Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Maria Gdaniec' 'Maria J. Milewska' 'Barbera Piotrkowska' 'Tadeusz Polonski' _publ_contact_author_name 'Maria Gdaniec' _publ_contact_author_address ; Department of Crystallography Adam Mickiewicz University Faculty of Chemistry Grunwaldzka 6 Poznan 60-780 POLAND ; _publ_contact_author_email MAGDAN@AMU.EDU.PL _publ_requested_journal CrystEngComm _publ_section_title ; Aryl-Perfluoroaryl Stacking Interactions, Hydrogen Bonding and Steric Effects in Controlling the Structure of Supramolecular Assemblies of N,N'-Diaryloxalamides ; data_2 _database_code_depnum_ccdc_archive 'CCDC 652024' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-dimesitylethanediamide ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H24 N2 O2' _chemical_formula_sum 'C20 H24 N2 O2' _chemical_formula_weight 324.41 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 0.0000 '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' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 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 7.802(3) _cell_length_b 8.471(3) _cell_length_c 8.709(3) _cell_angle_alpha 114.30(4) _cell_angle_beta 96.46(3) _cell_angle_gamma 114.38(4) _cell_volume 449.3(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5341 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 174 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'KumaCCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% negligible _diffrn_reflns_number 4511 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1584 _reflns_number_gt 1187 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_cell_refinement ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_data_reduction ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'Stereochemical Workstation (Siemens Analytical X-Ray Instruments, Inc., 1989)' ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-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^)+(0.0989P)^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 SHELXL _refine_ls_extinction_coef 0.08(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1584 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1530 _refine_ls_wR_factor_gt 0.1418 _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 O1 O 0.3775(2) 0.51729(19) 0.15679(18) 0.0689(5) Uani 1 1 d . . . N1 N 0.4770(2) 0.2926(2) 0.02071(19) 0.0527(4) Uani 1 1 d . . . H1N H 0.5365 0.2596 -0.0622 0.072(6) Uiso 1 1 d R . . C1 C 0.4556(2) 0.4509(2) 0.0536(2) 0.0491(5) Uani 1 1 d . . . C2 C 0.3909(2) 0.1622(2) 0.0898(2) 0.0450(4) Uani 1 1 d . . . C3 C 0.2233(2) -0.0264(2) -0.0261(2) 0.0485(5) Uani 1 1 d . . . C4 C 0.1410(2) -0.1515(2) 0.0425(2) 0.0535(5) Uani 1 1 d . . . H4 H 0.0296 -0.2787 -0.0334 0.072(6) Uiso 1 1 calc R . . C5 C 0.2192(3) -0.0929(2) 0.2192(2) 0.0530(5) Uani 1 1 d . . . C6 C 0.3874(3) 0.0957(2) 0.3302(2) 0.0525(5) Uani 1 1 d . . . H6 H 0.4419 0.1363 0.4495 0.062(5) Uiso 1 1 calc R . . C7 C 0.4773(2) 0.2265(2) 0.2682(2) 0.0487(5) Uani 1 1 d . . . C8 C 0.1297(3) -0.0941(3) -0.2191(2) 0.0688(6) Uani 1 1 d . . . H8A H -0.0233 -0.2088 -0.2658 0.103 Uiso 0.80(2) 1 d PR . . H8B H 0.1038 0.0155 -0.2108 0.103 Uiso 0.80(2) 1 d PR . . H8C H 0.2306 -0.1066 -0.2848 0.103 Uiso 0.80(2) 1 d PR . . H8D H 0.2270 -0.0266 -0.2620 0.103 Uiso 0.20(2) 1 d PR . . H8E H 0.0225 -0.0674 -0.2328 0.103 Uiso 0.20(2) 1 d PR . . H8F H 0.0694 -0.2680 -0.2970 0.103 Uiso 0.20(2) 1 d PR . . C9 C 0.1189(3) -0.2292(3) 0.2909(3) 0.0760(6) Uani 1 1 d . . . H9A H 0.0055 -0.3528 0.1958 0.114 Uiso 0.58(2) 1 d PR . . H9B H 0.2128 -0.2570 0.3389 0.114 Uiso 0.58(2) 1 d PR . . H9C H 0.0754 -0.1641 0.3837 0.114 Uiso 0.58(2) 1 d PR . . H9D H 0.1413 -0.3847 0.2247 0.114 Uiso 0.42(2) 1 d PR . . H9E H -0.0212 -0.2714 0.2603 0.114 Uiso 0.42(2) 1 d PR . . H9F H 0.1765 -0.1555 0.4197 0.114 Uiso 0.42(2) 1 d PR . . C10 C 0.6621(3) 0.4287(3) 0.3915(2) 0.0663(6) Uani 1 1 d . . . H10C H 0.7781 0.4391 0.3359 0.099 Uiso 1 1 d R . . H10B H 0.6379 0.5380 0.4023 0.099 Uiso 1 1 d R . . H10A H 0.6911 0.4411 0.5044 0.099 Uiso 1 1 d 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 O1 0.0879(10) 0.0730(9) 0.0917(9) 0.0567(8) 0.0588(8) 0.0562(8) N1 0.0613(9) 0.0513(8) 0.0678(9) 0.0382(7) 0.0357(8) 0.0353(8) C1 0.0482(10) 0.0479(9) 0.0598(10) 0.0308(8) 0.0225(8) 0.0268(8) C2 0.0481(9) 0.0432(9) 0.0580(10) 0.0298(8) 0.0253(8) 0.0287(8) C3 0.0491(10) 0.0457(9) 0.0538(9) 0.0216(8) 0.0203(8) 0.0295(8) C4 0.0470(10) 0.0380(9) 0.0655(11) 0.0202(8) 0.0187(8) 0.0194(8) C5 0.0544(10) 0.0491(9) 0.0721(11) 0.0370(9) 0.0308(9) 0.0313(8) C6 0.0553(10) 0.0533(10) 0.0574(10) 0.0326(8) 0.0188(8) 0.0302(9) C7 0.0447(9) 0.0416(9) 0.0587(10) 0.0245(8) 0.0159(8) 0.0223(8) C8 0.0727(13) 0.0713(12) 0.0575(11) 0.0255(10) 0.0183(9) 0.0406(11) C9 0.0815(14) 0.0681(13) 0.1027(16) 0.0596(12) 0.0431(12) 0.0385(12) C10 0.0565(12) 0.0508(10) 0.0710(12) 0.0273(9) 0.0091(9) 0.0170(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 O1 C1 1.2189(19) . ? N1 C1 1.337(2) . ? N1 C2 1.435(2) . ? N1 H1N 0.9123 . ? C1 C1 1.533(3) 2_665 ? C2 C7 1.390(2) . ? C2 C3 1.390(3) . ? C3 C4 1.391(2) . ? C3 C8 1.508(3) . ? C4 C5 1.378(3) . ? C4 H4 0.9300 . ? C5 C6 1.386(3) . ? C5 C9 1.514(2) . ? C6 C7 1.395(2) . ? C6 H6 0.9300 . ? C7 C10 1.505(3) . ? C8 H8A 1.0689 . ? C8 H8B 1.0049 . ? C8 H8C 1.0393 . ? C8 H8D 0.9609 . ? C8 H8E 0.9594 . ? C8 H8F 1.1775 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C9 H9D 1.2983 . ? C9 H9E 0.9626 . ? C9 H9F 0.9641 . ? C10 H10C 1.0629 . ? C10 H10B 0.9897 . ? C10 H10A 0.9350 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 123.90(14) . . ? C1 N1 H1N 115.9 . . ? C2 N1 H1N 119.7 . . ? O1 C1 N1 126.25(15) . . ? O1 C1 C1 121.27(17) . 2_665 ? N1 C1 C1 112.48(17) . 