# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global #============================================== #============================== _audit_creation_date '21-8-2000' _audit_creation_method 'SHELXTL CIF,IUCr SHELXL97-template and Local input' _audit_update_record ; ? ; #============================================== #============================== # 1. SUBMISSION DETAILS _journal_coden_Cambridge 207 loop_ _publ_author_name 'Donohoe, Timothy' 'Calabrese, Andrew A.' 'Frampton, Christopher S.' 'Guillermin, Jean-Baptiste' 'Walter, Daryl' _publ_contact_author_name 'Dr Timothy Donohoe' _publ_contact_author_address ; Department of Chemistry University of Oxford Dyson Perrins Laboratory South Parks Road Oxford Oxon OX1 3QY UNITED KINGDOM ; _publ_contact_author_phone '44(1707)366272' _publ_contact_author_fax '44(1707)366907' _publ_contact_author_email 'TIMOTHY.DONOHOE@CHEM.OX.AC.UK' _publ_requested_journal 'Perkin Transactions 1' _publ_section_title ; Partial reduction of 3-heteroatom substituted 2-furoic acids: the role of an ortho group on viability and stereoselectivity ; _publ_requested_category FO _publ_requested_coeditor_name '?' _publ_contact_letter ? #============================================== _publ_section_experimental ; The data collection nominally covered a sphere of reciprocal space by a combination of three sets of exposures; each set had a different \f angle for the crystal, 0, 120 and 240\% repectively. Each exposure covered 0.3\% in \w with a 30 second correlated frame time. A total of 600 frames were accumalated in each \w sweep. The crystal to detector distance was 4.778 cm. Coverage of the unique set was 93.9% to 29.45\% in \q, (0.72\%A) and 100% complete to 26.37\% in \q, (0.80\%A). Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analyzing the duplicate reflections, a further 50 frames of data were collected at positive 2\q to improve cell refinement statistics. Area detector scaling and absorption corrections were performed by SADABS. This correction was used to scale the frames of data and to correct for absorption of the primary beam by the crystal support using the method of Blessing (1995). A correction for absorption of the primary beam by the crystal was not applied and as such no transmission factors are quoted. ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; Allen, F.H., Kennard, O., (1993). Chemical Design Automation News 8, 1 & 31-37. Blessing R.H. (1995). Acta Cryst., A51, 33-38. Bruker AXS (1997). SMART, SAINT and SADABS area-detector control and integration software. Bruker AXS Inc., Madison, WI 53719, U.S.A. Sheldrick, G.M. (1997). SHELXTL Version 5. Bruker AXS Inc., Madison, WI 53179, U.S.A. ; _publ_section_figure_captions ; ? ; _publ_section_table_legends ; ? ; _publ_section_acknowledgements ; ? ; #============================================== #============================== data_0572s _database_code_CSD 183703 #============================================== #============================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H25 N1 O3 Si1' _chemical_formula_weight 283.