Supplementary Material (ESI) for Photochemical & Photobiological Sciences This journal is © The Royal Society of Chemistry and Owner Societies 2006 data_global _journal_coden_Cambridge 171 _publ_contact_author_name 'J. N. Moorthy' _publ_contact_author_address ;Department of Chemistry Indian Institute of Technology Kanpur 208 016 INDIA ; _publ_contact_author_email moorthy@iitk.ac.in _publ_contact_author_phone '091 512 259 7438' loop_ _publ_author_name _publ_author_address 'Jarugu Narasimha Moorthy' ;Department of Chemistry Indian Institute of Technology Kanpur 208 016 INDIA ; 'Venkat, P' ;Department of Chemistry Indian Institute of Technology Kanpur 208 016 INDIA ; 'Savitha, G' ;Department of Chemistry Indian Institute of Technology Kanpur 208 016 INDIA ; 'Richard Weiss' ; ? ; _publ_requested_journal 'Photochemical & Photobiological Sciences' _publ_section_title ; Cis->trans and trans->cis isomerizations of styrylcoumarins in the solid state. Importance of the location of free volume in crystal lattices ; data_4s6slt _database_code_depnum_ccdc_archive 'CCDC 611803' _audit_creation_method SHELXL-97 _chemical_name_systematic 4-methyl-6-styrylcoumarin _chemical_name_common ? _chemical_melting_point 79-81C _chemical_formula_moiety 'C18 H14 O2' _chemical_formula_sum 'C18 H14 O2' _chemical_formula_weight 262.29 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.879(3) _cell_length_b 8.223(3) _cell_length_c 24.064(8) _cell_angle_alpha 86.989(5) _cell_angle_beta 84.838(6) _cell_angle_gamma 61.519(5) _cell_volume 1364.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 165 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker Nonius Ceramic tube' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9190 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 28.34 _reflns_number_total 6504 _reflns_number_gt 3934 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0606P)^2^+0.0552P] 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 6504 _refine_ls_number_parameters 363 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0968 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1439 _refine_ls_wR_factor_gt 0.1257 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 O1 O 0.32972(17) 0.25185(15) 1.00952(5) 0.0553(3) Uani 1 1 d . . . C3 C 0.1963(2) 0.4595(2) 0.93190(7) 0.0443(4) Uani 1 1 d . . . C4 C 0.2665(2) 0.2848(2) 0.95643(7) 0.0444(4) Uani 1 1 d . . . C5 C 0.1417(2) 0.4778(2) 0.87725(7) 0.0501(4) Uani 1 1 d . . . H5 H 0.0971 0.5926 0.8595 0.060 Uiso 1 1 calc R . . C8 C 0.2813(2) 0.1357(2) 0.92877(7) 0.0509(4) Uani 1 1 d . . . H8 H 0.3303 0.0198 0.9459 0.061 Uiso 1 1 calc R . . O10 O 0.3927(2) 0.34536(19) 1.08534(5) 0.0782(4) Uani 1 1 d . . . C11 C 0.2486(3) 0.5706(2) 1.01516(8) 0.0563(5) Uani 1 1 d . . . H11 H 0.2408 0.6669 1.0357 0.068 Uiso 1 1 calc R . . C12 C 0.2230(3) 0.1603(2) 0.87552(7) 0.0525(4) Uani 1 1 d . . . H12 H 0.2314 0.0599 0.8570 0.063 Uiso 1 1 calc R . . C14 C 0.1855(2) 0.6086(2) 0.96387(7) 0.0497(4) Uani 1 1 d . . . C15 C 0.1514(3) 0.3319(2) 0.84845(7) 0.0514(4) Uani 1 1 d . . . C17 C 0.3275(3) 0.3893(3) 1.04027(8) 0.0553(5) Uani 1 1 d . . . C21 C -0.0796(3) 0.1752(2) 0.78826(7) 0.0524(4) Uani 1 1 d . . . C23 C 0.1027(3) 0.3559(3) 0.78981(7) 0.0644(5) Uani 1 1 d . . . H23 H 0.1389 0.4328 0.7681 0.077 Uiso 1 1 calc R . . C26 C -0.1922(3) 0.2251(3) 0.83835(7) 0.0551(5) Uani 1 1 d . . . H26 H -0.2046 0.3257 0.8576 0.066 Uiso 1 1 calc R . . C28 C -0.0661(3) 0.0254(3) 0.76042(8) 0.0654(5) Uani 1 1 d . . . H28 H 0.0062 -0.0095 0.7263 0.079 Uiso 1 1 calc R . . C30 C -0.2855(3) 0.1294(3) 0.85998(8) 0.0613(5) Uani 1 1 d . . . H30 H -0.3617 0.1660 0.8934 0.074 Uiso 1 1 calc R . . C34 C 0.1042(3) 0.7992(2) 0.93920(9) 0.0741(6) Uani 1 1 d . . . H34A H 0.1095 0.8813 0.9651 0.111 Uiso 1 1 calc R . . H34B H -0.0279 0.8415 0.9315 0.111 Uiso 1 1 calc R . . H34C H 0.1787 0.7973 0.9052 0.111 Uiso 1 1 calc R . . C37 C 0.0141(3) 0.2826(3) 0.76394(8) 0.0654(5) Uani 1 1 d . . . H37 H 0.0108 0.3016 0.7255 0.079 Uiso 1 1 calc R . . C38 C -0.2669(3) -0.0215(3) 0.83221(9) 0.0655(5) Uani 1 1 d . . . H38 H -0.3280 -0.0884 0.8472 0.079 Uiso 1 1 calc R . . C39 C -0.1579(3) -0.0723(3) 0.78243(9) 0.0702(6) Uani 1 1 d . . . H39 H -0.1459 -0.1733 0.7634 0.084 Uiso 1 1 calc R . . O2 O 1.28289(17) -0.00701(16) 0.45512(5) 0.0570(3) Uani 1 1 d . . . C6 C 0.9846(2) 0.2740(2) 0.47504(7) 0.0445(4) Uani 1 1 d . . . C7 C 0.8299(2) 0.4303(2) 0.45306(7) 0.0493(4) Uani 1 1 d . . . H7 H 0.7346 0.5168 0.4773 0.059 Uiso 1 1 calc R . . C9 C 1.1261(2) 0.1500(2) 0.43755(7) 0.0486(4) Uani 1 1 d . . . C13 C 0.8160(3) 0.4587(2) 0.39612(7) 0.0513(4) Uani 1 1 d . . . C16 C 1.0027(3) 0.2326(2) 0.53425(7) 0.0508(4) Uani 1 1 d . . . O18 O 1.4527(2) -0.18575(19) 0.52235(6) 0.0798(4) Uani 1 1 d . . . C19 C 0.9630(3) 0.3291(3) 0.36046(7) 0.0596(5) Uani 1 1 d . . . H19 H 0.9559 0.3469 0.3221 0.072 Uiso 1 1 calc R . . C20 C 1.1164(3) 0.1772(3) 0.38057(7) 0.0573(5) Uani 1 1 d . . . H20 H 1.2134 0.0928 0.3562 0.069 Uiso 1 1 calc R . . C22 C 1.3089(3) -0.0481(3) 0.51096(8) 0.0578(5) Uani 1 1 d . . . C24 C 0.5532(2) 0.4678(3) 0.30604(7) 0.0549(5) Uani 1 1 d . . . C25 C 0.5669(3) 0.3146(3) 0.33726(8) 0.0606(5) Uani 1 1 d . . . H25 H 0.5793 0.3102 0.3755 0.073 Uiso 1 1 calc R . . C27 C 1.1589(3) 0.0777(3) 0.54958(8) 0.0578(5) Uani 1 1 d . . . H27 H 1.1705 0.0503 0.5875 0.069 Uiso 1 1 calc R . . C29 C 0.6531(3) 0.6238(3) 0.37302(8) 0.0624(5) Uani 1 1 d . . . H29 H 0.6204 0.7371 0.3886 0.075 Uiso 1 1 calc R . . C31 C 0.5495(3) 0.6262(3) 0.33254(8) 0.0622(5) Uani 1 1 d . . . H31 H 0.4637 0.7425 0.3192 0.075 Uiso 1 1 calc R . . C32 C 0.8486(3) 0.3573(3) 0.57615(8) 0.0673(5) Uani 1 1 d . . . H32A H 0.8834 0.3101 0.6131 0.101 Uiso 1 1 calc R . . H32B H 0.7276 0.3623 0.5698 0.101 Uiso 1 1 calc R . . H32C H 0.8360 0.4793 0.5725 0.101 Uiso 1 1 calc