Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 X-Sun-Charset: us-ascii X-Sun-Content-Lines: 1540 data_global _journal_coden_Cambridge 188 loop_ _publ_author_name 'Alder, Mark J.' 'Bates, Vanessa M.' 'Cross, Wendy' 'Flower, Kevin R.' 'Pritchard, R.' _publ_contact_author_name 'Dr. K.R. Flower' _publ_contact_author_address ; Department of Chemistry Faraday Building UMIST PO Box 88 Manchester M60 1QD ; _publ_contact_author_email k.r.flower@umist.ac.uk data_comp2b _database_code_CSD 165166 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26.78 H24.99 Cl1.10 N2 O P S' _chemical_formula_weight 492.92 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 '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' 'S' 'S' 0.1246 0.1234 '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 8.8661(12) _cell_length_b 10.5570(18) _cell_length_c 14.267(3) _cell_angle_alpha 110.513(16) _cell_angle_beta 94.713(13) _cell_angle_gamma 91.063(12) _cell_volume 1244.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block' _exptl_crystal_colour 'red orange' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 515 _exptl_absorpt_coefficient_mu 0.335 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8919 _exptl_absorpt_correction_T_max 0.9361 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71069 _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 4676 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 24.97 _reflns_number_total 4368 _reflns_number_gt 3720 _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^)+(0.1281P)^2^+1.1007P] 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_number_reflns 4368 _refine_ls_number_parameters 392 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0704 _refine_ls_R_factor_gt 0.0610 _refine_ls_wR_factor_ref 0.1918 _refine_ls_wR_factor_gt 0.1813 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.112 _refine_ls_shift/su_mean 0.017 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 S1 S 0.30538(9) 0.17017(8) 0.47410(6) 0.0349(3) Uani 1 1 d . . . N1 N 0.1763(3) 0.1577(3) 0.92941(19) 0.0324(6) Uani 1 1 d . . . N2 N 0.2159(3) 0.0981(3) 0.98955(18) 0.0316(6) Uani 1 1 d . . . P1 P 0.25136(8) 0.26478(7) 0.61049(5) 0.0254(2) Uani 1 1 d . . . O1 O 0.4367(3) -0.0175(3) 0.8919(2) 0.0456(7) Uani 1 1 d . . . C1 C 0.2638(3) 0.1301(3) 0.8469(2) 0.0291(6) Uani 1 1 d . . . C2 C 0.3871(4) 0.0441(3) 0.8284(2) 0.0334(7) Uani 1 1 d . . . C3 C 0.4596(4) 0.0229(3) 0.7422(2) 0.0352(7) Uani 1 1 d . . . C4 C 0.4152(3) 0.0857(3) 0.6755(2) 0.0316(7) Uani 1 1 d . . . C5 C 0.2954(3) 0.1735(3) 0.6940(2) 0.0275(6) Uani 1 1 d . . . C6 C 0.2212(3) 0.1941(3) 0.7793(2) 0.0292(6) Uani 1 1 d . . . C7 C 0.1302(3) 0.1229(3) 1.0728(2) 0.0309(7) Uani 1 1 d . . . C8 C 0.0109(4) 0.2084(3) 1.0930(2) 0.0381(7) Uani 1 1 d . . . H8 H -0.0192 0.2542 1.0492 0.046 Uiso 1 1 calc R . . C9 C -0.0632(4) 0.2262(4) 1.1773(3) 0.0405(8) Uani 1 1 d . . . C10 C -0.0200(4) 0.1617(3) 1.2444(2) 0.0341(7) Uani 1 1 d . . . C11 C 0.0975(4) 0.0743(3) 1.2222(2) 0.0350(7) Uani 1 1 d . . . C12 C 0.1720(4) 0.0542(3) 1.1371(2) 0.0335(7) Uani 1 1 d . . . C13 C -0.0970(4) 0.1872(4) 1.3394(3) 0.0433(8) Uani 1 1 d . . . H13A H -0.1123 0.1025 1.3504 0.065 Uiso 1 1 calc R . . H13B H -0.1943 0.2254 1.3328 0.065 Uiso 1 1 calc R . . H13C H -0.0340 0.2501 1.3959 0.065 Uiso 1 1 calc R . . C14 C 0.0523(3) 0.2963(3) 0.6153(2) 0.0290(6) Uani 1 1 d . . . C15 C -0.0523(4) 0.1875(4) 0.5933(2) 0.0363(7) Uani 1 1 d . . . C16 C -0.2047(4) 0.2079(4) 0.5864(3) 0.0464(9) Uani 1 1 d . . . C17 C -0.2556(4) 0.3346(5) 0.6000(3) 0.0542(10) Uani 1 1 d . . . C18 C -0.1552(4) 0.4424(5) 0.6233(4) 0.0585(11) Uani 1 1 d . . . C19 C 0.0000(4) 0.4245(4) 0.6307(3) 0.0439(8) Uani 1 1 d . . . C20 C 0.3518(3) 0.4281(3) 0.6680(2) 0.0295(6) Uani 1 1 d . . . C21 C 0.3826(4) 0.5033(3) 0.6091(3) 0.0378(7) Uani 1 1 d . . . C22 C 0.4655(4) 0.6246(4) 0.6494(3) 0.0478(9) Uani 1 1 d . . . C23 C 0.5201(5) 0.6709(4) 0.7474(4) 0.0553(10) Uani 1 1 d . . . C24 C 0.4908(6) 0.5990(5) 0.8074(3) 0.0676(13) Uani 1 1 d . . . H24 H 0.5283 0.6323 0.8756 0.081 Uiso 1 1 calc R . . C25 C 0.4057(5) 0.4769(4) 0.7684(3) 0.0527(10) Uani 1 1 d . . . C26 C 0.1852(12) 0.7058(9) 1.1379(6) 0.078(3) Uani 0.551(5) 1 d PD . . H26A H 0.2277 0.7538 1.2073 0.094 Uiso 0.551(5) 1 calc PR . . H26B H 0.1040 0.7581 1.1211 0.094 Uiso 0.551(5) 1 calc PR . . Cl1 Cl 0.3382(3) 0.6799(4) 1.0477(2) 0.0968(12) Uani 0.551(5) 1 d PD . . Cl2 Cl 0.1182(5) 0.5463(4) 1.1230(4) 0.1257(16) Uani 0.551(5) 1 d PD . . H12 H 0.256(4) -0.008(4) 1.119(3) 0.039(9) Uiso 