Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Prof. Dr. Edwin Weber' _publ_contact_author_address ; Institut fur Organische Chemie TU Bergakademie Freiberg Leipziger Strasse 29 D-09596 Freiberg/Sachsen Germany ; _publ_contact_author_email edwin.weber@chemie.tu-freiberg.de _publ_contact_author_fax '49(03731) 392386' _publ_contact_author_phone '49(03731) 393170' _publ_section_title ; Crystalline packings of diketoarylhydrazones controlled by a methyl for trifluoromethyl structural change ; loop_ _publ_author_name _publ_author_address J.Marten ; Institut fur Organische Chemie TU Bergakademie Freiberg Leipziger Strasse 29 D-09596 Freiberg/Sachsen Germany ; W.Seichter ; Institut fur Organische Chemie TU Bergakademie Freiberg Leipziger Strasse 29 D-09596 Freiberg/Sachsen Germany ; E.Weber ; Institut fur Organische Chemie TU Bergakademie Freiberg Leipziger Strasse 29 D-09596 Freiberg/Sachsen Germany ; U.Bohme ; Institut fur Organische Chemie TU Bergakademie Freiberg Leipziger Strasse 29 D-09596 Freiberg/Sachsen Germany ; # TEXT _publ_section_abstract ; Three new hydrazone compounds having a p-iodoaryl and diketohydrazone molecular skeleton in common but feature a gradual replacement of the two methyl for trifluoromethyl terminal groups were prepared and comparatively studied with regard to their crystal structures. A quantum chemical calculation of the single trifluoromethyl modified compound was undertaken to decide on to low energy conformation referring to the hydrogen bonded ring site. While the molecular structures of the compounds remain rather unimpaired by the fluorine substitution, their crystalline packings are markedly affected, showing a distinct supramolecular control in the crystal lattices. ; data_jama_8_0m _database_code_depnum_ccdc_archive 'CCDC 661391' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H8 F3 I N2 O2' _chemical_formula_weight 384.09 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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 19.8553(5) _cell_length_b 7.8980(2) _cell_length_c 17.0579(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.9040(10) _cell_angle_gamma 90.00 _cell_volume 2660.78(11) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour red _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.918 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 2.441 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.3317 _exptl_absorpt_correction_T_max 0.4494 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 31049 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 37.71 _reflns_number_total 7084 _reflns_number_gt 3615 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART APEX2 (Bruker-AXS)' _computing_cell_refinement 'SAINT-NT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+4.0122P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7084 