# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Antony J. Fairbanks' 'David J. Chambers' 'Graham R. Evans' 'H.Y. Godage' _publ_contact_author_name 'Dr Antony J Fairbanks' _publ_contact_author_address ; Dyson Perrins Laboratory Oxford University South Parks Road Oxford OX1 3QY UNITED KINGDOM ; _publ_contact_author_email ANTONY.FAIRBANKS@CHEM.OX.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Stereoselective synthesis of C-glycosides from carboxylic acids: the tandem Tebbe/Claisen approach ; data_CRYSTALS_cif_a _database_code_CSD 212630 #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point 'not measured' _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _chemical_absolute_configuration syn #============================================================= _cell_length_a 8.4698(2) _cell_angle_alpha 90 _cell_length_b 6.4952(2) _cell_angle_beta 94.0089(6) _cell_length_c 20.0695(4) _cell_angle_gamma 90 _cell_volume 1101.38(5) _symmetry_cell_setting 'Monoclinic ' _symmetry_space_group_name_H-M 'P 1 21 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'Si ' 0.0720 0.0710 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937 1.1407 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C22 H32 O4 Si1 ' _chemical_formula_moiety ' C22 H32 O4 Si1 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 388.58 _cell_measurement_reflns_used 10755 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 2 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.36 _exptl_crystal_density_diffrn 1.172 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 420.248 _exptl_absorpt_coefficient_mu 0.129 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 10755 _reflns_number_total 2712 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_gt 2140 _diffrn_reflns_theta_min 5.10 _diffrn_reflns_theta_max 27.44 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _refine_diff_density_min -0.14 _refine_diff_density_max 0.14 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 2140 _refine_ls_number_parameters 245 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0373 _refine_ls_goodness_of_fit_ref 1.0489 _refine_ls_shift/su_max 0.006034 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 2.63 -1.35 1.79 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 0.0341(2) 0.2339(3) 0.30953(9) 0.0318 1.0000 Uani C1 0.0207(3) 0.1308(4) 0.37227(12) 0.0277 1.0000 Uani C2 0.0265(3) -0.0994(4) 0.36526(12) 0.0280 1.0000 Uani C3 0.0582(3) -0.1930(4) 0.30877(12) 0.0285 1.0000 Uani C4 0.1006(2) -0.0725(4) 0.24961(11) 0.0256 1.0000 Uani C5 0.1527(3) 0.1429(4) 0.27129(12) 0.0287 1.0000 Uani C6 0.1742(3) 0.2828(4) 0.21254(14) 0.0368 1.0000 Uani O2 0.2790(2) 0.1942(3) 0.16808(9) 0.0389 1.0000 Uani Si1 0.31894(7) -0.05233(13) 0.15984(3) 0.0266 1.0000 Uani O3 0.22637(19) -0.1739(3) 0.21786(8) 0.0281 1.0000 Uani C7 -0.1365(3) 0.1956(4) 0.39793(14) 0.0339 1.0000 Uani C8 -0.1394(3) 0.4125(4) 0.42510(11) 0.0268 1.0000 Uani O4 -0.0210(2) 0.4861(3) 0.45337(9) 0.0350 1.0000 Uani C9 -0.2932(3) 0.5278(4) 0.42094(11) 0.0293 1.0000 Uani C10 -0.4270(3) 0.4626(5) 0.38277(13) 0.0425 1.0000 Uani C11 -0.5649(4) 0.5783(6) 0.38004(16) 0.0543 1.0000 Uani C12 -0.5714(4) 0.7590(5) 0.41639(15) 0.0453 1.0000 Uani C13 -0.4395(3) 0.8242(4) 0.45507(14) 0.0378 1.0000 Uani C14 -0.3005(3) 0.7104(4) 0.45757(12) 0.0298 1.0000 Uani C15 0.2357(3) -0.1348(4) 0.07438(12) 0.0322 1.0000 Uani C16 0.0543(3) -0.1209(6) 0.07424(15) 0.0520 1.0000 Uani C17 0.2885(4) 0.0081(6) 0.01945(14) 0.0529 1.0000 Uani C18 0.2791(4) -0.3570(5) 0.05846(15) 0.0464 1.0000 Uani C19 