1 1 d . . . H4 H 0.467(5) 0.073(4) 0.618(3) 0.049(11) Uiso 1 1 d . . . H6 H 0.140(4) 0.258(3) 0.796(2) 0.029(8) Uiso 1 1 d . . . H19 H 0.073(4) 0.505(4) 0.647(3) 0.041(10) Uiso 1 1 d . . . H15 H -0.020(4) 0.097(4) 0.584(3) 0.038(9) Uiso 1 1 d . . . H11 H 0.131(4) 0.021(4) 1.265(3) 0.041(10) Uiso 1 1 d . . . H9 H -0.147(5) 0.284(4) 1.184(3) 0.044(10) Uiso 1 1 d . . . H3 H 0.542(4) -0.038(4) 0.730(3) 0.036(9) Uiso 1 1 d . . . H17 H -0.356(5) 0.345(4) 0.589(3) 0.043(10) Uiso 1 1 d . . . H16 H -0.266(5) 0.143(4) 0.576(3) 0.048(11) Uiso 1 1 d . . . H1 H 0.385(6) -0.002(5) 0.935(4) 0.059(14) Uiso 1 1 d . . . H25 H 0.389(5) 0.423(5) 0.812(3) 0.062(12) Uiso 1 1 d . . . H22 H 0.476(5) 0.677(5) 0.611(4) 0.065(13) Uiso 1 1 d . . . C27 C 0.3728(17) 0.556(3) 1.0296(9) 0.135(10) Uani 0.415(11) 1 d PD . . H27A H 0.4592 0.5060 1.0396 0.203 Uiso 0.415(11) 1 calc PR . . H27B H 0.3747 0.6419 1.0853 0.203 Uiso 0.415(11) 1 calc PR . . H27C H 0.3773 0.5736 0.9674 0.203 Uiso 0.415(11) 1 calc PR . . C28 C 0.224(2) 0.4725(13) 1.0240(14) 0.146(10) Uani 0.415(11) 1 d PD . . H28A H 0.2272 0.3873 0.9673 0.175 Uiso 0.415(11) 1 calc PR . . H28B H 0.2296 0.4489 1.0848 0.175 Uiso 0.415(11) 1 calc PR . . C29 C 0.068(2) 0.523(2) 1.014(2) 0.160(12) Uani 0.415(11) 1 d PD . . H29A H 0.0602 0.5884 1.0815 0.192 Uiso 0.415(11) 1 calc PR . . H29B H 0.0827 0.5782 0.9724 0.192 Uiso 0.415(11) 1 calc PR . . H21 H 0.352(4) 0.461(4) 0.539(3) 0.047(10) Uiso 1 1 d . . . H23 H 0.574(6) 0.757(6) 0.766(4) 0.092(17) Uiso 1 1 d . . . H18 H -0.199(5) 0.522(5) 0.633(4) 0.066(13) Uiso 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 S1 0.0392(5) 0.0404(5) 0.0262(4) 0.0116(3) 0.0101(3) 0.0040(3) N1 0.0357(14) 0.0353(14) 0.0277(13) 0.0128(11) 0.0044(11) -0.0001(11) N2 0.0337(14) 0.0377(14) 0.0245(12) 0.0129(11) 0.0023(10) -0.0027(11) P1 0.0246(4) 0.0294(4) 0.0248(4) 0.0121(3) 0.0057(3) 0.0022(3) O1 0.0450(14) 0.0667(17) 0.0408(14) 0.0352(13) 0.0141(12) 0.0219(13) C1 0.0292(15) 0.0317(15) 0.0276(15) 0.0117(12) 0.0035(12) -0.0008(12) C2 0.0315(15) 0.0406(17) 0.0330(16) 0.0191(14) 0.0025(13) 0.0053(13) C3 0.0324(16) 0.0417(18) 0.0359(17) 0.0175(14) 0.0080(13) 0.0117(14) C4 0.0287(15) 0.0394(17) 0.0311(16) 0.0163(13) 0.0095(12) 0.0058(13) C5 0.0273(14) 0.0281(14) 0.0298(15) 0.0130(12) 0.0051(12) 0.0010(11) C6 0.0285(15) 0.0308(15) 0.0310(16) 0.0132(13) 0.0067(12) 0.0037(12) C7 0.0321(15) 0.0365(16) 0.0236(14) 0.0104(12) 0.0014(12) -0.0068(13) C8 0.0465(19) 0.0408(18) 0.0302(16) 0.0162(14) 0.0043(14) 0.0064(15) C9 0.0435(19) 0.0443(19) 0.0338(17) 0.0125(15) 0.0077(14) 0.0067(16) C10 0.0336(16) 0.0399(17) 0.0240(15) 0.0062(13) 0.0003(12) -0.0075(13) C11 0.0357(17) 0.0449(18) 0.0262(15) 0.0161(14) -0.0009(13) -0.0043(14) C12 0.0295(15) 0.0422(18) 0.0295(16) 0.0140(14) 0.0014(12) 0.0005(13) C13 0.0432(19) 0.056(2) 0.0317(17) 0.0156(16) 0.0090(14) 0.0019(16) C14 0.0251(14) 0.0377(16) 0.0252(14) 0.0118(12) 0.0051(11) 0.0037(12) C15 0.0346(17) 0.0410(19) 0.0357(17) 0.0156(14) 0.0075(13) -0.0016(14) C16 0.0305(17) 0.060(2) 0.049(2) 0.0195(18) 0.0068(15) -0.0085(17) C17 0.0236(17) 0.075(3) 0.064(3) 0.024(2) 0.0073(16) 0.0092(17) C18 0.036(2) 0.055(2) 0.084(3) 0.022(2) 0.011(2) 0.0170(18) C19 0.0323(17) 0.0389(19) 0.059(2) 0.0152(17) 0.0038(16) 0.0040(15) C20 0.0251(14) 0.0314(15) 0.0334(16) 0.0118(13) 0.0074(12) 0.0039(12) C21 0.0406(18) 0.0341(17) 0.044(2) 0.0200(15) 0.0088(15) 0.0032(14) C22 0.047(2) 0.0372(19) 0.067(3) 0.0263(19) 0.0167(18) 0.0024(15) C23 0.048(2) 0.038(2) 0.075(3) 0.015(2) 0.000(2) -0.0112(17) C24 0.091(3) 0.053(2) 0.049(2) 0.013(2) -0.015(2) -0.028(2) C25 0.068(3) 0.050(2) 0.039(2) 0.0167(17) -0.0065(18) -0.0203(19) C26 0.131(9) 0.085(6) 0.031(4) 0.031(4) 0.025(4) 0.002(6) Cl1 0.0779(19) 0.110(2) 0.103(2) 0.0352(18) 0.0208(15) 0.0049(16) Cl2 0.121(3) 0.120(3) 0.138(3) 0.046(2) 0.020(2) -0.013(2) C27 0.108(12) 0.29(3) 0.038(6) 0.074(11) 0.058(8) 0.121(16) C28 0.27(3) 0.033(7) 0.097(12) -0.019(7) -0.032(16) 0.028(11) C29 0.129(17) 0.092(13) 0.27(3) 0.099(18) -0.057(19) -0.040(11) _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 S1 P1 1.9550(11) . ? N1 N2 1.262(4) . ? N1 C1 1.411(4) . ? N2 C7 1.413(4) . ? P1 C5 1.800(3) . ? P1 C14 1.805(3) . ? P1 C20 1.808(3) . ? O1 C2 1.340(4) . ? C1 C6 1.391(4) . ? C1 C2 1.416(4) . ? C2 C3 1.385(5) . ? C3 C4 1.375(4) . ? C4 C5 1.403(4) . ? C5 C6 1.383(4) . ? C7 C8 1.386(5) . ? C7 C12 1.387(4) . ? C8 C9 1.376(5) . ? C9 C10 1.390(5) . ? C10 C11 1.387(5) . ? C10 C13 1.509(4) . ? C11 C12 1.383(5) . ? C14 C19 1.388(5) . ? C14 C15 1.392(5) . ? C15 C16 1.373(5) . ? C16 C17 1.372(6) . ? C17 C18 1.359(6) . ? C18 C19 1.393(5) . ? C20 C25 1.381(5) . ? C20 C21 1.382(4) . ? C21 C22 1.374(5) . ? C22 C23 1.353(6) . ? C23 C24 1.364(6) . ? C24 C25 1.390(6) . ? C26 Cl2 1.710(9) . ? C26 Cl1 1.904(9) . ? C27 C28 1.560(17) . ? C28 C29 1.499(17) . ? C29 C29 1.27(3) 2_567 ? 