# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_name 'Prof Binne Zwanenburg' _publ_contact_author_address ; Department of Organic Chemistry NSR Center for Molecular Structure, Design & Synthesis University of Nymegen Toernooiveld 1 Nymegen 6525 ED NETHERLANDS ; _publ_contact_author_phone '031 024 3653159' _publ_contact_author_fax '031 024 3553450' _publ_contact_author_email zwanenb@sci.kun.nl _publ_requested_coeditor_name ? _publ_contact_letter ; ? ; #============================================================================== # 3. AUTHOR LIST loop_ _publ_author_name _publ_author_address 'A. Reizelman' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'C. del-Bianco' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'S.C.M. Wigchert' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'B. Zwanenburg' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; #============================================================================== # 4. TEXT _publ_section_title ; Synthesis and Bioactivity of Labelled Germination Stimulants for the Isolation and Identification of the Strigolactone Receptor ; _publ_section_abstract ; ; _publ_section_references ; CAD4 EXPRESS Enraf-Nonius diffractometer control software (1994). Release 5.1, Enraf-Nonius Delft, The Netherlands. Gelder, R. de, Graaff, R. A. G. de & Schenk, H. (1993). Acta Cryst. A49, 287--293. Grant, D. F. & Gabe, E. J. (1978). J. Appl. Cryst. 11, 114--120. International Tables for X-ray Crystallography (1974). Vol. IV, Birmingham, England: Kynoch Press. Lehman, M. S. & Larsen, F. K. (1974). Acta Cryst. A30, 580--584. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351--359. Sheldrick, G. M. (1997). SHELXL-97, Program for the refinement of crystal structures. University of Gottingen, Germany. Smits, J. M. M., Behm, H., Bosman, W. P. & Beurskens, P. T. (1988). J. Crystallogr. Spectrosc. Res. 18, 447--450. Spek, A. L. (1990). Acta Cryst. A46, C-34. Spek, A. L. (1993). PLUTON, A program for plotting molecular and crystal structures. University of Utrecht, The Netherlands. Spek, A. L. (1995). PLATON-93, Program for display and analysis of crystal and molecular structures. University of Utrecht, The Netherlands. ; #============================================================================== data_WIG1 _database_code_CSD 197746 _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 2002-11-14 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H23 N O7' _chemical_formula_weight 413.41 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 9.3201(4) _cell_length_b 12.5782(4) _cell_length_c 17.9679(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2106.38(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 22.177 _cell_measurement_theta_max 45.115 _exptl_crystal_description 'regular rod' _exptl_crystal_colour 'transparent colourless' _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.815 _exptl_absorpt_correction_type experimental #_exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.960 _exptl_absorpt_correction_T_max 1.055 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius CAD4' _diffrn_measurement_method \w/2\q-scan _diffrn_special_details ; \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.44 + 0.19tan\q)\%, range: 0.69\%-1.43\%, aperture (1.33 + 0.13tan\q)mm., range: 1.34-1.69mm. Maximum scan time: 20 sec/reflection. ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_time 7200 _diffrn_standards_decay_% 3.701 _diffrn_reflns_number 2282 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.29 _diffrn_reflns_theta_max 69.94 _reflns_number_total 2282 _reflns_number_gt 1967 _reflns_number_observed 1967 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; CAD4 EXPRESS (Enraf-Nonius, 1994) ; #_computing_cell_refinement #; #CAD4 EXPRESS (Enraf-Nonius, 1994) #; _computing_data_reduction ; local programs (Smits et al., 1988), profile analysis (Lehman & Larsen, 1974, Grant & Gabe, 1978), EMPABS (North et al., 1968) ; _computing_structure_solution ; CRUNCH (de Gelder et al., 1993), ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLUTON (Spek, 1993), PLATON (Spek, 1990, 1995) ; _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 ; w=1/[\s^2^(Fo^2^)+(0.0776P)^2^+0.1405P] 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 0.0023(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_Flack 0.4(3) _refine_ls_number_reflns 2282 _refine_ls_number_parameters 364 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0397 _refine_ls_R_factor_obs 0.0397 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_all 0.1169 _refine_ls_wR_factor_gt 0.1094 _refine_ls_wR_factor_obs 0.1094 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_goodness_of_fit_all 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_shift/esd_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 C1 C 0.4994(3) 0.1924(2) 0.80460(14) 0.0441(6) Uani 1 d . . . C2 C 0.4224(3) 0.2609(2) 0.76006(15) 0.0430(6) Uani 1 d . . . H2 H 0.364(4) 0.316(3) 0.7823(19) 0.049(8) Uiso 1 d . . . C3 C 0.4289(3) 0.2460(2) 0.68329(14) 0.0394(6) Uani 1 d . . . C4 C 0.3519(3) 0.3082(2) 0.62430(15) 0.0431(6) Uani 1 d . . . H4 H 0.263(4) 0.326(3) 0.637(2) 0.063(11) Uiso 1 d . . . O5 O 0.4273(3) 0.40899(15) 0.60926(10) 0.0531(6) Uani 1 d . . . C6 C 0.4492(4) 0.4226(2) 0.53545(17) 0.0497(7) Uani 1 d . . . C7 C 0.4054(3) 0.3258(2) 0.49635(15) 0.0428(6) Uani 1 d . . . C8 C 0.3705(3) 0.2424(2) 0.55195(14) 0.0433(6) Uani 1 d . . . H8 H 0.278(4) 0.201(3) 0.539(2) 0.064(10) Uiso 1 d . . . C9 C 0.4924(4) 0.1624(2) 0.56849(16) 0.0517(7) Uani 1 d . . . H9A H 0.580(4) 0.185(3) 0.545(2) 0.061(10) Uiso 1 d . . . H9B H 0.477(4) 0.091(3) 0.548(2) 0.069(11) Uiso 1 d . . . C10 C 0.5077(3) 0.16447(19) 0.65186(14) 0.0410(6) Uani 1 d . . . C11 C 0.5859(3) 0.0962(2) 0.69676(17) 0.0468(6) Uani 1 d . . . H11 H 0.640(3) 0.037(3) 0.6740(17) 0.044(8) Uiso 1 d . . . C12 