Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2002 data_global _audit_creation_method 'SHELXL and manual editing' _journal_coden_Cambridge 188 loop_ _publ_author_name _publ_author_address 'Paul C. Bell' ; Department of Chemistry and Physics Nottingham Trent University Clifton Lane Nottingham UK NG11 8NS ; 'Wolfgang Skranc' ; Department of Chemistry and Physics Nottingham Trent University Clifton Lane Nottingham UK NG11 8NS ; 'Xavier Formosa' ; Department of Chemistry and Physics Nottingham Trent University Clifton Lane Nottingham UK NG11 8NS ; ; Jane O'Leary ; ; Department of Chemistry and Physics Nottingham Trent University Clifton Lane Nottingham UK NG11 8NS ; 'John D. Wallis' ; Department of Chemistry and Physics Nottingham Trent University Clifton Lane Nottingham UK NG11 8NS ; _publ_contact_author_name 'Dr J Wallis' _publ_contact_author_address ; Chemistry and Physics The Nottingham Trent University Clifton Lane Nottingham NG11 8NS UK ; _publ_contact_author_email john.wallis@ntu.ac.uk _publ_contact_author_fax 0115-948-6636 _publ_contact_author_phone 0115-848-3149 _publ_requested_journal 'JCS Perkin Trans 2' _publ_section_title ; Interactions Between Alkynes and Methoxy or Dimethylamino Groups in Peri-Naphthalene Systems ; # TEXT _publ_section_references ; Blessing, R.H. (1995). Acta Cryst., A51, 33-38. Hooft, R. (1998). Data Collection Software, Nonius B.V., Delft, The Netherlands. Johnson, C.K., Burnett, M.N. (1996). ORTEPIII Report ORNL-6895, Oak Ridge National Laboratory, Tennessee, USA Otwinowski, M., Minor W. (1997). Methods in Enzymology 276: macromolecular crystallography A, ed. Carter, C.W. Jr, Sweet, R.M., Academic Press, 307-326. Sheldrick, G.M. (1990). Acta Cryst. A46, 467-473. Sheldrick, G.M. (1993). SHELXL-93 Program for the Refinement of Crystal Structures, University of Gottingen, Germany. ; _publ_section_exptl_refinement ; The structures were solved using direct methods and refined with the full-matrix least-squares technique. All non-hydrogen atoms were refined with anisotropic displacement parameters, all hydrogen atoms were located in diffence fourier maps and their positions and isotropic displacement parameters refined unless otherwise stated. ; data_acet-14 _database_code_CSD 178491 _audit_creation_method SHELXL _chemical_name_systematic ; 1-ethynyl-8-methoxynaphthalene ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H10 O' _chemical_formula_weight 182.21 _chemical_melting_point 339-340 _chemical_compound_source ? 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 6.03190(10) _cell_length_b 10.3050(4) _cell_length_c 30.3610(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1887.20(11) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1978 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 27.50 _exptl_crystal_description plates _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method ? _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.895 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R. H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKa _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13043 _diffrn_reflns_av_R_equivalents 0.0798 _diffrn_reflns_av_sigmaI/netI 0.0594 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2153 _reflns_number_observed 1410 _reflns_observed_criterion >2sigma(I) _computing_data_collection ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_cell_refinement ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_data_reduction ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEP3 (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 175 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[s^2^(Fo^2^)+( 0.0728P)^2^+0.0515P] 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 ? _refine_ls_number_reflns 1978 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0925 _refine_ls_R_factor_obs 0.0535 _refine_ls_wR_factor_all 0.1421 _refine_ls_wR_factor_obs 0.1256 _refine_ls_goodness_of_fit_all 1.049 _refine_ls_goodness_of_fit_obs 1.167 _refine_ls_restrained_S_all 1.048 _refine_ls_restrained_S_obs 1.167 _refine_ls_shift/esd_max -0.110 _refine_ls_shift/esd_mean 0.008 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.1582(2) 0.02980(12) 0.17549(4) 0.0348(4) Uani 1 d . . C1 C 0.1704(2) 0.0033(2) 0.13129(5) 0.0241(4) Uani 1 d . . C2 C 0.3311(3) 0.0531(2) 0.10415(6) 0.0293(4) Uani 1 d . . C3 C 0.3332(3) 0.0225(2) 0.05911(6) 0.0316(5) Uani 1 d . . C4 C 0.1767(3) -0.0566(2) 0.04138(6) 0.0287(4) Uani 1 d . . C5 C -0.1564(3) -0.1914(2) 0.04968(6) 0.0277(4) Uani 1 d . . C6 C -0.3181(3) -0.2449(2) 0.07495(6) 0.0307(4) Uani 1 d . . C7 C -0.3249(3) -0.2187(2) 0.12021(6) 0.0289(4) Uani 1 d . . C8 C -0.1717(2) -0.1380(2) 0.14008(5) 0.0239(4) Uani 1 d . . C9 C 0.0077(3) -0.1100(2) 0.06835(5) 0.0243(4) Uani 1 d . . C10 C 0.0020(2) -0.0813(2) 0.11429(5) 0.0223(4) Uani 1 d . . C11 C -0.1996(3) -0.1180(2) 0.18651(5) 0.0272(4) Uani 1 d . . C12 C -0.2530(3) -0.1139(2) 0.22425(6) 0.0386(5) Uani 1 d . . C18 C 0.3044(4) 0.1239(2) 0.19320(7) 0.0401(5) Uani 1 d . . H2 H 0.4456(29) 0.1065(18) 0.1168(6) 0.035(5) Uiso 1 d . . H3 H 0.4497(30) 0.0589(18) 0.0402(6) 0.038(5) Uiso 1 d . . H4 H 0.1768(27) -0.0781(18) 0.0105(7) 0.039(5) Uiso 1 d . . H5 H -0.1470(26) -0.2046(18) 0.0193(7) 0.037(5) Uiso 1 d . . H6 H -0.4251(28) -0.3052(18) 0.0627(6) 0.034(5) Uiso 1 d . . H7 H -0.4329(26) -0.2587(18) 0.1398(6) 0.031(5) Uiso 1 d . . H12 H -0.2873(35) -0.1079(22) 0.2547(8) 0.068(7) Uiso 1 d . . H18A H 0.4651(36) 0.0962(21) 0.1889(7) 0.053(6) Uiso 1 d . . H18B H 0.2626(27) 0.1264(18) 0.2236(6) 0.035(5) Uiso 1 d . . H18C H 0.2865(29) 0.2100(20) 0.1769(6) 0.042(5) Uiso 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 O1 0.0436(8) 0.0366(8) 0.0243(7) -0.0015(5) -0.0037(5) -0.0080(6) C1 0.0281(9) 0.0217(9) 0.0224(9) -0.0005(7) -0.0024(6) 0.0029(7) C2 0.0267(10) 0.0257(10) 0.0355(10) -0.0006(8) -0.0016(8) -0.0017(8) C3 0.0312(10) 0.0303(11) 0.0333(10) 0.0037(8) 0.0081(8) 0.0001(8) C4 0.0349(10) 0.0270(10) 0.0243(9) -0.0001(7) 0.0038(7) 0.0048(8) C5 0.0345(10) 0.0257(10) 0.0228(9) -0.0018(7) -0.0033(8) 0.0037(8) C6 0.0311(10) 0.0281(10) 0.0328(10) -0.0023(8) -0.0059(8) -0.0018(8) C7 0.0283(10) 0.0276(10) 