# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'William Jones' _publ_contact_author_email WJ10@CAM.AC.UK _publ_section_title ; A cocrystallisation-based strategy to construct isostructural solids ; loop_ _publ_author_name 'William Jones' 'Dominik Cincic' 'Tomislav Friscic' # Attachment 'B805816D.cif' data_ipb-phen _database_code_depnum_ccdc_archive 'CCDC 683639' _audit_creation_method SHELXL-97 _chemical_name_systematic ; iodopentafluorobenzene-phenazine 1/1 ; _chemical_name_common 'iodopentafluorobenzene-phenazine 1/1' _chemical_melting_point ? _chemical_formula_moiety 'C6 F5 I, C12 H8 N2' _chemical_formula_sum 'C18 H8 F5 I N2' _chemical_formula_weight 474.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.8943(3) _cell_length_b 7.22990(10) _cell_length_c 14.9051(2) _cell_angle_alpha 90.00 _cell_angle_beta 116.0800(10) _cell_angle_gamma 90.00 _cell_volume 1635.20(4) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 13239 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 31.51 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.926 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 2.015 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.721 _exptl_absorpt_correction_T_max 0.792 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 18302 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 31.52 _reflns_number_total 5436 _reflns_number_gt 4686 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-hydrogen atoms were involved in the refinement, using the anisotropic model. Coordinates of hydrogen atoms bonded to phenazine carbon atoms were calculated using stereochemical rules valid for sp2 hybridised C-atoms and included in the refinement using the riding model. ; _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^)+(0.0132P)^2^+1.1906P] 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 5436 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0586 _refine_ls_wR_factor_gt 0.0554 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.259496(8) 0.438800(17) 0.281113(8) 0.02678(4) Uani 1 1 d . . . F1 F 0.16587(8) 0.56400(19) 0.41948(9) 0.0352(3) Uani 1 1 d . . . F2 F 0.22469(9) 0.5778(2) 0.61870(9) 0.0419(3) Uani 1 1 d . . . F3 F 0.39196(9) 0.4733(2) 0.74164(8) 0.0444(3) Uani 1 1 d . . . F4 F 0.50077(8) 0.3509(2) 0.66360(9) 0.0425(3) Uani 1 1 d . . . F5 F 0.44353(7) 0.33690(19) 0.46451(9) 0.0346(3) Uani 1 1 d . . . N1 N 0.20495(10) 0.4209(2) 0.06662(11) 0.0249(3) Uani 1 1 d . . . N2 N 0.14653(11) 0.4426(2) -0.14312(12) 0.0289(3) Uani 1 1 d . . . C1 C 0.12357(12) 0.3647(3) 0.00216(13) 0.0260(3) Uani 1 1 d . . . C2 C 0.09455(12) 0.3768(3) -0.10385(14) 0.0286(4) Uani 1 1 d . . . C3 C 0.00784(13) 0.3129(4) -0.16885(16) 0.0410(5) Uani 1 1 d . . . H3 H -0.0129 0.3209 -0.2392 0.049 Uiso 1 1 calc R . . C4 C -0.04446(14) 0.2413(4) -0.13046(18) 0.0440(5) Uani 1 1 d . . . H4 H -0.1015 0.1974 -0.1744 0.053 Uiso 1 1 calc R . . C5 C -0.01599(14) 0.2303(3) -0.02555(18) 0.0403(5) Uani 1 1 d . . . H5 H -0.0543 0.1805 -0.0004 0.048 Uiso 1 1 calc R . . C6 C 0.06570(14) 0.2903(3) 0.03922(16) 0.0339(4) Uani 1 1 d . . . H6 H 0.0841 0.2826 0.1092 0.041 Uiso 1 1 calc R . . C7 C 0.25814(12) 