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 N2 N1 C1 114.4(3) . . ? N1 N2 C7 115.9(3) . . ? C5 P1 C14 106.22(14) . . ? C5 P1 C20 105.84(14) . . ? C14 P1 C20 106.26(14) . . ? C5 P1 S1 113.04(10) . . ? C14 P1 S1 113.02(10) . . ? C20 P1 S1 111.89(10) . . ? C6 C1 N1 115.3(3) . . ? C6 C1 C2 119.1(3) . . ? N1 C1 C2 125.6(3) . . ? O1 C2 C3 118.7(3) . . ? O1 C2 C1 122.1(3) . . ? C3 C2 C1 119.3(3) . . ? C4 C3 C2 121.0(3) . . ? C3 C4 C5 120.3(3) . . ? C6 C5 C4 119.0(3) . . ? C6 C5 P1 121.9(2) . . ? C4 C5 P1 118.9(2) . . ? C5 C6 C1 121.2(3) . . ? C8 C7 C12 119.6(3) . . ? C8 C7 N2 124.8(3) . . ? C12 C7 N2 115.5(3) . . ? C9 C8 C7 119.7(3) . . ? C8 C9 C10 121.6(3) . . ? C11 C10 C9 118.0(3) . . ? C11 C10 C13 120.8(3) . . ? C9 C10 C13 121.2(3) . . ? C12 C11 C10 121.0(3) . . ? C11 C12 C7 119.9(3) . . ? C19 C14 C15 119.1(3) . . ? C19 C14 P1 121.5(2) . . ? C15 C14 P1 119.2(2) . . ? C16 C15 C14 119.9(3) . . ? C15 C16 C17 120.7(4) . . ? C18 C17 C16 120.2(4) . . ? C17 C18 C19 120.2(4) . . ? C14 C19 C18 119.9(4) . . ? C25 C20 C21 118.8(3) . . ? C25 C20 P1 121.8(3) . . ? C21 C20 P1 119.3(3) . . ? C22 C21 C20 120.8(4) . . ? C23 C22 C21 120.2(4) . . ? C22 C23 C24 120.3(4) . . ? C23 C24 C25 120.5(4) . . ? C20 C25 C24 119.5(4) . . ? Cl2 C26 Cl1 105.2(5) . . ? C29 C28 C27 123.7(13) . . ? C29 C29 C28 140(3) 2_567 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N2 0.76(5) 1.91(5) 2.570(4) 144(5) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.150 _refine_diff_density_min -0.440 _refine_diff_density_rms 0.087 #===END data_comp4b _database_code_CSD 165167 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H29 Cl2 N4 O P S' _chemical_formula_weight 631.53 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' 'P' 'P' 0.1023 0.0942 '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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.037(2) _cell_length_b 7.6280(10) _cell_length_c 26.332(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.860(10) _cell_angle_gamma 90.00 _cell_volume 3213.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'plate' _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.349 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8875 _exptl_absorpt_correction_T_max 0.9659 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71069 _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 5205 _diffrn_reflns_av_R_equivalents 0.1420 _diffrn_reflns_av_sigmaI/netI 0.1423 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 20.01 _reflns_number_total 2744 _reflns_number_gt 1265 _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 w=1/[\s^2^(Fo^2^)+(0.0464P)^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(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2744 _refine_ls_number_parameters 389 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1586 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1432 _refine_ls_wR_factor_gt 0.1084 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.35009(17) 0.4235(3) 0.36274(9) 0.0878(9) Uani 1 d . . . Cl1 Cl 0.05129(19) 0.3567(4) 0.31615(11) 0.1326(12) Uani 1 d . . . Cl2 Cl 0.0942(2) 0.3054(5) 0.42384(13) 0.1759(17) Uani 1 d . . . P1 P 0.36083(15) 0.6806(3) 0.36394(8) 0.0617(8) Uani 1 d . . . O1 O 0.4971(8) 0.8193(11) 0.5449(3) 0.073(3) Uani 0.853(14) d P . . H1 H 0.537(6) 0.788(12) 0.534(4) 0.06(5) Uiso 0.853(14) d P . . O1B O 0.230(3) 0.988(7) 0.520(2) 0.13(2) Uiso 0.147(14) d P . . N1 N 0.4988(6) 0.6701(9) 0.4419(2) 0.059(2) Uani 1 d . . . N2 N 0.5646(6) 0.6556(9) 0.4724(3) 0.065(2) Uani 1 d . . . N3 N 0.2067(8) 0.8272(9) 0.4182(3) 0.072(2) Uani 1 d . . . N4 N 0.1447(8) 0.8486(9) 0.4444(3) 0.077(3) Uani 1 d . . . C1 C 0.4323(10) 0.8319(12) 0.5122(4) 0.066(3) Uani 1 d . . . C2 C 0.4309(7) 0.7583(10) 0.4619(4) 0.056(3) Uani 1 d . . . C3 C 0.3563(9) 0.7724(10) 0.4290(3) 0.061(3) Uani 1 d . . . C4 C 0.2839(9) 0.8438(11) 0.4473(4) 0.064(3) Uani 1 d . . . C5 C 0.2892(10) 0.9203(12) 0.4975(4) 0.079(3) Uani 1 d . . . H5 H 0.2424 0.9732 0.5098 0.095 Uiso 1 calc R . . C6 C 0.3614(10) 0.9156(12) 0.5266(4) 0.070(3) Uani 1 d . . . H6 H 0.3636 0.9716 0.5580 0.084 Uiso 1 calc R . . C7 C 0.6354(7) 0.5698(11) 0.4523(4) 0.061(3) Uani 1 d . . . C8 C 0.7066(8) 