# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address 'Susanta K. Nayak' ; Solid State and Structural Chemistry Unit Indian Institute of Science Bangalore 560 012, Karnataka India ; 'M. Kishore Reddy' ; Solid State and Structural Chemistry Unit Indian Institute of Science Bangalore 560 012, Karnataka India ; 'Deepak Chopra' ; Department of Chemistry Indian Institute of Science Education and Research ITI (Gas Rahat Building) Govindpura, Bhopal-462023 India ; 'T. N. Guru Row' ; Solid State and Structural Chemistry Unit Indian Institute of Science Bangalore 560 012, Karnataka India ; _publ_contact_author_name 'Dr Deepak Chopra' _publ_contact_author_email dchopra@iiserbhopal.ac.in _publ_section_title ; Evaluation of the Role of Disordered Organic Fluorine in Crystal Packing: Insights from halogen substituted Benzanilides. ; #============================================================================= data_2FB-2BrA _database_code_depnum_ccdc_archive 'CCDC 640039' #TrackingRef '- CIF.cif' #========================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-fluoro-N-(2-bromophenyl) benzamide ; _chemical_name_common '2-fluoro-N-(2-bromophenyl) benzamide' _chemical_formula_sum 'C13 H9 Br F N O' _chemical_formula_weight 294.12 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.2187(18) _cell_length_b 4.7411(7) _cell_length_c 21.685(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.910(2) _cell_angle_gamma 90.00 _cell_volume 1150.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 615 _cell_measurement_theta_min 0.9659 _cell_measurement_theta_max 27.9932 _exptl_crystal_description ' plate' _exptl_crystal_colour ' colorless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 3.566 _exptl_absorpt_correction_T_min 0.4143 _exptl_absorpt_correction_T_max 0.6951 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8146 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.67 _reflns_number_total 2179 _reflns_number_gt 1830 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART V5.628, (Bruker, 2004)' _computing_cell_refinement 'Bruker SMART V5.628, (Bruker, 2004)' _computing_data_reduction 'Bruker SAINT V6.45a, (Bruker, 2004)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND. version 2.1c (Brandenburg, K. 1999)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0355P)^2^+0.5222P] 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 2179 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0725 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 C1A C 0.0349(2) -0.0060(5) 0.18919(11) 0.0390(6) Uani 0.835(5) 1 d P A -1 C2A C 0.0958(2) 0.1883(6) 0.22685(12) 0.0475(6) Uani 0.835(5) 1 d P A -1 C3A C 0.0530(3) 0.2835(7) 0.28115(13) 0.0616(8) Uani 0.835(5) 1 d P A -1 H3A H 0.0960 0.4148 0.3056 0.074 Uiso 0.835(5) 1 calc PR A -1 C4A C -0.0538(3) 0.1815(7) 0.29858(14) 0.0653(9) Uani 0.835(5) 1 d P A -1 H4A H -0.0839 0.2443 0.3351 0.078 Uiso 0.835(5) 1 calc PR A -1 C5A C -0.1166(3) -0.0123(7) 0.26260(14) 0.0610(8) Uani 0.835(5) 1 d P A -1 H5A H -0.1894 -0.0802 0.2745 0.073 Uiso 0.835(5) 1 calc PR A -1 C6A C -0.0723(2) -0.1056(6) 0.20916(13) 0.0504(7) Uani 0.835(5) 1 d P A -1 H6A H -0.1151 -0.2396 0.1855 0.061 Uiso 0.835(5) 1 calc PR A -1 F1A F 0.20236(19) 0.2872(5) 0.21177(10) 0.0673(8) Uani 0.835(5) 1 d P A -1 C1B C 0.0349(2) -0.0060(5) 0.18919(11) 0.0390(6) Uani 0.165(5) 1 d P A -2 C2B C -0.0723(2) -0.1056(6) 0.20916(13) 0.0504(7) Uani 0.165(5) 1 d P A -2 C3B C -0.1166(3) -0.0123(7) 0.26260(14) 0.0610(8) Uani 0.165(5) 1 d P A -2 H3B H -0.1894 -0.0802 0.2745 0.073 Uiso 0.165(5) 1 calc PR A -2 C4B C -0.0538(3) 0.1815(7) 0.29858(14) 0.0653(9) Uani 0.165(5) 1 d P A -2 H4B H -0.0839 0.2443 0.3351 0.078 Uiso 0.165(5) 1 calc PR A -2 C5B C 0.0530(3) 0.2835(7) 0.28115(13) 0.0616(8) Uani 0.165(5) 1 d P A -2 H5B H 0.0960 0.4148 0.3056 0.074 Uiso 0.165(5) 1 calc PR A -2 C6B C 0.0958(2) 0.1883(6) 0.22685(12) 0.0475(6) Uani 0.165(5) 1 d P A -2 H6B H 0.1684 0.2575 0.2151 0.057 Uiso 0.165(5) 1 calc PR A -2 F1B F -0.1385(9) -0.286(2) 0.1760(5) 0.071(4) Uani 0.165(5) 1 d P A -2 Br1 Br 0.37709(2) 0.36077(6) 0.082893(13) 0.05451(13) Uani 1 1 d . . . O1 O 0.05745(19) -0.3664(4) 0.11566(9) 0.0591(5) Uani 1 1 d . A . N1 N 0.13923(10) 0.0564(2) 0.09611(5) 0.0411(5) Uani 1 1 d . A . H1 H 0.1488 0.2256 0.1099 0.049 Uiso 1 1 calc R . . C7 C 0.07883(10) -0.1224(2) 0.13033(5) 0.0397(6) Uani 1 1 d R . . C8 C 0.18860(10) -0.0076(2) 0.03950(5) 0.0365(5) Uani 1 1 d R . . C9 C 0.29553(10) 0.1178(2) 0.02476(5) 0.0404(6) Uani 1 1 d R A . C10 C 0.34466(10) 0.0649(2) -0.03037(5) 0.0519(7) Uani 1 1 d R . . H10 H 0.4153 0.1532 -0.0397 0.062 Uiso 1 1 calc R . . C11 C 0.2883(3) -0.1200(7) -0.07176(13) 0.0583(8) Uani 1 1 d . A . H11 H 0.3219 -0.1597 -0.1088 0.070 Uiso 1 1 calc R . . C12 C 0.1832(3) -0.2457(6) -0.05864(13) 0.0544(7) Uani 1 1 d . . . H12 H 0.1455 -0.3692 -0.0870 0.065 Uiso 1 1 calc R A . C13 C 0.1325(2) -0.1905(5) -0.00349(12) 0.0445(6) Uani 1 1 d . A . H13 H 0.0608 -0.2759 0.0049 0.053 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 C1A 0.0432(13) 0.0318(13) 0.0420(14) 0.0026(11) 0.0020(11) 0.0050(11) C2A 0.0525(16) 0.0447(16) 0.0449(15) 0.0007(12) -0.0007(12) 0.0000(12) C3A 0.083(2) 0.0578(19) 0.0431(16) -0.0080(14) -0.0051(15) 0.0065(17) C4A 0.091(2) 0.065(2) 0.0419(16) 0.0006(15) 0.0157(16) 0.0266(19) C5A 0.0613(18) 0.071(2) 0.0534(18) 0.0069(16) 0.0200(15) 0.0091(17) C6A 0.0514(15) 0.0482(17) 0.0522(16) 0.0023(13) 0.0071(13) -0.0014(13) F1A 0.0631(14) 0.0777(16) 0.0604(13) -0.0120(11) 0.0002(10) -0.0223(11) C1B 0.0432(13) 0.0318(13) 0.0420(14) 0.0026(11) 0.0020(11) 0.0050(11) C2B 0.0514(15) 0.0482(17) 0.0522(16) 0.0023(13) 0.0071(13) -0.0014(13) C3B 0.0613(18) 0.071(2) 0.0534(18) 0.0069(16) 0.0200(15) 0.0091(17) C4B 0.091(2) 0.065(2) 0.0419(16) 0.0006(15) 0.0157(16) 0.0266(19) C5B 0.083(2) 0.0578(19) 0.0431(16) -0.0080(14) -0.0051(15) 0.0065(17) C6B 0.0525(16) 0.0447(16) 0.0449(15) 0.0007(12) -0.0007(12) 0.0000(12) F1B 0.065(7) 0.085(9) 0.064(7) -0.019(6) 0.024(6) -0.034(6) Br1 0.04963(18) 0.05457(19) 0.0587(2) -0.00344(14) -0.00053(12) -0.01442(13) O1 0.0842(15) 0.0317(10) 0.0641(12) -0.0061(9) 0.0241(11) -0.0078(10) N1 0.0472(12) 0.0297(10) 0.0472(12) -0.0068(9) 0.0102(10) -0.0060(9) C7 0.0419(13) 0.0299(13) 0.0475(14) -0.0006(11) 0.0042(11) 0.0019(11) C8 0.0380(13) 0.0300(12) 0.0418(14) 0.0009(10) 0.0045(11) 0.0033(10) C9 0.0416(13) 0.0352(14) 0.0439(14) 0.0032(11) 0.0002(11) 0.0000(11) C10 0.0499(15) 0.0593(18) 0.0475(16) 0.0056(13) 0.0099(13) -0.0049(13) C11 0.0670(19) 0.070(2) 0.0394(15) -0.0018(14) 0.0131(14) 0.0035(16) C12 0.0650(19) 0.0533(16) 0.0441(16) -0.0101(13) -0.0015(14) 0.0008(14) C13 0.0446(14) 0.0387(15) 0.0500(16) -0.0054(11) 0.0024(12) -0.0030(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A C2A 1.380(4) . ? C1A C6A 1.389(4) . ? C1A C7 1.504(3) . ? C2A F1A 1.345(3) . ? C2A C3A 1.378(4) . ? C3A C4A 1.369(5) . ? C3A H3A 0.9300 . ? C4A C5A 1.369(5) . ? C4A H4A 0.9300 . ? C5A C6A 1.366(4) . ? C5A H5A 0.9300 . ? C6A H6A 0.9300 . ? Br1 C9 1.8963(11) . ? O1 C7 1.220(2) . ? N1 C7 1.3406 . ? N1 C8 1.4137 . ? N1 H1 0.8600 . ? C8 C13 1.391(3) . ? C8 C9 1.3954 . ? C9 C10 1.3733 . ? C10 C11 1.377(3) . ? C10 H10 0.9300 . ? C11 C12 1.369(4) . ? C11 H11 0.9300 . ? C12 C13 1.383(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? 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 C2A C1A C6A 116.5(2) . . ? C2A C1A C7 124.7(2) . . ? C6A C1A C7 118.7(2) . . ? F1A C2A C3A 117.4(3) . . ? F1A C2A C1A 120.1(2) . . ? C3A C2A C1A 122.5(3) . . ? C4A C3A C2A 118.9(3) . . ? C4A C3A H3A 120.6 . . ? C2A C3A H3A 120.6 . . ? C5A C4A C3A 120.4(3) . . ? C5A C4A H4A 119.8 . . ? C3A C4A H4A 119.8 . . ? C6A C5A C4A 119.9(3) . . ? C6A C5A H5A 120.1 . . ? C4A C5A H5A 120.1 . . ? C5A C6A C1A 121.9(3) . . ? C5A C6A H6A 119.1 . . ? C1A C6A H6A 119.1 . . ? C7 N1 C8 126.0 . . ? C7 N1 H1 117.0 . . ? C8 N1 H1 117.0 . . ? O1 C7 N1 123.59(11) . . ? O1 C7 C1A 119.97(16) . . ? N1 C7 C1A 116.43(10) . . ? C13 C8 C9 117.93(12) . . ? C13 C8 N1 121.98(12) . . ? C9 C8 N1 120.1 . . ? C10 C9 C8 121.6 . . ? C10 C9 Br1 119.0 . . ? C8 C9 Br1 119.3 . . ? C9 C10 C11 119.34(13) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C12 C11 C10 120.4(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 120.5(3) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 120.2(2) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A C1A C2A F1A 177.7(2) . . . . ? C7 C1A C2A F1A 0.1(4) . . . . ? C6A C1A C2A C3A -0.8(4) . . . . ? C7 C1A C2A C3A -178.4(2) . . . . ? F1A C2A C3A C4A -178.4(3) . . . . ? C1A C2A C3A C4A 0.1(4) . . . . ? C2A C3A C4A C5A 0.2(5) . . . . ? C3A C4A C5A C6A 0.3(5) . . . . ? C4A C5A C6A C1A -1.1(5) . . . . ? C2A C1A C6A C5A 1.3(4) . . . . ? C7 C1A C6A C5A 179.0(2) . . . . ? C8 N1 C7 O1 -1.16(14) . . . . ? C8 N1 C7 C1A 179.83(11) . . . . ? C2A C1A C7 O1 145.0(2) . . . . ? C6A C1A C7 O1 -32.5(3) . . . . ? C2A C1A C7 N1 -35.9(3) . . . . ? C6A C1A C7 N1 146.53(18) . . . . ? C7 N1 C8 C13 35.78(13) . . . . ? C7 N1 C8 C9 -145.4 . . . . ? C13 C8 C9 C10 0.23(13) . . . . ? N1 C8 C9 C10 -178.6 . . . . ? C13 C8 C9 Br1 -178.37(15) . . . . ? N1 C8 C9 Br1 2.80(4) . . . . ? C8 C9 C10 C11 -1.16(15) . . . . ? Br1 C9 C10 C11 177.45(17) . . . . ? C9 C10 C11 C12 1.3(3) . . . . ? C10 C11 C12 C13 -0.5(4) . . . . ? C11 C12 C13 C8 -0.5(4) . . . . ? C9 C8 C13 C12 0.6(3) . . . . ? N1 C8 C13 C12 179.38(19) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.576 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.057 #============================================================================== data_3FB-4BrA _database_code_depnum_ccdc_archive 'CCDC 640042' #TrackingRef '- CIF.cif' #============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-fluoro-N-(4-bromophenyl) benzamide ; _chemical_name_common '3-fluoro-N-(4-bromophenyl) benzamide' _chemical_formula_sum 'C13 H9 Br F N O' _chemical_formula_weight 294.12 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 2/c' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.081(3) _cell_length_b 5.2349(7) _cell_length_c 17.549(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.716(2) _cell_angle_gamma 90.00 _cell_volume 2327.6(5) _cell_formula_units_Z 8 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 605 _cell_measurement_theta_min 0.9747 _cell_measurement_theta_max 27.9932 _exptl_crystal_description ' plate' _exptl_crystal_colour ' colour less' _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 3.526 _exptl_absorpt_correction_T_min 0.4279 _exptl_absorpt_correction_T_max 0.7420 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 8426 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.67 _reflns_number_total 2220 _reflns_number_gt 1769 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART V5.628, (Bruker, 2004)' _computing_cell_refinement 'Bruker SMART V5.628, (Bruker, 2004)' _computing_data_reduction 'Bruker SAINT V6.45a, (Bruker, 2004)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND. version 2.1c (Brandenburg, K. 1999)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+2.8843P] 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 2220 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0846 _refine_ls_wR_factor_gt 0.0769 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 F1A F 0.48185(12) 1.3139(7) 1.0388(2) 0.0813(14) Uani 0.614(5) 1 d P A -1 C1A C 0.36987(10) 0.8984(5) 1.01322(15) 0.0373(6) Uani 0.614(5) 1 d P A -1 C2A C 0.40128(12) 1.1002(5) 1.00148(18) 0.0479(7) Uani 0.614(5) 1 d P A -1 H2A H 0.3896 1.2140 0.9603 0.058 Uiso 0.614(5) 1 calc PR A -1 C3A C 0.45008(12) 1.1300(6) 1.0516(2) 0.0597(9) Uani 0.614(5) 1 d