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Si' 'Si' 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.1439(11) _cell_length_b 11.6771(15) _cell_length_c 15.438(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1648.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 969 _cell_measurement_theta_min 2.187 _cell_measurement_theta_max 28.945 _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.146 _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 123(1) _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 'Bruker AXS 1K CCD area detector' _diffrn_measurement_method 'narrow frame \w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 'see text' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 15940 _diffrn_reflns_av_R_equivalents 0.0149 _diffrn_reflns_av_sigmaI/netI 0.0127 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 29.45 _diffrn_measured_fraction_theta_max 0.939 _reflns_number_total 4186 _reflns_number_gt 3901 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.06 (Bruker AXS, 1999)' _computing_cell_refinement 'SMART V5.06/SAINT V6.02a (Bruker AXS, 1999)' _computing_data_reduction 'SAINT V6.02a (Bruker AXS, 1999)' _computing_structure_solution 'SHELXTL V5.10 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL V5.10 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V5.10 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL V5.10 (Sheldrick, 1997)' _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^)+(0.0755P)^2^+0.0750P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(9) _refine_ls_number_reflns 4186 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0952 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.303 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.040 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 Si1 Si 0.67168(4) 0.85102(3) 0.82792(2) 0.03030(10) Uani 1 1 d . . . O1 O 0.99946(11) 1.05685(9) 0.71984(6) 0.0361(2) Uani 1 1 d . . . O2 O 0.76685(12) 1.16067(11) 0.87993(8) 0.0477(3) Uani 1 1 d . . . O3 O 0.98599(15) 1.28375(14) 1.08841(9) 0.0567(4) Uani 1 1 d . . . H3C H 1.063(4) 1.293(3) 1.112(2) 0.082(9) Uiso 1 1 d . . . N1 N 0.98376(12) 1.07842(9) 0.90478(7) 0.0286(2) Uani 1 1 d . . . C1 C 0.74898(19) 1.11772(13) 0.70781(10) 0.0397(3) Uani 1 1 d . . . H1A H 0.781(3) 1.204(2) 0.7012(15) 0.056(6) Uiso 1 1 d . . . H1B H 0.656(3) 1.1128(18) 0.7292(14) 0.051(5) Uiso 1 1 d . . . H1C H 0.747(2) 1.0876(17) 0.6500(13) 0.041(5) Uiso 1 1 d . . . C2 C 0.85952(13) 1.05003(11) 0.76183(8) 0.0286(2) Uani 1 1 d . . . C3 C 