# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1802 _database_code_depnum_ccdc_archive 'CCDC 874664' #TrackingRef 'ccdc_deposit.cif' _audit_creation_date 2012-04-02T17:47:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 1-Methoxy-1,1,3,3,3-pentaphenyldisiloxane ; _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_hall '-P 1' _chemical_formula_moiety 'C31 H28 O2 Si2' _chemical_formula_sum 'C31 H28 O2 Si2' _chemical_formula_weight 488.71 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1738(3) _cell_length_b 10.1328(4) _cell_length_c 16.4692(6) _cell_angle_alpha 98.523(3) _cell_angle_beta 92.493(3) _cell_angle_gamma 103.426(3) _cell_volume 1307.80(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5131 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 26.000 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.162 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.968 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur S Oxford Diffraction' _diffrn_measurement_method Omega-scan _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_unetI/netI 0.0585 _diffrn_reflns_number 22177 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 5131 _reflns_number_gt 3603 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38)' ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 (Farrugia, 1997) and Schakal 92 (Keller 1992) ; _computing_publication_material 'wingx (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0512P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5131 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.068 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.0999 _refine_ls_wR_factor_gt 0.0958 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.435 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.05 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 C1 C -0.0956(2) 0.55750(19) 0.18982(12) 0.0233(5) Uani 1 1 d . . . C2 C -0.2247(3) 0.4501(2) 0.20380(14) 0.0384(6) Uani 1 1 d . . . H2 H -0.2375 0.4325 0.2585 0.046 Uiso 1 1 calc R . . C3 C -0.3348(3) 0.3680(3) 0.14107(16) 0.0478(7) Uani 1 1 d . . . H3 H -0.422 0.295 0.1529 0.057 Uiso 1 1 calc R . . C4 C -0.3193(3) 0.3910(3) 0.06168(15) 0.0426(6) Uani 1 1 d . . . H4 H -0.3939 0.3331 0.018 0.051 Uiso 1 1 calc R . . C5 C -0.1951(3) 0.4984(3) 0.04579(15) 0.0463(7) Uani 1 1 d . . . H5 H -0.1851 0.5169 -0.0089 0.056 Uiso 1 1 calc R . . C6 C -0.0848(3) 0.5797(2) 0.10927(14) 0.0384(6) Uani 1 1 d . . . H6 H 0.0013 0.6533 0.0972 0.046 Uiso 1 1 calc R . . C7 C -0.0409(2) 0.70366(19) 0.37010(12) 0.0215(4) Uani 1 1 d . . . C8 C -0.0886(3) 0.8276(2) 0.38793(14) 0.0370(6) Uani 1 1 