Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Professor A Nangia' _publ_contact_author_address ; School of Chemistry University of Hyderabad P O Central University Hyderabad 500046 Hyderabad INDIA ; _publ_contact_author_email 'ASHWINI NANGIA@REDIFFMAIL.COM' _publ_section_title ; Self-assembled organic tubular host for van der Waals guest inclusion ; loop_ _publ_author_name A.Nangia B.K.Saha # Attachment '2.acetylacetone.cif' data_acac3-s _database_code_depnum_ccdc_archive 'CCDC 293559' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,4,6-tris(2-chloro-3-pyridyloxy)-1,3,5-triazine, acetylacetone ; _chemical_name_common ;2,4,6-tris(2-chloro-3-pyridyloxy)-1,3,5-triazine, acetylacetone ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H9 Cl3 N6 O3, 0.25(C5 H8 O2)' _chemical_formula_sum 'C19.25 H11 Cl3 N6 O3.5' _chemical_formula_weight 488.70 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2453(6) _cell_length_b 10.1233(10) _cell_length_c 16.8774(17) _cell_angle_alpha 93.037(2) _cell_angle_beta 92.521(2) _cell_angle_gamma 90.826(2) _cell_volume 1064.36(18) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4193 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.463 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8775 _exptl_absorpt_correction_T_max 0.9173 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7939 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 26.40 _reflns_number_total 4314 _reflns_number_gt 3489 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997) and squeeze' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0531P)^2^+0.4970P] 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_extinction_coef ? _refine_ls_number_reflns 4314 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1027 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 Cl1 Cl 0.84573(8) 0.45399(6) 0.11830(3) 0.02324(15) Uani 1 1 d . . . Cl2 Cl -0.12116(9) 0.33116(7) 0.32144(3) 0.02982(17) Uani 1 1 d . . . Cl3 Cl -0.17962(9) 0.75152(6) 0.22992(4) 0.02947(16) Uani 1 1 d . . . O1 O 0.3819(2) 0.48911(14) 0.08577(8) 0.0154(3) Uani 1 1 d . . . O2 O 0.3510(2) 0.32523(14) 0.32917(8) 0.0160(3) Uani 1 1 d . . . O3 O 0.2622(2) 0.76288(14) 0.29969(8) 0.0175(3) Uani 1 1 d . . . N1 N 0.3800(3) 0.40123(17) 0.20809(10) 0.0140(4) Uani 1 1 d . . . N2 N 0.3041(3) 0.54818(17) 0.31801(10) 0.0154(4) Uani 1 1 d . . . N3 N 0.3139(3) 0.62915(17) 0.18808(10) 0.0146(4) Uani 1 1 d . . . N4 N 0.7690(3) 0.24131(19) 0.02622(11) 0.0199(4) Uani 1 1 d . . . N5 N -0.0596(3) 0.3335(2) 0.47575(11) 0.0211(4) Uani 1 1 d . . . N6 N -0.0567(3) 0.9769(2) 0.17634(12) 0.0248(4) Uani 1 1 d . . . C1 C 0.3601(3) 0.5049(2) 0.16421(12) 0.0131(4) Uani 1 1 d . . . C2 C 0.3437(3) 0.4311(2) 0.28421(12) 0.0144(4) Uani 1 1 d . . . C3 C 0.2937(3) 0.6420(2) 0.26535(12) 0.0140(4) Uani 1 1 d . . . C4 C 0.4604(3) 0.3693(2) 0.05484(12) 0.0141(4) Uani 1 1 d . . . C5 C 0.3295(3) 0.2836(2) 0.00864(12) 0.0179(5) Uani 1 1 d . . . H5 H 0.1797 0.2979 0.0030 0.021 Uiso 1 1 calc R . . C6 C 0.4217(4) 0.1757(2) -0.02951(13) 0.0215(5) Uani 1 1 d . . . H6 H 0.3364 0.1142 -0.0621 0.026 Uiso 1 1 calc R . . C7 C 0.6396(4) 0.1591(2) -0.01929(13) 0.0232(5) Uani 1 1 d . . . H7 H 0.7016 0.0851 -0.0461 0.028 Uiso 1 1 calc R . . C8 C 0.6790(3) 0.3437(2) 0.06176(12) 0.0155(4) Uani 1 1 d . . . C9 C 0.2595(3) 0.3370(2) 0.40350(12) 0.0140(4) Uani 1 1 d . . . C10 C 0.3865(3) 0.3410(2) 0.47202(13) 0.0177(4) Uani 1 1 d . . . H10 H 0.5384 0.3440 0.4705 0.021 Uiso 1 1 calc R . . C11 C 0.2861(4) 0.3405(2) 0.54323(13) 0.0202(5) Uani 1 1 d . . . H11 H 0.3684 0.3429 0.5920 0.024 Uiso 1 1 calc R . . C12 C 0.0653(4) 0.3366(2) 0.54299(13) 0.0207(5) Uani 1 1 d . . . H12 H -0.0017 0.3360 0.5924 0.025 Uiso 1 1 calc R . . C13 C 0.0390(3) 0.3343(2) 0.40851(13) 0.0180(5) Uani 1 1 d . . . C14 C 0.2126(3) 0.8666(2) 0.25090(12) 0.0164(4) Uani 1 1 d . . . C15 C 0.3591(4) 0.9656(2) 0.24125(13) 0.0204(5) Uani 1 1 d . . . H15 H 0.5011 0.9615 0.2635 0.025 Uiso 1 1 calc R . . C16 C 0.2950(4) 1.0721(2) 0.19820(14) 0.0229(5) Uani 1 1 d . . . H16 H 0.3923 1.1427 0.1902 0.027 Uiso 1 1 calc R . . C17 C 0.0881(4) 1.0738(2) 0.16733(14) 0.0262(5) Uani 1 1 d . . . H17 H 0.0450 1.1473 0.1381 0.031 Uiso 1 1 calc R . . C18 C 0.0075(3) 0.8769(2) 0.21747(13) 0.0194(5) 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 Cl1 0.0169(3) 0.0260(3) 0.0259(3) -0.0046(2) -0.0023(2) 0.0003(2) Cl2 0.0181(3) 0.0511(4) 0.0202(3) 0.0023(3) -0.0018(2) 0.0026(3) Cl3 0.0190(3) 0.0223(3) 0.0467(4) -0.0023(3) 0.0035(2) -0.0016(2) O1 0.0192(7) 0.0145(8) 0.0129(7) 0.0008(6) 0.0043(6) 0.0053(6) O2 0.0207(8) 0.0137(8) 0.0145(7) 0.0025(6) 0.0065(6) 0.0058(6) O3 0.0252(8) 0.0109(8) 0.0163(8) -0.0006(6) 0.0017(6) 0.0037(6) N1 0.0141(8) 0.0124(9) 0.0160(9) 0.0012(7) 0.0045(7) 0.0012(7) N2 0.0169(9) 0.0141(9) 0.0155(9) 0.0000(7) 0.0044(7) 0.0028(7) N3 0.0143(9) 0.0139(9) 0.0157(9) 0.0004(7) 0.0026(7) 0.0022(7) N4 0.0196(9) 0.0213(11) 0.0194(9) 0.0004(8) 0.0044(7) 0.0068(8) N5 0.0174(9) 0.0248(11) 0.0218(10) 0.0017(8) 0.0075(7) 0.0011(8) N6 0.0257(10) 0.0202(11) 0.0281(11) -0.0022(8) -0.0010(8) 0.0074(8) C1 0.0084(9) 0.0150(11) 0.0160(10) 0.0011(8) 0.0022(7) -0.0008(8) C2 0.0098(9) 0.0151(11) 0.0187(11) 0.0039(8) 0.0028(8) 0.0016(8) C3 0.0105(9) 0.0115(11) 0.0199(11) -0.0013(8) 0.0028(8) 0.0010(8) C4 0.0170(10) 0.0150(11) 0.0109(10) 0.0020(8) 0.0053(8) 0.0029(8) C5 0.0155(10) 0.0234(12) 0.0152(10) 0.0030(9) 0.0028(8) -0.0002(9) C6 0.0281(12) 0.0198(12) 0.0162(11) -0.0006(9) 0.0007(9) -0.0031(9) C7 0.0313(13) 0.0194(12) 0.0190(11) -0.0043(9) 0.0062(9) 0.0048(10) C8 0.0157(10) 0.0159(11) 0.0154(10) 0.0024(8) 0.0017(8) 0.0010(8) C9 0.0181(10) 0.0108(10) 0.0138(10) 0.0025(8) 0.0064(8) 0.0018(8) C10 0.0163(10) 0.0143(11) 0.0226(11) 0.0008(9) 0.0020(8) 0.0017(8) C11 0.0266(12) 0.0170(12) 0.0168(11) 0.0006(9) -0.0006(9) 0.0000(9) C12 0.0281(12) 0.0205(12) 0.0142(11) 0.0010(9) 0.0079(9) 0.0030(9) C13 0.0188(11) 0.0190(12) 0.0161(11) 0.0011(9) -0.0001(8) 0.0018(9) C14 0.0240(11) 0.0095(11) 0.0159(11) -0.0022(8) 0.0037(8) 0.0051(8) C15 0.0221(11) 0.0166(12) 0.0222(12) -0.0034(9) 0.0016(9) 0.0018(9) C16 0.0358(13) 0.0093(11) 0.0236(12) -0.0026(9) 0.0068(10) -0.0003(9) C17 0.0391(14) 0.0167(12) 0.0231(12) 0.0021(9) 0.0031(10) 0.0091(10) C18 0.0199(11) 0.0142(11) 0.0237(12) -0.0052(9) 0.0026(9) 0.0019(8) _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 Cl1 C8 1.734(2) . ? Cl2 C13 1.740(2) . ? Cl3 C18 1.740(2) . ? O1 C1 1.338(2) . ? O1 C4 1.399(2) . ? O3 C3 1.347(2) . ? O3 C14 1.398(2) . ? O2 C2 1.346(2) . ? O2 C9 1.401(2) . ? N2 C2 1.319(3) . ? N2 C3 1.335(3) . ? N1 C1 1.321(3) . ? N1 C2 1.334(3) . ? N5 C13 1.315(3) . ? N5 C12 1.347(3) . ? N3 C3 1.316(3) . ? N3 C1 1.339(3) . ? C9 C10 1.371(3) . ? C9 C13 1.384(3) . ? N6 C18 1.315(3) . ? N6 C17 1.344(3) . ? N4 C8 1.316(3) . ? N4 C7 1.339(3) . ? C8 C4 1.394(3) . ? C4 C5 1.371(3) . ? C7 C6 1.378(3) . ? C7 H7 0.9500 . ? C18 C14 1.384(3) . ? C15 C14 1.369(3) . ? C15 C16 1.386(3) . ? C15 H15 0.9500 . ? C5 C6 1.384(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C16 C17 1.372(3) . ? C16 H16 0.9500 . ? C11 C12 1.379(3) . ? C11 C10 1.380(3) . ? C11 H11 0.9500 . ? C10 H10 0.9500 . ? C12 H12 0.9500 . ? C17 H17 0.9500 . ? 