1.0325(2) 0.94864(15) 0.68065(12) 0.0482(4) Uani 1 1 d . . . H3A H 1.030(3) 0.9516(19) 0.6181(17) 0.061(6) Uiso 1 1 d . . . H3B H 1.136(3) 0.9271(18) 0.7008(14) 0.051(5) Uiso 1 1 d . . . C4 C 0.92131(18) 0.86822(13) 0.71774(11) 0.0406(3) Uani 1 1 d . . . H4A H 0.921(3) 0.7907(19) 0.7088(15) 0.054(6) Uiso 1 1 d . . . C5 C 0.82266(15) 0.92251(10) 0.76588(8) 0.0291(2) Uani 1 1 d . . . C6 C 0.7082(3) 0.8656(2) 0.94625(11) 0.0625(6) Uani 1 1 d . . . H6A H 0.683(3) 0.955(2) 0.9684(17) 0.069(7) Uiso 1 1 d . . . H6B H 0.794(3) 0.840(2) 0.9571(16) 0.056(7) Uiso 1 1 d . . . H6C H 0.642(4) 0.823(2) 0.974(2) 0.084(9) Uiso 1 1 d . . . C7 C 0.48984(18) 0.91490(14) 0.80303(13) 0.0464(4) Uani 1 1 d . . . H7A H 0.488(3) 0.986(2) 0.8250(17) 0.064(6) Uiso 1 1 d . . . H7B H 0.420(3) 0.869(2) 0.8324(18) 0.081(8) Uiso 1 1 d . . . H7C H 0.471(3) 0.912(2) 0.745(2) 0.072(7) Uiso 1 1 d . . . C8 C 0.67219(18) 0.69793(12) 0.79542(12) 0.0417(3) Uani 1 1 d . . . H8A H 0.591(2) 0.6582(19) 0.8326(14) 0.052(6) Uiso 1 1 d . . . H8B H 0.758(3) 0.6577(19) 0.8056(15) 0.052(5) Uiso 1 1 d . . . H8C H 0.653(3) 0.6997(18) 0.7278(14) 0.051(5) Uiso 1 1 d . . . C9 C 0.86911(13) 1.10103(11) 0.85338(8) 0.0286(2) Uani 1 1 d . . . C10 C 1.10993(17) 1.00179(14) 0.88781(11) 0.0406(3) Uani 1 1 d . . . H10A H 1.072(3) 0.926(2) 0.8781(15) 0.056(6) Uiso 1 1 d . . . H10B H 1.167(3) 1.024(2) 0.8379(16) 0.062(6) Uiso 1 1 d . . . C11 C 1.1950(2) 1.0066(3) 0.97032(15) 0.0726(7) Uani 1 1 d . . . H11A H 1.256(3) 0.941(3) 0.9814(19) 0.076(8) Uiso 1 1 d . . . H11B H 1.271(4) 1.088(3) 0.964(2) 0.087(9) Uiso 1 1 d . . . C12 C 1.0934(3) 1.0429(3) 1.03959(13) 0.0723(7) Uani 1 1 d . . . H12A H 1.038(4) 0.957(3) 1.059(2) 0.109(12) Uiso 1 1 d . . . H12B H 1.134(4) 1.069(3) 1.0934(19) 0.086(9) Uiso 1 1 d . . . C13 C 0.97964(16) 1.11737(12) 0.99623(8) 0.0342(3) Uani 1 1 d . . . H13A H 0.893(2) 1.0985(17) 1.0221(13) 0.040(5) Uiso 1 1 d . . . C14 C 1.00909(19) 1.24561(15) 1.00208(10) 0.0419(3) Uani 1 1 d . . . H14A H 0.942(3) 1.2897(18) 0.9609(14) 0.048(5) Uiso 1 1 d . . . H14B H 1.104(3) 1.2648(19) 0.9829(15) 0.053(6) 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 Si1 0.03068(17) 0.03155(16) 0.02866(16) -0.00211(13) 0.00251(13) -0.00611(13) O1 0.0361(5) 0.0367(5) 0.0355(5) -0.0045(4) 0.0112(4) -0.0073(4) O2 0.0318(5) 0.0647(7) 0.0467(6) -0.0240(6) -0.0061(4) 0.0132(5) O3 0.0385(6) 0.0891(10) 0.0424(6) -0.0311(6) 0.0036(5) -0.0146(6) N1 0.0286(5) 0.0303(5) 0.0269(5) -0.0001(4) 0.0015(4) 0.0025(4) C1 0.0439(8) 0.0399(7) 0.0353(7) 0.0049(6) -0.0070(6) -0.0010(6) C2 0.0284(6) 0.0296(5) 0.0277(5) -0.0024(4) 0.0026(4) -0.0029(4) C3 0.0512(9) 0.0444(8) 0.0491(9) -0.0146(7) 0.0250(7) -0.0081(6) C4 0.0443(7) 0.0358(7) 0.0417(8) -0.0116(6) 0.0135(6) -0.0039(5) C5 0.0323(6) 0.0282(5) 0.0267(5) -0.0035(4) 0.0024(5) -0.0035(5) C6 0.0706(13) 