R . . C33 C 0.5431(3) 0.1744(4) 0.25648(11) 0.0859(7) Uani 1 1 d . . . H33 H 0.5411 0.0758 0.2398 0.103 Uiso 1 1 calc R . . C35 C 0.5623(3) 0.1701(3) 0.31240(10) 0.0725(6) Uani 1 1 d . . . H35 H 0.5724 0.0688 0.3338 0.087 Uiso 1 1 calc R . . C36 C 0.5307(3) 0.4702(3) 0.24949(8) 0.0721(6) Uani 1 1 d . . . H36 H 0.5180 0.5717 0.2278 0.087 Uiso 1 1 calc R . . C40 C 0.5267(3) 0.3239(4) 0.22489(10) 0.0892(8) Uani 1 1 d . . . H40 H 0.5129 0.3271 0.1868 0.107 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0604(8) 0.0484(7) 0.0548(7) 0.0050(6) -0.0129(6) -0.0231(6) C3 0.0400(9) 0.0425(9) 0.0511(10) 0.0015(8) -0.0013(8) -0.0207(8) C4 0.0379(9) 0.0450(9) 0.0488(9) 0.0014(8) -0.0034(7) -0.0186(8) C5 0.0534(11) 0.0432(9) 0.0559(10) 0.0075(8) -0.0060(8) -0.0253(8) C8 0.0494(10) 0.0390(9) 0.0618(11) 0.0050(8) -0.0064(9) -0.0191(8) O10 0.0963(11) 0.0779(10) 0.0568(8) 0.0018(7) -0.0214(8) -0.0360(9) C11 0.0597(12) 0.0482(10) 0.0613(11) -0.0096(9) -0.0017(9) -0.0255(9) C12 0.0536(11) 0.0478(10) 0.0619(11) -0.0027(9) -0.0048(9) -0.0283(9) C14 0.0465(10) 0.0432(9) 0.0598(11) -0.0026(8) -0.0011(8) -0.0219(8) C15 0.0548(11) 0.0557(11) 0.0514(10) 0.0030(8) -0.0035(8) -0.0328(9) C17 0.0526(11) 0.0576(11) 0.0530(11) -0.0045(9) -0.0027(9) -0.0238(9) C21 0.0520(11) 0.0618(11) 0.0457(10) 0.0007(8) -0.0106(8) -0.0278(9) C23 0.0836(15) 0.0726(13) 0.0527(11) 0.0089(10) -0.0081(10) -0.0501(12) C26 0.0525(11) 0.0606(11) 0.0508(10) -0.0072(9) -0.0076(9) -0.0244(9) C28 0.0579(12) 0.0835(14) 0.0594(12) -0.0220(10) 0.0034(9) -0.0365(11) C30 0.0481(11) 0.0801(14) 0.0536(11) -0.0052(10) -0.0009(9) -0.0287(10) C34 0.0997(17) 0.0444(10) 0.0840(14) 0.0051(10) -0.0191(13) -0.0374(11) C37 0.0811(14) 0.0818(14) 0.0439(10) 0.0038(10) -0.0085(10) -0.0469(12) C38 0.0546(12) 0.0741(13) 0.0767(14) 0.0028(11) -0.0095(11) -0.0373(11) C39 0.0635(13) 0.0720(14) 0.0821(15) -0.0213(11) -0.0003(12) -0.0367(11) O2 0.0482(7) 0.0530(7) 0.0612(8) -0.0089(6) -0.0003(6) -0.0169(6) C6 0.0441(10) 0.0461(9) 0.0494(10) -0.0098(8) 0.0029(8) -0.0264(8) C7 0.0471(10) 0.0479(10) 0.0548(10) -0.0143(8) 0.0046(8) -0.0240(9) C9 0.0421(10) 0.0472(10) 0.0565(11) -0.0079(8) -0.0018(8) -0.0208(8) C13 0.0499(11) 0.0495(10) 0.0540(11) -0.0092(8) -0.0012(8) -0.0228(9) C16 0.0547(11) 0.0540(10) 0.0530(10) -0.0079(8) 0.0022(9) -0.0336(9) O18 0.0651(10) 0.0638(9) 0.0884(10) 0.0085(8) -0.0119(8) -0.0127(8) C19 0.0610(12) 0.0659(12) 0.0454(10) -0.0083(9) -0.0011(9) -0.0246(10) C20 0.0494(11) 0.0611(12) 0.0531(11) -0.0173(9) 0.0065(9) -0.0196(10) C22 0.0558(12) 0.0552(11) 0.0654(12) 0.0010(10) -0.0045(10) -0.0290(10) C24 0.0376(10) 0.0632(12) 0.0518(11) 0.0023(9) -0.0053(8) -0.0140(9) C25 0.0543(12) 0.0681(12) 0.0558(11) -0.0014(10) -0.0044(9) -0.0261(10) C27 0.0646(13) 0.0630(12) 0.0511(11) 0.0013(9) -0.0034(9) -0.0349(11) C29 0.0637(13) 0.0505(11) 0.0654(12) -0.0038(9) -0.0038(10) -0.0208(10) C31 0.0568(12) 0.0517(11) 0.0640(12) 0.0077(9) -0.0068(10) -0.0147(9) C32 0.0708(14) 0.0757(13) 0.0548(11) -0.0131(10) 0.0106(10) -0.0355(11) C33 0.0592(14) 0.0951(18) 0.1019(19) -0.0277(16) -0.0167(13) -0.0311(13) C35 0.0580(13) 0.0758(14) 0.0870(16) -0.0050(12) -0.0084(11) -0.0334(11) C36 0.0556(12) 0.0923(16) 0.0579(12) 0.0080(11) -0.0146(10) -0.0257(12) C40 0.0698(15) 0.125(2) 0.0632(14) -0.0157(15) -0.0177(12) -0.0352(15) _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 C17 1.376(2) . ? O1 C4 1.3796(18) . ? C3 C4 1.389(2) . ? C3 C5 1.399(2) . ? C3 C14 1.446(2) . ? C4 C8 1.377(2) . ? C5 C15 1.384(2) . ? C8 C12 1.373(2) . ? O10 C17 1.205(2) . ? C11 C14 1.338(2) . ? C11 C17 1.436(2) . ? C12 C15 1.395(2) . ? C14 C34 1.494(2) . ? C15 C23 1.474(2) . ? C21 C26 1.386(2) . ? C21 C28 1.388(2) . ? C21 C37 1.468(3) . ? C23 C37 1.326(2) . ? C26 C30 1.368(3) . ? C28 C39 1.375(3) . ? C30 C38 1.379(3) . ? C38 C39 1.368(3) . ? O2 C9 1.374(2) . ? O2 C22 1.378(2) . ? C6 C9 1.388(2) . ? C6 C7 1.403(2) . ? C6 C16 1.451(2) . ? C7 C13 1.383(2) . ? C9 C20 1.381(2) . ? C13 C19 1.398(2) . ? C13 C29 1.479(2) . ? C16 C27 1.345(2) . ? C16 C32 1.498(2) . ? O18 C22 1.200(2) . ? C19 C20 1.363(3) . ? C22 C27 1.438(3) . ? C24 C36 1.386(2) . ? C24 C25 1.396(3) . ? C24 C31 1.467(3) . ? C25 C35 1.375(3) . ? C29 C31 1.320(3) . ? C33 C35 1.364(3) . ? C33 C40 1.369(3) . ? C36 C40 1.383(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 C17 O1 C4 121.70(13) . . ? C4 C3 C5 116.95(15) . . ? C4 C3 C14 118.51(15) . . ? C5 C3 C14 124.54(15) . . ? C8 C4 O1 116.76(14) . . ? C8 C4 C3 122.05(15) . . ? O1 C4 C3 121.17(14) . . ? C15 C5 C3 122.67(15) . . ? C12 C8 C4 119.17(16) . . ? C14 C11 C17 123.67(16) . . ? C8 C12 C15 121.68(16) . . ? C11 C14 C3 118.36(16) . . ? C11 C14 C34 122.05(16) . . ? C3 C14 C34 119.59(16) . . ? C5 C15 C12 117.47(16) . . ? C5 C15 C23 120.48(16) . . ? C12 C15 C23 121.87(16) . . ? O10 C17 O1 116.79(17) . . ? O10 C17 C11 126.69(17) . . ? O1 C17 C11 116.52(16) . . ? C26 C21 C28 117.65(17) . . ? C26 C21 C37 121.28(16) . . ? C28 C21 C37 121.00(17) . . ? C37 C23 C15 128.66(18) . . ? C30 C26 C21 121.33(17) . . ? C39 C28 C21 121.07(18) . . ? C26 C30 C38 120.06(19) . . ? C23 C37 C21 128.21(17) . . ? C39 C38 C30 119.61(19) . . ? C38 C39 C28 120.25(18) . . ? C9 O2 C22 121.56(14) . . ? C9 C6 C7 117.61(16) . . ? C9 C6 C16 118.41(16) . . ? C7 C6 C16 123.96(16) . . ? C13 C7 C6 121.43(16) . . ? O2 C9 C20 116.31(15) . . ? O2 C9 C6 121.83(16) . . ? C20 C9 C6 121.86(17) . . ? C7 C13 C19 118.31(16) . . ? C7 C13 C29 121.36(16) . . ? C19 C13 C29 120.32(16) . . ? C27 C16 C6 117.75(16) . . ? C27 C16 C32 121.90(17) . . ? C6 C16 C32 120.32(17) . . ? C20 C19 C13 121.60(17) . . ? C19 C20 C9 119.17(17) . . ? O18 C22 O2 116.87(18) . . ? O18 C22 C27 126.78(19) . . ? O2 C22 C27 116.35(17) . . ? C36 C24 C25 117.49(19) . . ? C36 C24 C31 120.99(19) . . ? C25 C24 C31 121.40(16) . . ? C35 C25 C24 120.99(19) . . ? C16 C27 C22 