# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2011 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Frederic Paul' _publ_contact_author_email frederic.paul@univ-rennes1.fr _publ_section_title ; Donor-substituted Triaryl-1,3, 5-Triazinanes-2,4,6-Triones: Octupolar NLO-phores with a Remarkable Transparency-Nonlinearity Trade-off ; _publ_requested_category FO loop_ _publ_author_name G.Argouarch R.Veillard T.Roisnel A.Amar A.Boucekkine A.Singh ; I.Ledoux ; F.Paul # Attachment '- 4.cif' #TrackingRef '- 4.cif' # #------------------------------------------------------------------------- #2 Person making the deposition # data_4 _database_code_depnum_ccdc_archive 'CCDC 826557' #TrackingRef '- 4.cif' _audit_creation_date 2011-05-19T18:46:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H15 N3 O3' _chemical_formula_sum 'C27 H15 N3 O3' _chemical_formula_weight 429.42 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R 3 c' _symmetry_space_group_name_Hall 'R 3 -2"c' _symmetry_Int_Tables_number 161 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x+y, y, z+1/2' 'x, x-y, z+1/2' '-y, -x, z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' '-x+y+2/3, y+1/3, z+5/6' 'x+2/3, x-y+1/3, z+5/6' '-y+2/3, -x+1/3, z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x+y+1/3, y+2/3, z+7/6' 'x+1/3, x-y+2/3, z+7/6' '-y+1/3, -x+2/3, z+7/6' _cell_length_a 13.5264(13) _cell_length_b 13.5264 _cell_length_c 24.608(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 3899.2(5) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2593 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 27.43 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.097 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1332 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.766 _exptl_absorpt_correction_T_max 0.989 #----------------------------------------------------------------------------# # SQUEEZE RESULTS # #----------------------------------------------------------------------------# loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 0.130 21.2 12.6 2 0.000 0.000 0.334 148.0 16.6 3 0.000 0.000 0.630 21.2 12.5 4 0.000 0.000 0.834 147.9 16.6 5 0.333 0.667 0.999 150.2 16.5 6 0.333 0.667 0.499 150.2 16.5 7 0.333 0.667 0.293 20.7 12.6 8 0.333 0.667 0.793 20.7 12.7 9 0.667 0.333 0.666 148.8 16.6 10 0.667 0.333 0.166 148.8 16.6 11 0.667 0.333 0.460 21.4 12.8 12 0.667 0.333 0.960 21.4 12.8 _platon_squeeze_details ; ? ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0576 _diffrn_reflns_av_unetI/netI 0.0381 _diffrn_reflns_number 7587 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 1002 _reflns_number_gt 967 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999))' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0875P)^2^+9.4088P] 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_number_reflns 1002 _refine_ls_number_parameters 100 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.072 _refine_ls_R_factor_gt 0.0693 _refine_ls_wR_factor_ref 0.1732 _refine_ls_wR_factor_gt 0.1716 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.161 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_diff_density_max 0.326 _refine_diff_density_min -0.32 _refine_diff_density_rms 0.073 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.6523(4) 0.1102(5) 0.5364(2) 0.0357(12) Uani 