P A -1 C4A C 0.46842(13) 0.9708(7) 1.1143(2) 0.0626(9) Uani 0.614(5) 1 d P A -1 H4A H 0.5014 0.9956 1.1479 0.075 Uiso 0.614(5) 1 calc PR A -1 C5A C 0.43650(13) 0.7742(7) 1.12563(19) 0.0592(8) Uani 0.614(5) 1 d P A -1 H5A H 0.4479 0.6653 1.1681 0.071 Uiso 0.614(5) 1 calc PR A -1 C6A C 0.38803(11) 0.7339(6) 1.07577(17) 0.0463(7) Uani 0.614(5) 1 d P A -1 H6A H 0.3674 0.5964 1.0839 0.056 Uiso 0.614(5) 1 calc PR A -1 F1B F 0.4563(2) 0.6215(13) 1.1830(3) 0.097(3) Uani 0.386(5) 1 d P A -2 C1B C 0.36987(10) 0.8984(5) 1.01322(15) 0.0373(6) Uani 0.386(5) 1 d P A -2 C2B C 0.38803(11) 0.7339(6) 1.07577(17) 0.0463(7) Uani 0.386(5) 1 d P A -2 H2B H 0.3674 0.5964 1.0839 0.056 Uiso 0.386(5) 1 calc PR A -2 C3B C 0.43650(13) 0.7742(7) 1.12563(19) 0.0592(8) Uani 0.386(5) 1 d P A -2 C4B C 0.46842(13) 0.9708(7) 1.1143(2) 0.0626(9) Uani 0.386(5) 1 d P A -2 H4B H 0.5014 0.9956 1.1479 0.075 Uiso 0.386(5) 1 calc PR A -2 C5B C 0.45008(12) 1.1300(6) 1.0516(2) 0.0597(9) Uani 0.386(5) 1 d P A -2 H5B H 0.4715 1.2633 1.0427 0.072 Uiso 0.386(5) 1 calc PR A -2 C6B C 0.40128(12) 1.1002(5) 1.00148(18) 0.0479(7) Uani 0.386(5) 1 d P A -2 H6B H 0.3896 1.2140 0.9603 0.058 Uiso 0.386(5) 1 calc PR A -2 Br1 Br 0.086643(13) 1.07781(8) 0.67028(2) 0.06770(17) Uani 1 1 d . . . N1 N 0.29024(8) 1.0484(4) 0.92400(13) 0.0378(5) Uani 1 1 d . A . H1 H 0.3037 1.1963 0.9376 0.045 Uiso 1 1 calc R . . O1 O 0.30119(8) 0.6233(3) 0.94764(12) 0.0510(5) Uani 1 1 d . A . C7 C 0.31754(10) 0.8422(5) 0.95928(15) 0.0364(6) Uani 1 1 d . . . C8 C 0.24178(10) 1.0427(5) 0.86700(15) 0.0333(6) Uani 1 1 d . . . C9 C 0.20642(10) 1.2413(5) 0.86493(16) 0.0387(6) Uani 1 1 d . A . H9 H 0.2140 1.3691 0.9027 0.046 Uiso 1 1 calc R . . C10 C 0.16007(10) 1.2514(5) 0.80733(16) 0.0416(6) Uani 1 1 d . . . H10 H 0.1364 1.3850 0.8063 0.050 Uiso 1 1 calc R A . C11 C 0.14927(10) 1.0609(5) 0.75129(16) 0.0399(6) Uani 1 1 d . A . C12 C 0.18385(11) 0.8621(5) 0.75294(16) 0.0395(6) Uani 1 1 d . . . H12 H 0.1761 0.7341 0.7152 0.047 Uiso 1 1 calc R A . C13 C 0.23014(11) 0.8522(5) 0.81051(15) 0.0373(6) Uani 1 1 d . A . H13 H 0.2536 0.7177 0.8115 0.045 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 F1A 0.0502(19) 0.081(2) 0.103(3) 0.015(2) -0.0008(17) -0.0319(17) C1A 0.0361(14) 0.0332(13) 0.0404(14) -0.0047(12) 0.0049(11) 0.0006(11) C2A 0.0436(16) 0.0405(16) 0.0564(18) 0.0044(14) 0.0053(14) -0.0071(13) C3A 0.0413(17) 0.0549(19) 0.080(2) -0.0031(18) 0.0075(16) -0.0145(15) C4A 0.0417(17) 0.064(2) 0.071(2) -0.0077(18) -0.0089(16) -0.0022(16) C5A 0.0527(19) 0.061(2) 0.056(2) 0.0073(17) -0.0039(15) 0.0053(16) C6A 0.0422(16) 0.0414(16) 0.0511(17) 0.0054(13) 0.0025(13) -0.0023(13) F1B 0.063(4) 0.130(5) 0.080(4) 0.047(4) -0.019(3) -0.007(3) C1B 0.0361(14) 0.0332(13) 0.0404(14) -0.0047(12) 0.0049(11) 0.0006(11) C2B 0.0422(16) 0.0414(16) 0.0511(17) 0.0054(13) 0.0025(13) -0.0023(13) C3B 0.0527(19) 0.061(2) 0.056(2) 0.0073(17) -0.0039(15) 0.0053(16) C4B 0.0417(17) 0.064(2) 0.071(2) -0.0077(18) -0.0089(16) -0.0022(16) C5B 0.0413(17) 0.0549(19) 0.080(2) -0.0031(18) 0.0075(16) -0.0145(15) C6B 0.0436(16) 0.0405(16) 0.0564(18) 0.0044(14) 0.0053(14) -0.0071(13) Br1 0.0481(2) 0.0825(3) 0.0604(2) -0.00533(18) -0.01113(15) 0.01412(17) N1 0.0382(12) 0.0259(11) 0.0441(13) -0.0035(9) -0.0004(10) -0.0049(9) O1 0.0513(12) 0.0291(10) 0.0613(13) 0.0029(9) -0.0088(10) -0.0060(8) C7 0.0400(14) 0.0303(14) 0.0382(14) -0.0024(11) 0.0076(12) -0.0054(11) C8 0.0352(13) 0.0272(12) 0.0363(14) 0.0017(11) 0.0062(11) -0.0043(10) C9 0.0414(15) 0.0275(13) 0.0473(16) -0.0060(12) 0.0108(12) -0.0032(11) C10 0.0376(14) 0.0343(14) 0.0540(17) 0.0004(13) 0.0133(13) 0.0035(12) C11 0.0339(14) 0.0424(15) 0.0403(15) 0.0043(12) 0.0026(11) -0.0024(12) C12 0.0437(15) 0.0360(14) 0.0362(14) -0.0030(12) 0.0045(12) -0.0007(12) C13 0.0413(15) 0.0293(13) 0.0396(15) -0.0002(11) 0.0062(12) 0.0041(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1A C3A 1.324(4) . ? C1A C2A 1.382(4) . ? C1A C6A 1.387(4) . ? C1A C7 1.494(3) . ? C2A C3A 1.374(4) . ? C2A H2A 0.9300 . ? C3A C4A 1.373(5) . ? C4A C5A 1.367(5) . ? C4A H4A 0.9300 . ? C5A C6A 1.372(4) . ? C5A H5A 0.9300 . ? C6A H6A 0.9300 . ? Br1 C11 1.896(3) . ? N1 C7 1.359(3) . ? N1 C8 1.414(3) . ? N1 H1 0.8600 . ? O1 C7 1.223(3) . ? C8 C9 1.385(4) . ? C8 C13 1.388(4) . ? C9 C10 1.381(4) . ? C9 H9 0.9300 . ? C10 C11 1.382(4) . ? C10 H10 0.9300 . ? C11 C12 1.373(4) . ? C12 C13 1.379(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? 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 C2A C1A C6A 119.3(3) . . ? C2A C1A C7 122.7(2) . . ? C6A C1A C7 117.9(2) . . ? C3A C2A C1A 118.9(3) . . ? C3A C2A H2A 120.5 . . ? C1A C2A H2A 120.5 . . ? F1A C3A C4A 117.7(3) . . ? F1A C3A C2A 119.7(3) . . ? C4A C3A C2A 122.5(3) . . ? C5A C4A C3A 117.7(3) . . ? C5A C4A H4A 121.1 . . ? C3A C4A H4A 121.1 . . ? C4A C5A C6A 121.6(3) . . ? C4A C5A H5A 119.2 . . ? C6A C5A H5A 119.2 . . ? C5A C6A C1A 119.9(3) . . ? C5A C6A H6A 120.0 . . ? C1A C6A H6A 120.0 . . ? C7 N1 C8 126.1(2) . . ? C7 N1 H1 116.9 . . ? C8 N1 H1 116.9 . . ? O1 C7 N1 123.0(2) . . ? O1 C7 C1A 121.3(2) . . ? N1 C7 C1A 115.7(2) . . ? C9 C8 C13 119.3(2) . . ? C9 C8 N1 118.7(2) . . ? C13 C8 N1 121.9(2) . . ? C10 C9 C8 120.7(2) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 119.2(3) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C12 C11 C10 120.7(2) . . ? C12 C11 Br1 119.7(2) . . ? C10 C11 Br1 119.6(2) . . ? C11 C12 C13 120.0(2) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C8 120.1(2) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 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 C6A C1A C2A C3A 0.9(4) . . . . ? C7 C1A C2A C3A -176.6(3) . . . . ? C1A C2A C3A F1A 176.4(3) . . . . ? C1A C2A C3A C4A -1.7(5) . . . . ? F1A C3A C4A C5A -177.3(4) . . . . ? C2A C3A C4A C5A 0.8(6) . . . . ? C3A C4A C5A C6A 0.9(5) . . . . ? C4A C5A C6A C1A -1.6(5) . . . . ? C2A C1A C6A C5A 0.7(4) . . . . ? C7 C1A C6A C5A 178.3(3) . . . . ? C8 N1 C7 O1 -3.7(4) . . . . ? C8 N1 C7 C1A 175.5(2) . . . . ? C2A C1A C7 O1 147.5(3) . . . . ? C6A C1A C7 O1 -30.1(4) . . . . ? C2A C1A C7 N1 -31.7(4) . . . . ? C6A C1A C7 N1 150.7(3) . . . . ? C7 N1 C8 C9 147.7(3) . . . . ? C7 N1 C8 C13 -36.1(4) . . . . ? C13 C8 C9 C10 -0.2(4) . . . . ? N1 C8 C9 C10 176.1(2) . . . . ? C8 C9 C10 C11 -0.2(4) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? C9 C10 C11 Br1 -178.3(2) . . . . ? C10 C11 C12 C13 -0.6(4) . . . . ? Br1 C11 C12 C13 178.3(2) . . . . ? C11 C12 C13 C8 0.2(4) . . . . ? C9 C8 C13 C12 0.2(4) . . . . ? N1 C8 C13 C12 -175.9(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.415 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.057 #END #============================================================================== data_3FA-2BrB _database_code_depnum_ccdc_archive 'CCDC 764625' #TrackingRef '- CIF.cif' #============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-bromo-N-(3-fluoro)benzamide ; _chemical_name_common 2-bromo-N-(3-fluoro)benzamide _chemical_formula_sum 'C13 H9 Br F N O' _chemical_formula_weight 294.12 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.0904(11) _cell_length_b 10.696(2) _cell_length_c 12.054(3) _cell_angle_alpha 113.637(3) _cell_angle_beta 97.827(3) _cell_angle_gamma 93.133(3) _cell_volume 591.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 330 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 0.97 _exptl_crystal_description Plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.652 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 3.470 _exptl_absorpt_correction_T_min 0.4897 _exptl_absorpt_correction_T_max 0.6067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6023 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.68 _reflns_number_total 2239 _reflns_number_gt 1904 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction SAINT _computing_structure_solution 'WinGX-Version 1.70.01(Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0305P)^2^+0.2713P] 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 2239 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0687 _refine_ls_wR_factor_gt 0.0653 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 F1A F 0.1757(6) 0.4743(3) 1.4012(2) 0.0827(10) Uani 0.730(5) 1 d P A -1 C8A C 0.3778(5) 0.3316(3) 1.1068(2) 0.0463(6) Uani 0.730(5) 1 d P A -1 C9A C 0.5862(5) 0.4314(3) 1.1275(3) 0.0610(7) Uani 0.730(5) 1 d P A -1 H9A H 0.6824 0.4251 1.0656 0.073 Uiso 0.730(5) 1 calc PR A -1 C10A C 0.6492(7) 0.5411(3) 1.2422(4) 0.0757(10) Uani 0.730(5) 1 d P A -1 H10A H 0.7908 0.6074 1.2563 0.091 Uiso 0.730(5) 1 calc PR A -1 C11A C 0.5114(7) 0.5550(3) 1.3345(3) 0.0716(9) Uani 0.730(5) 1 d P A -1 H11A H 0.5553 0.6292 1.4109 0.086 Uiso 0.730(5) 1 calc PR A -1 C12A C 0.3077(6) 0.4565(3) 1.3108(3) 0.0650(8) Uani 0.730(5) 1 d P A -1 C13A C 0.2341(5) 0.3442(3) 1.1994(2) 0.0549(7) Uani 0.730(5) 1 d P A -1 H13A H 0.0919 0.2790 1.1870 0.066 Uiso 0.730(5) 1 calc PR A -1 F1B F 0.8036(16) 0.6363(8) 1.2682(8) 0.101(3) Uani 0.270(5) 1 d P A -2 C8B C 0.3778(5) 0.3316(3) 1.1068(2) 0.0463(6) Uani 0.270(5) 1 d P A -2 C13B C 0.5862(5) 0.4314(3) 1.1275(3) 0.0610(7) Uani 0.270(5) 1 d P A -2 H13B H 0.6824 0.4251 1.0656 0.073 Uiso 0.270(5) 1 calc PR A -2 C12B C 0.6492(7) 0.5411(3) 1.2422(4) 0.0757(10) Uani 0.270(5) 1 d P A -2 C11B C 0.5114(7) 0.5550(3) 1.3345(3) 0.0716(9) Uani 0.270(5) 1 d P A -2 H11B H 0.5553 0.6292 1.4109 0.086 Uiso 0.270(5) 1 calc PR A -2 C10B C 0.3077(6) 0.4565(3) 1.3108(3) 0.0650(8) Uani 0.270(5) 1 d P A -2 H10B H 0.2114 0.4648 1.3732 0.078 Uiso 0.270(5) 1 calc PR A -2 C9B C 0.2341(5) 0.3442(3) 1.1994(2) 0.0549(7) Uani 0.270(5) 1 d P A -2 H9B H 0.0919 0.2790 1.1870 0.066 Uiso 0.270(5) 1 calc PR A -2 Br1 Br -0.30579(6) 0.15995(3) 0.71061(3) 0.06096(13) Uani 1 1 d . . . O1 O -0.1198(3) 0.1641(2) 0.97526(16) 0.0636(5) Uani 1 1 d . . . N1 N 0.3250(4) 0.2175(2) 0.99059(18) 0.0478(5) Uani 1 1 d . . . H1 H 0.4590 0.1929 0.9539 0.057 Uiso 1 1 calc R A . C1 C 0.0887(4) 0.0314(2) 0.8076(2) 0.0378(5) Uani 1 1 d . . . C2 C 0.2599(5) -0.0680(3) 0.7945(2) 0.0486(6) Uani 1 1 d . A . H2 H 0.3786 -0.0626 0.8626 0.058 Uiso 1 1 calc R . . C3 C 0.2563(6) -0.1754(3) 0.6812(3) 0.0575(7) Uani 1 1 d . . . H3 H 0.3717 -0.2417 0.6736 0.069 Uiso 1 1 calc R A . C4 C 0.0833(6) -0.1840(3) 0.5804(3) 0.0578(7) Uani 1 1 d . A . H4 H 0.0798 -0.2569 0.5047 0.069 Uiso 1 1 calc R . . C5 C -0.0858(5) -0.0852(3) 0.5906(2) 0.0520(6) Uani 1 1 d . . . H5 H -0.2014 -0.0902 0.5218 0.062 Uiso 1 1 calc R A . C6 C -0.0822(4) 0.0212(2) 0.7038(2) 0.0407(5) Uani 1 1 d . A . C7 C 0.0849(4) 0.1436(3) 0.9318(2) 0.0424(5) Uani 1 1 d . A . 