# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Jesus Valdes-Martinez' _publ_contact_author_email JVALDES@SERVIDOR.UNAM.MX _publ_section_title ; Bottom-up design and construction of a non-centrosymmetric network through pi-pi stacking interactions ; loop_ _publ_author_name 'Jesus Valdes-Martinez' 'Simon Hernandez-Ortega' 'David Morales-Morales' ; J.M.Serrano-Becerra ; # Attachment 'B814639J.cif' data_074mmd05 _database_code_depnum_ccdc_archive 'CCDC 698873' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(2,3,4,5,6-pentafluorobenzyl)-3-benzylimidazolium bromide ; _chemical_name_common '1-(2,3,4,5,6-pentafluorobenzyl)-3-benzylimidazolium bromide' _chemical_melting_point_gt 444 _chemical_melting_point_lt 446 _chemical_formula_moiety 'C17 H12 F5 N2+, Br-' _chemical_formula_sum 'C17 H12 Br F5 N2' _chemical_formula_weight 419.20 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' 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_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.4341(12) _cell_length_b 7.3046(14) _cell_length_c 8.8257(17) _cell_angle_alpha 85.980(4) _cell_angle_beta 88.527(4) _cell_angle_gamma 83.187(4) _cell_volume 410.79(14) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2237 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 30.70 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 1.695 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 2.556 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.5244 _exptl_absorpt_correction_T_max 0.7161 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX AXS CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3387 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2776 _reflns_number_gt 2406 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625' _computing_cell_refinement 'SMART V 5.625' _computing_data_reduction 'SAINT V 6.23C' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V 6.10' _computing_publication_material 'SHELXTL V 6.10' #_solved_by SimonHO _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^)+(0.0383P)^2^] 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 -0.006(7) _refine_ls_number_reflns 2776 _refine_ls_number_parameters 226 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0765 _refine_ls_wR_factor_gt 0.0752 _refine_ls_goodness_of_fit_ref 0.911 _refine_ls_restrained_S_all 0.910 _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 Br Br 0.88614(4) 0.79616(4) 0.70350(4) 0.07038(19) Uani 1 1 d . . . F1 F 0.1388(4) 0.5420(4) 0.3812(3) 0.0797(8) Uani 1 1 d . . . F2 F 0.2301(6) 0.4859(5) 0.0881(3) 0.1026(12) Uani 1 1 d . . . F3 F 0.6176(7) 0.3436(5) 0.0057(3) 