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.918 _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 1.098526(10) 0.91297(3) 1.190525(11) 0.07107(9) Uani 1 1 d . . . F1 F 0.78231(14) 0.4079(3) 0.95769(12) 0.1121(9) Uani 1 1 d . . . F2 F 0.68538(12) 0.4614(5) 0.89633(17) 0.1427(12) Uani 1 1 d . . . F3 F 0.75480(13) 0.6601(4) 0.92806(14) 0.1081(8) Uani 1 1 d . . . O1 O 0.74059(11) 0.3996(3) 0.77365(13) 0.0809(7) Uani 1 1 d . . . O2 O 0.92578(11) 0.6092(3) 0.72719(12) 0.0760(6) Uani 1 1 d . . . N1 N 0.87823(10) 0.5950(2) 0.87670(11) 0.0459(4) Uani 1 1 d . . . N2 N 0.93956(10) 0.6509(3) 0.87855(12) 0.0501(4) Uani 1 1 d . . . H2 H 0.9539(15) 0.656(4) 0.8348(19) 0.060(8) Uiso 1 1 d . . . C1 C 0.75038(16) 0.5030(6) 0.90227(19) 0.0812(9) Uani 1 1 d . . . C2 C 0.77687(12) 0.4783(4) 0.82161(14) 0.0549(5) Uani 1 1 d . . . C3 C 0.84327(11) 0.5463(3) 0.81021(12) 0.0462(4) Uani 1 1 d . . . C4 C 0.86781(13) 0.5577(3) 0.73165(14) 0.0543(5) Uani 1 1 d . . . C5 C 0.82374(16) 0.5152(5) 0.65872(16) 0.0743(8) Uani 1 1 d . . . H5A H 0.8451 0.5542 0.6127 0.111 Uiso 1 1 calc R . . H5B H 0.7798 0.5710 0.6597 0.111 Uiso 1 1 calc R . . H5C H 0.8172 0.3923 0.6556 0.111 Uiso 1 1 calc R . . C6 C 0.97381(11) 0.7069(3) 0.94995(12) 0.0466(4) Uani 1 1 d . . . C7 C 0.94553(14) 0.6928(4) 1.02049(14) 0.0588(6) Uani 1 1 d . . . H7 H 0.9018 0.6448 1.0215 0.071 Uiso 1 1 calc R . . C8 C 0.98106(14) 0.7487(4) 1.08934(14) 0.0625(6) Uani 1 1 d . . . H8 H 0.9621 0.7379 1.1380 0.075 Uiso 1 1 calc R . . C9 C 1.04422(12) 0.8203(3) 1.08748(14) 0.0521(5) Uani 1 1 d . . . C10 C 1.07230(13) 0.8349(4) 1.01726(16) 0.0605(6) Uani 1 1 d . . . H10 H 1.1159 0.8839 1.0163 0.073 Uiso 1 1 calc R . . C11 C 1.03709(13) 0.7784(4) 0.94852(15) 0.0586(6) Uani 1 1 d . . . H11 H 1.0564 0.7886 0.9000 0.070 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 0.07922(14) 0.06381(13) 0.06445(12) -0.00449(8) -0.02019(9) 0.00141(8) F1 0.1204(18) 0.154(2) 0.0626(11) 0.0443(13) 0.0130(11) -0.0107(15) F2 0.0676(12) 0.260(4) 0.1065(17) -0.004(2) 0.0372(12) -0.0362(18) F3 0.1075(16) 0.129(2) 0.0930(15) -0.0218(15) 0.0362(13) 0.0270(15) O1 0.0650(12) 0.1085(19) 0.0660(12) 0.0094(11) -0.0082(9) -0.0237(11) O2 0.0669(12) 0.1135(19) 0.0501(10) -0.0077(10) 0.0186(9) -0.0180(11) N1 0.0512(9) 0.0438(9) 0.0424(8) 0.0032(7) 0.0037(7) 0.0015(7) N2 0.0569(11) 0.0532(10) 0.0410(9) -0.0005(8) 0.0084(8) -0.0033(9) C1 0.0622(17) 0.122(3) 0.0621(17) 0.0089(19) 0.0174(13) -0.0021(18) C2 0.0494(11) 0.0651(15) 0.0494(11) 0.0122(11) 0.0011(9) 0.0011(10) C3 0.0498(11) 0.0482(11) 0.0404(9) 0.0013(8) 0.0040(8) 0.0036(9) C4 0.0618(14) 0.0589(14) 0.0427(10) -0.0036(10) 0.0080(9) 0.0018(11) C5 0.0805(19) 0.098(2) 0.0449(12) -0.0133(14) 0.0073(12) -0.0084(17) C6 0.0533(11) 0.0438(10) 0.0424(9) 0.0006(8) 0.0035(8) 0.0007(9) C7 0.0629(14) 0.0695(16) 0.0443(11) 0.0024(11) 0.0065(10) -0.0195(12) C8 0.0704(15) 