Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Pierangelo Metrangolo' Nanoscience Center, 'S Biella' of Chemistry, 'Manu Lahtinen' of Jyvaskyla, 'Rosalba Liantonio' O. Box 'Giuseppe Resnati' 40014 Jyv\"askyl\"a, ; K.Rissanen ; ; 'Biella Serena' ; NFMLab 'Luca Russo' G. Natta, _publ_contact_author_name 'Pierangelo Metrangolo' _publ_contact_author_address ; Dipartimento di Chimica, Materiali ed Ingegneria Chimica "G. Natta" Politecnico di Milano Via L. Mancinelli 7 Milano I-20131 ITALY ; _publ_contact_author_email PIERANGELO.METRANGOLO@POLIMI.IT _publ_section_title ; Solution stoichiometry determines crystal stoichiometry in halogenbonded supramolecular complexes ; data_lrs007 _database_code_depnum_ccdc_archive 'CCDC 630671' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 F4 I2,C7 H7 O2' _chemical_formula_sum 'C13 H7 F4 I2 N O2' _chemical_formula_weight 539.00 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4055(13) _cell_length_b 9.589(2) _cell_length_c 13.479(5) _cell_angle_alpha 78.22(3) _cell_angle_beta 86.37(3) _cell_angle_gamma 73.407(15) _cell_volume 776.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2428 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 4.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1925 _exptl_absorpt_correction_T_max 0.8214 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11047 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 27.59 _reflns_number_total 3558 _reflns_number_gt 2970 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement EvalCCD _computing_data_reduction EvalCCD _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 1.4, Diamond 3' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0121P)^2^+0.1306P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3558 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0459 _refine_ls_wR_factor_gt 0.0415 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _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 C1 C 0.3009(5) 0.5606(4) 0.7199(3) 0.0325(8) Uani 1 1 d . . . H1B H 0.4519 0.5239 0.7351 0.039 Uiso 1 1 calc R . . C2 C 0.1793(5) 0.6806(3) 0.7600(2) 0.0285(7) Uani 1 1 d . . . H2A H 0.2455 0.7257 0.8009 0.034 Uiso 1 1 calc R . . C3 C -0.0437(5) 0.7340(3) 0.7389(2) 0.0218(7) Uani 1 1 d . . . C4 C -0.1320(5) 0.6638(3) 0.6784(2) 0.0278(7) Uani 1 1 d . . . H4A H -0.2831 0.6967 0.6631 0.033 Uiso 1 1 calc R . . C5 C 0.0043(5) 0.5449(4) 0.6406(3) 0.0316(8) Uani 1 1 d . . . H5A H -0.0570 0.4985 0.5987 0.038 Uiso 1 1 calc R . . C6 C -0.1791(5) 0.8636(3) 0.7833(2) 0.0244(7) Uani 1 1 d . . . C7 C -0.5390(5) 0.9928(4) 0.8265(3) 0.0356(9) Uani 1 1 d . . . H7A H -0.6888 0.9870 0.8239 0.053 Uiso 1 1 calc R . . H7B H -0.5279 1.0881 0.7867 0.053 Uiso 1 1 calc R . . H7C H -0.4996 0.9842 0.8970 0.053 Uiso 1 1 calc R . . C8 C -0.0432(5) 1.3943(3) 0.9499(2) 0.0232(7) Uani 1 1 d . . . C9 C -0.2007(5) 1.5257(3) 0.9582(2) 0.0233(7) Uani 1 1 d . . . C10 C 0.1599(5) 1.3727(3) 0.9917(2) 0.0225(7) Uani 1 1 d . . . C11 C 0.8245(5) 0.1142(3) 0.5271(2) 0.0210(7) Uani 1 1 d . . . C12 C 1.0301(5) 0.0795(3) 0.5696(2) 0.0226(7) Uani 1 1 d . . . C13 C 0.7992(5) 0.0332(3) 0.4567(2) 0.0226(7) Uani 1 1 d . . . N1 N 0.2178(4) 0.4928(3) 0.6605(2) 0.0312(7) Uani 1 1 d . . . O1 O -0.1010(4) 0.9472(3) 0.8153(2) 0.0430(7) Uani 1 1 d . . . O2 O -0.3905(3) 0.8718(2) 0.78428(17) 0.0309(5) Uani 1 1 d . . . I1 I 0.56191(3) 0.27823(2) 0.573814(16) 0.02538(7) Uani 1 1 d . . . I2 I -0.10652(4) 1.23284(2) 0.882348(17) 0.03442(7) Uani 1 1 d . . . F1 F -0.3995(3) 1.5564(2) 0.91567(14) 0.0332(4) Uani 1 1 d . . . F2 F 0.3220(3) 1.24808(19) 0.98488(14) 0.0347(5) Uani 1 1 d . . . F3 F 1.0674(3) 0.1554(2) 0.63782(14) 0.0332(5) Uani 1 1 d . . . F4 F 0.6030(3) 0.0646(2) 0.41125(14) 0.0318(4) 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 C1 0.0199(17) 0.0337(19) 0.042(2) -0.0104(17) -0.0005(15) -0.0021(15) C2 0.0278(18) 0.0297(18) 0.0315(19) -0.0114(15) -0.0029(14) -0.0088(15) C3 0.0246(16) 0.0213(16) 0.0200(16) -0.0062(13) 0.0020(13) -0.0063(13) C4 0.0202(16) 0.0319(18) 0.0321(19) -0.0120(15) -0.0021(14) -0.0041(14) C5 0.0291(19) 0.0372(19) 0.034(2) -0.0196(16) 0.0012(15) -0.0099(16) C6 0.0243(17) 0.0240(17) 0.0225(17) -0.0041(14) -0.0002(13) -0.0033(14) C7 0.0299(19) 0.0298(18) 0.040(2) -0.0114(16) 0.0050(16) 0.0051(15) C8 0.0305(18) 0.0221(16) 0.0184(16) -0.0061(13) 0.0000(13) -0.0081(14) C9 0.0199(16) 0.0282(17) 0.0217(17) -0.0051(14) -0.0023(13) -0.0059(14) C10 0.0235(16) 0.0194(15) 0.0224(17) -0.0061(13) 0.0031(13) -0.0017(13) C11 0.0207(16) 0.0176(15) 0.0230(17) -0.0047(13) 0.0013(13) -0.0027(13) C12 0.0275(18) 0.0218(16) 0.0214(17) -0.0107(13) 0.0011(13) -0.0070(14) C13 0.0188(16) 0.0234(16) 0.0240(17) -0.0036(13) -0.0031(13) -0.0036(13) N1 0.0277(15) 0.0294(15) 0.0371(17) -0.0137(13) 0.0071(13) -0.0054(13) O1 0.0364(14) 0.0372(14) 0.0661(19) -0.0323(14) 0.0035(12) -0.0127(12) O2 0.0231(12) 0.0320(13) 0.0389(14) -0.0195(11) 0.0007(10) -0.0011(10) I1 0.02221(11) 0.02108(11) 0.03107(13) -0.00957(9) 0.00303(9) -0.00075(9) I2 0.03731(14) 0.03289(13) 0.04023(15) -0.02058(11) 0.00173(10) -0.01210(11) F1 0.0235(10) 0.0379(11) 0.0376(11) -0.0104(9) -0.0080(8) -0.0038(8) F2 0.0291(10) 0.0257(10) 0.0435(12) -0.0140(9) -0.0018(9) 0.0068(8) F3 0.0285(10) 0.0387(11) 0.0377(11) -0.0247(9) -0.0018(8) -0.0053(9) F4 0.0207(9) 0.0377(11) 0.0357(11) -0.0146(9) -0.0067(8) 0.0003(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 H1B 0.9500 . ? C1 C2 1.383(4) . ? C1 N1 1.346(4) . ? C2 H2A 0.9500 . ? C2 C3 1.399(4) . ? C3 C4 1.392(4) . ? C3 C6 1.509(4) . ? C4 H4A 0.9500 . ? C4 C5 1.391(4) . ? C5 H5A 0.9500 . ? C5 N1 1.339(4) . ? C6 O1 1.216(4) . ? C6 O2 1.333(4) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7 O2 1.464(4) . ? C8 C9 1.391(4) . ? C8 C10 1.394(4) . ? C8 I2 2.091(3) . ? C9 C10 1.382(4) 2_587 ? C9 F1 1.359(3) . ? C10 C9 