0.5382(3) -0.0944(5) 0.18015(13) 0.0406 1.0000 Uani C20 0.6350(4) -0.0037(8) 0.12572(17) 0.0669 1.0000 Uani C21 0.5760(4) -0.3234(7) 0.18993(18) 0.0630 1.0000 Uani C22 0.5837(4) 0.0193(7) 0.24610(15) 0.0585 1.0000 Uani H11 0.1119 0.1700 0.4041 0.0335 1.0000 Uiso H21 0.0056 -0.1861 0.4049 0.0339 1.0000 Uiso H31 0.0535 -0.3466 0.3061 0.0344 1.0000 Uiso H41 0.0059 -0.0625 0.2171 0.0308 1.0000 Uiso H51 0.2562 0.1283 0.2980 0.0348 1.0000 Uiso H61 0.2188 0.4172 0.2293 0.0449 1.0000 Uiso H62 0.0690 0.3066 0.1880 0.0449 1.0000 Uiso H71 -0.1618 0.0989 0.4344 0.0411 1.0000 Uiso H72 -0.2197 0.1845 0.3602 0.0411 1.0000 Uiso H101 -0.4239 0.3311 0.3570 0.0504 1.0000 Uiso H111 -0.6600 0.5311 0.3517 0.0641 1.0000 Uiso H121 -0.6711 0.8418 0.4147 0.0541 1.0000 Uiso H131 -0.4443 0.9544 0.4815 0.0458 1.0000 Uiso H141 -0.2055 0.7590 0.4856 0.0360 1.0000 Uiso H161 0.0058 -0.1637 0.0295 0.0620 1.0000 Uiso H162 0.0164 -0.2141 0.1094 0.0620 1.0000 Uiso H163 0.0230 0.0240 0.0837 0.0620 1.0000 Uiso H171 0.2421 -0.0406 -0.0250 0.0634 1.0000 Uiso H172 0.4067 0.0068 0.0197 0.0634 1.0000 Uiso H173 0.2514 0.1514 0.0277 0.0634 1.0000 Uiso H181 0.2327 -0.3940 0.0128 0.0555 1.0000 Uiso H182 0.3969 -0.3710 0.0600 0.0555 1.0000 Uiso H183 0.2362 -0.4514 0.0922 0.0555 1.0000 Uiso H201 0.7502 -0.0278 0.1375 0.0808 1.0000 Uiso H202 0.6145 0.1477 0.1220 0.0808 1.0000 Uiso H203 0.6037 -0.0715 0.0821 0.0808 1.0000 Uiso H211 0.6923 -0.3411 0.2006 0.0748 1.0000 Uiso H212 0.5171 -0.3785 0.2276 0.0748 1.0000 Uiso H213 0.5432 -0.4001 0.1480 0.0748 1.0000 Uiso H221 0.6993 0.0001 0.2583 0.0699 1.0000 Uiso H222 0.5213 -0.0379 0.2823 0.0699 1.0000 Uiso H223 0.5601 0.1694 0.2404 0.0699 1.0000 Uiso 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 0.0393(9) 0.0239(9) 0.0334(9) 0.0007(7) 0.0110(7) 0.0075(8) C1 0.0278(11) 0.0277(12) 0.0282(11) -0.002(1) 0.0057(9) 0.002(1) C2 0.0277(11) 0.0263(13) 0.0307(11) 0.0045(9) 0.0071(9) 0.0025(9) C3 0.0268(11) 0.0251(11) 0.0341(12) -0.001(1) 0.006(1) 0.0019(9) C4 0.025(1) 0.0215(11) 0.030(1) -0.001(1) 0.0045(8) 0.005(1) C5 0.0310(12) 0.0237(12) 0.0323(12) -0.004(1) 0.0089(9) 0.001(1) C6 0.0498(15) 0.0244(12) 0.0382(14) 0.000(1) 0.0163(12) 0.0049(11) O2 0.0546(11) 0.0253(9) 0.040(1) -0.0014(8) 0.0222(8) 0.0004(8) Si1 0.0266(3) 0.0277(3) 0.0259(3) -0.0022(3) 0.0046(2) 0.0003(3) O3 0.0315(8) 0.0237(8) 0.0301(8) -0.0005(7) 0.0092(7) 0.0043(7) C7 0.0320(12) 0.0254(12) 0.0455(14) -0.0059(11) 0.0113(11) -0.001(1) C8 0.0315(11) 0.0257(13) 0.024(1) 0.0010(9) 0.0063(9) 0.002(1) O4 0.0345(9) 0.0306(11) 0.0395(9) -0.0043(8) 0.0000(7) 0.0029(8) C9 0.0340(12) 0.0286(12) 0.0261(11) -0.0006(9) 0.0068(9) 0.002(1) C10 0.0429(14) 0.0425(16) 0.0408(13) -0.0099(14) -0.008(1) 0.0094(14) C11 0.0456(17) 0.062(2) 0.0526(17) -0.0133(17) -0.0161(14) 0.0161(16) C12 0.0416(15) 0.0473(18) 0.0464(16) 0.0034(14) -0.0000(12) 0.0167(14) C13 0.0406(14) 0.0318(14) 0.0419(13) 0.0009(11) 0.0106(11) 0.0059(12) C14 0.0319(11) 0.0262(12) 0.0319(11) 0.000(1) 0.008(1) -0.0013(11) C15 0.0344(13) 0.0354(13) 0.0270(11) -0.002(1) 0.0023(9) 0.0027(11) C16 0.0339(14) 0.078(3) 0.0430(15) -0.0132(16) -0.0052(12) 0.0037(15) C17 0.067(2) 0.059(2) 0.0327(13) 0.0099(13) 0.0011(13) -0.0055(17) C18 0.0585(17) 0.0426(16) 0.0377(15) -0.0132(13) -0.0002(12) 0.0031(15) C19 0.0292(12) 0.059(2) 0.0340(12) -0.0042(13) 0.003(1) 0.0014(13) C20 0.0297(13) 0.115(4) 0.0574(18) -0.001(2) 0.0129(12) -0.0121(19) C21 0.0507(18) 0.079(3) 0.058(2) -0.0046(19) -0.0100(15) 0.0277(19) C22 0.0361(15) 0.094(3) 0.0445(16) -0.0183(18) -0.0023(12) -0.0101(17) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.438(3) yes O1 . C5 . 