0.5636(11) 0.4845(3) 0.070(3) Uani 1 d . . . H8 H 0.7071 0.6113 0.5170 0.084 Uiso 1 calc R . . C9 C 0.7781(7) 0.4844(13) 0.4674(4) 0.082(3) Uani 1 d . . . H9 H 0.8265 0.4800 0.4889 0.099 Uiso 1 calc R . . C10 C 0.7785(8) 0.4123(11) 0.4193(4) 0.073(3) Uani 1 d . . . C11 C 0.7046(9) 0.4218(12) 0.3877(3) 0.078(3) Uani 1 d . . . H11 H 0.7038 0.3753 0.3550 0.094 Uiso 1 calc R . . C12 C 0.6318(7) 0.4996(11) 0.4042(4) 0.075(3) Uani 1 d . . . H12 H 0.5828 0.5034 0.3832 0.090 Uiso 1 calc R . . C13 C 0.8570(6) 0.3283(13) 0.4016(3) 0.105(3) Uani 1 d . . . H13A H 0.9004 0.3333 0.4285 0.158 Uiso 0.50 calc PR . . H13B H 0.8746 0.3900 0.3724 0.158 Uiso 0.50 calc PR . . H13C H 0.8458 0.2081 0.3927 0.158 Uiso 0.50 calc PR . . H13D H 0.8468 0.2876 0.3673 0.158 Uiso 0.50 calc PR . . H13E H 0.8726 0.2309 0.4234 0.158 Uiso 0.50 calc PR . . H13F H 0.9014 0.4128 0.4031 0.158 Uiso 0.50 calc PR . . C14 C 0.0637(9) 0.8430(11) 0.4177(4) 0.074(3) Uani 1 d . . . C15 C -0.0057(10) 0.8296(11) 0.4472(4) 0.080(3) Uani 1 d . . . H15 H 0.0020 0.8193 0.4824 0.097 Uiso 1 calc R . . C16 C -0.0853(8) 0.8316(11) 0.4239(5) 0.084(3) Uani 1 d . . . H16 H -0.1305 0.8274 0.4442 0.101 Uiso 1 calc R . . C17 C -0.1006(8) 0.8394(12) 0.3725(5) 0.082(3) Uani 1 d . . . C18 C -0.0338(10) 0.8532(13) 0.3428(4) 0.095(4) Uani 1 d . . . H18 H -0.0430 0.8619 0.3077 0.115 Uiso 1 calc R . . C19 C 0.0478(8) 0.8543(12) 0.3649(4) 0.094(3) Uani 1 d . . . H19 H 0.0924 0.8626 0.3442 0.112 Uiso 1 calc R . . C20 C -0.1892(7) 0.8459(12) 0.3483(4) 0.117(4) Uani 1 d . . . H20A H -0.2282 0.8377 0.3744 0.176 Uiso 0.50 calc PR . . H20B H -0.1979 0.7497 0.3251 0.176 Uiso 0.50 calc PR . . H20C H -0.1977 0.9545 0.3303 0.176 Uiso 0.50 calc PR . . H20D H -0.1877 0.8569 0.3121 0.176 Uiso 0.50 calc PR . . H20E H -0.2180 0.9449 0.3614 0.176 Uiso 0.50 calc PR . . H20F H -0.2181 0.7401 0.3562 0.176 Uiso 0.50 calc PR . . C21 C 0.2833(5) 0.7870(12) 0.3208(3) 0.057(2) Uani 1 d . . . C22 C 0.2306(6) 0.6920(11) 0.2880(3) 0.067(3) Uani 1 d . . . H22 H 0.2323 0.5702 0.2897 0.080 Uiso 1 calc R . . C23 C 0.1753(6) 0.7705(15) 0.2526(4) 0.089(3) Uani 1 d . . . H23 H 0.1394 0.7024 0.2316 0.107 Uiso 1 calc R . . C24 C 0.1737(6) 0.9531(18) 0.2487(3) 0.091(3) Uani 1 d . . . H24 H 0.1371 1.0073 0.2247 0.109 Uiso 1 calc R . . C25 C 0.2263(7) 1.0523(13) 0.2803(4) 0.090(3) Uani 1 d . . . H25 H 0.2258 1.1738 0.2774 0.108 Uiso 1 calc R . . C26 C 0.2799(6) 0.9730(12) 0.3165(3) 0.073(3) Uani 1 d . . . H26 H 0.3142 1.0417 0.3383 0.088 Uiso 1 calc R . . C27 C 0.4557(5) 0.7604(14) 0.3383(3) 0.065(3) Uani 1 d . . . C28 C 0.4961(7) 0.6608(14) 0.3031(4) 0.093(3) Uani 1 d . . . H28 H 0.4769 0.5485 0.2950 0.112 Uiso 1 calc R . . C29 C 0.5666(10) 0.729(2) 0.2795(4) 0.128(5) Uani 1 d . . . H29 H 0.5919 0.6647 0.2547 0.154 Uiso 1 calc R . . C30 C 0.5962(9) 0.892(3) 0.2944(5) 0.132(6) Uani 1 d . . . H30 H 0.6440 0.9343 0.2806 0.159 Uiso 1 calc R . . C31 C 0.5575(9) 0.9947(16) 0.3292(5) 0.111(4) Uani 1 d . . . H31 H 0.5778 1.1059 0.3377 0.134 Uiso 1 calc R . . C32 C 0.4873(7) 0.9280(16) 0.3513(3) 0.084(3) Uani 1 d . . . H32 H 0.4610 0.9953 0.3750 0.101 Uiso 1 calc R . . C33 C 0.1182(8) 0.382(2) 0.3692(4) 0.201(7) Uani 1 d . . . H33A H 0.1710 0.3293 0.3617 0.241 Uiso 1 calc R . . H33B H 0.1282 0.5065 0.3735 0.241 Uiso 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 S1 0.118(2) 0.0569(15) 0.0870(18) -0.0132(13) -0.0044(14) 0.0010(15) Cl1 0.136(3) 0.147(3) 0.113(2) -0.008(2) -0.0100(19) 0.005(2) Cl2 0.219(4) 0.189(4) 0.115(3) 0.027(2) -0.022(3) -0.078(3) P1 0.082(2) 0.0525(15) 0.0513(15) -0.0087(13) 0.0059(13) -0.0037(15) O1 0.079(9) 0.088(6) 0.051(6) -0.012(5) -0.001(6) -0.002(6) N1 0.081(7) 0.050(4) 0.046(5) 0.006(4) 0.000(5) -0.002(5) N2 0.092(8) 0.049(4) 0.054(5) 0.002(4) 0.005(6) -0.012(5) N3 0.068(9) 0.074(5) 0.074(6) -0.006(5) 0.015(6) 0.004(5) N4 0.075(9) 0.081(5) 0.074(6) -0.003(4) 0.015(6) 0.005(5) C1 0.093(11) 0.048(6) 0.057(8) -0.002(6) 0.010(9) -0.011(7) C2 0.082(10) 0.033(5) 0.057(7) 0.001(5) 0.021(7) -0.012(5) C3 0.086(10) 0.043(6) 0.054(6) 0.006(4) 0.008(7) -0.004(6) C4 0.079(11) 0.053(6) 0.063(8) -0.003(5) 0.017(8) -0.001(6) C5 0.110(11) 0.066(7) 0.063(8) -0.002(6) 0.018(8) 0.001(7) C6 0.105(11) 0.063(7) 0.044(6) -0.003(5) 0.015(8) -0.010(8) C7 0.084(10) 0.051(6) 0.047(7) 0.002(6) 0.009(7) -0.006(6) C8 0.101(10) 0.051(6) 0.055(7) -0.005(5) -0.008(8) -0.009(7) C9 0.087(10) 0.079(8) 0.079(8) 0.006(6) -0.006(7) -0.001(7) C10 0.095(10) 0.052(6) 0.073(8) 0.016(6) 0.008(8) 0.006(6) C11 0.119(11) 0.069(7) 0.047(6) 0.010(5) 0.010(8) -0.004(7) C12 