1.382(4) 2_587 ? C10 F2 1.356(3) . ? C11 C12 1.393(4) . ? C11 C13 1.386(4) . ? C11 I1 2.112(3) . ? C12 C13 1.386(4) 2_756 ? C12 F3 1.354(3) . ? C13 C12 1.386(4) 2_756 ? C13 F4 1.361(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H1B C1 C2 118.1 . . ? H1B C1 N1 118.1 . . ? C2 C1 N1 123.8(3) . . ? C1 C2 H2A 120.8 . . ? C1 C2 C3 118.4(3) . . ? H2A C2 C3 120.8 . . ? C2 C3 C4 118.4(3) . . ? C2 C3 C6 119.0(3) . . ? C4 C3 C6 122.7(3) . . ? C3 C4 H4A 120.5 . . ? C3 C4 C5 119.0(3) . . ? H4A C4 C5 120.5 . . ? C4 C5 H5A 118.4 . . ? C4 C5 N1 123.1(3) . . ? H5A C5 N1 118.4 . . ? C3 C6 O1 123.1(3) . . ? C3 C6 O2 111.6(3) . . ? O1 C6 O2 125.2(3) . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7A C7 O2 109.5 . . ? H7B C7 H7C 109.5 . . ? H7B C7 O2 109.5 . . ? H7C C7 O2 109.5 . . ? C9 C8 C10 116.6(3) . . ? C9 C8 I2 122.4(2) . . ? C10 C8 I2 121.0(2) . . ? C8 C9 C10 121.6(3) . 2_587 ? C8 C9 F1 119.7(3) . . ? C10 C9 F1 118.7(3) 2_587 . ? C8 C10 C9 121.7(3) . 2_587 ? C8 C10 F2 119.7(3) . . ? C9 C10 F2 118.5(3) 2_587 . ? C12 C11 C13 117.3(3) . . ? C12 C11 I1 120.5(2) . . ? C13 C11 I1 122.1(2) . . ? C11 C12 C13 121.0(3) . 2_756 ? C11 C12 F3 120.5(3) . . ? C13 C12 F3 118.5(3) 2_756 . ? C11 C13 C12 121.7(3) . 2_756 ? C11 C13 F4 119.8(3) . . ? C12 C13 F4 118.5(3) 2_756 . ? C1 N1 C5 117.3(3) . . ? C6 O2 C7 116.8(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 0.8(5) . . . . ? C1 C2 C3 C4 -0.1(5) . . . . ? C1 C2 C3 C6 179.2(3) . . . . ? C2 C3 C4 C5 -0.6(5) . . . . ? C6 C3 C4 C5 -179.9(3) . . . . ? C3 C4 C5 N1 0.8(5) . . . . ? C2 C3 C6 O1 18.6(5) . . . . ? C2 C3 C6 O2 -160.2(3) . . . . ? C4 C3 C6 O1 -162.1(3) . . . . ? C4 C3 C6 O2 19.0(4) . . . . ? C10 C8 C9 C10 -2.1(5) . . . 2_587 ? C10 C8 C9 F1 177.5(3) . . . . ? I2 C8 C9 C10 176.2(2) . . . 2_587 ? I2 C8 C9 F1 -4.3(4) . . . . ? C9 C8 C10 C9 2.1(5) . . . 2_587 ? C9 C8 C10 F2 -178.9(3) . . . . ? I2 C8 C10 C9 -176.2(2) . . . 2_587 ? I2 C8 C10 F2 2.8(4) . . . . ? C13 C11 C12 C13 -0.9(5) . . . 2_756 ? C13 C11 C12 F3 179.2(3) . . . . ? I1 C11 C12 C13 176.6(2) . . . 2_756 ? I1 C11 C12 F3 -3.2(4) . . . . ? C12 C11 C13 C12 1.0(5) . . . 2_756 ? C12 C11 C13 F4 -178.6(3) . . . . ? I1 C11 C13 C12 -176.6(2) . . . 2_756 ? I1 C11 C13 F4 3.9(4) . . . . ? C4 C5 N1 C1 -0.1(5) . . . . ? C2 C1 N1 C5 -0.7(5) . . . . ? C3 C6 O2 C7 179.6(3) . . . . ? O1 C6 O2 C7 0.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.59 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.458 _refine_diff_density_min -0.603 _refine_diff_density_rms 0.110 # Attachment '3b_CIF.cif' data_lrs031 _database_code_depnum_ccdc_archive 'CCDC 630672' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2 C7 H7 O2 N,C6 F4 I2' _chemical_formula_sum 'C20 H14 F4 I2 N2 O4' _chemical_formula_weight 676.