# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'ProfD Pierangelo Metrangolo' _publ_contact_author_email PIERANGELO.METRANGOLO@POLIMI.IT _publ_section_title ; Site selective supramolecular synthesis of halogen bonded cocrystals incorporating the photoactive azo group ; loop_ _publ_author_name 'Pierangelo Metrangolo' 'David Fox' 'Dario Pasini' 'Tullio Pilati' 'Giuseppe Resnati' 'Giancarlo Terraneo' # Attachment '3a_revised.cif' data_re110_3a _database_code_depnum_ccdc_archive 'CCDC 685634' _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-4,4'-azobipyridine. 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,8-diiodooctane ; _chemical_name_common ;trans-4,4'-azobipyridine. 1,1,2,2,3,3,4,4,5,5,6,6- dodecafluoro-1,8-diiodooctane ; _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 N4, C6 F12 I2' _chemical_formula_sum 'C16 H8 F12 I2 N4' _chemical_formula_weight 738.06 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' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2392(5) _cell_length_b 8.8344(9) _cell_length_c 11.5520(13) _cell_angle_alpha 94.526(8) _cell_angle_beta 95.701(7) _cell_angle_gamma 91.302(8) _cell_volume 530.13(10) _cell_formula_units_Z 1 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 9860 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 29.88 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 346 _exptl_absorpt_coefficient_mu 3.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS,(Bruker, 1997)' _exptl_absorpt_correction_T_min 0.406236 _exptl_absorpt_correction_T_max 0.548812 _exptl_special_details ; Crystal of this material were too large, but by cutting always we obtained very bad champions. The crystal used for data collection was then reduced at reasonable dimensions by partial melting in chloroform. The crystal temperature was controlled by the Bruker KRIOFLEX low temperature device. ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 12026 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 29.99 _reflns_number_total 3089 _reflns_number_gt 2970 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-III (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) and Mercury 1.4.2, CCDC ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0541P)^2^+0.3679P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3089 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0813 _refine_ls_wR_factor_gt 0.0807 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.121 _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 0.41055(3) 0.502189(16) 0.241119(13) 0.02030(7) Uani 1 1 d . . . F1 F 0.7450(4) 0.3917(2) 0.06798(18) 0.0337(4) Uani 1 1 d . . . F2 F 0.7999(4) 0.2755(2) 0.22715(18) 0.0351(5) Uani 1 1 d . . . F3 F 0.3399(4) 0.1315(2) 0.17921(16) 0.0273(4) Uani 1 1 d . . . F4 F 0.2590(4) 0.2517(2) 0.02275(16) 0.0284(4) Uani 1 1 d . . . F5 F 0.6534(4) 0.1359(2) -0.07387(16) 0.0303(4) Uani 1 1 d . . . F6 F 0.7945(3) 0.0320(2) 0.08406(16) 0.0275(4) Uani 1 1 d . . . N1 N -0.4467(5) 0.9493(3) 0.5270(2) 0.0203(4) Uani 1 1 d . . . N2 N 0.1191(5) 0.7121(3) 