2_665 ? C7 C2 C3 122.14(15) . . ? C7 C2 N1 119.51(15) . . ? C3 C2 N1 118.35(14) . . ? C2 C3 C4 117.82(15) . . ? C2 C3 C8 121.71(16) . . ? C4 C3 C8 120.46(16) . . ? C5 C4 C3 122.12(16) . . ? C5 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? C4 C5 C6 118.33(16) . . ? C4 C5 C9 120.47(17) . . ? C6 C5 C9 121.16(16) . . ? C5 C6 C7 121.98(16) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C2 C7 C6 117.60(16) . . ? C2 C7 C10 121.85(16) . . ? C6 C7 C10 120.55(15) . . ? C3 C8 H8A 108.4 . . ? C3 C8 H8B 103.5 . . ? H8A C8 H8B 96.9 . . ? C3 C8 H8C 108.4 . . ? H8A C8 H8C 124.5 . . ? H8B C8 H8C 113.0 . . ? C3 C8 H8D 110.9 . . ? C3 C8 H8E 110.8 . . ? H8D C8 H8E 108.9 . . ? C3 C8 H8F 104.6 . . ? H8D C8 H8F 110.8 . . ? H8E C8 H8F 110.9 . . ? C5 C9 H9A 109.7 . . ? C5 C9 H9B 109.2 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.6 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C9 H9D 110.3 . . ? C5 C9 H9E 109.4 . . ? H9D C9 H9E 110.1 . . ? C5 C9 H9F 109.3 . . ? H9E C9 H9F 107.6 . . ? C7 C10 H10C 108.8 . . ? C7 C10 H10B 110.8 . . ? H10C C10 H10B 107.3 . . ? C7 C10 H10A 107.1 . . ? H10C C10 H10A 114.5 . . ? H10B C10 H10A 108.4 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1 0.91 2.25 2.684(2) 108.7 2_665 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.213 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.035 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 652025' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(3,5-dimethylphenyl)ethanediamide ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N2 O2' _chemical_formula_sum 'C18 H20 N2 O2' _chemical_formula_weight 296.36 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.8750(13) _cell_length_b 4.7200(7) _cell_length_c 15.978(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.312(11) _cell_angle_gamma 90.00 _cell_volume 783.02(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5668 _cell_measurement_theta_min 4 _cell_measurement_theta_max 50 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'KumaCCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% negligible _diffrn_reflns_number 7563 _diffrn_reflns_av_R_equivalents 0.0849 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.74 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1366 _reflns_number_gt 1210 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_cell_refinement ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_data_reduction ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'Stereochemical Workstation (Siemens Analytical X-Ray Instruments, Inc., 1989)' ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-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^)+(0.0869P)^2^+0.0483P] 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 SHELXL _refine_ls_extinction_coef 0.041(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1366 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1345 _refine_ls_wR_factor_gt 0.1293 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 O1 O 0.10978(10) 0.3435(2) -0.04640(6) 0.0495(4) Uani 1 1 d . . . N1 N 0.07294(11) 0.2614(2) 0.08563(7) 0.0403(4) Uani 1 1 d . . . H1 H 0.0248 0.3313 0.1178 0.050(4) Uiso 1 1 d R . . C1 C 0.05390(12) 0.3885(2) 0.00792(8) 0.0370(4) Uani 1 1 d . . . C2 C 0.16368(12) 0.0513(3) 0.12654(8) 0.0353(4) Uani 1 1 d . . . C3 C 0.16202(13) -0.0429(3) 0.20867(9) 0.0400(4) Uani 1 1 d . . . H3 H 0.0988 0.0402 0.2362 0.053(4) Uiso 1 1 d R . . C4 C 0.24864(14) -0.2467(3) 0.25334(8) 0.0408(4) Uani 1 1 d . . . C5 C 0.33695(13) -0.3543(3) 0.21404(9) 0.0416(4) Uani 1 1 d . . . H5 H 0.3983 -0.4935 0.2465 0.058(4) Uiso 1 1 d R . . C6 C 0.33943(13) -0.2642(3) 0.13205(9) 0.0394(4) Uani 1 1 d . . . C7 C 0.25132(12) -0.0598(3) 0.08791(8) 0.0376(4) Uani 1 1 d . . . H7 H 0.2517 0.0032 0.0311 0.039(4) Uiso 1 1 d R . . C8 C 0.24630(17) -0.3501(4) 0.34162(10) 0.0575(5) Uani 1 1 d . . . H81 H 0.1800 -0.4738 0.3393 0.077(9) Uiso 0.75(4) 1 d PR . . H82 H 0.2241 -0.2078 0.3795 0.067(8) Uiso 0.75(4) 1 d PR . . H83 H 0.3274 -0.4178 0.3760 0.052(7) Uiso 0.75(4) 1 d PR . . H81' H 0.2666 -0.5751 0.3461 0.033(18) Uiso 0.25(4) 1 d PR . . H82' H 0.1631 -0.3146 0.3491 0.045(19) Uiso 0.25(4) 1 d PR . . H83' H 0.3097 -0.2506 0.3869 0.06(3) Uiso 0.25(4) 1 d PR . . C9 C 0.43326(15) -0.3867(4) 0.09000(11) 0.0551(5) Uani 1 1 d . . . H91 H 0.4614 -0.2397 0.0515 0.058(8) Uiso 0.71(4) 1 d PR . . H92 H 0.3921 -0.5013 0.0400 0.063(9) Uiso 0.71(4) 1 d PR . . H93 H 0.5018 -0.4280 0.1279 0.063(9) Uiso 0.71(4) 1 d PR . . H91' H 0.4452 -0.6133 0.1007 0.045(18) Uiso 0.29(4) 1 d PR . . H92' H 0.5152 -0.2948 0.1133 0.07(2) Uiso 0.29(4) 1 d PR . . H93' H 0.4038 -0.3496 0.0280 0.09(2) Uiso 0.29(4) 1 d PR . . 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 O1 0.0526(7) 0.0538(7) 0.0462(6) 0.0065(5) 0.0212(5) 0.0119(5) N1 0.0402(7) 0.0419(7) 0.0407(7) 0.0033(5) 0.0149(5) 0.0056(5) C1 0.0360(7) 0.0340(7) 0.0399(8) -0.0027(5) 0.0096(6) -0.0041(5) C2 0.0339(7) 0.0334(7) 0.0368(7) -0.0021(5) 0.0077(5) -0.0022(5) C3 0.0399(8) 0.0424(7) 0.0391(8) -0.0021(6) 0.0141(6) -0.0002(6) C4 0.0410(8) 0.0444(8) 0.0356(8) -0.0007(5) 0.0091(6) -0.0034(6) C5 0.0385(8) 0.0435(8) 0.0385(8) 0.0021(6) 0.0048(6) 0.0031(6) C6 0.0349(7) 0.0423(8) 0.0399(8) -0.0043(6) 0.0093(6) -0.0008(5) C7 0.0380(8) 0.0418(8) 0.0326(7) -0.0006(5) 0.0099(6) -0.0028(6) C8 0.0611(11) 0.0705(11) 0.0422(9) 0.0098(8) 0.0177(8) 0.0109(9) C9 0.0471(10) 0.0701(11) 0.0499(10) 0.0011(8) 0.0172(8) 0.0136(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 O1 C1 1.2172(16) . ? N1 C1 1.3384(16) . ? N1 C2 1.4146(17) . ? N1 H1 0.8985 . ? C1 C1 1.539(2) 3_565 ? C2 C7 1.3836(19) . ? C2 C3 1.3909(18) . ? C3 C4 1.386(2) . ? C3 H3 1.0003 . ? C4 C5 1.390(2) . ? C4 C8 1.500(2) . ? C5 C6 1.385(2) . ? C5 H5 0.9698 . ? C6 C7 1.3946(18) . ? C6 C9 1.495(2) . ? C7 H7 0.9559 . ? C8 H81 0.9202 . ? C8 H82 0.9811 . ? C8 H83 0.9456 . ? C8 H81' 1.0824 . ? C8 H82' 0.9619 . ? C8 H83' 0.9606 . ? C9 H91 1.0319 . ? C9 H92 0.9581 . ? C9 H93 0.8316 . ? C9 H91' 1.0850 . ? C9 H92' 0.9610 . ? C9 H93' 0.9622 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 129.57(11) . . ? C1 N1 H1 114.2 . . ? C2 N1 H1 116.0 . . ? O1 C1 N1 127.66(12) . . ? O1 C1 C1 121.29(14) . 3_565 ? N1 C1 C1 111.04(14) . 3_565 ? C7 C2 C3 120.26(12) . . ? C7 C2 N1 122.54(12) . . ? C3 C2 N1 117.20(11) . . ? C4 C3 C2 120.67(12) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 118.42(12) . . ? C3 C4 C8 120.72(13) . . ? C5 C4 C8 120.86(12) . . ? C6 C5 C4 121.69(12) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 117.6 . . ? C5 C6 C7 119.14(12) . . ? C5 C6 C9 120.96(13) . . ? C7 C6 C9 119.90(13) . . ? C2 C7 C6 119.83(12) . . ? C2 C7 H7 120.2 . . ? C6 C7 H7 119.9 . . ? C4 C8 H81 113.7 . . ? C4 C8 H82 115.7 . . ? H81 C8 H82 97.2 . . ? C4 C8 H83 112.5 . . ? H81 C8 H83 113.2 . . ? H82 C8 H83 103.3 . . ? C4 C8 H81' 108.8 . . ? H81 C8 H81' 61.4 . . ? H82 C8 H81' 135.5 . . ? H83 C8 H81' 59.6 . . ? C4 C8 H82' 109.9 . . ? H81 C8 H82' 50.2 . . ? H82 C8 H82' 52.5 . . ? H83 C8 H82' 137.4 . . ? H81' C8 H82' 110.1 . . ? C4 C8 H83' 109.9 . . ? H81 C8 H83' 135.9 . . ? H82 C8 H83' 56.9 . . ? H83 C8 H83' 52.5 . . ? H81' C8 H83' 110.1 . . ? H82' C8 H83' 108.1 . . ? C6 C9 H91 111.7 . . ? C6 C9 H92 112.4 . . ? H91 C9 H92 91.8 . . ? C6 C9 H93 110.3 . . ? H91 C9 H93 103.4 . . ? H92 C9 H93 124.7 . . ? C6 C9 H91' 112.1 . . ? H91 C9 H91' 135.6 . . ? H92 C9 H91' 65.1 . . ? H93 C9 H91' 67.3 . . ? C6 C9 H92' 109.2 . . ? H91 C9 H92' 61.5 . . ? H92 C9 H92' 136.7 . . ? H93 C9 H92' 45.3 . . ? H91' C9 H92' 109.3 . . ? C6 C9 H93' 109.3 . . ? H91 C9 H93' 48.0 . . ? H92 C9 H93' 46.7 . . ? H93 C9 H93' 138.0 . . ? H91' C9 