C 0.5808(4) 0.1106(2) 0.77315(16) 0.0473(7) Uani 1 d . . . H12 H 0.638(3) 0.066(3) 0.8023(19) 0.051(9) Uiso 1 d . . . O13 O 0.4990(4) 0.50374(16) 0.51155(13) 0.0721(7) Uani 1 d . . . C14 C 0.4021(4) 0.3203(2) 0.42242(17) 0.0482(7) Uani 1 d . . . H14 H 0.433(4) 0.376(3) 0.3937(17) 0.047(9) Uiso 1 d . . . O15 O 0.3570(3) 0.22960(17) 0.38846(10) 0.0561(6) Uani 1 d . . . C16 C 0.3803(3) 0.2240(3) 0.31090(15) 0.0486(7) Uani 1 d . . . H16 H 0.392(4) 0.296(3) 0.2880(19) 0.061(10) Uiso 1 d . . . C17 C 0.2822(4) 0.1470(3) 0.27595(17) 0.0534(7) Uani 1 d . . . H17 H 0.181(5) 0.152(3) 0.280(2) 0.079(13) Uiso 1 d . . . C18 C 0.3539(3) 0.0714(3) 0.24173(17) 0.0505(7) Uani 1 d . . . C19 C 0.5072(4) 0.0907(3) 0.25659(17) 0.0516(7) Uani 1 d . . . O20 O 0.5198(2) 0.18245(18) 0.29710(12) 0.0555(6) Uani 1 d . . . C21 C 0.3062(6) -0.0186(4) 0.1949(3) 0.0834(13) Uani 1 d . . . H21A H 0.349(6) -0.003(5) 0.139(3) 0.13(2) Uiso 1 d . . . H21B H 0.368(5) -0.081(4) 0.214(3) 0.097(15) Uiso 1 d . . . H21C H 0.198(6) -0.022(4) 0.188(3) 0.094(14) Uiso 1 d . . . O22 O 0.6095(3) 0.0404(2) 0.23849(18) 0.0847(9) Uani 1 d . . . N23 N 0.4961(4) 0.19957(19) 0.88362(13) 0.0519(6) Uani 1 d . . . H23 H 0.500(4) 0.145(2) 0.9081(15) 0.036(7) Uiso 1 d . . . C24 C 0.4979(4) 0.2915(2) 0.92289(15) 0.0508(7) Uani 1 d . . . O25 O 0.4977(4) 0.37932(17) 0.89671(11) 0.0710(7) Uani 1 d . . . O26 O 0.4977(4) 0.26743(16) 0.99543(11) 0.0675(7) Uani 1 d . . . C27 C 0.5069(6) 0.3501(3) 1.05221(16) 0.0707(11) Uani 1 d . . . C28 C 0.3747(7) 0.4202(5) 1.0477(4) 0.0909(15) Uani 1 d . . . H28A H 0.387(6) 0.469(5) 0.999(3) 0.111(18) Uiso 1 d . . . H28B H 0.293(8) 0.385(6) 1.048(4) 0.16(3) Uiso 1 d . . . H28C H 0.375(5) 0.477(4) 1.085(3) 0.089(14) Uiso 1 d . . . C29 C 0.6433(6) 0.4121(5) 1.0451(3) 0.0900(14) Uani 1 d . . . H29A H 0.726(7) 0.368(5) 1.046(4) 0.12(2) Uiso 1 d . . . H29B H 0.639(6) 0.445(4) 0.997(3) 0.103(17) Uiso 1 d . . . H29C H 0.675(7) 0.457(6) 1.094(4) 0.14(2) Uiso 1 d . . . C30 C 0.5071(14) 0.2851(5) 1.1234(2) 0.142(4) Uani 1 d . . . H30A H 0.389(6) 0.247(5) 1.125(3) 0.12(2) Uiso 1 d . . . H30B H 0.556(7) 0.221(5) 1.116(3) 0.13(2) Uiso 1 d . . . H30C H 0.508(6) 0.332(4) 1.173(3) 0.120(17) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0546(16) 0.0397(12) 0.0382(12) 0.0045(10) -0.0004(14) -0.0066(14) C2 0.0502(15) 0.0409(13) 0.0379(13) -0.0003(11) 0.0040(12) -0.0001(13) C3 0.0416(13) 0.0386(12) 0.0379(13) -0.0009(11) 0.0006(11) -0.0009(12) C4 0.0477(16) 0.0446(15) 0.0369(13) -0.0008(12) 0.0014(11) 0.0041(13) O5 0.0829(15) 0.0382(10) 0.0383(9) -0.0056(8) -0.0042(10) 0.0050(11) C6 0.0652(19) 0.0425(14) 0.0413(14) -0.0023(12) -0.0017(14) 0.0009(14) C7 0.0477(15) 0.0427(13) 0.0381(13) -0.0046(11) -0.0006(12) 0.0004(13) C8 0.0486(16) 0.0446(14) 0.0366(13) -0.0047(12) -0.0016(11) -0.0041(13) C9 0.069(2) 0.0443(15) 0.0418(14) -0.0066(12) 0.0001(16) 0.0098(16) C10 0.0463(14) 0.0346(12) 0.0420(13) -0.0018(10) 0.0021(12) -0.0034(12) C11 