0.0746(17) 0.0428(10) 0.0011(11) 0.0077(10) -0.0163(13) C9 0.0586(12) 0.0465(12) 0.0490(11) 0.0006(9) -0.0044(9) 0.0017(9) C10 0.0467(12) 0.0695(16) 0.0655(15) -0.0062(13) 0.0069(10) -0.0062(11) C11 0.0540(13) 0.0716(16) 0.0520(12) -0.0040(11) 0.0137(10) -0.0036(11) _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 C9 2.097(2) . ? F1 C1 1.318(4) . ? F2 C1 1.326(4) . ? F3 C1 1.317(5) . ? O1 C2 1.206(3) . ? O2 C4 1.230(3) . ? N1 N2 1.293(3) . ? N1 C3 1.324(3) . ? N2 C6 1.404(3) . ? C1 C2 1.535(4) . ? C2 C3 1.455(3) . ? C3 C4 1.475(3) . ? C4 C5 1.484(4) . ? C6 C11 1.380(3) . ? C6 C7 1.384(3) . ? C7 C8 1.379(3) . ? C8 C9 1.379(4) . ? C9 C10 1.377(4) . ? C10 C11 1.376(4) . ? 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 N1 C3 121.97(19) . . ? N1 N2 C6 119.99(19) . . ? F3 C1 F1 106.7(3) . . ? F3 C1 F2 106.9(3) . . ? F1 C1 F2 107.8(3) . . ? F3 C1 C2 113.7(3) . . ? F1 C1 C2 112.8(3) . . ? F2 C1 C2 108.7(3) . . ? O1 C2 C3 125.9(2) . . ? O1 C2 C1 116.0(3) . . ? C3 C2 C1 118.2(2) . . ? N1 C3 C2 113.26(19) . . ? N1 C3 C4 124.6(2) . . ? C2 C3 C4 122.2(2) . . ? O2 C4 C3 118.4(2) . . ? O2 C4 C5 119.8(2) . . ? C3 C4 C5 121.8(2) . . ? C11 C6 C7 120.0(2) . . ? C11 C6 N2 118.3(2) . . ? C7 C6 N2 121.7(2) . . ? C8 C7 C6 119.8(2) . . ? C7 C8 C9 119.9(2) . . ? C10 C9 C8 120.3(2) . . ? C10 C9 I1 118.72(18) . . ? C8 C9 I1 120.95(18) . . ? C11 C10 C9 119.9(2) . . ? C10 C11 C6 120.1(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 C3 N1 N2 C6 177.7(2) . . . . ? F3 C1 C2 O1 -132.1(3) . . . . ? F1 C1 C2 O1 106.3(3) . . . . ? F2 C1 C2 O1 -13.2(5) . . . . ? F3 C1 C2 C3 49.7(4) . . . . ? F1 C1 C2 C3 -71.9(4) . . . . ? F2 C1 C2 C3 168.5(3) . . . . ? N2 N1 C3 C2 176.6(2) . . . . ? N2 N1 C3 C4 -3.3(4) . . . . ? O1 C2 C3 N1 -166.3(3) . . . . ? C1 C2 C3 N1 11.8(4) . . . . ? O1 C2 C3 C4 13.6(4) . . . . ? C1 C2 C3 C4 -168.4(3) . . . . ? N1 C3 C4 O2 3.2(4) . . . . ? C2 C3 C4 O2 -176.6(3) . . . . ? N1 C3 C4 C5 -174.4(3) . . . . ? C2 C3 C4 C5 5.7(4) . . . . ? N1 N2 C6 C11 -174.9(2) . . . . ? N1 N2 C6 C7 4.7(4) . . . . ? C11 C6 C7 C8 -0.7(4) . . . . ? N2 C6 C7 C8 179.7(3) . . . . ? C6 C7 C8 C9 0.8(4) . . . . ? C7 C8 C9 C10 -0.6(4) . . . . ? C7 C8 C9 I1 178.2(2) . . . . ? C8 C9 C10 C11 0.2(4) . . . . ? I1 C9 C10 C11 -178.6(2) . . . . ? C9 C10 C11 C6 -0.1(4) . . . . ? C7 C6 C11 C10 0.3(4) . . . . ? N2 C6 C11 C10 180.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 37.71 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.924 _refine_diff_density_min -0.894 _refine_diff_density_rms 0.070 data_jama13new _database_code_depnum_ccdc_archive 'CCDC 661392' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 I N2 O2' _chemical_formula_weight 330.12 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' 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 7.9355(3) _cell_length_b 7.9685(3) _cell_length_c 11.1563(5) _cell_angle_alpha 