124.03(17) . . ? C31 C29 C13 126.42(18) . . ? C29 C31 C24 127.90(18) . . ? C35 C33 C40 119.9(2) . . ? C33 C35 C25 120.4(2) . . ? C40 C36 C24 121.0(2) . . ? C33 C40 C36 120.1(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C17 O1 C4 C8 177.85(15) . . . . ? C17 O1 C4 C3 -0.5(2) . . . . ? C5 C3 C4 C8 -0.4(2) . . . . ? C14 C3 C4 C8 -179.98(16) . . . . ? C5 C3 C4 O1 177.90(14) . . . . ? C14 C3 C4 O1 -1.7(2) . . . . ? C4 C3 C5 C15 1.5(3) . . . . ? C14 C3 C5 C15 -178.92(16) . . . . ? O1 C4 C8 C12 -179.12(15) . . . . ? C3 C4 C8 C12 -0.8(3) . . . . ? C4 C8 C12 C15 0.9(3) . . . . ? C17 C11 C14 C3 0.3(3) . . . . ? C17 C11 C14 C34 180.00(18) . . . . ? C4 C3 C14 C11 1.8(2) . . . . ? C5 C3 C14 C11 -177.80(16) . . . . ? C4 C3 C14 C34 -177.92(16) . . . . ? C5 C3 C14 C34 2.5(3) . . . . ? C3 C5 C15 C12 -1.4(3) . . . . ? C3 C5 C15 C23 -176.52(16) . . . . ? C8 C12 C15 C5 0.2(3) . . . . ? C8 C12 C15 C23 175.22(17) . . . . ? C4 O1 C17 O10 -177.17(16) . . . . ? C4 O1 C17 C11 2.5(2) . . . . ? C14 C11 C17 O10 177.20(19) . . . . ? C14 C11 C17 O1 -2.5(3) . . . . ? C5 C15 C23 C37 -143.9(2) . . . . ? C12 C15 C23 C37 41.2(3) . . . . ? C28 C21 C26 C30 0.6(3) . . . . ? C37 C21 C26 C30 177.46(17) . . . . ? C26 C21 C28 C39 -1.4(3) . . . . ? C37 C21 C28 C39 -178.26(18) . . . . ? C21 C26 C30 C38 0.8(3) . . . . ? C15 C23 C37 C21 7.9(4) . . . . ? C26 C21 C37 C23 41.3(3) . . . . ? C28 C21 C37 C23 -142.0(2) . . . . ? C26 C30 C38 C39 -1.4(3) . . . . ? C30 C38 C39 C28 0.6(3) . . . . ? C21 C28 C39 C38 0.8(3) . . . . ? C9 C6 C7 C13 1.3(2) . . . . ? C16 C6 C7 C13 -177.19(14) . . . . ? C22 O2 C9 C20 179.48(15) . . . . ? C22 O2 C9 C6 -0.9(2) . . . . ? C7 C6 C9 O2 -179.94(14) . . . . ? C16 C6 C9 O2 -1.4(2) . . . . ? C7 C6 C9 C20 -0.3(2) . . . . ? C16 C6 C9 C20 178.25(16) . . . . ? C6 C7 C13 C19 -1.4(2) . . . . ? C6 C7 C13 C29 -179.81(16) . . . . ? C9 C6 C16 C27 1.6(2) . . . . ? C7 C6 C16 C27 -179.97(15) . . . . ? C9 C6 C16 C32 -176.91(15) . . . . ? C7 C6 C16 C32 1.6(2) . . . . ? C7 C13 C19 C20 0.5(3) . . . . ? C29 C13 C19 C20 178.93(17) . . . . ? C13 C19 C20 C9 0.5(3) . . . . ? O2 C9 C20 C19 179.09(15) . . . . ? C6 C9 C20 C19 -0.6(3) . . . . ? C9 O2 C22 O18 -178.12(15) . . . . ? C9 O2 C22 C27 2.7(2) . . . . ? C36 C24 C25 C35 1.4(3) . . . . ? C31 C24 C25 C35 177.33(18) . . . . ? C6 C16 C27 C22 0.4(3) . . . . ? C32 C16 C27 C22 178.86(16) . . . . ? O18 C22 C27 C16 178.41(19) . . . . ? O2 C22 C27 C16 -2.6(3) . . . . ? C7 C13 C29 C31 -133.9(2) . . . . ? C19 C13 C29 C31 47.6(3) . . . . ? C13 C29 C31 C24 8.6(3) . . . . ? C36 C24 C31 C29 -143.6(2) . . . . ? C25 C24 C31 C29 40.5(3) . . . . ? C40 C33 C35 C25 -0.5(3) . . . . ? C24 C25 C35 C33 -0.4(3) . . . . ? C25 C24 C36 C40 -1.5(3) . . . . ? C31 C24 C36 C40 -177.50(19) . . . . ? C35 C33 C40 C36 0.4(3) . . . . ? C24 C36 C40 C33 0.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.178 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.032 _chemical_compound_source synthetic _exptl_crystal_recrystallization_method Evaporation #END data_4s7slt _database_code_depnum_ccdc_archive 'CCDC 611804' _audit_creation_method SHELXL-97 _chemical_name_systematic 4-methyl-7-styrylcoumarin _chemical_name_common ? _chemical_melting_point 110-114C _chemical_formula_moiety 'C18 H14 O2' _chemical_formula_sum 'C18 H14 O2' _chemical_formula_weight 262.29 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 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 6.7273(6) _cell_length_b 8.3794(8) _cell_length_c 24.102(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.362(2) _cell_angle_gamma 90.00 _cell_volume 1358.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker Nonius Ceramic tube' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8815 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 28.34 _reflns_number_total 3355 _reflns_number_gt 2353 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0795P)^2^+0.0773P] 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 3355 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1482 _refine_ls_wR_factor_gt 0.1338 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 O1 O 1.07193(15) 0.29171(12) 0.48203(4) 0.0536(3) Uani 1 1 d . . . C2 C 0.9437(2) 0.09819(16) 0.41686(5) 0.0443(3) Uani 1 1 d . . . C3 C 0.7861(2) 0.05639(16) 0.38155(6) 0.0490(3) Uani 1 1 d . . . H3 H 0.7891 -0.0412 0.3632 0.059 Uiso 1 1 calc R . . C4 C 0.6278(2) 0.15612(17) 0.37348(6) 0.0498(3) Uani 1 1 d . . . H4 H 0.5245 0.1244 0.3501 0.060 Uiso 1 1 calc R . . C5 C 0.6179(2) 0.30529(16) 0.39972(6) 0.0466(3) Uani 1 1 d . . . O2 O 1.35017(18) 0.24901(14) 0.52828(5) 0.0738(4) Uani 1 1 d . . . C7 C 1.1176(2) 0.00037(18) 0.42691(6) 0.0496(3) Uani 1 1 d . . . C8 C 0.7713(2) 0.34648(17) 0.43601(6) 0.0482(3) Uani 1 1 d . . . H8 H 0.7675 0.4434 0.4547 0.058 Uiso 1 1 calc R . . C9 C 0.9290(2) 0.24362(16) 0.44421(5) 0.0442(3) Uani 1 1 d . . . C10 C 1.2533(2) 0.05115(19) 0.46376(6) 0.0558(4) Uani 1 1 d . . . H10 H 1.3645 -0.0123 0.4702 0.067 Uiso 1 1 calc R . . C11 C 0.4484(2) 0.41491(17) 0.39440(6) 0.0528(4) Uani 1 1 d . . . H11 H 0.4393 0.4907 0.4225 0.063 Uiso 1 1 calc R . . C12 C 0.2814(2) 0.33587(17) 0.30327(6) 0.0497(4) Uani 1 1 d . . . C13 C 1.2361(2) 0.1985(2) 0.49377(6) 0.0550(4) Uani 1 1 d . . . C14 C 0.3053(2) 0.42364(18) 0.35591(6) 0.0556(4) Uani 1 1 d . . . H14 H 0.2049 0.4966 0.3635 0.067 Uiso 1 1 calc R . . C15 C 0.4342(2) 0.31949(19) 0.26544(6) 0.0590(4) Uani 1 1 d . . . H15 H 0.5577 0.3645 0.2731 0.071 Uiso 1 1 calc R . . C16 C 1.1443(3) -0.1538(2) 0.39656(7) 0.0700(5) Uani 1 1 d . . . H16A H 1.2673 -0.2024 0.4079 0.105 Uiso 1 1 calc R . . H16B H 1.1469 -0.1337 0.3574 0.105 Uiso 1 1 calc R . . H16C H 1.0360 -0.2241 0.4050 0.105 Uiso 1 1 calc R . . C17 C 0.0981(2) 0.27184(19) 0.28959(7) 0.0611(4) Uani 1 1 d . . . H17 H -0.0084 0.2862 0.3135 0.073 Uiso 1 1 calc R . . C18 C 0.2241(3) 