0.4837(3) 0.02730(12) 0.0225(3) Uani 1 1 d . . . C8 C 0.22871(12) 0.4943(3) -0.07853(13) 0.0240(3) Uani 1 1 d . . . C9 C 0.28810(14) 0.5564(3) -0.11612(14) 0.0287(4) Uani 1 1 d . . . H9 H 0.2690 0.5649 -0.1862 0.034 Uiso 1 1 calc R . . C10 C 0.37213(14) 0.6039(3) -0.05245(15) 0.0303(4) Uani 1 1 d . . . H10 H 0.4115 0.6436 -0.0785 0.036 Uiso 1 1 calc R . . C11 C 0.40160(13) 0.5946(3) 0.05263(14) 0.0293(4) Uani 1 1 d . . . H11 H 0.4604 0.6292 0.0960 0.035 Uiso 1 1 calc R . . C12 C 0.34672(12) 0.5367(3) 0.09196(13) 0.0268(4) Uani 1 1 d . . . H12 H 0.3673 0.5315 0.1624 0.032 Uiso 1 1 calc R . . C13 C 0.30283(12) 0.4487(3) 0.43595(12) 0.0225(3) Uani 1 1 d . . . C14 C 0.24875(11) 0.5093(3) 0.47757(13) 0.0247(3) Uani 1 1 d . . . C15 C 0.27799(13) 0.5171(3) 0.57990(14) 0.0275(4) Uani 1 1 d . . . C16 C 0.36319(13) 0.4642(3) 0.64255(13) 0.0285(4) Uani 1 1 d . . . C17 C 0.41807(12) 0.4036(3) 0.60279(14) 0.0284(4) Uani 1 1 d . . . C18 C 0.38799(12) 0.3966(3) 0.50036(13) 0.0247(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.03108(7) 0.02840(7) 0.02136(6) 0.00097(4) 0.01198(4) -0.00046(5) F1 0.0231(5) 0.0479(8) 0.0319(6) 0.0033(5) 0.0096(4) 0.0090(5) F2 0.0370(7) 0.0622(10) 0.0349(6) -0.0045(6) 0.0235(5) 0.0079(6) F3 0.0423(7) 0.0676(10) 0.0200(5) -0.0027(5) 0.0106(5) 0.0018(7) F4 0.0244(6) 0.0593(9) 0.0337(6) 0.0020(6) 0.0034(5) 0.0092(6) F5 0.0276(5) 0.0440(8) 0.0369(6) -0.0027(5) 0.0184(5) 0.0061(5) N1 0.0236(7) 0.0272(8) 0.0241(7) -0.0015(6) 0.0108(6) -0.0031(6) N2 0.0257(7) 0.0333(9) 0.0230(7) 0.0000(6) 0.0064(6) 0.0018(7) C1 0.0232(8) 0.0254(9) 0.0292(8) -0.0023(7) 0.0113(7) -0.0001(7) C2 0.0232(8) 0.0306(10) 0.0264(8) -0.0017(7) 0.0058(6) 0.0010(7) C3 0.0254(9) 0.0517(14) 0.0347(10) -0.0048(10) 0.0030(8) -0.0044(10) C4 0.0227(9) 0.0483(14) 0.0509(13) -0.0061(10) 0.0070(8) -0.0066(9) C5 0.0285(9) 0.0397(13) 0.0557(13) -0.0015(10) 0.0212(9) -0.0061(9) C6 0.0312(9) 0.0353(11) 0.0386(10) -0.0019(8) 0.0183(8) -0.0048(9) C7 0.0243(8) 0.0217(8) 0.0212(7) -0.0014(6) 0.0097(6) -0.0002(7) C8 0.0259(8) 0.0233(8) 0.0225(8) 0.0008(6) 0.0105(6) 0.0023(7) C9 0.0351(9) 0.0297(9) 0.0240(8) 0.0017(7) 0.0155(7) 0.0012(8) C10 0.0333(9) 0.0286(10) 0.0352(9) 0.0010(7) 0.0207(8) -0.0018(8) C11 0.0243(8) 0.0299(10) 0.0322(9) -0.0010(7) 0.0110(7) -0.0042(7) C12 0.0252(8) 0.0302(10) 0.0224(8) -0.0011(6) 0.0083(6) -0.0038(7) C13 0.0238(8) 0.0240(8) 0.0200(7) 0.0008(6) 0.0099(6) -0.0010(7) C14 0.0206(7) 0.0281(9) 0.0251(8) 0.0013(7) 0.0099(6) 0.0023(7) C15 0.0285(9) 0.0317(10) 0.0271(8) -0.0015(7) 0.0167(7) 0.0006(8) C16 0.0294(9) 0.0348(11) 0.0194(7) -0.0016(7) 0.0089(6) -0.0026(8) C17 0.0214(8) 0.0330(10) 0.0263(8) 0.0004(7) 0.0062(6) 0.0030(7) C18 0.0232(8) 0.0263(9) 0.0276(8) -0.0002(6) 0.0138(6) 0.0015(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C13 2.0933(16) . ? F1 C14 1.342(2) . ? F2 C15 1.340(2) . ? F3 C16 1.338(2) . ? F4 C17 1.344(2) . ? F5 C18 1.339(2) . ? N1 C1 1.348(2) . ? N1 C7 1.349(2) . ? N2 C2 1.339(3) . ? N2 C8 1.349(2) . ? C1 C6 1.423(3) . ? C1 C2 1.436(3) . ? C2 C3 1.432(3) . ? C3 C4 1.349(3) . ? C4 C5 1.422(3) . ? C5 C6 1.362(3) . ? C7 C12 1.431(2) . ? C7 C8 1.432(2) . ? C8 C9 1.420(3) . ? C9 C10 