H93' 109.2 . . ? H92' C9 H93' 107.6 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C7 H7 O1 0.96 2.31 2.9380(16) 122.2 . N1 H1 O1 0.90 2.19 2.6602(14) 111.8 3_565 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.151 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.043 #===END data_1pfp _database_code_depnum_ccdc_archive 'CCDC 652026' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-diphenylethanediamide 2,3,4,5,6-pentafluorophenol 1:2 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 N2 O2, 2(C6 H F5 O)' _chemical_formula_sum 'C26 H14 F10 N2 O4' _chemical_formula_weight 608.39 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.9263(5) _cell_length_b 5.6969(5) _cell_length_c 21.2570(13) _cell_angle_alpha 90.00 _cell_angle_beta 94.431(5) _cell_angle_gamma 90.00 _cell_volume 1198.47(14) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 3790 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.686 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 0.166 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 'KumaCCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% negligible _diffrn_reflns_number 7434 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_sigmaI/netI 0.0131 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2112 _reflns_number_gt 1866 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_cell_refinement ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_data_reduction ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'Stereochemical Workstation (Siemens Analytical X-Ray Instruments, Inc., 1989)' ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-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^)+(0.0658P)^2^+0.8916P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2112 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1289 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 O1 O 0.34661(13) 1.0280(3) 0.45374(7) 0.0319(4) Uani 1 1 d . . . N1 N 0.54165(15) 1.2414(3) 0.45175(7) 0.0253(4) Uani 1 1 d . . . H1N H 0.6190 1.2529 0.4717 0.029(6) Uiso 1 1 d R . . C1 C 0.46363(19) 1.0717(3) 0.47298(9) 0.0239(4) Uani 1 1 d . . . C2 C 0.50939(18) 1.4055(3) 0.40260(9) 0.0235(4) Uani 1 1 d . . . C3 C 0.59702(19) 1.5951(3) 0.39833(9) 0.0265(4) Uani 1 1 d . . . H3A H 0.6735 1.6111 0.4278 0.032 Uiso 1 1 calc R . . C4 C 0.5721(2) 1.7597(4) 0.35108(9) 0.0304(5) Uani 1 1 d . . . H4A H 0.6322 1.8882 0.3479 0.036 Uiso 1 1 calc R . . C5 C 0.4593(2) 1.7381(4) 0.30808(9) 0.0296(5) Uani 1 1 d . . . H5A H 0.4414 1.8525 0.2760 0.036 Uiso 1 1 calc R . . C6 C 0.3736(2) 1.5481(4) 0.31274(9) 0.0293(5) Uani 1 1 d . . . H6A H 0.2969 1.5325 0.2834 0.035 Uiso 1 1 calc R . . C7 C 0.39783(19) 1.3801(4) 0.35943(9) 0.0266(4) Uani 1 1 d . . . H7A H 0.3390 1.2495 0.3619 0.032 Uiso 1 1 calc R . . O1A O 0.80064(14) 1.3736(3) 0.53710(7) 0.0398(4) Uani 1 1 d . . . H1A H 0.7701 1.2495 0.5495 0.14(2) Uiso 1 1 d R . . F2A F 0.93134(14) 1.7765(3) 0.51927(7) 0.0475(4) Uani 1 1 d . . . F3A F 1.13983(14) 1.9170(2) 0.60058(9) 0.0573(5) Uani 1 1 d . . . F4A F 1.21171(15) 1.6582(4) 0.70535(8) 0.0685(6) Uani 1 1 d . . . F5A F 1.07992(17) 1.2503(3) 0.72613(7) 0.0642(5) Uani 1 1 d . . . F6A F 0.87598(14) 1.1041(2) 0.64413(7) 0.0492(4) Uani 1 1 d . . . C1A C 0.90039(18) 1.4402(4) 0.58027(9) 0.0277(5) Uani 1 1 d . . . C2A C 0.9683(2) 1.6468(4) 0.57044(10) 0.0307(5) Uani 1 1 d . . . C3A C 1.0735(2) 1.7175(4) 0.61188(11) 0.0349(5) Uani 1 1 d . . . C4A C 1.1101(2) 1.5852(4) 0.66457(11) 0.0391(6) Uani 1 1 d . . . C5A C 1.0429(2) 1.3799(4) 0.67500(10) 0.0370(5) Uani 1 1 d . . . C6A C 0.9383(2) 1.3076(4) 0.63286(10) 0.0307(5) 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 O1 0.0250(7) 0.0331(8) 0.0368(8) 0.0066(6) -0.0030(6) -0.0060(6) N1 0.0213(8) 0.0276(9) 0.0265(8) 0.0044(7) -0.0021(6) -0.0041(6) C1 0.0238(9) 0.0226(10) 0.0253(9) -0.0008(8) 0.0015(7) -0.0009(8) C2 0.0245(9) 0.0226(10) 0.0237(9) 0.0005(7) 0.0046(7) 0.0008(7) C3 0.0254(10) 0.0256(10) 0.0285(10) -0.0015(8) 0.0015(8) -0.0024(8) C4 0.0339(11) 0.0245(10) 0.0334(11) 0.0016(8) 0.0070(8) -0.0054(8) C5 0.0338(11) 0.0273(11) 0.0282(10) 0.0052(8) 0.0052(8) 0.0050(8) C6 0.0273(10) 0.0329(11) 0.0276(10) 0.0020(8) 0.0014(8) 0.0024(8) C7 0.0261(10) 0.0263(10) 0.0273(10) 0.0006(8) 0.0018(8) -0.0027(8) O1A 0.0256(7) 0.0598(11) 0.0324(8) -0.0097(8) -0.0077(6) -0.0075(7) F2A 0.0436(8) 0.0510(9) 0.0491(8) 0.0207(7) 0.0115(6) 0.0082(6) F3A 0.0416(8) 0.0319(8) 0.1006(13) -0.0154(8) 0.0189(8) -0.0153(6) F4A 0.0413(8) 0.0983(14) 0.0621(10) -0.0455(10) -0.0198(7) 0.0044(8) F5A 0.0669(10) 0.0852(12) 0.0400(8) 0.0208(8) 0.0013(7) 0.0276(9) F6A 0.0514(8) 0.0313(7) 0.0672(9) 0.0077(7) 0.0190(7) -0.0009(6) C1A 0.0204(9) 0.0336(11) 0.0288(10) -0.0072(8) 0.0009(8) -0.0016(8) C2A 0.0292(10) 0.0304(11) 0.0331(11) 0.0027(9) 0.0069(8) 0.0034(9) C3A 0.0262(10) 0.0252(11) 0.0541(14) -0.0114(10) 0.0093(9) -0.0054(8) C4A 0.0256(10) 0.0501(14) 0.0404(12) -0.0227(11) -0.0053(9) 0.0030(10) C5A 0.0384(12) 0.0454(14) 0.0274(11) 0.0003(10) 0.0029(9) 0.0150(10) C6A 0.0328(11) 0.0236(10) 0.0372(11) -0.0005(9) 0.0119(9) 0.0021(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 O1 C1 1.227(2) . ? N1 C1 1.339(2) . ? N1 C2 1.420(2) . ? N1 H1N 0.8501 . ? C1 C1 1.543(4) 3_676 ? C2 C7 1.390(3) . ? C2 C3 1.394(3) . ? C3 C4 1.382(3) . ? C3 H3A 0.9500 . ? C4 C5 1.395(3) . ? C4 H4A 0.9500 . ? C5 C6 1.385(3) . ? C5 H5A 0.9500 . ? C6 C7 1.386(3) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? O1A C1A 1.351(2) . ? O1A H1A 0.8204 . ? F2A C2A 1.342(2) . ? F3A C3A 1.345(2) . ? F4A C4A 1.344(2) . ? F5A C5A 1.341(3) . ? F6A C6A 1.344(2) . ? C1A C6A 1.377(3) . ? C1A C2A 1.380(3) . ? C2A C3A 1.374(3) . ? C3A C4A 1.375(3) . ? C4A C5A 1.373(4) . ? C5A C6A 1.381(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 C1 N1 C2 128.31(16) . . ? C1 N1 H1N 114.3 . . ? C2 N1 H1N 117.3 . . ? O1 C1 N1 126.28(18) . . ? O1 C1 C1 121.2(2) . 3_676 ? N1 C1 C1 112.57(19) . 