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 F1A 0.105(2) 0.0812(18) 0.0416(14) 0.0027(12) 0.0180(13) 0.0091(14) C8A 0.0342(12) 0.0466(14) 0.0445(14) 0.0074(11) -0.0041(10) 0.0108(10) C9A 0.0485(16) 0.0524(16) 0.0695(19) 0.0142(14) 0.0042(13) 0.0059(13) C10A 0.063(2) 0.0472(18) 0.090(3) 0.0098(17) -0.0129(19) 0.0028(16) C11A 0.070(2) 0.0512(18) 0.064(2) -0.0001(15) -0.0121(17) 0.0193(16) C12A 0.0669(19) 0.069(2) 0.0453(16) 0.0095(14) 0.0011(14) 0.0278(16) C13A 0.0489(15) 0.0590(17) 0.0406(14) 0.0057(12) 0.0012(12) 0.0102(12) F1B 0.089(6) 0.069(5) 0.108(7) 0.008(4) 0.007(5) -0.024(4) C8B 0.0342(12) 0.0466(14) 0.0445(14) 0.0074(11) -0.0041(10) 0.0108(10) C13B 0.0485(16) 0.0524(16) 0.0695(19) 0.0142(14) 0.0042(13) 0.0059(13) C12B 0.063(2) 0.0472(18) 0.090(3) 0.0098(17) -0.0129(19) 0.0028(16) C11B 0.070(2) 0.0512(18) 0.064(2) -0.0001(15) -0.0121(17) 0.0193(16) C10B 0.0669(19) 0.069(2) 0.0453(16) 0.0095(14) 0.0011(14) 0.0278(16) C9B 0.0489(15) 0.0590(17) 0.0406(14) 0.0057(12) 0.0012(12) 0.0102(12) Br1 0.05933(19) 0.0661(2) 0.0616(2) 0.02981(15) 0.00689(13) 0.02268(14) O1 0.0300(9) 0.0931(15) 0.0445(10) 0.0038(10) 0.0087(8) 0.0073(9) N1 0.0298(10) 0.0568(13) 0.0410(11) 0.0038(10) 0.0062(8) 0.0062(9) C1 0.0298(11) 0.0440(13) 0.0352(12) 0.0118(10) 0.0066(9) 0.0016(9) C2 0.0442(14) 0.0552(15) 0.0438(14) 0.0182(12) 0.0040(11) 0.0117(11) C3 0.0607(17) 0.0502(16) 0.0597(17) 0.0176(14) 0.0151(14) 0.0195(13) C4 0.0667(18) 0.0479(16) 0.0448(15) 0.0038(12) 0.0128(13) 0.0052(13) C5 0.0538(16) 0.0565(16) 0.0360(14) 0.0129(12) -0.0014(11) -0.0005(12) C6 0.0351(12) 0.0436(13) 0.0428(13) 0.0173(11) 0.0067(10) 0.0039(10) C7 0.0325(12) 0.0518(14) 0.0366(13) 0.0117(11) 0.0040(10) 0.0092(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1A C12A 1.312(4) . ? C8A C13A 1.383(4) . ? C8A C9A 1.385(4) . ? C8A N1 1.419(3) . ? C9A C10A 1.388(4) . ? C9A H9A 0.9300 . ? C10A C11A 1.358(5) . ? C10A H10A 0.9300 . ? C11A C12A 1.351(5) . ? C11A H11A 0.9300 . ? C12A C13A 1.381(4) . ? C13A H13A 0.9300 . ? Br1 C6 1.901(2) . ? O1 C7 1.220(3) . ? N1 C7 1.353(3) . ? N1 H1 0.8600 . ? C1 C6 1.385(3) . ? C1 C2 1.386(3) . ? C1 C7 1.500(3) . ? C2 C3 1.385(4) . ? C2 H2 0.9300 . ? C3 C4 1.368(4) . ? C3 H3 0.9300 . ? C4 C5 1.377(4) . ? C4 H4 0.9300 . ? C5 C6 1.380(3) . ? C5 H5 0.9300 . ? 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 C13A C8A C9A 119.6(2) . . ? C13A C8A N1 122.5(2) . . ? C9A C8A N1 117.9(2) . . ? C8A C9A C10A 119.0(3) . . ? C8A C9A H9A 120.5 . . ? C10A C9A H9A 120.5 . . ? C11A C10A C9A 122.3(3) . . ? C11A C10A H10A 118.9 . . ? C9A C10A H10A 118.9 . . ? C12A C11A C10A 117.2(3) . . ? C12A C11A H11A 121.4 . . ? C10A C11A H11A 121.4 . . ? F1A C12A C11A 115.6(3) . . ? F1A C12A C13A 120.5(3) . . ? C11A C12A C13A 123.8(3) . . ? C12A C13A C8A 118.1(3) . . ? C12A C13A H13A 120.9 . . ? C8A C13A H13A 120.9 . . ? C7 N1 C8A 126.5(2) . . ? C7 N1 H1 116.7 . . ? C8A N1 H1 116.7 . . ? C6 C1 C2 118.0(2) . . ? C6 C1 C7 121.6(2) . . ? C2 C1 C7 120.4(2) . . ? C3 C2 C1 120.8(2) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C4 C3 C2 120.1(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.3(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 119.4(2) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C1 121.5(2) . . ? C5 C6 Br1 117.48(18) . . ? C1 C6 Br1 120.93(18) . . ? O1 C7 N1 123.6(2) . . ? O1 C7 C1 121.9(2) . . ? N1 C7 C1 114.56(19) . . ? 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 C13A C8A C9A C10A 1.2(4) . . . . ? N1 C8A C9A C10A -177.3(2) . . . . ? C8A C9A C10A C11A -0.9(5) . . . . ? C9A C10A C11A C12A 0.2(5) . . . . ? C10A C11A C12A F1A -178.8(3) . . . . ? C10A C11A C12A C13A 0.1(5) . . . . ? F1A C12A C13A C8A 179.1(3) . . . . ? C11A C12A C13A C8A 0.2(4) . . . . ? C9A C8A C13A C12A -0.9(4) . . . . ? N1 C8A C13A C12A 177.5(2) . . . . ? C13A C8A N1 C7 31.5(4) . . . . ? C9A C8A N1 C7 -150.0(3) . . . . ? C6 C1 C2 C3 -1.0(4) . . . . ? C7 C1 C2 C3 177.1(2) . . . . ? C1 C2 C3 C4 0.3(4) . . . . ? C2 C3 C4 C5 0.8(4) . . . . ? C3 C4 C5 C6 -1.1(4) . . . . ? C4 C5 C6 C1 0.3(4) . . . . ? C4 C5 C6 Br1 176.6(2) . . . . ? C2 C1 C6 C5 0.7(3) . . . . ? C7 C1 C6 C5 -177.3(2) . . . . ? C2 C1 C6 Br1 -175.45(18) . . . . ? C7 C1 C6 Br1 6.5(3) . . . . ? C8A N1 C7 O1 -2.7(4) . . . . ? C8A N1 C7 C1 177.9(2) . . . . ? C6 C1 C7 O1 54.1(4) . . . . ? C2 C1 C7 O1 -123.9(3) . . . . ? C6 C1 C7 N1 -126.5(2) . . . . ? C2 C1 C7 N1 55.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.238 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.048 #============================================================================== data_3FA-3BrB _database_code_depnum_ccdc_archive 'CCDC 764626' #TrackingRef '- CIF.cif' #============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-bromo-N-(3-fluorophenyl)benzamide ; _chemical_name_common 3-bromo-N-(3-fluorophenyl)benzamide _chemical_formula_sum 'C13 H9 Br F N O' _chemical_formula_weight 294.12 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.3711(4) _cell_length_b 5.1917(5) _cell_length_c 50.481(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1145.59(19) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 360 _cell_measurement_theta_min 0.97 _cell_measurement_theta_max 27.89 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.705 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 3.582 _exptl_absorpt_correction_T_min 0.4679 _exptl_absorpt_correction_T_max 0.6340 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% ? _diffrn_reflns_number 11914 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -62 _diffrn_reflns_limit_l_max 62 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2267 _reflns_number_gt 1967 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction SAINT _computing_structure_solution 'WinGX-Version 1.70.01(Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0002P)^2^+0.7683P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.033(14) _refine_ls_number_reflns 2267 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0691 _refine_ls_wR_factor_gt 0.0673 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _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 F1A F 0.9103(9) 0.2282(7) 0.52139(6) 0.0817(13) Uani 0.677(5) 1 d P A -1 C8A C 1.0123(8) -0.1346(6) 0.58075(6) 0.0367(8) Uani 0.677(5) 1 d P A -1 C9A C 1.2098(8) -0.3210(6) 0.57178(6) 0.0447(9) Uani 0.677(5) 1 d P A -1 H9A H 1.2762 -0.4507 0.5831 0.054 Uiso 0.677(5) 1 calc PR A -1 C10A C 1.3101(9) -0.3144(7) 0.54560(7) 0.0525(10) Uani 0.677(5) 1 d P A -1 H10A H 1.4447 -0.4402 0.5396 0.063 Uiso 0.677(5) 1 calc PR A -1 C11A C 1.2132(9) -0.1252(7) 0.52853(7) 0.0496(10) Uani 0.677(5) 1 d P A -1 H11A H 1.2802 -0.1198 0.5110 0.060 Uiso 0.677(5) 1 calc PR A -1 C12A C 1.0145(10) 0.0550(7) 0.53823(7) 0.0526(11) Uani 0.677(5) 1 d P A -1 C13A C 0.9117(10) 0.0563(6) 0.56386(6) 0.0466(9) Uani 0.677(5) 1 d P A -1 H13A H 0.7774 0.1829 0.5697 0.056 Uiso 0.677(5) 1 calc PR A -1 F1B F 1.4976(17) -0.4845(14) 0.53744(13) 0.066(3) Uani 0.323(5) 1 d P A -2 C8B C 1.0123(8) -0.1346(6) 0.58075(6) 0.0367(8) Uani 0.323(5) 1 d P A -2 C13B C 1.2098(8) -0.3210(6) 0.57178(6) 0.0447(9) Uani 0.323(5) 1 d P A -2 H13B H 1.2762 -0.4507 0.5831 0.054 Uiso 0.323(5) 1 calc PR A -2 C12B C 1.3101(9) -0.3144(7) 0.54560(7) 0.0525(10) Uani 0.323(5) 1 d P A -2 C11B C 1.2132(9) -0.1252(7) 0.52853(7) 0.0496(10) Uani 0.323(5) 1 d P A -2 H11B H 1.2802 -0.1198 0.5110 0.060 Uiso 0.323(5) 1 calc PR A -2 C10B C 1.0145(10) 0.0550(7) 0.53823(7) 0.0526(11) Uani 0.323(5) 1 d P A -2 H10B H 0.9455 0.1833 0.5268 0.063 Uiso 0.323(5) 1 calc PR A -2 C9B C 0.9117(10) 0.0563(6) 0.56386(6) 0.0466(9) Uani 0.323(5) 1 d P A -2 H9B H 0.7774 0.1829 0.5697 0.056 Uiso 0.323(5) 1 calc PR A -2 Br1 Br 0.88483(10) 0.26715(9) 0.726061(6) 0.06496(15) Uani 1 1 d . A . O1 O 0.9020(8) 0.2714(4) 0.61782(4) 0.0689(8) Uani 1 1 d . . . N1 N 0.9059(7) -0.1536(5) 0.60732(5) 0.0411(6) Uani 1 1 d . . . H1 H 0.8714 -0.3054 0.6134 0.049 Uiso 1 1 calc R A . C1 C 0.7410(8) -0.0251(6) 0.65077(6) 0.0380(8) Uani 1 1 d . . . C2 C 0.5512(7) -0.2322(7) 0.65550(6) 0.0465(8) Uani 1 1 d . A . H2 H 0.4864 -0.3349 0.6415 0.056 Uiso 1 1 calc R . . C3 C 0.4563(6) -0.2882(5) 0.68121(5) 0.0603(10) Uani 1 1 d . . . H3 H 0.3281 -0.4280 0.6843 0.072 Uiso 1 1 calc R A . C4 C 0.5513(6) -0.1378(5) 0.70200(5) 0.0526(10) Uani 1 1 d R A . H4 H 0.4871 -0.1742 0.7192 0.063 Uiso 1 1 calc R . . C5 C 0.7409(9) 0.0656(7) 0.69724(6) 0.0426(9) Uani 1 1 d . . . C6 C 0.8328(9) 0.1267(6) 0.67187(6) 0.0442(9) Uani 1 1 d . A . H6 H 0.9564 0.2698 0.6689 0.053 Uiso 1 1 calc R . . C7 C 0.8546(9) 0.0473(6) 0.62374(6) 0.0407(8) Uani 1 1 d . A . 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 F1A 0.125(3) 0.081(2) 0.0394(17) 0.0216(18) -0.0041(19) 0.020(3) C8A 0.050(2) 0.0356(16) 0.0244(15) 0.0003(13) 0.0006(14) -0.0111(15) C9A 0.057(2) 0.042(2) 0.0355(17) 0.0055(14) -0.0010(16) 0.0004(16) C10A 0.057(2) 0.057(2) 0.0426(19) -0.0045(17) 0.0119(17) -0.001(2) C11A 0.059(2) 0.061(2) 0.0289(17) 0.0033(16) 0.0045(16) -0.0135(19) C12A 0.075(3) 0.049(2) 0.0342(19) 0.0104(16) -0.0054(18) -0.006(2) C13A 0.067(3) 0.0422(18) 0.0301(16) 0.0026(13) 0.0005(18) 0.003(2) F1B 0.080(6) 0.073(5) 0.046(4) 0.007(3) 0.023(4) 0.028(4) C8B 0.050(2) 0.0356(16) 0.0244(15) 0.0003(13) 0.0006(14) -0.0111(15) C13B 0.057(2) 0.042(2) 0.0355(17) 0.0055(14) -0.0010(16) 0.0004(16) C12B 0.057(2) 0.057(2) 0.0426(19) -0.0045(17) 0.0119(17) -0.001(2) C11B 0.059(2) 0.061(2) 0.0289(17) 0.0033(16) 0.0045(16) -0.0135(19) C10B 0.075(3) 0.049(2) 0.0342(19) 0.0104(16) -0.0054(18) -0.006(2) C9B 0.067(3) 0.0422(18) 0.0301(16) 0.0026(13) 0.0005(18) 0.003(2) Br1 0.0903(3) 0.0740(3) 0.03054(16) -0.0072(2) -0.0015(2) 0.0030(3) O1 0.138(2) 0.0307(12) 0.0381(12) 0.0004(11) 0.0188(15) -0.012(2) N1 0.0650(18) 0.0309(13) 0.0274(12) 0.0021(10) 0.0049(14) -0.0032(14) C1 0.051(2) 0.0335(17) 0.0298(15) 0.0025(13) 0.0030(15) 0.0060(16) C2 0.051(2) 0.0457(18) 0.0425(17) -0.0020(17) 0.0004(14) -0.003(2) C3 0.069(3) 0.053(2) 0.059(2) 0.0012(19) 0.0194(19) -0.013(2) C4 0.062(3) 0.057(2) 0.0388(19) 0.0065(17) 0.0171(18) 0.005(2) C5 0.058(2) 0.045(2) 0.0241(15) -0.0015(14) -0.0017(15) 0.0131(17) C6 0.065(3) 0.0379(16) 0.0293(16) -0.0008(13) 0.0049(16) -0.0016(17) C7 0.061(2) 0.0359(17) 0.0248(15) 0.0029(12) -0.0004(17) -0.0021(18) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1A C12A 1.318(5) . ? C8A C9A 1.373(5) . ? C8A C13A 1.379(4) . ? C8A N1 1.423(4) . ? C9A C10A 1.393(5) . ? C9A H9A 0.9300 . ? C10A C11A 1.374(5) . ? C10A H10A 0.9300 . ? C11A C12A 1.367(5) . ? C11A H11A 0.9300 . ? C12A C13A 1.370(5) . ? C13A H13A 0.9300 . ? Br1 C5 1.899(3) . ? O1 C7 1.219(4) . ? N1 C7 1.351(4) . ? N1 H1 0.8600 . ? C1 C2 1.379(5) . ? C1 C6 1.385(4) . ? C1 C7 1.500(4) . ? C2 C3 1.394(4) . ? C2 H2 0.9300 . ? C3 C4 1.3721 . ? C3 H3 0.9300 . ? C4 C5 1.364(5) . ? C4 H4 0.9300 . ? C5 C6 1.379(4) . ? C6 H6 0.9300 . ? 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 C9A C8A C13A 120.2(3) . . ? C9A C8A N1 117.9(3) . . ? C13A C8A N1 121.9(3) . . ? C8A C9A C10A 119.6(3) . . ? C8A C9A H9A 120.2 . . ? C10A C9A H9A 120.2 . . ? C11A C10A C9A 121.0(3) . . ? C11A C10A H10A 119.5 . . ? C9A C10A H10A 119.5 . . ? C12A C11A C10A 117.4(3) . . ? C12A C11A H11A 121.3 . . ? C10A C11A H11A 121.3 . . ? F1A C12A C11A 117.1(3) . . ? F1A C12A C13A 119.5(4) . . ? C11A C12A C13A 123.4(3) . . ? C12A C13A C8A 118.4(3) . . ? C12A C13A H13A 120.8 . . ? C8A C13A H13A 120.8 . . ? C7 N1 C8A 125.4(3) . . ? C7 N1 H1 117.3 . . ? C8A N1 H1 117.3 . . ? C2 C1 C6 119.0(3) . . ? C2 C1 C7 123.5(3) . . ? C6 C1 C7 117.5(3) . . ? C1 C2 C3 120.2(3) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 120.24(19) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 119.34(17) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 121.2(3) . . ? C4 C5 Br1 119.6(2) . . ? C6 C5 Br1 119.2(3) . . ? C5 C6 C1 119.9(3) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? O1 C7 N1 123.9(3) . . ? O1 C7 C1 121.2(3) . . ? N1 C7 C1 114.8(3) . . ? 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 C13A C8A C9A C10A 0.6(5) . . . . ? N1 C8A C9A C10A 177.6(3) . . . . ? C8A C9A C10A C11A -0.4(5) . . . . ? C9A C10A C11A C12A -0.2(6) . . . . ? C10A C11A C12A F1A -176.6(4) . . . . ? C10A C11A C12A C13A 0.6(6) . . . . ? F1A C12A C13A C8A 176.8(4) . . . . ? C11A C12A C13A C8A -0.4(6) . . . . ? C9A C8A C13A C12A -0.3(5) . . . . ? N1 C8A C13A C12A -177.1(4) . . . . ? C9A C8A N1 C7 143.6(4) . . . . ? C13A C8A N1 C7 -39.5(5) . . . . ? C6 C1 C2 C3 -0.5(5) . . . . ? C7 C1 C2 C3 179.7(3) . . . . ? C1 C2 C3 C4 -0.1(4) . . . . ? C2 C3 C4 C5 -0.4(2) . . . . ? C3 C4 C5 C6 1.6(4) . . . . ? C3 C4 C5 Br1 -177.78(12) . . . . ? C4 C5 C6 C1 -2.2(5) . . . . ? Br1 C5 C6 C1 177.1(3) . . . . ? C2 C1 C6 C5 1.7(5) . . . . ? C7 C1 C6 C5 -178.5(3) . . . . ? C8A N1 C7 O1 -2.0(7) . . . . ? C8A N1 C7 C1 179.7(3) . . . . ? C2 C1 C7 O1 147.7(4) . . . . ? C6 C1 C7 O1 -32.1(6) . . . . ? C2 C1 C7 N1 -34.0(5) . . . . ? C6 C1 C7 N1 146.