0.105(11) 0.067(7) 0.052(8) 0.005(5) -0.006(6) 0.005(6) C13 0.110(10) 0.100(8) 0.106(8) 0.003(7) 0.009(7) 0.019(8) C14 0.088(12) 0.060(6) 0.073(9) -0.003(6) 0.014(9) 0.002(6) C15 0.086(11) 0.087(7) 0.070(8) 0.001(6) 0.020(9) -0.002(7) C16 0.091(11) 0.062(6) 0.102(10) -0.024(7) 0.022(8) 0.000(7) C17 0.099(12) 0.066(6) 0.082(9) -0.016(7) 0.005(9) -0.013(7) C18 0.124(13) 0.098(8) 0.063(8) -0.004(6) -0.006(9) -0.004(8) C19 0.113(12) 0.100(7) 0.070(9) -0.007(6) 0.019(7) 0.007(7) C20 0.104(10) 0.105(8) 0.138(9) -0.007(7) -0.028(8) -0.018(8) C21 0.055(7) 0.072(7) 0.044(5) -0.006(5) -0.004(4) -0.015(5) C22 0.098(8) 0.059(6) 0.045(6) 0.003(6) 0.008(5) 0.001(6) C23 0.107(10) 0.084(9) 0.074(8) -0.001(6) -0.019(6) -0.009(7) C24 0.100(10) 0.106(10) 0.065(7) 0.031(7) -0.001(6) 0.012(8) C25 0.106(9) 0.076(7) 0.086(8) 0.003(7) -0.003(7) 0.002(8) C26 0.087(9) 0.066(8) 0.067(7) -0.008(5) 0.005(6) -0.014(6) C27 0.072(8) 0.083(7) 0.039(6) 0.005(5) 0.001(5) -0.013(6) C28 0.088(10) 0.140(9) 0.051(7) -0.009(7) 0.009(6) 0.014(8) C29 0.105(14) 0.230(18) 0.050(8) 0.011(10) 0.012(8) 0.018(12) C30 0.086(12) 0.25(2) 0.059(10) 0.044(11) -0.009(8) -0.021(13) C31 0.123(13) 0.155(12) 0.054(8) 0.033(8) -0.016(7) -0.049(10) C32 0.086(9) 0.117(10) 0.050(6) 0.025(7) 0.006(6) -0.025(7) C33 0.180(14) 0.308(19) 0.113(11) 0.010(12) 0.007(10) -0.106(13) _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 S1 P1 1.969(3) . ? Cl1 C33 1.713(11) . ? Cl2 C33 1.622(11) . ? P1 C27 1.811(9) . ? P1 C21 1.817(8) . ? P1 C3 1.857(9) . ? O1 C1 1.309(12) . ? N1 N2 1.287(7) . ? N1 C2 1.412(9) . ? N2 C7 1.443(10) . ? N3 N4 1.257(8) . ? N3 C4 1.417(10) . ? N4 C14 1.436(11) . ? C1 C6 1.379(11) . ? C1 C2 1.435(12) . ? C2 C3 1.433(11) . ? C3 C4 1.398(11) . ? C4 C5 1.441(12) . ? C5 C6 1.345(11) . ? C7 C12 1.372(11) . ? C7 C8 1.376(10) . ? C8 C9 1.397(11) . ? C9 C10 1.380(11) . ? C10 C11 1.403(11) . ? C10 C13 1.514(11) . ? C11 C12 1.405(11) . ? C14 C19 1.398(12) . ? C14 C15 1.403(11) . ? C15 C16 1.379(11) . ? C16 C17 1.359(12) . ? C17 C18 1.372(12) . ? C17 C20 1.520(12) . ? C18 C19 1.396(12) . ? C21 C22 1.375(9) . ? C21 C26 1.424(10) . ? C22 C23 1.378(10) . ? C23 C24 1.397(11) . ? C24 C25 1.373(11) . ? C25 C26 1.379(10) . ? C27 C28 1.391(11) . ? C27 C32 1.409(11) . ? C28 C29 1.424(14) . ? C29 C30 1.380(16) . ? C30 C31 1.385(16) . ? C31 C32 1.399(12) . ? 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 C27 P1 C21 100.0(4) . . ? C27 P1 C3 107.7(5) . . ? C21 P1 C3 109.9(5) . . ? C27 P1 S1 113.8(4) . . ? C21 P1 S1 112.3(3) . . ? C3 P1 S1 112.4(3) . . ? N2 N1 C2 115.4(9) . . ? N1 N2 C7 116.2(9) . . ? N4 N3 C4 112.7(11) . . ? N3 N4 C14 116.7(11) . . ? O1 C1 C6 119.1(12) . . ? O1 C1 C2 122.7(13) . . ? C6 C1 C2 118.2(12) . . ? N1 C2 C3 116.3(10) . . ? N1 C2 C1 124.4(12) . . ? C3 C2 C1 119.2(11) . . ? C4 C3 C2 120.0(10) . . ? C4 C3 P1 123.4(9) . . ? C2 C3 P1 116.5(9) . . ? C3 C4 N3 119.6(10) . . ? C3 C4 C5 118.4(11) . . ? N3 C4 C5 121.8(12) . . ? C6 C5 C4 120.4(12) . . ? C5 C6 C1 123.4(11) . . ? C12 C7 C8 122.5(10) . . ? C12 C7 N2 122.1(10) . . ? C8 C7 N2 115.4(10) . . ? C7 C8 C9 118.7(9) . . ? C10 C9 C8 121.5(9) . . ? C9 C10 C11 117.8(10) . . ? C9 C10 C13 120.4(11) . . ? C11 C10 C13 121.8(11) . . ? C10 C11 C12 121.7(9) . . ? C7 C12 C11 117.7(9) . . ? C19 C14 C15 117.1(12) . . ? C19 C14 N4 125.7(12) . . ? C15 C14 N4 117.1(12) . . ? C16 C15 C14 119.8(11) . . ? C17 C16 C15 122.9(11) . . ? C16 C17 C18 118.4(11) . . ? C16 C17 C20 121.3(13) . . ? C18 C17 C20 120.2(13) . . ? C17 C18 C19 120.5(11) . . ? C18 C19 C14 121.2(11) . . ? C22 C21 C26 117.2(8) . . ? C22 C21 P1 121.5(7) . . ? C26 C21 P1 121.1(7) . . ? C21 C22 C23 122.4(8) . . ? C22 C23 C24 119.5(9) . . ? C25 C24 C23 119.8(9) . . ? C24 C25 C26 120.4(9) . . ? C25 C26 C21 120.8(8) . . ? C28 C27 C32 118.8(9) . . ? C28 C27 P1 120.4(9) . . ? C32 C27 P1 120.8(9) . . ? C27 C28 C29 120.8(11) . . ? C30 C29 C28 118.1(15) . . ? C29 C30 C31 122.6(16) . . ? C30 C31 C32 118.6(12) . . ? C31 C32 C27 121.0(10) . . ? Cl2 C33 Cl1 120.7(7) . . ? _diffrn_measured_fraction_theta_max 0.825 _diffrn_reflns_theta_full 20.01 _diffrn_measured_fraction_theta_full 0.825 _refine_diff_density_max 0.217 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.048 #===END data_comp5 _database_code_CSD 165168 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 N2 O1' _chemical_formula_sum 'C14 H14 N2 O' _chemical_formula_weight 226.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.809(4) _cell_length_b 18.173(7) _cell_length_c 11.540(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.99(4) _cell_angle_gamma 90.00 _cell_volume 1209.