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 C4 118.65(15) . . ? C3 O3 C14 118.51(16) . . ? C2 O2 C9 117.55(16) . . ? C2 N2 C3 111.95(18) . . ? C1 N1 C2 112.06(18) . . ? C13 N5 C12 116.77(19) . . ? C3 N3 C1 111.91(17) . . ? C10 C9 C13 119.19(19) . . ? C10 C9 O2 120.56(18) . . ? C13 C9 O2 120.05(18) . . ? C18 N6 C17 116.8(2) . . ? N1 C1 O1 119.03(18) . . ? N1 C1 N3 127.80(19) . . ? O1 C1 N3 113.15(17) . . ? N2 C2 N1 127.95(19) . . ? N2 C2 O2 119.02(18) . . ? N1 C2 O2 113.02(18) . . ? C8 N4 C7 116.72(19) . . ? N3 C3 N2 128.19(19) . . ? N3 C3 O3 119.36(18) . . ? N2 C3 O3 112.44(18) . . ? N4 C8 C4 123.8(2) . . ? N4 C8 Cl1 117.27(16) . . ? C4 C8 Cl1 118.95(16) . . ? C5 C4 C8 118.88(19) . . ? C5 C4 O1 120.52(18) . . ? C8 C4 O1 120.06(19) . . ? N4 C7 C6 123.8(2) . . ? N4 C7 H7 118.1 . . ? C6 C7 H7 118.1 . . ? N6 C18 C14 123.9(2) . . ? N6 C18 Cl3 117.10(17) . . ? C14 C18 Cl3 118.98(17) . . ? C14 C15 C16 118.3(2) . . ? C14 C15 H15 120.9 . . ? C16 C15 H15 120.9 . . ? C4 C5 C6 118.1(2) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? C7 C6 C5 118.7(2) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C17 C16 C15 118.7(2) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C15 C14 C18 118.8(2) . . ? C15 C14 O3 120.71(19) . . ? C18 C14 O3 120.19(19) . . ? C12 C11 C10 119.4(2) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? N5 C13 C9 124.0(2) . . ? N5 C13 Cl2 117.06(16) . . ? C9 C13 Cl2 118.97(16) . . ? C9 C10 C11 117.7(2) . . ? C9 C10 H10 121.1 . . ? C11 C10 H10 121.1 . . ? N5 C12 C11 122.9(2) . . ? N5 C12 H12 118.5 . . ? C11 C12 H12 118.5 . . ? N6 C17 C16 123.4(2) . . ? N6 C17 H17 118.3 . . ? C16 C17 H17 118.3 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.483 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.072 # Attachment '2.acetone.cif' data_ace-s _database_code_depnum_ccdc_archive 'CCDC 293560' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,4,6-tris(2-chloro-3-pyridyloxy)-1,3,5-triazine, acetone ; _chemical_name_common '2,4,6-tris(2-chloro-3-pyridyloxy)-1,3,5-triazine, acetone' _chemical_melting_point ? _chemical_formula_moiety 'C18 H9 Cl3 N6 O3, 0.53(C3 H6 O)' _chemical_formula_sum 'C19.59 H12.18 Cl3 N6 O3.53' _chemical_formula_weight 494.45 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2482(7) _cell_length_b 10.1684(12) _cell_length_c 16.8235(19) _cell_angle_alpha 86.796(2) _cell_angle_beta 87.072(2) _cell_angle_gamma 89.309(2) _cell_volume 1065.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3613 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 27.36 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.541 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.462 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8513 _exptl_absorpt_correction_T_max 0.9684 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13401 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 26.38 _reflns_number_total 4339 _reflns_number_gt 3578 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997) and squeeze' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0532P)^2^+0.1906P] 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_extinction_coef ? _refine_ls_number_reflns 4339 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _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 Cl1 Cl 1.34773(8) -0.04759(5) 0.38295(3) 0.02499(15) Uani 1 1 d . . . Cl2 Cl 0.38330(8) -0.16797(6) 0.17627(3) 0.02957(16) Uani 1 1 d . . . Cl3 Cl 0.31835(9) 0.25329(6) 0.27536(4) 0.03038(16) Uani 1 1 d . . . O1 O 0.8828(2) -0.01323(13) 0.41476(8) 0.0170(3) Uani 1 1 d . . . O2 O 0.8554(2) -0.17699(13) 0.17124(8) 0.0169(3) Uani 1 1 d . . . O3 O 0.7556(2) 0.25943(13) 0.19987(8) 0.0193(3) Uani 1 1 d . . . N1 N 0.8819(2) -0.10120(16) 0.29233(10) 0.0155(4) Uani 1 1 d . . . N2 N 0.8007(3) 0.04508(16) 0.18232(10) 0.0165(4) Uani 1 1 d . . . N3 N 0.8135(3) 0.12623(16) 0.31217(10) 0.0162(4) Uani 1 1 d . . . N4 N 1.2775(3) -0.26044(17) 0.47432(10) 0.0209(4) Uani 1 1 d . . . N5 N 0.4542(3) -0.16355(18) 0.02177(10) 0.0216(4) Uani 1 1 d . . . N6 N 0.4420(3) 0.47751(18) 0.32578(11) 0.0271(4) Uani 1 1 d . . . C1 C 0.8606(3) 0.0028(2) 0.33617(12) 0.0156(4) Uani 1 1 d . . . C2 C 0.8446(3) -0.07169(19) 0.21639(12) 0.0156(4) Uani 1 1 d . . . C3 C 0.7899(3) 0.13859(19) 0.23462(12) 0.0160(4) Uani 1 1 d . . . C4 C 0.9655(3) -0.13274(19) 0.44577(11) 0.0160(4) Uani 1 1 d . . . C5 C 0.8371(3) -0.2189(2) 0.49157(12) 0.0193(4) Uani 1 1 d . . . H5 H 0.6867 -0.2046 0.4972 0.023 Uiso 1 1 calc R . . C6 C 0.9321(4) -0.3267(2) 0.52924(13) 0.0230(5) Uani 1 1 d . . . H6 H 0.8483 -0.3883 0.5615 0.028 Uiso 1 1 calc R . . C7 C 1.1501(4) -0.3433(2) 0.51927(13) 0.0245(5) Uani 1 1 d . . . H7 H 1.2143 -0.4177 0.5457 0.029 Uiso 1 1 calc R . . C8 C 1.1837(3) -0.1579(2) 0.43930(12) 0.0173(4) Uani 1 1 d . . . C9 C 0.7683(3) -0.16379(19) 0.09619(12) 0.0158(4) Uani 1 1 d . . . C10 C 0.8993(3) -0.1620(2) 0.02818(12) 0.0195(4) Uani 1 1 d . . . H10 H 1.0509 -0.1617 0.0306 0.023 Uiso 1 1 calc R . . C11 C 0.8026(4) -0.1606(2) -0.04392(13) 0.0231(5) Uani 1 1 d . . . H11 H 0.8875 -0.1593 -0.0924 0.028 Uiso 1 1 calc R . . C12 C 0.5829(3) -0.1612(2) -0.04493(13) 0.0217(5) Uani 1 1 d . . . H12 H 0.5190 -0.1598 -0.0950 0.026 Uiso 1 1 calc R . . C13 C 0.5484(3) -0.1646(2) 0.08990(12) 0.0187(4) Uani 1 1 d . . . C14 C 0.7067(3) 0.36357(19) 0.24864(12) 0.0186(4) Uani 1 1 d . . . C15 C 0.8530(3) 0.4622(2) 0.25510(13) 0.0225(5) Uani 1 1 d . . . H15 H 0.9929 0.4571 0.2305 0.027 Uiso 1 1 calc R . . C16 C 0.7900(4) 0.5687(2) 0.29844(13) 0.0244(5) Uani 1 1 d . . . H16 H 0.8868 0.6383 0.3048 0.029 Uiso 1 1 calc R . . C17 C 0.5857(4) 0.5727(2) 0.33223(13) 0.0274(5) Uani 1 1 d . . . H17 H 0.5439 0.6466 0.3617 0.033 Uiso 1 1 calc R . . C18 C 0.5042(3) 0.3764(2) 0.28436(13) 0.0206(5) 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 Cl1 0.0192(3) 0.0273(3) 0.0275(3) 0.0028(2) 0.0040(2) -0.0032(2) Cl2 0.0192(3) 0.0490(4) 0.0202(3) -0.0034(2) 0.0039(2) -0.0016(2) Cl3 0.0220(3) 0.0243(3) 0.0445(4) 0.0009(3) -0.0002(2) -0.0047(2) O1 0.0202(7) 0.0168(7) 0.0144(7) -0.0034(6) -0.0022(6) 0.0022(6) O2 0.0215(7) 0.0154(7) 0.0146(7) -0.0048(6) -0.0048(6) 0.0018(6) O3 0.0265(8) 0.0137(7) 0.0175(8) -0.0014(6) 0.0005(6) -0.0001(6) N1 