0.0531(16) 0.0342(12) 0.0530(15) 0.0008(12) 0.0012(14) 0.0046(13) C12 0.0557(17) 0.0388(14) 0.0475(15) 0.0048(12) -0.0038(14) 0.0020(13) O13 0.116(2) 0.0451(11) 0.0551(12) 0.0009(10) 0.0031(15) -0.0179(15) C14 0.0619(18) 0.0427(14) 0.0400(14) -0.0022(12) -0.0004(14) -0.0031(14) O15 0.0835(16) 0.0513(11) 0.0334(9) -0.0047(9) -0.0003(10) -0.0088(12) C16 0.0586(18) 0.0535(16) 0.0339(13) -0.0040(12) -0.0034(12) 0.0024(14) C17 0.0480(17) 0.0653(19) 0.0470(16) -0.0078(15) -0.0074(14) 0.0061(15) C18 0.0488(16) 0.0538(16) 0.0489(16) -0.0045(13) -0.0028(13) -0.0003(14) C19 0.0449(15) 0.0581(16) 0.0518(15) 0.0015(14) 0.0008(14) 0.0074(15) O20 0.0469(12) 0.0665(13) 0.0532(11) -0.0048(10) -0.0068(10) -0.0054(11) C21 0.078(3) 0.074(3) 0.098(3) -0.035(3) -0.008(3) -0.009(2) O22 0.0577(15) 0.094(2) 0.102(2) -0.0097(18) 0.0049(15) 0.0248(15) N23 0.0800(18) 0.0391(12) 0.0366(11) 0.0098(10) -0.0006(14) 0.0027(14) C24 0.0707(19) 0.0453(14) 0.0365(12) 0.0088(11) -0.0020(15) 0.0003(17) O25 0.126(2) 0.0443(11) 0.0429(10) 0.0088(9) -0.0062(15) -0.0029(15) O26 0.121(2) 0.0456(11) 0.0361(9) 0.0058(9) -0.0013(13) -0.0017(15) C27 0.120(3) 0.0556(17) 0.0362(14) 0.0040(13) 0.006(2) 0.001(2) C28 0.095(4) 0.077(3) 0.100(4) -0.009(3) 0.036(3) 0.001(3) C29 0.098(3) 0.091(3) 0.081(3) -0.001(3) -0.029(3) 0.000(3) C30 0.294(12) 0.092(4) 0.0387(19) 0.007(2) -0.001(4) -0.006(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.378(4) . Y C1 C12 1.397(4) . Y C1 N23 1.423(3) . Y C2 C3 1.393(4) . Y C2 H2 0.97(3) . Y C3 C10 1.382(4) . Y C3 C4 1.501(4) . Y C4 O5 1.474(4) . Y C4 C8 1.551(4) . Y C4 H4 0.89(4) . Y O5 C6 1.353(3) . Y C6 O13 1.201(4) . Y C6 C7 1.464(4) . Y C7 C14 1.330(4) . Y C7 C8 1.485(4) . Y C8 C9 1.547(5) . Y C8 H8 1.03(4) . Y C9 C10 1.505(4) . Y C9 H9A 0.96(4) . Y C9 H9B 0.98(4) . Y C10 C11 1.386(4) . Y C11 C12 1.385(4) . Y C11 H11 0.99(3) . Y C12 H12 0.93(3) . Y C14 O15 1.360(4) . Y C14 H14 0.92(3) . Y O15 C16 1.412(3) . Y C16 O20 1.423(4) . Y C16 C17 1.473(5) . Y C16 H16 1.01(4) . Y C17 C18 1.315(5) . Y C17 H17 0.95(4) . Y C18 C19 1.474(5) . Y C18 C21 1.478(5) . Y C19 O22 1.190(4) . Y C19 O20 1.369(4) . Y C21 H21A 1.09(6) . Y C21 H21B 1.03(5) . Y C21 H21C 1.02(5) . Y N23 C24 1.355(4) . Y N23 H23 0.81(3) . Y C24 O25 1.201(3) . Y C24 O26 1.338(3) . Y O26 C27 1.459(4) . Y C27 C29 1.497(7) . Y C27 C28 1.517(7) . Y C27 C30 1.518(5) . Y C28 H28A 1.07(6) . Y C28 H28B 0.88(7) . Y C28 H28C 0.98(5) . Y C29 H29A 0.95(6) . Y C29 H29B 0.96(5) . Y C29 H29C 1.09(7) . Y C30 H30A 1.20(6) . Y C30 H30B 0.93(6) . Y C30 H30C 1.07(5) . Y loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C12 120.5(2) . . Y C2 C1 N23 121.9(3) . . Y C12 C1 N23 117.5(3) . . Y C1 C2 C3 117.9(3) . . Y C1 C2 H2 120(2) . . Y C3 C2 H2 122(2) . . Y C10 C3 C2 121.8(3) . . Y C10 C3 C4 110.6(2) . . Y C2 C3 C4 127.5(3) . . Y O5 C4 C3 110.5(2) . . Y O5 C4 C8 104.6(2) . . Y C3 C4 C8 105.1(2) . . Y O5 C4 H4 106(2) . . Y C3 C4 H4 113(2) . . Y C8 C4 