88.762(2) _cell_angle_beta 81.264(2) _cell_angle_gamma 61.6120(10) _cell_volume 612.39(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.790 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 2.602 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.6320 _exptl_absorpt_correction_T_max 0.8780 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 23617 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _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 1.85 _diffrn_reflns_theta_max 34.84 _reflns_number_total 5306 _reflns_number_gt 3282 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART APEX2 (Bruker-AXS)' _computing_cell_refinement 'SAINT-NT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] 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 5306 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1973 _refine_ls_wR_factor_gt 0.1781 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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 I1 I 0.32193(4) -0.46677(4) 1.30451(2) 0.07499(16) Uani 1 1 d . . . O1 O 0.2666(6) 0.2499(6) 0.5124(3) 0.0876(10) Uani 1 1 d . . . O2 O 0.1451(8) 0.4860(5) 0.8655(3) 0.0950(12) Uani 1 1 d . . . N1 N 0.2345(4) 0.1102(4) 0.8073(2) 0.0499(5) Uani 1 1 d . . . N2 N 0.2257(5) 0.1460(4) 0.9218(2) 0.0549(6) Uani 1 1 d . . . H2 H 0.2028 0.2597 0.9473 0.066 Uiso 1 1 calc R . . C1 C 0.2331(9) -0.0173(8) 0.5807(4) 0.0839(14) Uani 1 1 d . . . H1A H 0.2228 -0.0327 0.4957 0.126 Uiso 1 1 calc R . . H1B H 0.1201 -0.0125 0.6336 0.126 Uiso 1 1 calc R . . H1C H 0.3518 -0.1256 0.6002 0.126 Uiso 1 1 calc R . . C2 C 0.2401(5) 0.1646(5) 0.6002(3) 0.0563(7) Uani 1 1 d . . . C3 C 0.2123(5) 0.2403(5) 0.7271(3) 0.0527(6) Uani 1 1 d . . . C4 C 0.1646(7) 0.4370(6) 0.7581(4) 0.0645(9) Uani 1 1 d . . . C5 C 0.1273(8) 0.5846(7) 0.6646(4) 0.0780(13) Uani 1 1 d . . . H5A H 0.0693 0.7117 0.7056 0.117 Uiso 1 1 calc R . . H5B H 0.0382 0.5806 0.6142 0.117 Uiso 1 1 calc R . . H5C H 0.2501 0.5574 0.6132 0.117 Uiso 1 1 calc R . . C6 C 0.2522(5) 0.0064(5) 1.0037(3) 0.0512(6) Uani 1 1 d . . . C7 C 0.2502(6) -0.1634(5) 0.9732(3) 0.0571(7) Uani 1 1 d . . . H7 H 0.2343 -0.1859 0.8934 0.068 Uiso 1 1 calc R . . C8 C 0.2713(6) -0.2967(5) 1.0583(3) 0.0583(7) Uani 1 1 d . . . H8 H 0.2673 -0.4097 1.0378 0.070 Uiso 1 1 calc R . . C9 C 0.2985(5) -0.2655(5) 1.1752(3) 0.0545(7) Uani 1 1 d . . . C10 C 0.3014(6) -0.0995(6) 1.2064(3) 0.0616(8) Uani 1 1 d . . . H10 H 0.3188 -0.0787 1.2861 0.074 Uiso 1 1 calc R . . C11 C 0.2787(6) 0.0365(6) 1.1210(3) 0.0624(8) Uani 1 1 d . . . H11 H 0.2813 0.1500 1.1424 0.075 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 0.0704(2) 0.0872(3) 0.0620(2) 0.03980(15) -0.01725(13) -0.03298(17) O1 0.111(3) 0.101(2) 0.0490(14) 0.0321(15) -0.0122(15) -0.051(2) O2 0.165(4) 0.082(2) 0.0620(18) 0.0203(15) -0.036(2) -0.074(3) N1 0.0534(14) 0.0593(14) 0.0390(11) 0.0179(10) -0.0112(9) -0.0281(12) N2 