# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 2012 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_Cambridge 1326 _publ_contact_author_name 'Wong Chi Man, Michel' _publ_contact_author_email michel.wong-chi-man@enscm.fr _publ_section_title ; Investigation on the Vibrational and Structural Properties of a Self-Structured Bridged Silsesquioxane ; loop_ _publ_author_name G.Creff G.Arrachart P.Hermet H.Wadepohl R.Almairac D.Maurin ; J.-L.Sauvajol ; C.Carcel J.Moreau D.Philippe 'M.Wong Chi Man' ; J.-L.Bantignies ; # Attachment '- ex_mw1.cif' data_ex_mw1 _database_code_depnum_ccdc_archive 'CCDC 678910' #TrackingRef '- ex_mw1.cif' _audit_creation_method SHELXL-97 _audit_block_code michel _audit_block_refno ? _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H28 N4 O5 Si' _chemical_melting_point ? _exptl_crystal_description irregular _exptl_crystal_colour colourless _diffrn_ambient_temperature 100(2) _chemical_formula_weight 372.50 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_int_tables_number 148 _chemical_absolute_configuration . loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 35.463(3) _cell_length_b 35.463(3) _cell_length_c 7.8005(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8495.6(14) _cell_formula_units_Z 18 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5773 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 28.95 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3600 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6628 _exptl_absorpt_correction_T_max 0.7463 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements (Blessing 1995) SADABS (Sheldrick & Bruker AXS, 2004-2008) ; _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Smart 1000' _diffrn_measurement_method '\f- and \w-scans' _diffrn_detector_area_resol_mean 8.19 _diffrn_reflns_number 96145 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3353 _reflns_number_gt 1951 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-5.631 (Bruker AXS, 2003)' _computing_cell_refinement ; SAINT (Bruker AXS, 1997-2008). Includes estimated systematic errors of the unit cell constants from Monte Carlo simulations. ; _computing_data_reduction 'SAINT (Bruker AXS, 1997-2008); SADABS (Bruker AXS, 2008)' _computing_structure_solution 'SIR2004 (Giacovazzo et al., 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3353 _refine_ls_number_parameters 167 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.3174 _refine_ls_R_factor_gt 0.2631 _refine_ls_wR_factor_ref 0.6768 _refine_ls_wR_factor_gt 0.6365 _refine_ls_goodness_of_fit_ref 2.928 _refine_ls_restrained_S_all 2.940 _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 0.0692(3) 0.3429(3) -0.1898(9) 0.087(2) Uani 1 1 d . . . C11 C 0.0360(4) 0.2750(5) 0.3737(15) 0.098(4) Uani 1 1 d . . . H11A H 0.0281 0.2443 0.3826 0.146 Uiso 1 1 calc R . . H11B H 0.0095 0.2770 0.3663 0.146 Uiso 1 1 calc R . . H11C H 0.0527 0.2908 0.4751 0.146 Uiso 1 1 calc R . . O2 O 0.1573(2) 0.2748(2) 0.3223(7) 0.077(2) Uani 1 1 