0.1693(2) 0.20472(8) 0.0767(6) Uani 1 1 d . . . H18 H 0.2057 0.1114 0.1722 0.092 Uiso 1 1 calc R . . C19 C 0.0702(3) 0.1874(2) 0.24132(8) 0.0757(5) Uani 1 1 d . . . H19 H -0.0531 0.1423 0.2334 0.091 Uiso 1 1 calc R . . C20 C 0.4053(3) 0.2372(2) 0.21643(7) 0.0695(5) Uani 1 1 d . . . H20 H 0.5089 0.2277 0.1913 0.083 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0547(6) 0.0501(6) 0.0559(6) -0.0104(4) -0.0144(5) 0.0038(5) C2 0.0476(8) 0.0427(7) 0.0426(7) -0.0015(6) -0.0026(5) 0.0019(6) C3 0.0546(8) 0.0399(7) 0.0524(7) -0.0068(6) -0.0080(6) 0.0016(6) C4 0.0485(8) 0.0438(7) 0.0569(8) -0.0038(6) -0.0112(6) -0.0012(6) C5 0.0473(8) 0.0435(7) 0.0489(7) -0.0006(6) -0.0029(6) 0.0021(6) O2 0.0717(8) 0.0716(8) 0.0776(7) -0.0133(6) -0.0328(6) 0.0033(6) C7 0.0506(8) 0.0501(8) 0.0482(7) -0.0031(6) -0.0016(6) 0.0073(6) C8 0.0534(8) 0.0398(7) 0.0513(8) -0.0062(6) -0.0034(6) 0.0019(6) C9 0.0461(8) 0.0448(7) 0.0416(7) -0.0033(6) -0.0049(5) -0.0014(6) C10 0.0486(8) 0.0590(9) 0.0596(8) -0.0027(7) -0.0092(7) 0.0106(7) C11 0.0536(9) 0.0463(8) 0.0586(8) -0.0086(6) -0.0035(6) 0.0070(6) C12 0.0512(8) 0.0386(7) 0.0591(8) 0.0052(6) -0.0108(6) 0.0047(6) C13 0.0520(9) 0.0575(9) 0.0552(8) -0.0008(7) -0.0107(7) 0.0014(7) C14 0.0496(8) 0.0488(9) 0.0683(9) -0.0030(7) -0.0048(7) 0.0109(7) C15 0.0576(9) 0.0518(9) 0.0675(10) 0.0007(7) -0.0052(7) 0.0005(7) C16 0.0690(11) 0.0661(11) 0.0748(11) -0.0210(9) -0.0105(8) 0.0233(9) C17 0.0553(9) 0.0571(10) 0.0707(10) 0.0098(8) -0.0124(7) -0.0009(7) C18 0.1062(16) 0.0579(11) 0.0658(11) -0.0070(8) -0.0276(11) 0.0107(10) C19 0.0783(13) 0.0627(11) 0.0857(13) 0.0030(9) -0.0312(11) -0.0093(9) C20 0.0873(13) 0.0597(10) 0.0614(10) 0.0001(8) 0.0008(9) 0.0142(9) _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 C13 1.3803(18) . ? O1 C9 1.3807(16) . ? C2 C9 1.3893(19) . ? C2 C3 1.4000(18) . ? C2 C7 1.4478(19) . ? C3 C4 1.3667(19) . ? C4 C5 1.403(2) . ? C5 C8 1.3919(19) . ? C5 C11 1.4694(19) . ? O2 C13 1.2048(17) . ? C7 C10 1.3390(19) . ? C7 C16 1.496(2) . ? C8 C9 1.3803(19) . ? C10 C13 1.436(2) . ? C11 C14 1.334(2) . ? C12 C17 1.383(2) . ? C12 C15 1.385(2) . ? C12 C14 1.474(2) . ? C15 C20 1.381(2) . ? C17 C19 1.374(2) . ? C18 C19 1.373(3) . ? C18 C20 1.373(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 C13 O1 C9 121.55(11) . . ? C9 C2 C3 116.86(12) . . ? C9 C2 C7 118.49(12) . . ? C3 C2 C7 124.64(12) . . ? C4 C3 C2 121.35(12) . . ? C3 C4 C5 121.31(12) . . ? C8 C5 C4 117.86(12) . . ? C8 C5 C11 118.15(12) . . ? C4 C5 C11 123.82(13) . . ? C10 C7 C2 118.55(13) . . ? C10 C7 C16 121.02(13) . . ? C2 C7 C16 120.43(13) . . ? C9 C8 C5 120.09(13) . . ? O1 C9 C8 116.34(12) . . ? O1 C9 C2 121.19(12) . . ? C8 C9 C2 122.46(12) . . ? C7 C10 C13 123.39(14) . . ? C14 C11 C5 130.61(13) . . ? C17 C12 C15 117.97(15) . . ? C17 C12 C14 119.40(14) . . ? C15 C12 C14 122.58(14) . . ? O2 C13 O1 116.64(14) . . ? O2 C13 C10 126.61(14) . . ? O1 C13 C10 116.75(12) . . ? C11 C14 C12 130.17(14) . . ? C20 C15 C12 120.77(16) . . ? C19 C17 C12 121.22(17) . . ? C19 C18 C20 119.63(17) . . ? C18 C19 C17 120.13(18) . . ? C18 C20 C15 120.20(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C2 C3 C4 1.5(2) . . . . ? C7 C2 C3 C4 -179.03(13) . . . . ? C2 C3 C4 C5 0.8(2) . . . . ? C3 C4 C5 C8 -2.3(2) . . . . ? C3 C4 C5 C11 -177.54(14) . . . . ? C9 C2 C7 C10 2.6(2) . . . . ? C3 C2 C7 C10 -176.87(14) . . . . ? C9 C2 C7 C16 -177.32(14) . . . . ? C3 C2 C7 C16 3.3(2) . . . . ? C4 C5 C8 C9 1.5(2) . . . . ? C11 C5 C8 C9 177.04(13) . . . . ? C13 O1 C9 C8 179.81(12) . . . . ? C13 O1 C9 C2 0.7(2) . . . . ? C5 C8 C9 O1 -178.26(12) . . . . ? C5 C8 C9 C2 0.8(2) . . . . ? C3 C2 C9 O1 176.68(12) . . . . ? C7 C2 C9 O1 -2.8(2) . . . . ? C3 C2 C9 C8 -2.3(2) . . . . ? C7 C2 C9 C8 178.20(13) . . . . ? C2 C7 C10 C13 -0.3(2) . . . . ? C16 C7 C10 C13 179.54(15) . . . . ? C8 C5 C11 C14 164.37(16) . . . . ? C4 C5 C11 C14 -20.4(3) . . . . ? C9 O1 C13 O2 -178.35(13) . . . . ? C9 O1 C13 C10 1.5(2) . . . . ? C7 C10 C13 O2 178.13(16) . . . . ? C7 C10 C13 O1 -1.7(2) . . . . ? C5 C11 C14 C12 -6.6(3) . . . . ? C17 C12 C14 C11 134.42(18) . . . . ? C15 C12 C14 C11 -48.1(2) . . . . ? C17 C12 C15 C20 -2.1(2) . . . . ? C14 C12 C15 C20 -179.58(15) . . . . ? C15 C12 C17 C19 3.3(2) . . . . ? C14 C12 C17 C19 -179.09(15) . . . . ? C20 C18 C19 C17 -0.5(3) . . . . ? C12 C17 C19 C18 -2.0(3) . . . . ? C19 C18 C20 C15 1.7(3) . . . . ? C12 C15 C20 C18 -0.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.183 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.049 _chemical_compound_source synthetic _exptl_crystal_recrystallization_method Evaporation #END data_6c-sty _database_code_depnum_ccdc_archive 'CCDC 611805' _audit_creation_method SHELXL-97 _chemical_name_systematic 6-styrylcoumarin _chemical_name_common ? _chemical_melting_point 78-80C _chemical_formula_moiety 'C17 H12 O2' _chemical_formula_sum 'C17 H12 O2' _chemical_formula_weight 248.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 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 11.599(5) _cell_length_b 6.519(5) _cell_length_c 16.717(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 97.350(5) _cell_angle_gamma 90.091(5) _cell_volume 1253.6(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker Nonius Ceramic tube' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1784 _diffrn_reflns_av_R_equivalents 0.0139 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 22.48 _reflns_number_total 1622 _reflns_number_gt 992 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0857P)^2^+2.0064P] 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 0.016(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1622 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1343 _refine_ls_R_factor_gt 0.0719 _refine_ls_wR_factor_ref 0.2202 _refine_ls_wR_factor_gt 0.1875 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 