1.433(3) yes C1 . C2 . 1.503(3) yes C1 . C7 . 1.520(3) yes C1 . H11 . 1.000 no C2 . C3 . 1.330(3) yes C2 . H21 . 1.000 no C3 . C4 . 1.487(3) yes C3 . H31 . 1.000 no C4 . C5 . 1.522(3) yes C4 . O3 . 1.439(3) yes C4 . H41 . 1.000 no C5 . C6 . 1.509(4) yes C5 . H51 . 1.000 no C6 . O2 . 1.423(3) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no O2 . Si1 . 1.648(2) yes Si1 . O3 . 1.6499(17) yes Si1 . C15 . 1.886(3) yes Si1 . C19 . 1.893(3) yes C7 . C8 . 1.511(3) yes C7 . H71 . 1.000 no C7 . H72 . 1.000 no C8 . O4 . 1.215(3) yes C8 . C9 . 1.499(3) yes C9 . C10 . 1.389(4) yes C9 . C14 . 1.399(3) yes C10 . C11 . 1.387(4) yes C10 . H101 . 1.000 no C11 . C12 . 1.385(5) yes C11 . H111 . 1.000 no C12 . C13 . 1.381(4) yes C12 . H121 . 1.000 no C13 . C14 . 1.388(4) yes C13 . H131 . 1.000 no C14 . H141 . 1.000 no C15 . C16 . 1.539(4) yes C15 . C17 . 1.532(4) yes C15 . C18 . 1.529(4) yes C16 . H161 . 1.000 no C16 . H162 . 1.000 no C16 . H163 . 1.000 no C17 . H171 . 1.000 no C17 . H172 . 1.000 no C17 . H173 . 1.000 no C18 . H181 . 1.000 no C18 . H182 . 1.000 no C18 . H183 . 1.000 no C19 . C20 . 1.530(4) yes C19 . C21 . 1.531(5) yes C19 . C22 . 1.541(4) yes C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.000 no C21 . H211 . 1.000 no C21 . H212 . 1.000 no C21 . H213 . 1.000 no C22 . H221 . 1.000 no C22 . H222 . 1.000 no C22 . H223 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 112.24(18) yes O1 . C1 . C2 . 112.10(19) yes O1 . C1 . C7 . 107.0(2) yes C2 . C1 . C7 . 110.1(2) yes O1 . C1 . H11 . 109.6 no C2 . C1 . H11 . 106.5 no C7 . C1 . H11 . 111.6 no C1 . C2 . C3 . 123.0(2) yes C1 . C2 . H21 . 118.5 no C3 . C2 . H21 . 118.5 no C2 . C3 . C4 . 121.0(2) yes C2 . C3 . H31 . 119.5 no C4 . C3 . H31 . 119.5 no C3 . C4 . C5 . 109.68(19) yes C3 . C4 . O3 . 109.91(19) yes C5 . C4 . O3 . 109.79(18) yes C3 . C4 . H41 . 109.1 no C5 . C4 . H41 . 109.3 no O3 . C4 . H41 . 109.04 no O1 . C5 . C4 . 109.40(18) yes O1 . C5 . C6 . 107.32(19) yes C4 . C5 . C6 . 112.2(2) yes O1 . C5 . H51 . 111.9 no C4 . C5 . H51 . 107.0 no C6 . C5 . H51 . 109.1 no C5 . C6 . O2 . 111.2(2) yes C5 . C6 . H61 . 109.0 no O2 . C6 . H61 . 109.0 no C5 . C6 . H62 . 109.0 no O2 . C6 . H62 . 109.0 no H61 . C6 . H62 . 109.5 no C6 . O2 . Si1 . 126.67(16) yes O2 . Si1 . O3 . 106.46(9) yes O2 . Si1 . C15 . 107.52(12) yes O3 . Si1 . C15 . 109.88(11) yes O2 . Si1 . C19 . 108.91(13) yes O3 . Si1 . C19 . 106.63(11) yes C15 . Si1 . C19 . 116.98(12) yes C4 . O3 . Si1 . 119.79(14) yes C1 . C7 . C8 . 114.7(2) yes C1 . C7 . H71 . 108.2 no C8 . C7 . H71 . 108.2 no C1 . C7 . H72 . 108.2 no C8 . C7 . H72 . 108.2 no H71 . C7 . H72 . 109.5 no C7 . C8 . O4 . 120.1(2) yes C7 . C8 . C9 . 118.8(2) yes O4 . C8 . C9 . 121.0(2) yes C8 . C9 . C10 . 123.4(2) yes C8 . C9 . C14 . 117.7(2) yes C10 . C9 . C14 . 118.9(2) yes C9 . C10 . C11 . 120.6(3) yes C9 . C10 . H101 . 119.7 no C11 . C10 . H101 . 119.7 no C10 . C11 . C12 . 120.2(3) yes C10 . C11 . H111 . 119.9 no C12 . C11 . H111 . 119.9 no C11 . C12 . C13 . 119.7(3) yes C11 . C12 . H121 . 120.1 no C13 . C12 . H121 . 120.1 no C12 . C13 . C14 . 120.5(3) yes C12 . C13 . H131 . 119.7 no C14 . C13 . H131 . 119.7 no C9 . C14 . C13 . 120.1(2) yes C9 . C14 . H141 . 120.0 no C13 . C14 . H141 . 120.0 no Si1 . C15 . C16 . 107.15(18) yes Si1 . C15 . C17 . 111.9(2) yes C16 . C15 . C17 . 107.8(3) yes Si1 . C15 . C18 . 112.21(19) yes C16 . C15 . C18 . 108.0(3) yes C17 . C15 . C18 . 109.6(2) yes C15 . C16 . H161 . 109.5 no C15 . C16 . H162 . 109.5 no H161 . C16 . H162 . 109.5 no C15 . C16 . H163 . 