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.331 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.047 #============================================================================== data_2FB-2ClA _database_code_depnum_ccdc_archive 'CCDC 764627' #TrackingRef '- CIF.cif' #============================================================================= _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-fluoro-N-(2-chlorophenyl)benzamide ; _chemical_name_common 2-fluoro-N-(2-chlorophenyl)benzamide _chemical_formula_moiety 'C13 H9 Cl F N O' _chemical_formula_sum 'C13 H9 Cl F N O' _chemical_formula_weight 249.66 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.0184(16) _cell_length_b 4.7429(7) _cell_length_c 21.677(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.101(2) _cell_angle_gamma 90.00 _cell_volume 1129.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 375 _cell_measurement_theta_min 0.97 _cell_measurement_theta_max 27.79 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.332 _exptl_absorpt_correction_T_min 0.9071 _exptl_absorpt_correction_T_max 0.9397 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10905 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2216 _reflns_number_gt 1797 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction SAINT _computing_structure_solution 'WinGX-Version 1.70.01(Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0478P)^2^+0.3116P] 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 2216 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 F1A F 0.70290(13) 0.2880(3) 0.21192(6) 0.0724(6) Uani 0.887(4) 1 d P A -1 C1A C 0.53501(16) -0.0129(4) 0.18979(8) 0.0426(4) Uani 0.887(4) 1 d P A -1 C2A C 0.59590(18) 0.1815(4) 0.22799(9) 0.0514(5) Uani 0.887(4) 1 d P A -1 C3A C 0.5541(2) 0.2683(5) 0.28304(10) 0.0668(6) Uani 0.887(4) 1 d P A -1 H3A H 0.5976 0.3992 0.3077 0.080 Uiso 0.887(4) 1 calc PR A -1 C4A C 0.4469(2) 0.1584(5) 0.30099(10) 0.0695(7) Uani 0.887(4) 1 d P A -1 H4A H 0.4172 0.2153 0.3381 0.083 Uiso 0.887(4) 1 calc PR A -1 C5A C 0.3832(2) -0.0352(5) 0.26437(10) 0.0651(6) Uani 0.887(4) 1 d P A -1 H5A H 0.3103 -0.1080 0.2766 0.078 Uiso 0.887(4) 1 calc PR A -1 C6A C 0.42694(19) -0.1211(4) 0.20985(9) 0.0552(5) Uani 0.887(4) 1 d P A -1 H6A H 0.3837 -0.2544 0.1857 0.066 Uiso 0.887(4) 1 calc PR A -1 F1B F 0.3625(10) -0.304(3) 0.1759(5) 0.079(5) Uani 0.113(4) 1 d P A -2 C1B C 0.53501(16) -0.0129(4) 0.18979(8) 0.0426(4) Uani 0.113(4) 1 d P A -2 C6B C 0.59590(18) 0.1815(4) 0.22799(9) 0.0514(5) Uani 0.113(4) 1 d P A -2 H6B H 0.6684 0.2569 0.2159 0.062 Uiso 0.113(4) 1 calc PR A -2 C5B C 0.5541(2) 0.2683(5) 0.28304(10) 0.0668(6) Uani 0.113(4) 1 d P A -2 H5B H 0.5976 0.3992 0.3077 0.080 Uiso 0.113(4) 1 calc PR A -2 C4B C 0.4469(2) 0.1584(5) 0.30099(10) 0.0695(7) Uani 0.113(4) 1 d P A -2 H4B H 0.4172 0.2153 0.3381 0.083 Uiso 0.113(4) 1 calc PR A -2 C3B C 0.3832(2) -0.0352(5) 0.26437(10) 0.0651(6) Uani 0.113(4) 1 d P A -2 H3B H 0.3103 -0.1080 0.2766 0.078 Uiso 0.113(4) 1 calc PR A -2 C2B C 0.42694(19) -0.1211(4) 0.20985(9) 0.0552(5) Uani 0.113(4) 1 d P A -2 Cl1 Cl 0.87150(5) 0.35335(12) 0.07994(2) 0.0636(2) Uani 1 1 d . . . N1 N 0.64137(14) 0.0549(3) 0.09694(7) 0.0460(4) Uani 1 1 d . A . H1 H 0.6523 0.2224 0.1115 0.055 Uiso 1 1 calc R . . O1 O 0.55517(15) -0.3673(3) 0.11452(7) 0.0649(4) Uani 1 1 d . A . C7 C 0.57841(16) -0.1248(4) 0.13039(8) 0.0432(4) Uani 1 1 d . . . C8 C 0.69134(16) -0.0054(4) 0.04004(8) 0.0419(4) Uani 1 1 d . . . C9 C 0.79818(17) 0.1278(4) 0.02612(8) 0.0463(4) Uani 1 1 d . A . C10 C 0.8491(2) 0.0803(5) -0.02935(9) 0.0590(5) Uani 1 1 d . . . H10 H 0.9201 0.1731 -0.0383 0.071 Uiso 1 1 calc R A . C11 C 0.7938(2) -0.1057(5) -0.07127(10) 0.0640(6) Uani 1 1 d . A . H11 H 0.8284 -0.1415 -0.1084 0.077 Uiso 1 1 calc R . . C12 C 0.6882(2) -0.2378(5) -0.05855(9) 0.0599(5) Uani 1 1 d . . . H12 H 0.6511 -0.3620 -0.0872 0.072 Uiso 1 1 calc R A . C13 C 0.63620(18) -0.1884(4) -0.00349(9) 0.0504(5) Uani 1 1 d . A . H13 H 0.5639 -0.2780 0.0045 0.061 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 F1A 0.0706(10) 0.0819(11) 0.0641(9) -0.0138(7) 0.0002(7) -0.0240(8) C1A 0.0497(10) 0.0345(9) 0.0437(9) 0.0028(7) 0.0034(8) 0.0061(8) C2A 0.0577(12) 0.0471(11) 0.0487(11) 0.0008(8) -0.0007(9) 0.0018(9) C3A 0.0903(17) 0.0623(13) 0.0464(12) -0.0090(10) -0.0045(11) 0.0066(13) C4A 0.0903(17) 0.0727(15) 0.0468(12) 0.0017(11) 0.0153(11) 0.0274(13) C5A 0.0655(13) 0.0735(15) 0.0585(13) 0.0055(11) 0.0196(11) 0.0097(12) C6A 0.0583(12) 0.0530(12) 0.0552(12) 0.0008(9) 0.0103(10) 0.0005(10) F1B 0.080(8) 0.095(9) 0.066(7) -0.035(6) 0.031(6) -0.046(7) C1B 0.0497(10) 0.0345(9) 0.0437(9) 0.0028(7) 0.0034(8) 0.0061(8) C6B 0.0577(12) 0.0471(11) 0.0487(11) 0.0008(8) -0.0007(9) 0.0018(9) C5B 0.0903(17) 0.0623(13) 0.0464(12) -0.0090(10) -0.0045(11) 0.0066(13) C4B 0.0903(17) 0.0727(15) 0.0468(12) 0.0017(11) 0.0153(11) 0.0274(13) C3B 0.0655(13) 0.0735(15) 0.0585(13) 0.0055(11) 0.0196(11) 0.0097(12) C2B 0.0583(12) 0.0530(12) 0.0552(12) 0.0008(9) 0.0103(10) 0.0005(10) Cl1 0.0595(3) 0.0663(4) 0.0646(3) -0.0083(3) 0.0024(2) -0.0199(3) N1 0.0559(9) 0.0327(7) 0.0507(9) -0.0082(6) 0.0128(7) -0.0067(7) O1 0.0945(11) 0.0339(7) 0.0693(9) -0.0083(6) 0.0259(8) -0.0106(7) C7 0.0454(10) 0.0333(9) 0.0512(10) -0.0008(8) 0.0052(8) 0.0018(8) C8 0.0451(10) 0.0351(9) 0.0456(10) 0.0005(7) 0.0048(8) 0.0043(8) C9 0.0475(10) 0.0416(10) 0.0493(10) 0.0034(8) 0.0010(8) -0.0005(8) C10 0.0574(12) 0.0680(14) 0.0529(12) 0.0080(10) 0.0127(9) -0.0034(11) C11 0.0759(15) 0.0701(14) 0.0477(12) -0.0025(10) 0.0160(11) 0.0032(12) C12 0.0750(14) 0.0546(12) 0.0495(11) -0.0098(9) -0.0003(10) 0.0018(11) C13 0.0524(11) 0.0451(11) 0.0538(11) -0.0064(8) 0.0038(9) -0.0025(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1A C2A 1.351(2) . ? C1A C2A 1.381(3) . ? C1A C6A 1.395(3) . ? C1A C7 1.502(2) . ? C2A C3A 1.373(3) . ? C3A C4A 1.373(3) . ? C3A H3A 0.9300 . ? C4A C5A 1.373(3) . ? C4A H4A 0.9300 . ? C5A C6A 1.370(3) . ? C5A H5A 0.9300 . ? C6A H6A 0.9300 . ? Cl1 C9 1.7387(19) . ? N1 C7 1.344(2) . ? N1 C8 1.416(2) . ? N1 H1 0.8600 . ? O1 C7 1.222(2) . ? C8 C9 1.388(3) . ? C8 C13 1.389(3) . ? C9 C10 1.381(3) . ? C10 C11 1.377(3) . ? C10 H10 0.9300 . ? C11 C12 1.367(3) . ? C11 H11 0.9300 . ? C12 C13 1.381(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? 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 C2A C1A C6A 116.61(17) . . ? C2A C1A C7 125.40(16) . . ? C6A C1A C7 117.94(16) . . ? F1A C2A C3A 117.72(19) . . ? F1A C2A C1A 119.39(17) . . ? C3A C2A C1A 122.9(2) . . ? C2A C3A C4A 118.8(2) . . ? C2A C3A H3A 120.6 . . ? C4A C3A H3A 120.6 . . ? C3A C4A C5A 120.3(2) . . ? C3A C4A H4A 119.9 . . ? C5A C4A H4A 119.9 . . ? C6A C5A C4A 120.0(2) . . ? C6A C5A H5A 120.0 . . ? C4A C5A H5A 120.0 . . ? C5A C6A C1A 121.4(2) . . ? C5A C6A H6A 119.3 . . ? C1A C6A H6A 119.3 . . ? C7 N1 C8 126.14(15) . . ? C7 N1 H1 116.9 . . ? C8 N1 H1 116.9 . . ? O1 C7 N1 123.43(17) . . ? O1 C7 C1A 120.05(16) . . ? N1 C7 C1A 116.52(15) . . ? C9 C8 C13 118.24(16) . . ? C9 C8 N1 119.08(16) . . ? C13 C8 N1 122.66(16) . . ? C10 C9 C8 121.24(18) . . ? C10 C9 Cl1 119.09(15) . . ? C8 C9 Cl1 119.65(14) . . ? C11 C10 C9 119.39(19) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C12 C11 C10 120.23(19) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 120.6(2) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 120.30(19) . . ? C12 C13 H13 119.8 . . ? C8 C13 H13 119.8 . . ? 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 C6A C1A C2A F1A 178.15(17) . . . . ? C7 C1A C2A F1A 1.0(3) . . . . ? C6A C1A C2A C3A -0.2(3) . . . . ? C7 C1A C2A C3A -177.41(18) . . . . ? F1A C2A C3A C4A -178.63(19) . . . . ? C1A C2A C3A C4A -0.2(3) . . . . ? C2A C3A C4A C5A 0.1(3) . . . . ? C3A C4A C5A C6A 0.5(3) . . . . ? C4A C5A C6A C1A -1.0(3) . . . . ? C2A C1A C6A C5A 0.8(3) . . . . ? C7 C1A C6A C5A 178.22(18) . . . . ? C8 N1 C7 O1 -1.0(3) . . . . ? C8 N1 C7 C1A 179.57(16) . . . . ? C2A C1A C7 O1 146.7(2) . . . . ? C6A C1A C7 O1 -30.4(3) . . . . ? C2A C1A C7 N1 -33.8(3) . . . . ? C6A C1A C7 N1 149.04(18) . . . . ? C7 N1 C8 C9 -147.92(18) . . . . ? C7 N1 C8 C13 33.7(3) . . . . ? C13 C8 C9 C10 -0.2(3) . . . . ? N1 C8 C9 C10 -178.65(17) . . . . ? C13 C8 C9 Cl1 -178.82(14) . . . . ? N1 C8 C9 Cl1 2.7(2) . . . . ? C8 C9 C10 C11 -0.9(3) . . . . ? Cl1 C9 C10 C11 177.73(16) . . . . ? C9 C10 C11 C12 1.2(3) . . . . ? C10 C11 C12 C13 -0.5(3) . . . . ? C11 C12 C13 C8 -0.6(3) . . . . ? C9 C8 C13 C12 1.0(3) . . . . ? N1 C8 C13 C12 179.37(18) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.219 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.038 #========================================================================== data_3FB-4ClA _database_code_depnum_ccdc_archive 'CCDC 764628' #TrackingRef '- CIF.cif' #============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-fluoro-N-(4-chlorophenyl)benzamide ; _chemical_name_common 3-fluoro-N-(4-chlorophenyl)benzamide _chemical_formula_sum 'C13 H9 Cl F N O' _chemical_formula_weight 249.66 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 2/c' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.6859(6) _cell_length_b 5.24250(10) _cell_length_c 17.3988(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.2520(10) _cell_angle_gamma 90.00 _cell_volume 2270.78(9) _cell_formula_units_Z 8 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 350 _cell_measurement_theta_min 0.97 _cell_measurement_theta_max 27.98 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.330 _exptl_absorpt_correction_T_min 0.9133 _exptl_absorpt_correction_T_max 0.9677 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17504 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2112 _reflns_number_gt 1634 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction SAINT _computing_structure_solution 'WinGX-Version 1.70.01(Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0933P)^2^+0.6324P] 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 2112 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1529 _refine_ls_wR_factor_gt 0.1248 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _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 F1A F 0.48423(12) 0.1745(6) 0.5389(2) 0.0724(12) Uani 0.487(4) 1 d P A -1 C1A C 0.37166(9) 0.5986(4) 0.51398(13) 0.0367(5) Uani 0.487(4) 1 d P A -1 C2A C 0.40320(10) 0.3950(4) 0.50171(15) 0.0489(6) Uani 0.487(4) 1 d P A -1 H2A H 0.3908 0.2827 0.4598 0.059 Uiso 0.487(4) 1 calc PR A -1 C3A C 0.45308(11) 0.3617(5) 0.55259(18) 0.0590(7) Uani 0.487(4) 1 d P A -1 C4A C 0.47192(10) 0.5184(6) 0.61669(18) 0.0623(8) Uani 0.487(4) 1 d P A -1 H4A H 0.5053 0.4904 0.6512 0.075 Uiso 0.487(4) 1 calc PR A -1 C5A C 0.44020(11) 0.7165(5) 0.62821(15) 0.0573(7) Uani 0.487(4) 1 d P A -1 H5A H 0.4523 0.8240 0.6714 0.069 Uiso 0.487(4) 1 calc PR A -1 C6A C 0.39079(10) 0.7613(5) 0.57767(14) 0.0463(6) Uani 0.487(4) 1 d P A -1 H6A H 0.3703 0.8999 0.5861 0.056 Uiso 0.487(4) 1 calc PR A -1 F1B F 0.45935(16) 0.8713(8) 0.6881(2) 0.1044(16) Uani 0.513(4) 1 d P A -2 C1B C 0.37166(9) 0.5986(4) 0.51398(13) 0.0367(5) Uani 0.513(4) 1 d P A -2 C6B C 0.40320(10) 0.3950(4) 0.50171(15) 0.0489(6) Uani 0.513(4) 1 d P A -2 H6B H 0.3908 0.2827 0.4598 0.059 Uiso 0.513(4) 1 calc PR A -2 C5B C 0.45308(11) 0.3617(5) 0.55259(18) 0.0590(7) Uani 0.513(4) 1 d P A -2 H5B H 0.4747 0.2288 0.5433 0.071 Uiso 0.513(4) 1 calc PR A -2 C4B C 0.47192(10) 0.5184(6) 0.61669(18) 0.0623(8) Uani 0.513(4) 1 