# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1337 data_global _publ_section_title ; Steering non-centrosymmetry into the third dimension. Crystal engineering of an octupolar nonlinear optical crystal ; _publ_contact_author ; Prof. Gautam R. Desiraju School of Chemistry University of Hyderabad Hyderabad 500 046 India ; _publ_contact_author_email 'grdch@uohyd.ernet.in' _publ_contact_author_phone '0091 40 3010567' _publ_contact_author_fax '0091 40 3010567' data_1g _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,4,6-tris-(4-methylphenoxy)-1,3,5-triazine ; _chemical_name_common ? _chemical_formula_moiety 'C24 H21 N3 O3' _chemical_formula_sum 'C24 H21 N3 O3' _chemical_formula_weight 399.44 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 rhombohedral _symmetry_space_group_name_H-M R3c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, z+1/2' '-x+y, y, z+1/2' 'x, x-y, 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' '-y+2/3, -x+1/3, z+5/6' '-x+y+2/3, y+1/3, z+5/6' 'x+2/3, x-y+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' '-y+1/3, -x+2/3, z+7/6' '-x+y+1/3, y+2/3, z+7/6' 'x+1/3, x-y+2/3, z+7/6' _cell_length_a 23.576(3) _cell_length_b 23.576(3) _cell_length_c 6.5913(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3172.9(7) _cell_formula_units_Z 6 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2710 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 28.24 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1260 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type 'empirical on equivalent reflections' _exptl_absorpt_correction_T_min 0.349 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'Siemens SMART CCD area detector system' _diffrn_measurement_method ; Fullsphere data collection in omega at 0.3 deg scan width, 120 frames, phi=0 deg in phi at 0.3 deg scan width four runs with 600 frames, omega = 135,143,156,169 (deg) ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8988 _diffrn_reflns_av_R_equivalents 0.1420 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 28.24 _reflns_number_total 750 _reflns_number_gt 691 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART CCD area detector system' _computing_cell_refinement 'Siemens SAINT program Vers.4.050' _computing_data_reduction 'Siemens SAINT program Vers.4.050' _computing_structure_solution 'Siemens SHELXTL Vers.5.03, SGI-Version' _computing_structure_refinement 'Siemens SHELXL-97 UNIX VERSION Release 97-1' _computing_molecular_graphics 'Siemens SHELXL-97 UNIX VERSION Release 97-1' _computing_publication_material 'Siemens SHELXL-97 UNIX VERSION Release 97-1' _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 w=1/[\s^2^(Fo^2^)+(0.0943P)^2^+0.0000P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(2) _refine_ls_number_reflns 750 _refine_ls_number_parameters 91 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0615 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1321 _refine_ls_wR_factor_gt 0.1274 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.136 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.79275(9) 0.37727(10) 0.0119(3) 0.0502(6) Uani 1 d . . . N1 N 0.68822(10) 0.28896(11) 0.0169(3) 0.0395(6) Uani 1 d . . . C1 C 0.72808(12) 0.35269(12) 0.0173(3) 0.0368(6) Uani 1 d . . . C2 C 0.81889(13) 0.33498(14) 0.0074(4) 0.0458(7) Uani 1 d . . . C3 C 0.81423(15) 0.29754(16) 0.1727(5) 0.0519(8) Uani 1 d . . . H3 H 0.7900 0.2968 0.2906 0.062 Uiso 1 d R . . C4 C 0.84473(17) 0.26067(16) 0.1653(5) 0.0568(7) Uani 1 d . . . H4 H 0.8415 0.2343 0.2805 0.068 Uiso 1 d R . . C5 C 0.88000(17) 0.26027(18) -0.0053(5) 0.0601(8) Uani 1 d . . . C6 C 0.88401(17) 0.29988(19) -0.1680(4) 0.0634(9) Uani 1 d . . . H6 H 0.9089 0.3017 -0.2856 0.076 Uiso 1 d R . . C7 C 0.85348(17) 0.33653(17) -0.1637(4) 0.0559(8) Uani 1 d . . . H7 H 0.8558 0.3627 -0.2786 0.067 Uiso 1 d R . . C8 C 0.9116(2) 0.2187(3) -0.0136(8) 0.0901(13) Uani 1 d . . . H8A H 0.8808 0.1750 0.0297 0.135 Uiso 1 d R . . H8B H 0.9491 0.2369 0.0743 0.135 Uiso 1 d R . . H8C H 0.9252 0.2176 -0.1502 0.135 Uiso 1 d R . . 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 O1 0.0339(12) 0.0397(13) 0.0776(11) -0.0021(8) 0.0044(8) 0.0188(10) N1 0.0390(14) 0.0358(14) 0.0451(9) -0.0029(7) -0.0023(7) 0.0198(11) C1 0.0344(13) 0.0372(16) 0.0396(10) -0.0021(7) 0.0001(7) 0.0185(12) C2 0.0300(15) 0.0424(17) 0.0647(13) -0.0076(10) -0.0008(9) 0.0179(13) C3 0.0365(17) 0.049(2) 0.0689(14) 0.0005(11) 0.0067(10) 0.0204(14) C4 0.0417(18) 0.055(2) 0.0760(16) 0.0034(12) 0.0014(11) 0.0256(16) C5 0.0459(19) 0.059(2) 0.0833(18) -0.0095(15) -0.0019(13) 0.0317(18) C6 0.055(2) 0.078(3) 0.0698(17) -0.0053(15) 0.0077(13) 0.0423(18) C7 0.051(2) 0.061(2) 0.0616(12) -0.0029(12) 0.0032(12) 0.0327(17) C8 0.087(3) 0.109(4) 0.110(3) 0.000(2) 0.006(2) 0.076(3) _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 O1 C1 1.333(3) . ? O1 C2 1.411(4) . ? N1 C1 1.315(3) . ? N1 C1 1.344(4) 3_665 ? C1 N1 1.345(4) 2_655 ? C2 C3 1.371(4) . ? C2 C7 1.382(4) . ? C3 C4 1.378(5) . ? C4 C5 1.401(5) . ? C5 C6 1.394(5) . ? C5 C8 1.500(6) . ? C6 C7 1.374(5) . ? 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 C1 O1 C2 120.1(2) . . ? C1 N1 C1 113.2(3) . 3_665 ? N1 C1 O1 120.3(2) . . ? N1 C1 N1 126.8(3) . 2_655 ? O1 C1 N1 112.9(2) . 2_655 ? C3 C2 C7 121.5(3) . . ? C3 C2 O1 121.1(2) . . ? C7 C2 O1 117.3(3) . . ? C2 C3 C4 118.6(3) . . ? C3 C4 C5 122.1(3) . . ? C6 C5 C4 117.0(3) . . ? C6 C5 C8 121.3(3) . . ? C4 C5 C8 121.6(4) . . ? C7 C6 C5 121.6(3) . . ? C6 C7 C2 119.2(3) . . ? _diffrn_measured_fraction_theta_max 0.266 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.266 _refine_diff_density_max 0.280 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.071