109.5 no H161 . C16 . H163 . 109.5 no H162 . C16 . H163 . 109.5 no C15 . C17 . H171 . 109.5 no C15 . C17 . H172 . 109.5 no H171 . C17 . H172 . 109.5 no C15 . C17 . H173 . 109.5 no H171 . C17 . H173 . 109.5 no H172 . C17 . H173 . 109.5 no C15 . C18 . H181 . 109.5 no C15 . C18 . H182 . 109.5 no H181 . C18 . H182 . 109.5 no C15 . C18 . H183 . 109.5 no H181 . C18 . H183 . 109.5 no H182 . C18 . H183 . 109.5 no Si1 . C19 . C20 . 111.0(2) yes Si1 . C19 . C21 . 111.2(2) yes C20 . C19 . C21 . 110.4(3) yes Si1 . C19 . C22 . 107.38(19) yes C20 . C19 . C22 . 108.3(3) yes C21 . C19 . C22 . 108.5(3) yes C19 . C20 . H201 . 109.5 no C19 . C20 . H202 . 109.5 no H201 . C20 . H202 . 109.5 no C19 . C20 . H203 . 109.5 no H201 . C20 . H203 . 109.5 no H202 . C20 . H203 . 109.5 no C19 . C21 . H211 . 109.5 no C19 . C21 . H212 . 109.5 no H211 . C21 . H212 . 109.5 no C19 . C21 . H213 . 109.5 no H211 . C21 . H213 . 109.5 no H212 . C21 . H213 . 109.5 no C19 . C22 . H221 . 109.5 no C19 . C22 . H222 . 109.5 no H221 . C22 . H222 . 109.5 no C19 . C22 . H223 . 109.5 no H221 . C22 . H223 . 109.5 no H222 . C22 . H223 . 109.5 no data_CRYSTALS_cif_b _database_code_CSD 212631 #========================================================================== # Diffractometer details #========================================================================== _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #========================================================================== # General computing #========================================================================== _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point 'not measured' _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _chemical_absolute_configuration syn #============================================================= _cell_length_a 5.8009(2) _cell_angle_alpha 90 _cell_length_b 13.1214(4) _cell_angle_beta 90 _cell_length_c 18.5666(5) _cell_angle_gamma 90 _cell_volume 1413.2 _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 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C16 H18 O4 ' _chemical_formula_moiety ' C16 H18 O4 ' _chemical_compound_source ; synthesis as derscribed ; _chemical_formula_weight 274.32 _cell_measurement_reflns_used 8918 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 4 _exptl_crystal_description ' fragment ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 584.192 _exptl_absorpt_coefficient_mu 0.092 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 8918 _reflns_number_total 1868 # 1887 including systematic absences _diffrn_reflns_av_R_equivalents 0.031 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_gt 1552 _diffrn_reflns_theta_min 5.18 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min 0 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 17 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _refine_diff_density_min -0.14 _refine_diff_density_max 0.16 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 1552 _refine_ls_number_parameters 181 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0319 _refine_ls_goodness_of_fit_ref 1.0546 _refine_ls_shift/su_max 0.000275 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 0.414 0.130 0.146 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 0.1089(2) 0.56034(8) 0.21285(7) 0.0316 1.0000 Uani C1 -0.0830(3) 0.55814(13) 0.25579(9) 0.0289 1.0000 Uani C2 -0.1936(3) 0.47493(13) 0.27673(9) 0.0265 1.0000 Uani C3 -0.1239(3) 0.36966(12) 0.25271(8) 0.0227 1.0000 Uani C4 0.0297(3) 0.38268(11) 0.18710(8) 0.0202 1.0000 Uani C5 0.2134(3) 0.46244(12) 0.20167(8) 0.0228 