Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal SOciety of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Milko van der Boom' _publ_contact_author_address ; Organic Chemistry Weizmann Institute of Science Herzl st 26 Rehovot 76100 ISRAEL ; _publ_contact_author_email MILKO.VANDERBOOM@WEIZMANN.AC.IL _publ_section_title ; Design, synthesis and crystal structure of a multiple donor-acceptor halogen bonded stilbazole: assembly of unimolecular interconnected helices ; loop_ _publ_author_name 'M.van der Boom' 'Andre C. Lucassen' 'Linda Shimon' 'Tatiana Zubkov' data_v32 _database_code_depnum_ccdc_archive 'CCDC 637114' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H6 F3 I2 N' _chemical_formula_weight 486.99 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.2290(8) _cell_length_b 14.112(3) _cell_length_c 23.312(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1391.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1909 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 4.539 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.2099 _exptl_absorpt_correction_T_max 0.8049 _exptl_absorpt_process_details ? _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_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _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 1897 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1897 _reflns_number_gt 1654 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect package (Bruker Nonius)' _computing_cell_refinement HKL _computing_data_reduction HKL _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^)+(0.0262P)^2^+1.3859P] 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 0.59(5) _refine_ls_number_reflns 1897 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0613 _refine_ls_wR_factor_gt 0.0588 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 -0.05474(10) -0.18602(3) -0.353294(19) 0.01765(11) Uani 1 1 d . . . I2 I -0.67455(10) -0.44027(3) -0.17751(2) 0.02031(12) Uani 1 1 d . . . F1 F -0.3891(10) -0.2774(3) -0.09922(16) 0.0249(10) Uani 1 1 d . . . F2 F -0.4465(10) -0.3536(3) -0.29451(16) 0.0220(9) Uani 1 1 d . . . F3 F 0.1380(9) -0.0879(3) -0.23503(17) 0.0236(10) Uani 1 1 d . . . C1 C 0.2685(18) 0.0077(5) -0.0635(3) 0.0217(17) Uani 1 1 d . . . C2 C 0.180(2) -0.0174(6) -0.0080(3) 0.034(2) Uani 1 1 d . . . H2 H 0.0629 -0.0738 -0.0016 0.041 Uiso 1 1 calc R . . C3 C 0.2623(18) 0.0394(5) 0.0372(3) 0.030(2) Uani 1 1 d . . . H3 H 0.1928 0.0210 0.0744 0.036 Uiso 1 1 calc R . . N1 N 0.4336(16) 0.1192(4) 0.0330(3) 0.0257(14) Uani 1 1 d . . . C4 C 0.5260(19) 0.1412(5) -0.0198(3) 0.0235(17) Uani 1 1 d . . . H4 H 0.6529 0.1961 -0.0246 0.028 Uiso 1 1 calc R . . C5 C 0.450(2) 0.0892(5) -0.0682(3) 0.0274(17) Uani 1 1 d . . . H5 H 0.5216 0.1095 -0.1048 0.033 Uiso 1 1 calc R . . C6 C 0.1790(17) -0.0468(5) -0.1156(3) 0.0217(16) Uani 1 1 d . . . H6 H 0.2685 -0.0280 -0.1512 0.026 Uiso 1 1 calc R . . C7 C -0.0166(18) -0.1196(5) -0.1156(3) 0.0210(17) Uani 1 1 d . . . H7 H -0.0997 -0.1368 -0.0792 0.025 Uiso 1 1 calc R . . C8 C -0.1253(14) -0.1785(5) -0.1649(3) 0.0170(15) Uani 1 1 d . . . C9 C -0.3151(17) -0.2567(5) -0.1542(3) 0.0165(14) Uani 1 1 d . . . C10 C -0.4261(16) -0.3171(5) -0.1966(3) 0.0195(14) Uani 1 1 d . . . C11 C -0.3436(17) -0.2950(4) -0.2525(3) 0.0164(15) Uani 1 1 d . . . C12 C -0.1578(17) -0.2175(5) -0.2674(3) 0.0193(15) Uani 1 1 d . . . C13 C -0.0523(17) -0.1622(4) -0.2226(3) 0.0185(15) 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 0.0189(2) 0.0200(2) 0.0140(2) -0.00007(19) 0.0014(2) 0.00013(19) I2 0.0190(2) 0.0187(2) 0.0232(3) 0.0030(2) -0.0003(2) -0.00206(19) F1 0.034(3) 0.031(2) 0.010(2) 0.0020(17) 0.0032(19) -0.0048(19) F2 0.030(2) 0.022(2) 0.014(2) -0.0045(17) -0.003(2) -0.0068(19) F3 0.028(2) 0.026(2) 0.017(2) -0.0003(17) -0.0012(19) -0.0096(19) C1 