d . . . N1 N 0.1020(3) 0.2958(2) 0.2060(9) 0.063(2) Uani 1 1 d . . . H1 H 0.1104 0.2859 0.2928 0.076 Uiso 1 1 calc R . . N2 N 0.1166(3) 0.3264(3) -0.0685(10) 0.076(3) Uani 1 1 d . . . N3 N 0.1652(3) 0.3106(3) 0.0636(8) 0.067(2) Uani 1 1 d . . . H3 H 0.1830 0.3237 -0.0227 0.080 Uiso 1 1 calc R . . N4 N 0.2148(3) 0.2896(3) 0.1424(9) 0.070(2) Uani 1 1 d . . . H4N H 0.2290 0.3029 0.0486 0.085 Uiso 1 1 calc R . . C1 C 0.0634(3) 0.2947(3) 0.2139(12) 0.071(3) Uani 1 1 d . . . C2 C 0.1280(3) 0.3119(3) 0.0655(9) 0.060(2) Uani 1 1 d . . . C3 C 0.0790(4) 0.3268(4) -0.0678(12) 0.074(3) Uani 1 1 d . . . C4 C 0.0509(4) 0.3118(3) 0.0818(12) 0.076(3) Uani 1 1 d . . . H4 H 0.0251 0.3137 0.0881 0.091 Uiso 1 1 calc R . . C5 C 0.1784(4) 0.2908(3) 0.1834(11) 0.069(3) Uani 1 1 d . . . C6 C 0.2318(4) 0.2670(4) 0.2478(14) 0.086(3) Uani 1 1 d D . . H6A H 0.2094 0.2491 0.3340 0.103 Uiso 1 1 calc R . . H6B H 0.2577 0.2891 0.3108 0.103 Uiso 1 1 calc R . . Si1 Si 0.1829(3) 0.1367(3) 0.0730(11) 0.182(3) Uiso 1 1 d D . . O4 O 0.1374(5) 0.1086(6) 0.168(2) 0.197(7) Uiso 1 1 d D . . C31 C 0.2316(6) 0.1182(5) 0.2767(19) 0.120(5) Uiso 1 1 d D . . H31A H 0.2166 0.1257 0.3660 0.144 Uiso 1 1 calc R . . H31B H 0.2633 0.1377 0.2913 0.144 Uiso 1 1 calc R . . C32 C 0.2207(7) 0.0713(5) 0.302(3) 0.145(6) Uiso 1 1 d D . . H32A H 0.2021 0.0533 0.2081 0.218 Uiso 1 1 calc R . . H32B H 0.2055 0.0604 0.4113 0.218 Uiso 1 1 calc R . . H32C H 0.2477 0.0700 0.3031 0.218 Uiso 1 1 calc R . . O3 O 0.2196(6) 0.1251(6) 0.120(2) 0.215(7) Uiso 1 1 d D . . O5 O 0.1773(6) 0.1362(8) -0.131(2) 0.271(11) Uiso 1 1 d D . . C51 C 0.1767(7) 0.1099(8) -0.259(3) 0.164(8) Uiso 1 1 d D . . H51A H 0.1913 0.0937 -0.2231 0.197 Uiso 1 1 calc R . . H51B H 0.1915 0.1273 -0.3627 0.197 Uiso 1 1 calc R . . C7 C 0.2445(11) 0.2374(12) 0.150(11) 0.52(5) Uiso 1 1 d D . . H7A H 0.2568 0.2498 0.0357 0.625 Uiso 1 1 calc R . . H7B H 0.2662 0.2334 0.2147 0.625 Uiso 1 1 calc R . . C52 C 0.1280(12) 0.078(2) -0.297(13) 0.59(7) Uiso 1 1 d D . . H52A H 0.1106 0.0904 -0.2512 0.882 Uiso 1 1 calc R . . H52B H 0.1191 0.0502 -0.2418 0.882 Uiso 1 1 calc R . . H52C H 0.1236 0.0741 -0.4208 0.882 Uiso 1 1 calc R . . C41 C 0.1086(10) 0.0651(7) 0.175(4) 0.227(12) Uiso 1 1 d D . . H41A H 0.1232 0.0511 0.2330 0.272 Uiso 1 1 calc R . . H41B H 0.1026 0.0540 0.0555 0.272 Uiso 1 1 calc R . . C42 C 0.0645(11) 0.0496(14) 0.264(5) 0.295(19) Uiso 1 1 d D . . H42A H 0.0506 0.0651 0.2157 0.442 Uiso 1 1 calc R . . H42B H 0.0693 0.0556 0.3871 0.442 Uiso 1 1 calc R . . H42C H 0.0458 0.0182 0.2459 0.442 Uiso 1 1 calc R . . C8 C 0.2015(11) 0.1941(6) 0.132(5) 0.31(2) Uiso 1 1 d D . . H8A H 0.1846 0.2018 0.0520 0.376 Uiso 1 1 calc R . . H8B H 0.1877 0.1911 0.2450 0.376 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 0.091(5) 0.121(6) 0.061(4) 0.025(4) 0.018(3) 0.062(5) C11 0.081(8) 0.124(10) 0.071(7) 0.035(6) 0.031(6) 0.039(7) O2 0.096(5) 0.100(5) 0.041(3) 0.006(3) 0.008(3) 0.053(4) N1 0.070(5) 0.068(5) 0.044(4) 0.001(3) 0.008(3) 0.029(4) N2 0.090(6) 0.107(7) 0.048(4) 