1.0000 Uani C6 0.3719(3) 0.47161(12) 0.13731(9) 0.0270 1.0000 Uani O2 0.0103(2) 0.31739(9) 0.30687(6) 0.0256 1.0000 Uani C7 -0.1081(3) 0.27515(13) 0.36357(9) 0.0277 1.0000 Uani C8 -0.3347(4) 0.27511(16) 0.37274(11) 0.0366 1.0000 Uani C9 0.0595(4) 0.22681(16) 0.4137(1) 0.0395 1.0000 Uani O3 0.1394(2) 0.28900(8) 0.16784(6) 0.0209 1.0000 Uani O4 0.4618(2) 0.37206(8) 0.12054(6) 0.0252 1.0000 Uani C10 0.2811(3) 0.30267(12) 0.10573(8) 0.0219 1.0000 Uani C11 0.3814(3) 0.20055(12) 0.08589(8) 0.0216 1.0000 Uani C12 0.5910(3) 0.16712(13) 0.11327(9) 0.0280 1.0000 Uani C13 0.6738(3) 0.07085(13) 0.0952(1) 0.0301 1.0000 Uani C14 0.5478(3) 0.00860(13) 0.05014(9) 0.0290 1.0000 Uani C15 0.3392(3) 0.04161(13) 0.02232(9) 0.0313 1.0000 Uani C16 0.2571(3) 0.13784(13) 0.03987(8) 0.0269 1.0000 Uani H11 -0.1449 0.6251 0.2728 0.0347 1.0000 Uiso H21 -0.3287 0.4823 0.3098 0.0319 1.0000 Uiso H31 -0.2662 0.3289 0.2429 0.0272 1.0000 Uiso H41 -0.0706 0.4051 0.1463 0.0243 1.0000 Uiso H51 0.3013 0.4410 0.2455 0.0273 1.0000 Uiso H61 0.5019 0.5189 0.1489 0.0324 1.0000 Uiso H62 0.2840 0.4987 0.0951 0.0324 1.0000 Uiso H81 -0.4036 0.2420 0.4162 0.0439 1.0000 Uiso H82 -0.4368 0.3082 0.3362 0.0439 1.0000 Uiso H91 -0.0255 0.1959 0.4552 0.0475 1.0000 Uiso H92 0.1692 0.2796 0.4320 0.0475 1.0000 Uiso H93 0.1472 0.1725 0.3877 0.0475 1.0000 Uiso H101 0.1869 0.3308 0.0652 0.0263 1.0000 Uiso H121 0.6824 0.2122 0.1460 0.0336 1.0000 Uiso H131 0.8247 0.0468 0.1150 0.0362 1.0000 Uiso H141 0.6073 -0.0607 0.0375 0.0348 1.0000 Uiso H151 0.2480 -0.0037 -0.0103 0.0375 1.0000 Uiso H161 0.1076 0.1621 0.0192 0.0323 1.0000 Uiso 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 0.0372(7) 0.0188(5) 0.0388(7) -0.0020(5) 0.0072(6) 0.0008(6) C1 0.032(1) 0.0268(8) 0.0277(8) -0.0053(7) -0.0004(8) 0.0057(8) C2 0.0251(8) 0.0313(8) 0.0233(7) -0.0056(7) 0.0000(7) 0.0052(7) C3 0.0200(7) 0.0256(7) 0.0223(7) -0.0010(6) -0.0008(7) 0.0015(7) C4 0.0211(8) 0.0193(7) 0.0202(7) -0.0018(6) -0.0007(6) 0.0041(6) C5 0.0253(8) 0.0188(7) 0.0243(7) -0.0006(6) 0.0001(7) 0.0009(7) C6 0.0304(9) 0.0208(7) 0.0297(8) 0.0011(6) 0.0035(8) -0.0022(7) O2 0.0245(6) 0.0297(6) 0.0224(5) 0.0050(5) 0.0024(5) 0.0011(5) C7 0.0360(9) 0.0253(8) 0.0218(7) 0.0006(6) 0.0058(7) -0.0037(8) C8 0.0366(11) 0.0372(9) 0.036(1) 0.0023(8) 0.0145(9) -0.0014(9) C9 0.0456(12) 0.045(1) 0.0283(9) 0.0110(8) -0.0040(9) -0.009(1) O3 0.0225(5) 0.0191(5) 0.0212(5) -0.0002(4) 0.0034(5) 0.0010(5) O4 0.0236(6) 0.0222(5) 0.0299(6) -0.0012(5) 0.0048(5) -0.0024(5) C10 0.0220(8) 0.0241(7) 0.0195(7) 0.0003(6) 0.0016(6) -0.0013(7) C11 0.0232(7) 0.0241(7) 0.0176(7) -0.0002(6) 0.0032(6) -0.0002(7) C12 0.0254(9) 0.0299(8) 0.0287(8) -0.0050(7) -0.0029(7) 0.0017(7) C13 0.0275(9) 0.0308(8) 0.0320(8) 0.0003(7) 0.0013(8) 0.0056(8) C14 0.037(1) 0.0244(8) 0.0257(8) -0.0004(7) 0.0079(8) 0.0026(8) C15 0.038(1) 0.0288(8) 0.0272(8) -0.0051(7) -0.0025(8) -0.0036(8) C16 0.0263(8) 0.0301(8) 0.0243(8) -0.0006(7) -0.0026(7) 0.0004(8) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.369(2) yes O1 . C5 . 1.4355(19) yes C1 . C2 . 1.325(3) yes C1 . H11 . 1.0000 no C2 . C3 . 1.507(2) yes C2 . H21 . 1.0000 no C3 . C4 . 1.519(2) yes C3 . O2 . 1.4448(19) yes C3 . H31 . 1.0000 no C4 . C5 . 1.518(2) yes C4 . O3 . 1.4295(17) yes C4 . H41 . 1.0000 no C5 . C6 . 1.513(2) yes C5 . H51 . 1.0000 no C6 . O4 . 1.440(2) yes C6 . H61 . 1.0000 no C6 . H62 . 1.0000 no O2 . C7 . 1.3737(19) yes C7 . C8 . 1.326(3) yes C7 . C9 . 1.488(3) yes C8 . H81 . 1.0000 no C8 . H82 . 1.000 no C9 . H91 . 1.0000 no C9 . H92 . 1.000 no C9 . H93 . 1.000 no O3 . C10 . 1.4277(18) yes O4 . C10 . 