0.0155(8) 0.0157(9) 0.0158(9) -0.0041(7) -0.0014(7) -0.0015(7) N2 0.0171(8) 0.0155(9) 0.0170(9) -0.0017(7) -0.0002(7) -0.0013(7) N3 0.0144(8) 0.0166(9) 0.0177(9) -0.0019(7) 0.0000(7) -0.0008(7) N4 0.0212(9) 0.0225(10) 0.0192(9) -0.0026(8) -0.0032(7) 0.0029(7) N5 0.0213(9) 0.0247(10) 0.0193(9) -0.0018(8) -0.0040(7) -0.0022(7) N6 0.0308(10) 0.0210(10) 0.0287(11) 0.0003(8) 0.0026(8) 0.0036(8) C1 0.0118(9) 0.0191(10) 0.0160(10) -0.0013(8) -0.0009(8) -0.0020(8) C2 0.0105(9) 0.0175(10) 0.0192(11) -0.0043(8) -0.0010(8) -0.0005(7) C3 0.0139(10) 0.0145(10) 0.0193(11) -0.0005(8) 0.0006(8) -0.0018(8) C4 0.0223(10) 0.0156(10) 0.0107(10) -0.0037(8) -0.0024(8) -0.0001(8) C5 0.0166(10) 0.0247(11) 0.0170(11) -0.0051(9) 0.0008(8) -0.0036(8) C6 0.0300(12) 0.0211(11) 0.0179(11) -0.0004(9) 0.0011(9) -0.0054(9) C7 0.0319(12) 0.0216(12) 0.0199(11) 0.0011(9) -0.0047(9) 0.0029(9) C8 0.0196(10) 0.0189(11) 0.0136(10) -0.0040(8) 0.0017(8) -0.0027(8) C9 0.0212(10) 0.0113(10) 0.0152(10) -0.0029(8) -0.0025(8) -0.0010(8) C10 0.0181(10) 0.0187(11) 0.0219(11) -0.0037(9) 0.0000(9) -0.0023(8) C11 0.0298(12) 0.0228(12) 0.0167(11) -0.0029(9) 0.0020(9) -0.0029(9) C12 0.0274(11) 0.0231(11) 0.0152(11) -0.0018(9) -0.0050(9) -0.0027(9) C13 0.0209(10) 0.0177(11) 0.0176(11) -0.0026(8) 0.0010(8) -0.0021(8) C14 0.0268(11) 0.0115(10) 0.0173(11) 0.0008(8) -0.0023(9) 0.0011(8) C15 0.0227(11) 0.0193(11) 0.0247(12) 0.0045(9) -0.0007(9) -0.0013(9) C16 0.0380(13) 0.0126(10) 0.0231(12) 0.0014(9) -0.0082(10) -0.0041(9) C17 0.0441(14) 0.0165(11) 0.0216(12) -0.0025(9) -0.0003(10) 0.0053(10) C18 0.0240(11) 0.0150(10) 0.0226(12) 0.0034(9) -0.0020(9) -0.0005(8) _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 Cl1 C8 1.737(2) . ? Cl2 C13 1.738(2) . ? Cl3 C18 1.735(2) . ? O1 C1 1.337(2) . ? O1 C4 1.399(2) . ? O3 C3 1.350(2) . ? O3 C14 1.397(2) . ? N2 C2 1.321(2) . ? N2 C3 1.330(3) . ? N1 C1 1.324(3) . ? N1 C2 1.328(2) . ? N5 C13 1.315(3) . ? N5 C12 1.346(3) . ? O2 C2 1.346(2) . ? O2 C9 1.399(2) . ? N3 C3 1.319(3) . ? N3 C1 1.331(2) . ? C9 C10 1.372(3) . ? C9 C13 1.383(3) . ? N4 C8 1.315(3) . ? N4 C7 1.341(3) . ? C4 C5 1.372(3) . ? C4 C8 1.384(3) . ? N6 C18 1.318(3) . ? N6 C17 1.340(3) . ? C5 C6 1.378(3) . ? C5 H5 0.9500 . ? C7 C6 1.374(3) . ? C7 H7 0.9500 . ? C14 C15 1.377(3) . ? C14 C18 1.380(3) . ? C6 H6 0.9500 . ? C15 C16 1.382(3) . ? C15 H15 0.9500 . ? C11 C12 1.374(3) . ? C11 C10 1.382(3) . ? C11 H11 0.9500 . ? C16 C17 1.372(3) . ? C16 H16 0.9500 . ? C10 H10 0.9500 . ? C12 H12 0.9500 . ? C17 H17 0.9500 . ? 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 C4 118.76(15) . . ? C3 O3 C14 118.55(15) . . ? C2 N2 C3 111.94(17) . . ? C1 N1 C2 112.07(17) . . ? C13 N5 C12 116.75(18) . . ? C2 O2 C9 117.60(14) . . ? C3 N3 C1 111.85(17) . . ? C10 C9 C13 119.26(19) . . ? C10 C9 O2 120.45(17) . . ? C13 C9 O2 120.03(17) . . ? C8 N4 C7 116.59(18) . . ? N1 C1 N3 127.89(18) . . ? N1 C1 O1 118.85(17) . . ? N3 C1 O1 113.25(17) . . ? N3 C3 N2 128.22(18) . . ? N3 C3 O3 119.28(18) . . ? N2 C3 O3 112.47(17) . . ? N2 C2 N1 127.94(19) . . ? N2 C2 O2 118.82(17) . . ? N1 C2 O2 113.24(16) . . ? C5 C4 C8 118.72(18) . . ? C5 C4 O1 120.68(17) . . ? C8 C4 O1 120.07(18) . . ? C18 N6 C17 116.98(19) . . ? N4 C8 C4 124.01(19) . . ? N4 C8 Cl1 117.03(15) . . ? C4 C8 Cl1 118.95(15) . . ? C4 C5 C6 118.28(19) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? N4 C7 C6 123.60(19) . . ? N4 C7 H7 118.2 . . ? C6 C7 H7 118.2 . . ? C15 C14 C18 118.90(19) . . ? C15 C14 O3 120.23(18) . . ? C18 C14 O3 120.53(19) . . ? N6 C18 C14 123.7(2) . . ? N6 C18 Cl3 117.18(17) . . ? C14 C18 Cl3 119.07(16) . . ? N5 C13 C9 123.90(19) . . ? N5 C13 Cl2 117.02(16) . . ? C9 C13 Cl2 119.07(16) . . ? C7 C6 C5 118.8(2) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C14 C15 C16 118.0(2) . . ? C14 C15 H15 121.0 . . ? C16 C15 H15 121.0 . . ? C12 C11 C10 119.5(2) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C17 C16 C15 119.0(2) . . ? C17 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? C9 C10 C11 117.54(19) . . ? C9 C10 H10 121.2 . . ? C11 C10 H10 121.2 . . ? N5 C12 C11 123.02(19) . . ? N5 C12 H12 118.5 . . ? C11 C12 H12 118.5 . . ? N6 C17 C16 123.3(2) . . ? N6 C17 H17 118.3 . . ? C16 C17 H17 118.3 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.394 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.067 # Attachment '2.ethylacetate.cif' data_etoac-s _database_code_depnum_ccdc_archive 'CCDC 293561' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,4,6-tris(2-chloro-3-pyridyloxy)-1,3,5-triazine, ethylacetate ; _chemical_name_common '2,4,6-tris(2-chloro-3-pyridyloxy)-1,3,5-triazine, ethylacetate' _chemical_melting_point ? _chemical_formula_moiety 'C18 H9 Cl3 N6 O3, 0.38(C4 H8 O2)' _chemical_formula_sum 'C19.52 H12.04 Cl3 N6 O3.76' _chemical_formula_weight 496.94 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2474(13) _cell_length_b 10.134(2) _cell_length_c 16.828(4) _cell_angle_alpha 93.843(3) _cell_angle_beta 92.715(3) _cell_angle_gamma 90.321(3) _cell_volume 1061.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1821 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 28.11 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.464 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9008 _exptl_absorpt_correction_T_max 0.9508 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8293 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0738 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4161 _reflns_number_gt 2950 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997) and squeeze' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. Squeeze programme has been used to remove electron density peaks due to disordered solvent. ; _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^)+(0.0656P)^2^+0.3468P] 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_extinction_coef ? _refine_ls_number_reflns 4161 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0839 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1411 _refine_ls_wR_factor_gt 0.1333 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 Cl1 Cl 0.84637(13) 0.45574(9) 0.11805(5) 0.0246(2) Uani 1 1 d . . . Cl2 Cl -0.12037(14) 0.33469(11) 0.32079(5) 0.0316(3) Uani 1 1 d . . . Cl3 Cl -0.18140(14) 0.75515(9) 0.23036(6) 0.0310(3) Uani 1 1 d . . . O1 O 0.3823(3) 0.4901(2) 0.08585(13) 0.0168(5) Uani 1 1 d . . . O2 O 0.3519(3) 0.3275(2) 0.32865(13) 0.0167(5) Uani 1 1 d . . . O3 O 0.2589(4) 0.7653(2) 0.30189(13) 0.0187(5) Uani 1 1 d . . . N1 N 0.3801(4) 0.4033(3) 0.20794(16) 0.0148(6) Uani 1 1 d . . . N2 N 0.3024(4) 0.5506(3) 0.31856(16) 0.0164(6) Uani 1 1 d . . . N3 N 0.3132(4) 0.6308(3) 0.18900(16) 0.0154(6) Uani 1 1 d . . . N4 N 0.7715(4) 0.2409(3) 