1 1 d . . . H1 H 0.7278 0.1237 0.5408 0.043 Uiso 1 1 calc R . . C2 C 0.5566(4) 0.0931(4) 0.53088(18) 0.0249(9) Uani 1 1 d . . . C3 C 0.4414(3) 0.0716(3) 0.5224(2) 0.0249(9) Uani 1 1 d . . . C4 C 0.4067(4) 0.0852(4) 0.47252(19) 0.0252(9) Uani 1 1 d . . . H4 H 0.4596 0.1092 0.4433 0.03 Uiso 1 1 calc R . . C5 C 0.2953(3) 0.0654(3) 0.46217(18) 0.0222(9) Uani 1 1 d . . . H5 H 0.2716 0.0741 0.427 0.027 Uiso 1 1 calc R . . C6 C 0.3648(3) 0.0358(4) 0.56593(19) 0.0238(9) Uani 1 1 d . . . H6 H 0.3883 0.0249 0.6007 0.029 Uiso 1 1 calc R . . C7 C 0.2538(4) 0.0158(3) 0.5587(2) 0.0241(9) Uani 1 1 d . . . H7 H 0.2014 -0.0084 0.5881 0.029 Uiso 1 1 calc R . . C8 C 0.2223(3) 0.0322(3) 0.50724(17) 0.0166(8) Uani 1 1 d . . . N9 N 0.1079(3) 0.0149(3) 0.49912(15) 0.0189(8) Uani 1 1 d . . . C10 C 0.0966(3) 0.1123(3) 0.50117(17) 0.0168(8) Uani 1 1 d . . . O10 O 0.1777(2) 0.2072(2) 0.50532(13) 0.0222(7) 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 C1 0.017(2) 0.046(3) 0.048(3) 0.013(2) 0.002(2) 0.018(2) C2 0.0175(19) 0.030(2) 0.028(2) 0.0083(17) 0.0038(16) 0.0124(17) C3 0.0162(19) 0.0172(18) 0.044(3) 0.0031(17) 0.0004(17) 0.0105(15) C4 0.020(2) 0.023(2) 0.027(2) 0.0009(17) 0.0086(17) 0.0072(16) C5 0.0202(19) 0.0165(18) 0.028(2) 0.0026(16) 0.0045(16) 0.0076(15) C6 0.0172(19) 0.025(2) 0.028(2) 0.0062(17) 0.0006(16) 0.0096(16) C7 0.0177(19) 0.020(2) 0.036(2) 0.0023(17) 0.0062(17) 0.0105(16) C8 0.0098(16) 0.0084(16) 0.031(2) -0.0034(15) -0.0023(14) 0.0043(13) N9 0.0135(15) 0.0176(17) 0.0267(18) 0.0044(13) 0.0019(12) 0.0085(14) C10 0.0163(18) 0.0121(16) 0.023(2) -0.0010(14) -0.0036(15) 0.0077(15) O10 0.0169(14) 0.0162(13) 0.0311(16) 0.0035(12) 0.0027(12) 0.0064(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 1.203(6) . ? C1 H1 0.95 . ? C2 C3 1.450(6) . ? C3 C4 1.359(7) . ? C3 C6 1.398(6) . ? C4 C5 1.415(6) . ? C4 H4 0.95 . ? C5 C8 1.401(6) . ? C5 H5 0.95 . ? C6 C7 1.398(6) . ? C6 H6 0.95 . ? C7 C8 1.388(6) . ? C7 H7 0.95 . ? C8 N9 1.460(5) . ? N9 C10 1.396(5) 3 ? N9 C10 1.401(5) . ? C10 O10 1.206(5) . ? C10 N9 1.396(5) 2 ? 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 C2 C1 H1 180 . . ? C1 C2 C3 178.2(6) . . ? C4 C3 C6 119.5(4) . . ? C4 C3 C2 120.8(4) . . ? C6 C3 C2 119.7(4) . . ? C3 C4 C5 123.0(4) . . ? C3 C4 H4 118.5 . . ? C5 C4 H4 118.5 . . ? C8 C5 C4 115.5(4) . . ? C8 C5 H5 122.2 . . ? C4 C5 H5 122.2 . . ? C7 C6 C3 120.5(4) . . ? C7 C6 H6 119.8 . . ? C3 C6 H6 119.8 . . ? C8 C7 C6 118.1(4) . . ? C8 C7 H7 120.9 . . ? C6 C7 H7 120.9 . . ? C7 C8 C5 123.3(4) . . ? C7 C8 N9 119.0(4) . . ? C5 C8 N9 117.6(4) . . ? C10 N9 C10 123.8(4) 3 . ? C10 N9 C8 118.0(3) 3 . ? C10 N9 C8 116.8(3) . . ? O10 C10 N9 121.7(3) . 2 ? O10 C10 N9 122.3(4) . . ? N9 C10 N9 115.9(4) 2 . ? 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 C6 C3 C4 C5 0.4(6) . . . . ? C2 C3 C4 C5 -180.0(4) . . . . ? C3 C4 C5 C8 1.0(6) . . . . ? C4 C3 C6 C7 -1.0(6) . . . . ? C2 C3 C6 C7 179.3(4) . . . . ? C3 C6 C7 C8 0.2(6) . . . . ? C6 C7 C8 C5 1.4(6) . . . . ? C6 C7 C8 N9 -178.3(4) . . . . ? C4 C5 C8 C7 -1.9(6) . . . . ? C4 C5 C8 N9 177.7(3) . . . . ? C7 C8 N9 C10 -70.8(5) . . . 3 ? C5 C8 N9 C10 109.6(4) . . . 3 ? C7 C8 N9 C10 96.3(4) . . . . ? C5 C8 N9 C10 -83.4(4) . . . . ? C10 N9 C10 O10 171.7(3) 3 . . . ? C8 N9 C10 O10 5.4(6) . . . . ? C10 N9 C10 N9 -7.2(8) 3 . . 2 ? C8 N9 C10 N9 -173.4(3) . . . 2 ?