Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 1048 loop_ _publ_author_name 'John David Holbrey' 'W.Matthew Reichert' R.D.Rogers 'Megan B.Turner' _publ_contact_author_name 'Dr John David Holbrey' _publ_contact_author_address ; Center for Green Manufacturing The University of Alabama Tuscaloosa Alabama 35487 UNITED STATES OF AMERICA ; _publ_contact_author_email JHOLBREY@BAMA.UA.EDU _publ_requested_journal 'Dalton Transactions' _publ_section_title ; New ionic liquids containing an appended hydroxyl functionality from the atom-efficient, one-pot reaction of 1-methylimidazole and acid with propylene oxide ; data_propyl _database_code_depnum_ccdc_archive 'CCDC 224058' _audit_creation_method SHELXL-97 _chemical_name_systematic '1-(2-hydroxypropyl)-3-methylimidazolium tetraphenylborate' _chemical_name_common ? _chemical_melting_point 411 _chemical_formula_moiety ? _chemical_formula_sum 'C31 H33 B N2 O' _chemical_formula_weight 460.40 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 10.771(3) _cell_length_b 11.201(3) _cell_length_c 11.612(4) _cell_angle_alpha 96.211(5) _cell_angle_beta 111.392(5) _cell_angle_gamma 94.957(5) _cell_volume 1284.6(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 941 _cell_measurement_theta_min 5.77 _cell_measurement_theta_max 46.44 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 1.50 _exptl_crystal_size_mid 0.70 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.190 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.53 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_probe ? _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ccd _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 5698 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 23.25 _reflns_number_total 3634 _reflns_number_gt 3103 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0856P)^2^+0.0701P] 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 0.045(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3634 _refine_ls_number_parameters 449 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1153 _refine_ls_wR_factor_gt 0.1097 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 B B 0.14065(17) 0.23359(16) 0.79326(17) 0.0323(4) Uani 1 1 d . . . N1 N 0.70217(12) 0.18367(11) 0.96850(12) 0.0352(3) Uani 1 1 d . . . N2 N 0.71168(13) 0.29170(11) 1.13809(12) 0.0364(3) Uani 1 1 d . . . O1 O 0.43838(12) 0.04933(11) 0.84045(11) 0.0431(3) Uani 1 1 d . . . H1A H 0.363(3) 