H4 117(2) . . Y C6 O5 C4 111.1(2) . . Y O13 C6 O5 121.1(3) . . Y O13 C6 C7 130.0(3) . . Y O5 C6 C7 108.9(2) . . Y C14 C7 C6 121.9(3) . . Y C14 C7 C8 129.1(3) . . Y C6 C7 C8 109.0(2) . . Y C7 C8 C9 115.3(3) . . Y C7 C8 C4 102.2(2) . . Y C9 C8 C4 105.6(2) . . Y C7 C8 H8 113(2) . . Y C9 C8 H8 109(2) . . Y C4 C8 H8 111(2) . . Y C10 C9 C8 104.4(2) . . Y C10 C9 H9A 111(2) . . Y C8 C9 H9A 110(2) . . Y C10 C9 H9B 114(2) . . Y C8 C9 H9B 115(2) . . Y H9A C9 H9B 104(3) . . Y C3 C10 C11 120.1(3) . . Y C3 C10 C9 111.7(2) . . Y C11 C10 C9 128.2(3) . . Y C12 C11 C10 118.5(3) . . Y C12 C11 H11 121.8(18) . . Y C10 C11 H11 119.6(18) . . Y C11 C12 C1 121.0(3) . . Y C11 C12 H12 117(2) . . Y C1 C12 H12 122(2) . . Y C7 C14 O15 119.9(3) . . Y C7 C14 H14 121(2) . . Y O15 C14 H14 119.0(19) . . Y C14 O15 C16 115.9(2) . . Y O15 C16 O20 109.3(2) . . Y O15 C16 C17 111.0(3) . . Y O20 C16 C17 104.6(2) . . Y O15 C16 H16 112(2) . . Y O20 C16 H16 99(2) . . Y C17 C16 H16 119(2) . . Y C18 C17 C16 111.1(3) . . Y C18 C17 H17 126(3) . . Y C16 C17 H17 123(3) . . Y C17 C18 C19 106.7(3) . . Y C17 C18 C21 131.9(4) . . Y C19 C18 C21 121.4(3) . . Y O22 C19 O20 121.7(3) . . Y O22 C19 C18 129.7(3) . . Y O20 C19 C18 108.6(3) . . Y C19 O20 C16 108.9(2) . . Y C18 C21 H21A 106(3) . . Y C18 C21 H21B 103(3) . . Y H21A C21 H21B 103(4) . . Y C18 C21 H21C 113(3) . . Y H21A C21 H21C 105(4) . . Y H21B C21 H21C 124(4) . . Y C24 N23 C1 125.0(2) . . Y C24 N23 H23 115.7(19) . . Y C1 N23 H23 119.1(19) . . Y O25 C24 O26 126.2(3) . . Y O25 C24 N23 125.5(2) . . Y O26 C24 N23 108.3(2) . . Y C24 O26 C27 121.3(2) . . Y O26 C27 C29 111.2(4) . . Y O26 C27 C28 109.2(4) . . Y C29 C27 C28 112.5(4) . . Y O26 C27 C30 101.9(3) . . Y C29 C27 C30 110.6(6) . . Y C28 C27 C30 111.0(6) . . Y C27 C28 H28A 107(3) . . Y C27 C28 H28B 114(5) . . Y H28A C28 H28B 113(6) . . Y C27 C28 H28C 113(3) . . Y H28A C28 H28C 98(4) . . Y H28B C28 H28C 111(5) . . Y C27 C29 H29A 113(4) . . Y C27 C29 H29B 105(3) . . Y H29A C29 H29B 107(5) . . Y C27 C29 H29C 116(3) . . Y H29A C29 H29C 94(4) . . Y H29B C29 H29C 121(4) . . Y C27 C30 H30A 103(3) . . Y C27 C30 H30B 111(4) . . Y H30A C30 H30B 96(5) . . Y C27 C30 H30C 114(3) . . Y H30A C30 H30C 102(4) . . Y H30B C30 H30C 126(5) . . Y _diffrn_reflns_theta_full 69.94 _refine_diff_density_max 0.192 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.041 _publ_section_experimental ; Crystal colour: transparent colourless, crystal shape: regular rod. Profile analysis combining the methods of Lehman & Larsen (1974) and Grant & Gabe (1978). Empirical absorption correction using EMPABS (North, Phillips & Mathews, 1968). Data collection parameters: \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.44 + 0.19tan\q)\%, range: 0.69\%-1.43\%, aperture (1.33 + 0.13tan\q)mm., range: 1.34-1.69mm. Maximum scan time: 20 sec/reflection. Least-squares refinement using calculated weights: w=1/[\s^2^(Fo^2^)+(0.0776P)^2^+0.1405P] where P=(Fo^2^+2Fc^2^)/3 ;