# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Graham Saunders' _publ_contact_author_email g.saunders@waikato.ac.nz _publ_section_title ; On the importance of pi-pi stacking and cation-anion interactions in the construction of non-centrosymmetric networks of bromide salts of imidazolium cations bearing arene and polyfluoroarene rings ; _publ_author_name G.Saunders # Attachment '- Crystal data.docx' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 806231' #TrackingRef '- Crystal data.docx' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H10 F4 N3, Br' _chemical_formula_sum 'C15 H10 Br F4 N3' _chemical_formula_weight 388.17 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' 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 Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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' _cell_length_a 12.7109(3) _cell_length_b 9.5071(3) _cell_length_c 12.7444(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1540.08(8) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 9918 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 28.31 _exptl_crystal_description triangular _exptl_crystal_colour gold _exptl_crystal_size_max 0.670 _exptl_crystal_size_mid 0.600 _exptl_crystal_size_min 0.300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 2.712 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6110 _exptl_absorpt_correction_T_max 0.7458 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36035 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 29.05 _reflns_number_total 4090 _reflns_number_gt 3706 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0260P)^2^+0.0666P] 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 0.008(6) _refine_ls_number_reflns 4090 _refine_ls_number_parameters 208 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0214 _refine_ls_wR_factor_ref 0.0528 _refine_ls_wR_factor_gt 0.0511 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 Br1 Br 0.168836(12) 0.050994(16) 0.39407(2) 0.03619(5) Uani 1 1 d . . . F5 F -0.05264(8) -0.22845(11) 0.39065(13) 0.0469(2) Uani 1 1 d . . . F6 F 0.12381(11) -0.38393(13) 0.37733(14) 0.0653(4) Uani 1 1 d . . . F7 F 0.21239(10) -0.19211(18) 0.06654(12) 0.0633(4) Uani 1 1 d . . . F8 F 0.05247(9) -0.00661(16) 0.07587(9) 0.0431(3) Uani 1 1 d . . . N1 N -0.09366(10) -0.02015(15) 0.23973(12) 0.0244(3) Uani 1 1 d . . . N2 N -0.21923(11) 0.11899(15) 0.19690(12) 0.0275(3) Uani 1 1 d . . . N3 N 0.16670(12) -0.2893(2) 0.22207(17) 0.0472(5) Uani 1 1 d . . . C1 C -0.15223(13) 0.02667(18) 0.15938(14) 0.0270(3) Uani 1 1 d . . . H1 H -0.1464 -0.0012 0.0897 0.032 Uiso 1 1 calc R . . C2 C -0.12620(14) 0.04594(17) 0.33172(13) 0.0292(3) Uani 1 1 d . . . H2 H -0.0988 0.0329 0.3987 0.035 Uiso 1 1 calc R . . C3 C -0.20542(14) 0.13267(19) 0.30423(15) 0.0312(4) Uani 1 1 d . . . H3 H -0.2436 0.1908 0.3489 0.037 Uiso 1 1 calc R . . C4 C -0.00825(12) -0.11518(17) 0.23182(14) 0.0268(3) Uani 1 1 d . . . C5 C 0.01131(14) -0.21401(18) 0.30837(14) 0.0337(4) Uani 1 1 d . . . C6 C 0.10146(17) -0.2955(2) 0.30032(19) 0.0436(5) Uani 1 1 d . . . C7 C 0.14641(14) -0.1980(2) 0.14825(18) 0.0427(5) Uani 1 1 d . . . C8 C 0.06278(13) -0.1066(2) 0.14976(15) 0.0329(4) Uani 1 1 d . . . C9 C -0.29996(14) 0.1951(2) 0.13476(17) 0.0371(4) Uani 1 1 d . . . H9A H -0.2792 0.1970 0.0615 0.045 Uiso 1 1 calc R . . H9B H -0.3050 0.2915 0.1593 0.045 Uiso 1 1 calc R . . C10 C -0.40589(13) 0.12445(19) 0.14499(16) 0.0332(4) Uani 1 1 d . . . C11 C -0.46777(14) 0.1514(2) 0.23166(19) 0.0410(4) Uani 1 1 d . . . H11 H -0.4459 0.2176 0.2808 0.049 Uiso 1 1 calc R . . C12 