0.017(4) 0.017(4) 0.062(5) N3 0.083(6) 0.087(6) 0.033(3) 0.007(3) 0.004(3) 0.044(5) N4 0.081(6) 0.084(6) 0.046(4) 0.004(4) 0.000(4) 0.041(5) C1 0.070(7) 0.072(6) 0.059(6) 0.009(4) 0.017(5) 0.026(5) C2 0.070(6) 0.074(6) 0.032(4) 0.001(4) 0.009(4) 0.032(5) C3 0.088(7) 0.098(8) 0.052(5) 0.012(5) 0.013(5) 0.058(6) C4 0.080(7) 0.083(7) 0.055(6) 0.005(5) 0.020(5) 0.033(6) C5 0.086(7) 0.074(6) 0.044(5) -0.004(4) 0.001(5) 0.038(6) C6 0.116(9) 0.084(7) 0.065(6) -0.010(5) -0.008(6) 0.056(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 O1 C3 1.244(12) . ? C11 C1 1.519(13) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? O2 C5 1.278(11) . ? N1 C1 1.354(13) . ? N1 C2 1.361(11) . ? N1 H1 0.8800 . ? N2 C2 1.316(12) . ? N2 C3 1.342(14) . ? N3 C2 1.340(12) . ? N3 C5 1.383(13) . ? N3 H3 0.8800 . ? N4 C5 1.353(13) . ? N4 C6 1.471(15) . ? N4 H4N 0.8800 . ? C1 C4 1.377(15) . ? C3 C4 1.452(14) . ? C4 H4 0.9500 . ? C6 C7 1.538(10) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? Si1 O3 1.592(14) . ? Si1 O4 1.594(14) . ? Si1 O5 1.604(15) . ? Si1 C8 1.856(10) . ? O4 C41 1.360(16) . ? C31 O3 1.356(15) . ? C31 C32 1.519(9) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? O5 C51 1.358(16) . ? C51 C52 1.543(10) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C7 C8 1.537(10) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C41 C42 1.540(10) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? 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 C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 N1 C2 120.9(8) . . ? C1 N1 H1 119.6 . . ? C2 N1 H1 119.6 . . ? C2 N2 C3 120.2(8) . . ? C2 N3 C5 126.6(8) . . ? C2 N3 H3 116.7 . . ? C5 N3 H3 116.7 . . ? C5 N4 C6 122.9(9) . . ? C5 N4 H4N 118.5 . . ? C6 N4 H4N 118.5 . . ? N1 C1 C4 119.9(8) . . ? N1 C1 C11 117.0(9) . . ? C4 C1 C11 123.0(10) . . ? N2 C2 N3 120.3(7) . . ? N2 C2 N1 121.8(9) . . ? N3 C2 N1 117.8(8) . . ? O1 C3 N2 120.5(9) . . ? O1 C3 C4 119.0(10) . . ? N2 C3 C4 120.3(9) . . ? C1 C4 C3 116.7(10) . . ? C1 C4 H4 121.7 . . ? C3 C4 H4 121.7 . . ? O2 C5 N4 122.8(9) . . ? O2 C5 N3 121.9(9) . . ? N4 C5 N3 115.3(8) . . ? N4 C6 C7 116(4) . . ? N4 C6 H6A 108.4 . . ? C7 C6 H6A 108.4 . . ? N4 C6 H6B 108.4 . . ? C7 C6 H6B 108.4 . . ? H6A C6 H6B 107.4 . . ? O3 Si1 O4 115.8(8) . . ? O3 Si1 O5 109.7(8) . . ? O4 Si1 O5 111.9(8) . . ? O3 Si1 C8 109.9(11) . . ? O4 Si1 C8 105.3(12) . . ? O5 Si1 C8 103.4(12) . . ? C41 O4 Si1 132.7(19) . . ? O3 C31 C32 112.6(15) . . ? O3 C31 H31A 109.1 . . ? C32 C31 H31A 109.1 . . ? O3 C31 H31B 109.1 . . ? C32 C31 H31B 109.1 . . ? H31A C31 H31B 107.8 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 O3 Si1 128.7(14) . . ? C51 O5 Si1 134(2) . . ? O5 C51 C52 106(4) . . ? O5 C51 H51A 110.6 . . ? C52 C51 H51A 110.6 . . ? O5 C51 H51B 110.6 . . ? C52 C51 H51B 110.6 . . ? H51A C51 H51B 108.8 . . ? C8 C7 C6 104.0(13) . . ? C8 C7 H7A 111.0 . . ? C6 C7 H7A 111.0 . . ? C8 C7 H7B 111.0 . . ? C6 C7 H7B 111.0 . . ? H7A C7 H7B 109.0 . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? O4 C41 C42 118(3) . . ? O4 C41 H41A 107.7 . . ? C42 C41 H41A 107.7 . . ? O4 C41 H41B 107.7 . . ? C42 C41 H41B 107.7 . . ? H41A C41 H41B 107.1 . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C7 C8 Si1 138(2) . . ? C7 C8 H8A 102.5 . . ? Si1 C8 H8A 102.5 . . ? C7 C8 H8B 102.5 . . ? Si1 C8 H8B 102.5 . . ? H8A C8 H8B 104.9 . . ? 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 C2 N1 C1 C4 -2.7(14) . . . . ? C2 N1 C1 C11 178.2(10) . . . . ? C3 N2 C2 N3 178.6(9) . . . . ? C3 N2 C2 N1 1.9(15) . . . . ? C5 N3 C2 N2 -170.3(9) . . . . ? C5 N3 C2 N1 6.5(14) . . . . ? C1 N1 C2 N2 -1.1(14) . . . . ? C1 N1 C2 N3 -177.9(9) . . . . ? C2 N2 C3 O1 175.7(10) . . . . ? C2 N2 C3 C4 0.9(16) . . . . ? N1 C1 C4 C3 5.3(14) . . . . ? C11 C1 C4 C3 -175.7(11) . . . . ? O1 C3 C4 C1 -179.3(10) . . . . ? N2 C3 C4 C1 -4.5(15) . . . . ? C6 N4 C5 O2 4.4(15) . . . . ? C6 N4 C5 N3 -175.2(9) . . . . ? C2 N3 C5 O2 -7.2(15) . . . . ? C2 N3 C5 N4 172.4(9) . . . . ? C5 N4 C6 C7 133.0(16) . . . . ? O3 Si1 O4 C41 -58(3) . . . . ? O5 Si1 O4 C41 69(3) . . . . ? C8 Si1 O4 C41 -180(3) . . . . ? C32 C31 O3 Si1 112.9(19) . . . . ? O4 Si1 O3 C31 -45(2) . . . . ? O5 Si1 O3 C31 -173.3(18) . . . . ? C8 Si1 O3 C31 74(2) . . . . ? O3 Si1 O5 C51 41(3) . . . . ? O4 Si1 O5 C51 -89(2) . . . . ? C8 Si1 O5 C51 158(3) . . . . ? Si1 O5 C51 C52 98(4) . . . . ? N4 C6 C7 C8 -84(5) . . . . ? Si1 O4 C41 C42 -173(2) . . . . ? C6 C7 C8 Si1 -166(3) . . . . ? O3 Si1 C8 C7 28(6) . . . . ? O4 Si1 C8 C7 154(6) . . . . ? O5 Si1 C8 C7 -89(6) . . . . ? 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 N1 H1 O2 0.88 1.90 2.584(11) 132.8 . N4 H4N O1 0.88 1.85 2.718(11) 168.1 16_554 N3 H3 N2 0.88 2.15 3.014(11) 165.6 16_554 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.734 _refine_diff_density_min -0.774 _refine_diff_density_rms 0.208 _diffrn_ambient_environment 'perfluoro polyether oil' _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_specimen_support 'polyimid foil' _diffrn_detector 'CCD plate' _diffrn_detector_type CCD-PXL-KAF2 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' # Attachment '- ex_mw1_sq.cif' data_ex_mw1_sq _database_code_depnum_ccdc_archive 'CCDC 864842' #TrackingRef '- ex_mw1_sq.cif' _audit_creation_method SHELXL-97 _audit_block_code michel _audit_block_refno ? _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H28 N4 O5 Si' _chemical_melting_point ? _exptl_crystal_description irregular _exptl_crystal_colour colourless _diffrn_ambient_temperature 100(2) _chemical_formula_weight 372.50 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_int_tables_number 148 _chemical_absolute_configuration . loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 35.463(3) _cell_length_b 35.463(3) _cell_length_c 7.8005(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8495.6(14) _cell_formula_units_Z 18 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5773 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 28.95 _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3600 