0.02553(17) 0.0210(7) Uani 1 1 d . . . N5 N -0.0572(4) 0.3362(3) 0.47538(17) 0.0230(7) Uani 1 1 d . . . N6 N -0.0584(5) 0.9785(3) 0.17766(18) 0.0261(7) Uani 1 1 d . . . C1 C 0.3603(5) 0.5066(3) 0.16510(19) 0.0136(7) Uani 1 1 d . . . C2 C 0.3432(5) 0.4331(3) 0.28427(19) 0.0153(7) Uani 1 1 d . . . C3 C 0.2922(5) 0.6444(3) 0.2670(2) 0.0143(7) Uani 1 1 d . . . C4 C 0.4624(5) 0.3698(3) 0.05456(19) 0.0145(7) Uani 1 1 d . . . C5 C 0.3326(5) 0.2836(3) 0.00843(19) 0.0188(8) Uani 1 1 d . . . H5 H 0.1827 0.2980 0.0030 0.023 Uiso 1 1 calc R . . C6 C 0.4245(6) 0.1748(4) -0.0301(2) 0.0234(8) Uani 1 1 d . . . H6 H 0.3392 0.1130 -0.0629 0.028 Uiso 1 1 calc R . . C7 C 0.6426(6) 0.1582(4) -0.0199(2) 0.0244(8) Uani 1 1 d . . . H7 H 0.7050 0.0835 -0.0467 0.029 Uiso 1 1 calc R . . C8 C 0.6795(5) 0.3446(3) 0.06105(19) 0.0162(7) Uani 1 1 d . . . C9 C 0.2596(5) 0.3397(3) 0.40308(19) 0.0148(7) Uani 1 1 d . . . C10 C 0.3877(5) 0.3419(3) 0.4715(2) 0.0186(8) Uani 1 1 d . . . H10 H 0.5395 0.3442 0.4698 0.022 Uiso 1 1 calc R . . C11 C 0.2878(5) 0.3407(3) 0.5434(2) 0.0209(8) Uani 1 1 d . . . H11 H 0.3704 0.3417 0.5924 0.025 Uiso 1 1 calc R . . C12 C 0.0683(6) 0.3380(4) 0.5428(2) 0.0230(8) Uani 1 1 d . . . H12 H 0.0015 0.3374 0.5923 0.028 Uiso 1 1 calc R . . C13 C 0.0416(5) 0.3375(3) 0.4082(2) 0.0194(8) Uani 1 1 d . . . C14 C 0.2089(5) 0.8690(3) 0.25334(19) 0.0161(7) Uani 1 1 d . . . C15 C 0.3553(6) 0.9674(4) 0.2446(2) 0.0231(8) Uani 1 1 d . . . H15 H 0.4966 0.9634 0.2677 0.028 Uiso 1 1 calc R . . C16 C 0.2923(6) 1.0721(3) 0.2014(2) 0.0241(8) Uani 1 1 d . . . H16 H 0.3899 1.1420 0.1939 0.029 Uiso 1 1 calc R . . C17 C 0.0859(6) 1.0742(4) 0.1691(2) 0.0278(9) Uani 1 1 d . . . H17 H 0.0437 1.1470 0.1393 0.033 Uiso 1 1 calc R . . C18 C 0.0053(5) 0.8794(3) 0.2193(2) 0.0196(8) 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 Cl1 0.0181(4) 0.0289(5) 0.0258(5) -0.0033(4) -0.0027(4) -0.0019(4) Cl2 0.0187(5) 0.0558(7) 0.0201(5) 0.0040(4) -0.0020(4) 0.0012(4) Cl3 0.0184(5) 0.0257(5) 0.0484(6) -0.0019(4) 0.0026(4) -0.0054(4) O1 0.0215(12) 0.0174(13) 0.0120(12) 0.0028(10) 0.0036(10) 0.0042(10) O2 0.0203(12) 0.0179(13) 0.0130(12) 0.0042(10) 0.0070(10) 0.0045(10) O3 0.0243(13) 0.0140(12) 0.0178(12) 0.0001(10) 0.0011(10) 0.0004(10) N1 0.0140(14) 0.0159(15) 0.0148(15) 0.0022(12) 0.0039(12) 0.0002(12) N2 0.0183(14) 0.0158(16) 0.0155(15) 0.0022(12) 0.0021(12) 0.0015(12) N3 0.0097(13) 0.0193(16) 0.0178(15) 0.0036(12) 0.0023(11) -0.0010(11) N4 0.0206(16) 0.0228(17) 0.0200(16) 0.0028(13) 0.0042(13) 0.0035(13) N5 0.0153(15) 0.0354(19) 0.0193(16) 0.0054(14) 0.0055(13) 0.0015(13) N6 0.0292(17) 0.0241(18) 0.0246(17) 0.0002(14) -0.0024(14) 0.0063(14) C1 0.0086(15) 0.0182(18) 0.0142(17) 0.0019(14) 0.0017(13) -0.0007(13) C2 0.0099(16) 0.0186(19) 0.0180(18) 0.0048(15) 0.0013(14) -0.0015(14) C3 0.0045(15) 0.0178(18) 0.0201(18) -0.0017(14) -0.0001(13) -0.0031(13) C4 0.0156(17) 0.0175(18) 0.0112(16) 0.0039(14) 0.0051(13) -0.0003(14) C5 0.0134(16) 0.028(2) 0.0152(18) 0.0052(15) 0.0013(14) -0.0048(15) C6 0.028(2) 0.024(2) 0.0173(19) -0.0023(16) 0.0002(16) -0.0028(16) C7 0.032(2) 0.022(2) 0.0185(19) -0.0026(16) 0.0046(16) 0.0024(17) C8 0.0181(17) 0.0191(19) 0.0115(17) 0.0025(14) 0.0001(14) -0.0037(14) C9 0.0179(17) 0.0142(17) 0.0136(17) 0.0061(14) 0.0072(14) -0.0002(14) C10 0.0161(17) 0.0166(19) 0.0237(19) 0.0035(15) 0.0040(15) -0.0008(14) C11 0.0250(19) 0.024(2) 0.0139(18) 0.0025(15) 0.0000(15) -0.0016(16) C12 0.027(2) 0.026(2) 0.0171(19) 0.0043(16) 0.0096(16) 0.0021(16) C13 0.0173(17) 0.025(2) 0.0169(18) 0.0058(15) -0.0003(15) -0.0001(15) C14 0.0226(18) 0.0108(17) 0.0145(17) -0.0031(14) 0.0032(14) 0.0021(14) C15 0.0254(19) 0.019(2) 0.024(2) -0.0035(16) 0.0004(16) 0.0012(16) C16 0.034(2) 0.0130(19) 0.025(2) -0.0043(15) 0.0062(17) -0.0046(16) C17 0.044(2) 0.018(2) 0.021(2) 0.0017(16) 0.0027(18) 0.0093(18) C18 0.0195(18) 0.0135(18) 0.025(2) -0.0037(15) 0.0035(15) -0.0022(14) _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 O2 C2 1.345(4) . ? O2 C9 1.402(4) . ? O1 C1 1.347(4) . ? O1 C4 1.399(4) . ? O3 C3 1.345(4) . ? O3 C14 1.401(4) . ? Cl1 C8 1.739(3) . ? Cl2 C13 1.744(3) . ? Cl3 C18 1.737(4) . ? N1 C1 1.314(4) . ? N1 C2 1.331(4) . ? N3 C3 1.324(4) . ? N3 C1 1.333(4) . ? N2 C2 1.320(4) . ? N2 C3 1.328(4) . ? C9 C13 1.369(4) . ? C9 C10 1.369(5) . ? N4 C8 1.321(4) . ? N4 C7 1.335(5) . ? N5 C13 1.314(4) . ? N5 C12 1.347(4) . ? C4 C5 1.366(5) . ? C4 C8 1.382(4) . ? N6 C18 1.315(4) . ? N6 C17 1.340(5) . ? C18 C14 1.378(5) . ? C10 C11 1.389(5) . ? C10 H10 0.9500 . ? C5 C6 1.383(5) . ? C5 H5 0.9500 . ? C7 C6 1.378(5) . ? C7 H7 0.9500 . ? C14 C15 1.369(5) . ? C6 H6 0.9500 . ? C15 C16 1.375(5) . ? C15 H15 0.9500 . ? C16 C17 1.376(5) . ? C16 H16 0.9500 . ? C11 C12 1.371(5) . ? C11 H11 0.9500 . ? C17 H17 0.9500 . ? C12 H12 0.9500 . ? 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 O2 C9 117.5(2) . . ? C1 O1 C4 118.4(2) . . ? C3 O3 C14 118.6(2) . . ? C1 N1 C2 112.0(3) . . ? C3 N3 C1 111.5(3) . . ? C2 N2 C3 112.6(3) . . ? C13 C9 C10 119.3(3) . . ? C13 C9 O2 120.6(3) . . ? C10 C9 O2 119.9(3) . . ? C8 N4 C7 116.4(3) . . ? N2 C2 N1 127.5(3) . . ? N2 C2 O2 119.3(3) . . ? N1 C2 O2 113.2(3) . . ? C13 N5 C12 116.4(3) . . ? C5 C4 C8 118.8(3) . . ? C5 C4 O1 120.4(3) . . ? C8 C4 O1 120.3(3) . . ? N1 C1 N3 128.5(3) . . ? N1 C1 O1 118.7(3) . . ? N3 C1 O1 112.7(3) . . ? N4 C8 C4 124.1(3) . . ? N4 C8 Cl1 116.9(2) . . ? C4 C8 Cl1 119.0(3) . . ? N3 C3 N2 127.7(3) . . ? N3 C3 O3 119.3(3) . . ? N2 C3 O3 113.0(3) . . ? C18 N6 C17 116.9(3) . . ? N5 C13 C9 124.4(3) . . ? N5 C13 Cl2 116.6(2) . . ? C9 C13 Cl2 119.0(3) . . ? N6 C18 C14 123.9(3) . . ? N6 C18 Cl3 116.9(3) . . ? C14 C18 Cl3 119.1(3) . . ? C9 C10 C11 117.6(3) . . ? C9 C10 H10 121.2 . . ? C11 C10 H10 121.2 . . ? C4 C5 C6 118.5(3) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? N4 C7 C6 123.9(3) . . ? N4 C7 H7 118.1 . . ? C6 C7 H7 118.1 . . ? C15 C14 C18 118.9(3) . . ? C15 C14 O3 120.6(3) . . ? C18 C14 O3 120.3(3) . . ? C7 C6 C5 118.4(3) . . ? C7 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? C14 C15 C16 118.2(3) . . ? C14 C15 H15 120.9 . . ? C16 C15 H15 120.9 . . ? C15 C16 C17 119.0(4) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C12 C11 C10 119.0(3) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? N6 C17 C16 123.1(3) . . ? N6 C17 H17 118.5 . . ? C16 C17 H17 118.5 . . ? N5 C12 C11 123.2(3) . . ? N5 C12 H12 118.4 . . ? C11 C12 H12 118.4 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.724 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.088 # Attachment '2 guest free.cif' data_epan5_m _database_code_depnum_ccdc_archive 'CCDC 293562' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,4,6-tris(2-chloro-3-pyridyloxy)-1,3,5-triazine ; _chemical_name_common 2,4,6-tris(2-chloro-3-pyridyloxy)-1,3,5-triazine _chemical_melting_point ? _chemical_formula_moiety 'C18 H9 Cl3 N6 O3' _chemical_formula_sum 'C18 H9 Cl3 N6 O3' _chemical_formula_weight 463.66 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' _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 17.2490(9) _cell_length_b 17.2490(9) _cell_length_c 12.0227(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3097.9(4) _cell_formula_units_Z 6 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 9077 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 24.44 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1404 _exptl_absorpt_coefficient_mu 0.477 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8861 _exptl_absorpt_correction_T_max 0.9233 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29302 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 25.48 _reflns_number_total 3657 _reflns_number_gt 2767 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997) and squeeze' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1058P)^2^+1.3627P] 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 SHELXL _refine_ls_extinction_coef 0.0005(5) _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 0.16(14) _refine_ls_number_reflns 3657 _refine_ls_number_parameters 272 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0663 _refine_ls_wR_factor_ref 0.1910 _refine_ls_wR_factor_gt 0.1769 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _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 Cl1 Cl 0.5309(3) 0.77046(16) 0.6939(2) 0.1673(14) Uani 1 1 d . . . Cl2 Cl 0.14747(14) -0.01018(19) 0.69302(16) 0.1277(9) Uani 1 1 d . . . Cl3 Cl 0.35538(13) 0.82961(13) 0.43813(16) 0.1105(6) Uani 1 1 d . . . O1 O 0.5052(2) 0.7229(3) 0.9289(4) 0.0767(10) Uani 1 1 d . . . O2 O 0.1117(2) -0.0613(2) 0.9286(4) 0.0721(9) Uani 1 1 d . . . O3 O 0.3213(2) 0.8105(2) 0.1999(4) 0.0716(10) Uani 1 1 d . . . N1 N 0.3903(3) 0.7563(3) 0.9277(4) 0.0644(10) Uani 1 1 d . . . N2 N 0.6532(4) 0.9226(5) 0.7736(5) 0.0998(18) Uani 1 1 d . . . N3 N -0.0283(2) -0.0905(2) 0.9305(4) 0.0562(9) Uani 1 1 d . . . N4 N 0.3107(4) 0.0767(5) 0.7651(5) 0.0974(18) Uani 1 1 d . . . N5 N 0.4108(3) 0.7481(3) 0.2012(4) 0.0576(9) Uani 1 1 d . . . N6 N 0.4887(4) 0.9843(4) 0.3754(4) 0.0845(14) Uani 1 1 d . . . C1 C 0.4179(3) 0.6980(3) 0.9270(4) 0.0591(11) Uani 1 1 d . . . C2 C 0.5671(4) 0.8145(4) 0.9093(5) 0.0729(14) Uani 1 1 d . . . C3 C 0.6115(4) 0.8701(4) 0.9938(6) 0.0810(16) Uani 1 1 d . . . H3 H 0.5977 0.8523 1.0676 0.097 Uiso 1 1 calc R . . C4 C 0.6804(6) 0.9571(5) 0.9645(8) 0.106(3) Uani 1 1 d . . . H4 H 0.7136 0.9988 1.0190 0.128 Uiso 1 1 calc R . . C5 C 0.6965(5) 0.9777(5) 0.8578(9) 0.097(2) Uani 1 1 d . . . H5 H 0.7418 1.0352 0.8402 0.117 Uiso 1 1 calc R . . C6 C 0.5898(5) 0.8424(5) 0.8009(5) 0.0870(19) Uani 1 1 d . . . C7 C 0.0566(4) -0.0262(4) 0.9296(5) 0.0628(12) Uani 1 1 d . . . C8 C 0.2029(3) 0.0006(4) 0.9049(5) 0.0657(13) Uani 1 1 d . . . C9 C 0.2661(4) 0.0269(4) 0.9823(6) 0.0811(16) Uani 1 1 d . . . H9 H 0.2510 0.0093 1.0559 0.097 Uiso 1 1 calc R . . C10 C 0.3551(5) 0.0810(5) 0.9518(9) 0.111(3) Uani 1 1 d . . . H10 H 0.4012 0.1000 1.0035 0.134 Uiso 1 1 calc R . . C11 C 0.3716(5) 0.1046(5) 0.8441(9) 0.104(2) Uani 1 1 d . . . H11 H 0.4307 0.1437 0.8238 0.125 Uiso 1 1 calc R . . C12 C 0.2268(4) 0.0262(4) 0.7974(5) 0.0761(15) Uani 1 1 d . . . C13 C 0.3303(3) 0.7379(3) 0.2017(4) 0.0550(10) Uani 1 1 d . . . C14 C 0.3972(4) 0.8911(3) 0.2295(5) 0.0641(13) Uani 1 1 d . . . C15 C 0.4489(6) 0.9531(4) 0.1497(6) 0.091(2) Uani 1 1 d . . . H15 H 0.4367 0.9419 0.0742 0.110 Uiso 1 1 calc R . . C16 C 0.5181(5) 1.0306(5) 0.1871(8) 0.103(2) Uani 1 1 d . . . H16 H 0.5526 1.0754 0.1363 0.124 Uiso 1 1 calc R . . C17 C 0.5390(5) 1.0451(4) 0.2983(8) 0.093(2) Uani 1 1 d . . . H17 H 0.5891 1.0982 0.3206 0.111 Uiso 1 1 calc R . . C18 C 0.4201(4) 0.9086(4) 0.3407(5) 0.0723(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 Cl1 0.276(4) 0.0994(14) 0.0755(11) -0.0098(11) -0.0134(19) 0.0557(19) Cl2 0.0977(13) 0.202(2) 0.0732(10) -0.0065(13) -0.0216(10) 0.0668(15) Cl3 0.1095(13) 0.1078(12) 0.0746(10) 0.0137(10) 0.0105(10) 0.0247(10) O1 0.067(2) 0.082(2) 0.090(3) 0.001(2) -0.007(2) 0.0440(19) O2 0.071(2) 0.0665(19) 0.084(2) 0.006(2) 0.005(2) 0.0378(17) O3 0.076(2) 0.060(2) 0.085(3) 0.0001(18) -0.010(2) 0.0386(18) N1 0.068(3) 0.070(2) 0.061(2) -0.003(2) -0.012(2) 0.039(2) N2 0.096(4) 0.096(4) 0.097(4) 0.017(4) 0.023(4) 0.040(4) N3 0.049(2) 0.057(2) 0.066(2) 0.005(2) 0.003(2) 0.0282(18) N4 0.072(4) 0.124(5) 0.096(4) 0.021(3) 0.014(3) 0.048(3) N5 0.060(2) 0.054(2) 0.057(2) 0.0062(19) 0.0062(19) 0.0273(18) N6 0.084(3) 0.074(3) 0.088(3) -0.009(3) -0.001(3) 0.034(3) C1 0.062(3) 0.076(3) 0.045(2) -0.001(2) -0.005(2) 0.038(3) C2 0.067(3) 0.082(4) 0.071(3) 0.005(3) -0.005(3) 0.038(3) C3 0.062(3) 0.088(4) 0.080(4) 0.011(3) -0.006(3) 0.028(3) C4 0.096(5) 0.076(4) 0.129(8) -0.018(4) -0.047(5) 0.030(4) C5 0.069(4) 0.069(4) 0.151(8) 0.026(5) 0.011(4) 0.031(3) C6 0.108(5) 0.077(4) 0.072(4) 0.003(3) -0.002(3) 0.043(4) C7 0.073(3) 0.072(3) 0.058(3) 0.014(3) 0.004(3) 0.047(3) C8 0.055(3) 0.074(3) 0.072(4) -0.001(3) -0.005(2) 0.036(3) C9 0.084(4) 0.098(4) 0.073(3) 0.000(3) -0.011(3) 0.055(4) C10 0.079(5) 0.103(5) 0.159(9) -0.036(6) -0.054(6) 0.051(4) C11 0.078(4) 0.080(5) 0.142(8) 0.011(5) 0.001(5) 0.030(4) C12 0.056(3) 0.087(4) 0.080(4) -0.008(3) -0.015(3) 0.032(3) C13 0.062(3) 0.059(3) 0.048(2) 0.004(2) -0.002(2) 0.033(2) C14 0.074(3) 0.054(3) 0.068(3) 0.004(2) 0.002(3) 0.035(3) C15 0.129(6) 0.060(4) 0.084(4) 0.004(3) 0.013(4) 0.046(4) C16 0.092(5) 0.075(4) 0.114(6) 0.010(5) 0.015(5) 0.020(4) C17 0.087(5) 0.053(3) 0.125(6) -0.010(3) 0.004(4) 0.025(3) C18 0.073(4) 0.066(3) 0.074(3) 0.004(3) -0.002(3) 0.031(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 Cl3 C18 1.719(6) . ? O3 C13 1.337(6) . ? O3 C14 1.398(7) . ? N5 C13 1.309(6) . ? N5 C13 1.325(6) 3_565 ? C13 N5 1.325(6) 2_665 ? C18 N6 1.317(8) . ? C18 C14 1.384(9) . ? C14 C15 1.380(8) . ? N6 C17 1.342(9) . ? C15 C16 1.349(11) . ? C15 H15 0.9300 . ? C16 C17 1.375(11) . ? C16 H16 0.9300 . ? Cl2 C12 1.727(6) . ? N3 C7 1.324(7) . ? N3 C7 1.334(7) 3 ? O2 C7 1.357(6) . ? O2 C8 1.419(6) . ? C8 C9 1.329(8) . ? C8 C12 1.361(9) . ? C7 N3 1.334(7) 2 ? C10 C11 1.345(12) . ? C10 C9 1.389(11) . ? C10 H10 0.9300 . ? C12 N4 1.321(8) . ? N4 C11 1.315(11) . ? C9 H9 0.9300 . ? C11 H11 0.9300 . ? Cl1 C6 1.722(7) . ? O1 C1 1.345(6) . ? O1 C2 1.417(7) . ? N1 C1 1.310(6) . ? N1 C1 1.325(6) 2_665 ? C1 N1 1.325(6) 3_565 ? C2 C3 1.343(9) . ? C2 C6 1.376(9) . ? C4 C5 1.322(11) . ? C4 C3 1.416(11) . ? C4 H4 0.9300 . ? C5 N2 1.333(11) . ? C5 H5 0.9300 . ? C6 N2 1.306(9) . ? C3 H3 0.9300 . ? C17 H17 0.9300 . ? 