0.0688(17) 0.0600(15) 0.0415(11) 0.0159(10) -0.0147(11) -0.0340(14) C1 0.121(4) 0.092(3) 0.051(2) 0.012(2) -0.013(2) -0.061(3) C2 0.0640(18) 0.0636(18) 0.0401(13) 0.0165(12) -0.0107(12) -0.0294(16) C3 0.0556(16) 0.0633(18) 0.0429(13) 0.0189(12) -0.0141(12) -0.0302(14) C4 0.080(2) 0.071(2) 0.0585(19) 0.0232(16) -0.0193(17) -0.048(2) C5 0.106(4) 0.079(3) 0.070(2) 0.037(2) -0.025(2) -0.059(3) C6 0.0544(16) 0.0607(17) 0.0386(12) 0.0147(12) -0.0100(11) -0.0274(14) C7 0.071(2) 0.0581(17) 0.0395(13) 0.0111(12) -0.0134(13) -0.0277(16) C8 0.068(2) 0.0587(18) 0.0434(14) 0.0148(13) -0.0132(13) -0.0252(16) C9 0.0495(15) 0.0701(19) 0.0362(12) 0.0186(12) -0.0081(10) -0.0226(14) C10 0.071(2) 0.080(2) 0.0361(13) 0.0157(14) -0.0123(13) -0.0378(19) C11 0.081(2) 0.075(2) 0.0389(13) 0.0147(14) -0.0161(14) -0.042(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C9 2.094(3) . ? O1 C2 1.230(4) . ? O2 C4 1.233(5) . ? N1 N2 1.299(4) . ? N1 C3 1.319(4) . ? N2 C6 1.382(4) . ? N2 H2 0.8800 . ? C1 C2 1.498(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.494(5) . ? C3 C4 1.462(6) . ? C4 C5 1.506(6) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C11 1.400(4) . ? C6 C7 1.410(5) . ? C7 C8 1.376(5) . ? C7 H7 0.9500 . ? C8 C9 1.400(5) . ? C8 H8 0.9500 . ? C9 C10 1.386(6) . ? C10 C11 1.392(5) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? 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 N1 C3 121.5(3) . . ? N1 N2 C6 120.4(3) . . ? N1 N2 H2 119.8 . . ? C6 N2 H2 119.8 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 121.1(4) . . ? O1 C2 C1 119.9(3) . . ? C3 C2 C1 119.0(3) . . ? N1 C3 C4 124.2(3) . . ? N1 C3 C2 112.3(3) . . ? C4 C3 C2 123.5(3) . . ? O2 C4 C3 118.7(4) . . ? O2 C4 C5 118.8(4) . . ? C3 C4 C5 122.4(4) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 C11 118.7(3) . . ? N2 C6 C7 122.0(3) . . ? C11 C6 C7 119.3(3) . . ? C8 C7 C6 120.4(3) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 119.9(3) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C10 C9 C8 120.4(3) . . ? C10 C9 I1 120.5(2) . . ? C8 C9 I1 119.1(3) . . ? C9 C10 C11 120.0(3) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C6 120.1(4) . . ? C10 C11 H11 120.0 . . ? C6 C11 H11 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 N2 C6 -179.1(3) . . . . ? N2 N1 C3 C4 -4.0(5) . . . . ? N2 N1 C3 C2 176.5(3) . . . . ? O1 C2 C3 N1 -164.1(4) . . . . ? C1 C2 C3 N1 16.6(5) . . . . ? O1 C2 C3 C4 16.3(6) . . . . ? C1 C2 C3 C4 -163.0(4) . . . . ? N1 C3 C4 O2 0.7(7) . . . . ? C2 C3 C4 O2 -179.8(4) . . . . ? N1 C3 C4 C5 -175.7(4) . . . . ? C2 C3 C4 C5 3.8(7) . . . . ? N1 N2 C6 C11 168.0(3) . . . . ? N1 N2 C6 C7 -13.0(5) . . . . ? N2 C6 C7 C8 -178.0(3) . . . . ? C11 C6 C7 C8 1.0(6) . . . . ? C6 C7 C8 C9 -1.2(6) . . . . ? C7 C8 C9 C10 1.0(6) . . . . ? C7 C8 C9 I1 178.2(3) . . . . ? C8 C9 C10 C11 -0.5(6) . . . . ? I1 C9 C10 C11 -177.7(3) . . . . ? C9 C10 C11 C6 0.3(6) . . . . ? N2 C6 C11 C10 178.6(3) . . . . ? C7 C6 C11 C10 -0.