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6628 _exptl_absorpt_correction_T_max 0.7463 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements (Blessing 1995) SADABS (Sheldrick & Bruker AXS, 2004-2008) ; _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Smart 1000' _diffrn_measurement_method '\f- and \w-scans' _diffrn_detector_area_resol_mean 8.19 _diffrn_reflns_number 96145 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3353 _reflns_number_gt 1747 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-5.631 (Bruker AXS, 2003)' _computing_cell_refinement ; SAINT (Bruker AXS, 1997-2008). Includes estimated systematic errors of the unit cell constants from Monte Carlo simulations. ; _computing_data_reduction 'SAINT (Bruker AXS, 1997-2008); SADABS (Bruker AXS, 2008)' _computing_structure_solution 'SIR2004 (Giacovazzo et al., 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3353 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1664 _refine_ls_R_factor_gt 0.1302 _refine_ls_wR_factor_ref 0.3893 _refine_ls_wR_factor_gt 0.3633 _refine_ls_goodness_of_fit_ref 1.305 _refine_ls_restrained_S_all 1.305 _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 0.06883(11) 0.34286(13) -0.1907(4) 0.0896(11) Uani 1 1 d . . . C11 C 0.03727(18) 0.27599(19) 0.3750(6) 0.0902(16) Uani 1 1 d . . . H11A H 0.0256 0.2444 0.3749 0.135 Uiso 1 1 calc R . . H11B H 0.0132 0.2821 0.3789 0.135 Uiso 1 1 calc R . . H11C H 0.0559 0.2888 0.4756 0.135 Uiso 1 1 calc R . . O2 O 0.15742(10) 0.27565(10) 0.3192(3) 0.0730(10) Uani 1 1 d . . . N1 N 0.10214(11) 0.29600(11) 0.2047(4) 0.0651(10) Uani 1 1 d . . . H1 H 0.1108 0.2863 0.2914 0.078 Uiso 1 1 calc R . . N2 N 0.11788(12) 0.32724(13) -0.0675(4) 0.0701(11) Uani 1 1 d . . . N3 N 0.16516(12) 0.31031(12) 0.0627(4) 0.0676(11) Uani 1 1 d . . . H3 H 0.1830 0.3234 -0.0234 0.081 Uiso 1 1 calc R . . N4 N 0.21372(13) 0.28921(12) 0.1436(4) 0.0720(11) Uani 1 1 d . . . H4N H 0.2274 0.3023 0.0487 0.086 Uiso 1 1 calc R . . C1 C 0.06331(15) 0.29524(15) 0.2159(5) 0.0684(12) Uani 1 1 d . . . C2 C 0.12754(14) 0.31113(14) 0.0646(4) 0.0612(11) Uani 1 1 d . . . C3 C 0.07881(17) 0.32759(18) -0.0665(6) 0.0795(14) Uani 1 1 d . . . C4 C 0.05166(17) 0.31145(16) 0.0824(5) 0.0776(13) Uani 1 1 d . . . H4 H 0.0253 0.3121 0.0873 0.093 Uiso 1 1 calc R . . C5 C 0.17812(15) 0.29059(14) 0.1847(5) 0.0655(12) Uani 1 1 d . . . C6 C 0.2317(2) 0.26746(17) 0.2455(6) 0.0885(16) Uani 1 1 d . . . H6A H 0.2093 0.2495 0.3316 0.106 Uiso 1 1 d R . . H6B H 0.2576 0.2896 0.3084 0.106 Uiso 1 1 d 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 0.095(2) 0.128(3) 0.0570(19) 0.0249(18) 0.0164(15) 0.064(2) C11 0.086(3) 0.108(4) 0.065(3) 0.028(3) 0.028(2) 0.040(3) O2 0.089(2) 0.089(2) 0.0388(14) 0.0066(13) 0.0066(13) 0.0421(17) N1 0.074(2) 0.074(2) 0.0385(17) 0.0035(14) 0.0085(15) 0.0301(19) N2 0.074(2) 0.106(3) 0.0419(17) 0.0093(17) 0.0095(15) 0.054(2) N3 0.079(2) 0.094(3) 0.0319(15) 0.0063(15) 0.0062(15) 0.044(2) N4 0.089(3) 0.092(3) 0.0385(17) 0.0018(16) -0.0053(17) 0.049(2) C1 0.071(3) 