0.077(2) 0.802(2) 0.095(9) Uiso 1 1 d . . . C2 C 0.67609(16) 0.18182(15) 1.07187(15) 0.0369(4) Uani 1 1 d . . . H2A H 0.6363(16) 0.1113(16) 1.0964(15) 0.038(4) Uiso 1 1 d . . . C4 C 0.76380(17) 0.36716(16) 1.07548(16) 0.0421(4) Uani 1 1 d . . . H4A H 0.7934(18) 0.4522(18) 1.1056(17) 0.053(5) Uiso 1 1 d . . . C5 C 0.75676(17) 0.30007(16) 0.96970(17) 0.0418(4) Uani 1 1 d . . . H5A H 0.7769(19) 0.3173(17) 0.8999(18) 0.053(5) Uiso 1 1 d . . . C6 C 0.7065(2) 0.32553(18) 1.26150(18) 0.0459(5) Uani 1 1 d . . . H6A H 0.673(2) 0.2514(19) 1.2855(18) 0.065(6) Uiso 1 1 d . . . H6B H 0.652(2) 0.390(2) 1.2563(19) 0.068(6) Uiso 1 1 d . . . H6C H 0.795(2) 0.3473(19) 1.327(2) 0.068(6) Uiso 1 1 d . . . C7 C 0.66678(17) 0.08315(16) 0.86608(16) 0.0399(4) Uani 1 1 d . . . H7A H 0.6775(17) 0.0076(17) 0.9014(15) 0.042(5) Uiso 1 1 d . . . H7B H 0.7294(18) 0.0920(15) 0.8222(16) 0.044(5) Uiso 1 1 d . . . C8 C 0.52321(17) 0.07902(15) 0.77448(15) 0.0390(4) Uani 1 1 d . . . H8A H 0.5098(16) 0.1616(16) 0.7537(14) 0.039(4) Uiso 1 1 d . . . C9 C 0.4910(3) -0.01272(19) 0.6587(2) 0.0567(5) Uani 1 1 d . . . H9A H 0.399(3) -0.012(2) 0.595(2) 0.074(7) Uiso 1 1 d . . . H9B H 0.509(2) -0.096(2) 0.6833(19) 0.070(6) Uiso 1 1 d . . . H9C H 0.554(2) 0.007(2) 0.618(2) 0.075(7) Uiso 1 1 d . . . C10 C 0.00192(15) 0.28481(13) 0.70656(13) 0.0310(4) Uani 1 1 d . . . C11 C -0.12768(16) 0.22449(15) 0.67893(15) 0.0376(4) Uani 1 1 d . . . H11A H -0.1372(18) 0.1435(17) 0.7044(16) 0.050(5) Uiso 1 1 d . . . C12 C -0.24448(17) 0.27065(16) 0.61205(16) 0.0424(4) Uani 1 1 d . . . H12A H -0.333(2) 0.2220(17) 0.5983(16) 0.053(5) Uiso 1 1 d . . . C13 C -0.23679(17) 0.37958(16) 0.56782(15) 0.0393(4) Uani 1 1 d . . . H13A H -0.3156(19) 0.4158(16) 0.5203(16) 0.046(5) Uiso 1 1 d . . . C14 C -0.11078(17) 0.44194(15) 0.59113(15) 0.0385(4) Uani 1 1 d . . . H14A H -0.1066(18) 0.5192(18) 0.5586(16) 0.049(5) Uiso 1 1 d . . . C15 C 0.00437(16) 0.39441(14) 0.65895(14) 0.0350(4) Uani 1 1 d . . . H15A H 0.0918(18) 0.4398(15) 0.6705(15) 0.041(4) Uiso 1 1 d . . . C16 C 0.26348(15) 0.28683(13) 0.75012(14) 0.0328(4) Uani 1 1 d . . . C17 C 0.25007(17) 0.26901(15) 0.62432(16) 0.0388(4) Uani 1 1 d . . . H17A H 0.1711(18) 0.2199(16) 0.5589(16) 0.043(5) Uiso 1 1 d . . . C18 C 0.34653(18) 0.31931(16) 0.58271(18) 0.0445(4) Uani 1 1 d . . . H18A H 0.3278(17) 0.2999(15) 0.4911(17) 0.045(5) Uiso 1 1 d . . . C19 C 0.46081(18) 0.39296(15) 0.66706(18) 0.0448(5) Uani 1 1 d . . . H19A H 