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 C13 O3 C14 116.0(4) . . ? C13 N5 C13 111.3(4) . 3_565 ? N5 C13 N5 128.7(4) . 2_665 ? N5 C13 O3 119.1(4) . . ? N5 C13 O3 112.2(4) 2_665 . ? N6 C18 C14 122.6(6) . . ? N6 C18 Cl3 118.4(5) . . ? C14 C18 Cl3 119.0(4) . . ? C15 C14 C18 120.0(6) . . ? C15 C14 O3 121.0(6) . . ? C18 C14 O3 119.0(5) . . ? C18 N6 C17 117.8(6) . . ? C16 C15 C14 116.4(7) . . ? C16 C15 H15 121.8 . . ? C14 C15 H15 121.8 . . ? C15 C16 C17 121.8(7) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C7 N3 C7 111.2(5) . 3 ? C7 O2 C8 115.3(4) . . ? C9 C8 C12 119.3(5) . . ? C9 C8 O2 121.8(5) . . ? C12 C8 O2 118.5(5) . . ? N3 C7 N3 128.8(5) . 2 ? N3 C7 O2 110.8(4) . . ? N3 C7 O2 120.4(5) 2 . ? C11 C10 C9 117.0(7) . . ? C11 C10 H10 121.5 . . ? C9 C10 H10 121.5 . . ? N4 C12 C8 123.2(6) . . ? N4 C12 Cl2 115.8(5) . . ? C8 C12 Cl2 121.0(4) . . ? C11 N4 C12 116.2(6) . . ? C8 C9 C10 119.1(7) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? N4 C11 C10 125.0(7) . . ? N4 C11 H11 117.5 . . ? C10 C11 H11 117.5 . . ? C1 O1 C2 116.9(4) . . ? C1 N1 C1 114.1(5) . 2_665 ? N1 C1 N1 125.9(5) . 3_565 ? N1 C1 O1 122.2(5) . . ? N1 C1 O1 111.8(4) 3_565 . ? C3 C2 C6 120.4(6) . . ? C3 C2 O1 120.9(5) . . ? C6 C2 O1 118.1(6) . . ? C5 C4 C3 118.6(7) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 N2 125.3(7) . . ? C4 C5 H5 117.4 . . ? N2 C5 H5 117.4 . . ? N2 C6 C2 123.3(7) . . ? N2 C6 Cl1 117.1(5) . . ? C2 C6 Cl1 119.6(5) . . ? C2 C3 C4 116.4(7) . . ? C2 C3 H3 121.8 . . ? C4 C3 H3 121.8 . . ? C6 N2 C5 115.9(6) . . ? N6 C17 C16 121.4(6) . . ? N6 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 25.48 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.247 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.053 # Attachment '2.nitromethane.cif' data_nitromethane-s _database_code_depnum_ccdc_archive 'CCDC 293563' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,4,6-tris(2-chloro-3-pyridyloxy)-1,3,5-triazine, nitromethane ; _chemical_name_common '2,4,6-tris(2-chloro-3-pyridyloxy)-1,3,5-triazine, nitromethane' _chemical_melting_point ? _chemical_formula_moiety 'C18 H9 Cl3 N6 O3, 0.55(C H3 N O2)' _chemical_formula_sum 'C18.55 H10.65 Cl3 N6.55 O4.1' _chemical_formula_weight 497.05 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3045(7) _cell_length_b 10.1891(11) _cell_length_c 17.0142(19) _cell_angle_alpha 93.247(2) _cell_angle_beta 92.607(2) _cell_angle_gamma 90.350(2) _cell_volume 1090.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1701 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.452 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9231 _exptl_absorpt_correction_T_max 0.9734 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7576 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0966 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.20 _diffrn_reflns_theta_max 26.08 _reflns_number_total 4293 _reflns_number_gt 2051 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997) and SQUEEZE' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0507P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4293 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1356 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1229 _refine_ls_wR_factor_gt 0.1061 _refine_ls_goodness_of_fit_ref 0.882 _refine_ls_restrained_S_all 0.882 _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 Cl1 Cl 0.84562(15) 0.45201(10) 0.11925(7) 0.0711(3) Uani 1 1 d . . . Cl2 Cl -0.12135(17) 0.32579(13) 0.32401(7) 0.0886(4) Uani 1 1 d . . . Cl3 Cl -0.17939(17) 0.75212(10) 0.23023(8) 0.0880(4) Uani 1 1 d . . . O1 O 0.3872(3) 0.4903(2) 0.08820(13) 0.0434(6) Uani 1 1 d . . . O2 O 0.3457(3) 0.3246(2) 0.32771(13) 0.0445(6) Uani 1 1 d . . . O3 O 0.2546(4) 0.7594(2) 0.30103(13) 0.0489(6) Uani 1 1 d . . . N1 N 0.3770(4) 0.4008(2) 0.20839(16) 0.0375(7) Uani 1 1 d . . . N2 N 0.2968(4) 0.5457(2) 0.31783(16) 0.0406(7) Uani 1 1 d . . . N3 N 0.3151(4) 0.6277(2) 0.19032(17) 0.0397(7) Uani 1 1 d . . . N4 N 0.7674(5) 0.2432(3) 0.0276(2) 0.0582(9) Uani 1 1 d . . . N5 N -0.0506(5) 0.3311(3) 0.4761(2) 0.0599(9) Uani 1 1 d . . . N6 N -0.0562(5) 0.9734(3) 0.1776(2) 0.0698(10) Uani 1 1 d . . . C1 C 0.3603(5) 0.5051(3) 0.1660(2) 0.0370(8) Uani 1 1 d . . . C2 C 0.3389(5) 0.4298(3) 0.2833(2) 0.0382(8) Uani 1 1 d . . . C3 C 0.2891(5) 0.6386(3) 0.2661(2) 0.0390(8) Uani 1 1 d . . . C4 C 0.4657(5) 0.3714(3) 0.05695(19) 0.0376(8) Uani 1 1 d . . . C5 C 0.3348(6) 0.2876(3) 0.0114(2) 0.0492(9) Uani 1 1 d . . . H5 H 0.1896 0.3026 0.0063 0.059 Uiso 1 1 calc R . . C6 C 0.4246(7) 0.1802(4) -0.0268(2) 0.0652(11) Uani 1 1 d . . . H6 H 0.3416 0.1210 -0.0587 0.078 Uiso 1 1 calc R . . C7 C 0.6396(8) 0.1631(4) -0.0166(2) 0.0663(12) Uani 1 1 d . . . H7 H 0.6993 0.0904 -0.0424 0.080 Uiso 1 1 calc R . . C8 C 0.6789(5) 0.3453(3) 0.0630(2) 0.0426(9) Uani 1 1 d . . . C9 C 0.2582(6) 0.3353(3) 0.4023(2) 0.0396(9) Uani 1 1 d . . . C10 C 0.3865(6) 0.3398(3) 0.4680(2) 0.0528(10) Uani 1 1 d . . . H10 H 0.5334 0.3420 0.4650 0.063 Uiso 1 1 calc R . . C11 C 0.2922(7) 0.3411(4) 0.5407(2) 0.0618(11) Uani 1 1 d . . . H11 H 0.3744 0.3454 0.5876 0.074 Uiso 1 1 calc R . . C12 C 0.0751(7) 0.3359(4) 0.5410(2) 0.0623(11) Uani 1 1 d . . . H12 H 0.0122 0.3356 0.5893 0.075 Uiso 1 1 calc R . . C13 C 0.0429(6) 0.3313(3) 0.4081(2) 0.0496(10) Uani 1 1 d . . . C14 C 0.2062(6) 0.8631(3) 0.2526(2) 0.0458(9) Uani 1 1 d . . . C15 C 0.3517(6) 0.9614(3) 0.2444(2) 0.0563(10) Uani 1 1 d . . . H15 H 0.4886 0.9577 0.2669 0.068 Uiso 1 1 calc R . . C16 C 0.2870(8) 1.0664(3) 0.2013(3) 0.0674(12) Uani 1 1 d . . . H16 H 0.3801 1.1355 0.1944 0.081 Uiso 1 1 calc R . . C17 C 0.0857(9) 1.0672(4) 0.1691(3) 0.0775(14) Uani 1 1 d . . . H17 H 0.0454 1.1375 0.1395 0.093 Uiso 1 1 calc R . . C18 C 0.0059(6) 0.8739(3) 0.2191(2) 0.0553(10) 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 Cl1 0.0500(6) 0.0834(7) 0.0772(8) -0.0096(6) -0.0110(5) -0.0037(5) Cl2 0.0538(7) 0.1509(11) 0.0601(8) 0.0048(7) -0.0086(6) 0.0050(7) Cl3 0.0584(7) 0.0708(7) 0.1337(12) 0.0005(7) 0.0012(7) -0.0114(6) O1 0.0530(15) 0.0438(14) 0.0347(16) 0.0058(11) 0.0098(12) 0.0085(11) O2 0.0520(15) 0.0420(13) 0.0417(16) 0.0119(12) 0.0134(12) 0.0087(11) O3 0.0652(17) 0.0368(13) 0.0439(16) -0.0023(12) -0.0012(13) 0.0040(12) N1 0.0424(17) 0.0382(15) 0.0330(19) 0.0068(14) 0.0071(14) 0.0014(13) N2 0.0513(19) 0.0348(16) 0.0365(18) 0.0064(14) 0.0044(14) 0.0020(13) N3 0.0452(17) 0.0370(16) 0.037(2) 0.0032(14) 0.0049(14) 0.0022(13) N4 0.057(2) 0.056(2) 0.061(2) -0.0033(18) 0.0080(18) 0.0157(18) N5 0.056(2) 0.081(2) 0.045(2) 0.0125(18) 0.0136(19) 0.0028(17) N6 0.075(3) 0.050(2) 0.083(3) 0.005(2) -0.010(2) 0.0125(19) C1 0.0299(19) 0.044(2) 0.038(2) 0.0051(18) 