0.027(4) 0.024(4) 0.014(4) -0.001(3) -0.001(3) 0.002(3) C2 0.045(5) 0.038(5) 0.019(4) 0.001(3) 0.000(4) -0.022(4) C3 0.037(5) 0.043(5) 0.010(4) -0.007(3) 0.007(3) -0.017(4) N1 0.028(3) 0.034(4) 0.016(3) -0.008(3) -0.004(3) -0.001(3) C4 0.033(4) 0.024(4) 0.014(4) -0.004(3) 0.005(3) -0.005(3) C5 0.037(4) 0.021(4) 0.024(4) 0.002(3) -0.002(4) -0.007(4) C6 0.026(3) 0.031(4) 0.008(3) -0.001(3) -0.002(3) 0.004(4) C7 0.027(4) 0.025(4) 0.012(4) 0.000(3) 0.001(3) 0.005(3) C8 0.015(3) 0.019(3) 0.017(3) 0.006(3) 0.003(3) 0.006(3) C9 0.021(3) 0.022(4) 0.006(3) 0.002(3) 0.003(3) 0.005(3) C10 0.015(3) 0.016(3) 0.028(4) 0.003(3) 0.003(3) 0.005(3) C11 0.022(3) 0.009(3) 0.019(4) 0.001(3) -0.005(3) -0.002(3) C12 0.017(3) 0.023(4) 0.017(4) 0.001(3) 0.003(3) 0.003(3) C13 0.015(3) 0.021(4) 0.020(4) -0.001(3) 0.003(3) -0.004(3) _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 C12 2.096(7) . ? I2 C10 2.080(7) . ? F1 C9 1.351(7) . ? F2 C11 1.355(7) . ? F3 C13 1.353(7) . ? C1 C5 1.387(10) . ? C1 C2 1.391(10) . ? C1 C6 1.488(9) . ? C2 C3 1.370(10) . ? C2 H2 0.9500 . ? C3 N1 1.342(9) . ? C3 H3 0.9500 . ? N1 C4 1.328(9) . ? C4 C5 1.383(9) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.319(9) . ? C6 H6 0.9500 . ? C7 C8 1.490(9) . ? C7 H7 0.9500 . ? C8 C9 1.387(9) . ? C8 C13 1.400(9) . ? C9 C10 1.387(9) . ? C10 C11 1.384(9) . ? C11 C12 1.391(9) . ? C12 C13 1.379(9) . ? 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 C5 C1 C2 115.6(7) . . ? C5 C1 C6 120.3(6) . . ? C2 C1 C6 124.0(7) . . ? C3 C2 C1 119.9(7) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? N1 C3 C2 124.8(7) . . ? N1 C3 H3 117.6 . . ? C2 C3 H3 117.6 . . ? C4 N1 C3 115.0(6) . . ? N1 C4 C5 124.3(7) . . ? N1 C4 H4 117.9 . . ? C5 C4 H4 117.9 . . ? C1 C5 C4 120.3(7) . . ? C1 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C7 C6 C1 124.2(7) . . ? C7 C6 H6 117.9 . . ? C1 C6 H6 117.9 . . ? C6 C7 C8 128.9(7) . . ? C6 C7 H7 115.5 . . ? C8 C7 H7 115.5 . . ? C9 C8 C13 115.5(6) . . ? C9 C8 C7 119.0(6) . . ? C13 C8 C7 125.5(6) . . ? F1 C9 C10 117.7(6) . . ? F1 C9 C8 118.4(6) . . ? C10 C9 C8 123.8(6) . . ? C11 C10 C9 116.6(6) . . ? C11 C10 I2 121.1(5) . . ? C9 C10 I2 122.1(5) . . ? F2 C11 C10 117.5(6) . . ? F2 C11 C12 118.7(6) . . ? C10 C11 C12 123.8(6) . . ? C13 C12 C11 115.9(6) . . ? C13 C12 I1 122.5(5) . . ? C11 C12 I1 121.6(5) . . ? F3 C13 C12 117.9(6) . . ? F3 C13 C8 117.7(6) . . ? C12 C13 C8 124.4(6) . . ? 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 C5 C1 C2 C3 2.5(12) . . . . ? C6 C1 C2 C3 -177.2(8) . . . . ? C1 C2 C3 N1 -1.7(13) . . . . ? C2 C3 N1 C4 -0.4(12) . . . . ? C3 N1 C4 C5 1.7(11) . . . . ? C2 C1 C5 C4 -1.3(11) . . . . ? C6 C1 C5 C4 178.4(7) . . . . ? N1 C4 C5 C1 -0.8(12) . . . . ? C5 C1 C6 C7 -173.2(7) . . . . ? C2 C1 C6 C7 6.4(12) . . . . ? C1 C6 C7 C8 179.3(7) . . . . ? C6 C7 C8 C9 175.2(7) . . . . ? C6 C7 C8 C13 -4.8(12) . . . . ? C13 C8 C9 F1 178.7(6) . . . . ? C7 C8 C9 F1 -1.3(9) . . . . ? C13 C8 C9 C10 0.9(10) . . . . ? C7 C8 C9 C10 -179.1(6) . . . . ? F1 C9 C10 C11 -179.2(6) . . . . ? C8 C9 C10 C11 -1.3(10) . . . . ? F1 C9 C10 I2 -3.7(9) . . . . ? C8 C9 C10 I2 174.1(5) . . . . ? C9 C10 C11 F2 179.2(6) . . . . ? I2 C10 C11 F2 3.7(9) . . . . ? C9 C10 C11 C12 0.5(10) . . . . ? I2 C10 C11 C12 -175.0(5) . . . . ? F2 C11 C12 C13 -178.0(6) . . . . ? C10 C11 C12 C13 0.7(10) . . . . ? F2 C11 C12 I1 3.2(9) . . . . ? C10 C11 C12 I1 -178.0(5) . . . . ? C11 C12 C13 F3 177.8(5) . . . . ? I1 C12 C13 F3 -3.5(9) . . . . ? C11 C12 C13 C8 -1.2(11) . . . . ? I1 C12 C13 C8 177.5(5) . . . . ? C9 C8 C13 F3 -178.6(5) . . . . ? C7 C8 C13 F3 1.4(10) . . . . ? C9 C8 C13 C12 0.5(10) . . . . ? C7 C8 C13 C12 -179.5(7) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.877 _refine_diff_density_min -0.887 _refine_diff_density_rms 0.165