3_676 ? C7 C2 C3 120.45(18) . . ? C7 C2 N1 122.71(17) . . ? C3 C2 N1 116.84(17) . . ? C4 C3 C2 119.70(18) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 120.1 . . ? C3 C4 C5 120.37(18) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? C6 C5 C4 119.23(18) . . ? C6 C5 H5A 120.4 . . ? C4 C5 H5A 120.4 . . ? C5 C6 C7 121.15(18) . . ? C5 C6 H6A 119.4 . . ? C7 C6 H6A 119.4 . . ? C6 C7 C2 119.10(18) . . ? C6 C7 H7A 120.5 . . ? C2 C7 H7A 120.5 . . ? C1A O1A H1A 107.1 . . ? O1A C1A C6A 122.49(19) . . ? O1A C1A C2A 118.51(19) . . ? C6A C1A C2A 118.99(18) . . ? F2A C2A C3A 120.29(19) . . ? F2A C2A C1A 119.10(18) . . ? C3A C2A C1A 120.6(2) . . ? F3A C3A C2A 119.5(2) . . ? F3A C3A C4A 120.4(2) . . ? C2A C3A C4A 120.1(2) . . ? F4A C4A C5A 120.6(2) . . ? F4A C4A C3A 119.6(2) . . ? C5A C4A C3A 119.85(19) . . ? F5A C5A C4A 119.6(2) . . ? F5A C5A C6A 120.4(2) . . ? C4A C5A C6A 120.0(2) . . ? F6A C6A C1A 121.13(19) . . ? F6A C6A C5A 118.4(2) . . ? C1A C6A C5A 120.5(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1 0.85 2.26 2.698(2) 112.1 3_676 N1 H1N O1A 0.85 2.30 3.122(2) 164.0 . O1A H1A O1 0.82 1.96 2.730(2) 156.4 3_676 O1A H1A F6A 0.82 2.35 2.798(2) 115.3 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.345 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.055 #===END data_2pfp _database_code_depnum_ccdc_archive 'CCDC 652027' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-dimesitylethanediamide 2,3,4,5,6-pentafluorophenol 1:2 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C20 H24 N2 O2)0.5 C6F5OH' _chemical_formula_sum 'C16 H13 F5 N O2' _chemical_formula_weight 346.27 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' _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 6.9797(7) _cell_length_b 8.1338(7) _cell_length_c 15.0081(11) _cell_angle_alpha 78.383(7) _cell_angle_beta 80.223(7) _cell_angle_gamma 67.530(8) _cell_volume 767.15(12) _cell_formula_units_Z 2 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 3583 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 354 _exptl_absorpt_coefficient_mu 0.139 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 170(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 'KumaCCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% negligible _diffrn_reflns_number 5805 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 5.11 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2678 _reflns_number_gt 2084 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_cell_refinement ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_data_reduction ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'Stereochemical Workstation (Siemens Analytical X-Ray Instruments, Inc., 1989)' ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-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^)+(0.0753P)^2^+0.0431P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.037(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2678 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1293 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _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 O1 O 0.30665(19) 0.4779(2) 0.44856(9) 0.0487(4) Uani 1 1 d . . . N1 N 0.6595(2) 0.3784(2) 0.41191(10) 0.0355(4) Uani 1 1 d . . . H1N H 0.7755 0.3752 0.4292 0.045(6) Uiso 1 1 d R . . C1 C 0.4839(3) 0.4607(3) 0.46097(12) 0.0338(4) Uani 1 1 d . . . C2 C 0.6726(2) 0.3003(2) 0.33245(11) 0.0267(4) Uani 1 1 d . . . C3 C 0.7231(3) 0.1150(2) 0.34098(12) 0.0301(4) Uani 1 1 d . . . C4 C 0.7439(3) 0.0427(2) 0.26204(12) 0.0318(4) Uani 1 1 d . . . H4 H 0.7763 -0.0836 0.2690 0.043(5) Uiso 1 1 d R . . H6 H 0.654(3) 0.406(2) 0.1129(14) 0.033(5) Uiso 1 1 d . . . C5 C 0.7190(2) 0.1475(2) 0.17664(12) 0.0292(4) Uani 1 1 d . . . C6 C 0.6689(2) 0.3319(2) 0.17095(13) 0.0282(4) Uani 1 1 d . . . C7 C 0.6443(2) 0.4116(2) 0.24789(12) 0.0281(4) Uani 1 1 d . . . C8 C 0.7634(4) -0.0048(3) 0.43111(14) 0.0529(6) Uani 1 1 d . . . H8A H 0.8826 -0.0005 0.4530 0.063 Uiso 1 1 d R . . H8B H 0.7923 -0.1267 0.4235 0.063 Uiso 1 1 d R . . H8C H 0.6435 0.0337 0.4747 0.063 Uiso 1 1 d R . . C9 C 0.7502(3) 0.0620(3) 0.09229(14) 0.0452(5) Uani 1 1 d . . . H9C H 0.8954 -0.0058 0.0785 0.054 Uiso 1 1 d R . . H9A H 0.6998 0.1543 0.0418 0.054 Uiso 1 1 d R . . H9B H 0.6713 -0.0155 0.1023 0.054 Uiso 1 1 d R . . C10 C 0.5911(3) 0.6114(2) 0.23992(16) 0.0455(5) Uani 1 1 d . . . H10A H 0.6870 0.6346 0.2701 0.055 Uiso 1 1 d R . . H10B H 0.4513 0.6661 0.2670 0.055 Uiso 1 1 d R . . H10C H 0.5979 0.6626 0.1765 0.055 Uiso 1 1 d R . . O1A O 0.12965(19) 0.29970(18) 0.38132(8) 0.0376(4) Uani 1 1 d . . . H1A H 0.1756 0.3768 0.3962 0.070(8) Uiso 1 1 d R . . F2A F 0.21998(17) -0.00571(14) 0.31015(8) 0.0452(3) Uani 1 1 d . . . F3A F 0.25560(19) -0.00228(17) 0.12762(9) 0.0566(4) Uani 1 1 d . . . F4A F 0.2280(2) 0.3046(2) 0.01027(8) 0.0688(4) Uani 1 1 d . . . F5A F 0.1572(2) 0.61162(19) 0.07722(9) 0.0684(4) Uani 1 1 d . . . F6A F 0.10507(18) 0.61254(14) 0.25999(9) 0.0508(4) Uani 1 1 d . . . C1A C 0.1594(2) 0.3046(2) 0.28912(11) 0.0275(4) Uani 1 1 d . . . C2A C 0.1989(2) 0.1494(2) 0.25313(12) 0.0294(4) Uani 1 1 d . . . C3A C 0.2181(3) 0.1499(3) 0.16048(13) 0.0366(5) Uani 1 1 d . . . C4A C 0.2032(3) 0.3051(3) 0.10097(13) 0.0406(5) Uani 1 1 d . . . C5A C 0.1670(3) 0.4601(3) 0.13485(13) 0.0404(5) Uani 1 1 d . . . C6A C 0.1436(3) 0.4593(2) 0.22778(13) 0.0335(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 O1 0.0272(7) 0.0843(11) 0.0483(9) -0.0428(8) 0.0043(6) -0.0222(7) N1 0.0265(8) 0.0573(10) 0.0326(9) -0.0262(8) 0.0019(6) -0.0182(7) C1 0.0288(9) 0.0499(11) 0.0306(10) -0.0197(9) 0.0026(7) -0.0184(8) C2 0.0203(8) 0.0403(10) 0.0251(9) -0.0165(8) 0.0020(6) -0.0129(7) C3 0.0267(9) 0.0387(10) 0.0269(10) -0.0061(8) 0.0013(7) -0.0153(7) C4 0.0311(9) 0.0298(10) 0.0381(11) -0.0112(8) 0.0009(8) -0.0138(7) C5 0.0226(8) 0.0414(10) 0.0282(10) -0.0161(8) 0.0028(7) -0.0134(7) C6 0.0238(9) 0.0369(10) 0.0234(10) -0.0048(8) -0.0008(7) -0.0109(7) C7 0.0199(8) 0.0310(9) 0.0348(10) -0.0111(8) 0.0000(7) -0.0090(7) C8 0.0583(13) 0.0605(14) 0.0378(12) 0.0063(10) -0.0063(10) -0.0253(11) C9 0.0404(11) 0.0630(14) 0.0395(12) -0.0288(10) 0.0059(9) -0.0203(10) C10 0.0419(11) 0.0322(11) 0.0614(14) -0.0143(10) 0.0000(10) -0.0108(9) O1A 0.0396(7) 0.0550(8) 0.0277(7) -0.0139(6) -0.0006(5) -0.0248(6) F2A 0.0480(7) 0.0345(6) 0.0531(8) -0.0031(5) -0.0100(5) -0.0146(5) F3A 0.0512(7) 0.0621(8) 0.0629(8) -0.0410(7) -0.0060(6) -0.0116(6) F4A 0.0657(9) 0.1133(12) 0.0271(7) -0.0149(7) -0.0059(6) -0.0295(8) F5A 0.0768(10) 0.0682(9) 0.0579(9) 0.0244(7) -0.0211(7) -0.0346(8) F6A 0.0508(7) 0.0368(7) 0.0713(9) -0.0149(6) -0.0130(6) -0.0168(5) C1A 0.0196(8) 0.0400(10) 0.0263(10) -0.0091(8) -0.0026(7) -0.0121(7) C2A 0.0220(8) 0.0325(9) 0.0338(11) -0.0048(8) -0.0049(7) -0.0091(7) C3A 0.0251(9) 0.0488(12) 0.0401(12) -0.0241(10) -0.0038(8) -0.0090(8) C4A 0.0307(10) 0.0669(14) 0.0239(10) -0.0087(9) -0.0044(8) -0.0158(9) C5A 0.0328(10) 0.0498(12) 0.0367(12) 0.0087(9) -0.0103(8) -0.0175(9) C6A 0.0254(9) 0.0334(10) 0.0446(12) -0.0102(8) -0.0053(8) -0.0109(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.233(2) . ? N1 C1 1.326(2) . ? N1 C2 1.434(2) . ? N1 H1N 0.8804 . ? C1 C1 1.527(3) 2_666 ? C2 C3 1.394(2) . ? C2 C7 1.398(2) . ? C3 C4 1.389(2) . ? C3 C8 1.499(3) . ? C4 C5 1.386(3) . ? C4 H4 0.9511 . ? C5 C6 1.392(2) . ? C5 C9 1.509(2) . ? C6 C7 1.390(2) . ? C6 H6 0.95(2) . ? C7 C10 1.507(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9599 . ? C9 H9C 0.9600 . ? C9 H9A 0.9599 . ? C9 H9B 0.9601 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9601 . ? O1A C1A 1.359(2) . ? O1A H1A 0.8835 . ? F2A C2A 1.346(2) . ? F3A C3A 1.341(2) . ? F4A C4A 1.343(2) . ? F5A C5A 1.341(2) . ? F6A C6A 1.342(2) . ? C1A C6A 1.380(3) . ? C1A C2A 1.386(3) . ? C2A C3A 1.373(3) . ? C3A C4A 1.371(3) . ? C4A C5A 1.372(3) . ? C5A C6A 1.375(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 C1 N1 C2 124.94(14) . . ? C1 N1 H1N 116.5 . . ? C2 N1 H1N 118.5 . . ? O1 C1 N1 126.43(16) . . ? O1 C1 C1 119.97(19) . 