d P A -2 H4B H 0.5053 0.4904 0.6512 0.075 Uiso 0.513(4) 1 calc PR A -2 C3B C 0.44020(11) 0.7165(5) 0.62821(15) 0.0573(7) Uani 0.513(4) 1 d P A -2 C2B C 0.39079(10) 0.7613(5) 0.57767(14) 0.0463(6) Uani 0.513(4) 1 d P A -2 H2B H 0.3703 0.8999 0.5861 0.056 Uiso 0.513(4) 1 calc PR A -2 Cl1 Cl 0.08806(3) 0.42944(15) 0.17147(4) 0.0703(3) Uani 1 1 d . . . N1 N 0.28969(7) 0.4515(3) 0.42373(10) 0.0372(5) Uani 1 1 d . A . H1 H 0.3029 0.3032 0.4380 0.045 Uiso 1 1 calc R . . O1 O 0.30182(7) 0.8761(3) 0.44780(10) 0.0503(5) Uani 1 1 d . A . C7 C 0.31836(9) 0.6569(4) 0.45922(12) 0.0359(5) Uani 1 1 d . . . C8 C 0.24050(8) 0.4590(4) 0.36586(12) 0.0334(5) Uani 1 1 d . . . C9 C 0.20430(9) 0.2606(4) 0.36282(13) 0.0390(5) Uani 1 1 d . A . H9 H 0.2118 0.1324 0.4009 0.047 Uiso 1 1 calc R . . C10 C 0.15724(9) 0.2517(4) 0.30387(14) 0.0434(6) Uani 1 1 d . . . H10 H 0.1331 0.1183 0.3021 0.052 Uiso 1 1 calc R A . C11 C 0.14638(9) 0.4432(4) 0.24744(13) 0.0399(5) Uani 1 1 d . A . C12 C 0.18164(9) 0.6421(4) 0.24983(13) 0.0400(5) Uani 1 1 d . . . H12 H 0.1738 0.7705 0.2118 0.048 Uiso 1 1 calc R A . C13 C 0.22880(9) 0.6506(4) 0.30887(12) 0.0374(5) Uani 1 1 d . A . H13 H 0.2527 0.7848 0.3105 0.045 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 F1A 0.0420(18) 0.068(2) 0.097(3) -0.0100(18) -0.0025(16) 0.0281(15) C1A 0.0359(12) 0.0330(11) 0.0392(11) 0.0037(8) 0.0055(9) 0.0004(9) C2A 0.0452(14) 0.0419(13) 0.0564(14) -0.0038(11) 0.0065(11) 0.0054(11) C3A 0.0421(14) 0.0530(15) 0.0774(18) 0.0028(13) 0.0062(13) 0.0134(12) C4A 0.0370(14) 0.0679(17) 0.0719(18) 0.0091(15) -0.0059(13) 0.0035(13) C5A 0.0501(15) 0.0610(16) 0.0517(14) -0.0070(12) -0.0048(12) -0.0048(13) C6A 0.0438(13) 0.0423(12) 0.0487(13) -0.0036(10) 0.0033(10) 0.0032(10) F1B 0.073(3) 0.136(4) 0.086(3) -0.043(3) -0.015(2) 0.006(2) C1B 0.0359(12) 0.0330(11) 0.0392(11) 0.0037(8) 0.0055(9) 0.0004(9) C6B 0.0452(14) 0.0419(13) 0.0564(14) -0.0038(11) 0.0065(11) 0.0054(11) C5B 0.0421(14) 0.0530(15) 0.0774(18) 0.0028(13) 0.0062(13) 0.0134(12) C4B 0.0370(14) 0.0679(17) 0.0719(18) 0.0091(15) -0.0059(13) 0.0035(13) C3B 0.0501(15) 0.0610(16) 0.0517(14) -0.0070(12) -0.0048(12) -0.0048(13) C2B 0.0438(13) 0.0423(12) 0.0487(13) -0.0036(10) 0.0033(10) 0.0032(10) Cl1 0.0483(5) 0.0835(6) 0.0648(5) 0.0068(4) -0.0132(3) -0.0140(3) N1 0.0384(10) 0.0263(9) 0.0425(10) 0.0022(7) 0.0013(8) 0.0035(7) O1 0.0515(10) 0.0285(8) 0.0591(10) -0.0023(7) -0.0092(8) 0.0058(7) C7 0.0391(12) 0.0303(11) 0.0366(11) 0.0018(8) 0.0059(9) 0.0029(9) C8 0.0357(11) 0.0276(10) 0.0363(10) -0.0021(8) 0.0076(9) 0.0040(8) C9 0.0416(12) 0.0291(11) 0.0462(12) 0.0050(9) 0.0108(10) 0.0018(9) C10 0.0389(12) 0.0357(12) 0.0553(13) -0.0012(10) 0.0112(10) -0.0063(10) C11 0.0328(12) 0.0431(12) 0.0407(11) -0.0037(9) 0.0033(9) 0.0026(9) C12 0.0442(13) 0.0366(12) 0.0371(11) 0.0056(9) 0.0058(10) 0.0020(10) C13 0.0390(12) 0.0320(11) 0.0393(11) 0.0016(8) 0.0061(9) -0.0049(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1A C3A 1.325(4) . ? C1A C2A 1.388(3) . ? C1A C6A 1.389(3) . ? C1A C7 1.494(3) . ? C2A C3A 1.377(3) . ? C2A H2A 0.9300 . ? C3A C4A 1.374(4) . ? C4A C5A 1.365(4) . ? C4A H4A 0.9300 . ? C5A C6A 1.375(3) . ? C5A H5A 0.9300 . ? C6A H6A 0.9300 . ? Cl1 C11 1.738(2) . ? N1 C7 1.364(3) . ? N1 C8 1.409(3) . ? N1 H1 0.8600 . ? O1 C7 1.224(3) . ? C8 C9 1.388(3) . ? C8 C13 1.391(3) . ? C9 C10 1.380(3) . ? C9 H9 0.9300 . ? C10 C11 1.384(3) . ? C10 H10 0.9300 . ? C11 C12 1.375(3) . ? C12 C13 1.383(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? 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 C2A C1A C6A 119.3(2) . . ? C2A C1A C7 122.47(19) . . ? C6A C1A C7 118.15(19) . . ? C3A C2A C1A 119.0(2) . . ? C3A C2A H2A 120.5 . . ? C1A C2A H2A 120.5 . . ? F1A C3A C4A 118.8(3) . . ? F1A C3A C2A 119.1(3) . . ? C4A C3A C2A 122.1(2) . . ? C5A C4A C3A 118.1(2) . . ? C5A C4A H4A 121.0 . . ? C3A C4A H4A 121.0 . . ? C4A C5A C6A 121.8(2) . . ? C4A C5A H5A 119.1 . . ? C6A C5A H5A 119.1 . . ? C5A C6A C1A 119.7(2) . . ? C5A C6A H6A 120.2 . . ? C1A C6A H6A 120.2 . . ? C7 N1 C8 126.20(16) . . ? C7 N1 H1 116.9 . . ? C8 N1 H1 116.9 . . ? O1 C7 N1 122.7(2) . . ? O1 C7 C1A 121.48(19) . . ? N1 C7 C1A 115.79(17) . . ? C9 C8 C13 119.3(2) . . ? C9 C8 N1 118.74(18) . . ? C13 C8 N1 121.86(18) . . ? C10 C9 C8 120.66(19) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 119.3(2) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C12 C11 C10 120.8(2) . . ? C12 C11 Cl1 119.51(17) . . ? C10 C11 Cl1 119.65(18) . . ? C11 C12 C13 119.82(19) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C8 120.13(19) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A C1A C2A C3A -0.9(4) . . . . ? C7 C1A C2A C3A 176.7(2) . . . . ? C1A C2A C3A F1A -176.9(3) . . . . ? C1A C2A C3A C4A 2.3(4) . . . . ? F1A C3A C4A C5A 177.5(3) . . . . ? C2A C3A C4A C5A -1.7(4) . . . . ? C3A C4A C5A C6A -0.2(4) . . . . ? C4A C5A C6A C1A 1.5(4) . . . . ? C2A C1A C6A C5A -0.9(4) . . . . ? C7 C1A C6A C5A -178.6(2) . . . . ? C8 N1 C7 O1 5.2(3) . . . . ? C8 N1 C7 C1A -175.15(18) . . . . ? C2A C1A C7 O1 -147.8(2) . . . . ? C6A C1A C7 O1 29.8(3) . . . . ? C2A C1A C7 N1 32.6(3) . . . . ? C6A C1A C7 N1 -149.9(2) . . . . ? C7 N1 C8 C9 -149.1(2) . . . . ? C7 N1 C8 C13 35.0(3) . . . . ? C13 C8 C9 C10 0.3(3) . . . . ? N1 C8 C9 C10 -175.69(19) . . . . ? C8 C9 C10 C11 0.0(3) . . . . ? C9 C10 C11 C12 -0.4(3) . . . . ? C9 C10 C11 Cl1 178.35(17) . . . . ? C10 C11 C12 C13 0.5(3) . . . . ? Cl1 C11 C12 C13 -178.28(17) . . . . ? C11 C12 C13 C8 -0.2(3) . . . . ? C9 C8 C13 C12 -0.2(3) . . . . ? N1 C8 C13 C12 175.63(19) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.234 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.061 #============================================================================== data_3FA-2ClB _database_code_depnum_ccdc_archive 'CCDC 764629' #TrackingRef '- CIF.cif' #============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-chloro-N-(3-flourophenyl)benzamide ; _chemical_name_common 2-chloro-N-(3-flourophenyl)benzamide _chemical_formula_sum 'C13 H9 Cl F N O' _chemical_formula_weight 249.66 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.6468(3) _cell_length_b 12.3384(3) _cell_length_c 13.7313(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.686(2) _cell_angle_gamma 90.00 _cell_volume 2311.91(10) _cell_formula_units_Z 8 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 420 _cell_measurement_theta_min 0.97 _cell_measurement_theta_max 27.87 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.324 _exptl_absorpt_correction_T_min 0.9090 _exptl_absorpt_correction_T_max 0.9652 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23929 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4531 _reflns_number_gt 3056 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction SAINT _computing_structure_solution 'WinGX-Version 1.70.01(Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0696P)^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 4531 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 F1A F 0.49379(14) -0.21819(13) 0.33993(15) 0.0822(7) Uani 0.799(3) 1 d P A -1 F2A F 0.88336(16) 0.70320(14) 0.02843(13) 0.1098(9) Uani 0.924(4) 1 d P B -1 C8A C 0.55247(14) 0.04999(15) 0.25656(13) 0.0401(5) Uani 0.799(3) 1 d P A -1 C9A C 0.64631(15) 0.03074(17) 0.22402(14) 0.0490(5) Uani 0.799(3) 1 d P A -1 H9A H 0.6824 0.0867 0.1966 0.059 Uiso 0.799(3) 1 calc PR A -1 C10A C 0.68646(18) -0.07156(19) 0.23229(16) 0.0588(6) Uani 0.799(3) 1 d P A -1 H10A H 0.7498 -0.0834 0.2105 0.071 Uiso 0.799(3) 1 calc PR A -1 C11A C 0.63563(18) -0.15587(18) 0.27161(16) 0.0562(6) Uani 0.799(3) 1 d P A -1 H11A H 0.6629 -0.2247 0.2768 0.067 Uiso 0.799(3) 1 calc PR A -1 C12A C 0.54335(18) -0.13478(17) 0.30279(16) 0.0551(6) Uani 0.799(3) 1 d P A -1 C13A C 0.49931(15) -0.03428(16) 0.29657(15) 0.0491(5) Uani 0.799(3) 1 d P A -1 H13A H 0.4359 -0.0235 0.3186 0.059 Uiso 0.799(3) 1 calc PR A -1 C28A C 0.73253(16) 0.46529(16) 0.02139(13) 0.0459(5) Uani 0.924(4) 1 d P B -1 C29A C 0.81398(18) 0.53024(17) 0.01501(14) 0.0539(6) Uani 0.924(4) 1 d P B -1 H29A H 0.8744 0.5015 -0.0021 0.065 Uiso 0.924(4) 1 calc PR B -1 C30A C 0.8038(2) 0.6398(2) 0.03479(16) 0.0735(8) Uani 0.924(4) 1 d P B -1 C31A C 0.7172(3) 0.6851(2) 0.0596(2) 0.0996(12) Uani 0.924(4) 1 d P B -1 H31A H 0.7120 0.7589 0.0721 0.120 Uiso 0.924(4) 1 calc PR B -1 C32A C 0.6375(3) 0.6182(2) 0.0656(2) 0.1044(12) Uani 0.924(4) 1 d P B -1 H32A H 0.5771 0.6474 0.0821 0.125 Uiso 0.924(4) 1 calc PR B -1 C33A C 0.6445(2) 0.5093(2) 0.04795(18) 0.0745(8) Uani 0.924(4) 1 d P B -1 H33A H 0.5897 0.4652 0.0540 0.089 Uiso 0.924(4) 1 calc PR B -1 F1B F 0.7640(5) -0.0931(6) 0.2003(5) 0.074(3) Uani 0.201(3) 1 d P A -2 F2B F 0.578(2) 0.6660(17) 0.096(2) 0.151(16) Uani 0.076(4) 1 d P B -2 C8B C 0.55247(14) 0.04999(15) 0.25656(13) 0.0401(5) Uani 0.201(3) 1 d P A -2 C13B C 0.64631(15) 0.03074(17) 0.22402(14) 0.0490(5) Uani 0.201(3) 1 d P A -2 H13B H 0.6824 0.0867 0.1966 0.059 Uiso 0.201(3) 1 calc PR A -2 C12B C 0.68646(18) -0.07156(19) 0.23229(16) 0.0588(6) Uani 0.201(3) 1 d P A -2 C11B C 0.63563(18) -0.15587(18) 0.27161(16) 0.0562(6) Uani 0.201(3) 1 d P A -2 H11B H 0.6629 -0.2247 0.2768 0.067 Uiso 0.201(3) 1 calc PR A -2 C10B C 0.54335(18) -0.13478(17) 0.30279(16) 0.0551(6) Uani 0.201(3) 1 d P A -2 H10B H 0.5079 -0.1914 0.3299 0.066 Uiso 0.201(3) 1 calc PR A -2 C9B C 0.49931(15) -0.03428(16) 0.29657(15) 0.0491(5) Uani 0.201(3) 1 d P A -2 H9B H 0.4359 -0.0235 0.3186 0.059 Uiso 0.201(3) 1 calc PR A -2 C28B C 0.73253(16) 0.46529(16) 0.02139(13) 0.0459(5) Uani 0.076(4) 1 d P B -2 C33B C 0.81398(18) 0.53024(17) 0.01501(14) 0.0539(6) Uani 0.076(4) 1 d P B -2 H33B H 0.8744 0.5015 -0.0021 0.065 Uiso 0.076(4) 1 calc PR B -2 C32B C 0.8038(2) 0.6398(2) 0.03479(16) 0.0735(8) Uani 0.076(4) 1 d P B -2 H32B H 0.8587 0.6840 0.0309 0.088 Uiso 0.076(4) 1 calc PR B -2 C31B C 0.7172(3) 0.6851(2) 0.0596(2) 0.0996(12) Uani 0.076(4) 1 d P B -2 H31B H 0.7120 0.7589 0.0721 0.120 Uiso 0.076(4) 1 calc PR B -2 C30B C 0.6375(3) 0.6182(2) 0.0656(2) 0.1044(12) Uani 0.076(4) 1 d P B -2 C29B C 0.6445(2) 0.5093(2) 0.04795(18) 0.0745(8) Uani 0.076(4) 1 d P B -2 H29B H 0.5897 0.4652 0.0540 0.089 Uiso 0.076(4) 1 calc PR B -2 Cl1 Cl 0.23765(4) 0.28989(5) 0.22485(4) 0.0695(2) Uani 1 1 d . . . Cl2 Cl 0.53631(5) 0.13723(6) -0.05225(5) 0.0862(3) Uani 1 1 d . . . O2 O 0.63892(11) 0.28322(11) 0.10856(11) 0.0581(4) Uani 1 1 d . . . N1 N 0.51543(11) 0.15596(12) 0.24441(11) 0.0423(4) Uani 1 1 d . . . H1N H 0.5441 0.1952 0.2015 0.051 Uiso 1 1 calc R A . N2 N 0.74285(12) 0.35433(12) -0.00181(11) 0.0428(4) Uani 1 1 d . . . H2N H 0.7821 0.3382 -0.0481 0.051 Uiso 1 1 calc R B . O1 O 0.38741(11) 0.15506(11) 0.34776(11) 0.0617(4) Uani 1 1 d . . . C1 C 0.42987(14) 0.32166(15) 0.27138(13) 0.0399(5) Uani 1 1 d . . . C2 C 0.50990(15) 0.39039(16) 0.28366(16) 0.0512(5) Uani 1 1 d . A . H2 H 0.5697 0.3615 0.3040 0.061 Uiso 1 1 calc R . . C3 C 0.50278(17) 0.49978(18) 0.26655(17) 0.0600(6) Uani 1 1 d . . . H3 H 0.5570 0.5444 0.2762 0.072 Uiso 1 1 calc R A . C4 C 0.41567(19) 0.54283(18) 0.23523(16) 0.0596(6) Uani 1 1 d . A . H4 H 0.4113 0.6166 0.2222 0.072 Uiso 1 1 calc R . . C5 C 0.33456(17) 0.47815(18) 0.22283(15) 0.0539(6) Uani 1 1 d . . . H5 H 0.2754 0.5079 0.2019 0.065 Uiso 1 1 calc R A . C6 C 0.34174(14) 0.36825(16) 0.24184(13) 0.0432(5) Uani 1 1 d . A . C7 C 0.44052(14) 0.20353(16) 0.29170(14) 0.0415(5) Uani 1 1 d . A . C21 C 0.72413(14) 0.16137(15) 0.00558(13) 0.0399(5) Uani 1 1 d . . . C22 C 0.82008(16) 0.12387(17) 0.01652(15) 0.0540(6) Uani 1 1 d . B . H22 H 0.8683 0.1695 0.0418 0.065 Uiso 1 1 calc R . . C23 C 0.84375(19) 0.0193(2) -0.00998(17) 0.0651(7) Uani 1 1 d . . . H23 H 0.9075 -0.0060 -0.0013 0.078 Uiso 1 1 calc R B . C24 C 0.7730(2) -0.04723(18) -0.04907(17) 0.0653(7) Uani 1 1 d . B . H24 H 0.7895 -0.1176 -0.0667 0.078 Uiso 1 1 calc R . . C25 C 0.67857(19) -0.01198(18) -0.06265(16) 0.0617(6) Uani 1 1 d . . . H25 H 0.6314 -0.0571 -0.0905 0.074 Uiso 1 1 calc R B . C26 C 0.65479(16) 0.09300(17) -0.03386(14) 0.0492(5) Uani 1 1 d . B . C27 C 0.69672(14) 0.27169(15) 0.04208(13) 0.0402(5) Uani 1 1 d . B . 