0.0309(10) 0.0010(8) 0.0015(7) -0.0013(8) C8 0.0260(8) 0.0221(9) 0.0234(9) 0.0001(7) -0.0002(6) 0.0031(7) C9 0.0280(9) 0.0203(9) 0.0247(8) 0.0002(7) -0.0004(7) 0.0061(7) C10 0.0240(8) 0.0184(9) 0.0244(8) 0.0014(7) -0.0016(6) 0.0044(7) C11 0.0305(9) 0.0233(9) 0.0277(9) 0.0009(7) -0.0016(7) 0.0026(8) C12 0.0412(11) 0.0430(13) 0.0316(10) 0.0035(10) 0.0056(9) 0.0005(9) C18 0.0503(13) 0.0341(13) 0.0359(11) -0.0043(10) -0.0122(9) -0.0077(10) _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 C1 1.371(2) . ? O1 C18 1.416(2) . ? C1 C2 1.372(2) . ? C1 C10 1.435(2) . ? C2 C3 1.403(2) . ? C3 C4 1.358(2) . ? C4 C9 1.419(2) . ? C5 C6 1.358(2) . ? C5 C9 1.416(2) . ? C6 C7 1.401(2) . ? C7 C8 1.382(2) . ? C8 C10 1.432(2) . ? C8 C11 1.435(2) . ? C9 C10 1.426(2) . ? C11 C12 1.191(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 C1 O1 C18 118.32(14) . . ? O1 C1 C2 123.45(15) . . ? O1 C1 C10 115.78(13) . . ? C2 C1 C10 120.78(15) . . ? C1 C2 C3 120.5(2) . . ? C4 C3 C2 121.0(2) . . ? C3 C4 C9 120.2(2) . . ? C6 C5 C9 121.1(2) . . ? C5 C6 C7 119.8(2) . . ? C8 C7 C6 121.6(2) . . ? C7 C8 C10 119.72(15) . . ? C7 C8 C11 115.91(14) . . ? C10 C8 C11 124.37(14) . . ? C5 C9 C4 120.1(2) . . ? C5 C9 C10 119.82(14) . . ? C4 C9 C10 120.10(15) . . ? C9 C10 C8 117.91(14) . . ? C9 C10 C1 117.41(14) . . ? C8 C10 C1 124.68(14) . . ? C12 C11 C8 169.2(2) . . ? _refine_diff_density_max 0.366 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.051 #===END data_Meotriphsilyl-15 _database_code_CSD 178492 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 8-methoxy-1-triphenylsilylethenylnaphthalene ; _chemical_name_common ? _chemical_melting_point 369-373 _chemical_formula_moiety ? _chemical_formula_sum 'C31 H24 O Si' _chemical_formula_weight 440.59 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' '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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.410 _cell_length_b 13.761 _cell_length_c 16.352 _cell_angle_alpha 93.97 _cell_angle_beta 98.58 _cell_angle_gamma 106.71 _cell_volume 2414.2 _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 14825 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 25.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96314 _exptl_absorpt_correction_T_max 0.98327 _exptl_absorpt_process_details ; using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) See R.H. Blessing, Acta Cryst., (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24409 _diffrn_reflns_av_R_equivalents 0.0898 _diffrn_reflns_av_sigmaI/netI 0.1158 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 25.07 _reflns_number_total 8349 _reflns_number_gt 4778 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1998)' _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. One phenyl ring of molecule B is disordered, and this is related to the the occurrence of a molecule of methanol, close to a centre of symmetry in a fraction of the unit cells. ; _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^)+(0.0556P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8349 _refine_ls_number_parameters 805 