1.360(3) . ? C10 C11 1.421(3) . ? C11 C12 1.363(3) . ? C13 C14 1.382(2) . ? C13 C18 1.385(2) . ? C14 C15 1.382(3) . ? C15 C16 1.381(3) . ? C16 C17 1.373(3) . ? C17 C18 1.382(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C7 117.21(15) . . ? C2 N2 C8 116.98(16) . . ? N1 C1 C6 119.78(17) . . ? N1 C1 C2 120.92(17) . . ? C6 C1 C2 119.29(17) . . ? N2 C2 C3 119.43(18) . . ? N2 C2 C1 122.02(17) . . ? C3 C2 C1 118.54(19) . . ? C4 C3 C2 120.2(2) . . ? C3 C4 C5 121.33(19) . . ? C6 C5 C4 120.6(2) . . ? C5 C6 C1 120.0(2) . . ? N1 C7 C12 119.79(15) . . ? N1 C7 C8 121.42(16) . . ? C12 C7 C8 118.77(16) . . ? N2 C8 C9 119.36(16) . . ? N2 C8 C7 121.42(17) . . ? C9 C8 C7 119.21(16) . . ? C10 C9 C8 120.42(17) . . ? C9 C10 C11 120.65(18) . . ? C12 C11 C10 120.91(17) . . ? C11 C12 C7 120.04(16) . . ? C14 C13 C18 117.73(15) . . ? C14 C13 I1 121.73(13) . . ? C18 C13 I1 120.53(13) . . ? F1 C14 C13 120.80(15) . . ? F1 C14 C15 117.73(16) . . ? C13 C14 C15 121.47(16) . . ? F2 C15 C16 119.81(16) . . ? F2 C15 C14 120.49(17) . . ? C16 C15 C14 119.69(17) . . ? F3 C16 C17 120.36(17) . . ? F3 C16 C15 119.83(18) . . ? C17 C16 C15 119.81(16) . . ? F4 C17 C16 119.90(17) . . ? F4 C17 C18 120.20(17) . . ? C16 C17 C18 119.90(17) . . ? F5 C18 C17 118.09(16) . . ? F5 C18 C13 120.50(16) . . ? C17 C18 C13 121.40(17) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 31.52 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.431 _refine_diff_density_min -0.957 _refine_diff_density_rms 0.087 data_ipb-acr _database_code_depnum_ccdc_archive 'CCDC 683640' _audit_creation_method SHELXL-97 _chemical_name_systematic ; iodopentafluorobenzene-acridine 1/1 ; _chemical_name_common 'iodopentafluorobenzene-acridine 1/1' _chemical_melting_point ? _chemical_formula_moiety 'C6 F5 I, C13 H9 N' _chemical_formula_sum 'C19 H9 F5 I N' _chemical_formula_weight 473.17 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.9525(3) _cell_length_b 7.2187(2) _cell_length_c 14.9464(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.2460(10) _cell_angle_gamma 90.00 _cell_volume 1640.49(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8629 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 31.51 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.916 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 2.007 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.649 _exptl_absorpt_correction_T_max 0.698 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 10457 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 31.50 _reflns_number_total 5306 _reflns_number_gt 4746 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-hydrogen atoms were included in the refinement using the anisotropic model. Coordinates of hydrogen atoms bonded to carbon atoms of acridine were calculated using the stereochemical rules applicable to sp2-hybridised carbon atoms and included in the refinement using the riding model. ; _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^)+(0.0147P)^2^+1.3685P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5306 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0295 _refine_ls_R_factor_gt 0.0239 _refine_ls_wR_factor_ref 0.0591 _refine_ls_wR_factor_gt 0.0565 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.262246(7) 0.436762(15) 0.279538(7) 0.01946(4) Uani 1 1 d . . . F1 F 0.16720(7) 0.56093(16) 0.41596(9) 0.0266(2) Uani 1 1 d . . . F2 F 0.22513(8) 0.57591(18) 0.61503(9) 0.0324(3) Uani 1 1 d . . . F3 F 0.39246(9) 0.4756(2) 0.73920(8) 0.0340(3) Uani 1 1 d . . . F4 F 0.50234(7) 0.35414(19) 0.66314(9) 0.0323(3) Uani 1 1 d . . . F5 F 0.44586(7) 0.33800(17) 0.46409(8) 0.0256(2) Uani 1 1 d . . . N1 N 0.20531(10) 0.4158(2) 0.06611(11) 0.0186(3) Uani 1 1 d . . . C1 C 0.12217(11) 0.3626(2) 0.00424(12) 0.0183(3) Uani 1 1 d . . . C2 C 0.08756(11) 0.3753(2) -0.10265(12) 0.0191(3) Uani 1 1 d . . . C3 C -0.00143(12) 0.3187(3) -0.16281(14) 0.0256(4) Uani 1 1 d . . . H3 H -0.0256 0.3281 -0.2334 0.031 Uiso 1 1 calc R . . C4 C -0.05153(12) 0.2517(3) -0.12009(15) 0.0270(4) Uani 1 1 d . . . H4 H -0.1104 0.2146 -0.1610 0.032 Uiso 1 1 calc R . . C5 C -0.01654(12) 0.2366(3) -0.01451(15) 0.0264(4) Uani 1 1 d . . . H5 H -0.0522 0.1884 0.0143 0.032 Uiso 1 1 calc R . . C6 C 0.06750(12) 0.2903(3) 0.04564(14) 0.0227(3) Uani 1 1 d . . . H6 H 0.0898 0.2794 0.1160 0.027 Uiso 1 1 calc R . . C7 C 0.25769(11) 0.4788(2) 0.02620(12) 0.0171(3) Uani 1 1 d . . . C8 C 0.22867(11) 0.4935(2) -0.07970(12) 0.0173(3) Uani 1 1 d . . . C9 C 0.28864(12) 0.5551(2) -0.11622(13) 0.0208(3) Uani 1 1 d . . . H9 H 0.2697 0.5644 -0.1861 0.025 Uiso 1 1 calc R . . C10 C 0.37300(13) 0.6012(3) -0.05221(14) 0.0235(3) Uani 1 1 d . . . H10 H 0.4125 0.6415 -0.0776 0.028 Uiso 1 1 calc R . . C11 C 0.40179(12) 0.5888(2) 0.05277(14) 0.0225(3) Uani 1 1 d . . . H11 H 0.4605 0.6218 0.0969 0.027 Uiso 1 1 calc R . . C12 C 0.34626(12) 0.5303(2) 0.09099(13) 0.0206(3) Uani 1 1 d . . . H12 H 0.3667 0.5238 0.1612 0.025 Uiso 1 1 calc R . . C13 C 0.14202(12) 0.4417(2) -0.14215(13) 0.0204(3) Uani 1 1 d . . . H13 H 0.1204 0.4522 -0.2124 0.024 Uiso 1 1 calc R . . C14 C 0.30499(11) 0.4488(2) 0.43401(12) 0.0171(3) Uani 1 1 d . . . C15 C 0.25047(11) 0.5085(2) 0.47503(13) 0.0189(3) Uani 1 1 d . . . C16 C 0.27903(12) 0.5175(3) 0.57704(13) 0.0213(3) Uani 1 1 d . . . C17 C 0.36409(12) 0.4660(3) 0.64030(13) 0.0218(3) Uani 1 1 d . . . C18 C 0.41994(11) 0.4063(2) 0.60175(13) 0.0209(3) Uani 1 1 d . . . C19 C 0.39012(11) 0.3978(2) 0.49903(13) 0.0191(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.02260(6) 0.02051(6) 0.01555(6) 0.00080(4) 0.00869(4) -0.00028(4) F1 0.0172(5) 0.0349(6) 0.0255(5) 0.0020(4) 0.0074(4) 0.0070(4) F2 0.0301(6) 0.0467(7) 0.0287(6) -0.0037(5) 0.0205(5) 0.0063(5) F3 0.0349(6) 0.0503(8) 0.0145(5) -0.0027(5) 0.0090(5) 0.0012(6) F4 0.0194(5) 0.0452(7) 0.0239(5) 0.0020(5) 0.0019(4) 0.0077(5) F5 0.0204(5) 0.0330(6) 0.0269(5) -0.0019(4) 0.0138(4) 0.0047(4) N1 0.0188(6) 0.0204(6) 0.0166(6) 0.0001(5) 0.0079(5) -0.0009(5) C1 0.0200(7) 0.0176(7) 0.0177(7) -0.0011(5) 0.0086(6) -0.0002(6) C2 0.0189(7) 0.0188(7) 0.0177(7) -0.0009(6) 0.0064(6) 0.0013(6) C3 0.0214(8) 0.0301(9) 0.0205(8) -0.0028(7) 0.0048(6) -0.0013(7) C4 0.0178(7) 0.0288(9) 0.0318(9) -0.0062(7) 0.0085(7) -0.0040(7) C5 0.0223(8) 0.0254(8) 0.0338(9) -0.0021(7) 0.0144(7) -0.0025(7) C6 0.0230(8) 0.0238(8) 0.0241(8) -0.0005(6) 0.0128(7) -0.0031(7) C7 