0.0033(16) -0.0022(15) C2 0.0312(19) 0.041(2) 0.043(2) 0.0131(18) 0.0010(17) 0.0050(16) C3 0.037(2) 0.0340(19) 0.045(3) -0.0029(18) 0.0040(18) 0.0000(15) C4 0.046(2) 0.0375(19) 0.031(2) 0.0083(16) 0.0066(17) 0.0050(17) C5 0.045(2) 0.053(2) 0.050(3) 0.005(2) -0.0011(19) -0.0073(19) C6 0.082(3) 0.055(3) 0.058(3) 0.000(2) 0.000(2) -0.012(2) C7 0.090(4) 0.051(2) 0.057(3) -0.007(2) 0.011(3) 0.009(3) C8 0.044(2) 0.046(2) 0.038(2) 0.0054(18) 0.0004(17) 0.0019(17) C9 0.042(2) 0.0377(19) 0.042(3) 0.0117(17) 0.0128(19) 0.0041(16) C10 0.049(2) 0.061(2) 0.048(3) 0.013(2) -0.005(2) 0.0003(19) C11 0.068(3) 0.075(3) 0.042(3) 0.002(2) -0.002(2) 0.000(2) C12 0.078(3) 0.069(3) 0.042(3) 0.009(2) 0.020(2) 0.001(2) C13 0.052(3) 0.057(2) 0.040(3) 0.0063(19) 0.001(2) 0.0054(19) C14 0.057(3) 0.0307(18) 0.049(3) -0.0030(17) 0.000(2) 0.0060(18) C15 0.054(2) 0.045(2) 0.068(3) -0.011(2) -0.004(2) -0.006(2) C16 0.095(4) 0.030(2) 0.077(3) -0.001(2) 0.014(3) -0.004(2) C17 0.112(4) 0.047(3) 0.075(4) 0.009(2) 0.000(3) 0.022(3) C18 0.057(3) 0.041(2) 0.067(3) -0.008(2) 0.006(2) 0.0038(19) _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 Cl1 C8 1.726(4) . ? Cl2 C13 1.725(4) . ? Cl3 C18 1.723(4) . ? O3 C3 1.359(3) . ? O3 C14 1.403(4) . ? N1 C1 1.319(4) . ? N1 C2 1.325(4) . ? O1 C1 1.342(4) . ? O1 C4 1.398(3) . ? N2 C2 1.323(4) . ? N2 C3 1.328(4) . ? O2 C2 1.346(3) . ? O2 C9 1.405(4) . ? N3 C3 1.305(4) . ? N3 C1 1.331(4) . ? C4 C5 1.367(5) . ? C4 C8 1.372(4) . ? C9 C10 1.349(5) . ? C9 C13 1.366(4) . ? C8 N4 1.312(4) . ? N4 C7 1.322(5) . ? N5 C13 1.323(4) . ? N5 C12 1.328(5) . ? N6 C18 1.318(4) . ? N6 C17 1.323(5) . ? C14 C18 1.369(5) . ? C14 C15 1.372(4) . ? C5 C6 1.379(5) . ? C5 H5 0.9300 . ? C15 C16 1.384(5) . ? C15 H15 0.9300 . ? C10 C11 1.395(5) . ? C10 H10 0.9300 . ? C6 C7 1.372(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C11 C12 1.369(5) . ? C11 H11 0.9300 . ? C16 C17 1.359(6) . ? C16 H16 0.9300 . ? C12 H12 0.9300 . ? C17 H17 0.9300 . ? 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 C3 O3 C14 118.2(3) . . ? C1 N1 C2 111.6(3) . . ? C1 O1 C4 119.0(2) . . ? C2 N2 C3 111.1(3) . . ? C2 O2 C9 118.6(2) . . ? C3 N3 C1 111.8(3) . . ? N2 C2 N1 128.5(3) . . ? N2 C2 O2 118.2(3) . . ? N1 C2 O2 113.3(3) . . ? N1 C1 N3 128.0(3) . . ? N1 C1 O1 118.6(3) . . ? N3 C1 O1 113.4(3) . . ? C5 C4 C8 119.1(3) . . ? C5 C4 O1 119.9(3) . . ? C8 C4 O1 120.5(3) . . ? C10 C9 C13 120.0(3) . . ? C10 C9 O2 120.0(3) . . ? C13 C9 O2 119.8(3) . . ? N3 C3 N2 128.9(3) . . ? N3 C3 O3 119.1(3) . . ? N2 C3 O3 112.0(3) . . ? N4 C8 C4 123.9(3) . . ? N4 C8 Cl1 116.8(3) . . ? C4 C8 Cl1 119.3(3) . . ? C8 N4 C7 116.5(3) . . ? C13 N5 C12 116.9(3) . . ? C18 N6 C17 116.9(4) . . ? C18 C14 C15 119.1(3) . . ? C18 C14 O3 120.1(3) . . ? C15 C14 O3 120.5(3) . . ? C4 C5 C6 118.0(4) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? N5 C13 C9 123.3(4) . . ? N5 C13 Cl2 116.7(3) . . ? C9 C13 Cl2 120.0(3) . . ? N6 C18 C14 123.7(4) . . ? N6 C18 Cl3 116.8(3) . . ? C14 C18 Cl3 119.5(3) . . ? C14 C15 C16 117.4(4) . . ? C14 C15 H15 121.3 . . ? C16 C15 H15 121.3 . . ? C9 C10 C11 118.0(4) . . ? C9 C10 H10 121.0 . . ? C11 C10 H10 121.0 . . ? C7 C6 C5 118.2(4) . . ? C7 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? N4 C7 C6 124.3(4) . . ? N4 C7 H7 117.9 . . ? C6 C7 H7 117.9 . . ? C12 C11 C10 118.1(4) . . ? C12 C11 H11 121.0 . . ? C10 C11 H11 121.0 . . ? C17 C16 C15 119.2(4) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? N5 C12 C11 123.7(4) . . ? N5 C12 H12 118.1 . . ? C11 C12 H12 118.1 . . ? N6 C17 C16 123.7(4) . . ? N6 C17 H17 118.2 . . ? C16 C17 H17 118.2 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.08 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.286 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.050 # Attachment '2.methyl ethyl ketone.cif' data_an463_m _database_code_depnum_ccdc_archive 'CCDC 298173' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2, 4, 6-tris(2-chloro-3-pyridinoxy)-1 ,3, 5-triazine, ethylmethylketone ; _chemical_name_common ;2, 4, 6-tris(2-chloro-3-pyridinoxy)-1 ,3, 5-triazine, ethylmethylketone ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H9 N6 O3 Cl3, 0.5(C4 H8 O)' _chemical_formula_sum 'C20 H13 Cl3 N6 O3.50' _chemical_formula_weight 498.71 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2589(5) _cell_length_b 10.1316(8) _cell_length_c 16.8663(13) _cell_angle_alpha 86.0240(10) _cell_angle_beta 87.5270(10) _cell_angle_gamma 88.2010(10) _cell_volume 1065.54(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3900 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 26.01 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 506 _exptl_absorpt_coefficient_mu 0.470 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8836 _exptl_absorpt_correction_T_max 0.9634 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7788 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 26.02 _reflns_number_total 4190 _reflns_number_gt 3259 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. Squeeze programme has been used to remove electron density peaks due to disordered solvent. ; _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^)+(0.0647P)^2^+0.2611P] 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_extinction_coef ? _refine_ls_number_reflns 4190 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1168 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _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 Cl1 Cl 1.34788(10) -0.04618(7) 0.38460(4) 0.02522(18) Uani 1 1 d . . . Cl2 Cl 0.39497(10) -0.15906(7) 0.17858(4) 0.02633(18) Uani 1 1 d . . . Cl3 Cl 0.30942(11) 0.25448(7) 0.27147(4) 0.03160(19) Uani 1 1 d . . . O1 O 0.8809(3) -0.01094(16) 0.41408(9) 0.0173(4) Uani 1 1 d . . . O2 O 0.8684(3) -0.17326(16) 0.17101(9) 0.0183(4) Uani 1 1 d . . . O3 O 0.7467(3) 0.26427(16) 0.19760(10) 0.0205(4) Uani 1 1 d . . . N1 N 0.8883(3) -0.0982(2) 0.29201(11) 0.0170(4) Uani 1 1 d . . . N2 N 0.8047(3) 0.0495(2) 0.18102(12) 0.0178(5) Uani 1 1 d . . . N3 N 0.8082(3) 0.1297(2) 0.31051(11) 0.0173(4) Uani 1 1 d . . . N4 N 1.2817(3) -0.2603(2) 0.47692(12) 0.0227(5) Uani 1 1 d . . . N5 N 0.4564(3) -0.1615(2) 0.02439(12) 0.0213(5) Uani 1 1 d . . . N6 N 0.4231(4) 0.4788(2) 0.32274(13) 0.0278(5) Uani 1 1 d . . . C1 C 0.8605(4) 0.0061(2) 0.33505(14) 0.0160(5) Uani 1 1 d . . . C2 C 0.8515(4) -0.0680(2) 0.21562(14) 0.0170(5) Uani 1 1 d . . . C3 C 0.7866(4) 0.1436(2) 0.23258(14) 0.0168(5) Uani 1 1 d . . . C4 C 0.9671(4) -0.1310(2) 0.44571(13) 0.0166(5) Uani 1 1 d . . . C5 C 0.8396(4) -0.2178(3) 0.49154(14) 0.0210(6) Uani 1 1 d . . . H5 H 0.6891 -0.2032 0.4963 0.025 Uiso 1 1 calc R . . C6 C 0.9371(4) -0.3261(3) 0.53017(15) 0.0245(6) Uani 1 1 d . . . H6 H 0.8545 -0.3880 0.5623 