0.3602(2) 0.0245(5) Uani 1 1 d . . . C1 C -0.2590(5) 0.8717(3) 0.4645(2) 0.0184(5) Uani 1 1 d . . . C2 C -0.2164(6) 0.8913(3) 0.3500(2) 0.0237(5) Uani 1 1 d . . . C3 C -0.0267(6) 0.8087(3) 0.3017(3) 0.0261(6) Uani 1 1 d . . . C4 C 0.0752(6) 0.6941(3) 0.4699(3) 0.0252(5) Uani 1 1 d . . . C5 C -0.1119(6) 0.7704(3) 0.5257(2) 0.0230(5) Uani 1 1 d . . . C6 C 0.6199(5) 0.3315(3) 0.1506(2) 0.0210(5) Uani 1 1 d . . . C7 C 0.4467(5) 0.1970(3) 0.0937(2) 0.0173(4) Uani 1 1 d . . . C8 C 0.5825(5) 0.0730(3) 0.0205(2) 0.0170(4) Uani 1 1 d . . . H2 H -0.313(8) 0.962(4) 0.307(3) 0.025(9) Uiso 1 1 d . . . H3 H 0.013(8) 0.826(5) 0.223(4) 0.029(10) Uiso 1 1 d . . . H4 H 0.188(8) 0.636(5) 0.510(3) 0.030(10) Uiso 1 1 d . . . H5 H -0.135(8) 0.760(5) 0.604(4) 0.030(10) Uiso 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 0.02134(11) 0.01583(10) 0.02306(11) -0.00463(6) 0.00377(7) 0.00107(6) F1 0.0353(10) 0.0272(9) 0.0403(10) -0.0068(8) 0.0217(8) -0.0077(8) F2 0.0278(9) 0.0355(10) 0.0366(10) -0.0126(8) -0.0142(8) 0.0125(8) F3 0.0318(9) 0.0225(8) 0.0296(9) -0.0034(7) 0.0184(7) -0.0008(7) F4 0.0240(9) 0.0260(8) 0.0317(9) -0.0069(7) -0.0092(7) 0.0115(7) F5 0.0473(11) 0.0203(8) 0.0257(8) -0.0012(6) 0.0193(8) -0.0049(7) F6 0.0171(8) 0.0270(8) 0.0355(9) -0.0096(7) -0.0041(7) 0.0077(6) N1 0.0227(11) 0.0188(10) 0.0198(10) -0.0014(8) 0.0059(8) 0.0040(8) N2 0.0242(12) 0.0204(10) 0.0284(12) -0.0039(9) 0.0054(9) 0.0023(9) C1 0.0193(12) 0.0153(10) 0.0205(11) -0.0035(8) 0.0045(9) 0.0003(9) C2 0.0279(14) 0.0240(13) 0.0200(12) 0.0014(10) 0.0057(10) 0.0071(11) C3 0.0297(15) 0.0263(13) 0.0229(12) -0.0030(10) 0.0082(11) 0.0044(11) C4 0.0236(13) 0.0198(12) 0.0322(14) -0.0001(10) 0.0031(11) 0.0062(10) C5 0.0247(13) 0.0223(12) 0.0224(12) 0.0014(10) 0.0044(10) 0.0033(10) C6 0.0176(12) 0.0202(12) 0.0240(12) -0.0040(9) 0.0014(9) 0.0014(9) C7 0.0155(11) 0.0178(10) 0.0183(10) -0.0016(8) 0.0019(8) 0.0032(8) C8 0.0163(11) 0.0175(11) 0.0176(10) -0.0014(8) 0.0047(8) 0.0030(9) _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 C6 2.151(3) . ? F1 C6 1.345(3) . ? F2 C6 1.357(3) . ? F3 C7 1.345(3) . ? F4 C7 1.340(3) . ? F5 C8 1.342(3) . ? F6 C8 1.343(3) . ? N1 N1 1.243(5) 2_476 ? N1 C1 1.432(3) . ? N2 C4 1.331(4) . ? N2 C3 1.336(4) . ? C1 C5 1.385(4) . ? C1 C2 1.387(4) . ? C2 C3 1.382(4) . ? C2 H2 0.95(4) . ? C3 H3 0.98(4) . ? C4 C5 1.385(4) . ? C4 H4 0.91(4) . ? C5 H5 0.94(4) . ? C6 C7 1.541(4) . ? C7 C8 1.559(3) . ? C8 C8 1.551(5) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 N1 C1 113.3(3) 2_476 . ? C4 N2 C3 117.7(2) . . ? C5 C1 C2 119.1(2) . . ? C5 C1 N1 115.9(2) . . ? C2 C1 N1 125.0(2) . . ? C3 C2 C1 118.3(3) . . ? C3 C2 H2 121(2) . . ? C1 C2 H2 121(2) . . ? N2 C3 C2 123.3(3) . . ? N2 C3 H3 117(2) . . ? C2 C3 H3 119(2) . . ? N2 C4 C5 123.4(3) . . ? N2 C4 H4 116(3) . . ? C5 C4 H4 120(3) . . ? C4 C5 C1 118.2(3) . . ? C4 C5 H5 122(3) . . ? C1 C5 H5 119(3) . . ? F1 C6 F2 107.1(2) . . ? F1 C6 C7 109.0(2) . . ? F2 C6 C7 107.7(2) . . ? F1 C6 I1 110.78(18) . . ? F2 C6 I1 109.33(18) . . ? C7 C6 I1 112.75(17) . . ? F4 C7 F3 108.4(2) . . ? F4 C7 C6 108.4(2) . . ? F3 C7 C6 107.8(2) . . ? F4 C7 C8 107.6(2) . . ? F3 C7 C8 108.8(2) . . ? C6 C7 C8 115.7(2) . . ? F5 C8 F6 108.5(2) . . ? F5 C8 C8 108.7(3) . 