0.075(3) 0.048(2) 0.0054(19) 0.0110(19) 0.028(2) C2 0.068(3) 0.082(3) 0.0323(18) 0.0032(17) 0.0072(17) 0.037(2) C3 0.095(4) 0.108(4) 0.052(2) 0.005(2) 0.007(2) 0.063(3) C4 0.083(3) 0.085(3) 0.060(3) 0.008(2) 0.021(2) 0.038(3) C5 0.073(3) 0.080(3) 0.039(2) -0.0009(19) -0.0013(19) 0.035(2) C6 0.128(4) 0.079(3) 0.065(3) -0.007(2) -0.009(3) 0.056(3) _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 C3 1.245(5) . ? C11 C1 1.493(6) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? O2 C5 1.238(5) . ? N1 C2 1.345(5) . ? N1 C1 1.367(6) . ? N1 H1 0.8800 . ? N2 C2 1.304(5) . ? N2 C3 1.392(6) . ? N3 C2 1.349(5) . ? N3 C5 1.388(5) . ? N3 H3 0.8800 . ? N4 C5 1.327(6) . ? N4 C6 1.456(6) . ? N4 H4N 0.8800 . ? C1 C4 1.350(6) . ? C3 C4 1.433(6) . ? C4 H4 0.9500 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? 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 C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C2 N1 C1 121.8(4) . . ? C2 N1 H1 119.1 . . ? C1 N1 H1 119.1 . . ? C2 N2 C3 118.7(3) . . ? C2 N3 C5 125.7(3) . . ? C2 N3 H3 117.2 . . ? C5 N3 H3 117.2 . . ? C5 N4 C6 124.3(4) . . ? C5 N4 H4N 117.8 . . ? C6 N4 H4N 117.8 . . ? C4 C1 N1 117.5(4) . . ? C4 C1 C11 125.8(5) . . ? N1 C1 C11 116.7(4) . . ? N2 C2 N1 123.1(4) . . ? N2 C2 N3 118.7(3) . . ? N1 C2 N3 118.2(3) . . ? O1 C3 N2 120.0(4) . . ? O1 C3 C4 121.6(5) . . ? N2 C3 C4 118.3(4) . . ? C1 C4 C3 120.5(5) . . ? C1 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? O2 C5 N4 124.1(4) . . ? O2 C5 N3 121.5(4) . . ? N4 C5 N3 114.5(3) . . ? N4 C6 H6A 106.8 . . ? N4 C6 H6B 109.2 . . ? H6A C6 H6B 107.4 . . ? 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 C2 N1 C1 C4 -1.8(6) . . . . ? C2 N1 C1 C11 177.6(4) . . . . ? C3 N2 C2 N1 -2.1(7) . . . . ? C3 N2 C2 N3 179.2(4) . . . . ? C1 N1 C2 N2 2.1(6) . . . . ? C1 N1 C2 N3 -179.2(4) . . . . ? C5 N3 C2 N2 -173.4(4) . . . . ? C5 N3 C2 N1 7.9(6) . . . . ? C2 N2 C3 O1 179.8(4) . . . . ? C2 N2 C3 C4 2.0(7) . . . . ? N1 C1 C4 C3 1.7(7) . . . . ? C11 C1 C4 C3 -177.6(5) . . . . ? O1 C3 C4 C1 -179.7(5) . . . . ? N2 C3 C4 C1 -1.8(7) . . . . ? C6 N4 C5 O2 4.3(7) . . . . ? C6 N4 C5 N3 -175.4(4) . . . . ? C2 N3 C5 O2 -8.1(6) . . . . ? C2 N3 C5 N4 171.6(4) . . . . ? 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 N1 H1 O2 0.88 1.88 2.564(5) 132.7 . N4 H4N O1 0.88 1.88 2.743(5) 166.2 16_554 N3 H3 N2 0.88 2.14 2.995(4) 164.9 16_554 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.350 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.105 _diffrn_ambient_environment 'perfluoro polyether oil' _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_specimen_support 'polyimid foil' _diffrn_detector 'CCD plate' _diffrn_detector_type CCD-PXL-KAF2 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' # SQUEEZE RESULTS (APPEND TO CIF) # Ref.: P. v. d. Sluis, A. L. Spek, Acta Cryst. 1990, A46, 194. # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.012 1658 577 ' ' 2 0.333 0.667 0.352 1659 577 ' ' 3 0.667 0.333 0.019 1659 577 ' ' _platon_squeeze_details ; ;