# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm #TrackingRef '- dwb0810m.cif' _journal_coden_Cambridge 1350 _publ_contact_author_name 'Duncan W. Bruce' _publ_contact_author_address ;Department of Chemistry University of York Heslington YORK YO10 5DD ; _publ_contact_author_email db519@york.ac.uk _publ_contact_author_phone '+44 1904 434085' loop_ _publ_author_name _publ_author_address D.W.Bruce ;Department of Chemistry University of York Heslington YORK YO10 5DD ; L.C.Roper ;Department of Chemistry University of York Heslington YORK YO10 5DD ; C.Prasang ;Department of Chemistry University of York Heslington YORK YO10 5DD ; A.C.Whitwood ;Department of Chemistry University of York Heslington YORK YO10 5DD ; data_dwb0810m _database_code_depnum_ccdc_archive 'CCDC 774574' #TrackingRef '- dwb0810m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 Br I N4' _chemical_formula_weight 527.24 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' I I -0.4742 1.8119 '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 P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5738(7) _cell_length_b 7.7425(7) _cell_length_c 9.4012(8) _cell_angle_alpha 109.086(2) _cell_angle_beta 95.635(2) _cell_angle_gamma 99.598(2) _cell_volume 506.74(8) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2727 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 28.28 _exptl_crystal_description shard _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.728 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 3.563 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.550 _exptl_absorpt_correction_T_max 0.752 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _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 '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 3677 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2490 _reflns_number_gt 2378 _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, 1997)' _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. The orientation of the C6H4BrI was disordered by inversion about the cell centre. The C-Br bond was restrained to 1.899 angstroms, the C-I bond restrained to 2.095 angstroms and the Br and I ADP constrained to be equal. ; _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^)+(0.0327P)^2^+0.3386P] 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 2490 _refine_ls_number_parameters 124 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0259 _refine_ls_R_factor_gt 0.0245 _refine_ls_wR_factor_ref 0.0631 _refine_ls_wR_factor_gt 0.0624 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.047 _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 C1 C 0.3568(3) 0.4370(3) 0.5640(2) 0.0181(4) Uani 1 1 d D . . C2 C 0.3218(3) 0.4874(3) 0.4363(3) 0.0198(4) Uani 1 1 d . . . H2 H 0.2029 0.4787 0.3940 0.024 Uiso 1 1 calc R . . C3 C 0.5337(3) 0.4489(3) 0.6275(3) 0.0202(5) Uani 1 1 d . . . H3 H 0.5558 0.4146 0.7125 0.024 Uiso 1 1 calc R . . Br1 Br 0.1589(8) 0.3525(10) 0.6529(8) 0.0153(2) Uani 0.50 1 d PD A 1 I1 I 0.1434(5) 0.3393(6) 0.6597(5) 0.0153(2) Uani 0.50 1 d PD A 2 C4 C 0.7101(3) 0.0656(4) 0.6899(3) 0.0231(5) Uani 1 1 d . . . H4 H 0.7459 0.0014 0.5989 0.028 Uiso 1 1 calc R . . C5 C 0.5345(3) 0.0082(3) 0.7076(3) 0.0205(5) Uani 1 1 d . . . H5 H 0.4573 -0.0927 0.6313 0.025 Uiso 1 1 calc R . . C6 C 0.4719(3) 0.1038(3) 0.8426(3) 0.0169(4) Uani 1 1 d . . . C7 C 0.6026(3) 0.2514(3) 0.9531(3) 0.0189(4) Uani 1 1 d . . . H7 H 0.5720 0.3187 1.0456 0.023 Uiso 1 1 calc R . . C8 C 0.7751(3) 0.2943(3) 0.9226(3) 0.0214(5) Uani 1 1 d . . . H8 H 0.8574 0.3920 0.9975 0.026 Uiso 1 1 calc R . . C9 C 0.1691(3) -0.0966(4) 0.7513(3) 0.0256(5) Uani 1 1 d . . . H9A H 0.1519 -0.0715 0.6580 0.038 Uiso 1 1 calc R . . H9C H 0.0553 -0.1114 0.7875 