2_655 ? F6 C8 C8 107.8(3) . 2_655 ? F5 C8 C7 107.5(2) . . ? F6 C8 C7 108.9(2) . . ? C8 C8 C7 115.3(3) 2_655 . ? 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 N1 C1 C5 172.4(3) 2_476 . . . ? N1 N1 C1 C2 -7.5(5) 2_476 . . . ? C5 C1 C2 C3 -0.3(4) . . . . ? N1 C1 C2 C3 179.6(3) . . . . ? C4 N2 C3 C2 0.9(5) . . . . ? C1 C2 C3 N2 -0.6(5) . . . . ? C3 N2 C4 C5 -0.2(5) . . . . ? N2 C4 C5 C1 -0.7(5) . . . . ? C2 C1 C5 C4 0.9(4) . . . . ? N1 C1 C5 C4 -179.0(3) . . . . ? F1 C6 C7 F4 -67.6(3) . . . . ? F2 C6 C7 F4 176.5(2) . . . . ? I1 C6 C7 F4 55.8(2) . . . . ? F1 C6 C7 F3 175.2(2) . . . . ? F2 C6 C7 F3 59.3(3) . . . . ? I1 C6 C7 F3 -61.4(2) . . . . ? F1 C6 C7 C8 53.2(3) . . . . ? F2 C6 C7 C8 -62.6(3) . . . . ? I1 C6 C7 C8 176.67(16) . . . . ? F4 C7 C8 F5 53.7(3) . . . . ? F3 C7 C8 F5 170.9(2) . . . . ? C6 C7 C8 F5 -67.6(3) . . . . ? F4 C7 C8 F6 171.0(2) . . . . ? F3 C7 C8 F6 -71.7(3) . . . . ? C6 C7 C8 F6 49.7(3) . . . . ? F4 C7 C8 C8 -67.7(3) . . . 2_655 ? F3 C7 C8 C8 49.6(3) . . . 2_655 ? C6 C7 C8 C8 171.0(3) . . . 2_655 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.759 _refine_diff_density_min -2.784 _refine_diff_density_rms 0.183 # Attachment '3b_revised.cif' data_re101_3b _database_code_depnum_ccdc_archive 'CCDC 685635' _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-4,4'-azobipyridine 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-hexadecafluoro-1,8-diiodooctane ; _chemical_name_common ; trans-4,4'-azobipyridine 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8- hexadecafluoro-1,8-diiodooctane ; _chemical_melting_point ? _chemical_formula_moiety 'C8 F16 I2, C10 H8 N4' _chemical_formula_sum 'C18 H8 F16 I2 N4' _chemical_formula_weight 838.08 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' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2482(7) _cell_length_b 8.6925(14) _cell_length_c 13.289(2) _cell_angle_alpha 84.316(7) _cell_angle_beta 86.245(7) _cell_angle_gamma 88.241(8) _cell_volume 601.79(16) _cell_formula_units_Z 1 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 6523 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 29.43 _exptl_crystal_description needle _exptl_crystal_colour 'pale red' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 394 _exptl_absorpt_coefficient_mu 2.754 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS,(Bruker, 1997)' _exptl_absorpt_correction_T_min 0.67612 _exptl_absorpt_correction_T_max 0.818731 _exptl_special_details ; The crystal temperature was controlled by the Bruker KRIOFLEX low temperature device. ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 12848 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3491 _reflns_number_gt 3219 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-III (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) and Mercury 1.4.2, CCDC ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0398P)^2^+0.2274P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3491 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0642 _refine_ls_wR_factor_gt 0.0628 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.000 _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 I I 0.07045(3) 0.559270(16) 0.274102(11) 0.02192(6) Uani 1 1 d . . . F1 F -0.2842(3) 0.48764(19) 0.12690(13) 0.0356(4) Uani 1 1 d . . . F2 F -0.3059(3) 0.3253(2) 0.26248(13) 0.0361(4) Uani 1 1 d . . . F3 F 0.2046(3) 0.36934(18) 0.07989(12) 0.0314(3) Uani 1 1 d . . . F4 F 0.1549(3) 0.20173(17) 0.21245(12) 0.0292(3) Uani 1 1 d . . . F5 F -0.2040(3) 0.26828(18) -0.00121(12) 0.0326(3) Uani 1 1 d . . . F6 F -0.3007(3) 0.11529(19) 0.13436(12) 0.0332(4) Uani 1 1 d . . . F7 F 0.2699(3) 0.1137(2) -0.01560(16) 0.0473(5) Uani 1 1 d . . . F8 F 0.1432(5) -0.0420(2) 0.11444(14) 0.0516(6) Uani 1 1 d . . . N1 N 0.9487(4) 0.9423(2) 0.52342(15) 0.0217(4) Uani 1 1 d . . . C1 C 0.7556(4) 0.8799(3) 0.46840(17) 0.0205(4) Uani 1 1 d . . . C2 C 0.6114(5) 0.7646(3) 0.52176(18) 0.0236(4) Uani 1 1 d . . . C3 C 0.4198(5) 0.7014(3) 0.4735(2) 0.0266(5) Uani 1 1 d . . . N2 N 0.3699(4) 0.7452(2) 0.37761(17) 0.0256(4) Uani 1 1 d . . . C4 C 0.5135(5) 0.8558(3) 0.32688(19) 0.0276(5) Uani 1 1 d . . . C5 C 0.7075(5) 0.9264(3) 0.36891(19) 0.0254(5) Uani 1 1 d . . . C6 C -0.1432(4) 0.4058(3) 0.19511(17) 0.0220(4) Uani 1 1 d . . . C7 C 0.0315(4) 0.2899(3) 0.14080(16) 0.0192(4) Uani 1 1 d . . . C8 C -0.1065(4) 0.1821(3) 0.07647(16) 0.0190(4) Uani 1 1 d . . . C9 C 0.0653(4) 0.0514(3) 0.03500(18) 0.0220(4) Uani 1 1 d . . . H2 H 0.637(6) 0.728(4) 0.591(3) 0.034(8) Uiso 1 1 d . . . H3 H 0.321(7) 0.627(4) 0.508(3) 0.033(8) Uiso 1 1 d . . . H4 H 0.474(7) 0.883(4) 0.259(3) 0.037(9) Uiso 1 1 d . . . H5 H 0.789(6) 0.997(3) 0.331(2) 0.021(7) Uiso 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 I 0.02315(8) 0.01957(8) 0.02442(9) -0.00768(5) -0.00324(5) -0.00142(5) F1 0.0344(8) 0.0347(8) 0.0412(9) -0.0143(7) -0.0185(7) 0.0111(7) F2 0.0335(8) 0.0392(9) 0.0367(9) -0.0166(7) 0.0156(7) -0.0167(7) F3 0.0299(8) 0.0312(8) 0.0342(8) -0.0130(6) 0.0115(6) -0.0157(6) F4 0.0334(8) 0.0261(7) 0.0309(7) -0.0086(6) -0.0176(6) 0.0042(6) F5 0.0444(9) 0.0277(7) 0.0281(7) -0.0072(6) -0.0184(7) 0.0095(7) F6 0.0274(7) 0.0390(9) 0.0352(8) -0.0161(7) 0.0091(6) -0.0179(6) F7 0.0265(8) 0.0483(10) 0.0721(13) -0.0383(10) 0.0179(8) -0.0182(7) F8 0.0872(15) 0.0335(9) 0.0400(10) -0.0155(8) -0.0412(10) 0.0233(10) N1 0.0239(9) 0.0204(9) 0.0217(9) -0.0040(7) -0.0044(7) -0.0008(7) C1 0.0215(10) 0.0189(10) 0.0220(10) -0.0063(8) -0.0035(8) 0.0022(8) C2 0.0248(11) 0.0226(11) 0.0233(11) -0.0006(8) -0.0036(8) -0.0004(8) C3 0.0256(11) 0.0202(11) 0.0343(13) -0.0028(9) -0.0015(9) -0.0039(9) N2 0.0239(9) 0.0244(10) 0.0308(10) -0.0105(8) -0.0058(8) -0.0024(8) C4 0.0323(13) 0.0276(12) 0.0244(11) -0.0052(9) -0.0086(9) -0.0033(10) C5 0.0314(12) 0.0218(11) 0.0233(11) -0.0016(9) -0.0034(9) -0.0065(9) C6 0.0193(10) 0.0267(11) 0.0209(10) -0.0061(8) -0.0017(8) -0.0021(8) C7 0.0178(9) 0.0206(10) 0.0197(9) -0.0041(8) -0.0009(7) -0.0044(8) C8 