0.0872(16) 0.0296(7) 0.0021(9) 0.0027(8) -0.0371(12) C7 0.0361(7) 0.0369(7) 0.0661(11) -0.0020(7) 0.0098(7) 0.0035(6) C8 0.0360(7) 0.0287(6) 0.0606(9) 0.0014(6) -0.0018(7) -0.0016(6) C9 0.0257(5) 0.0293(5) 0.0307(6) -0.0047(5) 0.0008(4) -0.0029(4) C10 0.0351(7) 0.0431(8) 0.0435(8) 0.0039(6) 0.0018(6) 0.0145(6) C11 0.0523(11) 0.1122(19) 0.0532(11) -0.0042(11) -0.0147(9) 0.0376(12) C12 0.0818(15) 0.0993(18) 0.0359(9) 0.0129(10) -0.0125(9) 0.0390(14) C13 0.0336(6) 0.0444(7) 0.0246(6) 0.0010(5) 0.0002(5) -0.0019(5) C14 0.0445(8) 0.0495(8) 0.0319(7) -0.0102(6) -0.0002(6) -0.0129(6) _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 Si1 C8 1.8567(15) . ? Si1 C7 1.8625(17) . ? Si1 C6 1.8648(18) . ? Si1 C5 1.8763(14) . ? O1 C3 1.4331(18) . ? O1 C2 1.4367(15) . ? O2 C9 1.2358(17) . ? O3 C14 1.4210(18) . ? N1 C9 1.3411(17) . ? N1 C10 1.4833(17) . ? N1 C13 1.4839(16) . ? C1 C2 1.530(2) . ? C2 C5 1.5280(17) . ? C2 C9 1.5362(17) . ? C3 C4 1.498(2) . ? C4 C5 1.3296(19) . ? C10 C11 1.493(3) . ? C11 C12 1.478(3) . ? C12 C13 1.512(2) . ? C13 C14 1.524(2) . ? O3 H3C 0.80(3) . ? C1 H1A 1.06(2) . ? C1 H1B 0.92(2) . ? C1 H1C 0.96(2) . ? C3 H3A 0.97(3) . ? C3 H3B 1.03(2) . ? C4 H4A 0.92(2) . ? C6 H6A 1.12(3) . ? C6 H6B 0.86(3) . ? C6 H6C 0.89(3) . ? C7 H7A 0.90(3) . ? C7 H7B 0.95(3) . ? C7 H7C 0.92(3) . ? C8 H8A 1.05(2) . ? C8 H8B 0.93(2) . ? C8 H8C 1.06(2) . ? C10 H10A 0.96(2) . ? C10 H10B 0.97(3) . ? C11 H11A 0.96(3) . ? C11 H11B 1.18(3) . ? C12 H12A 1.16(4) . ? C12 H12B 0.96(3) . ? C13 H13A 0.92(2) . ? C14 H14A 1.02(2) . ? C14 H14B 0.94(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 C8 Si1 C7 109.40(8) . . ? C8 Si1 C6 110.63(10) . . ? C7 Si1 C6 109.00(11) . . ? C8 Si1 C5 106.77(7) . . ? C7 Si1 C5 111.92(7) . . ? C6 Si1 C5 109.12(8) . . ? C3 O1 C2 109.21(10) . . ? C9 N1 C10 128.48(11) . . ? C9 N1 C13 118.87(11) . . ? C10 N1 C13 111.88(11) . . ? O1 C2 C5 105.60(10) . . ? O1 C2 C1 108.28(11) . . ? C5 C2 C1 112.33(11) . . ? O1 C2 C9 110.05(10) . . ? C5 C2 C9 110.66(10) . . ? C1 C2 C9 109.81(11) . . ? O1 C3 C4 104.39(11) . . ? C5 C4 C3 112.04(13) . . ? C4 C5 Si1 124.92(10) . . ? C2 C5 Si1 128.08(9) . . ? O2 C9 N1 120.40(12) . . ? O2 C9 C2 118.72(12) . . ? N1 C9 C2 120.84(11) . . ? N1 C10 C11 103.38(14) . . ? C12 C11 C10 107.51(17) . . ? C11 C12 C13 106.05(15) . . ? N1 C13 C12 103.14(13) . . ? N1 C13 C14 110.67(11) . . ? C12 C13 C14 114.68(17) . . ? O3 C14 C13 109.71(14) . . ? C14 O3 H3C 109(2) . . ? C2 C1 H1A 111.3(13) . . ? C2 C1 H1B 112.7(14) . . ? H1A C1 H1B 110.7(18) . . ? C2 C1 H1C 109.2(12) . . ? H1A C1 H1C 105.4(17) . . ? H1B C1 H1C 107.2(19) . . ? O1 C3 H3A 112.6(14) . . ? C4 C3 H3A 112.9(15) . . ? O1 C3 H3B 106.4(12) . . ? C4 C3 H3B 110.9(12) . . ? H3A C3 H3B 109(2) . . ? C5 C4 H4A 123.4(14) . . ? C3 C4 H4A 124.5(14) . . ? C4 C5 C2 106.99(11) . . ? Si1 C6 H6A 