Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data__global _journal_name_full Chem.Commun. _audit_creation_date 'Wed Oct 16 17:58:00 2002' _audit_creation_method 'by teXsan' _audit_update_record ? _journal_coden_Cambridge 0182 loop_ _publ_author_name 'Masakazu Ohkita' 'Miki Kawano' 'Takanori Suzuki' 'Takashi Tsuji' _publ_contact_author_name 'Dr Masakazu Ohkita' _publ_contact_author_address ; Department of Applied Chemistry Nagoya Institute of Technology Faculty of Engineering Nagoya 466-8555 JAPAN ; _publ_contact_author_email OHKITA@ACH.NITECH.AC.JP _publ_section_title ; Supramolecular graphyne: a C(sp)-H....N hydrogen-bonded unique network structure of 2,4,6-triethynyl-1,3,5-triazine. ; _publ_section_references ; Molecular Structure Corporation, Rigaku Corporation. (2000). teXsan. Single Crystal Structure Analysis Software. Version 1.11. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. ; #------------------------------------------------------------------------------ data__020214 _database_code_CSD 193181 #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C9 H3 N3 ' _chemical_formula_moiety 'C9 H3 N3 ' _chemical_formula_weight 153.14 _chemical_melting_point 121 #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y,1/2-z -x,-y,-z x,-y,1/2+z 1/2+x,1/2+y,z 1/2-x,1/2+y,1/2-z 1/2-x,1/2-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 14.44(1) _cell_length_b 8.570(5) _cell_length_c 7.505(5) _cell_angle_alpha 90 _cell_angle_beta 119.31(1) _cell_angle_gamma 90 _cell_volume 809.9(9) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1176 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 153.1 #------------------------------------------------------------------------------ _exptl_crystal_description Platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.010 _exptl_crystal_size_rad 0.25 _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min 0.999 _exptl_absorpt_correction_T_max 0.999 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.62 _diffrn_reflns_number 352 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_theta_max 27.47 _diffrn_measured_fraction_theta_max 0.9666 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.9666 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 3.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 898 _reflns_number_gt 586 _reflns_threshold_expression F^2^>3.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.0497 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 586 _refine_ls_number_parameters 57 _refine_ls_goodness_of_fit_ref 1.246 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00063|Fo|^2^]' _refine_ls_shift/su_max 0.0072 _refine_diff_density_max 0.19 _refine_diff_density_min -0.16 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # 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_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N(1) N 0.0000 0.0060(2) 0.7500 0.0212(4) Uani 1.00 d S . . N(2) N 0.08127(10) 0.2468(1) 0.9082(2) 0.0220(3) Uani 1.00 d . . . C(1) C 0.0774(1) 0.0905(2) 0.8975(2) 0.0205(3) Uani 1.00 d . . . C(2) C 0.1643(1) 0.0062(2) 1.0603(2) 0.0258(4) Uani 1.00 d . . . C(3) C 0.2348(1) -0.0627(2) 1.1932(2) 0.0354(4) Uani 1.00 d . . . C(4) C 0.0000 0.3177(2) 0.7500 0.0210(5) Uani 1.00 d S . . C(5) C 0.0000 0.4862(3) 0.7500 0.0268(5) Uani 1.00 d S . . C(6) C 0.0000 0.6242(3) 0.7500 0.0347(6) Uani 1.00 d S . . H(1) H 0.2924 -0.1199 1.3028 0.0420 Uiso 1.00 calc . . . H(2) H 0.0000 0.7368 0.7500 0.0420 Uiso 1.00 calc S . . loop_ _atom_site_aniso_label _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 N(1) 0.0200(8) 0.0183(8) 0.0206(8) 0.0000 0.0064(6) 0.0000 N(2) 0.0219(6) 0.0198(6) 0.0188(5) -0.0002(5) 0.0057(4) -0.0008(5) C(1) 0.0204(6) 0.0212(7) 0.0179(6) 0.0018(6) 0.0078(5) 0.0008(5) C(2) 0.0249(7) 0.0259(7) 0.0253(7) -0.0001(6) 0.0112(5) 0.0002(6) C(3) 0.0267(7) 0.0429(9) 0.0309(8) 0.0101(8) 0.0096(6) 0.0111(8) C(4) 0.0224(9) 0.0198(10) 0.0196(8) 0.0000 0.0092(7) 0.0000 C(5) 0.0249(10) 0.025(1) 0.0265(10) 0.0000 0.0099(8) 0.0000 C(6) 0.047(1) 0.019(1) 0.040(1) 0.0000 0.0230(9) 0.0000 #------------------------------------------------------------------------------ _computing_data_collection CRYSTALCLEAR _computing_cell_refinement CRYSTALCLEAR _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N(1) C(1) 1.337(2) . . yes N(1) C(1) 1.337(2) . 2_556 yes N(2) C(1) 1.342(2) . . yes N(2) C(4) 1.338(2) . . yes C(1) C(2) 1.446(2) . . yes C(2) C(3) 1.177(2) . . yes C(4) C(5) 1.444(3) . . yes C(5) C(6) 1.183(3) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(1) N(1) C(1) 114.3(2) . . 2_556 yes C(1) N(2) C(4) 114.0(1) . . . yes N(1) C(1) N(2) 125.8(1) . . . yes N(1) C(1) C(2) 117.2(1) . . . yes N(2) C(1) C(2) 117.1(1) . . . yes C(1) C(2) C(3) 179.7(2) . . . yes N(2) C(4) N(2) 126.1(2) . . 2_556 yes N(2) C(4) C(5) 117.0(1) . . . yes N(2) C(4) C(5) 117.0(1) 2_556 . . yes C(4) C(5) C(6) 180.0000(1) . . . yes #------------------------------------------------------------------------------ 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 N(1) C(1) N(2) C(4) -2.1(2) . . . . yes N(1) C(1) C(2) C(3) -75(31) . . . . yes N(1) C(1) N(2) C(4) -2.1(2) . 2_556 2_556 . yes N(2) C(1) N(1) C(1) 1.1(1) . . . 2_556 yes N(2) C(1) C(2) C(3) 104(31) . . . . yes N(2) C(4) N(2) C(1) 1.0(1) . . 2_556 2_556 yes C(1) N(1) C(1) C(2) -179.2(2) . . 2_556 2_556 yes C(1) N(2) C(4) C(5) -179.0(1) . . . . yes C(2) C(1) N(2) C(4) 178.2(1) . . . . yes C(2) C(1) N(2) C(4) 178.2(1) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag N(1) C(6) 3.272(3) . 1_545 ? N(1) C(2) 3.313(2) . 3_557 ? N(1) C(2) 3.313(2) . 4_554 ? N(1) C(1) 3.439(2) . 3_557 ? N(1) C(1) 3.439(2) . 4_554 ? N(2) C(3) 3.300(2) . 6_557 ? N(2) C(6) 3.482(2) . 3_567 ? C(1) C(3) 3.314(3) . 4_554 ? C(1) C(2) 3.432(3) . 4_554 ? C(2) C(3) 3.406(3) . 4_554 ? #------------------------------------------------------------------------------ #------------------------------------------------------------------------------