0.0182(7) 0.0165(7) 0.0166(7) 0.0001(5) 0.0077(6) 0.0012(6) C8 0.0211(7) 0.0151(6) 0.0168(7) 0.0007(5) 0.0093(6) 0.0012(6) C9 0.0255(8) 0.0211(7) 0.0192(7) 0.0019(6) 0.0130(7) 0.0004(6) C10 0.0250(8) 0.0231(8) 0.0281(8) 0.0013(7) 0.0170(7) -0.0017(7) C11 0.0200(7) 0.0227(8) 0.0251(8) -0.0005(6) 0.0103(7) -0.0028(6) C12 0.0202(7) 0.0227(8) 0.0173(7) -0.0011(6) 0.0067(6) -0.0024(6) C13 0.0220(8) 0.0222(8) 0.0162(7) 0.0011(6) 0.0078(6) 0.0016(6) C14 0.0191(7) 0.0173(7) 0.0153(7) -0.0002(5) 0.0081(6) -0.0004(6) C15 0.0163(7) 0.0205(7) 0.0192(7) 0.0006(6) 0.0073(6) 0.0014(6) C16 0.0225(8) 0.0245(8) 0.0215(8) -0.0024(6) 0.0140(7) 0.0004(7) C17 0.0250(8) 0.0246(8) 0.0154(7) -0.0004(6) 0.0085(6) -0.0002(7) C18 0.0173(7) 0.0238(8) 0.0194(7) 0.0007(6) 0.0062(6) 0.0012(6) C19 0.0180(7) 0.0200(7) 0.0212(7) -0.0008(6) 0.0104(6) 0.0003(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C14 2.0937(16) . ? F1 C15 1.3465(19) . ? F2 C16 1.339(2) . ? F3 C17 1.339(2) . ? F4 C18 1.342(2) . ? F5 C19 1.337(2) . ? N1 C7 1.349(2) . ? N1 C1 1.355(2) . ? C1 C6 1.422(2) . ? C1 C2 1.441(2) . ? C2 C13 1.383(3) . ? C2 C3 1.432(2) . ? C3 C4 1.358(3) . ? C3 H3 0.9500 . ? C4 C5 1.423(3) . ? C4 H4 0.9500 . ? C5 C6 1.362(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.430(2) . ? C7 C8 1.439(2) . ? C8 C13 1.399(2) . ? C8 C9 1.421(2) . ? C9 C10 1.364(3) . ? C9 H9 0.9500 . ? C10 C11 1.425(3) . ? C10 H10 0.9500 . ? C11 C12 1.366(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.385(2) . ? C14 C19 1.387(2) . ? C15 C16 1.382(2) . ? C16 C17 1.380(3) . ? C17 C18 1.377(3) . ? C18 C19 1.389(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C1 118.89(15) . . ? N1 C1 C6 119.23(15) . . ? N1 C1 C2 121.97(16) . . ? C6 C1 C2 118.79(15) . . ? C13 C2 C3 123.19(16) . . ? C13 C2 C1 118.29(15) . . ? C3 C2 C1 118.52(17) . . ? C4 C3 C2 120.71(17) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 120.54(17) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 120.75(18) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 120.67(17) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? N1 C7 C12 119.19(15) . . ? N1 C7 C8 122.67(15) . . ? C12 C7 C8 118.13(16) . . ? C13 C8 C9 123.09(16) . . ? C13 C8 C7 117.49(16) . . ? C9 C8 C7 119.41(15) . . ? C10 C9 C8 120.86(17) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 119.96(17) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 121.05(17) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C7 120.58(16) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? C2 C13 C8 120.68(16) . . ? C2 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? C15 C14 C19 117.65(15) . . ? C15 C14 I1 121.87(12) . . ? C19 C14 I1 120.48(13) . . ? F1 C15 C16 117.67(16) . . ? F1 C15 C14 120.58(15) . . ? C16 C15 C14 121.75(16) . . ? F2 C16 C17 119.76(16) . . ? F2 C16 C15 120.70(16) . . ? C17 C16 C15 119.54(17) . . ? F3 C17 C18 120.02(17) . . ? F3 C17 C16 119.91(17) . . ? C18 C17 C16 120.07(16) . . ? F4 C18 C17 120.14(16) . . ? F4 C18 C19 120.21(17) . . ? C17 C18 C19 119.64(16) . . ? F5 C19 C14 120.55(16) . . ? F5 C19 C18 118.11(15) . . ? C14 C19 C18 121.34(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 