? C20 N21 C22 N21 -59.68(16) 2_656 . . 2_656 ? C19 N21 C22 N21 59.48(16) . . . 2_656 ? C29 C24 C25 C26 0 . . . . ? C23 C24 C25 C26 178.7(7) . . . . ? C24 C25 C26 C27 0 . . . . ? C25 C26 C27 C28 0 . . . . ? C26 C27 C28 C29 0 . . . . ? C27 C28 C29 C24 0 . . . . ? C25 C24 C29 C28 0 . . . . ? C23 C24 C29 C28 -178.7(7) . . . . ? #END