C -0.56223(16) 0.0809(2) 0.2462(2) 0.0543(6) Uani 1 1 d . . . H12 H -0.6028 0.0982 0.3056 0.065 Uiso 1 1 calc R . . C14 C -0.5372(2) -0.0387(3) 0.0848(3) 0.0642(8) Uani 1 1 d . . . H14 H -0.5623 -0.1009 0.0344 0.077 Uiso 1 1 calc R . . C13 C -0.59500(18) -0.0136(3) 0.1731(3) 0.0601(7) Uani 1 1 d . . . H13 H -0.6578 -0.0618 0.1834 0.072 Uiso 1 1 calc R . . C15 C -0.43974(19) 0.0291(2) 0.0696(2) 0.0471(5) Uani 1 1 d . . . H15 H -0.3991 0.0104 0.0105 0.057 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 Br1 0.04104(9) 0.04171(9) 0.02583(8) 0.00553(9) -0.00302(10) -0.01644(6) F5 0.0513(6) 0.0440(5) 0.0454(6) 0.0145(7) 0.0068(8) 0.0076(4) F6 0.0701(8) 0.0468(6) 0.0790(11) 0.0071(8) -0.0176(9) 0.0242(6) F7 0.0357(6) 0.1005(11) 0.0536(8) -0.0329(8) 0.0128(6) 0.0098(7) F8 0.0369(6) 0.0645(8) 0.0278(6) -0.0016(6) 0.0067(5) 0.0014(6) N1 0.0224(6) 0.0279(7) 0.0229(7) -0.0033(5) 0.0016(6) 0.0011(5) N2 0.0230(6) 0.0297(7) 0.0298(7) 0.0030(6) 0.0006(6) 0.0002(5) N3 0.0348(8) 0.0460(10) 0.0609(13) -0.0240(9) -0.0095(8) 0.0107(7) C1 0.0253(7) 0.0325(8) 0.0232(8) -0.0002(6) 0.0006(6) -0.0039(6) C2 0.0318(8) 0.0336(9) 0.0222(8) -0.0042(6) 0.0011(7) 0.0029(6) C3 0.0304(8) 0.0322(9) 0.0310(9) -0.0040(7) 0.0023(7) 0.0035(7) C4 0.0240(7) 0.0267(8) 0.0297(8) -0.0087(6) -0.0019(6) 0.0000(6) C5 0.0350(9) 0.0279(8) 0.0381(10) -0.0040(7) -0.0011(8) 0.0015(7) C6 0.0411(10) 0.0327(9) 0.0570(13) -0.0077(9) -0.0125(10) 0.0096(8) C7 0.0281(8) 0.0554(12) 0.0444(11) -0.0261(10) 0.0015(8) 0.0026(8) C8 0.0269(8) 0.0431(9) 0.0287(9) -0.0093(7) -0.0008(7) -0.0011(7) C9 0.0273(8) 0.0413(10) 0.0427(11) 0.0136(8) -0.0026(8) 0.0053(7) C10 0.0264(7) 0.0321(9) 0.0412(10) 0.0079(8) -0.0063(7) 0.0049(7) C11 0.0324(9) 0.0377(10) 0.0529(12) 0.0030(9) -0.0006(8) 0.0068(7) C12 0.0307(10) 0.0489(12) 0.0833(18) 0.0161(12) 0.0069(11) 0.0064(9) C14 0.0627(15) 0.0476(14) 0.083(2) 0.0062(12) -0.0432(16) -0.0088(11) C13 0.0317(10) 0.0564(14) 0.092(2) 0.0220(15) -0.0133(13) -0.0053(10) C15 0.0480(11) 0.0480(13) 0.0453(13) 0.0040(10) -0.0172(10) 0.0064(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F5 C5 1.334(2) . ? F6 C6 1.323(3) . ? F7 C7 1.338(3) . ? F8 C8 1.345(2) . ? N1 C1 1.342(2) . ? N1 C2 1.393(2) . ? N1 C4 1.416(2) . ? N2 C1 1.313(2) . ? N2 C3 1.385(2) . ? N2 C9 1.485(2) . ? N3 C6 1.298(3) . ? N3 C7 1.305(3) . ? C2 C3 1.348(3) . ? C4 C5 1.377(3) . ? C4 C8 1.384(3) . ? C5 C6 1.387(3) . ? C7 C8 1.373(3) . ? C9 C10 1.511(3) . ? C10 C11 1.380(3) . ? C10 C15 1.390(3) . ? C11 C12 1.388(3) . ? C12 C13 1.360(4) . ? C14 C13 1.365(5) . ? C14 C15 1.410(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 N1 C2 109.14(14) . . ? C1 N1 C4 125.63(15) . . ? C2 N1 C4 125.13(15) . . ? C1 N2 C3 109.89(15) . . ? C1 N2 C9 125.45(17) . . ? C3 N2 C9 124.65(16) . . ? C6 N3 C7 117.22(17) . . ? N2 C1 N1 107.68(15) . . ? C3 C2 N1 106.20(16) . . ? C2 C3 N2 107.09(15) . . ? C5 C4 C8 117.24(16) . . ? C5 C4 N1 121.55(16) . . ? C8 C4 N1 121.10(16) . . ? F5 C5 C4 121.14(15) . . ? F5 C5 C6 120.28(17) . . ? C4 C5 C6 118.54(18) . . ? N3 C6 F6 117.48(18) . . ? N3 C6 C5 124.0(2) . . ? F6 C6 C5 118.5(2) . . ? N3 C7 F7 117.70(18) . . ? N3 C7 C8 124.3(2) . . ? F7 C7 C8 118.0(2) . . ? F8 C8 C7 120.88(18) . . ? F8 C8 C4 120.48(15) . . ? C7 C8 C4 118.58(19) . . ? N2 C9 C10 110.68(15) . . ? C11 C10 C15 119.90(19) . . ? C11 C10 C9 119.63(19) . . ? C15 C10 C9 120.4(2) . . ? C10 C11 C12 120.7(2) . . ? C13 C12 C11 119.5(2) . . ? C13 C14 C15 120.5(3) . . ? C12 C13 C14 121.0(2) . . ? C10 C15 C14 118.3(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.311 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.042