# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author # Name and address of author for correspondence ; Pr R. Goumont Institut Lavoisier de Versailles, UMR 8180 Universit\'e de Versailles 45 Avenue des Etats Unis 78035 Versailles cedex France ; _publ_contact_author_phone '(33) 01 39 25 44 72' _publ_contact_author_fax '(33) 01 39 25 44 52' _publ_contact_author_email goumont@chimie.uvsq.fr _publ_requested_coeditor_name ? _publ_contact_letter ; ; #==================================================================== # 2. processing summary (iucr office use only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ; _journal_techeditor_code ? _journal_techeditor_notes ; ; _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #==================================================================== # 3. title and author list _publ_section_title ; Supramolecular association of 1,2,5-chalcogenadiazoles : an unexpected self-assembled dissymetric [Se...N]2 four-membered ring ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address G.Berionni ; Institut Lavoisier de Versailles, UMR 8180 Universit\'e de Versailles 45 Avenue des Etats Unis 78035 Versailles cedex France ; B.Pegot ; Institut Lavoisier de Versailles, UMR 8180 Universit\'e de Versailles 45 Avenue des Etats Unis 78035 Versailles cedex France ; J.Marrot ; Institut Lavoisier de Versailles, UMR 8180 Universit\'e de Versailles 45 Avenue des Etats Unis 78035 Versailles cedex France ; R.Goumont ; Institut Lavoisier de Versailles, UMR 8180 Universit\'e de Versailles 45 Avenue des Etats Unis 78035 Versailles cedex France ; #==================================================================== # 4. text _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_experimental ; ; _publ_section_references ; Sheldrick, G.M. (1993). SHELXL-93. Program for crystal structure determination. Univ. of G\"ottingen, Federal Republic of Germany. Sheldrick, G.M. (1997). SHELXS-86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; _publ_contact_author_name 'Pr R. Goumont' #==================================================================== data_4 _database_code_depnum_ccdc_archive 'CCDC 702658' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 B2 F8 N6 Se3' _chemical_formula_weight 752.90 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' B B 0.0013 0.0007 '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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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' '-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 15.8892(4) _cell_length_b 12.0225(4) _cell_length_c 13.5325(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.711(2) _cell_angle_gamma 90.00 _cell_volume 2584.89(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8577 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 28.68 _exptl_crystal_description platelet _exptl_crystal_colour green _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.935 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 4.351 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2750 _exptl_absorpt_correction_T_max 0.6233 _exptl_absorpt_process_details 'SADABS (Sheldrick, V2.10)' _exptl_special_details ; 'Blessing, Acta Cryst. (1995) A51, 33-38' ; _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 512x512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49871 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 30.10 _reflns_number_total 3791 _reflns_number_gt 2911 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _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^)+(0.1050P)^2^+5.7251P] 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 3791 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1698 _refine_ls_wR_factor_gt 0.1501 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 N1A N 0.59067(12) 0.57469(17) 1.07823(14) 0.0448(5) Uani 1 1 d . . . Se2A Se 0.630877(14) 0.45163(2) 1.025311(17) 0.04630(6) Uani 1 1 d . . . N3A N 0.68005(12) 0.53730(16) 0.92816(14) 0.0431(5) Uani 1 1 d . . . C4A C 0.68850(14) 0.7355(2) 0.88106(16) 0.0477(6) Uani 1 1 d . . . H4A H 0.7214 0.7242 0.8256 0.057 Uiso 1 1 calc R . . C5A C 0.66367(16) 0.8387(2) 0.9078(2) 0.0566(7) Uani 1 1 d . . . H5A H 0.6801 0.8990 0.8697 0.068 Uiso 1 1 calc R . . C6A C 0.61256(17) 0.8583(2) 0.9933(2) 0.0564(7) Uani 1 1 d . . . H6A H 0.5957 0.9305 1.0080 0.068 Uiso 1 1 calc R . . C7A C 0.58860(16) 0.7736(2) 1.0526(2) 0.0530(6) Uani 1 1 d . . . H7A H 0.5576 0.7872 1.1092 0.064 Uiso 1 1 calc R . . C8A C 0.61178(13) 0.6642(2) 1.02675(16) 0.0424(5) Uani 1 1 d . . . C9A C 0.66267(13) 0.64506(19) 0.94056(15) 0.0405(5) Uani 1 1 d . . . C10A C 0.73134(17) 0.4906(3) 0.8486(2) 0.0600(7) Uani 1 1 d . . . H10A H 0.7108 0.5172 0.7860 0.090 Uiso 1 1 calc R . . H10B H 0.7279 0.4109 0.8501 0.090 Uiso 1 1 calc R . . H10C H 0.7889 0.5131 0.8578 0.090 Uiso 1 1 calc R . . N1B N 0.54628(12) 0.37766(17) 1.17231(14) 0.0457(5) Uani 1 1 d . . . Se2B Se 0.5000 0.48209(3) 1.2500 0.04755(8) Uani 1 2 d S . . C6B C 0.52608(17) 0.0801(2) 1.2073(2) 0.0561(7) Uani 1 1 d . . . H6B H 0.5424 0.0124 1.1803 0.067 Uiso 1 1 calc R . . C7B C 0.55227(15) 0.1751(2) 1.16487(17) 0.0502(6) Uani 1 1 d . . . H7B H 0.5865 0.1734 1.1097 0.060 Uiso 1 1 calc R . . C8B C 0.52641(13) 0.27838(19) 1.20634(14) 0.0400(5) Uani 1 1 d . . . B B 0.6560(2) 0.1796(3) 0.8688(2) 0.0607(8) Uani 1 1 d . . . F1 F 0.73852(17) 0.2004(3) 0.8410(2) 0.1442(12) Uani 1 1 d . . . F2 F 0.6548(3) 0.1237(4) 0.9536(3) 0.2095(19) Uani 1 1 d . . . F3 F 0.6145(2) 0.2731(2) 0.8746(4) 0.1722(16) Uani 1 1 d . . . F4 F 0.6269(4) 0.1163(3) 0.8012(3) 0.235(2) 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 N1A 0.0426(8) 0.0470(9) 0.0450(9) 0.0020(8) 0.0102(7) -0.0009(8) Se2A 0.04915(11) 0.04477(12) 0.04526(11) 0.00342(8) 0.01257(9) 0.00103(9) N3A 0.0411(8) 0.0506(10) 0.0380(8) 0.0027(7) 0.0094(7) -0.0002(7) C4A 0.0471(11) 0.0549(12) 0.0410(10) 0.0072(9) 0.0019(9) -0.0077(10) C5A 0.0569(13) 0.0559(13) 0.0570(13) 0.0134(11) -0.0060(11) -0.0085(11) C6A 0.0590(13) 0.0475(12) 0.0626(14) 0.0006(11) -0.0016(12) 0.0029(11) C7A 0.0519(12) 0.0511(12) 0.0562(12) -0.0054(11) 0.0054(10) 0.0047(10) C8A 0.0374(9) 0.0502(11) 0.0397(9) 0.0027(8) 0.0040(8) 0.0022(9) C9A 0.0397(9) 0.0450(10) 0.0368(9) 0.0008(8) 0.0010(8) -0.0043(8) C10A 0.0588(13) 0.0696(16) 0.0522(12) -0.0046(12) 0.0245(10) 