0.0187(9) 0.0209(10) 0.0182(9) -0.0038(8) -0.0030(7) -0.0040(8) C9 0.0202(10) 0.0229(10) 0.0249(11) -0.0071(8) -0.0073(8) -0.0023(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 I C6 2.159(2) . ? F1 C6 1.343(3) . ? F2 C6 1.354(3) . ? F3 C7 1.337(2) . ? F4 C7 1.349(3) . ? F5 C8 1.335(3) . ? F6 C8 1.346(3) . ? F7 C9 1.329(3) . ? F8 C9 1.344(3) . ? N1 N1 1.245(4) 2_776 ? N1 C1 1.437(3) . ? C1 C5 1.381(3) . ? C1 C2 1.384(3) . ? C2 C3 1.383(3) . ? C2 H2 0.97(3) . ? C3 N2 1.333(3) . ? C3 H3 0.91(3) . ? N2 C4 1.340(3) . ? C4 C5 1.380(3) . ? C4 H4 0.95(4) . ? C5 H5 0.86(3) . ? C6 C7 1.542(3) . ? C7 C8 1.554(3) . ? C8 C9 1.550(3) . ? C9 C9 1.555(4) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 N1 C1 113.0(2) 2_776 . ? C5 C1 C2 119.4(2) . . ? C5 C1 N1 125.0(2) . . ? C2 C1 N1 115.6(2) . . ? C3 C2 C1 118.4(2) . . ? C3 C2 H2 119(2) . . ? C1 C2 H2 123(2) . . ? N2 C3 C2 123.0(2) . . ? N2 C3 H3 117(2) . . ? C2 C3 H3 120(2) . . ? C3 N2 C4 117.7(2) . . ? N2 C4 C5 123.4(2) . . ? N2 C4 H4 115(2) . . ? C5 C4 H4 121(2) . . ? C4 C5 C1 118.0(2) . . ? C4 C5 H5 117(2) . . ? C1 C5 H5 125(2) . . ? F1 C6 F2 107.51(19) . . ? F1 C6 C7 109.12(18) . . ? F2 C6 C7 108.54(19) . . ? F1 C6 I 110.20(16) . . ? F2 C6 I 109.11(15) . . ? C7 C6 I 112.23(14) . . ? F3 C7 F4 108.44(18) . . ? F3 C7 C6 108.48(18) . . ? F4 C7 C6 107.45(18) . . ? F3 C7 C8 108.23(17) . . ? F4 C7 C8 108.65(18) . . ? C6 C7 C8 115.40(18) . . ? F5 C8 F6 108.24(19) . . ? F5 C8 C9 108.97(18) . . ? F6 C8 C9 107.75(18) . . ? F5 C8 C7 108.51(18) . . ? F6 C8 C7 108.54(17) . . ? C9 C8 C7 114.67(18) . . ? F7 C9 F8 108.4(2) . . ? F7 C9 C8 108.91(19) . . ? F8 C9 C8 108.04(19) . . ? F7 C9 C9 108.6(2) . 2 ? F8 C9 C9 107.3(2) . 2 ? C8 C9 C9 115.3(2) . 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 N1 C1 C5 8.4(4) 2_776 . . . ? N1 N1 C1 C2 -171.8(2) 2_776 . . . ? C5 C1 C2 C3 -1.1(4) . . . . ? N1 C1 C2 C3 179.1(2) . . . . ? C1 C2 C3 N2 0.8(4) . . . . ? C2 C3 N2 C4 -0.1(4) . . . . ? C3 N2 C4 C5 -0.4(4) . . . . ? N2 C4 C5 C1 0.1(4) . . . . ? C2 C1 C5 C4 0.7(4) . . . . ? N1 C1 C5 C4 -179.5(2) . . . . ? F1 C6 C7 F3 67.8(2) . . . . ? F2 C6 C7 F3 -175.37(18) . . . . ? I C6 C7 F3 -54.7(2) . . . . ? F1 C6 C7 F4 -175.20(18) . . . . ? F2 C6 C7 F4 -58.3(2) . . . . ? I C6 C7 F4 62.35(19) . . . . ? F1 C6 C7 C8 -53.8(3) . . . . ? F2 C6 C7 C8 63.0(2) . . . . ? I C6 C7 C8 -176.29(14) . . . . ? F3 C7 C8 F5 -55.5(2) . . . . ? F4 C7 C8 F5 -173.07(18) . . . . ? C6 C7 C8 F5 66.2(2) . . . . ? F3 C7 C8 F6 -172.92(18) . . . . ? F4 C7 C8 F6 69.5(2) . . . . ? C6 C7 C8 F6 -51.2(2) . . . . ? F3 C7 C8 C9 66.6(2) . . . . ? F4 C7 C8 C9 -51.0(2) . . . . ? C6 C7 C8 C9 -171.70(19) . . . . ? F5 C8 C9 F7 67.9(2) . . . . ? F6 C8 C9 F7 -174.93(19) . . . . ? C7 C8 C9 F7 -54.0(3) . . . . ? F5 C8 C9 F8 -174.60(19) . . . . ? F6 C8 C9 F8 -57.4(2) . . . . ? C7 C8 C9 F8 63.6(2) . . . . ? F5 C8 C9 C9 -54.6(3) . . . 2 ? F6 C8 C9 C9 62.7(3) . . . 2 ? C7 C8 C9 C9 -176.4(2) . . . 2 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.203 _refine_diff_density_min -0.923 _refine_diff_density_rms 0.115