0.1121(13) Uani 1 1 d . . . F4 F 0.9125(7) 0.2500(4) 0.2174(5) 0.1021(13) Uani 1 1 d . . . F5 F 0.8223(5) 0.3063(4) 0.5105(4) 0.0872(9) Uani 1 1 d . . . N1 N 0.3187(7) 0.0639(6) 0.8308(4) 0.0464(10) Uani 1 1 d . . . C2 C 0.4447(8) 0.1580(7) 0.7493(5) 0.0481(11) Uani 1 1 d . . . H2 H 0.5825 0.1158 0.7242 0.058 Uiso 1 1 calc R . . N3 N 0.3485(6) 0.3220(5) 0.7074(4) 0.0474(11) Uani 1 1 d . . . C4 C 0.1480(7) 0.3310(6) 0.7631(5) 0.0576(12) Uani 1 1 d . . . H4 H 0.0440 0.4304 0.7499 0.069 Uiso 1 1 calc R . . C5 C 0.1301(7) 0.1700(6) 0.8399(5) 0.0578(12) Uani 1 1 d . . . H5 H 0.0106 0.1361 0.8905 0.069 Uiso 1 1 calc R . . C6 C 0.4352(11) 0.4747(8) 0.6159(6) 0.0602(15) Uani 1 1 d . . . H6A H 0.5634 0.5003 0.6615 0.072 Uiso 1 1 calc R . . H6B H 0.3359 0.5855 0.6171 0.072 Uiso 1 1 calc R . . C7 C 0.4806(7) 0.4282(5) 0.4538(4) 0.0474(10) Uani 1 1 d . . . C8 C 0.3290(7) 0.4700(6) 0.3423(5) 0.0539(11) Uani 1 1 d . . . C9 C 0.3733(9) 0.4409(7) 0.1932(5) 0.0612(12) Uani 1 1 d . . . C10 C 0.5708(11) 0.3696(7) 0.1522(5) 0.0707(15) Uani 1 1 d . . . C11 C 0.7212(9) 0.3248(6) 0.2576(6) 0.0657(13) Uani 1 1 d . . . C12 C 0.6720(8) 0.3536(6) 0.4078(5) 0.0558(11) Uani 1 1 d . . . C13 C 0.3709(7) -0.1242(5) 0.9057(5) 0.0517(10) Uani 1 1 d . . . H13A H 0.4897 -0.1880 0.8535 0.062 Uiso 1 1 calc R . . H13B H 0.2529 -0.1943 0.8989 0.062 Uiso 1 1 calc R . . C14 C 0.4228(7) -0.1136(5) 1.0713(4) 0.0475(10) Uani 1 1 d . . . C15 C 0.6273(7) -0.1537(6) 1.1193(5) 0.0585(11) Uani 1 1 d . . . H15 H 0.7339 -0.1843 1.0492 0.070 Uiso 1 1 calc R . . C16 C 0.6735(8) -0.1484(7) 1.2700(6) 0.0667(14) Uani 1 1 d . . . H16 H 0.8110 -0.1762 1.3018 0.080 Uiso 1 1 calc R . . C17 C 0.5171(10) -0.1024(7) 1.3731(6) 0.0709(15) Uani 1 1 d . . . H17 H 0.5486 -0.0993 1.4751 0.085 Uiso 1 1 calc R . . C18 C 0.3143(9) -0.0607(7) 1.3271(5) 0.0712(14) Uani 1 1 d . . . H18 H 0.2081 -0.0277 1.3969 0.085 Uiso 1 1 calc R . . C19 C 0.2700(8) -0.0684(6) 1.1763(5) 0.0606(12) Uani 1 1 d . . . H19 H 0.1320 -0.0421 1.1452 0.073 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 Br 0.0653(3) 0.0637(3) 0.0793(3) -0.0159(2) -0.0157(2) 0.0143(2) F1 0.0644(19) 0.0780(19) 0.094(2) 0.0023(16) -0.0060(15) -0.0008(15) F2 0.133(3) 0.113(3) 0.0692(18) 0.0180(17) -0.0489(19) -0.050(2) F3 0.178(4) 0.116(3) 0.0548(18) -0.0306(17) 0.033(2) -0.062(3) F4 0.092(3) 0.074(3) 0.138(3) -0.021(3) 0.038(2) -0.001(2) F5 0.076(2) 0.079(2) 0.102(2) 0.0103(17) -0.0286(18) 0.0053(16) N1 0.053(2) 0.046(2) 0.039(2) 0.0035(17) -0.0080(18) -0.0002(19) C2 0.055(3) 0.051(3) 0.036(2) -0.010(2) -0.008(2) 0.006(2) N3 0.065(3) 0.041(3) 0.0364(16) -0.0034(17) -0.0039(18) -0.003(2) C4 