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.1581(4) _cell_length_b 10.7974(8) _cell_length_c 12.7958(19) _cell_angle_alpha 91.102(11) _cell_angle_beta 97.913(12) _cell_angle_gamma 90.912(8) _cell_volume 568.81(11) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2343 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.974 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 322 _exptl_absorpt_coefficient_mu 2.826 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2819 _exptl_absorpt_correction_T_max 0.6765 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6429 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 5.15 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1924 _reflns_number_gt 1785 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement EvalCCD _computing_data_reduction EvalCCD _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 1.3, Diamond 3' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.3199P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1924 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0220 _refine_ls_R_factor_gt 0.0163 _refine_ls_wR_factor_ref 0.0404 _refine_ls_wR_factor_gt 0.0365 _refine_ls_goodness_of_fit_ref 1.179 _refine_ls_restrained_S_all 1.179 _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 0.74502(4) 0.417214(16) 0.241908(12) 0.02916(8) Uani 1 1 d . . . F1 F 0.9982(5) 0.25628(14) 0.05427(13) 0.0481(5) Uani 1 1 d . . . F2 F 0.7971(5) 0.68019(15) 0.12705(12) 0.0476(5) Uani 1 1 d . . . C8 C 0.8907(6) 0.4660(2) 0.09631(18) 0.0250(6) Uani 1 1 d . . . O1 O 0.5759(5) 0.11900(18) 0.78213(14) 0.0410(5) Uani 1 1 d . . . N1 N 0.5707(6) 0.3299(2) 0.43841(17) 0.0334(5) Uani 1 1 d . . . O2 O 0.1981(6) 0.00451(19) 0.67729(16) 0.0508(6) Uani 1 1 d . . . C4 C 0.3878(7) 0.2254(2) 0.4211(2) 0.0328(6) Uani 1 1 d . . . H4A H 0.2967 0.2044 0.3506 0.039 Uiso 1 1 calc R . . C1 C 0.4607(6) 0.1760(2) 0.6043(2) 0.0267(6) Uani 1 1 d . . . C10 C 0.8986(6) 0.5897(2) 0.06535(19) 0.0277(6) Uani 1 1 d . . . C5 C 0.3255(7) 0.1467(2) 0.5009(2) 0.0333(6) Uani 1 1 d . . . H5A H 0.1934 0.0744 0.4852 0.040 Uiso 1 1 calc R . . C2 C 0.6511(7) 0.2839(2) 0.6236(2) 0.0326(6) Uani 1 1 d . . . H2A H 0.7475 0.3065 0.6932 0.039 Uiso 1 1 calc R . . C9 C 0.9953(6) 0.3786(2) 0.0286(2) 0.0279(6) Uani 1 1 d . . . C6 C 0.3933(7) 0.0896(2) 0.6900(2) 0.0318(6) Uani 1 1 d . . . C3 C 0.6963(7) 0.3577(3) 0.5382(2) 0.0360(7) Uani 1 1 d . . . H3A H 0.8231 0.4317 0.5516 0.043 Uiso 1 1 calc R . . C7 C 0.5243(9) 0.0398(3) 0.8697(2) 0.0551(9) Uani 1 1 d . . . H7A H 0.6672 0.0677 0.9335 0.083 Uiso 1 1 calc R . . H7B H 0.5737 -0.0460 0.8524 0.083 Uiso 1 1 calc R . . H7C H 0.2975 0.0445 0.8822 0.083 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 0.02153(11) 0.04758(13) 0.01842(10) 0.00734(7) 0.00222(7) -0.00101(8) F1 0.0784(14) 0.0336(9) 0.0340(9) 0.0082(7) 0.0130(9) 0.0023(9) F2 0.0745(13) 0.0422(9) 0.0296(9) -0.0002(7) 0.0180(9) 0.0143(9) C8 0.0187(13) 0.0416(15) 0.0139(12) 0.0052(11) -0.0010(10) -0.0015(11) O1 0.0513(13) 0.0491(12) 0.0241(10) 0.0112(9) 0.0094(10) -0.0006(10) N1 0.0352(14) 