0.029 Uiso 1 1 calc R . . C7 C 1.1561(4) -0.3438(3) 0.52165(15) 0.0250(6) Uani 1 1 d . . . H7 H 1.2215 -0.4189 0.5488 0.030 Uiso 1 1 calc R . . C8 C 1.1860(4) -0.1574(3) 0.44060(14) 0.0188(5) Uani 1 1 d . . . C9 C 0.7749(4) -0.1610(2) 0.09684(14) 0.0171(5) Uani 1 1 d . . . C10 C 0.9027(4) -0.1622(2) 0.02832(14) 0.0197(5) Uani 1 1 d . . . H10 H 1.0542 -0.1627 0.0300 0.024 Uiso 1 1 calc R . . C11 C 0.8018(4) -0.1627(3) -0.04295(15) 0.0228(6) Uani 1 1 d . . . H11 H 0.8836 -0.1631 -0.0917 0.027 Uiso 1 1 calc R . . C12 C 0.5817(4) -0.1627(2) -0.04263(15) 0.0221(6) Uani 1 1 d . . . H12 H 0.5148 -0.1635 -0.0921 0.027 Uiso 1 1 calc R . . C13 C 0.5558(4) -0.1609(2) 0.09197(14) 0.0193(5) Uani 1 1 d . . . C14 C 0.6926(4) 0.3681(2) 0.24595(14) 0.0188(5) Uani 1 1 d . . . C15 C 0.8337(4) 0.4664(3) 0.25324(14) 0.0218(6) Uani 1 1 d . . . H15 H 0.9736 0.4620 0.2292 0.026 Uiso 1 1 calc R . . C16 C 0.7670(5) 0.5731(3) 0.29674(15) 0.0253(6) Uani 1 1 d . . . H16 H 0.8606 0.6433 0.3031 0.030 Uiso 1 1 calc R . . C17 C 0.5639(5) 0.5747(3) 0.33019(16) 0.0289(7) Uani 1 1 d . . . H17 H 0.5198 0.6473 0.3603 0.035 Uiso 1 1 calc R . . C18 C 0.4904(4) 0.3788(3) 0.28131(15) 0.0216(6) Uani 1 1 d . . . O4 O 0.3244(8) 0.4917(5) -0.0659(3) 0.0538(13) Uani 0.50 1 d P . . C19 C 0.2550(6) 0.5131(3) 0.0758(2) 0.0501(9) Uani 1 1 d . . . H19A H 0.1013 0.5129 0.0669 0.075 Uiso 1 1 calc R . . H19B H 0.2895 0.5952 0.0993 0.075 Uiso 1 1 calc R . . H19C H 0.2939 0.4371 0.1120 0.075 Uiso 1 1 calc R . . C20 C 0.3810(7) 0.5036(4) -0.0040(3) 0.0596(11) 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 Cl1 0.0212(3) 0.0277(4) 0.0257(3) 0.0030(3) 0.0042(3) -0.0030(3) Cl2 0.0223(3) 0.0385(4) 0.0181(3) -0.0039(3) 0.0036(3) -0.0008(3) Cl3 0.0243(4) 0.0278(4) 0.0420(4) 0.0044(3) -0.0009(3) -0.0050(3) O1 0.0216(9) 0.0184(9) 0.0120(8) -0.0022(7) -0.0022(7) 0.0024(7) O2 0.0240(9) 0.0176(9) 0.0135(8) -0.0035(7) -0.0030(7) 0.0020(7) O3 0.0321(10) 0.0134(9) 0.0158(8) -0.0010(7) 0.0013(7) -0.0001(8) N1 0.0169(11) 0.0191(11) 0.0154(10) -0.0044(8) -0.0010(8) -0.0002(9) N2 0.0220(11) 0.0167(11) 0.0148(10) -0.0023(8) 0.0003(8) -0.0010(9) N3 0.0181(11) 0.0172(11) 0.0167(10) -0.0018(8) -0.0011(8) 0.0001(9) N4 0.0265(12) 0.0233(12) 0.0180(11) -0.0006(9) -0.0018(9) 0.0035(10) N5 0.0242(12) 0.0198(12) 0.0202(11) -0.0021(9) -0.0023(9) -0.0018(9) N6 0.0325(13) 0.0229(12) 0.0265(12) 0.0021(10) 0.0065(10) 0.0059(10) C1 0.0124(12) 0.0193(13) 0.0167(12) -0.0024(10) 0.0000(9) -0.0028(10) C2 0.0140(12) 0.0204(13) 0.0170(12) -0.0042(10) 0.0010(10) -0.0027(10) C3 0.0154(12) 0.0179(13) 0.0169(12) 0.0000(10) -0.0005(10) -0.0016(10) C4 0.0216(13) 0.0163(13) 0.0122(11) -0.0032(9) -0.0013(10) 0.0006(10) C5 0.0226(13) 0.0246(14) 0.0162(12) -0.0053(10) 0.0008(10) -0.0012(11) C6 0.0316(15) 0.0247(15) 0.0166(12) 0.0015(11) 0.0025(11) -0.0050(12) C7 0.0321(15) 0.0225(15) 0.0196(13) 0.0031(11) -0.0020(11) 0.0025(12) C8 0.0222(13) 0.0220(14) 0.0123(11) -0.0021(10) 0.0006(10) -0.0033(11) C9 0.0227(13) 0.0128(12) 0.0161(12) -0.0029(9) -0.0039(10) 0.0000(10) C10 0.0228(13) 0.0165(13) 0.0201(12) -0.0023(10) 0.0003(11) -0.0027(10) C11 0.0303(15) 0.0216(14) 0.0163(12) -0.0036(10) 0.0053(11) -0.0016(11) C12 0.0339(15) 0.0176(13) 0.0153(12) -0.0008(10) -0.0053(11) -0.0008(11) C13 0.0251(14) 0.0164(13) 0.0162(12) -0.0016(10) 0.0015(10) -0.0023(11) C14 0.0279(14) 0.0143(13) 0.0139(12) 0.0009(10) -0.0014(10) 0.0032(11) C15 0.0270(14) 0.0198(14) 0.0181(12) 0.0027(10) 0.0003(11) -0.0010(11) C16 0.0396(16) 0.0150(13) 0.0211(13) 0.0020(10) -0.0014(12) -0.0034(12) C17 0.0445(18) 0.0192(14) 0.0220(14) 0.0002(11) 0.0027(13) 0.0059(13) C18 0.0231(14) 0.0199(14) 0.0210(13) 0.0040(10) -0.0003(11) -0.0010(11) C19 0.067(3) 0.037(2) 0.045(2) 0.0010(16) 0.0091(18) -0.0020(18) C20 0.078(3) 0.036(2) 0.065(3) -0.0005(18) 0.003(2) -0.016(2) O4 0.065(3) 0.070(4) 0.028(2) 0.002(2) -0.016(2) -0.008(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 Cl1 C8 1.741(2) . ? Cl2 C13 1.739(2) . ? Cl3 C18 1.741(3) . ? O1 C1 1.343(3) . ? O1 C4 1.396(3) . ? O3 C3 1.341(3) . ? O3 C14 1.400(3) . ? O2 C2 1.346(3) . ? O2 C9 1.400(3) . ? N2 C2 1.319(3) . ? N2 C3 1.334(3) . ? N1 C1 1.325(3) . ? N1 C2 1.331(3) . ? N5 C13 1.322(3) . ? N5 C12 1.348(3) . ? N4 C8 1.313(3) . ? N4 C7 1.344(3) . ? N3 C3 1.325(3) . ? N3 C1 1.327(3) . ? C9 C10 1.377(3) . ? C9 C13 1.377(4) . ? N6 C18 1.319(3) . ? N6 C17 1.348(4) . ? C4 C5 1.380(3) . ? C4 C8 1.388(4) . ? C7 C6 1.380(4) . ? C7 H7 0.9500 . ? C15 C14 1.367(3) . ? C15 C16 1.391(4) . ? C15 H15 0.9500 . ? C18 C14 1.380(4) . ? C11 C12 1.378(4) . ? C11 C10 1.382(4) . ? C11 H11 0.9500 . ? C6 C5 1.376(4) . ? C6 H6 0.9500 . ? C16 C17 1.369(4) . ? C16 H16 0.9500 . ? C5 H5 0.9500 . ? C10 H10 0.9500 . ? C12 H12 0.9500 . ? C17 H17 0.9500 . ? C19 C20 1.538(5) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 O4 1.132(6) . ? C20 C20 1.501(9) 2_665 ? 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 C4 118.57(18) . . ? C3 O3 C14 118.45(18) . . ? C2 O2 C9 117.38(19) . . ? C2 N2 C3 112.5(2) . . ? C1 N1 C2 111.9(2) . . ? C13 N5 C12 116.4(2) . . ? C8 N4 C7 116.7(2) . . ? C3 N3 C1 112.1(2) . . ? N1 C1 N3 128.2(2) . . ? N1 C1 O1 118.6(2) . . ? N3 C1 O1 113.2(2) . . ? C10 C9 C13 119.5(2) . . ? C10 C9 O2 119.8(2) . . ? C13 C9 O2 120.4(2) . . ? C18 N6 C17 116.6(2) . . ? N2 C2 N1 127.7(2) . . ? N2 C2 O2 119.0(2) . . ? N1 C2 O2 113.3(2) . . ? C5 C4 C8 118.6(2) . . ? C5 C4 O1 120.2(2) . . ? C8 C4 O1 120.7(2) . . ? N3 C3 N2 127.5(2) . . ? N3 C3 O3 119.6(2) . . ? N2 C3 O3 112.9(2) . . ? N4 C8 C4 124.3(2) . . ? N4 C8 Cl1 117.05(19) . . ? C4 C8 Cl1 118.7(2) . . ? N4 C7 C6 123.3(3) . . ? N4 C7 H7 118.4 . . ? C6 C7 H7 118.4 . . ? C14 C15 C16 118.3(2) . . ? C14 C15 H15 120.9 . . ? C16 C15 H15 120.9 . . ? N6 C18 C14 124.0(2) . . ? N6 C18 Cl3 116.9(2) . . ? C14 C18 Cl3 119.2(2) . . ? C12 C11 C10 119.4(2) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C5 C6 C7 119.2(2) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C17 C16 C15 118.6(3) . . ? C17 C16 H16 120.7 . . ? C15 C16 H16 120.7 . . ? C15 C14 C18 119.0(2) . . ? C15 C14 O3 120.2(2) . . ? C18 C14 O3 120.5(2) . . ? C6 C5 C4 118.0(2) . . ? C6 C5 H5 121.0 . . ? C4 C5 H5 121.0 . . ? C9 C10 C11 117.4(2) . . ? C9 C10 H10 121.3 . . ? C11 C10 H10 121.3 . . ? N5 C12 C11 123.3(2) . . ? N5 C12 H12 118.4 . . ? C11 C12 H12 118.4 . . ? N5 C13 C9 123.9(2) . . ? N5 C13 Cl2 116.62(19) . . ? C9 C13 Cl2 119.43(19) . . ? N6 C17 C16 123.6(2) . . ? N6 C17 H17 118.2 . . ? C16 C17 H17 118.2 . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O4 C20 C20 115.5(5) . 2_665 ? O4 C20 C19 130.9(5) . . ? C20 C20 C19 113.4(5) 2_665 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.055 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.074