# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dmitrii Perepichka' _publ_contact_author_email DMITRII.PEREPICHKA@MCGILL.CA _publ_section_title ; Supramolecular assembly of heterocirculenes in 2D and 3D ; loop_ _publ_author_name 'Dmitrii Perepichka' E. Balenkova E. Chernichenko O. Ivasenko J. M. ; MacLeod ; 'Valentine Nenajdenko' F. Rosei 'Roman V. Shpanchenko' # Attachment 'sse_CAD_final.cif' #======================================================================= data_(I) _database_code_depnum_ccdc_archive 'CCDC 707828' #======================================================================= # 5. CHEMICAL DATA _chemical_name_systematic ; 1,12:3,4:6,7:9,10-tetraepiselenocycloocta[1,2-c:3,4-c':5,6-c":7,8-c"']\ tetrathiophene ; _chemical_name_common ; 1,12:3,4:6,7:9,10-tetraepiselenocycloocta(1,2-c:3,4-c':5,6- c'':7,8-c''')\ tetrathiophene ; _chemical_formula_moiety 'C16 S4.683 Se3.317' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_sum 'C16 S4.683 Se3.317' _chemical_formula_weight 604.2 _chemical_melting_point ? _chemical_compound_source ? _chemical_absolute_configuration . #======================================================================= # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yabc' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 4.0290(8) _cell_length_b 16.680(3) _cell_length_c 11.270(2) _cell_angle_alpha 90 _cell_angle_beta 94.30(3) _cell_angle_gamma 90 _cell_volume 755.3(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 24 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_measurement_temperature 293 _cell_special_details ; ? ; _exptl_crystal_density_diffrn 2.6561 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_F_000 567 _exptl_absorpt_coefficient_mu 8.711 _exptl_crystal_description needle _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_size_rad ? _exptl_crystal_colour colorless _exptl_absorpt_correction_type None _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 1.000 #======================================================================= # 7. EXPERIMENTAL DATA _exptl_special_details ? _diffrn_ambient_temperature 293 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator ? _diffrn_measurement_device_type CAD-4 _diffrn_detector_area_resol_mean ? _diffrn_measurement_method ? _diffrn_reflns_number 2731 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 24.96 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? #======================================================================= # 8. REFINEMENT DATA _refine_special_details ; ? ; _reflns_number_total 1325 _reflns_number_gt 1032 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_gt 0.0779 _refine_ls_R_factor_all 0.0643 _refine_ls_wR_factor_ref 0.0779 _refine_ls_goodness_of_fit_ref 1.35 _refine_ls_goodness_of_fit_gt 1.35 _refine_ls_restrained_S_gt ? _refine_ls_restrained_S_all ? _refine_ls_number_reflns 902 _refine_ls_number_parameters 113 _refine_ls_number_restraints 4 _refine_ls_number_constraints ? _refine_ls_weighting_scheme sigma _refine_ls_weighting_details w=1/(\s^2^(F)+0.003025F^2^) _refine_ls_hydrogen_treatment ? _refine_ls_shift/su_max 0.0037 _refine_ls_shift/su_mean 0.0003 _refine_diff_density_max 1.90 _refine_diff_density_min -0.43 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 2.31 20.843901 1.02 10.2075 1.5886 0.5687 0.865 51.651199 0.2156 S 0.125 0.123 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 6.9053 1.4679 5.2034 22.215099 1.4379 0.2536 1.5863 56.172001 0.8669 Se -0.093 2.226 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 17.000601 2.4098 5.8196 0.2726 3.9731 15.2372 4.3543 43.816299 2.8409 _computing_data_collection 'CAD4 Users Manual (Enraf-Nonius, 1988)' _computing_cell_refinement 'CAD4 Users Manual (Enraf-Nonius, 1988)' _computing_data_reduction 'CAD4 Users Manual (Enraf-Nonius, 1988)' _computing_structure_solution ? _computing_structure_refinement 'Jana2000 (Petricek, Dusek & Palatinus, 2000)' _computing_molecular_graphics ? _computing_publication_material 'Jana2000 (Petricek, Dusek & Palatinus, 