0.0390(13) 0.0277(13) 0.0095(10) 0.0087(11) 0.0031(11) O2 0.0712(17) 0.0420(12) 0.0393(12) 0.0108(9) 0.0088(11) -0.0161(12) C4 0.0384(17) 0.0378(16) 0.0224(14) 0.0025(11) 0.0035(12) 0.0068(13) C1 0.0306(15) 0.0270(13) 0.0245(13) 0.0032(10) 0.0100(12) 0.0066(11) C10 0.0258(15) 0.0362(15) 0.0207(13) -0.0032(11) 0.0014(11) 0.0036(12) C5 0.0397(17) 0.0328(15) 0.0282(15) 0.0017(11) 0.0081(13) -0.0013(13) C2 0.0332(16) 0.0412(16) 0.0234(14) 0.0023(12) 0.0036(12) 0.0020(13) C9 0.0298(15) 0.0298(14) 0.0230(13) 0.0064(11) -0.0013(12) -0.0012(12) C6 0.0389(17) 0.0324(15) 0.0263(15) 0.0044(11) 0.0114(13) 0.0093(13) C3 0.0392(17) 0.0374(16) 0.0315(16) 0.0061(12) 0.0049(13) -0.0060(13) C7 0.074(3) 0.065(2) 0.0286(17) 0.0250(15) 0.0112(17) -0.0003(19) _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 C8 2.111(2) . ? F1 C9 1.368(3) . ? F2 C10 1.354(3) . ? C8 C10 1.401(4) . ? C8 C9 1.384(4) . ? O1 C6 1.342(3) . ? O1 C7 1.460(3) . ? N1 C4 1.349(4) . ? N1 C3 1.337(4) . ? O2 C6 1.210(4) . ? C4 H4A 0.9500 . ? C4 C5 1.389(4) . ? C1 C5 1.393(4) . ? C1 C2 1.396(4) . ? C1 C6 1.506(3) . ? C10 C9 1.383(4) 2_765 ? C5 H5A 0.9500 . ? C2 H2A 0.9500 . ? C2 C3 1.397(4) . ? C9 C10 1.383(4) 2_765 ? C3 H3A 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 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 I1 C8 C10 121.42(18) . . ? I1 C8 C9 121.94(18) . . ? C10 C8 C9 116.6(2) . . ? C6 O1 C7 115.0(2) . . ? C4 N1 C3 117.3(2) . . ? N1 C4 H4A 118.3 . . ? N1 C4 C5 123.4(3) . . ? H4A C4 C5 118.3 . . ? C5 C1 C2 118.6(2) . . ? C5 C1 C6 118.2(2) . . ? C2 C1 C6 123.2(2) . . ? F2 C10 C8 120.0(2) . . ? F2 C10 C9 118.9(2) . 2_765 ? C8 C10 C9 121.1(2) . 2_765 ? C4 C5 C1 118.7(3) . . ? C4 C5 H5A 120.7 . . ? C1 C5 H5A 120.7 . . ? C1 C2 H2A 120.8 . . ? C1 C2 C3 118.3(3) . . ? H2A C2 C3 120.8 . . ? F1 C9 C8 119.8(2) . . ? F1 C9 C10 117.8(2) . 2_765 ? C8 C9 C10 122.3(2) . 2_765 ? O1 C6 O2 124.3(2) . . ? O1 C6 C1 111.6(2) . . ? O2 C6 C1 124.2(3) . . ? N1 C3 C2 123.6(3) . . ? N1 C3 H3A 118.2 . . ? C2 C3 H3A 118.2 . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 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 C3 N1 C4 C5 -0.1(4) . . . . ? I1 C8 C10 F2 -3.1(3) . . . . ? I1 C8 C10 C9 177.8(2) . . . 2_765 ? C9 C8 C10 F2 179.4(2) . . . . ? C9 C8 C10 C9 0.3(4) . . . 2_765 ? N1 C4 C5 C1 -0.6(4) . . . . ? C2 C1 C5 C4 0.5(4) . . . . ? C6 C1 C5 C4 -179.6(2) . . . . ? C5 C1 C2 C3 0.2(4) . . . . ? C6 C1 C2 C3 -179.7(2) . . . . ? I1 C8 C9 F1 1.7(3) . . . . ? I1 C8 C9 C10 -177.8(2) . . . 2_765 ? C10 C8 C9 F1 179.2(2) . . . . ? C10 C8 C9 C10 -0.3(4) . . . 2_765 ? C7 O1 C6 O2 0.0(4) . . . . ? C7 O1 C6 C1 179.8(2) . . . . ? C5 C1 C6 O1 170.8(2) . . . . ? C5 C1 C6 O2 -9.4(4) . . . . ? C2 C1 C6 O1 -9.4(4) . . . . ? C2 C1 C6 O2 170.4(3) . . . . ? C4 N1 C3 C2 0.9(4) . . . . ? C1 C2 C3 N1 -1.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.448 _refine_diff_density_min -0.461 _refine_diff_density_rms 0.119