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 34.84 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.042 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.120 # TEXT _publ_section_abstract ; Three new hydrazone compounds having a p-iodoaryl and diketohydrazone molecular skeleton in common but feature a gradual replacement of the two methyl for trifluoromethyl terminal groups were prepared and comparatively studied with regard to their crystal structures. A quantum chemical calculation of the single trifluoromethyl modified compound was undertaken to decide on to low energy conformation referring to the hydrogen bonded ring site. While the molecular structures of the compounds remain rather unimpaired by the fluorine substitution, their crystalline packings are markedly affected, showing a distinct supramolecular control in the crystal lattices. ; # Attachment '3.cif' data_jama40c _database_code_depnum_ccdc_archive 'CCDC 661393' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H20 F24 I4 N8 O8' _chemical_formula_weight 1752.28 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 tetragonal _symmetry_space_group_name_H-M 'P -4 2(1) c' _symmetry_space_group_name_Hall 'P -4 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '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+1/2' 'y+1/2, x+1/2, z+1/2' _cell_length_a 19.9387(6) _cell_length_b 19.9387(6) _cell_length_c 6.7572(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2686.34(17) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description column _exptl_crystal_colour red _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.166 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 2.464 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.4160 _exptl_absorpt_correction_T_max 0.7080 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 109881 _diffrn_reflns_av_R_equivalents 0.0765 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 35.54 _reflns_number_total 6149 _reflns_number_gt 5201 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART APEX2 (Bruker-AXS)' _computing_cell_refinement 'SAINT-NT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.005(16) _refine_ls_number_reflns 6149 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1057 _refine_ls_wR_factor_gt 0.0980 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 0.997579(9) 0.397577(9) -0.01159(3) 0.02995(6) Uani 1 1 d . . . F1 F 0.83719(8) 0.78621(8) 1.2951(3) 0.0269(3) Uani 1 1 d . . . F2 F 0.83055(8) 0.71691(7) 1.0525(3) 0.0320(4) Uani 1 1 d . . . F3 F 0.74541(8) 0.77810(8) 1.1242(3) 0.0279(3) Uani 1 1 d . . . F4 F 0.95318(8) 0.91721(9) 0.7818(2) 0.0288(3) Uani 1 1 d . . . F5 F 0.87470(9) 0.91574(11) 0.5610(2) 0.0397(4) Uani 1 1 d . . . F6 F 0.91790(9) 1.00945(10) 0.6544(3) 0.0445(5) Uani 