2000)' #======================================================================= # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_adp_type _atom_site_U_iso_or_equiv _atom_site_symmetry_multiplicity _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.163679 0.624912 0.310765 Uani 0.0292(5) 4 0.347(15) d . . . Se1 Se 0.1637(3) 0.62491(7) 0.31076(12) Uani 0.0292(5) 4 0.653(15) d . . . Se2 Se 0.8452(4) 0.30090(8) 0.22424(12) Uani 0.0276(5) 4 0.525(14) d . . . S2 S 0.845195 0.300902 0.224236 Uani 0.0276(5) 4 0.475(14) d . . . Se3 Se 0.5034(5) 0.44684(11) 0.37524(16) Uani 0.0312(7) 4 0.244(11) d . . . S3 S 0.503407 0.446842 0.375236 Uani 0.0312(7) 4 0.756(11) d . . . Se4 Se 0.0304(5) 0.72703(12) 0.05540(17) Uani 0.0306(7) 4 0.235(12) d . . . S4 S 0.030435 0.727033 0.055397 Uani 0.0306(7) 4 0.765(12) d . . . C2 C 0.580(3) 0.4412(5) 0.1391(9) Uani 0.026(3) 4 1 d . . . C3 C 0.421(3) 0.5170(6) 0.1620(9) Uani 0.029(3) 4 1 d . . . C4 C 0.692(2) 0.4005(5) 0.0396(8) Uani 0.025(3) 4 1 d . . . C5 C 0.169(3) 0.6432(6) 0.1476(9) Uani 0.030(3) 4 1 d . . . C6 C 0.370(3) 0.5281(6) 0.2783(9) Uani 0.031(3) 4 1 d . . . C9 C 0.311(3) 0.5827(5) 0.0842(9) Uani 0.027(3) 4 1 d . . . C1 C 0.643(3) 0.3998(6) 0.2449(9) Uani 0.030(3) 4 1 d . . . C10 C 0.824(3) 0.3267(6) 0.0666(8) Uani 0.025(3) 4 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_type_symbol _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 S 0.0397(9) 0.0243(8) 0.0238(8) 0.0027(5) 0.0042(5) -0.0029(5) Se1 Se 0.0397(9) 0.0243(8) 0.0238(8) 0.0027(5) 0.0042(5) -0.0029(5) Se2 Se 0.0385(10) 0.0232(8) 0.0210(8) 0.0018(6) 0.0007(6) 0.0018(6) S2 S 0.0385(10) 0.0232(8) 0.0210(8) 0.0018(6) 0.0007(6) 0.0018(6) Se3 Se 0.0463(13) 0.0239(11) 0.0232(11) 0.0037(8) 0.0011(9) -0.0011(8) S3 S 0.0463(13) 0.0239(11) 0.0232(11) 0.0037(8) 0.0011(9) -0.0011(8) Se4 Se 0.0408(12) 0.0269(11) 0.0243(12) 0.0049(9) 0.0037(8) -0.0048(8) S4 S 0.0408(12) 0.0269(11) 0.0243(12) 0.0049(9) 0.0037(8) -0.0048(8) C2 C 0.038(6) 0.016(4) 0.023(5) -0.002(4) 0.005(4) 0.004(4) C3 C 0.032(5) 0.027(5) 0.026(6) -0.003(4) -0.005(4) -0.003(4) C4 C 0.035(6) 0.018(4) 0.024(5) -0.002(4) 0.003(4) 0.001(4) C5 C 0.036(6) 0.024(5) 0.029(6) -0.001(4) 0.005(5) -0.005(4) C6 C 0.042(6) 0.030(6) 0.022(6) -0.007(5) 0.005(5) -0.003(4) C9 C 0.036(6) 0.018(5) 0.027(5) -0.002(4) -0.001(4) -0.007(4) C1 C 0.038(6) 0.025(5) 0.027(5) 0.000(4) 0.008(5) -0.004(5) C10 C 0.037(6) 0.024(5) 0.014(5) 0.003(4) 0.004(4) 0.000(4) #======================================================================= # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 C5 . . 1.866(11) yes S1 C6 . . 1.865(10) yes Se1 C5 . . 1.866(11) yes Se1 C6 . . 1.865(10) yes Se2 C1 . . 1.862(10) yes Se2 C10 . . 1.824(9) yes S2 C1 . . 1.862(10) yes S2 C10 . . 1.824(9) yes Se3 C6 . . 1.797(10) yes Se3 C1 . . 1.793(11) yes S3 C6 . . 1.797(10) yes S3 C1 . . 1.793(11) yes Se4 C5 . . 1.805(10) yes Se4 C10 . . 1.777(10) yes S4 C5 . . 1.805(10) yes S4 C10 . . 1.777(9) yes C2 C3 . . 1.450(13) yes C2 C4 . . 1.413(14) yes C2 C1 . . 1.383(14) yes C3 C6 . . 1.356(14) yes C3 C9 . . 1.452(14) yes C4 C9 . . 1.422(14) yes C4 C10 . . 1.366(13) yes C5 C9 . . 1.384(14) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 S1 C6 . . . 84.9(4) yes C1 Se2 C10 . . . 85.6(4) yes C6 Se3 C1 . . . 86.0(5) yes C5 Se4 C10 . . 3_665 87.1(5) yes C3 C2 C4 . . . 137.0(9) yes C3 C2 C1 . . . 109.7(9) yes C4 C2 C1 . . . 113.3(8) yes C2 C3 C6 . . . 113.1(9) yes C2 C3 C9 . . . 132.1(9) yes C6 C3 C9 . . . 114.8(9) yes C2 C4 C9 . . 3_665 134.8(9) yes C2 C4 C10 . . . 113.5(8) yes C9 C4 C10 3_665 . . 111.7(8) yes S1 C5 Se4 . . . 131.9(6) yes S1 C5 C9 . . . 115.2(7) yes Se4 C5 C9 . . . 112.9(8) yes S1 C6 Se3 . . . 130.7(6) yes S1 C6 C3 . . . 114.2(7) yes Se3 C6 C3 . . . 115.1(8) yes C3 C9 C4 . . 3_665 136.1(9) yes C3 C9 C5 . . . 111.0(9) yes C4 C9 C5 3_665 . . 112.9(9) yes Se2 C1 Se3 . . . 131.1(6) yes Se2 C1 C2 . . . 112.8(7) yes Se3 C1 C2 . . . 116.0(8) yes Se2 C10 Se4 . . 3_665 129.8(5) yes Se2 C10 C4 . . . 114.7(7) yes Se4 C10 C4 3_665 . . 115.4(7) yes #=======================================================================