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour 'dark orange' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.634 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8085 _exptl_absorpt_correction_T_max 0.8575 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\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 2194 _diffrn_reflns_av_R_equivalents 0.0706 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.56 _diffrn_reflns_theta_max 65.08 _reflns_number_total 1981 _reflns_number_gt 1296 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 (Nonius, 1984)' _computing_cell_refinement 'CAD4 (Nonius, 1984)' _computing_data_reduction 'XCAD4/WingX (Farrugia, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1998)' _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^)+(0.0793P)^2^+0.1911P] 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 0.0041(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1981 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0750 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1550 _refine_ls_wR_factor_gt 0.1322 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 O1 O 1.1771(3) 0.67173(9) 0.60493(14) 0.0646(5) Uani 1 1 d . . . N1 N 0.5540(3) 0.88438(10) 0.41686(15) 0.0563(5) Uani 1 1 d . . . N2 N 0.5419(3) 0.89808(9) 0.30989(14) 0.0534(5) Uani 1 1 d . . . C1 C 1.0228(4) 0.72414(11) 0.56066(17) 0.0531(6) Uani 1 1 d . . . C2 C 0.8475(4) 0.75056(12) 0.62043(18) 0.0543(6) Uani 1 1 d . . . C3 C 0.6954(4) 0.80442(12) 0.57341(17) 0.0521(6) Uani 1 1 d . . . C4 C 0.7187(4) 0.83075(11) 0.46104(17) 0.0515(5) Uani 1 1 d . . . C5 C 0.8986(4) 0.80467(12) 0.40138(18) 0.0554(6) Uani 1 1 d . . . C6 C 1.0506(4) 0.75252(13) 0.45080(18) 0.0561(6) Uani 1 1 d . . . C7 C 0.3709(4) 0.95263(11) 0.27093(18) 0.0527(6) Uani 1 1 d . . . C8 C 0.3806(5) 0.98123(13) 0.16049(19) 0.0621(6) Uani 1 1 d . . . C9 C 0.2216(4) 1.03400(13) 0.1162(2) 0.0634(6) Uani 1 1 d . . . C10 C 0.0482(4) 1.05815(12) 0.1789(2) 0.0591(6) Uani 1 1 d . . . C11 C 0.0385(4) 1.02793(14) 0.2887(2) 0.0670(7) Uani 1 1 d . . . C12 C 0.1970(4) 0.97643(14) 0.3349(2) 0.0647(7) Uani 1 1 d . . . C19 C 0.5121(5) 0.83422(17) 0.6427(2) 0.0642(7) Uani 1 1 d . . . C20 C -0.1207(6) 1.11634(18) 0.1293(3) 0.0772(8) Uani 1 1 d . . . H1 H 1.137(6) 0.657(2) 0.674(3) 0.126(13) Uiso 1 1 d . . . H2 H 0.830(4) 0.7309(13) 0.699(2) 0.075(7) Uiso 1 1 d . . . H5 H 0.915(4) 0.8223(12) 0.326(2) 0.059(6) Uiso 1 1 d . . . H6 H 1.171(4) 0.7318(12) 0.4070(19) 0.061(6) Uiso 1 1 d . . . H8 H 0.505(4) 0.9630(13) 0.115(2) 0.074(7) Uiso 1 1 d . . . H9 H 0.238(4) 1.0531(13) 0.039(2) 0.070(7) Uiso 1 1 d . . . H11 H -0.076(5) 1.0457(15) 0.338(2) 0.091(9) Uiso 1 1 d . . . H12 H 0.187(5) 0.9578(15) 0.413(2) 0.087(8) Uiso 1 1 d . . . H19A H 0.476(6) 0.807(2) 0.699(3) 0.134(14) Uiso 1 1 d . . . H19B H 0.562(8) 0.879(2) 0.680(4) 0.172(18) Uiso 1 1 d . . . H19C H 0.365(7) 0.845(2) 0.594(3) 0.136(13) Uiso 1 1 d . . . H20A H -0.274(8) 1.102(2) 0.121(4) 0.162(17) Uiso 1 1 d . . . H20B H -0.118(7) 1.156(2) 0.181(3) 0.141(15) Uiso 1 1 d . . . H20C H -0.073(6) 1.1303(18) 0.052(3) 0.109(11) Uiso 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 O1 0.0790(11) 0.0607(10) 0.0524(10) 0.0080(7) 0.0008(8) 0.0046(8) N1 0.0693(12) 0.0533(11) 0.0450(10) 0.0024(8) 0.0021(8) -0.0033(9) N2 0.0674(12) 0.0498(10) 0.0415(9) 0.0020(7) 0.0003(8) -0.0028(8) C1 0.0644(13) 0.0480(12) 0.0440(11) -0.0005(9) -0.0047(9) -0.0088(10) C2 0.0665(14) 0.0573(13) 0.0377(11) 0.0019(10) 0.0014(10) -0.0092(11) C3 0.0641(14) 0.0509(12) 0.0398(11) -0.0018(9) -0.0008(9) -0.0100(10) C4 0.0633(13) 0.0476(11) 0.0416(11) -0.0019(9) -0.0015(9) -0.0058(10) C5 0.0684(14) 0.0596(13) 0.0368(11) 0.0050(10) 0.0008(10) -0.0071(11) C6 0.0630(14) 0.0654(14) 0.0388(11) -0.0025(10) 0.0014(10) -0.0033(11) C7 0.0608(13) 0.0479(11) 0.0482(12) -0.0002(9) 0.0019(10) -0.0012(10) C8 0.0765(16) 0.0640(15) 0.0466(12) 0.0031(10) 0.0100(11) 0.0118(12) C9 0.0765(16) 0.0644(14) 0.0483(13) 0.0080(11) 0.0038(11) 0.0093(12) C10 0.0586(13) 0.0559(13) 0.0610(13) 0.0001(10) -0.0003(11) -0.0027(10) C11 0.0660(15) 0.0690(16) 0.0680(15) 0.0037(12) 0.0161(13) 0.0058(12) C12 0.0745(16) 0.0667(15) 0.0538(13) 0.0101(12) 0.0119(12) 0.0021(12) C19 0.0716(17) 0.0735(16) 0.0478(13) -0.0003(12) 0.0084(12) -0.0025(13) C20 0.0736(19) 0.0713(18) 0.085(2) 0.0084(16) 0.0026(15) 0.0146(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 O1 C1 1.364(3) . ? N1 N2 1.253(2) . ? N1 C4 1.416(3) . ? N2 C7 