1 1 d . . . O1 O 0.86840(11) 0.81042(11) 0.8193(3) 0.0322(4) Uani 1 1 d . . . O2 O 0.82397(10) 1.01396(9) 0.9078(3) 0.0251(4) Uani 1 1 d . . . N1 N 0.78951(10) 0.91021(10) 1.1719(3) 0.0181(4) Uani 1 1 d . . . N2 N 0.77067(10) 0.96831(10) 1.2344(3) 0.0199(4) Uani 1 1 d . . . H2 H 0.7777(15) 1.0018(14) 1.159(3) 0.015(6) Uiso 1 1 d . . . C1 C 0.81279(13) 0.77762(13) 1.1127(4) 0.0219(4) Uani 1 1 d . . . C2 C 0.83847(12) 0.83088(13) 0.9625(4) 0.0212(5) Uani 1 1 d . . . C3 C 0.82456(11) 0.90140(11) 1.0068(4) 0.0188(4) Uani 1 1 d . . . C4 C 0.84552(12) 0.95757(13) 0.8819(3) 0.0216(4) Uani 1 1 d . . . C5 C 0.89864(13) 0.94876(15) 0.7155(4) 0.0271(5) Uani 1 1 d . . . C6 C 0.97330(12) 0.26509(11) 0.5850(4) 0.0183(4) Uani 1 1 d . . . C7 C 0.91657(11) 0.27933(11) 0.4728(4) 0.0198(4) Uani 1 1 d . . . H7 H 0.8737 0.2635 0.5130 0.024 Uiso 1 1 calc R . . C8 C 0.92346(12) 0.31716(12) 0.3005(4) 0.0208(4) Uani 1 1 d . . . H8 H 0.8852 0.3280 0.2229 0.025 Uiso 1 1 calc R . . C9 C 0.98691(11) 0.33880(11) 0.2433(4) 0.0200(4) Uani 1 1 d . . . C10 C 1.04373(12) 0.32345(12) 0.3538(4) 0.0219(5) Uani 1 1 d . . . H10 H 1.0867 0.3382 0.3115 0.026 Uiso 1 1 calc R . . C11 C 1.03699(11) 0.28612(12) 0.5274(4) 0.0217(4) Uani 1 1 d . . . H11 H 1.0752 0.2752 0.6049 0.026 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 0.02854(9) 0.02524(8) 0.03607(10) 0.01587(6) 0.00473(10) 0.00111(6) F1 0.0297(8) 0.0272(8) 0.0239(7) -0.0003(6) -0.0021(6) 0.0042(6) F2 0.0362(8) 0.0192(7) 0.0406(9) -0.0065(6) -0.0005(7) 0.0060(6) F3 0.0169(7) 0.0244(7) 0.0423(9) -0.0017(7) 0.0039(6) -0.0038(6) F4 0.0156(7) 0.0371(9) 0.0338(8) 0.0081(7) -0.0003(6) 0.0014(6) F5 0.0250(8) 0.0731(13) 0.0210(8) -0.0034(8) 0.0011(6) 0.0093(8) F6 0.0388(10) 0.0442(11) 0.0506(10) 0.0293(9) 0.0177(8) 0.0038(8) O1 0.0334(10) 0.0340(10) 0.0293(10) -0.0117(8) 0.0123(8) -0.0031(9) O2 0.0325(10) 0.0199(8) 0.0231(8) 0.0013(6) 0.0015(7) -0.0032(7) N1 0.0181(9) 0.0177(8) 0.0184(9) -0.0018(7) 0.0016(7) -0.0002(7) N2 0.0230(9) 0.0150(8) 0.0217(9) 0.0014(7) 0.0022(7) 0.0001(7) C1 0.0209(11) 0.0200(11) 0.0247(11) -0.0031(9) 0.0002(9) 0.0035(9) C2 0.0139(9) 0.0268(11) 0.0229(13) -0.0054(9) 0.0019(8) -0.0008(9) C3 0.0176(9) 0.0213(9) 0.0175(9) -0.0026(8) 0.0017(8) -0.0017(7) C4 0.0190(10) 0.0285(12) 0.0173(10) 0.0025(8) -0.0019(8) -0.0015(9) C5 0.0177(11) 0.0392(14) 0.0244(11) 0.0110(10) 0.0035(9) 0.0006(10) C6 0.0186(9) 0.0160(9) 0.0202(10) 0.0034(7) 0.0005(8) 0.0000(8) C7 0.0181(9) 0.0164(9) 0.0249(11) 0.0019(8) 0.0025(8) 0.0001(7) C8 0.0181(10) 0.0186(10) 0.0257(11) 0.0041(8) 0.0001(8) 0.0009(8) C9 0.0211(11) 0.0146(9) 0.0242(10) 0.0046(8) 0.0040(8) 0.0018(7) C10 0.0203(11) 0.0177(10) 0.0276(12) 0.0025(9) 0.0039(9) -0.0011(9) C11 0.0162(9) 0.0251(10) 0.0238(11) 0.0047(9) 0.0003(8) -0.0002(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 I1 C9 2.094(2) . ? F1 C1 1.336(3) . ? F2 C1 