2_666 ? N1 C1 C1 113.60(18) . 2_666 ? C3 C2 C7 121.97(15) . . ? C3 C2 N1 119.16(15) . . ? C7 C2 N1 118.79(16) . . ? C4 C3 C2 117.70(15) . . ? C4 C3 C8 120.50(17) . . ? C2 C3 C8 121.74(17) . . ? C5 C4 C3 122.36(16) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 116.8 . . ? C4 C5 C6 118.20(16) . . ? C4 C5 C9 120.50(17) . . ? C6 C5 C9 121.29(17) . . ? C7 C6 C5 121.82(17) . . ? C7 C6 H6 118.5(11) . . ? C5 C6 H6 119.6(11) . . ? C6 C7 C2 117.95(16) . . ? C6 C7 C10 120.83(17) . . ? C2 C7 C10 121.22(17) . . ? C3 C8 H8A 109.9 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 108.2 . . ? C3 C8 H8C 109.7 . . ? H8A C8 H8C 109.7 . . ? H8B C8 H8C 109.7 . . ? C5 C9 H9C 110.0 . . ? C5 C9 H9A 109.4 . . ? H9C C9 H9A 109.9 . . ? C5 C9 H9B 109.6 . . ? H9C C9 H9B 109.9 . . ? H9A C9 H9B 108.1 . . ? C7 C10 H10A 109.9 . . ? C7 C10 H10B 109.6 . . ? H10A C10 H10B 109.9 . . ? C7 C10 H10C 109.4 . . ? H10A C10 H10C 109.9 . . ? H10B C10 H10C 108.1 . . ? C1A O1A H1A 109.6 . . ? O1A C1A C6A 123.50(16) . . ? O1A C1A C2A 119.31(16) . . ? C6A C1A C2A 117.12(16) . . ? F2A C2A C3A 119.18(16) . . ? F2A C2A C1A 119.33(16) . . ? C3A C2A C1A 121.49(17) . . ? F3A C3A C4A 119.58(17) . . ? F3A C3A C2A 120.18(18) . . ? C4A C3A C2A 120.23(17) . . ? F4A C4A C3A 120.30(19) . . ? F4A C4A C5A 120.29(19) . . ? C3A C4A C5A 119.40(17) . . ? F5A C5A C4A 119.90(18) . . ? F5A C5A C6A 120.09(19) . . ? C4A C5A C6A 120.00(18) . . ? F6A C6A C5A 119.37(17) . . ? F6A C6A C1A 118.90(17) . . ? C5A C6A C1A 121.73(17) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1A H1A O1 0.88 1.79 2.6507(17) 163.6 . N1 H1N O1 0.88 2.26 2.6779(19) 108.6 2_666 N1 H1N O1A 0.88 2.33 3.0639(19) 141.2 1_655 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.250 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.056 #===END data_3pfp _database_code_depnum_ccdc_archive 'CCDC 652028' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2,6-dimethylphenyl)ethanediamide bis-2,3,4,5,6-pentafluorophenol ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N2 O2, 2(C6 H F5 O)' _chemical_formula_sum 'C30 H22 F10 N2 O4' _chemical_formula_weight 664.50 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.6385(9) _cell_length_b 6.9740(6) _cell_length_c 15.1543(10) _cell_angle_alpha 90.00 _cell_angle_beta 118.275(6) _cell_angle_gamma 90.00 _cell_volume 1455.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7692 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'KumaCCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% negligible _diffrn_reflns_number 7849 _diffrn_reflns_av_R_equivalents 0.0144 _diffrn_reflns_av_sigmaI/netI 0.0134 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.16 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2539 _reflns_number_gt 2130 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_cell_refinement ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_data_reduction ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'Stereochemical Workstation (Siemens Analytical X-Ray Instruments, Inc., 1989)' ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-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^)+(0.0645P)^2^+0.5503P] 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 2539 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1270 _refine_ls_wR_factor_gt 0.1207 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 O1A O 0.11544(9) 0.50829(19) 0.43528(11) 0.0424(4) Uani 1 1 d . . . H1A H 0.0978 0.4255 0.4608 0.091(11) Uiso 1 1 d R . . F2A F 0.22307(10) 0.4820(2) 0.64187(10) 0.0627(4) Uani 1 1 d . . . F3A F 0.41541(12) 0.5529(2) 0.73483(11) 0.0856(5) Uani 1 1 d . . . F4A F 0.50598(9) 0.6549(2) 0.62619(15) 0.0858(6) Uani 1 1 d . . . F5A F 0.40271(11) 0.6723(2) 0.42350(13) 0.0775(5) Uani 1 1 d . . . F6A F 0.21016(11) 0.59375(19) 0.33042(9) 0.0605(4) Uani 1 1 d . . . C1A C 0.21289(13) 0.5342(2) 0.48411(14) 0.0320(4) Uani 1 1 d . . . C2A C 0.26735(14) 0.5243(3) 0.58670(15) 0.0379(4) Uani 1 1 d . . . C3A C 0.36515(16) 0.5622(3) 0.63441(17) 0.0496(5) Uani 1 1 d . . . C4A C 0.41103(14) 0.6124(3) 0.5798(2) 0.0512(6) Uani 1 1 d . . . C5A C 0.35836(15) 0.6231(3) 0.47750(19) 0.0475(5) Uani 1 1 d . . . C6A C 0.26055(14) 0.5835(3) 0.43014(15) 0.0376(4) Uani 1 1 d . . . O1 O 0.04945(11) 1.22954(19) 0.51418(14) 0.0603(5) Uani 1 1 d . . . N1 N 0.09741(11) 0.9477(2) 0.47537(13) 0.0409(4) Uani 1 1 d . . . H1N H 0.0828 0.8346 0.4642 0.047(6) Uiso 1 1 d R . . C1 C 0.04102(14) 1.0562(3) 0.49760(17) 0.0412(5) Uani 1 1 d . . . C2 C 0.18410(12) 1.0129(2) 0.47417(13) 0.0287(4) Uani 1 1 d . . . C3 C 0.26851(13) 1.0346(2) 0.56521(14) 0.0332(4) Uani 1 1 d . . . C4 C 0.35256(13) 1.0874(3) 0.56136(15) 0.0388(5) Uani 1 1 d . . . H4 H 0.4066 1.1035 0.6210 0.048(6) Uiso 1 1 d R . . C5 C 0.35210(14) 1.1176(3) 0.47171(16) 0.0418(5) Uani 1 1 d . . . H5 H 0.4092 1.1540 0.4688 0.059(7) Uiso 1 1 d R . . C6 C 0.26767(15) 1.0986(3) 0.38312(16) 0.0407(5) Uani 1 1 d . . . H6 H 0.2691 1.1218 0.3201 0.063(7) Uiso 1 1 d R . . C7 C 0.18118(13) 1.0460(2) 0.38212(13) 0.0341(4) Uani 1 1 d . . . C8 C 0.2691(2) 1.0017(3) 0.66358(17) 0.0567(6) Uani 1 1 d . . . H8A H 0.2360 0.8842 0.6609 0.068 Uiso 1 1 d R . . H8C H 0.2360 1.1047 0.6767 0.068 Uiso 1 1 d R . . H8B H 0.3369 0.9947 0.7173 0.068 Uiso 1 1 d R . . C9 C 0.08917(17) 1.0243(4) 0.28467(17) 0.0609(6) Uani 1 1 d . . . H9A H 0.0997 1.0698 0.2308 0.073 Uiso 1 1 d R . . H9C H 0.0384 1.0997 0.2859 0.073 Uiso 1 1 d R . . H9B H 0.0686 0.8802 0.2731 0.073 Uiso 1 1 d 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 O1A 0.0286(7) 0.0394(7) 0.0548(8) 0.0028(6) 0.0163(6) -0.0037(6) F2A 0.0804(10) 0.0644(8) 0.0554(8) 0.0097(6) 0.0422(7) -0.0144(7) F3A 0.0749(10) 0.0840(11) 0.0551(9) 0.0100(7) -0.0041(7) -0.0071(8) F4A 0.0313(7) 0.0671(10) 0.1425(15) -0.0147(9) 0.0277(8) -0.0094(6) F5A 0.0905(11) 0.0616(9) 0.1335(14) -0.0167(8) 0.0964(11) -0.0143(8) F6A 0.0853(10) 0.0598(8) 0.0476(7) -0.0058(6) 0.0407(7) -0.0048(7) C1A 0.0306(9) 0.0218(8) 0.0452(10) -0.0012(7) 0.0192(8) -0.0010(7) C2A 0.0445(11) 0.0295(9) 0.0449(11) 0.0058(8) 0.0253(9) -0.0023(8) C3A 0.0449(11) 0.0353(10) 0.0506(12) 0.0025(9) 