1.436(3) . ? C1 C2 1.383(3) . ? C1 C6 1.396(3) . ? C2 C3 1.385(3) . ? C3 C4 1.404(3) . ? C3 C19 1.507(3) . ? C4 C5 1.402(3) . ? C5 C6 1.371(3) . ? C7 C8 1.384(3) . ? C7 C12 1.390(3) . ? C8 C9 1.386(3) . ? C9 C10 1.382(3) . ? C10 C11 1.388(3) . ? C10 C20 1.508(4) . ? C11 C12 1.374(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 N2 N1 C4 116.48(19) . . ? N1 N2 C7 113.54(18) . . ? O1 C1 C2 123.1(2) . . ? O1 C1 C6 117.0(2) . . ? C2 C1 C6 119.9(2) . . ? C1 C2 C3 121.6(2) . . ? C2 C3 C4 118.3(2) . . ? C2 C3 C19 120.3(2) . . ? C4 C3 C19 121.4(2) . . ? C5 C4 C3 120.0(2) . . ? C5 C4 N1 124.54(19) . . ? C3 C4 N1 115.5(2) . . ? C6 C5 C4 120.7(2) . . ? C5 C6 C1 119.5(2) . . ? C8 C7 C12 119.1(2) . . ? C8 C7 N2 116.3(2) . . ? C12 C7 N2 124.61(19) . . ? C7 C8 C9 120.0(2) . . ? C10 C9 C8 121.5(2) . . ? C9 C10 C11 117.8(2) . . ? C9 C10 C20 120.4(2) . . ? C11 C10 C20 121.8(3) . . ? C12 C11 C10 121.6(2) . . ? C11 C12 C7 120.1(2) . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 65.08 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.160 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.033 #===END # CIF produced by WinGX routine CIF_UPDATE # Created on 2000-10-30 at 23:19:17 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1 # Request file : c:\wingx\files\archive.dat # CIF files read : u struct data_comp6 _database_code_CSD 165169 _audit_creation_date 2000-10-30T23:19:17-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H20 N4 O1' _chemical_formula_structural 'C21 H20 N4 O1' _chemical_formula_sum 'C21 H20 N4 O' _chemical_formula_weight 344.41 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 18.942(4) _cell_length_b 20.515(3) _cell_length_c 4.6558(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1809.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6.2 _cell_measurement_theta_max 11.4 _cell_measurement_wavelength 1.54178 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour 'dark orange' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.641 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_number 6653 _diffrn_reflns_av_R_equivalents 0.121 _diffrn_reflns_av_unetI/netI 0.1496 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 65.04 _diffrn_reflns_theta_full 65.04 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 3048 _reflns_number_gt 1228 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'AFC6-COLLECT (MSC, 1990)' _computing_cell_refinement 'ADC6-INDEX (MSC, 1990)' _computing_data_reduction 'PROCESS (MSC, 1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0668P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3048 _refine_ls_number_parameters 242 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1883 _refine_ls_R_factor_gt 0.085 _refine_ls_wR_factor_ref 0.2121 _refine_ls_wR_factor_gt 0.1656 _refine_ls_goodness_of_fit_ref 1.07 _refine_ls_restrained_S_all 1.07 _refine_ls_shift/su_max 0.072 _refine_ls_shift/su_mean 0.015 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(12) _refine_diff_density_max 0.197 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.041 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.2063(3) 0.6211(3) 0.8530(14) 0.0656(18) Uani 1 1 d . . . N2 N 0.2562(3) 0.6427(3) 1.0050(14) 0.0671(18) Uani 1 1 d . . . N3 N 0.0231(4) 0.6672(3) 0.1831(12) 0.0640(19) Uani 1 1 d . . . N4 N -0.0192(4) 0.7077(3) 0.0657(16) 0.0706(19) Uani 1 1 d . . . O1 O 0.0310(3) 0.8034(2) 0.3464(15) 0.092(2) Uani 1 1 d . . . C1 C 0.0739(4) 0.7577(3) 0.4648(16) 0.065(2) Uani 1 1 d . . . C2 C 0.0695(4) 0.6913(3) 0.3846(18) 0.062(2) Uani 1 1 d . . . C3 C 0.1150(4) 0.6465(3) 0.5209(15) 0.057(2) Uani 1 1 d . . . C4 C 0.1647(4) 0.6691(4) 0.7177(17) 0.063(2) Uani 1 1 d . . . C5 C 0.1683(4) 0.7366(3) 0.798(2) 0.073(2) Uani 1 1 d . . . H5 H 0.2002 0.7511 0.9355 0.088 Uiso 1 1 calc R . . C6 C 0.1222(5) 0.7798(4) 0.6604(18) 0.076(3) Uani 1 1 d . . . H6 H 0.1244 0.8241 0.7026 0.091 Uiso 1 1 calc R . . C7 C 0.2961(4) 0.5946(4) 1.1393(18) 0.065(2) Uani 1 1 d . . . C8 C 0.3539(5) 0.6153(3) 1.294(2) 0.074(3) Uani 1 1 d . . . H8 H 0.3647 0.6595 1.2959 0.089 Uiso 1 1 calc R . . C9 C 0.3966(4) 0.5727(3) 1.4491(19) 0.077(3) Uani 1 1 d . . . H9 H 0.4345 0.5884 1.5559 0.093 Uiso 1 1 calc R . . C10 C 0.3819(4) 0.5070(4) 1.4413(19) 0.075(2) Uani 1 1 d . . . C11 C 0.3239(5) 0.4865(4) 1.2893(19) 0.074(2) Uani 1 1 d . . . H11 H 0.3118 0.4426 1.2926 0.088 Uiso 1 1 calc R . . C12 C 0.2828(5) 0.5293(4) 1.1314(18) 0.078(3) Uani 1 1 d . . . H12 H 0.246 0.5134 1.0194 0.094 Uiso 1 1 calc R . . C13 C -0.0679(4) 0.6819(3) -0.1341(18) 