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 F1A 0.0758(13) 0.0409(11) 0.1301(16) 0.0178(10) 0.0064(11) -0.0032(9) F2A 0.154(2) 0.0618(12) 0.1129(15) -0.0004(9) -0.0104(13) -0.0453(12) C8A 0.0450(11) 0.0381(12) 0.0372(10) -0.0019(8) 0.0044(9) 0.0041(9) C9A 0.0451(12) 0.0563(14) 0.0458(11) 0.0032(10) 0.0114(9) 0.0057(10) C10A 0.0536(14) 0.0682(17) 0.0547(13) -0.0032(12) 0.0078(11) 0.0239(13) C11A 0.0653(15) 0.0488(14) 0.0544(12) -0.0022(11) -0.0042(11) 0.0195(12) C12A 0.0652(15) 0.0393(13) 0.0606(13) 0.0029(10) -0.0043(11) -0.0008(11) C13A 0.0439(12) 0.0428(13) 0.0607(13) -0.0009(10) 0.0076(10) -0.0001(10) C28A 0.0636(14) 0.0380(12) 0.0364(10) 0.0027(9) 0.0116(10) -0.0005(10) C29A 0.0757(16) 0.0431(13) 0.0429(11) 0.0019(10) 0.0026(11) -0.0040(12) C30A 0.124(3) 0.0485(16) 0.0477(13) 0.0057(11) 0.0042(15) -0.0210(17) C31A 0.187(4) 0.0422(16) 0.0710(17) 0.0030(13) 0.056(2) 0.015(2) C32A 0.145(3) 0.0529(19) 0.117(2) 0.0211(17) 0.079(2) 0.034(2) C33A 0.0838(19) 0.0484(15) 0.0923(19) 0.0110(13) 0.0398(16) 0.0127(13) F1B 0.044(4) 0.078(5) 0.102(5) 0.014(4) 0.029(4) 0.024(3) F2B 0.18(3) 0.064(16) 0.21(3) 0.042(16) 0.15(3) 0.062(16) C8B 0.0450(11) 0.0381(12) 0.0372(10) -0.0019(8) 0.0044(9) 0.0041(9) C13B 0.0451(12) 0.0563(14) 0.0458(11) 0.0032(10) 0.0114(9) 0.0057(10) C12B 0.0536(14) 0.0682(17) 0.0547(13) -0.0032(12) 0.0078(11) 0.0239(13) C11B 0.0653(15) 0.0488(14) 0.0544(12) -0.0022(11) -0.0042(11) 0.0195(12) C10B 0.0652(15) 0.0393(13) 0.0606(13) 0.0029(10) -0.0043(11) -0.0008(11) C9B 0.0439(12) 0.0428(13) 0.0607(13) -0.0009(10) 0.0076(10) -0.0001(10) C28B 0.0636(14) 0.0380(12) 0.0364(10) 0.0027(9) 0.0116(10) -0.0005(10) C33B 0.0757(16) 0.0431(13) 0.0429(11) 0.0019(10) 0.0026(11) -0.0040(12) C32B 0.124(3) 0.0485(16) 0.0477(13) 0.0057(11) 0.0042(15) -0.0210(17) C31B 0.187(4) 0.0422(16) 0.0710(17) 0.0030(13) 0.056(2) 0.015(2) C30B 0.145(3) 0.0529(19) 0.117(2) 0.0211(17) 0.079(2) 0.034(2) C29B 0.0838(19) 0.0484(15) 0.0923(19) 0.0110(13) 0.0398(16) 0.0127(13) Cl1 0.0518(4) 0.0745(5) 0.0819(4) -0.0064(3) -0.0105(3) -0.0108(3) Cl2 0.0584(4) 0.0947(6) 0.1051(5) -0.0172(4) -0.0190(4) -0.0004(4) O2 0.0697(10) 0.0455(9) 0.0600(9) -0.0032(7) 0.0342(8) -0.0045(7) N1 0.0419(9) 0.0379(10) 0.0476(9) 0.0028(7) 0.0174(8) 0.0036(7) N2 0.0506(10) 0.0370(10) 0.0413(8) -0.0023(7) 0.0172(7) 0.0007(8) O1 0.0611(10) 0.0476(9) 0.0774(10) 0.0114(8) 0.0396(8) 0.0043(7) C1 0.0417(11) 0.0383(11) 0.0400(10) -0.0020(8) 0.0139(9) 0.0012(9) C2 0.0386(11) 0.0459(13) 0.0695(14) -0.0025(11) 0.0113(10) 0.0012(10) C3 0.0572(15) 0.0465(14) 0.0766(16) -0.0078(12) 0.0174(12) -0.0114(11) C4 0.0794(17) 0.0359(12) 0.0639(14) 0.0022(10) 0.0176(13) 0.0056(12) C5 0.0622(15) 0.0498(14) 0.0497(12) 0.0003(10) 0.0013(11) 0.0125(11) C6 0.0438(12) 0.0489(13) 0.0372(10) -0.0041(9) 0.0052(9) -0.0018(9) C7 0.0398(11) 0.0405(12) 0.0444(10) 0.0007(9) 0.0113(9) -0.0002(9) C21 0.0458(12) 0.0391(11) 0.0350(9) 0.0006(8) 0.0099(9) -0.0023(9) C22 0.0566(14) 0.0519(14) 0.0537(12) -0.0029(10) 0.0094(10) 0.0052(11) C23 0.0631(16) 0.0657(17) 0.0668(15) 0.0048(13) 0.0157(13) 0.0185(13) C24 0.099(2) 0.0412(13) 0.0567(13) 0.0000(11) 0.0252(14) 0.0098(14) C25 0.0824(18) 0.0464(14) 0.0565(13) -0.0098(11) 0.0099(13) -0.0138(13) C26 0.0548(13) 0.0478(13) 0.0452(11) -0.0011(10) 0.0036(10) -0.0036(10) C27 0.0416(11) 0.0399(12) 0.0393(10) -0.0011(9) 0.0077(9) -0.0020(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1A C12A 1.336(3) . ? F2A C30A 1.342(3) . ? C8A C9A 1.382(3) . ? C8A C13A 1.385(3) . ? C8A N1 1.411(2) . ? C9A C10A 1.380(3) . ? C9A H9A 0.9300 . ? C10A C11A 1.365(3) . ? C10A H10A 0.9300 . ? C11A C12A 1.360(3) . ? C11A H11A 0.9300 . ? C12A C13A 1.380(3) . ? C13A H13A 0.9300 . ? C28A C33A 1.371(3) . ? C28A C29A 1.374(3) . ? C28A N2 1.413(2) . ? C29A C30A 1.386(3) . ? C29A H29A 0.9300 . ? C30A C31A 1.355(4) . ? C31A C32A 1.368(5) . ? C31A H31A 0.9300 . ? C32A C33A 1.369(4) . ? C32A H32A 0.9300 . ? C33A H33A 0.9300 . ? Cl1 C6 1.732(2) . ? Cl2 C26 1.722(2) . ? O2 C27 1.222(2) . ? N1 C7 1.352(2) . ? N1 H1N 0.8600 . ? N2 C27 1.345(2) . ? N2 H2N 0.8600 . ? O1 C7 1.220(2) . ? C1 C6 1.389(3) . ? C1 C2 1.391(3) . ? C1 C7 1.491(3) . ? C2 C3 1.373(3) . ? C2 H2 0.9300 . ? C3 C4 1.367(3) . ? C3 H3 0.9300 . ? C4 C5 1.374(3) . ? C4 H4 0.9300 . ? C5 C6 1.384(3) . ? C5 H5 0.9300 . ? C21 C26 1.374(3) . ? C21 C22 1.395(3) . ? C21 C27 1.500(3) . ? C22 C23 1.380(3) . ? C22 H22 0.9300 . ? C23 C24 1.371(3) . ? C23 H23 0.9300 . ? C24 C25 1.371(3) . ? C24 H24 0.9300 . ? C25 C26 1.394(3) . ? C25 H25 0.9300 . ? 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 C9A C8A C13A 119.41(18) . . ? C9A C8A N1 116.94(17) . . ? C13A C8A N1 123.64(18) . . ? C10A C9A C8A 119.9(2) . . ? C10A C9A H9A 120.0 . . ? C8A C9A H9A 120.0 . . ? C11A C10A C9A 121.8(2) . . ? C11A C10A H10A 119.1 . . ? C9A C10A H10A 119.1 . . ? C12A C11A C10A 117.1(2) . . ? C12A C11A H11A 121.5 . . ? C10A C11A H11A 121.5 . . ? F1A C12A C11A 116.6(2) . . ? F1A C12A C13A 119.6(2) . . ? C11A C12A C13A 123.8(2) . . ? C12A C13A C8A 118.0(2) . . ? C12A C13A H13A 121.0 . . ? C8A C13A H13A 121.0 . . ? C33A C28A C29A 119.8(2) . . ? C33A C28A N2 122.3(2) . . ? C29A C28A N2 117.89(19) . . ? C28A C29A C30A 118.2(2) . . ? C28A C29A H29A 120.9 . . ? C30A C29A H29A 120.9 . . ? F2A C30A C31A 119.0(3) . . ? F2A C30A C29A 118.2(3) . . ? C31A C30A C29A 122.8(3) . . ? C30A C31A C32A 117.5(3) . . ? C30A C31A H31A 121.2 . . ? C32A C31A H31A 121.2 . . ? C31A C32A C33A 121.6(3) . . ? C31A C32A H32A 119.2 . . ? C33A C32A H32A 119.2 . . ? C32A C33A C28A 119.9(3) . . ? C32A C33A H33A 120.0 . . ? C28A C33A H33A 120.0 . . ? C7 N1 C8A 128.13(16) . . ? C7 N1 H1N 115.9 . . ? C8A N1 H1N 115.9 . . ? C27 N2 C28A 125.81(16) . . ? C27 N2 H2N 117.1 . . ? C28A N2 H2N 117.1 . . ? C6 C1 C2 117.31(18) . . ? C6 C1 C7 122.77(18) . . ? C2 C1 C7 119.91(18) . . ? C3 C2 C1 121.6(2) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C4 C3 C2 119.7(2) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.7(2) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 119.4(2) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C1 121.30(19) . . ? C5 C6 Cl1 117.74(16) . . ? C1 C6 Cl1 120.95(16) . . ? O1 C7 N1 123.27(18) . . ? O1 C7 C1 122.69(17) . . ? N1 C7 C1 114.03(16) . . ? C26 C21 C22 118.68(19) . . ? C26 C21 C27 121.04(18) . . ? C22 C21 C27 120.17(18) . . ? C23 C22 C21 120.3(2) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C24 C23 C22 119.8(2) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C25 121.3(2) . . ? C23 C24 H24 119.4 . . ? C25 C24 H24 119.4 . . ? C24 C25 C26 118.5(2) . . ? C24 C25 H25 120.7 . . ? C26 C25 H25 120.7 . . ? C21 C26 C25 121.4(2) . . ? C21 C26 Cl2 120.28(16) . . ? C25 C26 Cl2 118.31(18) . . ? O2 C27 N2 123.81(17) . . ? O2 C27 C21 121.41(16) . . ? N2 C27 C21 114.74(16) . . ? 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 C13A C8A C9A C10A -0.5(3) . . . . ? N1 C8A C9A C10A -179.00(18) . . . . ? C8A C9A C10A C11A 0.4(3) . . . . ? C9A C10A C11A C12A -0.2(3) . . . . ? C10A C11A C12A F1A 179.1(2) . . . . ? C10A C11A C12A C13A 0.1(3) . . . . ? F1A C12A C13A C8A -179.2(2) . . . . ? C11A C12A C13A C8A -0.3(3) . . . . ? C9A C8A C13A C12A 0.4(3) . . . . ? N1 C8A C13A C12A 178.81(18) . . . . ? C33A C28A C29A C30A -0.8(3) . . . . ? N2 C28A C29A C30A 178.08(18) . . . . ? C28A C29A C30A F2A -179.92(19) . . . . ? C28A C29A C30A C31A -0.3(3) . . . . ? F2A C30A C31A C32A -179.9(3) . . . . ? C29A C30A C31A C32A 0.5(4) . . . . ? C30A C31A C32A C33A 0.4(5) . . . . ? C31A C32A C33A C28A -1.5(5) . . . . ? C29A C28A C33A C32A 1.7(4) . . . . ? N2 C28A C33A C32A -177.2(2) . . . . ? C9A C8A N1 C7 -160.09(19) . . . . ? C13A C8A N1 C7 21.5(3) . . . . ? C33A C28A N2 C27 -37.1(3) . . . . ? C29A C28A N2 C27 144.09(19) . . . . ? C6 C1 C2 C3 -0.6(3) . . . . ? C7 C1 C2 C3 -179.40(18) . . . . ? C1 C2 C3 C4 -1.0(3) . . . . ? C2 C3 C4 C5 1.5(3) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C4 C5 C6 C1 -1.3(3) . . . . ? C4 C5 C6 Cl1 -179.82(16) . . . . ? C2 C1 C6 C5 1.7(3) . . . . ? C7 C1 C6 C5 -179.49(17) . . . . ? C2 C1 C6 Cl1 -179.78(14) . . . . ? C7 C1 C6 Cl1 -1.0(2) . . . . ? C8A N1 C7 O1 -6.9(3) . . . . ? C8A N1 C7 C1 171.58(18) . . . . ? C6 C1 C7 O1 -53.2(3) . . . . ? C2 C1 C7 O1 125.6(2) . . . . ? C6 C1 C7 N1 128.31(19) . . . . ? C2 C1 C7 N1 -52.9(2) . . . . ? C26 C21 C22 C23 -1.4(3) . . . . ? C27 C21 C22 C23 174.87(18) . . . . ? C21 C22 C23 C24 1.4(3) . . . . ? C22 C23 C24 C25 0.0(3) . . . . ? C23 C24 C25 C26 -1.3(3) . . . . ? C22 C21 C26 C25 0.1(3) . . . . ? C27 C21 C26 C25 -176.16(18) . . . . ? C22 C21 C26 Cl2 -177.96(15) . . . . ? C27 C21 C26 Cl2 5.8(3) . . . . ? C24 C25 C26 C21 1.3(3) . . . . ? C24 C25 C26 Cl2 179.35(16) . . . . ? C28A N2 C27 O2 0.2(3) . . . . ? C28A N2 C27 C21 -177.71(18) . . . . ? C26 C21 C27 O2 61.4(3) . . . . ? C22 C21 C27 O2 -114.8(2) . . . . ? C26 C21 C27 N2 -120.7(2) . . . . ? C22 C21 C27 N2 63.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.504 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.051 #============================================================================== data_3FA-2IB _database_code_depnum_ccdc_archive 'CCDC 774717' #TrackingRef '- CIF.cif' #============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-iodo-N-(3-fluorophenyl)benzamide ; _chemical_name_common 2-iodo-N-(3-fluorophenyl)benzamide _chemical_formula_moiety 'C13 H9 F I N O' _chemical_formula_sum 'C13 H9 F I N O' _chemical_formula_weight 341.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.1012(3) _cell_length_b 11.0188(7) _cell_length_c 12.4410(8) _cell_angle_alpha 64.411(3) _cell_angle_beta 79.243(3) _cell_angle_gamma 87.180(3) _cell_volume 619.23(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 430 _cell_measurement_theta_min 0.79 _cell_measurement_theta_max 27.89 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.829 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 2.580 _exptl_absorpt_correction_T_min 0.6264 _exptl_absorpt_correction_T_max 0.7824 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 6993 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2143 _reflns_number_gt 1946 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction SAINT _computing_structure_solution 'WinGX-Version 1.70.01(Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0197P)^2^+0.6168P] 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 0.0160(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2143 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0295 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0561 _refine_ls_wR_factor_gt 0.0544 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 F1A F 0.8260(6) 0.5649(3) 0.9048(2) 0.0794(12) Uani 0.819(7) 1 d P A -1 C8A C 0.6225(6) 0.7106(3) 0.6162(3) 0.0443(8) Uani 0.819(7) 1 d P A -1 C9A C 0.4101(7) 0.7834(4) 0.6420(3) 0.0577(9) Uani 0.819(7) 1 d P A -1 H9A H 0.3118 0.8344 0.5827 0.069 Uiso 0.819(7) 1 calc PR A -1 C10A C 0.3457(9) 0.7798(5) 0.7559(4) 0.0702(11) Uani 0.819(7) 1 d P A -1 H10A H 0.2042 0.8296 0.7721 0.084 Uiso 0.819(7) 1 calc PR A -1 C11A C 0.4839(8) 0.7049(5) 0.8458(4) 0.0671(11) Uani 0.819(7) 1 d P A -1 H11A H 0.4374 0.7017 0.9229 0.081 Uiso 0.819(7) 1 calc PR A -1 C12A C 0.6916(8) 0.6355(4) 