C7 N1 C1 C6 177.96(16) . . . . ? C7 N1 C1 C2 -1.4(2) . . . . ? N1 C1 C2 C13 0.8(3) . . . . ? C6 C1 C2 C13 -178.49(16) . . . . ? N1 C1 C2 C3 -179.12(17) . . . . ? C6 C1 C2 C3 1.5(2) . . . . ? C13 C2 C3 C4 178.94(19) . . . . ? C1 C2 C3 C4 -1.1(3) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C4 C5 C6 C1 -0.1(3) . . . . ? N1 C1 C6 C5 179.66(17) . . . . ? C2 C1 C6 C5 -1.0(3) . . . . ? C1 N1 C7 C12 -178.30(16) . . . . ? C1 N1 C7 C8 0.5(2) . . . . ? N1 C7 C8 C13 0.8(2) . . . . ? C12 C7 C8 C13 179.65(16) . . . . ? N1 C7 C8 C9 -177.81(16) . . . . ? C12 C7 C8 C9 1.0(2) . . . . ? C13 C8 C9 C10 -178.87(17) . . . . ? C7 C8 C9 C10 -0.3(3) . . . . ? C8 C9 C10 C11 -0.4(3) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? C10 C11 C12 C7 0.4(3) . . . . ? N1 C7 C12 C11 177.82(16) . . . . ? C8 C7 C12 C11 -1.1(3) . . . . ? C3 C2 C13 C8 -179.47(17) . . . . ? C1 C2 C13 C8 0.6(3) . . . . ? C9 C8 C13 C2 177.23(16) . . . . ? C7 C8 C13 C2 -1.3(2) . . . . ? C19 C14 C15 F1 179.66(16) . . . . ? I1 C14 C15 F1 0.1(2) . . . . ? C19 C14 C15 C16 0.0(3) . . . . ? I1 C14 C15 C16 -179.57(14) . . . . ? F1 C15 C16 F2 0.2(3) . . . . ? C14 C15 C16 F2 179.91(17) . . . . ? F1 C15 C16 C17 -179.64(16) . . . . ? C14 C15 C16 C17 0.0(3) . . . . ? F2 C16 C17 F3 -0.3(3) . . . . ? C15 C16 C17 F3 179.54(17) . . . . ? F2 C16 C17 C18 -179.83(17) . . . . ? C15 C16 C17 C18 0.0(3) . . . . ? F3 C17 C18 F4 1.3(3) . . . . ? C16 C17 C18 F4 -179.22(17) . . . . ? F3 C17 C18 C19 -179.65(17) . . . . ? C16 C17 C18 C19 -0.2(3) . . . . ? C15 C14 C19 F5 179.64(16) . . . . ? I1 C14 C19 F5 -0.8(2) . . . . ? C15 C14 C19 C18 -0.1(3) . . . . ? I1 C14 C19 C18 179.46(13) . . . . ? F4 C18 C19 F5 -0.5(3) . . . . ? C17 C18 C19 F5 -179.56(16) . . . . ? F4 C18 C19 C14 179.26(16) . . . . ? C17 C18 C19 C14 0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 31.50 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.653 _refine_diff_density_min -1.093 _refine_diff_density_rms 0.156 data_acr-bpb _database_code_depnum_ccdc_archive 'CCDC 683641' _audit_creation_method SHELXL-97 _chemical_name_systematic ; acridine-bromopentafluorobenzene 1/1 ; _chemical_name_common 'acridine-bromopentafluorobenzene 1/1' _chemical_melting_point ? _chemical_formula_moiety 'C6 Br F5, C13 H9 N' _chemical_formula_sum 'C19 H9 Br F5 N' _chemical_formula_weight 426.18 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.0193(7) _cell_length_b 7.2045(2) _cell_length_c 14.7399(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.5350(10) _cell_angle_gamma 90.00 _cell_volume 1616.96(9) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9218 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 30.03 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.751 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 2.598 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.636 _exptl_absorpt_correction_T_max 0.776 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 13041 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 30.03 _reflns_number_total 4669 _reflns_number_gt 3627 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-hydrogen atoms were included in the refinement using the anisotropic