110.2(14) . . ? Si1 C6 H6B 108.9(16) . . ? H6A C6 H6B 117(2) . . ? Si1 C6 H6C 107(2) . . ? H6A C6 H6C 104(2) . . ? H6B C6 H6C 109(3) . . ? Si1 C7 H7A 107.9(16) . . ? Si1 C7 H7B 106.1(17) . . ? H7A C7 H7B 109(2) . . ? Si1 C7 H7C 110.8(18) . . ? H7A C7 H7C 114(2) . . ? H7B C7 H7C 108(3) . . ? Si1 C8 H8A 106.1(12) . . ? Si1 C8 H8B 116.3(14) . . ? H8A C8 H8B 106.5(18) . . ? Si1 C8 H8C 104.3(11) . . ? H8A C8 H8C 115.6(17) . . ? H8B C8 H8C 108.4(19) . . ? N1 C10 H10A 107.7(14) . . ? C11 C10 H10A 110.8(14) . . ? N1 C10 H10B 113.8(14) . . ? C11 C10 H10B 112.8(15) . . ? H10A C10 H10B 108.2(19) . . ? C12 C11 H11A 117.5(18) . . ? C10 C11 H11A 114.9(17) . . ? C12 C11 H11B 101.4(15) . . ? C10 C11 H11B 105.6(16) . . ? H11A C11 H11B 108(2) . . ? C11 C12 H12A 102.3(19) . . ? C13 C12 H12A 108.2(19) . . ? C11 C12 H12B 118.1(19) . . ? C13 C12 H12B 117.9(19) . . ? H12A C12 H12B 103(3) . . ? N1 C13 H13A 111.3(12) . . ? C12 C13 H13A 105.4(13) . . ? C14 C13 H13A 111.3(12) . . ? O3 C14 H14A 109.6(12) . . ? C13 C14 H14A 110.6(12) . . ? O3 C14 H14B 111.0(15) . . ? C13 C14 H14B 112.2(14) . . ? H14A C14 H14B 103.6(19) . . ? 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 C3 O1 C2 C5 13.58(15) . . . . ? C3 O1 C2 C1 -106.93(14) . . . . ? C3 O1 C2 C9 133.04(13) . . . . ? C2 O1 C3 C4 -12.32(18) . . . . ? O1 C3 C4 C5 6.3(2) . . . . ? C3 C4 C5 C2 1.94(19) . . . . ? C3 C4 C5 Si1 -176.71(12) . . . . ? O1 C2 C5 C4 -9.46(15) . . . . ? C1 C2 C5 C4 108.36(15) . . . . ? C9 C2 C5 C4 -128.52(13) . . . . ? O1 C2 C5 Si1 169.13(9) . . . . ? C1 C2 C5 Si1 -73.05(15) . . . . ? C9 C2 C5 Si1 50.07(16) . . . . ? C8 Si1 C5 C4 -8.25(16) . . . . ? C7 Si1 C5 C4 -127.93(14) . . . . ? C6 Si1 C5 C4 111.35(17) . . . . ? C8 Si1 C5 C2 173.40(12) . . . . ? C7 Si1 C5 C2 53.72(14) . . . . ? C6 Si1 C5 C2 -67.00(16) . . . . ? C10 N1 C9 O2 174.48(14) . . . . ? C13 N1 C9 O2 5.37(19) . . . . ? C10 N1 C9 C2 -3.3(2) . . . . ? C13 N1 C9 C2 -172.40(11) . . . . ? O1 C2 C9 O2 139.62(13) . . . . ? C5 C2 C9 O2 -104.04(15) . . . . ? C1 C2 C9 O2 20.53(17) . . . . ? O1 C2 C9 N1 -42.57(16) . . . . ? C5 C2 C9 N1 73.77(15) . . . . ? C1 C2 C9 N1 -161.66(12) . . . . ? C9 N1 C10 C11 -176.61(17) . . . . ? C13 N1 C10 C11 -6.9(2) . . . . ? N1 C10 C11 C12 22.3(3) . . . . ? C10 C11 C12 C13 -29.6(3) . . . . ? C9 N1 C13 C12 160.35(17) . . . . ? C10 N1 C13 C12 -10.48(19) . . . . ? C9 N1 C13 C14 -76.53(16) . . . . ? C10 N1 C13 C14 112.64(14) . . . . ? C11 C12 C13 N1 24.0(3) . . . . ? C11 C12 C13 C14 -96.4(2) . . . . ? N1 C13 C14 O3 172.48(12) . . . . ? C12 C13 C14 O3 -71.36(19) . . . . ? 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 O3 H3C O2 0.80(3) 1.94(3) 2.6936(17) 156(3) 4_577 #============================================== #============================== # END of CIF #============================================== #==============================