0.8180(3) 0.0600(10) Uani 0.819(7) 1 d P A -1 C13A C 0.7670(7) 0.6354(4) 0.7054(3) 0.0512(8) Uani 0.819(7) 1 d P A -1 H13A H 0.9106 0.5862 0.6900 0.061 Uiso 0.819(7) 1 calc PR A -1 F1B F 0.195(3) 0.8373(17) 0.7895(15) 0.097(6) Uani 0.181(7) 1 d P A -2 C8B C 0.6225(6) 0.7106(3) 0.6162(3) 0.0443(8) Uani 0.181(7) 1 d P A -2 C13B C 0.4101(7) 0.7834(4) 0.6420(3) 0.0577(9) Uani 0.181(7) 1 d P A -2 H13B H 0.3118 0.8344 0.5827 0.069 Uiso 0.181(7) 1 calc PR A -2 C12B C 0.3457(9) 0.7798(5) 0.7559(4) 0.0702(11) Uani 0.181(7) 1 d P A -2 C11B C 0.4839(8) 0.7049(5) 0.8458(4) 0.0671(11) Uani 0.181(7) 1 d P A -2 H11B H 0.4374 0.7017 0.9229 0.081 Uiso 0.181(7) 1 calc PR A -2 C10B C 0.6916(8) 0.6355(4) 0.8180(3) 0.0600(10) Uani 0.181(7) 1 d P A -2 H10B H 0.7889 0.5852 0.8780 0.072 Uiso 0.181(7) 1 calc PR A -2 C9B C 0.7670(7) 0.6354(4) 0.7054(3) 0.0512(8) Uani 0.181(7) 1 d P A -2 H9B H 0.9106 0.5862 0.6900 0.061 Uiso 0.181(7) 1 calc PR A -2 I1 I 1.30750(5) 0.95546(2) 0.22186(2) 0.05737(13) Uani 1 1 d . . . N1 N 0.6761(5) 0.7141(3) 0.4994(2) 0.0449(6) Uani 1 1 d . . . H1 H 0.5417 0.7250 0.4638 0.054 Uiso 1 1 calc R A . O1 O 1.1209(4) 0.6808(3) 0.4783(2) 0.0596(7) Uani 1 1 d . . . C1 C 0.9100(5) 0.7167(3) 0.3125(3) 0.0358(6) Uani 1 1 d . . . C2 C 1.0726(6) 0.8121(3) 0.2106(3) 0.0382(7) Uani 1 1 d . A . C3 C 1.0689(7) 0.8197(4) 0.0971(3) 0.0511(8) Uani 1 1 d . . . H3 H 1.1786 0.8830 0.0293 0.061 Uiso 1 1 calc R A . C4 C 0.9031(7) 0.7339(4) 0.0842(3) 0.0568(9) Uani 1 1 d . A . H4 H 0.9021 0.7393 0.0076 0.068 Uiso 1 1 calc R . . C5 C 0.7409(7) 0.6414(4) 0.1825(3) 0.0558(9) Uani 1 1 d . . . H5 H 0.6285 0.5843 0.1729 0.067 Uiso 1 1 calc R A . C6 C 0.7432(7) 0.6324(3) 0.2967(3) 0.0482(8) Uani 1 1 d . A . H6 H 0.6316 0.5690 0.3636 0.058 Uiso 1 1 calc R . . C7 C 0.9157(6) 0.7023(3) 0.4375(3) 0.0401(7) Uani 1 1 d . A . 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 F1A 0.102(2) 0.092(2) 0.0380(16) -0.0202(15) -0.0206(14) 0.0079(17) C8A 0.0331(16) 0.064(2) 0.0391(18) -0.0269(16) 0.0003(13) -0.0131(15) C9A 0.0446(19) 0.079(3) 0.061(2) -0.042(2) -0.0071(17) -0.0009(18) C10A 0.062(2) 0.091(3) 0.076(3) -0.059(3) 0.006(2) -0.014(2) C11A 0.066(3) 0.091(3) 0.056(2) -0.047(2) 0.009(2) -0.028(2) C12A 0.063(2) 0.072(2) 0.040(2) -0.0202(19) -0.0019(18) -0.027(2) C13A 0.0445(19) 0.069(2) 0.0381(19) -0.0225(17) -0.0022(15) -0.0061(16) F1B 0.085(10) 0.129(14) 0.101(12) -0.082(11) 0.003(8) 0.024(9) C8B 0.0331(16) 0.064(2) 0.0391(18) -0.0269(16) 0.0003(13) -0.0131(15) C13B 0.0446(19) 0.079(3) 0.061(2) -0.042(2) -0.0071(17) -0.0009(18) C12B 0.062(2) 0.091(3) 0.076(3) -0.059(3) 0.006(2) -0.014(2) C11B 0.066(3) 0.091(3) 0.056(2) -0.047(2) 0.009(2) -0.028(2) C10B 0.063(2) 0.072(2) 0.040(2) -0.0202(19) -0.0019(18) -0.027(2) C9B 0.0445(19) 0.069(2) 0.0381(19) -0.0225(17) -0.0022(15) -0.0061(16) I1 0.05467(17) 0.05121(17) 0.06137(19) -0.01833(12) -0.01074(11) -0.01172(10) N1 0.0289(13) 0.0732(19) 0.0361(14) -0.0260(14) -0.0082(11) 0.0009(12) O1 0.0290(11) 0.105(2) 0.0405(13) -0.0266(13) -0.0083(10) -0.0004(12) C1 0.0297(14) 0.0427(16) 0.0343(16) -0.0153(13) -0.0074(12) 0.0026(12) C2 0.0336(15) 0.0412(16) 0.0370(17) -0.0145(14) -0.0065(13) 0.0035(13) C3 0.051(2) 0.057(2) 0.0364(18) -0.0150(16) -0.0004(15) -0.0014(16) C4 0.064(2) 0.070(2) 0.044(2) -0.0313(19) -0.0102(17) 0.0003(19) C5 0.061(2) 0.061(2) 0.053(2) -0.0309(19) -0.0124(18) -0.0066(18) C6 0.0457(18) 0.0506(19) 0.0431(19) -0.0155(16) -0.0049(15) -0.0092(15) C7 0.0299(16) 0.0524(18) 0.0341(17) -0.0151(14) -0.0038(13) -0.0063(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1A C12A 1.319(5) . ? C8A C13A 1.382(5) . ? C8A C9A 1.389(5) . ? C8A N1 1.411(4) . ? C9A C10A 1.376(5) . ? C9A H9A 0.9300 . ? C10A C11A 1.367(6) . ? C10A H10A 0.9300 . ? C11A C12A 1.356(6) . ? C11A H11A 0.9300 . ? C12A C13A 1.382(5) . ? C13A H13A 0.9300 . ? I1 C2 2.095(3) . ? N1 C7 1.350(4) . ? N1 H1 0.8600 . ? O1 C7 1.216(3) . ? C1 C6 1.388(4) . ? C1 C2 1.394(4) . ? C1 C7 1.499(4) . ? C2 C3 1.382(4) . ? C3 C4 1.377(5) . ? C3 H3 0.9300 . ? C4 C5 1.359(5) . ? C4 H4 0.9300 . ? C5 C6 1.383(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? 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 C13A C8A C9A 119.5(3) . . ? C13A C8A N1 122.8(3) . . ? C9A C8A N1 117.7(3) . . ? C10A C9A C8A 119.7(4) . . ? C10A C9A H9A 120.1 . . ? C8A C9A H9A 120.1 . . ? C11A C10A C9A 121.8(4) . . ? C11A C10A H10A 119.1 . . ? C9A C10A H10A 119.1 . . ? C12A C11A C10A 117.3(4) . . ? C12A C11A H11A 121.3 . . ? C10A C11A H11A 121.3 . . ? F1A C12A C11A 116.9(4) . . ? F1A C12A C13A 119.4(4) . . ? C11A C12A C13A 123.7(4) . . ? C8A C13A C12A 118.0(3) . . ? C8A C13A H13A 121.0 . . ? C12A C13A H13A 121.0 . . ? C7 N1 C8A 127.0(2) . . ? C7 N1 H1 116.5 . . ? C8A N1 H1 116.5 . . ? C6 C1 C2 118.5(3) . . ? C6 C1 C7 119.9(3) . . ? C2 C1 C7 121.5(3) . . ? C3 C2 C1 120.1(3) . . ? C3 C2 I1 118.0(2) . . ? C1 C2 I1 121.8(2) . . ? C4 C3 C2 120.1(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 120.5(3) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 119.9(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 120.8(3) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? O1 C7 N1 123.8(3) . . ? O1 C7 C1 121.8(3) . . ? N1 C7 C1 114.4(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 C13A C8A C9A C10A -0.1(5) . . . . ? N1 C8A C9A C10A 178.1(3) . . . . ? C8A C9A C10A C11A -0.6(6) . . . . ? C9A C10A C11A C12A 1.1(6) . . . . ? C10A C11A C12A F1A 179.2(4) . . . . ? C10A C11A C12A C13A -0.9(6) . . . . ? C9A C8A C13A C12A 0.3(5) . . . . ? N1 C8A C13A C12A -177.8(3) . . . . ? F1A C12A C13A C8A -179.9(3) . . . . ? C11A C12A C13A C8A 0.2(6) . . . . ? C13A C8A N1 C7 -31.5(5) . . . . ? C9A C8A N1 C7 150.4(3) . . . . ? C6 C1 C2 C3 -1.1(4) . . . . ? C7 C1 C2 C3 177.8(3) . . . . ? C6 C1 C2 I1 174.6(2) . . . . ? C7 C1 C2 I1 -6.5(4) . . . . ? C1 C2 C3 C4 0.5(5) . . . . ? I1 C2 C3 C4 -175.3(3) . . . . ? C2 C3 C4 C5 0.3(5) . . . . ? C3 C4 C5 C6 -0.5(6) . . . . ? C4 C5 C6 C1 -0.1(5) . . . . ? C2 C1 C6 C5 0.9(5) . . . . ? C7 C1 C6 C5 -178.0(3) . . . . ? C8A N1 C7 O1 3.2(5) . . . . ? C8A N1 C7 C1 -177.2(3) . . . . ? C6 C1 C7 O1 122.5(4) . . . . ? C2 C1 C7 O1 -56.4(4) . . . . ? C6 C1 C7 N1 -57.0(4) . . . . ? C2 C1 C7 N1 124.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.549 _refine_diff_density_min -0.483 _refine_diff_density_rms 0.061 #========================================================================== data_2FB-2IA _database_code_depnum_ccdc_archive 'CCDC 774718' #TrackingRef '- CIF.cif' #========================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-fluoro-N-(2-iodophenyl)benzamide ; _chemical_name_common 2-fluoro-N-(2-iodophenyl)benzamide _chemical_formula_moiety 'C13 H9 F I N O' _chemical_formula_sum 'C13 H9 F I N O' _chemical_formula_weight 341.11 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_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.5468(11) _cell_length_b 4.7669(5) _cell_length_c 21.940(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.302(5) _cell_angle_gamma 90.00 _cell_volume 1206.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 376 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.86 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.878 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 2.648 _exptl_absorpt_correction_T_min 0.5038 _exptl_absorpt_correction_T_max 0.5934 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24409 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2372 _reflns_number_gt 2034 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction SAINT _computing_structure_solution 'WinGX-Version 1.70.01(Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0181P)^2^+0.9899P] 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 2372 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0304 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0491 _refine_ls_wR_factor_gt 0.0471 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 F1A F 0.1968(3) 0.2698(7) 0.21043(13) 0.0712(12) Uani 0.625(5) 1 d P A -1 C1A C 0.0326(2) -0.0115(5) 0.18697(12) 0.0381(6) Uani 0.625(5) 1 d P A -1 C2A C 0.0926(3) 0.1803(6) 0.22376(13) 0.0507(7) Uani 0.625(5) 1 d P A -1 C3A C 0.0490(4) 0.2808(7) 0.27678(14) 0.0645(9) Uani 0.625(5) 1 d P A -1 H3A H 0.0911 0.4098 0.3005 0.077 Uiso 0.625(5) 1 calc PR A -1 C4A C -0.0570(4) 0.1899(8) 0.29455(15) 0.0682(10) Uani 0.625(5) 1 d P A -1 H4A H -0.0875 0.2590 0.3302 0.082 Uiso 0.625(5) 1 calc PR A -1 C5A C -0.1183(3) -0.0026(8) 0.25989(15) 0.0624(9) Uani 0.625(5) 1 d P A -1 H5A H -0.1901 -0.0651 0.2721 0.075 Uiso 0.625(5) 1 calc PR A -1 C6A C -0.0735(3) -0.1032(6) 0.20706(14) 0.0512(7) Uani 0.625(5) 1 d P A -1 H6A H -0.1152 -0.2360 0.1842 0.061 Uiso 0.625(5) 1 calc PR A -1 F1B F -0.1383(4) -0.2826(11) 0.1759(2) 0.070(2) Uani 0.375(5) 1 d P A -2 C1B C 0.0326(2) -0.0115(5) 0.18697(12) 0.0381(6) Uani 0.375(5) 1 d P A -2 C6B C 0.0926(3) 0.1803(6) 0.22376(13) 0.0507(7) Uani 0.375(5) 1 d P A -2 H6B H 0.1648 0.2429 0.2121 0.061 Uiso 0.375(5) 1 calc PR A -2 C5B C 0.0490(4) 0.2808(7) 0.27678(14) 0.0645(9) Uani 0.375(5) 1 d P A -2 H5B H 0.0911 0.4098 0.3005 0.077 Uiso 0.375(5) 1 calc PR A -2 C4B C -0.0570(4) 0.1899(8) 0.29455(15) 0.0682(10) Uani 0.375(5) 1 d P A -2 H4B H -0.0875 0.2590 0.3302 0.082 Uiso 0.375(5) 1 calc PR A -2 C3B C -0.1183(3) -0.0026(8) 0.25989(15) 0.0624(9) Uani 0.375(5) 1 d P A -2 H3B H -0.1901 -0.0651 0.2721 0.075 Uiso 0.375(5) 1 calc PR A -2 C2B C -0.0735(3) -0.1032(6) 0.20706(14) 0.0512(7) Uani 0.375(5) 1 d P A -2 I1 I 0.379236(16) 0.36564(4) 0.085964(9) 0.05124(8) Uani 1 1 d . . . N1 N 0.13288(19) 0.0530(4) 0.09385(10) 0.0402(5) Uani 1 1 d . A . H1 H 0.1388 0.2232 0.1066 0.048 Uiso 1 1 calc R . . O1 O 0.06063(19) -0.3753(4) 0.11558(10) 0.0573(6) Uani 1 1 d . A . C7 C 0.0771(2) -0.1295(5) 0.12904(12) 0.0379(6) Uani 1 1 d . . . C8 C 0.1826(2) -0.0111(5) 0.03767(12) 0.0362(6) Uani 1 1 d . . . C9 C 0.2879(2) 0.1090(5) 0.02298(12) 0.0387(6) Uani 1 1 d . A . C10 C 0.3364(3) 0.0512(7) -0.03236(13) 0.0521(7) Uani 1 1 d . . . H10 H 0.4062 0.1340 -0.0421 0.062 Uiso 1 1 calc R A . C11 C 0.2811(3) -0.1291(7) -0.07299(14) 0.0588(8) Uani 1 1 d . A . H11 H 0.3144 -0.1700 -0.1098 0.071 Uiso 1 1 calc R . . C12 C 0.1773(3) -0.2487(7) -0.05956(14) 0.0538(8) Uani 1 1 d . . . H12 H 0.1403 -0.3698 -0.0873 0.065 Uiso 1 1 calc R A . C13 C 0.1275(2) -0.1894(6) -0.00470(13) 0.0448(7) Uani 1 1 d . A . H13 H 0.0566 -0.2692 0.0040 0.054 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 F1A 0.068(2) 0.086(2) 0.0586(19) -0.0154(16) -0.0008(15) -0.0283(17) C1A 0.0469(15) 0.0276(13) 0.0398(15) 0.0013(11) 0.0035(12) 0.0054(11) C2A 0.0626(19) 0.0436(18) 0.0455(17) 0.0011(13) -0.0029(14) 0.0012(14) C3A 0.098(3) 0.053(2) 0.0413(18) -0.0084(15) -0.0066(18) 0.0051(19) C4A 0.100(3) 0.065(2) 0.0403(18) 0.0007(16) 0.0154(18) 0.030(2) C5A 0.064(2) 0.069(2) 0.056(2) 0.0030(18) 0.0221(17) 0.0135(18) C6A 0.0549(17) 0.0486(18) 0.0506(18) -0.0013(15) 0.0091(14) 0.0037(14) F1B 0.062(3) 0.083(4) 0.066(3) -0.021(3) 0.018(3) -0.028(3) C1B 0.0469(15) 0.0276(13) 0.0398(15) 0.0013(11) 0.0035(12) 0.0054(11) C6B 0.0626(19) 0.0436(18) 0.0455(17) 0.0011(13) -0.0029(14) 0.0012(14) C5B 0.098(3) 0.053(2) 0.0413(18) -0.0084(15) -0.0066(18) 0.0051(19) C4B 0.100(3) 0.065(2) 0.0403(18) 0.0007(16) 0.0154(18) 0.030(2) C3B 0.064(2) 0.069(2) 0.056(2) 0.0030(18) 0.0221(17) 0.0135(18) C2B 0.0549(17) 0.0486(18) 0.0506(18) -0.0013(15) 0.0091(14) 0.0037(14) I1 0.04755(12) 0.04725(12) 0.05833(14) 0.00077(10) -0.00518(8) -0.01004(9) N1 0.0507(13) 0.0276(11) 0.0429(13) -0.0081(9) 0.0111(10) -0.0057(9) O1 0.0828(15) 0.0262(11) 0.0645(13) -0.0067(9) 0.0226(11) -0.0061(10) C7 0.0394(14) 0.0278(14) 0.0469(15) -0.0026(12) 0.0059(11) 0.0028(11) C8 0.0409(14) 0.0271(13) 0.0407(15) 0.0008(11) 0.0032(12) 0.0034(11) C9 0.0411(14) 0.0353(14) 0.0396(15) 0.0031(12) -0.0005(11) 0.0008(11) C10 0.0511(17) 0.0565(19) 0.0491(18) 0.0053(15) 0.0085(14) -0.0028(14) C11 0.067(2) 0.069(2) 0.0408(17) -0.0045(16) 0.0135(15) 0.0024(17) C12 0.066(2) 0.0508(17) 0.0441(18) -0.0117(14) -0.0047(15) 0.0014(15) C13 0.0450(15) 0.0391(16) 0.0503(17) -0.0056(13) 0.0029(13) -0.0024(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1A C2A 1.320(4) . ? C1A C2A 1.387(4) . ? C1A C6A 1.388(4) . ? C1A C7 1.499(4) . ? C2A C3A 1.372(4) . ? C3A C4A 1.370(5) . ? C3A H3A 0.9300 . ? C4A C5A 1.370(5) . ? C4A H4A 0.9300 . ? C5A C6A 1.375(4) . ? C5A H5A 0.9300 . ? C6A H6A 0.9300 . ? I1 C9 2.098(3) . ? N1 C7 1.345(3) . ? N1 C8 1.414(3) . ? N1 H1 0.8600 . ? O1 C7 1.222(3) . ? C8 C9 1.394(4) . ? C8 C13 1.394(4) . ? C9 C10 1.385(4) . ? C10 C11 1.377(4) . ? C10 H10 0.9300 . ? C11 C12 1.369(4) . ? C11 H11 0.9300 . ? C12 C13 1.384(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? 