# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof Frieder Jaekle' _publ_contact_author_address ; Rutgers University 73 Warren Street Newark 07102 UNITED STATES OF AMERICA ; _publ_contact_author_email FJAEKLE@ANDROMEDA.RUTGERS.EDU _publ_section_title ; Competition of Cuprophilic and p-Stacking Interactions in the Formation of Supramolecular Stacks from Organocopper Complexes ; loop_ _publ_author_name 'Frieder Jaekle' 'Arnold Rheingold' 'Anand Sundararaman' 'Lev N. Zakharov' #===END data_fjak04 _database_code_depnum_ccdc_archive 'CCDC 219363' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H8 Cu2 F10 N2' _chemical_formula_weight 617.38 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 9.2876(18) _cell_length_b 5.0328(10) _cell_length_c 22.316(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.567(4) _cell_angle_gamma 90.00 _cell_volume 1042.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 219(2) _cell_measurement_reflns_used 4080 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 28.35 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.968 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 2.144 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5380 _exptl_absorpt_correction_T_max 0.8821 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 219(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7363 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.35 _reflns_number_total 2511 _reflns_number_gt 2009 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2511 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1020 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 1.228 _refine_ls_restrained_S_all 1.228 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.002 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 Cu1 Cu 0.82583(3) 0.24684(4) 0.117126(13) 0.04476(14) Uani 1 1 d . . . F2 F 1.0596(2) -0.1336(4) 0.06724(6) 0.0719(5) Uani 1 1 d . . . F3 F 1.20888(17) -0.5266(4) 0.12255(8) 0.0790(5) Uani 1 1 d . . . F4 F 1.16507(16) -0.6435(3) 0.23855(7) 0.0659(5) Uani 1 1 d . . . F5 F 0.97801(18) -0.3518(3) 0.30077(6) 0.0625(4) Uani 1 1 d . . . F6 F 0.83252(15) 0.0478(3) 0.24791(6) 0.0561(4) Uani 1 1 d . . . N1 N 0.7126(2) 0.5137(3) 0.07715(8) 0.0406(4) Uani 1 1 d . . . C1 C 0.9365(2) -0.0258(4) 0.15484(9) 0.0358(5) Uani 1 1 d . . . C2 C 1.0348(3) -0.1796(5) 0.12621(10) 0.0430(5) Uani 1 1 d . . . C3 C 1.1124(2) -0.3845(5) 0.15269(11) 0.0457(5) Uani 1 1 d . . . C4 C 1.0918(2) -0.4440(4) 0.21118(11) 0.0422(5) Uani 1 1 d . . . C5 C 0.9962(3) -0.2972(4) 0.24255(10) 0.0392(5) Uani 1 1 d . . . C6 C 0.9226(2) -0.0937(4) 0.21384(9) 0.0354(5) Uani 1 1 d . . . C7 C 0.7395(3) 0.5890(5) 0.02194(11) 0.0565(7) Uani 1 1 d . . . H7A H 0.8169 0.5087 0.0031 0.068 Uiso 1 1 calc R . . C8 C 0.6602(3) 0.7787(5) -0.00929(12) 0.0552(7) Uani 1 1 d . . . H8A H 0.6848 0.8262 -0.0483 0.066 Uiso 1 1 calc R . . C9 C 0.5450(2) 0.8990(4) 0.01626(8) 0.0326(4) Uani 1 1 d . . . C10 C 0.5191(3) 0.8219(5) 0.07426(11) 0.0518(6) Uani 1 1 d . . . H10A H 