d . . . H8 H -0.0725 0.8895 0.3493 0.044 Uiso 1 1 calc R . . C9 C -0.1581(3) 0.8626(2) 0.45988(16) 0.0475(7) Uani 1 1 d . . . H9 H -0.1896 0.9477 0.4702 0.057 Uiso 1 1 calc R . . C10 C -0.1827(3) 0.7760(2) 0.51714(14) 0.0371(6) Uani 1 1 d . . . H10 H -0.2289 0.8015 0.5674 0.045 Uiso 1 1 calc R . . C11 C -0.1398(3) 0.6520(2) 0.50103(13) 0.0309(5) Uani 1 1 d . . . H11 H -0.1585 0.5902 0.5397 0.037 Uiso 1 1 calc R . . C12 C -0.0698(2) 0.6173(2) 0.42886(12) 0.0262(5) Uani 1 1 d . . . H12 H -0.0401 0.5314 0.4188 0.031 Uiso 1 1 calc R . . C13 C 0.2115(2) 0.55413(19) 0.30032(12) 0.0217(4) Uani 1 1 d . . . C14 C 0.3436(3) 0.6123(2) 0.35987(13) 0.0321(5) Uani 1 1 d . . . H14 H 0.3546 0.7036 0.3874 0.039 Uiso 1 1 calc R . . C15 C 0.4598(3) 0.5404(3) 0.38020(15) 0.0415(6) Uani 1 1 d . . . H15 H 0.5499 0.5821 0.4211 0.05 Uiso 1 1 calc R . . C16 C 0.4442(3) 0.4081(3) 0.34079(17) 0.0449(7) Uani 1 1 d . . . H16 H 0.5236 0.3582 0.3546 0.054 Uiso 1 1 calc R . . C17 C 0.3156(3) 0.3484(2) 0.28204(16) 0.0455(7) Uani 1 1 d . . . H17 H 0.3057 0.2571 0.2549 0.055 Uiso 1 1 calc R . . C18 C 0.1992(3) 0.4202(2) 0.26165(14) 0.0333(5) Uani 1 1 d . . . H18 H 0.1097 0.3775 0.2206 0.04 Uiso 1 1 calc R . . C19 C 0.2272(3) 0.98845(19) 0.13839(12) 0.0254(5) Uani 1 1 d . . . C20 C 0.3130(3) 1.0448(2) 0.07636(14) 0.0430(6) Uani 1 1 d . . . H20 H 0.4166 1.0232 0.0628 0.052 Uiso 1 1 calc R . . C21 C 0.2486(4) 1.1336(3) 0.03328(16) 0.0575(8) Uani 1 1 d . . . H21 H 0.3084 1.1717 -0.0093 0.069 Uiso 1 1 calc R . . C22 C 0.0991(4) 1.1653(3) 0.05261(17) 0.0549(8) Uani 1 1 d . . . H22 H 0.0565 1.2262 0.0236 0.066 Uiso 1 1 calc R . . C23 C 0.0122(3) 1.1108(2) 0.11249(16) 0.0477(7) Uani 1 1 d . . . H23 H -0.0917 1.1325 0.1253 0.057 Uiso 1 1 calc R . . C24 C 0.0757(3) 1.0227(2) 0.15514(14) 0.0360(6) Uani 1 1 d . . . H24 H 0.0135 0.9847 0.1971 0.043 Uiso 1 1 calc R . . C25 C 0.4754(2) 0.99306(19) 0.28405(12) 0.0233(5) Uani 1 1 d . . . C26 C 0.6368(3) 1.0556(2) 0.26464(15) 0.0357(6) Uani 1 1 d . . . H26 H 0.6663 1.0384 0.2096 0.043 Uiso 1 1 calc R . . C27 C 0.7543(3) 1.1418(2) 0.32369(16) 0.0406(6) Uani 1 1 d . . . H27 H 0.8634 1.1827 0.309 0.049 Uiso 1 1 calc R . . C28 C 0.7141(3) 1.1685(2) 0.40305(15) 0.0388(6) Uani 1 1 d . . . H28 H 0.7948 1.2279 0.4436 0.047 Uiso 1 1 calc R . . C29 C 0.5562(3) 1.1089(2) 0.42396(14) 0.0351(5) Uani 1 1 d . . . H29 H 0.5276 1.1278 0.4791 0.042 Uiso 1 1 calc R . . C30 C 0.4390(3) 1.0220(2) 0.36543(13) 0.0271(5) Uani 1 1 d . . . H30 H 0.3308 0.981 0.3811 0.033 Uiso 1 1 calc R . . C31 C 0.5170(3) 0.7068(3) 0.16702(16) 0.0479(7) Uani 1 1 d . . . H31A H 0.5577 0.7404 0.225 0.072 Uiso 1 1 calc