1.4153(19) yes C10 . C11 . 1.506(2) yes C10 . H101 . 1.0000 no C11 . C12 . 1.389(2) yes C11 . C16 . 1.388(2) yes C12 . C13 . 1.392(2) yes C12 . H121 . 1.0000 no C13 . C14 . 1.380(3) yes C13 . H131 . 1.0000 no C14 . C15 . 1.385(3) yes C14 . H141 . 1.0000 no C15 . C16 . 1.388(2) yes C15 . H151 . 1.0000 no C16 . H161 . 1.0000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 114.12(12) yes O1 . C1 . C2 . 125.58(15) yes O1 . C1 . H11 . 117.21 no C2 . C1 . H11 . 117.21 no C1 . C2 . C3 . 122.60(16) yes C1 . C2 . H21 . 118.70 no C3 . C2 . H21 . 118.70 no C2 . C3 . C4 . 106.95(13) yes C2 . C3 . O2 . 111.95(13) yes C4 . C3 . O2 . 107.19(13) yes C2 . C3 . H31 . 108.80 no C4 . C3 . H31 . 113.43 no O2 . C3 . H31 . 108.57 no C3 . C4 . C5 . 110.27(12) yes C3 . C4 . O3 . 111.40(12) yes C5 . C4 . O3 . 108.97(13) yes C3 . C4 . H41 . 107.45 no C5 . C4 . H41 . 109.94 no O3 . C4 . H41 . 108.78 no O1 . C5 . C4 . 110.26(13) yes O1 . C5 . C6 . 107.45(13) yes C4 . C5 . C6 . 109.93(13) yes O1 . C5 . H51 . 110.45 no C4 . C5 . H51 . 107.99 no C6 . C5 . H51 . 110.78 no C5 . C6 . O4 . 108.58(12) yes C5 . C6 . H61 . 109.69 no O4 . C6 . H61 . 109.69 no C5 . C6 . H62 . 109.69 no O4 . C6 . H62 . 109.69 no H61 . C6 . H62 . 109.47 no C3 . O2 . C7 . 117.10(13) yes O2 . C7 . C8 . 126.46(18) yes O2 . C7 . C9 . 108.98(16) yes C8 . C7 . C9 . 124.55(18) yes C7 . C8 . H81 . 120.0 no C7 . C8 . H82 . 120.00 no H81 . C8 . H82 . 120.0 no C7 . C9 . H91 . 109.47 no C7 . C9 . H92 . 109.47 no H91 . C9 . H92 . 109.48 no C7 . C9 . H93 . 109.47 no H91 . C9 . H93 . 109.48 no H92 . C9 . H93 . 109.5 no C4 . O3 . C10 . 110.51(11) yes C6 . O4 . C10 . 110.95(13) yes O3 . C10 . O4 . 110.51(12) yes O3 . C10 . C11 . 107.95(12) yes O4 . C10 . C11 . 109.50(13) yes O3 . C10 . H101 . 109.81 no O4 . C10 . H101 . 108.27 no C11 . C10 . H101 . 110.81 no C10 . C11 . C12 . 121.96(14) yes C10 . C11 . C16 . 118.50(15) yes C12 . C11 . C16 . 119.52(15) yes C11 . C12 . C13 . 120.05(16) yes C11 . C12 . H121 . 119.98 no C13 . C12 . H121 . 119.98 no C12 . C13 . C14 . 120.01(17) yes C12 . C13 . H131 . 119.99 no C14 . C13 . H131 . 120.00 no C13 . C14 . C15 . 120.27(16) yes C13 . C14 . H141 . 119.86 no C15 . C14 . H141 . 119.86 no C14 . C15 . C16 . 119.77(16) yes C14 . C15 . H151 . 120.11 no C16 . C15 . H151 . 120.11 no C11 . C16 . C15 . 120.36(16) yes C11 . C16 . H161 . 119.82 no C15 . C16 . H161 . 119.82 no data_CRYSTALS_cif_c _database_code_CSD 212632 #========================================================================== # Diffractometer details #========================================================================== _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #========================================================================== # General computing #========================================================================== _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point 'not measured' _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _chemical_absolute_structure syn #============================================================= _cell_length_a 5.1126(5) _cell_angle_alpha 90 _cell_length_b 14.2991(2) _cell_angle_beta 90 _cell_length_c 19.1347(8) _cell_angle_gamma 90 _cell_volume 1398.9 _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 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C16 H18 O4 ' _chemical_formula_moiety ' C16 H18 O4 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 274.32 _cell_measurement_reflns_used 14624 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 4 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 