model. Hydrogen atoms of the acridine molecule were placed in positions calculated for atoms attached to sp2-hybridised carbon atoms and were included in the refinement using the riding model. ; _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^)+(0.0579P)^2^+0.2263P] 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 4669 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0996 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _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 Br1 Br 0.262733(14) 0.44227(3) 0.286454(15) 0.03475(8) Uani 1 1 d . . . F1 F 0.16576(8) 0.56395(17) 0.40926(11) 0.0410(3) Uani 1 1 d . . . F2 F 0.22440(10) 0.57292(19) 0.61204(12) 0.0486(4) Uani 1 1 d . . . F3 F 0.39111(10) 0.4668(2) 0.73694(11) 0.0531(4) Uani 1 1 d . . . F4 F 0.49969(8) 0.3503(2) 0.65848(11) 0.0481(3) Uani 1 1 d . . . F5 F 0.44234(8) 0.34096(17) 0.45581(10) 0.0399(3) Uani 1 1 d . . . N1 N 0.20563(11) 0.4144(2) 0.06868(14) 0.0290(3) Uani 1 1 d . . . C1 C 0.12281(13) 0.3609(3) 0.00518(16) 0.0286(4) Uani 1 1 d . . . C2 C 0.08791(13) 0.3714(3) -0.10257(16) 0.0306(4) Uani 1 1 d . . . C3 C -0.00140(14) 0.3150(3) -0.16425(19) 0.0406(5) Uani 1 1 d . . . H3 H -0.0257 0.3219 -0.2361 0.049 Uiso 1 1 calc R . . C4 C -0.05080(14) 0.2520(3) -0.1197(2) 0.0437(5) Uani 1 1 d . . . H4 H -0.1099 0.2159 -0.1608 0.052 Uiso 1 1 calc R . . C5 C -0.01592(15) 0.2390(3) -0.0130(2) 0.0415(5) Uani 1 1 d . . . H5 H -0.0516 0.1930 0.0164 0.050 Uiso 1 1 calc R . . C6 C 0.06826(14) 0.2917(3) 0.04809(18) 0.0360(5) Uani 1 1 d . . . H6 H 0.0908 0.2823 0.1196 0.043 Uiso 1 1 calc R . . C7 C 0.25742(13) 0.4762(3) 0.02741(15) 0.0265(4) Uani 1 1 d . . . C8 C 0.22869(13) 0.4883(3) -0.07925(15) 0.0285(4) Uani 1 1 d . . . C9 C 0.28889(15) 0.5498(3) -0.11629(18) 0.0338(4) Uani 1 1 d . . . H9 H 0.2704 0.5574 -0.1873 0.041 Uiso 1 1 calc R . . C10 C 0.37240(15) 0.5975(3) -0.05055(19) 0.0374(5) Uani 1 1 d . . . H10 H 0.4120 0.6378 -0.0758 0.045 Uiso 1 1 calc R . . C11 C 0.40072(14) 0.5875(3) 0.05548(19) 0.0366(5) Uani 1 1 d . . . H11 H 0.4592 0.6217 0.1005 0.044 Uiso 1 1 calc R . . C12 C 0.34546(14) 0.5296(3) 0.09388(17) 0.0328(4) Uani 1 1 d . . . H12 H 0.3656 0.5246 0.1652 0.039 Uiso 1 1 calc R . . C13 C 0.14254(14) 0.4354(3) -0.14363(17) 0.0312(4) Uani 1 1 d . . . H13 H 0.1212 0.4430 -0.2151 0.037 Uiso 1 1 calc R . . C14 C 0.30243(13) 0.4518(2) 0.42710(16) 0.0291(4) Uani 1 1 d . . . C15 C 0.24842(13) 0.5101(3) 0.46939(16) 0.0293(4) Uani 1 1 d . . . C16 C 0.27755(14) 0.5157(3) 0.57223(17) 0.0334(4) Uani 1 1 d . . . C17 C 0.36260(15) 0.4620(3) 0.63658(16) 0.0333(4) Uani 1 1 d . . . C18 C 0.41742(13) 0.4041(3) 0.59633(17) 0.0331(4) Uani 1 1 d . . . C19 C 0.38735(13) 0.3986(3) 0.49301(16) 0.0289(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.03668(13) 0.03866(13) 0.02885(12) 0.00104(8) 0.01459(9) -0.00177(8) F1 0.0246(6) 0.0508(8) 0.0438(8) 0.0043(5) 0.0119(6) 0.0092(5) F2 0.0411(8) 0.0679(9) 0.0481(9) -0.0063(6) 0.0302(7) 0.0087(6) F3 0.0475(9) 0.0822(11) 0.0271(7) -0.0025(6) 0.0144(6) 0.0067(7) F4 0.0266(7) 0.0672(9) 0.0410(8) 0.0020(6) 0.0067(6) 0.0099(6) F5 0.0308(7) 0.0495(7) 0.0469(8) -0.0037(6) 0.0240(6) 0.0042(5) N1 0.0263(8) 0.0333(8) 0.0285(9) 0.0002(6) 0.0133(7) -0.0020(6) C1 0.0262(9) 0.0273(9) 0.0332(10) -0.0021(7) 0.0141(8) -0.0001(7) C2 0.0265(10) 0.0310(9) 0.0330(11) -0.0027(8) 0.0121(9) 0.0024(7) C3 0.0285(11) 0.0485(12) 0.0385(13) -0.0060(10) 0.0092(10) -0.0023(9) C4 0.0253(10) 0.0465(13) 0.0556(15) -0.0095(10) 0.0147(10) -0.0065(9) C5 0.0333(11) 0.0395(11) 0.0586(15) -0.0035(10) 0.0266(11) -0.0057(9) C6 0.0338(11) 0.0370(11) 0.0427(12) 0.0003(9) 0.0219(10) -0.0034(8) C7 0.0258(9) 0.0247(9) 0.0307(10) -0.0001(7) 0.0140(8) 0.0005(7) C8 0.0304(10) 0.0259(9) 0.0318(10) 0.0007(7) 0.0161(9) 0.0011(7) C9 0.0385(12) 0.0333(10) 0.0363(11) 0.0023(8) 0.0229(10) 0.0007(8) C10 0.0384(12) 0.0332(10) 0.0509(14) 0.0023(9) 0.0292(11) -0.0016(8) C11 0.0257(10) 0.0346(11) 0.0489(14) -0.0022(9) 0.0162(10) -0.0043(7) C12 0.0287(10) 0.0344(11) 0.0332(11) -0.0013(8) 0.0119(9) -0.0026(7) C13 0.0303(10) 0.0340(10) 0.0271(10) -0.0008(7) 0.0109(8) 0.0022(7) C14 0.0277(10) 0.0289(10) 0.0314(10) 0.0001(7) 0.0138(8) -0.0020(7) C15 0.0229(9) 0.0305(9) 0.0335(11) 0.0014(8) 0.0117(8) 0.0004(7) C16 0.0303(10) 0.0375(10) 0.0398(12) -0.0030(9) 0.0223(10) 0.0000(8) C17 0.0334(11) 0.0388(11) 0.0266(10) -0.0018(8) 0.0125(9) 0.0001(8) C18 0.0229(9) 0.0375(10) 0.0341(11) 0.0018(8) 0.0086(9) 0.0012(7) C19 0.0245(9) 0.0304(9) 0.0348(11) -0.0016(7) 0.0160(8) -0.0016(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C14 1.873(2) . ? F1 C15 1.342(2) . ? F2 C16 1.344(2) . ? F3 C17 1.336(3) . ? F4 C18 1.343(2) . ? F5 C19 1.344(2) . ? N1 C7 1.351(3) . ? N1 C1 1.354(3) . ? C1 C6 1.427(3) . ? C1 C2 1.428(3) . ? C2 C13 1.395(3) . ? C2 C3 1.438(3) . ? C3 C4 1.356(3) . ? C4 C5 1.414(4) . ? C5 C6 1.362(3) . ? C7 C8 1.425(3) . ? C7 C12 1.429(3) . ? C8 C13 1.397(3) . ? C8 C9 1.430(3) . ? C9 C10 1.359(3) . ? C10 C11 1.417(3) . ? C11 C12 1.362(3) . ? C14 C15 1.386(3) . ? C14 C19 1.387(3) . ? C15 C16 1.369(3) . ? C16 C17 1.385(3) . ? C17 C18 1.375(3) . ? C18 C19 1.373(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C1 118.03(18) . . ? N1 C1 C6 118.41(19) . . ? N1 C1 C2 122.77(18) . . ? C6 C1 C2 118.82(19) . . ? C13 C2 C1 118.26(18) . . ? C13 C2 C3 122.7(2) . . ? C1 C2 C3 119.0(2) . . ? C4 C3 C2 119.8(2) . . ? C3 C4 C5 121.2(2) . . ? C6 C5 C4 120.8(2) . . ? C5 C6 C1 120.3(2) . . ? N1 C7 C8 123.06(18) . . ? N1 C7 C12 118.39(19) . . ? C8 C7 C12 118.55(18) . . ? C13 C8 C7 118.12(18) . . ? C13 C8 C9 122.6(2) . . ? C7 C8 C9 119.27(19) . . ? C10 C9 C8 120.4(2) . . ? C9 C10 C11 120.4(2) . . ? C12 C11 C10 121.1(2) . . ? C11 C12 C7 120.3(2) . . ? C2 C13 C8 119.7(2) . . ? C15 C14 C19 117.5(2) . . ? C15 C14 Br1 121.67(16) . . ? C19 C14 Br1 120.85(16) . . ? F1 C15 C16 118.49(18) . . ? F1 C15 C14 120.05(19) . . ? C16 C15 C14 121.46(19) . . ? F2 C16 C15 120.7(2) . . ? F2 C16 C17 119.2(2) . . ? C15 C16 C17 120.07(19) . . ? F3 C17 C18 120.3(2) . . ? F3 C17 C16 120.2(2) . . ? C18 C17 C16 119.5(2) . . ? F4 C18 C17 119.7(2) . . ? F4 C18 C19 120.44(19) . . ? C17 C18 C19 119.90(19) . . ? F5 C19 C18 118.60(18) . . ? F5 C19 C14 119.80(19) . . ? C18 C19 C14 121.60(19) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.543 _refine_diff_density_min -0.756 _refine_diff_density_rms 0.077