0.062(3) 0.053(3) 0.053(3) 0.002(2) -0.016(2) 0.010(2) C5 0.053(3) 0.059(3) 0.060(3) 0.003(2) -0.006(2) 0.000(2) C6 0.085(4) 0.048(3) 0.048(3) -0.007(2) -0.007(3) -0.004(3) C7 0.062(3) 0.035(2) 0.045(2) 0.0025(18) -0.007(2) -0.007(2) C8 0.062(3) 0.040(2) 0.060(3) 0.001(2) -0.006(2) -0.010(2) C9 0.083(4) 0.059(3) 0.046(3) 0.004(2) -0.017(3) -0.025(3) C10 0.110(5) 0.059(3) 0.049(3) -0.012(2) 0.011(3) -0.032(3) C11 0.074(4) 0.046(3) 0.080(4) -0.012(3) 0.017(3) -0.014(3) C12 0.065(3) 0.040(2) 0.062(3) 0.005(2) -0.014(2) -0.008(2) C13 0.061(3) 0.038(2) 0.055(2) 0.0017(19) -0.010(2) 0.0001(19) C14 0.058(3) 0.035(2) 0.049(2) 0.0043(18) -0.007(2) -0.0053(19) C15 0.057(3) 0.053(3) 0.064(3) 0.009(2) -0.003(2) -0.005(2) C16 0.066(3) 0.062(3) 0.073(3) 0.016(3) -0.032(3) -0.018(3) C17 0.109(5) 0.053(3) 0.052(3) 0.007(2) -0.017(3) -0.018(3) C18 0.090(4) 0.060(3) 0.060(3) 0.002(2) 0.001(3) 0.007(3) C19 0.061(3) 0.058(3) 0.059(3) 0.005(2) -0.011(2) 0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C8 1.320(5) . ? F2 C9 1.321(5) . ? F3 C10 1.342(5) . ? F4 C11 1.336(7) . ? F5 C12 1.341(5) . ? N1 C2 1.296(6) . ? N1 C5 1.364(6) . ? N1 C13 1.487(5) . ? C2 N3 1.315(7) . ? N3 C4 1.365(6) . ? N3 C6 1.485(7) . ? C4 C5 1.331(6) . ? C6 C7 1.507(7) . ? C7 C12 1.351(6) . ? C7 C8 1.396(6) . ? C8 C9 1.365(6) . ? C9 C10 1.365(7) . ? C10 C11 1.355(8) . ? C11 C12 1.380(7) . ? C13 C14 1.517(5) . ? C14 C19 1.361(6) . ? C14 C15 1.384(6) . ? C15 C16 1.374(6) . ? C16 C17 1.367(8) . ? C17 C18 1.370(7) . ? C18 C19 1.374(6) . ? 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 C2 N1 C5 107.9(4) . . ? C2 N1 C13 126.4(4) . . ? C5 N1 C13 125.7(4) . . ? N1 C2 N3 109.8(4) . . ? C2 N3 C4 107.9(4) . . ? C2 N3 C6 127.9(4) . . ? C4 N3 C6 124.3(4) . . ? C5 C4 N3 106.7(4) . . ? C4 C5 N1 107.6(4) . . ? N3 C6 C7 111.9(4) . . ? C12 C7 C8 116.9(4) . . ? C12 C7 C6 121.8(4) . . ? C8 C7 C6 121.2(5) . . ? F1 C8 C9 119.0(4) . . ? F1 C8 C7 119.4(4) . . ? C9 C8 C7 121.6(5) . . ? F2 C9 C10 119.8(5) . . ? F2 C9 C8 121.0(5) . . ? C10 C9 C8 119.1(4) . . ? F3 C10 C11 119.3(6) . . ? F3 C10 C9 119.8(5) . . ? C11 C10 C9 120.9(4) . . ? F4 C11 C10 120.6(5) . . ? F4 C11 C12 120.4(5) . . ? C10 C11 C12 118.9(5) . . ? F5 C12 C7 119.5(4) . . ? F5 C12 C11 118.0(5) . . ? C7 C12 C11 122.5(4) . . ? N1 C13 C14 110.8(3) . . ? C19 C14 C15 118.5(4) . . ? C19 C14 C13 121.1(4) . . ? C15 C14 C13 120.4(4) . . ? C16 C15 C14 120.3(4) . . ? C17 C16 C15 119.9(5) . . ? C16 C17 C18 120.4(5) . . ? C17 C18 C19 119.1(5) . . ? C14 C19 C18 121.7(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.509 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.050