R . . H31B H 0.6133 0.7153 0.133 0.072 Uiso 1 1 calc R . . H31C H 0.4556 0.61 0.1606 0.072 Uiso 1 1 calc R . . O1 O 0.16341(17) 0.79927(13) 0.24756(8) 0.0259(3) Uani 1 1 d . . . O2 O 0.40653(19) 0.78668(15) 0.14135(9) 0.0361(4) Uani 1 1 d . . . Si1 Si 0.06025(7) 0.65691(5) 0.27484(3) 0.02067(15) Uani 1 1 d . . . Si2 Si 0.31687(7) 0.88340(6) 0.20272(3) 0.02304(15) 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 C1 0.0215(11) 0.0225(11) 0.0269(12) 0.0031(9) 0.0016(9) 0.0080(9) C2 0.0339(13) 0.0439(14) 0.0302(13) 0.0091(11) -0.0002(11) -0.0063(11) C3 0.0383(15) 0.0444(15) 0.0466(16) 0.0029(13) -0.0001(13) -0.0146(12) C4 0.0340(14) 0.0488(16) 0.0358(15) -0.0087(12) -0.0074(12) 0.0030(12) C5 0.0506(16) 0.0551(17) 0.0262(13) 0.0051(12) -0.0025(12) 0.0009(13) C6 0.0363(14) 0.0389(14) 0.0345(14) 0.0086(11) -0.0001(11) -0.0028(11) C7 0.0162(10) 0.0216(10) 0.0266(11) 0.0038(9) 0.0005(9) 0.0047(8) C8 0.0474(15) 0.0245(12) 0.0470(15) 0.0146(11) 0.0188(12) 0.0160(11) C9 0.0595(17) 0.0287(13) 0.0628(18) 0.0090(13) 0.0303(15) 0.0224(12) C10 0.0339(13) 0.0427(14) 0.0357(14) 0.0019(11) 0.0136(11) 0.0120(11) C11 0.0227(11) 0.0441(14) 0.0323(13) 0.0167(11) 0.0043(10) 0.0137(10) C12 0.0224(11) 0.0280(12) 0.0331(13) 0.0094(10) 0.0027(10) 0.0133(9) C13 0.0183(10) 0.0213(10) 0.0261(11) 0.0059(9) 0.0052(9) 0.0041(8) C14 0.0280(12) 0.0287(12) 0.0399(14) 0.0081(10) -0.0001(11) 0.0062(10) C15 0.0230(12) 0.0515(16) 0.0528(16) 0.0183(13) -0.0033(11) 0.0094(11) C16 0.0284(13) 0.0465(16) 0.0745(19) 0.0316(14) 0.0155(13) 0.0229(12) C17 0.0449(16) 0.0298(13) 0.0694(18) 0.0077(13) 0.0168(14) 0.0222(12) C18 0.0324(13) 0.0257(12) 0.0425(14) 0.0018(10) 0.0033(11) 0.0107(10) C19 0.0312(12) 0.0170(10) 0.0236(11) 0.0020(9) -0.0023(9) -0.0015(9) C20 0.0406(14) 0.0449(15) 0.0367(14) 0.0150(12) -0.0033(12) -0.0076(12) C21 0.068(2) 0.0476(17) 0.0408(16) 0.0272(13) -0.0161(15) -0.0263(15) C22 0.066(2) 0.0304(14) 0.0599(19) 0.0127(13) -0.0324(16) -0.0012(13) C23 0.0579(17) 0.0348(14) 0.0518(17) 0.0083(13) -0.0139(14) 0.0164(13) C24 0.0435(14) 0.0300(13) 0.0361(13) 0.0076(10) -0.0024(11) 0.0116(11) C25 0.0238(11) 0.0186(10) 0.0297(12) 0.0074(9) 0.0024(9) 0.0074(9) C26 0.0277(13) 0.0403(14) 0.0402(14) 0.0110(11) 0.0067(11) 0.0072(11) C27 0.0230(12) 0.0373(14) 0.0614(18) 0.0158(13) 0.0006(12) 0.0025(10) C28 0.0357(14) 0.0289(13) 0.0486(16) 0.0034(11) -0.0172(12) 0.0069(11) C29 0.0393(14) 0.0336(13) 0.0320(13) 0.0025(10) -0.0036(11) 0.0111(11) C30 0.0262(12) 0.0231(11) 0.0327(13) 0.0052(9) 0.0012(10) 0.0074(9) C31 0.0587(17) 0.0463(15) 0.0522(16) 0.0129(13) 0.0241(14) 0.0335(14) O1 0.0279(8) 0.0216(7) 0.0292(8) 