0.062(2) Uani 1 1 d . . . C14 C -0.1143(4) 0.7271(3) -0.2621(15) 0.061(2) Uani 1 1 d . . . H14 H -0.1115 0.7711 -0.2153 0.073 Uiso 1 1 calc R . . C15 C -0.1641(4) 0.7056(4) -0.4577(18) 0.066(2) Uani 1 1 d . . . H15 H -0.1964 0.7355 -0.531 0.08 Uiso 1 1 calc R . . C16 C -0.1680(5) 0.6425(4) -0.5475(17) 0.070(2) Uani 1 1 d . . . C17 C -0.1210(4) 0.6000(4) -0.4261(17) 0.071(2) Uani 1 1 d . . . H17 H -0.1232 0.5565 -0.4822 0.085 Uiso 1 1 calc R . . C18 C -0.0700(4) 0.6172(3) -0.2241(18) 0.069(2) Uani 1 1 d . . . H18 H -0.0385 0.5866 -0.1519 0.083 Uiso 1 1 calc R . . C19 C 0.1084(4) 0.5749(3) 0.4506(17) 0.068(2) Uani 1 1 d . . . H19A H 0.1338 0.5656 0.2771 0.102 Uiso 1 1 calc R . . H19B H 0.0595 0.564 0.4249 0.102 Uiso 1 1 calc R . . H19C H 0.1276 0.5495 0.6053 0.102 Uiso 1 1 calc R . . C20 C 0.4260(5) 0.4574(4) 1.606(2) 0.106(3) Uani 1 1 d . . . H20A H 0.4292 0.4703 1.8037 0.159 Uiso 1 1 calc R . . H20B H 0.4725 0.4554 1.5244 0.159 Uiso 1 1 calc R . . H20C H 0.4041 0.4153 1.5936 0.159 Uiso 1 1 calc R . . C21 C -0.2233(5) 0.6204(4) -0.7554(18) 0.088(3) Uani 1 1 d . . . H21A H -0.2692 0.6311 -0.6818 0.131 Uiso 1 1 calc R . . H21B H -0.2198 0.574 -0.7811 0.131 Uiso 1 1 calc R . . H21C H -0.2163 0.6418 -0.9365 0.131 Uiso 1 1 calc R . . H1 H -0.002(4) 0.774(4) 0.174(18) 0.10(3) Uiso 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 0.057(4) 0.077(4) 0.063(4) -0.002(3) -0.020(4) 0.004(3) N2 0.069(5) 0.062(3) 0.069(5) 0.002(3) -0.009(4) 0.010(3) N3 0.071(5) 0.071(4) 0.050(5) -0.004(3) 0.004(4) -0.002(4) N4 0.073(5) 0.069(4) 0.070(5) 0.005(3) 0.000(4) 0.000(4) O1 0.104(5) 0.059(3) 0.111(5) 0.009(4) -0.011(5) 0.000(3) C1 0.061(5) 0.065(5) 0.068(6) -0.004(4) -0.008(5) 0.004(4) C2 0.076(6) 0.055(4) 0.056(5) -0.004(4) 0.003(5) -0.013(4) C3 0.057(5) 0.049(4) 0.065(5) -0.010(3) -0.022(4) -0.006(3) C4 0.059(5) 0.068(5) 0.062(6) 0.004(4) 0.021(5) -0.006(4) C5 0.079(6) 0.059(5) 0.082(6) -0.009(5) 0.021(6) 0.014(4) C6 0.084(7) 0.060(5) 0.084(7) 0.003(4) 0.010(6) -0.011(4) C7 0.063(6) 0.054(4) 0.078(6) -0.014(4) 0.009(5) -0.009(4) C8 0.086(7) 0.059(4) 0.077(6) 0.004(4) 0.002(6) 0.007(4) C9 0.071(6) 0.065(5) 0.097(7) -0.010(4) -0.025(6) 0.011(4) C10 0.061(5) 0.078(5) 0.086(7) 0.002(5) -0.006(5) -0.009(4) C11 0.078(6) 0.064(4) 0.079(7) 0.001(5) 0.008(6) -0.009(4) C12 0.095(7) 0.076(5) 0.064(6) -0.002(4) -0.005(6) -0.011(5) C13 0.065(5) 0.062(4) 0.060(5) 0.000(4) 0.014(5) -0.005(4) C14 0.080(6) 0.054(4) 0.049(5) 0.008(3) 0.006(5) 0.004(4) C15 0.068(6) 0.077(5) 0.054(5) -0.001(4) -0.027(5) 0.009(4) C16 0.075(6) 0.080(5) 0.056(5) 0.009(4) 0.007(5) -0.006(5) C17 0.075(6) 0.078(5) 0.060(5) -0.012(4) -0.027(5) -0.025(5) C18 0.071(6) 0.060(4) 0.077(6) 0.024(4) 0.016(5) 0.003(4) C19 0.072(6) 0.053(4) 0.078(6) -0.015(4) -0.029(5) -0.007(3) C20 0.122(10) 0.094(6) 0.102(8) 0.015(6) -0.008(7) 0.014(6) C21 0.081(7) 0.113(7) 0.068(6) 0.009(5) -0.007(6) -0.023(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N2 1.261(7) . ? N1 C4 1.409(9) . ? N2 C7 1.392(10) . ? N3 N4 1.276(8) . ? N3 C2 1.377(9) . ? N4 C13 1.412(9) . ? O1 C1 1.358(8) . ? C1 C6 1.368(10) . ? C1 C2 1.415(9) . ? C2 C3 1.411(10) . ? C3 C4 1.392(9) . ? C3 C19 1.512(8) . ? C4 C5 1.437(9) . ? C5 C6 1.399(11) . ? C7 C12 1.363(9) . ? C7 C8 1.377(11) . ? C8 C9 1.391(11) . ? C9 C10 1.378(9) . ? C10 C11 1.372(10) . ? C10 C20 1.523(11) . ? C11 C12 1.384(11) . ? C13 C18 1.392(9) . ? C13 C14 1.410(10) . ? C14 C15 1.384(10) . ? C15 C16 1.363(10) . ? C16 C17 1.369(11) . ? C16 C21 1.496(11) . ? C17 C18 1.394(10) . ? 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 N2 N1 C4 115.1(6) . . ? N1 N2 C7 114.2(6) . . ? N4 N3 C2 117.3(6) . . ? N3 N4 C13 116.7(6) . . ? O1 C1 C6 116.2(7) . . ? O1 C1 C2 121.5(8) . . ? C6 C1 C2 122.3(7) . . ? N3 C2 C3 117.6(6) . . ? N3 C2 C1 124.3(7) . . ? C3 C2 C1 118.1(7) . . ? C4 C3 C2 119.6(6) . . ? C4 C3 C19 121.4(6) . . ? C2 C3 C19 119.0(6) . . ? C3 C4 N1 116.1(7) . . ? C3 C4 C5 121.6(8) . . ? N1 C4 C5 122.1(8) . . ? C6 C5 C4 117.6(9) . . ? C1 C6 C5 120.8(8) . . ? C12 C7 C8 117.6(8) . . ? C12 C7 N2 125.7(8) . . ? C8 C7 N2 116.7(7) . . ? C7 C8 C9 122.7(8) . . ? C10 C9 C8 118.8(8) . . ? C11 C10 C9 118.3(8) . . ? C11 C10 C20 119.7(7) . . ? C9 C10 C20 121.9(8) . . ? C10 C11 C12 122.0(8) . . ? C7 C12 C11 120.3(9) . . ? C18 C13 C14 118.7(8) . . ? C18 C13 N4 125.0(7) . . ? C14 C13 N4 116.1(6) . . ? C15 C14 C13 119.6(7) . . ? C16 C15 C14 122.8(8) . . ? C15 C16 C17 116.3(8) . . ? C15 C16 C21 121.6(8) . . ? C17 C16 C21 122.0(7) . . ? C16 C17 C18 124.6(7) . . ? C13 C18 C17 117.8(8) . . ?