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 C2A C1A C6A 116.7(3) . . ? C2A C1A C7 124.1(2) . . ? C6A C1A C7 119.2(2) . . ? F1A C2A C3A 116.4(3) . . ? F1A C2A C1A 121.5(3) . . ? C3A C2A C1A 122.1(3) . . ? C4A C3A C2A 119.6(3) . . ? C4A C3A H3A 120.2 . . ? C2A C3A H3A 120.2 . . ? C3A C4A C5A 120.1(3) . . ? C3A C4A H4A 120.0 . . ? C5A C4A H4A 120.0 . . ? C4A C5A C6A 119.9(3) . . ? C4A C5A H5A 120.1 . . ? C6A C5A H5A 120.1 . . ? C5A C6A C1A 121.7(3) . . ? C5A C6A H6A 119.2 . . ? C1A C6A H6A 119.2 . . ? C7 N1 C8 125.5(2) . . ? C7 N1 H1 117.2 . . ? C8 N1 H1 117.2 . . ? O1 C7 N1 123.7(2) . . ? O1 C7 C1A 120.6(2) . . ? N1 C7 C1A 115.6(2) . . ? C9 C8 C13 118.4(2) . . ? C9 C8 N1 120.1(2) . . ? C13 C8 N1 121.5(2) . . ? C10 C9 C8 120.6(2) . . ? C10 C9 I1 118.9(2) . . ? C8 C9 I1 120.50(19) . . ? C11 C10 C9 119.9(3) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 120.0(3) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C8 120.7(3) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A C1A C2A F1A 176.5(3) . . . . ? C7 C1A C2A F1A -1.4(5) . . . . ? C6A C1A C2A C3A -1.5(4) . . . . ? C7 C1A C2A C3A -179.4(3) . . . . ? F1A C2A C3A C4A -177.9(3) . . . . ? C1A C2A C3A C4A 0.2(5) . . . . ? C2A C3A C4A C5A 0.8(5) . . . . ? C3A C4A C5A C6A -0.4(5) . . . . ? C4A C5A C6A C1A -1.0(5) . . . . ? C2A C1A C6A C5A 1.9(4) . . . . ? C7 C1A C6A C5A 179.9(3) . . . . ? C8 N1 C7 O1 -1.6(4) . . . . ? C8 N1 C7 C1A 179.6(2) . . . . ? C2A C1A C7 O1 141.4(3) . . . . ? C6A C1A C7 O1 -36.4(4) . . . . ? C2A C1A C7 N1 -39.7(4) . . . . ? C6A C1A C7 N1 142.5(3) . . . . ? C7 N1 C8 C9 -141.4(3) . . . . ? C7 N1 C8 C13 39.9(4) . . . . ? C13 C8 C9 C10 -0.2(4) . . . . ? N1 C8 C9 C10 -178.9(2) . . . . ? C13 C8 C9 I1 -177.37(19) . . . . ? N1 C8 C9 I1 3.9(3) . . . . ? C8 C9 C10 C11 -0.8(4) . . . . ? I1 C9 C10 C11 176.4(2) . . . . ? C9 C10 C11 C12 1.0(5) . . . . ? C10 C11 C12 C13 -0.2(5) . . . . ? C11 C12 C13 C8 -0.8(5) . . . . ? C9 C8 C13 C12 1.0(4) . . . . ? N1 C8 C13 C12 179.7(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.423 _refine_diff_density_min -0.505 _refine_diff_density_rms 0.059 # Attachment '- CIF.cif' #============================================================================= data_2FA-2IB _database_code_depnum_ccdc_archive 'CCDC 811042' #TrackingRef '- CIF.cif' #============================================================================= _chemical_name_systematic ; 2-iodo-N-(2-fluorophenyl)benzamide ; _chemical_name_common 2-iodo-N-(2-fluorophenyl)benzamide _chemical_formula_moiety 'C13 H9 F I N O' _chemical_formula_sum 'C13 H9 F I N O' _chemical_formula_weight 341.11 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 Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 9.0447(2) _cell_length_b 14.1185(3) _cell_length_c 9.9862(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1275.21(5) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 420 _cell_measurement_theta_min 0.97 _cell_measurement_theta_max 27.98 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.777 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 2.506 _exptl_absorpt_correction_T_min 0.6086 _exptl_absorpt_correction_T_max 0.7365 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7168 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 25.98 _reflns_number_total 2362 _reflns_number_gt 1912 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction SAINT _computing_structure_solution 'WinGX-Version 1.70.01(Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0356P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(3) _refine_ls_number_reflns 2362 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0711 _refine_ls_wR_factor_gt 0.0688 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 F1A F 0.2127(7) 0.7077(3) 0.0921(5) 0.073(2) Uani 0.575(8) 1 d P A -1 C8A C 0.0822(3) 0.8265(2) 0.2012(5) 0.0413(9) Uani 0.575(8) 1 d P A -1 C9A C 0.1819(6) 0.7963(3) 0.1049(5) 0.0577(12) Uani 0.575(8) 1 d P A -1 C10A C 0.2499(6) 0.8592(4) 0.0213(5) 0.0743(16) Uani 0.575(8) 1 d P A -1 H10A H 0.3192 0.8381 -0.0407 0.089 Uiso 0.575(8) 1 calc PR A -1 C11A C 0.2153(7) 0.9549(4) 0.0292(6) 0.0819(17) Uani 0.575(8) 1 d P A -1 H11A H 0.2615 0.9976 -0.0280 0.098 Uiso 0.575(8) 1 calc PR A -1 C12A C 0.1149(6) 0.9866(3) 0.1194(6) 0.0724(16) Uani 0.575(8) 1 d P A -1 H12A H 0.0893 1.0503 0.1234 0.087 Uiso 0.575(8) 1 calc PR A -1 C13A C 0.0510(5) 0.9209(3) 0.2062(6) 0.0597(12) Uani 0.575(8) 1 d P A -1 H13A H -0.0157 0.9424 0.2701 0.072 Uiso 0.575(8) 1 calc PR A -1 F1B F -0.0330(7) 0.9516(4) 0.2938(7) 0.079(3) Uani 0.425(8) 1 d P A -2 C8B C 0.0822(3) 0.8265(2) 0.2012(5) 0.0413(9) Uani 0.425(8) 1 d P A -2 C13B C 0.1819(6) 0.7963(3) 0.1049(5) 0.0577(12) Uani 0.425(8) 1 d P A -2 H13B H 0.2028 0.7321 0.0971 0.069 Uiso 0.425(8) 1 calc PR A -2 C12B C 0.2499(6) 0.8592(4) 0.0213(5) 0.0743(16) Uani 0.425(8) 1 d P A -2 H12B H 0.3192 0.8381 -0.0407 0.089 Uiso 0.425(8) 1 calc PR A -2 C11B C 0.2153(7) 0.9549(4) 0.0292(6) 0.0819(17) Uani 0.425(8) 1 d P A -2 H11B H 0.2615 0.9976 -0.0280 0.098 Uiso 0.425(8) 1 calc PR A -2 C10B C 0.1149(6) 0.9866(3) 0.1194(6) 0.0724(16) Uani 0.425(8) 1 d P A -2 H10B H 0.0893 1.0503 0.1234 0.087 Uiso 0.425(8) 1 calc PR A -2 C9B C 0.0510(5) 0.9209(3) 0.2062(6) 0.0597(12) Uani 0.425(8) 1 d P A -2 I1 I 0.14434(4) 0.73606(2) 0.68693(7) 0.08862(18) Uani 1 1 d . . . O1 O 0.2167(3) 0.6834(2) 0.3587(3) 0.0634(10) Uani 1 1 d . . . N1 N 0.0116(4) 0.7621(2) 0.2909(4) 0.0433(8) Uani 1 1 d . . . H1 H -0.0830 0.7647 0.2982 0.052 Uiso 1 1 calc R A . C1 C -0.0118(4) 0.6389(2) 0.4543(4) 0.0373(9) Uani 1 1 d . . . C2 C -0.1129(4) 0.5766(3) 0.3981(4) 0.0467(10) Uani 1 1 d . A . H2 H -0.1288 0.5776 0.3061 0.056 Uiso 1 1 calc R . . C3 C -0.1904(5) 0.5132(3) 0.4764(5) 0.0582(12) Uani 1 1 d . . . H3 H -0.2568 0.4713 0.4371 0.070 Uiso 1 1 calc R A . C4 C -0.1691(5) 0.5120(3) 0.6126(5) 0.0610(13) Uani 1 1 d . A . H4 H -0.2206 0.4691 0.6657 0.073 Uiso 1 1 calc R . . C5 C -0.0707(4) 0.5749(3) 0.6706(5) 0.0520(10) Uani 1 1 d . . . H5 H -0.0567 0.5746 0.7629 0.062 Uiso 1 1 calc R A . C6 C 0.0065(4) 0.6379(3) 0.5918(4) 0.0424(9) Uani 1 1 d . A . C7 C 0.0848(4) 0.6976(3) 0.3644(4) 0.0400(9) Uani 1 1 d . A . 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 F1A 0.104(5) 0.050(3) 0.066(3) -0.004(2) 0.033(3) -0.007(3) C8A 0.0318(18) 0.048(2) 0.044(2) 0.012(2) 0.001(2) -0.0063(13) C9A 0.060(3) 0.060(3) 0.053(3) 0.005(2) 0.001(2) -0.020(2) C10A 0.084(4) 0.096(5) 0.043(3) 0.010(3) 0.005(3) -0.037(3) C11A 0.081(4) 0.096(5) 0.069(4) 0.034(3) -0.018(4) -0.037(3) C12A 0.075(4) 0.047(3) 0.095(4) 0.026(3) -0.023(3) -0.015(2) C13A 0.048(2) 0.060(3) 0.071(4) 0.008(3) -0.005(3) 0.007(2) F1B 0.084(5) 0.063(4) 0.089(6) 0.016(4) 0.021(5) 0.020(4) C8B 0.0318(18) 0.048(2) 0.044(2) 0.012(2) 0.001(2) -0.0063(13) C13B 0.060(3) 0.060(3) 0.053(3) 0.005(2) 0.001(2) -0.020(2) C12B 0.084(4) 0.096(5) 0.043(3) 0.010(3) 0.005(3) -0.037(3) C11B 0.081(4) 0.096(5) 0.069(4) 0.034(3) -0.018(4) -0.037(3) C10B 0.075(4) 0.047(3) 0.095(4) 0.026(3) -0.023(3) -0.015(2) C9B 0.048(2) 0.060(3) 0.071(4) 0.008(3) -0.005(3) 0.007(2) I1 0.0877(3) 0.0921(3) 0.0860(3) -0.0217(3) -0.0246(3) -0.01852(18) O1 0.0251(15) 0.084(2) 0.081(3) 0.0346(19) 0.0108(16) 0.0080(15) N1 0.0288(17) 0.0482(18) 0.053(2) 0.0144(16) 0.0043(15) -0.0015(14) C1 0.0258(19) 0.0373(19) 0.049(3) 0.0104(17) 0.0056(17) 0.0047(14) C2 0.038(2) 0.055(3) 0.048(3) 0.0036(19) -0.0017(18) 0.0001(18) C3 0.051(3) 0.054(3) 0.069(4) 0.002(2) 0.001(2) -0.015(2) C4 0.056(3) 0.050(3) 0.076(4) 0.015(2) 0.020(3) -0.005(2) C5 0.059(2) 0.061(2) 0.037(3) 0.013(2) 0.009(2) 0.0131(19) C6 0.042(2) 0.048(2) 0.037(3) -0.0016(18) -0.0003(18) 0.0035(17) C7 0.036(2) 0.046(2) 0.038(2) 0.0069(18) 0.0003(19) 0.0021(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1A C9A 1.288(7) . ? C8A C13A 1.363(5) . ? C8A C9A 1.385(6) . ? C8A N1 1.427(5) . ? C9A C10A 1.366(7) . ? C10A C11A 1.389(7) . ? C10A H10A 0.9300 . ? C11A C12A 1.356(8) . ? C11A H11A 0.9300 . ? C12A C13A 1.394(7) . ? C12A H12A 0.9300 . ? C13A H13A 0.9300 . ? I1 C6 2.093(4) . ? O1 C7 1.211(4) . ? N1 C7 1.344(5) . ? N1 H1 0.8600 . ? C1 C6 1.382(5) . ? C1 C2 1.388(5) . ? C1 C7 1.503(5) . ? C2 C3 1.381(6) . ? C2 H2 0.9300 . ? C3 C4 1.373(6) . ? C3 H3 0.9300 . ? C4 C5 1.384(7) . ? C4 H4 0.9300 . ? C5 C6 1.378(6) . ? C5 H5 0.9300 . ? 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 C13A C8A C9A 117.4(4) . . ? C13A C8A N1 120.5(4) . . ? C9A C8A N1 122.1(3) . . ? F1A C9A C10A 118.3(5) . . ? F1A C9A C8A 120.5(4) . . ? C10A C9A C8A 121.2(5) . . ? C9A C10A C11A 119.8(6) . . ? C9A C10A H10A 120.1 . . ? C11A C10A H10A 120.1 . . ? C12A C11A C10A 120.6(5) . . ? C12A C11A H11A 119.7 . . ? C10A C11A H11A 119.7 . . ? C11A C12A C13A 118.1(5) . . ? C11A C12A H12A 121.0 . . ? C13A C12A H12A 121.0 . . ? C8A C13A C12A 122.8(5) . . ? C8A C13A H13A 118.6 . . ? C12A C13A H13A 118.6 . . ? C7 N1 C8A 123.6(3) . . ? C7 N1 H1 118.2 . . ? C8A N1 H1 118.2 . . ? C6 C1 C2 118.3(3) . . ? C6 C1 C7 122.0(3) . . ? C2 C1 C7 119.4(4) . . ? C3 C2 C1 121.1(4) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C4 C3 C2 119.9(4) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 119.8(4) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 120.1(4) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 120.9(4) . . ? C5 C6 I1 118.0(3) . . ? C1 C6 I1 121.0(3) . . ? O1 C7 N1 124.8(4) . . ? O1 C7 C1 120.7(3) . . ? N1 C7 C1 114.4(3) . . ? 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 C13A C8A C9A F1A -177.8(5) . . . . ? N1 C8A C9A F1A 0.9(7) . . . . ? C13A C8A C9A C10A 2.2(7) . . . . ? N1 C8A C9A C10A -179.0(4) . . . . ? F1A C9A C10A C11A 177.7(5) . . . . ? C8A C9A C10A C11A -2.3(8) . . . . ? C9A C10A C11A C12A 0.2(8) . . . . ? C10A C11A C12A C13A 1.8(8) . . . . ? C9A C8A C13A C12A -0.1(7) . . . . ? N1 C8A C13A C12A -178.9(4) . . . . ? C11A C12A C13A C8A -1.9(8) . . . . ? C13A C8A N1 C7 -130.2(5) . . . . ? C9A C8A N1 C7 51.1(6) . . . . ? C6 C1 C2 C3 -1.9(6) . . . . ? C7 C1 C2 C3 171.8(4) . . . . ? C1 C2 C3 C4 0.9(6) . . . . ? C2 C3 C4 C5 0.4(7) . . . . ? C3 C4 C5 C6 -0.5(7) . . . . ? C4 C5 C6 C1 -0.6(6) . . . . ? C4 C5 C6 I1 176.6(3) . . . . ? C2 C1 C6 C5 1.8(5) . . . . ? C7 C1 C6 C5 -171.8(3) . . . . ? C2 C1 C6 I1 -175.3(3) . . . . ? C7 C1 C6 I1 11.1(5) . . . . ? C8A N1 C7 O1 -3.8(7) . . . . ? C8A N1 C7 C1 178.6(4) . . . . ? C6 C1 C7 O1 62.0(5) . . . . ? C2 C1 C7 O1 -111.5(4) . . . . ? C6 C1 C7 N1 -120.3(4) . . . . ? C2 C1 C7 N1 66.2(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.463 _refine_diff_density_min -0.640 _refine_diff_density_rms 0.055