O1 O 0.9004(3) 0.3476(5) 1.04519(19) 0.0579(10) Uiso 1 1 d . . . O2 O 0.9448(3) 0.4414(7) 1.1714(2) 0.0798(13) Uiso 1 1 d . . . C3 C 0.8659(4) 0.2018(7) 0.9880(3) 0.0471(12) Uiso 1 1 d . . . C4 C 0.8467(4) 0.0009(8) 1.0088(3) 0.0475(12) Uiso 1 1 d . . . C5 C 0.8106(4) -0.1389(8) 0.9480(3) 0.0530(13) Uiso 1 1 d . . . C6 C 0.9185(4) 0.2993(8) 1.1254(3) 0.0574(14) Uiso 1 1 d . . . C7 C 0.8695(4) -0.0519(9) 1.0927(3) 0.0598(14) Uiso 1 1 d . . . C8 C 0.7949(4) -0.0803(8) 0.8679(3) 0.0529(13) Uiso 1 1 d . . . C9 C 0.8516(4) 0.2644(9) 0.9083(3) 0.0602(15) Uiso 1 1 d . . . C10 C 0.5308(5) -0.2061(11) 0.8788(4) 0.0744(18) Uiso 1 1 d . . . C11 C 0.9040(5) 0.0891(8) 1.1479(3) 0.0607(15) Uiso 1 1 d . . . C12 C 0.6723(5) -0.3562(9) 0.7930(4) 0.0671(16) Uiso 1 1 d . . . C13 C 0.7608(5) -0.2297(9) 0.8020(3) 0.0641(15) Uiso 1 1 d . . . C14 C 0.5754(4) -0.3723(8) 0.8408(3) 0.0619(15) Uiso 1 1 d . . . C15 C 0.8171(4) 0.1230(9) 0.8499(4) 0.0627(16) Uiso 1 1 d . . . C16 C 0.5215(6) -0.5603(11) 0.8460(4) 0.0806(19) Uiso 1 1 d . . . C17 C 0.4357(6) -0.2278(12) 0.9214(4) 0.088(2) Uiso 1 1 d . . . C18 C 0.3872(7) -0.4160(13) 0.9264(5) 0.094(2) Uiso 1 1 d . . . C19 C 0.4270(7) -0.5806(14) 0.8883(5) 0.097(2) Uiso 1 1 d . . . H1 H 0.799(5) -0.284(9) 0.963(3) 0.093(18) Uiso 1 1 d . . . H2 H 0.852(6) -0.197(11) 1.106(4) 0.12(2) Uiso 1 1 d . . . H3 H 0.875(6) 0.410(11) 0.900(4) 0.12(2) Uiso 1 1 d . . . H4 H 0.561(4) -0.086(8) 0.868(3) 0.068(15) Uiso 1 1 d . . . H5 H 0.925(5) 0.070(11) 1.206(4) 0.13(2) Uiso 1 1 d . . . H6 H 0.670(5) -0.457(10) 0.748(4) 0.11(2) Uiso 1 1 d . . . H7 H 0.816(5) -0.219(9) 0.767(4) 0.10(2) Uiso 1 1 d . . . H8 H 0.805(5) 0.160(9) 0.794(4) 0.11(2) Uiso 1 1 d . . . H9 H 0.558(5) -0.659(9) 0.818(3) 0.086(18) Uiso 1 1 d . . . H10 H 0.419(6) -0.099(10) 0.949(4) 0.12(2) Uiso 1 1 d . . . H11 H 0.342(7) -0.441(13) 0.965(5) 0.16(3) Uiso 1 1 d . . . H12 H 0.411(6) -0.713(11) 0.901(4) 0.12(2) Uiso 1 1 d . . . _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 C6 1.368(6) . ? O1 C3 1.371(5) . ? O2 C6 1.217(6) . ? C3 C4 1.380(7) . ? C3 C9 1.384(7) . ? C4 C5 1.388(7) . ? C4 C7 1.436(7) . ? C5 C8 1.382(7) . ? C6 C11 1.436(7) . ? C7 C11 1.328(7) . ? C8 C15 1.390(7) . ? C8 C13 1.486(7) . ? C9 C15 1.365(8) . ? C10 C14 1.389(8) . ? C10 C17 1.393(8) . ? C12 C13 1.309(7) . ? C12 C14 1.463(7) . ? C14 C16 1.383(8) . ? C16 C19 1.385(9) . ? C17 C18 1.356(10) . ? C18 C19 1.359(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 C6 O1 C3 121.2(4) . . ? O1 C3 C4 121.6(4) . . ? O1 C3 C9 117.1(4) . . ? C4 C3 C9 121.3(5) . . ? C3 C4 C5 118.8(5) . . ? C3 C4 C7 117.3(5) . . ? C5 C4 C7 123.9(5) . . ? C8 C5 C4 121.2(5) . . ? O2 C6 O1 116.0(5) . . ? O2 C6 C11 126.1(5) . . ? O1 C6 C11 117.9(5) . . ? C11 C7 C4 121.0(5) . . ? C5 C8 C15 118.0(5) . . ? C5 C8 C13 121.8(5) . . ? C15 C8 C13 120.1(5) . . ? C15 C9 C3 118.6(6) . . ? C14 C10 C17 121.4(7) . . ? C7 C11 C6 120.9(5) . . ? C13 C12 C14 128.9(6) . . ? C12 C13 C8 128.8(6) . . ? C16 C14 C10 117.7(6) . . ? C16 C14 C12 118.8(5) . . ? C10 C14 C12 123.5(5) . . ? C9 C15 C8 122.2(6) . . ? C14 C16 C19 120.6(7) . . ? C18 C17 C10 118.9(8) . . ? C17 C18 C19 121.2(8) . . ? C18 C19 C16 120.2(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 O1 C3 C4 0.7(6) . . . . ? C6 O1 C3 C9 -178.9(4) . . . . ? O1 C3 C4 C5 179.3(4) . . . . ? C9 C3 C4 C5 -1.1(7) . . . . ? O1 C3 C4 C7 -2.7(7) . . . . ? C9 C3 C4 C7 176.9(4) . . . . ? C3 C4 C5 C8 0.6(7) . . . . ? C7 C4 C5 C8 -177.2(5) . . . . ? C3 O1 C6 O2 -177.3(4) . . . . ? C3 O1 C6 C11 2.1(6) . . . . ? C3 C4 C7 C11 2.0(7) . . . . ? C5 C4 C7 C11 179.9(5) . . . . ? C4 C5 C8 C15 0.4(7) . . . . ? C4 C5 C8 C13 177.5(5) . . . . ? O1 C3 C9 C15 -179.9(4) . . . . ? C4 C3 C9 C15 0.5(8) . . . . ? C4 C7 C11 C6 0.7(8) . . . . ? O2 C6 C11 C7 176.6(5) . . . . ? O1 C6 C11 C7 -2.7(8) . . . . ? C14 C12 C13 C8 6.8(10) . . . . ? C5 C8 C13 C12 53.9(8) . . . . ? C15 C8 C13 C12 -129.0(7) . . . . ? C17 C10 C14 C16 0.6(9) . . . . ? C17 C10 C14 C12 177.7(6) . . . . ? C13 C12 C14 C16 -151.8(6) . . . . ? C13 C12 C14 C10 31.1(9) . . . . ? C3 C9 C15 C8 0.6(8) . . . . ? C5 C8 C15 C9 -1.0(8) . . . . ? C13 C8 C15 C9 -178.2(5) . . . . ? C10 C14 C16 C19 -0.5(9) . . . . ? C12 C14 C16 C19 -177.8(6) . . . . ? C14 C10 C17 C18 0.8(10) . . . . ? C10 C17 C18 C19 -2.3(11) . . . . ? C17 C18 C19 C16 2.5(12) . . . . ? C14 C16 C19 C18 -1.0(11) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 22.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.288 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.053 _chemical_compound_source synthetic _exptl_crystal_recrystallization_method Evaporation #END data_4u7s _database_code_depnum_ccdc_archive 'CCDC 611806' _audit_creation_method SHELXL-97 _chemical_name_systematic 7-styrylcoumarin _chemical_name_common ? _chemical_melting_point 86-88C _chemical_formula_moiety 'C17 H12 O2' _chemical_formula_sum 'C17 H12 O2' _chemical_formula_weight 248.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.664(4) _cell_length_b 9.257(5) _cell_length_c 11.010(6) _cell_angle_alpha 89.124(7) _cell_angle_beta 81.640(7) _cell_angle_gamma 75.963(7) _cell_volume 651.8(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 143 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker Nonius Ceramic tube' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4192 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0973 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 28.35 _reflns_number_total 3065 _reflns_number_gt 1309 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0636P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3065 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1926 _refine_ls_R_factor_gt 0.0777 _refine_ls_wR_factor_ref 0.1857 _refine_ls_wR_factor_gt 0.1421 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 O2 O 0.3168(3) -0.1486(2) 