0.0030(12) N1B 0.0434(8) 0.0515(10) 0.0425(8) 0.0024(8) 0.0121(7) 0.0024(8) Se2B 0.04728(15) 0.04608(15) 0.04957(16) 0.000 0.01177(13) 0.000 C6B 0.0631(14) 0.0482(12) 0.0570(13) -0.0060(11) 0.0030(11) 0.0037(11) C7B 0.0549(12) 0.0547(13) 0.0412(10) -0.0037(10) 0.0110(9) 0.0106(10) C8B 0.0395(9) 0.0486(11) 0.0320(8) 0.0011(8) 0.0058(7) 0.0025(8) B 0.0782(18) 0.0490(14) 0.0555(14) -0.0108(12) 0.0203(13) 0.0006(14) F1 0.1057(16) 0.200(3) 0.1277(18) 0.045(2) 0.0478(14) 0.029(2) F2 0.324(5) 0.183(4) 0.1237(19) 0.051(2) 0.107(2) 0.025(4) F3 0.1230(19) 0.0661(14) 0.329(5) -0.022(2) 0.061(3) 0.0120(14) F4 0.339(5) 0.178(3) 0.187(3) -0.097(2) -0.052(4) -0.055(4) _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 N1A C8A 1.328(3) . ? N1A Se2A 1.767(2) . ? N1A Se2B 2.9666(19) . ? Se2A N3A 1.8507(19) . ? Se2A N1B 2.5732(19) . ? Se2A F3 2.970(4) . ? N3A C9A 1.336(3) . ? N3A C10A 1.470(3) . ? C4A C5A 1.352(4) . ? C4A C9A 1.416(3) . ? C4A H4A 0.9300 . ? C5A C6A 1.441(4) . ? C5A H5A 0.9300 . ? C6A C7A 1.355(4) . ? C6A H6A 0.9300 . ? C7A C8A 1.410(4) . ? C7A H7A 0.9300 . ? C8A C9A 1.446(3) . ? C10A H10A 0.9600 . ? C10A H10B 0.9600 . ? C10A H10C 0.9600 . ? N1B C8B 1.319(3) . ? N1B Se2B 1.800(2) . ? Se2B N1B 1.800(2) 2_657 ? C6B C7B 1.347(4) . ? C6B C6B 1.431(6) 2_657 ? C6B H6B 0.9300 . ? C7B C8B 1.425(3) . ? C7B H7B 0.9300 . ? C8B C8B 1.458(4) 2_657 ? B F4 1.273(5) . ? B F3 1.305(4) . ? B F2 1.329(5) . ? B F1 1.391(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 C8A N1A Se2A 111.80(15) . . ? C8A N1A Se2B 147.54(15) . . ? Se2A N1A Se2B 100.66(8) . . ? N1A Se2A N3A 88.85(9) . . ? N1A Se2A N1B 77.35(8) . . ? N3A Se2A N1B 166.09(8) . . ? N1A Se2A F3 148.71(9) . . ? N3A Se2A F3 87.05(10) . . ? N1B Se2A F3 103.82(9) . . ? C9A N3A C10A 125.5(2) . . ? C9A N3A Se2A 111.15(15) . . ? C10A N3A Se2A 123.39(17) . . ? C5A C4A C9A 117.7(2) . . ? C5A C4A H4A 121.2 . . ? C9A C4A H4A 121.2 . . ? C4A C5A C6A 122.3(2) . . ? C4A C5A H5A 118.9 . . ? C6A C5A H5A 118.9 . . ? C7A C6A C5A 121.2(3) . . ? C7A C6A H6A 119.4 . . ? C5A C6A H6A 119.4 . . ? C6A C7A C8A 118.5(2) . . ? C6A C7A H7A 120.7 . . ? C8A C7A H7A 120.7 . . ? N1A C8A C7A 123.8(2) . . ? N1A C8A C9A 116.2(2) . . ? C7A C8A C9A 120.0(2) . . ? N3A C9A C4A 127.7(2) . . ? N3A C9A C8A 112.00(19) . . ? C4A C9A C8A 120.3(2) . . ? N3A C10A H10A 109.5 . . ? N3A C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? N3A C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C8B N1B Se2B 109.02(14) . . ? C8B N1B Se2A 135.41(15) . . ? Se2B N1B Se2A 115.56(10) . . ? N1B Se2B N1B 91.57(13) . 2_657 ? N1B Se2B N1A 66.32(8) . . ? N1B Se2B N1A 157.67(8) 2_657 . ? C7B C6B C6B 121.97(15) . 2_657 ? C7B C6B H6B 119.0 . . ? C6B C6B H6B 119.0 2_657 . ? C6B C7B C8B 118.6(2) . . ? C6B C7B H7B 120.7 . . ? C8B C7B H7B 120.7 . . ? N1B C8B C7B 125.41(19) . . ? N1B C8B C8B 115.19(12) . 2_657 ? C7B C8B C8B 119.40(13) . 2_657 ? F4 B F3 112.2(4) . . ? F4 B F2 108.0(4) . . ? F3 B F2 111.8(4) . . ? F4 B F1 104.4(4) . . ? F3 B F1 109.8(3) . . ? F2 B F1 110.4(4) . . ? B F3 Se2A 128.5(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.287 _refine_diff_density_min -0.774 _refine_diff_density_rms 0.234 #===END