0.0072(6) 0.0029(6) 0.0061(6) O2 0.0420(9) 0.0379(9) 0.0324(9) 0.0006(7) 0.0075(7) 0.0203(8) Si1 0.0200(3) 0.0179(3) 0.0250(3) 0.0047(2) 0.0017(2) 0.0057(2) Si2 0.0251(3) 0.0209(3) 0.0242(3) 0.0041(2) 0.0046(3) 0.0071(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.381(3) . ? C1 C2 1.383(3) . ? C1 Si1 1.852(2) . ? C2 C3 1.374(3) . ? C3 C4 1.368(3) . ? C4 C5 1.370(3) . ? C5 C6 1.380(3) . ? C7 C12 1.390(3) . ? C7 C8 1.394(3) . ? C7 Si1 1.856(2) . ? C8 C9 1.371(3) . ? C9 C10 1.371(3) . ? C10 C11 1.373(3) . ? C11 C12 1.376(3) . ? C13 C14 1.384(3) . ? C13 C18 1.390(3) . ? C13 Si1 1.8630(19) . ? C14 C15 1.383(3) . ? C15 C16 1.375(3) . ? C16 C17 1.360(3) . ? C17 C18 1.383(3) . ? C19 C20 1.382(3) . ? C19 C24 1.390(3) . ? C19 Si2 1.8498(19) . ? C20 C21 1.402(3) . ? C21 C22 1.372(4) . ? C22 C23 1.350(4) . ? C23 C24 1.389(3) . ? C25 C30 1.389(3) . ? C25 C26 1.397(3) . ? C25 Si2 1.857(2) . ? C26 C27 1.382(3) . ? C27 C28 1.365(3) . ? C28 C29 1.373(3) . ? C29 C30 1.378(3) . ? C31 O2 1.434(2) . ? O1 Si2 1.6175(14) . ? O1 Si1 1.6290(14) . ? O2 Si2 1.6197(15) . ? 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 C1 C2 116.4(2) . . ? C6 C1 Si1 122.80(16) . . ? C2 C1 Si1 120.66(16) . . ? C3 C2 C1 122.1(2) . . ? C4 C3 C2 120.2(2) . . ? C3 C4 C5 119.3(2) . . ? C4 C5 C6 120.0(2) . . ? C5 C6 C1 122.0(2) . . ? C12 C7 C8 116.21(19) . . ? C12 C7 Si1 121.37(14) . . ? C8 C7 Si1 122.40(15) . . ? C9 C8 C7 121.6(2) . . ? C10 C9 C8 120.7(2) . . ? C9 C10 C11 119.2(2) . . ? C10 C11 C12 119.94(19) . . ? C11 C12 C7 122.25(18) . . ? C14 C13 C18 117.60(18) . . ? C14 C13 Si1 119.43(15) . . ? C18 C13 Si1 122.98(16) . . ? C15 C14 C13 121.4(2) . . ? C16 C15 C14 119.6(2) . . ? C17 C16 C15 120.3(2) . . ? C16 C17 C18 120.3(2) . . ? C17 C18 C13 120.9(2) . . ? C20 C19 C24 117.23(19) . . ? C20 C19 Si2 121.87(17) . . ? C24 C19 Si2 120.71(16) . . ? C19 C20 C21 120.6(2) . . ? C22 C21 C20 120.0(2) . . ? C23 C22 C21 120.6(2) . . ? C22 C23 C24 119.5(3) . . ? C23 C24 C19 122.1(2) . . ? C30 C25 C26 116.8(2) . . ? C30 C25 Si2 122.55(16) . . ? C26 C25 Si2 120.63(16) . . ? C27 C26 C25 121.5(2) . . ? C28 C27 C26 120.2(2) . . ? C27 C28 C29 119.7(2) . . ? C28 C29 C30 120.4(2) . . ? C29 C30 C25 121.5(2) . . ? Si2 O1 Si1 150.72(9) . . ? C31 O2 Si2 125.15(14) . . ? O1 Si1 C1 109.68(8) . . ? O1 Si1 C7 107.56(8) . . ? C1 Si1 C7 112.31(9) . . ? O1 Si1 C13 109.42(8) . . ? C1 Si1 C13 110.13(9) . . ? C7 Si1 C13 107.67(8) . . ? O1 Si2 O2 114.10(8) . . ? O1 Si2 C19 107.31(8) . . ? O2 Si2 C19 106.49(9) . . ? O1 Si2 C25 107.92(8) . . ? O2 Si2 C25 109.67(9) . . ? C19 Si2 C25 111.37(8) . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF