Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Jetti, Ram K. R.' 'Mak, Thomas C. W.' 'Nangia, A.' 'Xue, Feng' _publ_contact_author_name 'Dr A Nangia' _publ_contact_author_address ; Dr A Nangia School of Chemistry University of Hyderabad Hyderabad 500 046 INDIA ; _publ_contact_author_email 'ANSC@UOHYD.ERNET.IN' data_CLPOT.TIB _database_code_CSD 161765 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 2,4,6-tris-(4-chlorophenoxy)-1,3,5-triazine, triiodobenzene clathrate ; _chemical_melting_point 215-216 deg C _chemical_formula_moiety (C21 H12 N3 O3 Cl3).(C6 H3 I3) _chemical_formula_sum 'C27 H15 Cl3 I3 N3 O3' _chemical_formula_weight 916.47 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M 'P6(3)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' _cell_length_a 15.4817(6) _cell_length_b 15.4817(6) _cell_length_c 7.0107(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1455.22(12) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.092 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 3.532 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Bruker, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'Bruker SMART CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8911 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 26.36 _reflns_number_total 1979 _reflns_number_gt 1750 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART 5.0 (Bruker, 1998)' _computing_data_reduction 'SAINT 4.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL-PC (Bruker, 1998)' _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^)+(0.0386P)^2^+0.0828P] 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 0.01(3) _refine_ls_number_reflns 1979 _refine_ls_number_parameters 118 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0635 _refine_ls_wR_factor_gt 0.0616 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.047 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.59914(15) 0.23319(15) 0.5910(4) 0.0362(5) Uani 1 1 d . . . C1 C 0.57402(17) 0.30352(18) 0.5905(5) 0.0326(6) Uani 1 1 d . . . O1 O 0.47519(12) 0.26671(12) 0.5888(4) 0.0416(5) Uani 1 1 d D . . C2 C 0.43556(16) 0.33184(17) 0.5898(5) 0.0358(6) Uani 1 1 d D . . C3 C 0.37746(17) 0.32549(18) 0.4394(7) 0.0420(6) Uani 1 1 d D . . H3 H 0.3683 0.2829 0.3382 0.050 Uiso 1 1 calc R . . C4 C 0.33173(18) 0.3833(2) 0.4379(7) 0.0466(6) Uani 1 1 d D . . H4 H 0.2924 0.3805 0.3353 0.056 Uiso 1 1 calc R . . C5 C 0.34573(18) 0.44446(18) 0.5908(6) 0.0403(7) Uani 1 1 d D . . C6 C 0.4044(2) 0.4509(2) 0.7423(5) 0.0433(7) Uani 1 1 d D . . H6 H 0.4133 0.4932 0.8439 0.052 Uiso 1 1 calc R . . C7 C 0.4505(2) 0.3936(2) 0.7428(5) 0.0433(7) Uani 1 1 d D . . H7 H 0.4906 0.3968 0.8444 0.052 Uiso 1 1 calc R . . Cl1 Cl 0.28856(6) 0.51730(6) 0.59091(16) 0.0564(2) Uani 1 1 d D . . I1 I 0.225858(16) 0.005759(19) 0.44431(6) 0.07161(8) Uani 1 1 d . . . C8 C 0.08889(19) 0.0021(2) 0.4598(6) 0.0418(6) Uani 1 1 d . . . C9 C 0.0022(2) -0.0893(2) 0.4580(7) 0.0462(7) Uani 1 1 d . . . H9 H 0.0037 -0.1486 0.4557 0.069 Uiso 1 1 calc 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 N1 0.0298(9) 0.0309(10) 0.0485(14) 0.0005(11) -0.0019(12) 0.0156(8) C1 0.0289(11) 0.0316(12) 0.0359(14) -0.0011(12) -0.0025(12) 0.0143(9) O1 0.0279(8) 0.0318(8) 0.0664(14) -0.0005(10) -0.0015(10) 0.0159(7) C2 0.0218(10) 0.0274(11) 0.0553(18) 0.0036(13) 0.0033(13) 0.0101(9) C3 0.0384(11) 0.0412(12) 0.0507(15) -0.0058(19) -0.0031(19) 0.0231(10) C4 0.0429(12) 0.0522(14) 0.0516(16) 0.003(2) -0.008(2) 0.0289(11) C5 0.0339(12) 0.0324(12) 0.0573(19) 0.0044(15) 0.0047(14) 0.0187(10) C6 0.0382(14) 0.0321(13) 0.057(2) -0.0087(13) -0.0017(14) 0.0155(11) C7 0.0303(12) 0.0446(15) 0.055(2) -0.0062(14) -0.0085(13) 0.0186(12) Cl1 0.0602(4) 0.0533(4) 0.0725(5) 0.0004(4) 0.0015(4) 0.0411(3) I1 0.05611(11) 0.10275(17) 0.07083(16) 0.0009(2) -0.00004(17) 0.05085(11) C8 0.0405(12) 0.0558(14) 0.0322(16) 0.0011(16) -0.0011(16) 0.0265(11) C9 0.0572(14) 0.0474(13) 0.0373(16) 0.0000(18) -0.0002(18) 0.0286(12) _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 N1 C1 1.317(3) 2_655 ? N1 C1 1.327(3) . ? C1 N1 1.317(3) 3_665 ? C1 O1 1.339(3) . ? O1 C2 1.418(3) . ? C2 C3 1.357(5) . ? C2 C7 1.377(4) . ? C3 C4 1.391(4) . ? C4 C5 1.374(5) . ? C5 C6 1.369(5) . ? C5 Cl1 1.747(3) . ? C6 C7 1.389(4) . ? I1 C8 2.096(3) . ? C8 C9 1.380(4) . ? C8 C9 1.381(4) 2 ? C9 C8 1.381(4) 3 ? 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 N1 C1 112.4(2) 2_655 . ? N1 C1 N1 127.6(2) 3_665 . ? N1 C1 O1 119.3(2) 3_665 . ? N1 C1 O1 113.1(2) . . ? C1 O1 C2 120.38(19) . . ? C3 C2 C7 122.0(3) . . ? C3 C2 O1 116.8(3) . . ? C7 C2 O1 121.0(3) . . ? C2 C3 C4 119.4(3) . . ? C5 C4 C3 118.8(3) . . ? C6 C5 C4 121.7(3) . . ? C6 C5 Cl1 119.0(3) . . ? C4 C5 Cl1 119.3(3) . . ? C5 C6 C7 119.3(3) . . ? C2 C7 C6 118.7(3) . . ? C9 C8 C9 122.8(3) . 2 ? C9 C8 I1 118.6(2) . . ? C9 C8 I1 118.39(19) 2 . ? C8 C9 C8 117.2(3) . 3 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.266 _refine_diff_density_min -1.016 _refine_diff_density_rms 0.091 data_BRPOT.TBB _database_code_CSD 161766 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 2,4,6-tris-(4-bromophenoxy)-1,3,5-triazine, tribromobenzene clathrate ; _chemical_melting_point 234-236 deg C _chemical_formula_moiety (C21 H12 N3 O3 Br3).(C6 H3 Br3) _chemical_formula_sum 'C27 H15 Br6 N3 O3' _chemical_formula_weight 908.88 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M 'P6(3)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' _cell_length_a 15.4420(13) _cell_length_b 15.4420(13) _cell_length_c 6.9909(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1443.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.091 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 8.378 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ; Rigaku RU-200 rotating-anode generator powered at 50kV / 90mA ; _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS IIc' _diffrn_measurement_method 'taking xx oscillation frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4453 _diffrn_reflns_av_R_equivalents 0.1359 _diffrn_reflns_av_sigmaI/netI 0.1014 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.55 _reflns_number_total 1715 _reflns_number_gt 1587 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BioteX 1.0 (MSC, 1995)' _computing_cell_refinement 'BioteX 1.0 (MSC, 1995)' _computing_data_reduction 'BioteX 1.0 (MSC, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL-PC (Siemens, 1990)' _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^)+(0.0993P)^2^+0.0706P] 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 0.022(3) _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 0.36(4) _refine_ls_number_reflns 1715 _refine_ls_number_parameters 120 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0771 _refine_ls_R_factor_gt 0.0706 _refine_ls_wR_factor_ref 0.1732 _refine_ls_wR_factor_gt 0.1681 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.097 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.6306(3) 0.3987(3) 0.1710(12) 0.0492(11) Uani 1 1 d U . . C1 C 0.5726(4) 0.3006(4) 0.1711(14) 0.0468(11) Uani 1 1 d U . . O1 O 0.4737(3) 0.2603(3) 0.1746(10) 0.0530(9) Uani 1 1 d DU . . C2 C 0.4317(4) 0.3233(3) 0.1654(11) 0.0499(12) Uani 1 1 d DU . . C3 C 0.3749(5) 0.3189(6) 0.3210(11) 0.0583(15) Uani 1 1 d DU . . H3 H 0.3679 0.2781 0.4246 0.070 Uiso 1 1 calc R . . C4 C 0.3279(5) 0.3764(5) 0.3218(12) 0.0583(15) Uani 1 1 d DU . . H4 H 0.2890 0.3745 0.4250 0.070 Uiso 1 1 calc R . . C5 C 0.3408(4) 0.4353(4) 0.1668(11) 0.0522(12) Uani 1 1 d DU . . C6 C 0.3988(5) 0.4410(5) 0.0119(13) 0.0569(16) Uani 1 1 d DU . . H6 H 0.4069 0.4827 -0.0907 0.068 Uiso 1 1 calc R . . C7 C 0.4447(5) 0.3837(5) 0.0116(12) 0.0565(15) Uani 1 1 d DU . . H7 H 0.4839 0.3861 -0.0915 0.068 Uiso 1 1 calc R . . Br1 Br 0.28084(4) 0.51713(5) 0.1679(2) 0.0601(2) Uani 1 1 d DU . . Br2 Br 0.21062(9) 0.00091(12) 0.3045(2) 0.1150(4) Uani 1 1 d U . . C8 C 0.0891(7) 0.0002(7) 0.2965(15) 0.074(2) Uani 1 1 d U . . C9 C 0.0015(7) -0.0886(7) 0.2970(15) 0.071(2) Uani 1 1 d U . . H9 H 0.0021 -0.1485 0.2977 0.085 Uiso 1 1 calc 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 N1 0.045(2) 0.044(2) 0.061(3) -0.012(3) -0.002(4) 0.0241(17) C1 0.044(2) 0.049(2) 0.050(3) 0.005(4) 0.002(4) 0.0255(19) O1 0.0418(17) 0.0470(18) 0.070(2) 0.003(3) 0.005(3) 0.0221(14) C2 0.040(2) 0.041(2) 0.068(3) -0.002(4) -0.004(4) 0.0194(19) C3 0.058(3) 0.071(4) 0.055(4) 0.010(3) 0.007(3) 0.040(3) C4 0.058(3) 0.067(4) 0.057(4) 0.001(3) 0.007(3) 0.037(3) C5 0.046(2) 0.048(3) 0.061(3) -0.009(4) -0.003(4) 0.023(2) C6 0.050(3) 0.057(4) 0.061(4) 0.005(3) 0.005(3) 0.025(3) C7 0.055(3) 0.064(4) 0.056(3) 0.004(3) 0.013(3) 0.033(3) Br1 0.0622(3) 0.0611(3) 0.0677(4) -0.0018(5) 0.0006(5) 0.0389(3) Br2 0.0937(6) 0.1656(10) 0.1096(9) -0.0009(9) 0.0008(7) 0.0828(7) C8 0.079(4) 0.088(5) 0.058(4) 0.009(4) 0.010(5) 0.044(4) C9 0.093(4) 0.075(4) 0.053(4) 0.001(4) -0.002(4) 0.047(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 N1 C1 1.318(7) . ? N1 C1 1.340(7) 3_665 ? C1 O1 1.330(6) . ? C1 N1 1.340(7) 2_655 ? O1 C2 1.416(7) . ? C2 C7 1.370(9) . ? C2 C3 1.377(9) . ? C3 C4 1.400(10) . ? C4 C5 1.364(10) . ? C5 C6 1.380(10) . ? C5 Br1 1.903(6) . ? C6 C7 1.383(10) . ? Br2 C8 1.873(9) . ? C8 C9 1.361(13) . ? C8 C9 1.391(13) 2 ? C9 C8 1.391(13) 3 ? 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 N1 C1 112.7(5) . 3_665 ? N1 C1 O1 120.0(5) . . ? N1 C1 N1 127.3(5) . 2_655 ? O1 C1 N1 112.7(4) . 2_655 ? C1 O1 C2 119.4(4) . . ? C7 C2 C3 121.8(6) . . ? C7 C2 O1 122.8(6) . . ? C3 C2 O1 115.4(6) . . ? C2 C3 C4 119.4(7) . . ? C5 C4 C3 118.1(7) . . ? C4 C5 C6 122.6(7) . . ? C4 C5 Br1 118.8(5) . . ? C6 C5 Br1 118.5(6) . . ? C5 C6 C7 119.0(7) . . ? C2 C7 C6 119.1(7) . . ? C9 C8 C9 120.4(10) . 2 ? C9 C8 Br2 119.6(8) . . ? C9 C8 Br2 120.0(7) 2 . ? C8 C9 C8 119.6(10) . 3 ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.55 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.649 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.115 data_BRPOT.TIB _database_code_CSD 161767 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 2,4,6-tris-(4-bromophenoxy)-1,3,5-triazine, triiodobenzene clathrate ; _chemical_melting_point 218 deg C _chemical_formula_moiety (C21 H12 N3 O3 Br3).(C6 H3 I3) _chemical_formula_sum 'C27 H15 Br3 I3 N3 O3' _chemical_formula_weight 1049.85 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' _cell_length_a 15.6268(16) _cell_length_b 15.6268(16) _cell_length_c 7.0464(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1490.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 972 _exptl_absorpt_coefficient_mu 7.203 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10527 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 28.03 _reflns_number_total 2406 _reflns_number_gt 1941 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0338P)^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 SHELXL _refine_ls_extinction_coef 0.0011(2) _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 0.042(14) _refine_ls_number_reflns 2406 _refine_ls_number_parameters 119 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0649 _refine_ls_wR_factor_gt 0.0607 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _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 N1 N 0.3661(2) 0.60047(19) 0.1379(6) 0.0323(6) Uani 1 1 d . . . C1 C 0.2715(2) 0.5747(2) 0.1374(7) 0.0298(7) Uani 1 1 d . . . O1 O 0.21070(16) 0.47629(16) 0.1365(5) 