0.65395(19) 0.0569(6) Uani 1 1 d . . . C1 C 0.0975(5) 0.0885(3) 0.6971(3) 0.0500(8) Uani 1 1 d . . . H1 H 0.2133 0.1195 0.7143 0.060 Uiso 1 1 calc R . . C2 C 0.1169(5) -0.0571(3) 0.6620(3) 0.0446(7) Uani 1 1 d . . . C3 C -0.0472(5) -0.1104(3) 0.6357(3) 0.0461(8) Uani 1 1 d . . . C4 C -0.2414(5) -0.0089(4) 0.6434(3) 0.0577(9) Uani 1 1 d . . . H4 H -0.3564 -0.0401 0.6252 0.069 Uiso 1 1 calc R . . C5 C -0.0978(5) 0.1888(3) 0.7066(3) 0.0490(8) Uani 1 1 d . . . C6 C -0.2638(5) 0.1362(4) 0.6775(3) 0.0588(9) Uani 1 1 d . . . H6 H -0.3946 0.2020 0.6813 0.071 Uiso 1 1 calc R . . C7 C -0.0060(5) -0.2648(3) 0.6029(3) 0.0583(9) Uani 1 1 d . . . H7 H -0.1148 -0.3047 0.5865 0.070 Uiso 1 1 calc R . . C8 C 0.3598(6) -0.2969(3) 0.6180(3) 0.0609(9) Uani 1 1 d . . . C9 C 0.1869(6) -0.3521(4) 0.5954(3) 0.0609(9) Uani 1 1 d . . . H9 H 0.2090 -0.4524 0.5748 0.073 Uiso 1 1 calc R . . O1 O 0.5382(4) -0.3653(3) 0.6110(3) 0.0962(10) Uani 1 1 d . . . C10 C 0.1143(5) 0.3308(3) 0.8978(3) 0.0511(8) Uani 1 1 d . . . C11 C -0.1292(5) 0.3469(3) 0.7410(3) 0.0607(10) Uani 1 1 d . . . H11 H -0.2289 0.4139 0.7039 0.073 Uiso 1 1 calc R . . C12 C -0.0345(5) 0.4058(3) 0.8177(3) 0.0607(10) Uani 1 1 d . . . H12 H -0.0668 0.5094 0.8212 0.073 Uiso 1 1 calc R . . C13 C 0.0766(6) 0.2141(3) 0.9705(3) 0.0607(9) Uani 1 1 d . . . H13 H -0.0432 0.1805 0.9671 0.073 Uiso 1 1 calc R . . C14 C 0.2897(6) 0.3801(4) 0.9076(3) 0.0681(10) Uani 1 1 d . . . H14 H 0.3162 0.4598 0.8609 0.082 Uiso 1 1 calc R . . C15 C 0.2148(7) 0.1476(4) 1.0475(3) 0.0718(11) Uani 1 1 d . . . H15 H 0.1885 0.0685 1.0951 0.086 Uiso 1 1 calc R . . C16 C 0.3906(6) 0.1962(4) 1.0552(3) 0.0774(12) Uani 1 1 d . . . H16 H 0.4840 0.1502 1.1073 0.093 Uiso 1 1 calc R . . C17 C 0.4276(6) 0.3127(4) 0.9859(4) 0.0785(12) Uani 1 1 d . . . H17 H 0.5461 0.3470 0.9912 0.094 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0454(14) 0.0478(12) 0.0761(16) -0.0088(11) -0.0184(12) -0.0023(10) C1 0.0433(19) 0.0510(18) 0.055(2) 0.0012(15) -0.0087(16) -0.0098(14) C2 0.0384(19) 0.0493(18) 0.0431(18) 0.0028(14) -0.0049(15) -0.0056(14) C3 0.044(2) 0.058(2) 0.0380(18) 0.0025(14) -0.0043(15) -0.0174(15) C4 0.040(2) 0.077(2) 0.055(2) 0.0009(18) -0.0074(16) -0.0132(17) C5 0.047(2) 0.0534(19) 0.0409(19) 0.0039(14) -0.0053(16) -0.0027(15) C6 0.044(2) 0.066(2) 0.057(2) 0.0002(17) -0.0051(17) 0.0043(16) C7 0.059(2) 0.063(2) 0.059(2) 0.0006(17) -0.0074(18) -0.0278(18) C8 0.063(2) 0.048(2) 0.070(2) -0.0062(16) -0.0219(19) -0.0010(17) C9 0.068(2) 0.0487(19) 0.068(2) -0.0032(16) -0.014(2) -0.0159(18) O1 0.0609(18) 0.0647(16) 0.154(3) -0.0250(15) -0.0358(17) 0.0153(13) C10 0.062(2) 0.0425(18) 0.0439(19) -0.0068(15) 0.0032(17) -0.0080(16) C11 0.061(2) 0.052(2) 0.057(2) 0.0061(17) -0.0029(19) 0.0049(17) C12 0.076(3) 0.0422(18) 0.056(2) -0.0016(16) 0.0017(19) -0.0042(17) C13 0.069(2) 0.062(2) 0.051(2) -0.0003(17) -0.0020(19) -0.0181(18) C14 0.082(3) 0.048(2) 0.073(3) -0.0096(18) 0.003(2) -0.0194(19) C15 0.093(3) 0.065(2) 0.055(2) -0.0018(18) -0.017(2) -0.011(2) C16 0.083(3) 0.074(3) 0.067(3) -0.013(2) -0.019(2) 0.003(2) C17 0.064(3) 0.078(3) 0.093(3) -0.019(2) -0.008(2) -0.017(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C8 1.384(3) . ? O2 C2 1.386(3) . ? C1 C2 1.378(4) . ? C1 C5 1.394(4) . ? C2 C3 1.372(4) . ? C3 C4 1.396(4) . ? C3 C7 1.430(4) . ? C4 C6 1.367(4) . ? C5 C6 1.390(4) . ? C5 C11 1.475(4) . ? C7 C9 1.334(4) . ? C8 O1 1.196(3) . ? C8 C9 1.423(5) . ? C10 C14 1.371(4) . ? C10 C13 1.385(4) . ? C10 C12 1.465(4) . ? C11 C12 1.321(4) . ? C13 C15 1.372(4) . ? C14 C17 1.383(4) . ? C15 C16 1.367(5) . ? C16 C17 1.362(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O2 C2 121.5(3) . . ? C2 C1 C5 119.2(3) . . ? C3 C2 C1 123.5(3) . . ? C3 C2 O2 121.2(3) . . ? C1 C2 O2 115.3(3) . . ? C2 C3 C4 117.0(3) . . ? C2 C3 C7 117.7(3) . . ? C4 C3 C7 125.3(3) . . ? C6 C4 C3 120.4(3) . . ? C6 C5 C1 117.6(3) . . ? C6 C5 C11 120.2(3) . . ? C1 C5 C11 122.2(3) . . ? C4 C6 C5 122.3(3) . . ? C9 C7 C3 120.7(3) . . ? O1 C8 O2 116.4(3) . . ? O1 C8 C9 127.0(3) . . ? O2 C8 C9 116.6(3) . . ? C7 C9 C8 122.1(3) . . ? C14 C10 C13 118.2(3) . . ? C14 C10 C12 120.5(3) . . ? C13 C10 C12 121.2(3) . . ? C12 C11 C5 128.5(3) . . ? C11 C12 C10 129.0(3) . . ? C15 C13 C10 120.5(4) . . ? C10 C14 C17 120.9(4) . . ? C16 C15 C13 120.8(4) . . ? C17 C16 C15 119.3(4) . . ? C16 C17 C14 120.3(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C1 C2 C3 -0.3(5) . . . . ? C5 C1 C2 O2 179.5(3) . . . . ? C8 O2 C2 C3 0.7(4) . . . . ? C8 O2 C2 C1 -179.0(3) . . . . ? C1 C2 C3 C4 1.3(4) . . . . ? O2 C2 C3 C4 -178.4(3) . . . . ? C1 C2 C3 C7 -178.7(3) . . . . ? O2 C2 C3 C7 1.6(4) . . . . ? C2 C3 C4 C6 -0.9(4) . . . . ? C7 C3 C4 C6 179.1(3) . . . . ? C2 C1 C5 C6 -1.2(4) . . . . ? C2 C1 C5 C11 -178.6(3) . . . . ? C3 C4 C6 C5 -0.5(5) . . . . ? C1 C5 C6 C4 1.6(5) . . . . ? C11 C5 C6 C4 179.1(3) . . . . ? C2 C3 C7 C9 -1.6(5) . . . . ? C4 C3 C7 C9 178.4(3) . . . . ? C2 O2 C8 O1 178.2(3) . . . . ? C2 O2 C8 C9 -2.9(4) . . . . ? C3 C7 C9 C8 -0.8(5) . . . . ? O1 C8 C9 C7 -178.3(4) . . . . ? O2 C8 C9 C7 3.0(5) . . . . ? C6 C5 C11 C12 148.1(4) . . . . ? C1 C5 C11 C12 -34.5(5) . . . . ? C5 C11 C12 C10 -5.9(6) . . . . ? C14 C10 C12 C11 136.7(4) . . . . ? C13 C10 C12 C11 -46.8(5) . . . . ? C14 C10 C13 C15 -1.7(4) . . . . ? C12 C10 C13 C15 -178.3(3) . . . . ? C13 C10 C14 C17 1.4(5) . . . . ? C12 C10 C14 C17 178.0(3) . . . . ? C10 C13 C15 C16 0.8(5) . . . . ? C13 C15 C16 C17 0.4(5) . . . . ? C15 C16 C17 C14 -0.6(5) . . . . ? C10 C14 C17 C16 -0.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.151 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.038 _chemical_compound_source synthetic _exptl_crystal_recrystallization_method Evaporation #END data_4u6s_trans _database_code_depnum_ccdc_archive 'CCDC 611807' _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-6-styrylcoumarin ; _chemical_name_common ? _chemical_melting_point 132-134C _chemical_formula_moiety 'C17 H12 O2' _chemical_formula_sum 'C17 H12 O2' _chemical_formula_weight 248.