0.526(2) 0.4298(18) 0.6388(18) 0.061(6) Uiso 1 1 d . . . C20 C 0.47844(17) 0.41403(15) 0.79197(18) 0.0403(4) Uani 1 1 d . . . H20A H 0.5601(18) 0.4668(15) 0.8572(16) 0.045(5) Uiso 1 1 d . . . C21 C 0.38221(15) 0.36069(14) 0.83226(16) 0.0357(4) Uani 1 1 d . . . H21A H 0.4005(16) 0.3794(15) 0.9258(16) 0.038(4) Uiso 1 1 d . . . C22 C 0.10822(14) 0.08326(14) 0.76940(14) 0.0314(4) Uani 1 1 d . . . C23 C 0.05386(16) 0.02294(15) 0.84415(16) 0.0371(4) Uani 1 1 d . . . H23A H 0.0500(16) 0.0679(15) 0.9174(16) 0.040(4) Uiso 1 1 d . . . C24 C 0.00665(17) -0.10038(15) 0.81850(16) 0.0410(4) Uani 1 1 d . . . H24A H -0.0316(19) -0.1352(17) 0.8750(18) 0.059(5) Uiso 1 1 d . . . C25 C 0.01412(17) -0.17052(15) 0.71594(16) 0.0414(4) Uani 1 1 d . . . H25A H -0.0196(18) -0.2544(17) 0.6971(16) 0.048(5) Uiso 1 1 d . . . C26 C 0.07020(16) -0.11616(15) 0.64123(16) 0.0390(4) Uani 1 1 d . . . H26A H 0.0752(17) -0.1654(15) 0.5665(17) 0.046(5) Uiso 1 1 d . . . C27 C 0.11556(15) 0.00782(15) 0.66800(15) 0.0350(4) Uani 1 1 d . . . H27A H 0.1514(17) 0.0439(15) 0.6118(16) 0.044(5) Uiso 1 1 d . . . C28 C 0.17855(14) 0.28149(13) 0.94266(14) 0.0307(4) Uani 1 1 d . . . C29 C 0.10687(16) 0.35954(14) 0.98886(15) 0.0337(4) Uani 1 1 d . . . H29A H 0.0283(17) 0.3882(14) 0.9260(15) 0.036(4) Uiso 1 1 d . . . C30 C 0.14049(17) 0.39717(15) 1.11597(15) 0.0380(4) Uani 1 1 d . . . H30A H 0.0934(19) 0.4526(17) 1.1475(17) 0.051(5) Uiso 1 1 d . . . C31 C 0.24798(17) 0.35799(14) 1.20352(15) 0.0382(4) Uani 1 1 d . . . H31A H 0.2719(16) 0.3857(14) 1.2958(16) 0.040(4) Uiso 1 1 d . . . C32 C 0.32178(17) 0.28043(15) 1.16170(16) 0.0389(4) Uani 1 1 d . . . H32A H 0.3949(19) 0.2521(15) 1.2228(17) 0.046(5) Uiso 1 1 d . . . C33 C 0.28757(16) 0.24359(14) 1.03530(15) 0.0358(4) Uani 1 1 d . . . H33A H 0.3368(17) 0.1858(15) 1.0064(15) 0.041(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B 0.0277(9) 0.0348(9) 0.0365(10) 0.0089(8) 0.0147(8) -0.0007(7) N1 0.0303(7) 0.0376(7) 0.0387(8) 0.0083(6) 0.0149(6) -0.0017(6) N2 0.0332(7) 0.0364(8) 0.0393(8) 0.0073(6) 0.0141(6) 0.0000(6) O1 0.0345(7) 0.0490(7) 0.0462(7) 0.0146(6) 0.0148(6) 0.0013(6) C2 0.0342(9) 0.0360(9) 0.0435(10) 0.0100(8) 0.0181(8) -0.0005(7) C4 0.0402(10) 0.0373(9) 0.0456(10) 0.0093(8) 0.0144(8) -0.0067(8) C5 0.0379(10) 0.0446(10) 0.0422(10) 0.0128(8) 0.0155(8) -0.0080(8) C6 0.0527(12) 0.0446(11) 0.0445(11) 0.0065(9) 0.0236(10) 0.0052(10) C7 0.0412(10) 0.0378(10) 0.0462(10) 0.0047(8) 0.0242(8) 