Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Mrs Heike Suss' _publ_contact_author_address ; Department of Chemistry & Biochemistry University of Berne Freiestrasse 3 Basel CH-3012 SWITZERLAND ; _publ_contact_author_email SUESSH@GMX.DE _publ_section_title ; 2,4,6-tris(4-cyanophenoxy)-1,3,5-triazine (CNPOT): Trigonal synthons in crystal engineering ; loop_ _publ_author_name 'Heike Suss' 'J. Hulliger' 'Antonia Neels' data_cnpot-pa _database_code_depnum_ccdc_archive 'CCDC 254106' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H24 N6 O6' _chemical_formula_weight 564.55 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P63 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x-y, z' 'y, -x+y, z+1/2' '-x+y, -x, z' 'x-y, x, z+1/2' _cell_length_a 15.393(4) _cell_length_b 15.393(4) _cell_length_c 6.6615(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1367.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 8614 _cell_measurement_theta_min 1.53 _cell_measurement_theta_max 24.85 _exptl_crystal_description needle _exptl_crystal_colour 'colourless transparent' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 588 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9012 _diffrn_reflns_av_R_equivalents 0.1392 _diffrn_reflns_av_sigmaI/netI 0.0680 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 24.83 _reflns_number_total 1533 _reflns_number_gt 1126 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _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^)+(0.1710P)^2^+0.1315P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.006(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(6) _refine_ls_number_reflns 1533 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1142 _refine_ls_R_factor_gt 0.0963 _refine_ls_wR_factor_ref 0.2771 _refine_ls_wR_factor_gt 0.2590 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.000 _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 0.2685(3) 0.5745(3) 0.4970(9) 0.0550(11) Uani 1 1 d . A 1 C2 C 0.1034(4) 0.4348(4) 0.5105(9) 0.0619(12) Uani 1 1 d . A 1 C3 C 0.0508(4) 0.3709(5) 0.6626(10) 0.0742(16) Uani 1 1 d . A 1 H3A H 0.0855 0.3604 0.7693 0.089 Uiso 1 1 calc R A 1 C4 C -0.0518(4) 0.3217(5) 0.6625(10) 0.0813(17) Uani 1 1 d . A 1 H4A H -0.0886 0.2786 0.7705 0.098 Uiso 1 1 calc R A 1 C5 C -0.1018(4) 0.3356(4) 0.5018(10) 0.0668(14) Uani 1 1 d . A 1 C6 C -0.0501(4) 0.3961(4) 0.3448(10) 0.0685(15) Uani 1 1 d . A 1 H6A H -0.0855 0.4025 0.2343 0.082 Uiso 1 1 calc R A 1 C7 C 0.0545(4) 0.4486(4) 0.3450(9) 0.0659(14) Uani 1 1 d . A 1 H7A H 0.0914 0.4922 0.2376 0.079 Uiso 1 1 calc R A 1 C8 C -0.2101(4) 0.2779(4) 0.4901(9) 0.0631(13) Uani 1 1 d . A 1 N1 N 0.2327(3) 0.6327(3) 0.4955(9) 0.0634(11) Uani 1 1 d . . 1 N2 N -0.2950(4) 0.2307(4) 0.4960(10) 0.0803(15) Uani 1 1 d . A 1 O1 O 0.2076(2) 0.4735(3) 0.4998(7) 0.0672(10) Uani 1 1 d . A 1 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 0.057(2) 0.071(3) 0.035(2) -0.001(3) 0.003(3) 0.030(2) C2 0.068(3) 0.068(3) 0.046(3) 0.012(3) -0.001(3) 0.030(2) C3 0.058(3) 0.105(4) 0.051(3) 0.011(3) -0.009(3) 0.033(3) C4 0.083(4) 0.108(5) 0.042(3) 0.007(3) 0.000(3) 0.040(4) C5 0.080(3) 0.068(3) 0.053(3) 0.017(3) 0.009(3) 0.037(2) C6 0.066(3) 0.073(3) 0.066(4) 0.001(3) -0.014(3) 0.034(3) C7 0.082(4) 0.075(3) 0.046(3) 0.016(3) 0.012(3) 0.044(3) C8 0.072(3) 0.067(3) 0.038(2) 0.006(3) -0.003(3) 0.026(3) N1 0.073(2) 0.087(3) 0.0362(19) 0.008(3) 0.008(2) 0.044(2) N2 0.079(3) 0.074(3) 0.070(3) 0.012(3) -0.021(3) 0.024(3) O1 0.067(2) 0.074(2) 0.059(2) -0.007(2) -0.017(2) 0.0343(17) _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 N1 1.264(6) . ? C1 O1 1.356(6) . ? C1 N1 1.368(6) 3_665 ? C2 C3 1.361(8) . ? C2 O1 1.405(6) . ? C2 C7 1.411(8) . ? C3 C4 1.369(8) . ? C3 H3A 0.9500 . ? C4 C5 1.396(9) . ? C4 H4A 0.9500 . ? C5 C6 1.362(9) . ? C5 C8 1.447(8) . ? C6 C7 1.394(8) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C8 N2 1.135(6) . ? N1 C1 1.368(6) 5_565 ? 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 N1 C1 O1 121.0(4) . . ? N1 C1 N1 127.7(5) . 3_665 ? O1 C1 N1 111.2(4) . 3_665 ? C3 C2 O1 119.0(5) . . ? C3 C2 C7 121.4(5) . . ? O1 C2 C7 118.6(5) . . ? C2 C3 C4 120.3(5) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C3 C4 C5 119.2(6) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? C6 C5 C4 121.0(5) . . ? C6 C5 C8 118.6(5) . . ? C4 C5 C8 120.1(5) . . ? C5 C6 C7 120.4(5) . . ? C5 C6 H6A 119.8 . . ? C7 C6 H6A 119.8 . . ? C6 C7 C2 117.5(5) . . ? C6 C7 H7A 121.2 . . ? C2 C7 H7A 121.2 . . ? N2 C8 C5 174.7(7) . . ? C1 N1 C1 112.3(5) . 5_565 ? C1 O1 C2 118.4(4) . . ? 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 O1 C2 C3 C4 -171.4(6) . . . . ? C7 C2 C3 C4 -3.0(10) . . . . ? C2 C3 C4 C5 1.9(10) . . . . ? C3 C4 C5 C6 0.9(10) . . . . ? C3 C4 C5 C8 174.7(6) . . . . ? C4 C5 C6 C7 -2.5(9) . . . . ? C8 C5 C6 C7 -176.4(5) . . . . ? C5 C6 C7 C2 1.4(8) . . . . ? C3 C2 C7 C6 1.4(8) . . . . ? O1 C2 C7 C6 169.8(5) . . . . ? C6 C5 C8 N2 -171(6) . . . . ? C4 C5 C8 N2 15(7) . . . . ? O1 C1 N1 C1 178.7(3) . . . 5_565 ? N1 C1 N1 C1 -1.5(12) 3_665 . . 5_565 ? N1 C1 O1 C2 -2.9(8) . . . . ? N1 C1 O1 C2 177.3(5) 3_665 . . . ? C3 C2 O1 C1 -123.9(6) . . . . ? C7 C2 O1 C1 67.5(7) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.83 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.443 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.079