584.192 _exptl_absorpt_coefficient_mu 0.093 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 14624 _reflns_number_total 1864 # 1883 reflections including systematic absences _diffrn_reflns_av_R_equivalents 0.051 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_gt 1409 _diffrn_reflns_theta_min 5.11 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min 0 _reflns_limit_h_max 6 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _refine_diff_density_min -0.12 _refine_diff_density_max 0.16 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 1409 _refine_ls_number_parameters 181 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0355 _refine_ls_goodness_of_fit_ref 1.0410 _refine_ls_shift/su_max 0.006251 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 1.93 -.283 1.35 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 0.5687(3) 0.49206(8) 0.50672(7) 0.0339 1.0000 Uani O2 0.4229(3) 0.63930(9) 0.65736(7) 0.0314 1.0000 Uani O3 0.1682(3) 0.68820(9) 0.56237(6) 0.0340 1.0000 Uani O4 0.6036(3) 0.31054(11) 0.40798(8) 0.0446 1.0000 Uani C1 0.6563(5) 0.40683(13) 0.5392(1) 0.0348 1.0000 Uani C2 0.7283(5) 0.42047(15) 0.61479(11) 0.0403 1.0000 Uani C3 0.6958(4) 0.50038(15) 0.6489(1) 0.0373 1.0000 Uani C4 0.5828(4) 0.58271(13) 0.61198(9) 0.0292 1.0000 Uani C5 0.4136(4) 0.54760(12) 0.55242(9) 0.0291 1.0000 Uani C6 0.3041(5) 0.62998(13) 0.51296(9) 0.0363 1.0000 Uani C7 0.8835(4) 0.37254(14) 0.49530(12) 0.0395 1.0000 Uani C8 0.8080(4) 0.35067(13) 0.42082(11) 0.0354 1.0000 Uani C9 0.9959(5) 0.37810(16) 0.36458(13) 0.0493 1.0000 Uani C10 0.3345(4) 0.71712(13) 0.61857(9) 0.0298 1.0000 Uani C11 0.1717(4) 0.78227(13) 0.66245(9) 0.0293 1.0000 Uani C12 0.0125(5) 0.75114(15) 0.71608(11) 0.0394 1.0000 Uani C13 -0.1532(5) 0.81368(16) 0.7502(1) 0.0439 1.0000 Uani C14 -0.1593(5) 0.90688(15) 0.7304(1) 0.0391 1.0000 Uani C15 0.0003(5) 0.93788(14) 0.67716(11) 0.0373 1.0000 Uani C16 0.1663(4) 0.87603(13) 0.6434(1) 0.0331 1.0000 Uani H11 0.5132 0.3592 0.5406 0.0418 1.0000 Uiso H21 0.8048 0.3663 0.6407 0.0484 1.0000 Uiso H31 0.7470 0.5053 0.6992 0.0448 1.0000 Uiso H41 0.7308 0.6223 0.5948 0.0351 1.0000 Uiso H51 0.2666 0.5090 0.5713 0.0349 1.0000 Uiso H61 0.4494 0.6660 0.4906 0.0436 1.0000 Uiso H62 0.1801 0.6078 0.4761 0.0436 1.0000 Uiso H71 1.0215 0.4221 0.4948 0.0474 1.0000 Uiso H72 0.9552 0.3145 0.5172 0.0474 1.0000 Uiso H91 0.9231 0.3598 0.3180 0.0591 1.0000 Uiso H92 1.0237 0.4473 0.3659 0.0591 1.0000 Uiso H93 1.1666 0.3455 0.3722 0.0591 1.0000 Uiso H101 0.4959 0.7491 0.6012 0.0358 1.0000 Uiso H121 0.0163 0.6839 0.7303 0.0473 1.0000 Uiso H131 -0.2679 0.7912 0.7891 0.0527 1.0000 Uiso H141 -0.2792 0.9516 0.7547 0.0469 1.0000 Uiso H151 -0.0037 1.0051 0.6629 0.0447 1.0000 Uiso H161 0.2830 0.8990 0.6052 0.0397 1.0000 Uiso 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 0.0434(8) 0.0259(6) 0.0324(6) 0.0013(5) -0.0023(7) 0.0089(6) O2 0.0325(7) 0.0331(6) 0.0285(6) 0.0006(5) -0.0022(6) 0.0022(6) O3 0.0387(8) 0.0343(6) 0.0290(6) -0.0037(5) -0.0056(6) 0.0072(7) O4 0.0395(9) 0.0462(8) 0.0482(8) -0.0078(7) -0.0029(8) -0.0125(7) C1 0.0384(11) 0.0242(8) 0.042(1) 0.0034(8) -0.007(1) 0.0012(9) C2 0.0447(12) 0.035(1) 0.041(1) 0.0085(9) -0.008(1) 0.005(1) C3 0.0332(11) 0.045(1) 0.0342(9) 0.0061(9) -0.008(1) 0.004(1) C4 0.0267(9) 0.0304(8) 0.0306(9) -0.0001(7) -0.0021(8) -0.0015(8) C5 0.032(1) 0.0272(8) 0.0285(9) 0.0005(7) -0.0018(9) 0.0021(8) C6 0.0498(12) 0.0314(9) 0.0279(8) -0.0028(8) -0.004(1) 0.011(1) C7 0.0343(11) 0.0324(9) 0.0519(12) -0.005(1) -0.009(1) 0.0058(9) C8 0.0329(11) 0.0232(8) 0.0500(12) 