0.0380(6) Uani 1 1 d . . . C2 C 0.1075(2) 0.4372(2) 0.1386(7) 0.0331(8) Uani 1 1 d . . . C3 C 0.0559(3) 0.3782(3) -0.0117(8) 0.0391(9) Uani 1 1 d . . . H3A H 0.0891 0.3697 -0.1129 0.047 Uiso 1 1 calc R . . C4 C -0.0466(3) 0.3312(3) -0.0115(9) 0.0416(9) Uani 1 1 d . . . H4A H -0.0830 0.2901 -0.1112 0.050 Uiso 1 1 calc R . . C5 C -0.0933(2) 0.3466(2) 0.1388(8) 0.0351(8) Uani 1 1 d . . . C6 C -0.0411(3) 0.4063(3) 0.2898(7) 0.0411(10) Uani 1 1 d . . . H6A H -0.0744 0.4153 0.3904 0.049 Uiso 1 1 calc R . . C7 C 0.0613(3) 0.4528(3) 0.2903(7) 0.0394(10) Uani 1 1 d . . . H7A H 0.0978 0.4934 0.3906 0.047 Uiso 1 1 calc R . . Br1 Br -0.23292(3) 0.28498(3) 0.13964(10) 0.04691(12) Uani 1 1 d . . . C8 C -0.0877(3) 0.0000(3) 0.0060(8) 0.0425(9) Uani 1 1 d . . . C9 C -0.0002(3) 0.0895(3) 0.0085(8) 0.0427(9) Uani 1 1 d . . . H9A H -0.0003 0.1489 0.0117 0.051 Uiso 1 1 calc R . . I1 I -0.22139(2) -0.00069(3) -0.00665(5) 0.07181(14) 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 N1 0.0292(14) 0.0264(13) 0.0425(18) -0.0020(18) -0.0001(17) 0.0149(11) C1 0.0277(15) 0.0233(15) 0.0349(18) -0.0002(19) 0.0000(19) 0.0101(13) O1 0.0279(12) 0.0267(11) 0.0590(18) -0.0040(15) -0.0008(15) 0.0135(10) C2 0.0281(16) 0.0197(14) 0.050(2) 0.005(2) 0.001(2) 0.0106(12) C3 0.0329(18) 0.0343(18) 0.046(2) -0.006(2) 0.000(2) 0.0133(15) C4 0.0344(18) 0.0387(19) 0.042(2) -0.003(2) -0.004(2) 0.0108(16) C5 0.0245(15) 0.0304(17) 0.049(2) 0.006(2) -0.002(2) 0.0122(13) C6 0.042(2) 0.039(2) 0.048(3) -0.0049(19) 0.003(2) 0.0237(19) C7 0.034(2) 0.0275(19) 0.053(3) -0.0085(18) -0.0065(19) 0.0122(16) Br1 0.03005(18) 0.0490(2) 0.0579(3) 0.0012(3) -0.0003(2) 0.01692(16) C8 0.046(2) 0.058(2) 0.031(2) 0.003(2) -0.002(2) 0.032(2) C9 0.052(2) 0.045(2) 0.034(2) -0.002(2) -0.004(2) 0.0268(19) I1 0.0565(2) 0.1044(3) 0.0709(2) -0.0004(3) 0.0003(2) 0.0526(2) _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 N1 C1 1.315(4) 2_665 ? N1 C1 1.324(4) . ? C1 N1 1.315(4) 3_565 ? C1 O1 1.344(4) . ? O1 C2 1.410(4) . ? C2 C3 1.371(7) . ? C2 C7 1.379(6) . ? C3 C4 1.388(5) . ? C4 C5 1.373(7) . ? C5 C6 1.380(7) . ? C5 Br1 1.894(3) . ? C6 C7 1.388(6) . ? C8 C9 1.383(6) . ? C8 C9 1.389(6) 2 ? C8 I1 2.085(4) . ? C9 C8 1.389(6) 3 ? 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 N1 C1 112.8(3) 2_665 . ? N1 C1 N1 127.2(3) 3_565 . ? N1 C1 O1 119.8(3) 3_565 . ? N1 C1 O1 113.0(3) . . ? C1 O1 C2 119.8(2) . . ? C3 C2 C7 122.3(3) . . ? C3 C2 O1 116.4(4) . . ? C7 C2 O1 121.2(4) . . ? C2 C3 C4 119.3(4) . . ? C5 C4 C3 118.8(4) . . ? C4 C5 C6 121.8(3) . . ? C4 C5 Br1 119.4(3) . . ? C6 C5 Br1 118.8(3) . . ? C5 C6 C7 119.5(4) . . ? C2 C7 C6 118.3(4) . . ? C9 C8 C9 122.0(4) . 2 ? C9 C8 I1 119.2(3) . . ? C9 C8 I1 118.8(3) 2 . ? C8 C9 C8 117.9(4) . 3 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.419 _refine_diff_density_min -0.501 _refine_diff_density_rms 0.076