1.325(3) . ? F3 C1 1.346(3) . ? F4 C5 1.334(3) . ? F5 C5 1.324(3) . ? F6 C5 1.335(3) . ? O1 C2 1.208(3) . ? O2 C4 1.216(3) . ? N1 N2 1.289(3) . ? N1 C3 1.328(3) . ? N2 C6 1.417(3) 4_657 ? N2 H2 0.85(3) . ? C1 C2 1.556(4) . ? C2 C3 1.464(3) . ? C3 C4 1.463(3) . ? C4 C5 1.554(4) . ? C6 C7 1.391(3) . ? C6 C11 1.393(3) . ? C6 N2 1.417(3) 3_567 ? C10 C11 1.395(3) . ? C11 H11 0.9500 . ? C9 C10 1.391(3) . ? C10 H10 0.9500 . ? C8 C9 1.391(3) . ? C7 C8 1.394(3) . ? C8 H8 0.9500 . ? C7 H7 0.9500 . ? 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 N1 C3 123.2(2) . . ? N1 N2 C6 119.47(19) . 4_657 ? N1 N2 H2 117.5(18) . . ? C6 N2 H2 122.8(18) 4_657 . ? F2 C1 F1 107.6(2) . . ? F2 C1 F3 106.9(2) . . ? F1 C1 F3 108.0(2) . . ? F2 C1 C2 109.6(2) . . ? F1 C1 C2 113.2(2) . . ? F3 C1 C2 111.2(2) . . ? O1 C2 C3 125.6(3) . . ? O1 C2 C1 117.1(2) . . ? C3 C2 C1 117.37(19) . . ? N1 C3 C4 122.2(2) . . ? N1 C3 C2 113.5(2) . . ? C4 C3 C2 124.3(2) . . ? O2 C4 C3 121.6(2) . . ? O2 C4 C5 116.7(2) . . ? C3 C4 C5 121.7(2) . . ? F5 C5 F4 108.9(2) . . ? F5 C5 F6 108.1(2) . . ? F4 C5 F6 107.3(2) . . ? F5 C5 C4 112.4(2) . . ? F4 C5 C4 111.5(2) . . ? F6 C5 C4 108.5(2) . . ? C7 C6 C11 121.8(2) . . ? C7 C6 N2 121.0(2) . 3_567 ? C11 C6 N2 117.2(2) . 3_567 ? C6 C11 C10 118.9(2) . . ? C6 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C9 C10 C11 119.3(2) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C8 C9 C10 121.6(2) . . ? C10 C9 I1 118.81(17) . . ? C8 C9 I1 119.62(17) . . ? C7 C8 C9 119.3(2) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C6 C7 C8 119.1(2) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? 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 N2 C6 -178.4(2) . . . 4_657 ? F2 C1 C2 O1 0.9(3) . . . . ? F1 C1 C2 O1 121.1(3) . . . . ? F3 C1 C2 O1 -117.0(3) . . . . ? F2 C1 C2 C3 -178.9(2) . . . . ? F1 C1 C2 C3 -58.7(3) . . . . ? F3 C1 C2 C3 63.2(3) . . . . ? N2 N1 C3 C4 0.7(3) . . . . ? N2 N1 C3 C2 -178.3(2) . . . . ? O1 C2 C3 N1 178.7(2) . . . . ? C1 C2 C3 N1 -1.5(3) . . . . ? O1 C2 C3 C4 -0.2(4) . . . . ? C1 C2 C3 C4 179.6(2) . . . . ? N1 C3 C4 O2 -10.5(4) . . . . ? C2 C3 C4 O2 168.3(2) . . . . ? N1 C3 C4 C5 166.8(2) . . . . ? C2 C3 C4 C5 -14.4(3) . . . . ? O2 C4 C5 F5 -109.4(3) . . . . ? C3 C4 C5 F5 73.1(3) . . . . ? O2 C4 C5 F4 127.9(3) . . . . ? C3 C4 C5 F4 -49.5(3) . . . . ? O2 C4 C5 F6 10.0(3) . . . . ? C3 C4 C5 F6 -167.4(2) . . . . ? C7 C6 C11 C10 1.1(4) . . . . ? N2 C6 C11 C10 -177.9(2) 3_567 . . . ? C6 C11 C10 C9 0.1(4) . . . . ? C8 C9 C10 C11 -0.8(4) . . . . ? C11 C10 C9 I1 177.98(18) . . . . ? C7 C8 C9 C10 0.2(4) . . . . ? I1 C9 C8 C7 -178.56(17) . . . . ? C11 C6 C7 C8 -1.7(4) . . . . ? N2 C6 C7 C8 177.2(2) 3_567 . . . ? C6 C7 C8 C9 1.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 35.54 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.050 _refine_diff_density_min -1.490 _refine_diff_density_rms 0.151