0.4427 0.8992 0.0943 0.062 Uiso 1 1 calc R . . C11 C 0.6038(3) 0.6338(6) 0.10261(11) 0.0560(7) Uani 1 1 d . . . H11A H 0.5840 0.5873 0.1422 0.067 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 Cu1 0.0527(2) 0.03619(19) 0.0442(2) 0.00616(11) -0.01099(15) 0.00129(11) F2 0.0878(12) 0.0897(12) 0.0399(8) 0.0056(8) 0.0232(8) -0.0005(10) F3 0.0615(10) 0.0860(12) 0.0917(13) -0.0165(9) 0.0278(9) 0.0229(8) F4 0.0562(9) 0.0475(8) 0.0917(12) 0.0087(8) -0.0235(8) 0.0139(7) F5 0.0830(11) 0.0697(9) 0.0345(7) 0.0141(7) -0.0026(7) 0.0017(8) F6 0.0618(9) 0.0594(8) 0.0478(8) -0.0086(6) 0.0114(7) 0.0169(7) N1 0.0497(11) 0.0354(9) 0.0357(10) 0.0009(7) -0.0069(8) -0.0010(8) C1 0.0384(11) 0.0330(10) 0.0357(11) 0.0011(8) -0.0029(9) -0.0042(8) C2 0.0463(14) 0.0490(12) 0.0341(11) 0.0009(10) 0.0063(10) -0.0068(10) C3 0.0340(12) 0.0474(13) 0.0563(15) -0.0092(11) 0.0094(10) 0.0026(9) C4 0.0346(12) 0.0374(11) 0.0537(14) 0.0008(9) -0.0090(10) 0.0028(9) C5 0.0441(13) 0.0399(11) 0.0330(11) 0.0039(9) -0.0046(9) -0.0041(9) C6 0.0354(11) 0.0343(10) 0.0363(11) -0.0039(8) 0.0008(9) 0.0012(8) C7 0.0647(17) 0.0592(15) 0.0466(14) 0.0091(12) 0.0120(12) 0.0248(13) C8 0.0665(17) 0.0634(16) 0.0372(13) 0.0176(11) 0.0186(12) 0.0258(13) C9 0.0424(12) 0.0293(9) 0.0257(9) -0.0020(8) -0.0010(8) -0.0024(8) C10 0.0598(16) 0.0651(14) 0.0312(11) 0.0097(11) 0.0097(11) 0.0207(12) C11 0.0698(18) 0.0653(17) 0.0329(12) 0.0145(12) 0.0036(12) 0.0104(14) _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 Cu1 C1 1.890(2) . ? Cu1 N1 1.9028(17) . ? F2 C2 1.366(3) . ? F3 C3 1.349(3) . ? F4 C4 1.344(2) . ? F5 C5 1.346(3) . ? F6 C6 1.357(2) . ? N1 C7 1.324(3) . ? N1 C11 1.327(3) . ? C1 C6 1.372(3) . ? C1 C2 1.376(3) . ? C2 C3 1.376(4) . ? C3 C4 1.361(3) . ? C4 C5 1.371(3) . ? C5 C6 1.374(3) . ? C7 C8 1.376(3) . ? C8 C9 1.375(3) . ? C9 C10 1.383(3) . ? C9 C9 1.485(4) 3_675 ? C10 C11 1.368(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Cu1 N1 178.17(8) . . ? C7 N1 C11 116.56(19) . . ? C7 N1 Cu1 121.01(16) . . ? C11 N1 Cu1 122.42(16) . . ? C6 C1 C2 113.50(19) . . ? C6 C1 Cu1 122.37(16) . . ? C2 C1 Cu1 124.11(16) . . ? F2 C2 C1 119.7(2) . . ? F2 C2 C3 115.6(2) . . ? C1 C2 C3 124.6(2) . . ? F3 C3 C4 119.1(2) . . ? F3 C3 C2 122.0(2) . . ? C4 C3 C2 118.9(2) . . ? F4 C4 C3 120.7(2) . . ? F4 C4 C5 119.8(2) . . ? C3 C4 C5 119.6(2) . . ? F5 C5 C6 121.4(2) . . ? F5 C5 C4 119.7(2) . . ? C6 C5 C4 118.9(2) . . ? F6 C6 C1 119.61(18) . . ? F6 C6 C5 115.88(19) . . ? C1 C6 C5 124.5(2) . . ? N1 C7 C8 123.4(2) . . ? C9 C8 C7 120.3(2) . . ? C8 C9 C10 115.8(2) . . ? C8 C9 C9 122.0(2) . 3_675 ? C10 C9 C9 122.1(2) . 3_675 ? C11 C10 C9 120.4(2) . . ? N1 C11 C10 123.4(2) . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.432 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.069 #===END #===END data_fjak03 _database_code_depnum_ccdc_archive 'CCDC 219364' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H8 Cu2 F10 N2' _chemical_formula_weight 617.38 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fddd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 8.071(2) _cell_length_b 11.127(3) _cell_length_c 48.264(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4335(2) _cell_formula_units_Z 8 _cell_measurement_temperature 219(2) _cell_measurement_reflns_used 3139 _cell_measurement_theta_min 3.15 _cell_measurement_theta_max 27.91 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.892 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2416 _exptl_absorpt_coefficient_mu 2.062 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7473 _exptl_absorpt_correction_T_max 0.9039 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 219(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5700 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -63 _diffrn_reflns_limit_l_max 64 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 28.31 _reflns_number_total 1317 _reflns_number_gt 1010 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1317 _refine_ls_number_parameters 85 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1255 _refine_ls_goodness_of_fit_ref 1.401 _refine_ls_restrained_S_all 1.401 _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 Cu1 Cu 0.6250 0.6250 0.012405(10) 0.0467(2) Uani 1 2 d S . . F2 F 0.3611(2) 0.7168(2) -0.02927(5) 0.0736(7) Uani 1 1 d . . . F3 F 0.3656(3) 0.7178(2) -0.08499(5) 0.0774(7) Uani 1 1 d . . . F4 F 0.6250 0.6250 -0.11256(5) 0.0684(9) Uani 1 2 d S . . N1 N 0.6250 0.6250 0.05180(7) 0.0371(7) Uani 1 2 d S . . C1 C 0.6250 0.6250 -0.02655(9) 0.0400(9) Uani 1 2 d S . . C2 C 0.4969(4) 0.6704(3) -0.04224(6) 0.0426(7) Uani 1 1 d . . . C3 C 0.4937(4) 0.6712(3) -0.07049(6) 0.0457(7) Uani 1 1 d . . . C4 C 0.6250 0.6250 -0.08492(9) 0.0446(10) Uani 1 2 d S . . C5 C 0.4932(4) 0.6645(3) 0.06631(6) 0.0393(7) Uani 1 1 d . . . H5A H 0.4006 0.6932 0.0565 0.047 Uiso 1 1 calc R . . C6 C 0.4884(3) 0.6647(3) 0.09474(6) 0.0353(6) Uani 1 1 d . . . H6A H 0.3931 0.6916 0.1041 0.042 Uiso 1 1 calc R . . C7 C 0.6250 0.6250 0.10971(8) 0.0322(8) Uani 1 2 d S . . 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 Cu1 0.0576(4) 0.0607(4) 0.0219(3) 0.000 0.000 0.0042(3) F2 0.0528(13) 0.1102(19) 0.0580(14) 0.0009(12) 0.0122(10) 0.0303(11) F3 0.0736(15) 0.0979(18) 0.0609(15) 0.0126(13) -0.0289(11) 0.0229(12) F4 0.115(3) 0.0674(18) 0.0224(13) 0.000 0.000 -0.0108(17) N1 0.0450(19) 0.0446(18) 0.0216(16) 0.000 0.000 -0.0076(15) C1 0.042(2) 0.046(2) 0.032(2) 0.000 0.000 -0.0057(17) C2 0.0387(16) 0.0528(17) 0.0364(16) -0.0001(13) 0.0038(13) 0.0052(13) C3 0.0477(18) 0.0510(17) 0.0385(16) 0.0059(13) -0.0110(14) 0.0016(14) C4 0.066(3) 0.041(2) 0.0272(19) 0.000 0.000 -0.011(2) C5 0.0401(16) 0.0458(16) 0.0322(15) 0.0014(12) -0.0070(12) 0.0018(11) C6 0.0316(14) 0.0453(15) 0.0291(14) -0.0009(11) -0.0014(11) 0.0044(10) C7 0.0320(18) 0.0398(19) 0.0249(19) 0.000 0.000 -0.0039(15) _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 Cu1 C1 1.880(4) . ? Cu1 N1 1.902(3) . ? F2 C2 1.364(3) . ? F3 C3 1.352(4) . ? F4 C4 1.334(5) . ? N1 C5 1.347(3) 14 ? N1 C5 1.347(3) . ? C1 C2 1.378(4) . ? C1 C2 1.378(4) 14 ? C2 C3 1.364(4) . ? C3 C4 1.368(4) . ? C4 C3 1.368(4) 14 ? C5 C6 1.373(4) . ? C6 C7 1.390(3) . ? C7 C6 1.390(3) 14 ? C7 C7 1.476(7) 11_554 ? 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 Cu1 N1 180.0 . . ? C5 N1 C5 117.4(3) 14 . ? C5 N1 Cu1 121.31(17) 14 . ? C5 N1 Cu1 121.31(17) . . ? C2 C1 C2 113.3(4) . 14 ? C2 C1 Cu1 123.34(19) . . ? C2 C1 Cu1 123.34(19) 14 . ? C3 C2 F2 116.2(3) . . ? C3 C2 C1 124.5(3) . . ? F2 C2 C1 119.3(3) . . ? F3 C3 C2 122.3(3) . . ? F3 C3 C4 118.2(3) . . ? C2 C3 C4 119.5(3) . . ? F4 C4 C3 120.6(2) . 14 ? F4 C4 C3 120.6(2) . . ? C3 C4 C3 118.8(4) 14 . ? N1 C5 C6 122.8(3) . . ? C5 C6 C7 119.8(3) . . ? C6 C7 C6 117.4(3) . 14 ? C6 C7 C7 121.30(17) . 11_554 ? C6 C7 C7 121.30(17) 14 11_554 ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.724 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.103 data_fjak19 _database_code_depnum_ccdc_archive 'CCDC 250638' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H5 Cu F5 N' _chemical_formula_weight 309.70 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x, -y+1/2, -z' '-x, -y, -z' 'x, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x, y-1/2, z' _cell_length_a 9.8916(10) _cell_length_b 18.9476(19) _cell_length_c 5.7848(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1084.20(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.897 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 2.061 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4927 _exptl_absorpt_correction_T_max 0.5768 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8592 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0146 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1365 _reflns_number_gt 1252 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.2500P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1365 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0758 _refine_ls_wR_factor_gt 0.0739 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.005 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 Cu1 Cu 0.25583(2) 0.249809(10) 0.2500 0.02199(13) Uani 1 2 d S . . F2 F 0.27436(11) 0.41623(6) 0.2500 0.0266(3) Uani 1 2 d S . . F3 F 0.07526(12) 0.51255(5) 0.2500 0.0307(3) Uani 1 2 d S . . F4 F -0.18787(12) 0.47122(6) 0.2500 0.0368(3) Uani 1 2 d S . . F5 F -0.25032(10) 0.33095(7) 0.2500 0.0340(3) Uani 1 2 d S . . F6 F -0.05398(11) 0.23397(6) 0.2500 0.0269(3) Uani 1 2 d S . . N1 N 0.39595(15) 0.18105(8) 0.2500 0.0208(3) Uani 1 2 d S . . C1 C 0.11990(18) 0.32001(9) 0.2500 0.0195(4) Uani 1 2 d S . . C2 C 0.14440(18) 0.39200(10) 0.2500 0.0200(4) Uani 1 2 d S . . C3 C 0.04470(19) 0.44305(9) 0.2500 0.0228(4) Uani 1 2 d S . . C4 C -0.08870(19) 0.42257(10) 0.2500 0.0256(4) Uani 1 2 d S . . C5 C -0.12023(19) 0.35167(11) 0.2500 0.0240(4) Uani 1 2 d S . . C6 C -0.01635(19) 0.30291(9) 0.2500 0.0205(4) Uani 1 2 d S . . C7 C 0.52798(19) 0.20036(10) 0.2500 0.0241(4) Uani 1 2 d S . . H7A H 0.5494 0.2492 0.2500 0.029 Uiso 1 2 calc SR . . C8 C 0.6325(2) 0.15216(11) 0.2500 0.0280(4) Uani 1 2 d S . . H8A H 0.7239 0.1676 0.2500 0.034 Uiso 1 2 calc SR . . C9 C 0.6016(2) 0.08085(11) 0.2500 0.0312(5) Uani 1 2 d S . . H9A H 0.6716 0.0465 0.2500 0.037 Uiso 1 2 calc SR . . C10 C 0.4675(2) 0.06032(10) 0.2500 0.0278(4) Uani 1 2 d S . . H10A H 0.4441 0.0117 0.2500 0.033 Uiso 1 2 calc SR . . C11 C 0.3678(2) 0.11156(9) 0.2500 0.0228(4) Uani 1 2 d S . . H11A H 0.2759 0.0971 0.2500 0.027 Uiso 1 2 calc SR . . 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 Cu1 0.01831(18) 0.01793(18) 0.0297(2) 0.000 0.000 0.00256(8) F2 0.0197(5) 0.0242(6) 0.0358(6) 0.000 0.000 -0.0038(4) F3 0.0365(7) 0.0164(5) 0.0393(7) 0.000 0.000 0.0021(4) F4 0.0273(6) 0.0342(6) 0.0490(7) 0.000 0.000 0.0154(5) F5 0.0161(6) 0.0448(8) 0.0412(8) 0.000 0.000 -0.0036(4) F6 0.0290(6) 0.0213(5) 0.0303(6) 0.000 0.000 -0.0064(4) N1 0.0193(8) 0.0187(7) 0.0244(7) 0.000 0.000 0.0004(6) C1 0.0189(8) 0.0204(8) 0.0193(8) 0.000 0.000 0.0019(6) C2 0.0150(8) 0.0227(8) 0.0222(8) 0.000 0.000 -0.0006(7) C3 0.0275(9) 0.0160(8) 0.0249(9) 0.000 0.000 0.0015(7) C4 0.0215(9) 0.0259(9) 0.0295(10) 0.000 0.000 0.0095(7) C5 0.0165(8) 0.0306(9) 0.0248(9) 0.000 0.000 -0.0014(7) C6 0.0224(9) 0.0192(8) 0.0200(8) 0.000 0.000 -0.0016(7) C7 0.0227(9) 0.0207(8) 0.0287(9) 0.000 0.000 -0.0030(7) C8 0.0178(9) 0.0338(10) 0.0323(10) 0.000 0.000 -0.0019(8) C9 0.0245(10) 0.0300(10) 0.0390(11) 0.000 0.000 0.0103(8) C10 0.0276(10) 0.0196(8) 0.0360(10) 0.000 0.000 0.0010(7) C11 0.0208(8) 0.0200(8) 0.0276(9) 0.000 0.000 -0.0008(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 Cu1 C1 1.8913(17) . ? Cu1 N1 1.9022(15) . ? Cu1 Cu1 2.8924(3) 7_566 ? Cu1 Cu1 2.8924(3) 7_565 ? F2 C2 1.365(2) . ? F3 C3 1.351(2) . ? F4 C4 1.346(2) . ? F5 C5 1.345(2) . ? F6 C6 1.3583(19) . ? N1 C11 1.346(2) . ? N1 C7 1.356(2) . ? C1 C6 1.386(3) . ? C1 C2 1.385(2) . ? C2 C3 1.381(3) . ? C3 C4 1.375(3) . ? C4 C5 1.379(3) . ? C5 C6 1.382(3) . ? C7 C8 1.379(3) . ? C8 C9 1.385(3) . ? C9 C10 1.382(3) . ? C10 C11 1.384(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 Cu1 N1 178.54(6) . . ? C1 Cu1 Cu1 89.900(5) . 7_566 ? N1 Cu1 Cu1 90.097(5) . 7_566 ? C1 Cu1 Cu1 89.900(5) . 7_565 ? N1 Cu1 Cu1 90.097(5) . 7_565 ? Cu1 Cu1 Cu1 179.716(15) 7_566 7_565 ? C11 N1 C7 117.58(16) . . ? C11 N1 Cu1 121.30(13) . . ? C7 N1 Cu1 121.11(12) . . ? C6 C1 C2 113.59(16) . . ? C6 C1 Cu1 121.80(13) . . ? C2 C1 Cu1 124.61(14) . . ? F2 C2 C3 115.90(16) . . ? F2 C2 C1 119.73(16) . . ? C3 C2 C1 124.37(17) . . ? F3 C3 C4 119.31(16) . . ? F3 C3 C2 121.52(17) . . ? C4 C3 C2 119.17(16) . . ? F4 C4 C3 120.40(17) . . ? F4 C4 C5 120.14(17) . . ? C3 C4 C5 119.45(16) . . ? F5 C5 C6 121.07(17) . . ? F5 C5 C4 120.04(17) . . ? C6 C5 C4 118.89(17) . . ? F6 C6 C5 116.06(16) . . ? F6 C6 C1 119.42(16) . . ? C5 C6 C1 124.52(17) . . ? N1 C7 C8 122.87(17) . . ? C7 C8 C9 118.74(18) . . ? C10 C9 C8 119.07(17) . . ? C11 C10 C9 119.11(18) . . ? N1 C11 C10 122.63(18) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.522 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.136