0.0079(10) -0.0013(9) C4A 0.0302(10) 0.0339(10) 0.0847(17) -0.0074(10) 0.0233(11) -0.0039(8) C5A 0.0495(12) 0.0297(10) 0.0879(17) -0.0064(10) 0.0525(13) -0.0029(9) C6A 0.0494(11) 0.0270(9) 0.0443(11) -0.0025(8) 0.0287(9) 0.0015(8) O1 0.0579(9) 0.0295(7) 0.1243(14) -0.0153(8) 0.0682(10) -0.0109(6) N1 0.0382(9) 0.0254(8) 0.0745(12) -0.0084(7) 0.0393(9) -0.0073(7) C1 0.0371(10) 0.0284(9) 0.0726(14) -0.0068(9) 0.0378(10) -0.0058(8) C2 0.0285(9) 0.0220(8) 0.0433(10) -0.0036(7) 0.0232(8) -0.0022(7) C3 0.0398(10) 0.0247(8) 0.0388(10) -0.0019(7) 0.0215(8) 0.0018(7) C4 0.0273(9) 0.0328(10) 0.0496(11) -0.0061(8) 0.0127(8) -0.0005(7) C5 0.0362(10) 0.0318(9) 0.0706(14) -0.0023(9) 0.0361(10) -0.0027(8) C6 0.0522(12) 0.0346(10) 0.0517(12) 0.0042(8) 0.0380(10) 0.0025(8) C7 0.0362(9) 0.0284(9) 0.0374(10) -0.0005(7) 0.0172(8) 0.0027(7) C8 0.0838(17) 0.0520(13) 0.0428(12) -0.0009(10) 0.0369(12) 0.0040(12) C9 0.0506(13) 0.0692(16) 0.0464(13) -0.0015(11) 0.0093(10) 0.0043(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 O1A C1A 1.354(2) . ? O1A H1A 0.8122 . ? F2A C2A 1.347(2) . ? F3A C3A 1.343(3) . ? F4A C4A 1.341(2) . ? F5A C5A 1.344(2) . ? F6A C6A 1.335(2) . ? C1A C2A 1.376(3) . ? C1A C6A 1.386(3) . ? C2A C3A 1.373(3) . ? C3A C4A 1.373(3) . ? C4A C5A 1.370(3) . ? C5A C6A 1.375(3) . ? O1 C1 1.229(2) . ? N1 C1 1.321(2) . ? N1 C2 1.438(2) . ? N1 H1N 0.8169 . ? C1 C1 1.534(3) 3_576 ? C2 C7 1.393(3) . ? C2 C3 1.394(3) . ? C3 C4 1.393(3) . ? C3 C8 1.504(3) . ? C4 C5 1.371(3) . ? C4 H4 0.9057 . ? C5 C6 1.373(3) . ? C5 H5 0.9493 . ? C6 C7 1.394(3) . ? C6 H6 0.9796 . ? C7 C9 1.504(3) . ? C8 H8A 0.9600 . ? C8 H8C 0.9601 . ? C8 H8B 0.9855 . ? C9 H9A 0.9600 . ? C9 H9C 0.9600 . ? C9 H9B 1.0445 . ? 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 C1A O1A H1A 112.5 . . ? O1A C1A C2A 123.01(17) . . ? O1A C1A C6A 119.42(17) . . ? C2A C1A C6A 117.47(17) . . ? F2A C2A C3A 119.17(19) . . ? F2A C2A C1A 119.17(17) . . ? C3A C2A C1A 121.63(19) . . ? F3A C3A C2A 119.7(2) . . ? F3A C3A C4A 120.2(2) . . ? C2A C3A C4A 120.1(2) . . ? F4A C4A C5A 120.3(2) . . ? F4A C4A C3A 120.4(2) . . ? C5A C4A C3A 119.36(18) . . ? F5A C5A C4A 119.7(2) . . ? F5A C5A C6A 120.1(2) . . ? C4A C5A C6A 120.22(19) . . ? F6A C6A C5A 119.62(18) . . ? F6A C6A C1A 119.17(18) . . ? C5A C6A C1A 121.21(19) . . ? C1 N1 C2 124.72(14) . . ? C1 N1 H1N 116.8 . . ? C2 N1 H1N 118.4 . . ? O1 C1 N1 126.54(17) . . ? O1 C1 C1 120.3(2) . 3_576 ? N1 C1 C1 113.19(19) . 3_576 ? C7 C2 C3 122.64(16) . . ? C7 C2 N1 118.76(16) . . ? C3 C2 N1 118.57(16) . . ? C4 C3 C2 117.21(17) . . ? C4 C3 C8 121.26(19) . . ? C2 C3 C8 121.52(18) . . ? C5 C4 C3 121.33(18) . . ? C5 C4 H4 122.3 . . ? C3 C4 H4 116.3 . . ? C4 C5 C6 120.35(17) . . ? C4 C5 H5 121.6 . . ? C6 C5 H5 118.1 . . ? C5 C6 C7 120.98(18) . . ? C5 C6 H6 118.8 . . ? C7 C6 H6 120.2 . . ? C2 C7 C6 117.46(17) . . ? C2 C7 C9 121.93(18) . . ? C6 C7 C9 120.61(19) . . ? C3 C8 H8A 109.8 . . ? C3 C8 H8C 109.9 . . ? H8A C8 H8C 108.3 . . ? C3 C8 H8B 109.0 . . ? H8A C8 H8B 109.9 . . ? H8C C8 H8B 109.9 . . ? C7 C9 H9A 109.4 . . ? C7 C9 H9C 110.0 . . ? H9A C9 H9C 108.2 . . ? C7 C9 H9B 109.7 . . ? H9A C9 H9B 109.8 . . ? H9C C9 H9B 109.8 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1A H1A O1 0.81 1.92 2.728(2) 176.8 1_545 N1 H1N O1A 0.82 2.42 3.163(2) 152.2 . N1 H1N O1 0.82 2.29 2.6783(19) 110.0 3_576 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.242 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.042 #===END data_4pfp _database_code_depnum_ccdc_archive 'CCDC 652029' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(3,5-dimethylphenyl)ethanediamide bis-2,3,4,5,6-pentafluorophenol ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N2 O2, 2(C6 H F5 O)' _chemical_formula_sum 'C30 H22 F10 N2 O4' _chemical_formula_weight 664.50 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' 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' N N 0.0061 0.0033 '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 7.0285(5) _cell_length_b 7.5525(5) _cell_length_c 13.6546(9) _cell_angle_alpha 91.511(5) _cell_angle_beta 101.938(6) _cell_angle_gamma 92.892(6) _cell_volume 707.74(8) _cell_formula_units_Z 1 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 4271 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 338 _exptl_absorpt_coefficient_mu 0.147 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 130(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 'KumaCCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% negligible _diffrn_reflns_number 7436 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.58 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2883 _reflns_number_gt 2393 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_cell_refinement ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_data_reduction ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'Stereochemical Workstation (Siemens Analytical X-Ray Instruments, Inc., 1989)' ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-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^)+(0.0620P)^2^+0.1966P] 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 refu _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.015(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2883 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1112 _refine_ls_wR_factor_gt 0.1065 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 O1 O -0.02035(17) 0.40420(14) 1.11353(8) 0.0298(3) Uani 1 1 d . . . N1 N 0.11224(17) 0.67557(15) 1.08501(9) 0.0211(3) Uani 1 1 d . . . H1N H 0.1339 0.7416 1.0341 0.031(5) Uiso 1 1 d R . . C1 C 0.0232(2) 0.51637(18) 1.05725(10) 0.0207(3) Uani 1 1 d . . . C2 C 0.17293(19) 0.75371(17) 1.18293(10) 0.0192(3) Uani 1 1 d . . . C3 C 0.24233(19) 0.93144(18) 1.18858(11) 0.0206(3) Uani 1 1 d . . . H3 H 0.2489 0.9879 1.1271 0.019(4) Uiso 1 1 d R . . C4 C 0.30267(19) 1.01909(18) 1.28148(11) 0.0225(3) Uani 1 1 d . . . C5 C 0.2937(2) 0.92662(19) 1.36746(11) 0.0237(3) Uani 1 1 d . . . H5 H 0.3335 0.9914 1.4305 0.026(4) Uiso 1 1 d R . . C6 C 0.2264(2) 0.74979(19) 1.36275(10) 0.0232(3) Uani 1 1 d . . . C7 C 0.1646(2) 0.66298(18) 1.26914(10) 0.0209(3) Uani 1 1 d . . . H7 H 0.1135 0.5423 1.2669 0.024(4) Uiso 1 1 d R . . C8 C 0.3751(2) 1.2110(2) 1.28849(13) 0.0318(4) Uani 1 1 d . . . H81 H 0.3209 1.2722 1.3379 0.070(7) Uiso 1 1 d R . . H82 H 0.3413 1.2724 1.2272 0.082(8) Uiso 1 1 d R . . H83 H 0.5124 1.2290 1.3152 0.062(7) Uiso 1 1 d R . . C9 C 0.2187(3) 0.6510(2) 1.45611(12) 0.0366(4) Uani 1 1 d . . . H91 H 0.1943 0.7239 1.5104 0.085(8) Uiso 1 1 d R . . H92 H 0.1295 0.5485 1.4458 0.080(8) Uiso 1 1 d R . . H93 H 0.3428 0.6067 1.4849 0.088(9) Uiso 1 1 d R . . O1A O 0.21081(17) 