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' _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 9.0520(18) _cell_length_b 5.8270(12) _cell_length_c 24.009(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.84(3) _cell_angle_gamma 90.00 _cell_volume 1264.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 172 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 22.5 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _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 3369 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0497 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 22.53 _reflns_number_total 1654 _reflns_number_gt 1077 _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 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0861P)^2^+0.0221P] 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 1654 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1365 _refine_ls_wR_factor_gt 0.1170 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 O1 O 1.12575(17) 0.7608(3) 0.02172(6) 0.0575(5) Uani 1 1 d . . . C1 C 1.0890(2) 1.0285(4) 0.09622(8) 0.0405(5) Uani 1 1 d . . . C2 C 1.0575(2) 0.8214(4) 0.06930(9) 0.0443(6) Uani 1 1 d . . . C3 C 0.6590(2) 0.9253(4) 0.29026(8) 0.0422(6) Uani 1 1 d . . . C4 C 0.9176(2) 0.9262(4) 0.16667(8) 0.0441(6) Uani 1 1 d . . . C5 C 0.7405(2) 0.8665(4) 0.24152(9) 0.0495(6) Uani 1 1 d . . . H5 H 0.7171 0.7256 0.2252 0.059 Uiso 1 1 calc R . . C6 C 0.5549(2) 0.7710(4) 0.30891(9) 0.0500(6) Uani 1 1 d . . . H6 H 0.5406 0.6323 0.2903 0.060 Uiso 1 1 calc R . . C7 C 0.8427(2) 0.9855(4) 0.21752(10) 0.0504(6) Uani 1 1 d . . . H7 H 0.8709 1.1229 0.2347 0.060 Uiso 1 1 calc R . . C8 C 1.0181(2) 1.0765(4) 0.14492(8) 0.0442(6) Uani 1 1 d . . . H8 H 1.0388 1.2138 0.1634 0.053 Uiso 1 1 calc R . . C9 C 0.6755(2) 1.1333(4) 0.31898(9) 0.0487(6) Uani 1 1 d . . . H9 H 0.7440 1.2403 0.3076 0.058 Uiso 1 1 calc R . . C10 C 0.9563(2) 0.6680(4) 0.08935(10) 0.0504(6) Uani 1 1 d . . . H10 H 0.9345 0.5319 0.0704 0.060 Uiso 1 1 calc R . . C11 C 0.4911(2) 1.0243(4) 0.38179(9) 0.0546(7) Uani 1 1 d . . . H11 H 0.4358 1.0570 0.4124 0.066 Uiso 1 1 calc R . . C12 C 1.2621(3) 1.1156(4) 0.02622(10) 0.0584(7) Uani 1 1 d . . . H12 H 1.3296 1.2152 0.0111 0.070 Uiso 1 1 calc R . . C13 C 1.2320(3) 0.8970(5) -0.00049(10) 0.0614(7) Uani 1 1 d . . . C14 C 0.4729(2) 0.8184(4) 0.35407(9) 0.0550(7) Uani 1 1 d . . . H14 H 0.4051 0.7115 0.3660 0.066 Uiso 1 1 calc R . . C15 C 0.5923(2) 1.1818(4) 0.36364(9) 0.0534(6) Uani 1 1 d . . . H15 H 0.6041 1.3218 0.3819 0.064 Uiso 1 1 calc R . . C16 C 1.1953(2) 1.1772(4) 0.07205(9) 0.0492(6) Uani 1 1 d . . . H16 H 1.2175 1.3181 0.0886 0.059 Uiso 1 1 calc R . . C17 C 0.8890(2) 0.7201(4) 0.13750(10) 0.0512(6) Uani 1 1 d . . . H17 H 0.8222 0.6161 0.1514 0.061 Uiso 1 1 calc R . . O2 O 1.2898(2) 0.8241(4) -0.04059(8) 0.0935(7) 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 O1 0.0665(10) 0.0518(10) 0.0550(10) -0.0107(8) 0.0124(8) 0.0013(8) C1 0.0417(12) 0.0350(12) 0.0446(12) -0.0006(11) 0.0000(9) 0.0020(10) C2 0.0476(13) 0.0422(14) 0.0432(13) -0.0029(11) 0.0018(10) 0.0047(11) C3 0.0493(13) 0.0371(14) 0.0396(12) 0.0021(10) -0.0025(10) 0.0050(10) C4 0.0451(13) 0.0376(13) 0.0493(14) -0.0007(11) 0.0003(10) 0.0030(10) C5 0.0576(14) 0.0378(13) 0.0528(15) 0.0001(11) 0.0008(11) -0.0005(11) C6 0.0548(13) 0.0415(14) 0.0535(15) -0.0005(12) -0.0001(12) -0.0090(11) C7 0.0510(13) 0.0428(15) 0.0575(14) -0.0036(12) 0.0052(11) -0.0010(11) C8 0.0488(13) 0.0328(13) 0.0507(14) -0.0031(10) 0.0007(11) 0.0007(10) C9 0.0512(14) 0.0407(14) 0.0544(15) 0.0006(12) 0.0053(11) -0.0043(10) C10 0.0567(14) 0.0336(13) 0.0606(15) -0.0093(12) 0.0008(12) -0.0030(11) C11 0.0525(14) 0.0587(16) 0.0532(15) -0.0038(13) 0.0070(11) 0.0063(12) C12 0.0603(15) 0.0579(17) 0.0579(16) 0.0077(13) 0.0125(12) -0.0037(12) C13 0.0657(16) 0.068(2) 0.0520(16) -0.0034(14) 0.0137(13) 0.0086(14) C14 0.0542(14) 0.0552(16) 0.0559(16) 0.0051(13) 0.0066(12) -0.0099(12) C15 0.0613(14) 0.0413(14) 0.0575(16) -0.0082(12) 0.0013(12) 0.0021(12) C16 0.0517(13) 0.0408(13) 0.0549(15) 0.0019(12) 0.0008(11) -0.0014(11) C17 0.0479(13) 0.0421(14) 0.0640(16) -0.0006(12) 0.0070(11) -0.0080(11) O2 0.1044(15) 0.1034(16) 0.0763(13) -0.0199(12) 0.0403(12) 0.0018(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.372(2) . ? O1 C13 1.375(3) . ? C1 C8 1.390(3) . ? C1 C2 1.392(3) . ? C1 C16 1.438(3) . ? C2 C10 1.383(3) . ? C3 C6 1.392(3) . ? C3 C9 1.399(3) . ? C3 C5 1.455(3) . ? C4 C8 1.383(3) . ? C4 C17 1.408(3) . ? C4 C7 1.467(3) . ? C5 C7 1.312(3) . ? C6 C14 1.372(3) . ? C9 C15 1.370(3) . ? C10 C17 1.367(3) . ? C11 C14 1.378(3) . ? C11 C15 1.383(3) . ? C12 C16 1.331(3) . ? C12 C13 1.446(3) . ? C13 O2 1.197(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 C2 O1 C13 121.80(18) . . ? C8 C1 C2 118.17(19) . . ? C8 C1 C16 124.4(2) . . ? C2 C1 C16 117.46(19) . . ? O1 C2 C10 117.18(19) . . ? O1 C2 C1 121.30(19) . . ? C10 C2 C1 121.5(2) . . ? C6 C3 C9 117.29(19) . . ? C6 C3 C5 119.0(2) . . ? C9 C3 C5 123.7(2) . . ? C8 C4 C17 117.40(19) . . ? C8 C4 C7 120.3(2) . . ? C17 C4 C7 122.3(2) . . ? C7 C5 C3 128.7(2) . . ? C14 C6 C3 121.7(2) . . ? C5 C7 C4 127.3(2) . . ? C4 C8 C1 122.0(2) . . ? C15 C9 C3 121.0(2) . . ? C17 C10 C2 118.8(2) . . ? C14 C11 C15 119.4(2) . . ? C16 C12 C13 121.4(2) . . ? O2 C13 O1 116.7(2) . . ? O2 C13 C12 126.1(2) . . ? O1 C13 C12 117.2(2) . . ? C6 C14 C11 120.1(2) . . ? C9 C15 C11 120.6(2) . . ? C12 C16 C1 120.8(2) . . ? C10 C17 C4 122.1(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 22.53 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.143 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.046 _chemical_compound_source synthetic _exptl_crystal_recrystallization_method Evaporation #END data_4u7s_trans _database_code_depnum_ccdc_archive 'CCDC 611808' _audit_creation_method SHELXL-97 _chemical_name_systematic trans-7-styrylcoumarin _chemical_name_common ? _chemical_melting_point 206-208C _chemical_formula_moiety 'C17 H12 O2' _chemical_formula_sum 'C17 H12 O2' _chemical_formula_weight 248.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c 21 b' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, y, z+1/2' 'x, y+1/2, -z+1/2' _cell_length_a 5.706(5) _cell_length_b 7.743(5) _cell_length_c 27.906(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 1232.9(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 172 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 22.4 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 877 _diffrn_reflns_av_R_equivalents 0.0121 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 22.47 _reflns_number_total 845 _reflns_number_gt 610 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -4(6) _refine_ls_number_reflns 845 _refine_ls_number_parameters 172 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0993 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.2282 _refine_ls_wR_factor_gt 0.1456 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.981 _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 O1 O 0.7531(9) 0.4271(9) 0.20236(17) 0.0443(15) Uani 1 1 d . . . O2 O 0.8477(11) 0.5094(11) 0.2751(2) 0.064(2) Uani 1 1 d . . . C3 C 0.3958(13) 0.2722(11) 0.1872(3) 0.041(2) Uani 1 1 d . . . C4 C 0.6021(12) 0.3455(10) 0.1711(3) 0.036(2) Uani 1 1 d . . . C5 C 0.4884(15) 0.3598(13) 0.2663(3) 0.048(2) Uani 1 1 d . . . H5 H 0.4518 0.3653 0.2987 0.057 Uiso 1 1 calc R . . C6 C 0.2508(13) 0.1951(12) 0.1527(3) 0.044(2) Uani 1 1 d . . . H6 H 0.1070 0.1498 0.1621 0.053 Uiso 1 1 calc R . . C7 C 0.6680(13) 0.3412(11) 0.1233(3) 0.0391(19) Uani 1 1 d . . . H7 H 0.8081 0.3922 0.1138 0.047 Uiso 1 1 calc R . . C8 C 0.5291(14) 0.2626(10) 0.0899(3) 0.039(2) Uani 1 1 d . . . C9 C 0.3412(14) 0.2799(12) 0.2366(3) 0.045(2) Uani 1 1 d . . . H9 H 0.2044 0.2299 0.2483 0.053 Uiso 1 1 calc R . . C10 C 0.8578(15) 0.2832(11) -0.0318(3) 0.044(2) Uani 1 1 d . . . C11 C 0.7292(15) 0.1894(13) -0.0642(3) 0.051(2) Uani 1 1 d . . . H11 H 0.5937 0.1331 -0.0543 0.061 Uiso 1 1 calc R . . C12 C 1.0674(15) 0.3563(12) -0.0470(4) 0.055(3) Uani 1 1 d . . . H12 H 1.1619 0.4155 -0.0254 0.065 Uiso 1 1 calc R . . C13 C 0.5934(14) 0.2444(11) 0.0399(3) 0.044(2) Uani 1 1 d . . . H13 H 0.4891 0.1844 0.0205 0.052 Uiso 1 1 calc R . . C14 C 0.7887(15) 0.3053(12) 0.0188(3) 0.049(2) Uani 1 1 d . . . H14 H 0.8908 0.3680 0.0381 0.059 Uiso 1 1 calc R . . C15 C 0.3166(16) 0.1850(12) 0.1053(3) 0.048(2) Uani 1 1 d . . . H15 H 0.2218 0.1274 0.0834 0.057 Uiso 1 1 calc R . . C16 C 0.7038(14) 0.4384(14) 0.2496(3) 0.048(2) Uani 1 1 d . . . C17 C 0.799(2) 0.1782(15) -0.1111(3) 0.062(3) Uani 1 1 d . . . H17 H 0.7067 0.1184 -0.1329 0.074 Uiso 1 1 calc R . . C18 C 1.1345(16) 0.3407(13) -0.0940(4) 0.055(2) Uani 1 1 d . . . H18 H 1.2740 0.3916 -0.1038 0.066 Uiso 1 1 calc R . . C19 C 1.0051(19) 0.2543(13) -0.1263(4) 0.058(2) Uani 1 1 d . . . H19 H 1.0528 0.2460 -0.1581 0.069 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.039(3) 0.049(3) 0.045(3) -0.004(3) -0.004(3) -0.006(3) O2 0.050(4) 0.074(5) 0.069(4) -0.017(4) -0.016(3) -0.010(4) C3 0.038(5) 0.033(4) 0.050(5) -0.003(4) 0.000(4) 0.004(4) C4 0.026(4) 0.032(4) 0.050(5) 0.002(4) -0.008(3) 0.001(4) C5 0.044(5) 0.052(6) 0.047(5) 0.000(4) 0.005(4) 0.007(5) C6 0.030(4) 0.048(5) 0.054(5) 0.009(4) 0.002(4) 0.001(4) C7 0.029(4) 0.040(5) 0.049(5) 0.002(4) -0.002(4) -0.004(4) C8 0.042(4) 0.037(4) 0.038(4) 0.008(4) 0.000(4) 0.003(4) C9 0.035(4) 0.045(5) 0.054(6) 0.002(4) 0.004(4) -0.001(4) C10 0.044(5) 0.032(4) 0.057(5) -0.002(4) -0.003(4) 0.004(4) C11 0.046(5) 0.052(5) 0.053(5) 0.005(5) -0.010(4) -0.012(5) C12 0.039(5) 0.047(5) 0.077(7) 0.003(5) -0.002(5) -0.003(5) C13 0.034(4) 0.043(5) 0.053(5) -0.002(4) -0.009(4) 0.004(4) C14 0.043(5) 0.045(6) 0.060(5) 0.005(5) 0.000(4) 0.004(5) C15 0.046(5) 0.038(5) 0.059(6) -0.002(4) -0.006(4) -0.004(5) C16 0.047(4) 0.047(5) 0.050(4) 0.001(5) -0.002(5) 0.000(5) C17 0.087(8) 0.054(6) 0.046(5) -0.004(5) 0.004(5) -0.012(7) C18 0.046(5) 0.052(6) 0.066(6) -0.004(5) 0.013(5) -0.002(5) C19 0.070(6) 0.049(5) 0.054(5) 0.009(5) 0.008(5) 0.007(5) _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 C16 1.350(11) . ? O1 C4 1.380(9) . ? O2 C16 1.219(10) . ? C3 C4 1.382(10) . ? C3 C6 1.402(12) . ? C3 C9 1.416(11) . ? C4 C7 1.386(10) . ? C5 C9 1.331(11) . ? C5 C16 1.449(13) . ? C6 C15 1.378(12) . ? C7 C8 1.365(11) . ? C8 C15 1.420(13) . ? C8 C13 1.449(11) . ? C10 C11 1.373(12) . ? C10 C12 1.390(12) . ? C10 C14 1.475(12) . ? C11 C17 1.370(12) . ? C12 C18 1.372(13) . ? C13 C14 1.346(12) . ? C17 C19 1.382(16) . ? C18 C19 1.344(14) . ? 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 C16 O1 C4 121.1(6) . . ? C4 C3 C6 117.0(7) . . ? C4 C3 C9 119.2(7) . . ? C6 C3 C9 123.8(7) . . ? O1 C4 C3 120.9(7) . . ? O1 C4 C7 116.8(6) . . ? C3 C4 C7 122.3(7) . . ? C9 C5 C16 122.1(8) . . ? C15 C6 C3 121.5(7) . . ? C8 C7 C4 120.6(7) . . ? C7 C8 C15 118.6(7) . . ? C7 C8 C13 123.5(7) . . ? C15 C8 C13 117.8(7) . . ? C5 C9 C3 119.1(7) . . ? C11 C10 C12 118.3(8) . . ? C11 C10 C14 123.3(8) . . ? C12 C10 C14 118.3(9) . . ? C17 C11 C10 120.5(9) . . ? C18 C12 C10 119.8(9) . . ? C14 C13 C8 126.7(8) . . ? C13 C14 C10 126.9(9) . . ? C6 C15 C8 119.9(8) . . ? O2 C16 O1 117.4(8) . . ? O2 C16 C5 124.9(9) . . ? O1 C16 C5 117.6(8) . . ? C11 C17 C19 121.0(10) . . ? C19 C18 C12 122.2(9) . . ? C18 C19 C17 118.2(9) . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 22.47 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.397 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.104 #END