0.038 Uiso 1 1 calc R . . H9B H 0.2143 -0.2093 0.7332 0.038 Uiso 1 1 calc R . . C10 C 0.2374(3) 0.1685(4) 1.0009(3) 0.0214(5) Uani 1 1 d . . . H10C H 0.2929 0.1474 1.0883 0.032 Uiso 1 1 calc R . . H10A H 0.1079 0.1323 0.9897 0.032 Uiso 1 1 calc R . . H10B H 0.2710 0.2987 1.0145 0.032 Uiso 1 1 calc R . . N1 N 0.8347(3) 0.2066(3) 0.7931(2) 0.0230(4) Uani 1 1 d . . . N2 N 0.2989(3) 0.0582(3) 0.8651(2) 0.0195(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 C1 0.0215(11) 0.0151(10) 0.0160(10) 0.0037(8) 0.0039(8) 0.0030(8) C2 0.0190(11) 0.0201(11) 0.0187(11) 0.0058(9) 0.0005(9) 0.0037(8) C3 0.0256(12) 0.0199(11) 0.0160(10) 0.0078(9) 0.0013(9) 0.0054(9) Br1 0.0162(6) 0.0151(6) 0.0155(4) 0.0073(3) 0.0063(3) -0.0002(4) I1 0.0162(6) 0.0151(6) 0.0155(4) 0.0073(3) 0.0063(3) -0.0002(4) C4 0.0268(12) 0.0247(12) 0.0212(11) 0.0089(10) 0.0093(9) 0.0097(10) C5 0.0246(12) 0.0187(11) 0.0162(10) 0.0045(9) 0.0025(9) 0.0032(9) C6 0.0199(11) 0.0161(10) 0.0158(10) 0.0078(8) 0.0021(8) 0.0034(8) C7 0.0220(11) 0.0177(10) 0.0161(10) 0.0056(8) 0.0033(8) 0.0023(8) C8 0.0202(11) 0.0230(12) 0.0207(11) 0.0090(9) 0.0021(9) 0.0016(9) C9 0.0218(12) 0.0213(12) 0.0270(12) 0.0043(10) 0.0010(10) -0.0030(9) C10 0.0192(11) 0.0252(12) 0.0216(11) 0.0091(9) 0.0080(9) 0.0054(9) N1 0.0213(10) 0.0273(11) 0.0233(10) 0.0121(9) 0.0073(8) 0.0039(8) N2 0.0199(9) 0.0182(9) 0.0183(9) 0.0051(8) 0.0044(7) 0.0001(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 C1 C3 1.388(3) . ? C1 C2 1.393(3) . ? C1 Br1 1.911(4) . ? C1 I1 2.078(3) . ? C2 C3 1.394(3) 2_666 ? C2 H2 0.9300 . ? C3 C2 1.394(3) 2_666 ? C3 H3 0.9300 . ? C4 N1 1.345(3) . ? C4 C5 1.374(4) . ? C4 H4 0.9300 . ? C5 C6 1.416(3) . ? C5 H5 0.9300 . ? C6 N2 1.355(3) . ? C6 C7 1.417(3) . ? C7 C8 1.375(3) . ? C7 H7 0.9300 . ? C8 N1 1.347(3) . ? C8 H8 0.9300 . ? C9 N2 1.452(3) . ? C9 H9A 0.9600 . ? C9 H9C 0.9600 . ? C9 H9B 0.9600 . ? C10 N2 1.453(3) . ? C10 H10C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? 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 C3 C1 C2 120.7(2) . . ? C3 C1 Br1 119.8(3) . . ? C2 C1 Br1 119.5(3) . . ? C3 C1 I1 119.2(2) . . ? C2 C1 I1 120.1(2) . . ? Br1 C1 I1 1.3(4) . . ? C1 C2 C3 119.5(2) . 2_666 ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 2_666 . ? C1 C3 C2 119.8(2) . 2_666 ? C1 C3 H3 120.1 . . ? C2 C3 H3 120.1 2_666 . ? N1 C4 C5 125.5(2) . . ? N1 C4 H4 117.2 . . ? C5 C4 H4 117.2 . . ? C4 C5 C6 119.5(2) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? N2 C6 C5 122.5(2) . . ? N2 C6 C7 122.1(2) . . ? C5 C6 C7 115.4(2) . . ? C8 C7 C6 119.5(2) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.3 . . ? N1 C8 C7 125.4(2) . . ? N1 C8 H8 117.3 . . ? C7 C8 H8 117.3 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? H9C C9 H9B 109.5 . . ? N2 C10 H10C 109.5 . . ? N2 C10 H10A 109.5 . . ? H10C C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10C C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 N1 C8 114.5(2) . . ? C6 N2 C9 120.8(2) . . ? C6 N2 C10 120.5(2) . . ? C9 N2 C10 118.6(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 C3 C1 C2 C3 -0.2(4) . . . 2_666 ? Br1 C1 C2 C3 179.3(3) . . . 2_666 ? I1 C1 C2 C3 -179.4(2) . . . 2_666 ? C2 C1 C3 C2 0.2(4) . . . 2_666 ? Br1 C1 C3 C2 -179.3(3) . . . 2_666 ? I1 C1 C3 C2 179.4(2) . . . 2_666 ? N1 C4 C5 C6 1.4(4) . . . . ? C4 C5 C6 N2 177.9(2) . . . . ? C4 C5 C6 C7 -2.0(3) . . . . ? N2 C6 C7 C8 -178.5(2) . . . . ? C5 C6 C7 C8 1.4(3) . . . . ? C6 C7 C8 N1 -0.1(4) . . . . ? C5 C4 N1 C8 0.0(4) . . . . ? C7 C8 N1 C4 -0.6(4) . . . . ? C5 C6 N2 C9 1.7(4) . . . . ? C7 C6 N2 C9 -178.5(2) . . . . ? C5 C6 N2 C10 -175.7(2) . . . . ? C7 C6 N2 C10 4.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.851 _refine_diff_density_min -0.800 _refine_diff_density_rms 0.098