0.0002(8) -0.005(1) 0.0033(9) C9 0.0418(12) 0.0441(11) 0.0619(14) -0.0017(11) 0.0024(12) -0.0047(11) C10 0.031(1) 0.0279(8) 0.0302(9) 0.0018(7) 0.0027(9) -0.0043(8) C11 0.030(1) 0.0325(8) 0.0259(8) -0.0029(7) -0.0014(9) -0.0036(9) C12 0.0460(12) 0.0360(9) 0.036(1) 0.0017(9) 0.0065(11) -0.004(1) C13 0.0469(13) 0.0512(11) 0.034(1) -0.0019(9) 0.010(1) -0.0008(12) C14 0.0360(11) 0.0482(11) 0.0331(9) -0.0096(9) -0.001(1) 0.005(1) C15 0.0378(11) 0.0347(9) 0.039(1) -0.0035(8) -0.002(1) 0.003(1) C16 0.035(1) 0.0330(9) 0.0314(9) -0.0004(8) 0.0021(9) -0.0026(9) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.439(2) yes O1 . C5 . 1.423(2) yes O2 . C4 . 1.441(2) yes O2 . C10 . 1.412(2) yes O3 . C6 . 1.439(2) yes O3 . C10 . 1.432(2) yes O4 . C8 . 1.218(3) yes C1 . C2 . 1.505(3) yes C1 . C7 . 1.515(3) yes C1 . H11 . 1.000 no C2 . C3 . 1.326(3) yes C2 . H21 . 1.000 no C3 . C4 . 1.489(3) yes C3 . H31 . 1.0000 no C4 . C5 . 1.516(2) yes C4 . H41 . 1.0000 no C5 . C6 . 1.507(2) yes C5 . H51 . 1.0000 no C6 . H61 . 1.000 no C6 . H62 . 1.000 no C7 . C8 . 1.509(3) yes C7 . H71 . 1.000 no C7 . H72 . 1.000 no C8 . C9 . 1.495(3) yes C9 . H91 . 1.000 no C9 . H92 . 1.000 no C9 . H93 . 1.000 no C10 . C11 . 1.505(3) yes C10 . H101 . 1.0000 no C11 . C12 . 1.383(3) yes C11 . C16 . 1.389(3) yes C12 . C13 . 1.395(3) yes C12 . H121 . 1.000 no C13 . C14 . 1.386(3) yes C13 . H131 . 1.000 no C14 . C15 . 1.379(3) yes C14 . H141 . 1.000 no C15 . C16 . 1.385(3) yes C15 . H151 . 1.000 no C16 . H161 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 112.35(14) yes C4 . O2 . C10 . 107.90(13) yes C6 . O3 . C10 . 111.96(16) yes O1 . C1 . C2 . 112.43(16) yes O1 . C1 . C7 . 105.83(16) yes C2 . C1 . C7 . 112.79(18) yes O1 . C1 . H11 . 111.17 no C2 . C1 . H11 . 103.97 no C7 . C1 . H11 . 110.79 no C1 . C2 . C3 . 123.59(18) yes C1 . C2 . H21 . 118.2 no C3 . C2 . H21 . 118.2 no C2 . C3 . C4 . 119.81(17) yes C2 . C3 . H31 . 120.1 no C4 . C3 . H31 . 120.1 no O2 . C4 . C3 . 112.24(15) yes O2 . C4 . C5 . 108.38(15) yes C3 . C4 . C5 . 108.39(16) yes O2 . C4 . H41 . 108.00 no C3 . C4 . H41 . 107.99 no C5 . C4 . H41 . 111.87 no O1 . C5 . C4 . 109.20(15) yes O1 . C5 . C6 . 109.60(14) yes C4 . C5 . C6 . 109.25(15) yes O1 . C5 . H51 . 109.49 no C4 . C5 . H51 . 109.85 no C6 . C5 . H51 . 109.44 no O3 . C6 . C5 . 107.61(15) yes O3 . C6 . H61 . 109.94 no C5 . C6 . H61 . 109.94 no O3 . C6 . H62 . 109.94 no C5 . C6 . H62 . 109.94 no H61 . C6 . H62 . 109.47 no C1 . C7 . C8 . 113.26(17) yes C1 . C7 . H71 . 108.52 no C8 . C7 . H71 . 108.52 no C1 . C7 . H72 . 108.52 no C8 . C7 . H72 . 108.52 no H71 . C7 . H72 . 109.47 no O4 . C8 . C7 . 120.5(2) yes O4 . C8 . C9 . 122.0(2) yes C7 . C8 . C9 . 117.47(19) yes C8 . C9 . H91 . 109.5 no C8 . C9 . H92 . 109.5 no H91 . C9 . H92 . 109.5 no C8 . C9 . H93 . 109.5 no H91 . C9 . H93 . 109.5 no H92 . C9 . H93 . 109.5 no O2 . C10 . O3 . 110.93(14) yes O2 . C10 . C11 . 111.82(15) yes O3 . C10 . C11 . 105.63(16) yes O2 . C10 . H101 . 105.70 no O3 . C10 . H101 . 111.89 no C11 . C10 . H101 . 111.00 no C10 . C11 . C12 . 122.68(17) yes C10 . C11 . C16 . 117.54(17) yes C12 . C11 . C16 . 119.53(18) yes C11 . C12 . C13 . 119.92(19) yes C11 . C12 . H121 . 120.0 no C13 . C12 . H121 . 120.0 no C12 . C13 . C14 . 120.1(2) yes C12 . C13 . H131 . 119.9 no C14 . C13 . H131 . 119.9 no C13 . C14 . C15 . 119.9(2) yes C13 . C14 . H141 . 120.1 no C15 . C14 . H141 . 120.1 no C14 . C15 . C16 . 120.10(18) yes C14 . C15 . H151 . 119.9 no C16 . C15 . H151 . 119.9 no C11 . C16 . C15 . 120.43(19) yes C11 . C16 . H161 . 119.79 no C15 . C16 . H161 . 119.78 no