0.0021(8) C8 0.0474(10) 0.0328(9) 0.0389(9) 0.0115(7) 0.0180(8) 0.0019(8) C9 0.0702(15) 0.0512(12) 0.0446(11) 0.0033(9) 0.0194(11) 0.0015(11) C10 0.0317(8) 0.0343(8) 0.0292(8) 0.0034(7) 0.0157(7) -0.0005(7) C11 0.0328(9) 0.0411(9) 0.0452(10) 0.0120(8) 0.0212(8) 0.0021(7) C12 0.0310(9) 0.0507(10) 0.0477(10) 0.0080(8) 0.0183(8) 0.0013(8) C13 0.0357(10) 0.0520(10) 0.0338(9) 0.0072(8) 0.0156(7) 0.0132(8) C14 0.0457(10) 0.0372(9) 0.0359(9) 0.0075(7) 0.0183(8) 0.0072(8) C15 0.0338(9) 0.0345(9) 0.0357(9) 0.0037(7) 0.0136(7) -0.0018(7) C16 0.0293(8) 0.0313(8) 0.0407(9) 0.0109(7) 0.0150(7) 0.0044(7) C17 0.0348(9) 0.0439(9) 0.0404(10) 0.0121(8) 0.0166(8) 0.0015(8) C18 0.0475(11) 0.0495(10) 0.0502(11) 0.0207(9) 0.0295(9) 0.0127(9) C19 0.0377(10) 0.0407(10) 0.0710(13) 0.0226(9) 0.0334(9) 0.0073(8) C20 0.0305(9) 0.0334(9) 0.0623(12) 0.0134(8) 0.0223(8) 0.0023(7) C21 0.0323(9) 0.0299(8) 0.0464(10) 0.0089(7) 0.0164(8) 0.0017(7) C22 0.0244(8) 0.0359(8) 0.0330(8) 0.0063(7) 0.0103(6) 0.0011(6) C23 0.0385(9) 0.0363(9) 0.0389(9) 0.0051(7) 0.0188(8) 0.0003(7) C24 0.0409(10) 0.0380(9) 0.0451(10) 0.0095(8) 0.0185(8) -0.0033(8) C25 0.0387(10) 0.0315(9) 0.0470(10) 0.0030(8) 0.0106(8) -0.0038(7) C26 0.0359(9) 0.0392(9) 0.0373(9) 0.0005(8) 0.0103(7) 0.0037(7) C27 0.0283(8) 0.0418(9) 0.0343(9) 0.0078(7) 0.0111(7) 0.0032(7) C28 0.0286(8) 0.0264(7) 0.0393(9) 0.0094(7) 0.0158(7) -0.0035(6) C29 0.0312(9) 0.0343(8) 0.0393(9) 0.0111(7) 0.0168(8) 0.0015(7) C30 0.0433(10) 0.0348(9) 0.0422(10) 0.0074(7) 0.0238(8) 0.0023(8) C31 0.0444(10) 0.0349(9) 0.0356(9) 0.0054(7) 0.0181(8) -0.0067(8) C32 0.0356(9) 0.0386(9) 0.0376(10) 0.0118(8) 0.0079(8) -0.0013(8) C33 0.0345(9) 0.0332(9) 0.0409(10) 0.0079(7) 0.0156(8) 0.0023(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B C28 1.646(2) . ? B C10 1.659(2) . ? B C22 1.661(2) . ? B C16 1.664(2) . ? N1 C2 1.330(2) . ? N1 C5 1.380(2) . ? N1 C7 1.460(2) . ? N2 C2 1.323(2) . ? N2 C4 1.381(2) . ? N2 C6 1.465(2) . ? O1 C8 1.430(2) . ? C4 C5 1.342(3) . ? C7 C8 1.517(2) . ? C8 C9 1.511(3) . ? C10 C15 1.402(2) . ? C10 C11 1.404(2) . ? C11 C12 1.393(2) . ? C12 C13 1.381(3) . ? C13 C14 1.389(2) . ? C14 C15 1.391(2) . ? C16 C17 1.405(2) . ? C16 C21 1.409(2) . ? C17 C18 1.398(2) . ? C18 C19 1.387(3) . ? C19 C20 1.383(3) . ? C20 C21 1.399(2) . ? C22 C27 1.404(2) . ? C22 C23 1.408(2) . ? C23 C24 1.391(2) . ? C24 C25 1.386(2) . ? C25 C26 1.386(2) . ? C26 C27 1.394(2) . ? C28 C29 1.402(2) . ? C28 C33 1.407(2) . ? C29 C30 1.391(2) . ? C30 C31 1.376(2) . ? C31 C32 1.390(2) . ? C32 C33 1.381(2) . ? 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 C28 B C10 110.44(12) . . ? C28 B C22 108.26(12) . . ? C10 B C22 107.11(12) . . ? C28 B C16 110.01(12) . . ? C10 B C16 107.07(12) . . ? C22 B C16 113.91(12) . . ? C2 N1 C5 108.02(14) . . ? C2 N1 C7 125.80(14) . . ? C5 N1 C7 125.92(14) . . ? C2 N2 C4 108.49(14) . . ? C2 N2 C6 125.77(14) . . ? C4 N2 C6 125.58(14) . . ? N2 C2 N1 109.00(14) . . ? C5 C4 N2 107.00(15) . . ? C4 C5 N1 107.49(15) . . ? N1 C7 C8 111.18(13) . . ? O1 C8 C9 111.06(15) . . ? O1 C8 C7 106.29(13) . . ? C9 C8 C7 111.96(16) . . ? C15 C10 C11 114.47(15) . . ? C15 C10 B 122.66(13) . . ? C11 C10 B 122.82(14) . . ? C12 C11 C10 122.94(16) . . ? C13 C12 C11 120.39(16) . . ? C12 C13 C14 118.87(16) . . ? C13 C14 C15 119.65(16) . . ? C14 C15 C10 123.66(15) . . ? C17 C16 C21 114.72(14) . . ? C17 C16 B 121.29(13) . . ? C21 C16 B 123.78(14) . . ? C18 C17 C16 123.19(16) . . ? C19 C18 C17 119.86(18) . . ? C20 C19 C18 119.23(16) . . ? C19 C20 C21 120.07(16) . . ? C20 C21 C16 122.91(16) . . ? C27 C22 C23 114.47(14) . . ? C27 C22 B 124.63(13) . . ? C23 C22 B 120.45(13) . . ? C24 C23 C22 123.41(15) . . ? C25 C24 C23 119.83(16) . . ? C24 C25 C26 119.05(16) . . ? C25 C26 C27 120.10(16) . . ? C26 C27 C22 123.10(15) . . ? C29 C28 C33 114.62(14) . . ? C29 C28 B 124.39(14) . . ? C33 C28 B 120.99(13) . . ? C30 C29 C28 122.99(16) . . ? C31 C30 C29 120.53(15) . . ? C30 C31 C32 118.35(16) . . ? C33 C32 C31 120.68(16) . . ? C32 C33 C28 122.84(15) . . ? 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 N1 C7 C8 C9 171.86(15) . . . . ? C2 N1 C7 C8 84.25(19) . . . . ? C5 N1 C7 C8 -89.21(19) . . . . ? N1 C7 C8 O1 -66.71(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2A O1 0.984(18) 2.211(18) 3.193(2) 175.9(13) 2_657 C4 H4A C15 0.962(19) 3.027(19) 3.785(2) 136.7(14) 2_667 C8 H8A C17 0.990(17) 3.072(16) 3.790(3) 130.5(12) . C8 H8A C18 0.990(17) 2.984(17) 3.862(3) 148.4(12) . C8 H8A C19 0.990(17) 2.902(18) 3.888(3) 174.4(12) . C8 H8A C20 0.990(17) 2.883(17) 3.818(3) 157.8(12) . C8 H8A C21 0.990(17) 2.949(16) 3.718(2) 135.2(12) . O1 H1A B 0.87(3) 3.07(3) 3.866(2) 153(2) . O1 H1A C16 0.87(3) 2.70(3) 3.428(2) 141(2) . O1 H1A C22 0.87(3) 2.64(3) 3.411(2) 148(2) . O1 H1A C27 0.87(3) 2.55(3) 3.280(2) 142(2) . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.235 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.040