0.91276(15) 0.91877(8) 0.0348(3) Uani 1 1 d . . . H1O H 0.1620 0.8159 0.8886 0.075(8) Uiso 1 1 d R . . F2A F 0.36264(15) 1.23988(13) 0.98767(7) 0.0383(3) Uani 1 1 d . . . F3A F 0.43650(14) 1.49146(12) 0.86077(8) 0.0400(3) Uani 1 1 d . . . F4A F 0.34817(15) 1.42170(13) 0.65902(8) 0.0431(3) Uani 1 1 d . . . F5A F 0.19718(15) 1.09472(14) 0.58658(7) 0.0397(3) Uani 1 1 d . . . F6A F 0.12899(13) 0.84002(12) 0.71401(7) 0.0333(2) Uani 1 1 d . . . C1A C 0.2466(2) 1.03462(19) 0.85313(11) 0.0233(3) Uani 1 1 d . . . C2A C 0.3243(2) 1.2022(2) 0.88844(11) 0.0248(3) Uani 1 1 d . . . C3A C 0.3601(2) 1.33116(19) 0.82397(12) 0.0258(3) Uani 1 1 d . . . C4A C 0.3171(2) 1.2959(2) 0.72218(12) 0.0272(3) Uani 1 1 d . . . C5A C 0.2398(2) 1.1296(2) 0.68557(11) 0.0261(3) Uani 1 1 d . . . C6A C 0.2054(2) 1.00149(19) 0.75040(11) 0.0238(3) 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 O1 0.0432(6) 0.0241(5) 0.0207(5) 0.0004(4) 0.0060(5) -0.0095(5) N1 0.0273(6) 0.0187(6) 0.0171(6) 0.0005(5) 0.0044(5) -0.0014(5) C1 0.0216(7) 0.0207(7) 0.0198(7) -0.0011(5) 0.0046(5) 0.0013(5) C2 0.0180(6) 0.0197(7) 0.0193(7) -0.0026(5) 0.0028(5) 0.0021(5) C3 0.0179(6) 0.0202(7) 0.0231(7) 0.0022(5) 0.0029(5) 0.0012(5) C4 0.0169(6) 0.0202(7) 0.0292(8) -0.0025(6) 0.0026(5) 0.0017(5) C5 0.0204(7) 0.0268(7) 0.0225(7) -0.0052(6) 0.0016(5) 0.0030(6) C6 0.0223(7) 0.0269(7) 0.0206(7) 0.0018(6) 0.0039(5) 0.0039(6) C7 0.0213(7) 0.0190(6) 0.0223(7) 0.0011(5) 0.0042(5) 0.0019(5) C8 0.0337(9) 0.0212(7) 0.0374(9) -0.0032(7) 0.0020(7) -0.0027(6) C9 0.0501(10) 0.0368(9) 0.0221(8) 0.0035(7) 0.0059(7) -0.0005(8) O1A 0.0467(7) 0.0299(6) 0.0270(6) 0.0061(5) 0.0083(5) -0.0108(5) F2A 0.0440(6) 0.0424(6) 0.0247(5) -0.0075(4) 0.0018(4) -0.0081(4) F3A 0.0382(5) 0.0228(5) 0.0565(7) -0.0047(4) 0.0080(5) -0.0099(4) F4A 0.0467(6) 0.0392(6) 0.0466(6) 0.0213(5) 0.0147(5) 0.0009(5) F5A 0.0449(6) 0.0529(6) 0.0223(5) -0.0007(4) 0.0090(4) 0.0044(5) F6A 0.0366(5) 0.0258(5) 0.0362(5) -0.0097(4) 0.0075(4) -0.0051(4) C1A 0.0217(7) 0.0236(7) 0.0254(7) 0.0037(6) 0.0071(6) -0.0014(5) C2A 0.0221(7) 0.0287(8) 0.0228(7) -0.0034(6) 0.0038(6) -0.0014(6) C3A 0.0196(7) 0.0201(7) 0.0371(9) -0.0020(6) 0.0057(6) -0.0028(5) C4A 0.0238(7) 0.0267(8) 0.0340(8) 0.0113(6) 0.0107(6) 0.0031(6) C5A 0.0229(7) 0.0351(8) 0.0216(7) -0.0002(6) 0.0073(6) 0.0048(6) C6A 0.0213(7) 0.0218(7) 0.0284(8) -0.0055(6) 0.0067(6) -0.0012(5) _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 O1 C1 1.2279(18) . ? N1 C1 1.3351(18) . ? N1 C2 1.4195(17) . ? N1 H1N 0.9000 . ? C1 C1 1.540(3) 2_567 ? C2 C7 1.388(2) . ? C2 C3 1.3995(19) . ? C3 C4 1.390(2) . ? C3 H3 0.9600 . ? C4 C5 1.393(2) . ? C4 C8 1.5057(19) . ? C5 C6 1.389(2) . ? C5 H5 0.9600 . ? C6 C7 1.3963(19) . ? C6 C9 1.503(2) . ? C7 H7 0.9600 . ? C8 H81 0.9600 . ? C8 H82 0.9600 . ? C8 H83 0.9600 . ? C9 H91 0.9600 . ? C9 H92 0.9600 . ? C9 H93 0.9600 . ? O1A C1A 1.3518(18) . ? O1A H1O 0.8500 . ? F2A C2A 1.3456(17) . ? F3A C3A 1.3406(16) . ? F4A C4A 1.3395(17) . ? F5A C5A 1.3385(17) . ? F6A C6A 1.3469(16) . ? C1A C6A 1.386(2) . ? C1A C2A 1.386(2) . ? C2A C3A 1.378(2) . ? C3A C4A 1.376(2) . ? C4A C5A 1.381(2) . ? C5A C6A 1.374(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 C1 N1 C2 128.66(12) . . ? C1 N1 H1N 114.7 . . ? C2 N1 H1N 116.7 . . ? O1 C1 N1 126.06(13) . . ? O1 C1 C1 121.45(15) . 2_567 ? N1 C1 C1 112.49(15) . 2_567 ? C7 C2 C3 120.81(12) . . ? C7 C2 N1 123.22(12) . . ? C3 C2 N1 115.97(12) . . ? C4 C3 C2 119.82(13) . . ? C4 C3 H3 122.2 . . ? C2 C3 H3 118.0 . . ? C3 C4 C5 118.84(13) . . ? C3 C4 C8 120.32(14) . . ? C5 C4 C8 120.83(13) . . ? C6 C5 C4 121.82(13) . . ? C6 C5 H5 121.2 . . ? C4 C5 H5 117.0 . . ? C5 C6 C7 119.03(13) . . ? C5 C6 C9 121.34(13) . . ? C7 C6 C9 119.64(13) . . ? C2 C7 C6 119.68(13) . . ? C2 C7 H7 122.2 . . ? C6 C7 H7 118.1 . . ? C4 C8 H81 108.8 . . ? C4 C8 H82 114.5 . . ? H81 C8 H82 107.5 . . ? C4 C8 H83 113.5 . . ? H81 C8 H83 102.0 . . ? H82 C8 H83 109.6 . . ? C6 C9 H91 114.0 . . ? C6 C9 H92 114.3 . . ? H91 C9 H92 109.3 . . ? C6 C9 H93 111.5 . . ? H91 C9 H93 101.8 . . ? H92 C9 H93 104.9 . . ? C1A O1A H1O 111.1 . . ? O1A C1A C6A 122.93(13) . . ? O1A C1A C2A 119.51(13) . . ? C6A C1A C2A 117.55(14) . . ? F2A C2A C3A 119.53(13) . . ? F2A C2A C1A 119.10(14) . . ? C3A C2A C1A 121.36(14) . . ? F3A C3A C4A 120.06(14) . . ? F3A C3A C2A 119.76(14) . . ? C4A C3A C2A 120.18(13) . . ? F4A C4A C3A 120.48(14) . . ? F4A C4A C5A 120.22(14) . . ? C3A C4A C5A 119.30(14) . . ? F5A C5A C6A 120.30(14) . . ? F5A C5A C4A 119.55(14) . . ? C6A C5A C4A 120.15(14) . . ? F6A C6A C5A 119.74(13) . . ? F6A C6A C1A 118.79(13) . . ? C5A C6A C1A 121.46(13) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1A 0.90 2.20 3.0953(16) 174.8 . N1 H1N O1 0.90 2.24 2.6981(15) 110.7 2_567 O1A H1O O1 0.85 1.89 2.6634(16) 150.5 2_567 C7 H7 O1 0.96 2.31 2.8994(17) 119.1 . N1 H1N O1 0.90 2.24 2.6981(15) 110.7 2_567 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.240 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.047 #===END data_4pfba _database_code_depnum_ccdc_archive 'CCDC 652030' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(3,5-dimethylphenyl)ethanediamide bis-2,3,4,5,6-pentafluorobenzoic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C18 H20 N2 O2)0.5, C7 F5 O2 H' _chemical_formula_sum 'C16 H11 F5 N O3' _chemical_formula_weight 360.26 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' _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 6.9617(10) _cell_length_b 8.3110(11) _cell_length_c 13.3819(19) _cell_angle_alpha 91.559(15) _cell_angle_beta 104.416(11) _cell_angle_gamma 92.117(11) _cell_volume 748.84(18) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 4506 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.598 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 366 _exptl_absorpt_coefficient_mu 0.151 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 'KumaCCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% negligible _diffrn_reflns_number 5623 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.37 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2612 _reflns_number_gt 1998 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_cell_refinement ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_data_reduction ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2003 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'Stereochemical Workstation (Siemens Analytical X-Ray Instruments, Inc., 1989)' ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-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^)+(0.0787P)^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 2612 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1320 _refine_ls_wR_factor_gt 0.1244 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 O1A O 0.2961(2) 0.56884(17) 0.54907(11) 0.0300(4) Uani 1 1 d . . . O2A O 0.2568(3) 0.70244(17) 0.68885(11) 0.0361(4) Uani 1 1 d . . . H2O H 0.3062 0.7845 0.6613 0.072(10) Uiso 1 1 d R . . F2A F 0.11106(19) 0.27688(13) 0.52075(8) 0.0299(3) Uani 1 1 d . . . F3A F 0.02589(19) 0.00821(13) 0.60829(9) 0.0337(4) Uani 1 1 d . . . F4A F 0.0873(2) -0.00095(14) 0.81560(10) 0.0360(4) Uani 1 1 d . . . F5A F 0.2253(2) 0.26662(14) 0.93648(9) 0.0352(4) Uani 1 1 d . . . F6A F 0.3022(2) 0.53911(13) 0.85352(9) 0.0314(3) Uani 1 1 d . . . C1A C 0.2090(3) 0.4216(2) 0.68266(14) 0.0195(5) Uani 1 1 d . . . C2A C 0.1408(3) 0.2805(2) 0.62354(14) 0.0211(5) Uani 1 1 d . . . C3A C 0.0980(3) 0.1407(2) 0.66749(15) 0.0222(5) Uani 1 1 d . . . C4A C 0.1266(3) 0.1351(2) 0.77277(16) 0.0240(5) Uani 1 1 d . . . C5A C 0.1955(3) 0.2718(2) 0.83384(15) 0.0230(5) Uani 1 1 d . . . C6A C 0.2340(3) 0.4118(2) 0.78888(15) 0.0228(5) Uani 1 1 d . . . C7A C 0.2583(3) 0.5700(2) 0.63247(15) 0.0220(5) Uani 1 1 d . . . O1 O 0.5406(2) 1.07099(17) 0.38479(11) 0.0319(4) Uani 1 1 d . . . N1 N 0.4040(2) 0.83016(19) 0.41617(12) 0.0200(4) Uani 1 1 d . . . H1N H 0.3798 0.7751 0.4663 0.035(7) Uiso 1 1 d R . . C1 C 0.4870(3) 0.9766(2) 0.44262(15) 0.0215(5) Uani 1 1 d . . . C2 C 0.3530(3) 0.7536(2) 0.31543(14) 0.0194(5) Uani 1 1 d . . . C3 C 0.3027(3) 0.5891(2) 0.30885(15) 0.0199(5) Uani 1 1 d . . . H3 H 0.3073 0.5328 0.3660 0.022(5) Uiso 1 1 d R . . C4 C 0.2497(3) 0.5072(2) 0.21364(15) 0.0229(5) Uani 1 1 d . . . C5 C 0.2460(3) 0.5928(2) 0.12489(15) 0.0237(5) Uani 1 1 d . . . H5 H 0.2083 0.5347 0.0595 0.028(6) Uiso 1 1 d R . . C6 C 0.2921(3) 0.7569(2) 0.13030(15) 0.0236(5) Uani 1 1 d . . . C7 C 0.3472(3) 0.8379(2) 0.22671(15) 0.0214(5) Uani 1 1 d . . . H7 H 0.3794 0.9523 0.2284 0.029(6) Uiso 1 1 d R . . C8 C 0.1983(4) 0.3293(2) 0.20669(17) 0.0316(5) Uani 1 1 d . . . H8A H 0.2526 0.2818 0.2717 0.038 Uiso 1 1 d R . . H8B H 0.2497 0.2804 0.1535 0.038 Uiso 1 1 d R . . H8C H 0.0565 0.3129 0.1870 0.038 Uiso 1 1 d R . . C9 C 0.2807(4) 0.8490(3) 0.03394(16) 0.0350(6) Uani 1 1 d . . . H9A H 0.3322 0.7886 -0.0150 0.042 Uiso 1 1 d R . . H9C H 0.3540 0.9501 0.0529 0.042 Uiso 1 1 d R . . H9D H 0.1445 0.8724 0.0052 0.042 Uiso 1 1 d 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 O1A 0.0461(10) 0.0254(8) 0.0213(8) 0.0042(6) 0.0137(7) -0.0004(7) O2A 0.0624(12) 0.0177(8) 0.0361(9) 0.0002(7) 0.0278(8) -0.0030(7) F2A 0.0448(8) 0.0270(7) 0.0164(6) -0.0011(5) 0.0052(6) -0.0010(6) F3A 0.0461(9) 0.0198(7) 0.0318(7) -0.0041(5) 0.0050(6) -0.0047(6) F4A 0.0514(9) 0.0202(6) 0.0376(7) 0.0106(5) 0.0129(6) -0.0025(6) F5A 0.0563(9) 0.0320(7) 0.0187(6) 0.0060(5) 0.0116(6) 0.0034(6) F6A 0.0503(8) 0.0216(6) 0.0216(6) -0.0060(5) 0.0088(6) -0.0035(6) C1A 0.0235(11) 0.0173(10) 0.0190(10) 0.0011(8) 0.0072(8) 0.0032(8) C2A 0.0246(11) 0.0229(11) 0.0160(10) -0.0001(8) 0.0052(8) 0.0034(9) C3A 0.0253(12) 0.0153(10) 0.0253(11) -0.0030(8) 0.0054(9) -0.0012(8) C4A 0.0284(12) 0.0167(10) 0.0278(11) 0.0069(8) 0.0084(9) 0.0017(9) C5A 0.0285(12) 0.0256(11) 0.0165(10) 0.0044(8) 0.0081(9) 0.0033(9) C6A 0.0298(12) 0.0170(10) 0.0221(11) -0.0037(8) 0.0081(9) 0.0020(9) C7A 0.0252(12) 0.0179(10) 0.0232(11) 0.0003(8) 0.0063(9) 0.0020(8) O1 0.0498(11) 0.0237(8) 0.0223(8) -0.0008(6) 0.0113(7) -0.0122(7) N1 0.0286(10) 0.0165(8) 0.0150(8) 0.0011(7) 0.0061(7) -0.0011(7) C1 0.0261(12) 0.0176(10) 0.0213(11) -0.0001(8) 0.0068(9) 0.0011(9) C2 0.0215(11) 0.0191(10) 0.0179(10) -0.0014(8) 0.0059(8) 0.0009(8) C3 0.0240(11) 0.0180(10) 0.0178(10) 0.0040(8) 0.0049(8) 0.0006(8) C4 0.0236(11) 0.0200(10) 0.0250(11) -0.0032(8) 0.0062(9) 0.0003(8) C5 0.0269(12) 0.0241(11) 0.0193(11) -0.0033(8) 0.0050(9) -0.0005(9) C6 0.0267(12) 0.0239(11) 0.0208(11) -0.0004(8) 0.0069(9) 0.0008(9) C7 0.0272(12) 0.0164(10) 0.0200(10) 0.0016(8) 0.0050(9) 0.0004(8) C8 0.0419(14) 0.0212(11) 0.0304(12) -0.0031(9) 0.0076(10) -0.0042(10) C9 0.0514(16) 0.0322(13) 0.0210(11) 0.0017(9) 0.0091(11) -0.0044(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 O1A C7A 1.209(2) . ? O2A C7A 1.320(2) . ? O2A H2O 0.8828 . ? F2A C2A 1.338(2) . ? F3A C3A 1.344(2) . ? F4A C4A 1.332(2) . ? F5A C5A 1.339(2) . ? F6A C6A 1.342(2) . ? C1A C2A 1.396(3) . ? C1A C6A 1.394(3) . ? C1A C7A 1.489(3) . ? C2A C3A 1.373(3) . ? C3A C4A 1.375(3) . ? C4A C5A 1.379(3) . ? C5A C6A 1.372(3) . ? O1 C1 1.228(3) . ? N1 C1 1.328(3) . ? N1 C2 1.431(2) . ? N1 H1N 0.8689 . ? C1 C1 1.539(4) 2_676 ? C2 C7 1.387(3) . ? C2 C3 1.394(3) . ? C3 C4 1.387(3) . ? C3 H3 0.9013 . ? C4 C5 1.396(3) . ? C4 C8 1.503(3) . ? C5 C6 1.385(3) . ? C5 H5 0.9600 . ? C6 C7 1.397(3) . ? C6 C9 1.504(3) . ? C7 H7 0.9674 . ? C8 H8A 0.9599 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9C 0.9600 . ? C9 H9D 0.9600 . ? 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 C7A O2A H2O 109.4 . . ? C2A C1A C6A 116.22(18) . . ? C2A C1A C7A 120.27(17) . . ? C6A C1A C7A 123.47(18) . . ? F2A C2A C3A 117.06(17) . . ? F2A C2A C1A 121.10(18) . . ? C3A C2A C1A 121.83(18) . . ? F3A C3A C2A 120.53(18) . . ? F3A C3A C4A 119.20(18) . . ? C2A C3A C4A 120.27(18) . . ? F4A C4A C3A 120.33(18) . . ? F4A C4A C5A 120.11(19) . . ? C3A C4A C5A 119.56(19) . . ? F5A C5A C6A 120.56(18) . . ? F5A C5A C4A 119.78(18) . . ? C6A C5A C4A 119.66(18) . . ? F6A C6A C5A 116.10(17) . . ? F6A C6A C1A 121.44(18) . . ? C5A C6A C1A 122.44(18) . . ? O1A C7A O2A 123.68(19) . . ? O1A C7A C1A 123.50(18) . . ? O2A C7A C1A 112.82(17) . . ? C1 N1 C2 127.30(17) . . ? C1 N1 H1N 115.6 . . ? C2 N1 H1N 117.1 . . ? O1 C1 N1 126.05(18) . . ? O1 C1 C1 120.5(2) . 2_676 ? N1 C1 C1 113.5(2) . 2_676 ? C7 C2 C3 120.40(17) . . ? C7 C2 N1 122.43(17) . . ? C3 C2 N1 117.15(17) . . ? C4 C3 C2 120.34(18) . . ? C4 C3 H3 118.4 . . ? C2 C3 H3 121.2 . . ? C3 C4 C5 118.83(18) . . ? C3 C4 C8 120.33(18) . . ? C5 C4 C8 120.84(17) . . ? C6 C5 C4 121.36(18) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 117.9 . . ? C5 C6 C7 119.33(18) . . ? C5 C6 C9 120.95(17) . . ? C7 C6 C9 119.72(18) . . ? C2 C7 C6 119.73(18) . . ? C2 C7 H7 122.6 . . ? C6 C7 H7 117.7 . . ? C4 C8 H8A 110.4 . . ? C4 C8 H8B 108.9 . . ? H8A C8 H8B 110.5 . . ? C4 C8 H8C 108.8 . . ? H8A C8 H8C 110.5 . . ? H8B C8 H8C 107.7 . . ? C6 C9 H9A 111.0 . . ? C6 C9 H9C 108.4 . . ? H9A C9 H9C 110.9 . . ? C6 C9 H9D 108.1 . . ? H9A C9 H9D 110.9 . . ? H9C C9 H9D 107.4 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2A H2O O1 0.88 1.80 2.665(2) 166.9 2_676 N1 H1N O1A 0.87 2.20 3.033(2) 159.5 . C7 H7 O1 0.97 2.29 2.865(2) 117.1 . N1 H1N O1 0.87 2.27 2.695(2) 109.8 2_676 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.250 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.066 #===END