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.1280 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1302 _refine_ls_wR_factor_gt 0.1115 _refine_ls_goodness_of_fit_ref 0.925 _refine_ls_restrained_S_all 0.928 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 0.08187(7) 0.68647(6) 0.23121(5) 0.0310(2) Uani 1 1 d . . . O1A O 0.27489(18) 0.93843(16) 0.07709(14) 0.0432(6) Uani 1 1 d . . . C1A C 0.2325(3) 0.9679(2) 0.0030(2) 0.0368(8) Uani 1 1 d . . . C2A C 0.3051(4) 1.0399(3) -0.0376(3) 0.0488(10) Uani 1 1 d . . . C3A C 0.2548(4) 1.0686(3) -0.1118(3) 0.0568(11) Uani 1 1 d . . . C4A C 0.1328(4) 1.0272(3) -0.1443(2) 0.0481(9) Uani 1 1 d . . . C5A C -0.0742(3) 0.9134(2) -0.13692(19) 0.0359(7) Uani 1 1 d . . . C6A C -0.1513(3) 0.8433(2) -0.09895(18) 0.0349(7) Uani 1 1 d . . . C7A C -0.1023(3) 0.8096(2) -0.02681(18) 0.0304(7) Uani 1 1 d . . . C8A C 0.0221(3) 0.8448(2) 0.00776(16) 0.0274(7) Uani 1 1 d . . . C9A C 0.1047(3) 0.9209(2) -0.02987(18) 0.0319(7) Uani 1 1 d . . . C10A C 0.0537(3) 0.9531(2) -0.10464(18) 0.0360(8) Uani 1 1 d . . . C11A C 0.0586(3) 0.7993(2) 0.08025(18) 0.0308(7) Uani 1 1 d . . . C12A C 0.0707(3) 0.7507(2) 0.13852(19) 0.0326(7) Uani 1 1 d . . . C13A C 0.0064(3) 0.5460(2) 0.20457(19) 0.0358(7) Uani 1 1 d . . . C14A C -0.0082(3) 0.4962(3) 0.1249(2) 0.0416(8) Uani 1 1 d . . . C15A C -0.0615(3) 0.3911(3) 0.1072(3) 0.0549(10) Uani 1 1 d . . . C16A C -0.0996(4) 0.3332(3) 0.1678(3) 0.0570(10) Uani 1 1 d . . . C17A C -0.0874(4) 0.3797(3) 0.2467(3) 0.0648(11) Uani 1 1 d . . . C18A C -0.0368(4) 0.4847(3) 0.2650(3) 0.0543(10) Uani 1 1 d . . . C19A C 0.2481(3) 0.7141(2) 0.28008(17) 0.0328(7) Uani 1 1 d . . . C20A C 0.2995(3) 0.6401(3) 0.30905(19) 0.0428(8) Uani 1 1 d . . . C21A C 0.4223(3) 0.6648(4) 0.3488(2) 0.0576(11) Uani 1 1 d . . . C22A C 0.4952(4) 0.7658(4) 0.3603(2) 0.0580(12) Uani 1 1 d . . . C23A C 0.4482(3) 0.8412(4) 0.3325(2) 0.0544(10) Uani 1 1 d . . . C24A C 0.3256(3) 0.8152(3) 0.2930(2) 0.0443(8) Uani 1 1 d . . . C25A C 0.0033(3) 0.7413(2) 0.30652(17) 0.0302(7) Uani 1 1 d . . . C26A C -0.0981(3) 0.7754(2) 0.2795(2) 0.0344(7) Uani 1 1 d . . . C27A C -0.1569(3) 0.8166(2) 0.3347(2) 0.0394(8) Uani 1 1 d . . . C28A C -0.1156(3) 0.8243(2) 0.4190(2) 0.0421(8) Uani 1 1 d . . . C29A C -0.0152(3) 0.7912(3) 0.4481(2) 0.0412(8) Uani 1 1 d . . . C30A C 0.0434(3) 0.7508(2) 0.39211(19) 0.0351(7) Uani 1 1 d . . . C31A C 0.3979(3) 0.9925(3) 0.1194(3) 0.0552(10) Uani 1 1 d . . . Si2 Si 0.50811(8) 0.25034(6) 0.31477(5) 0.0341(2) Uani 1 1 d . . . O1B O 0.35935(19) 0.39077(15) 0.10725(13) 0.0439(6) Uani 1 1 d . . . C1B C 0.3664(3) 0.3940(2) 0.02549(19) 0.0350(7) Uani 1 1 d . . . C2B C 0.2998(3) 0.4398(2) -0.0278(2) 0.0430(8) Uani 1 1 d . . . C3B C 0.3132(3) 0.4387(3) -0.1116(2) 0.0487(9) Uani 1 1 d . . . C4B C 0.3921(3) 0.3937(3) -0.1417(2) 0.0436(8) Uani 1 1 d . . . C5B C 0.5468(3) 0.3024(2) -0.1189(2) 0.0357(7) Uani 1 1 d . . . C6B C 0.6186(3) 0.2593(2) -0.06857(19) 0.0368(8) Uani 1 1 d . . . C7B C 0.6048(3) 0.2539(2) 0.01548(18) 0.0312(7) Uani 1 1 d . . . C8B C 0.5221(2) 0.2948(2) 0.04807(16) 0.0278(7) Uani 1 1 d . A . C9B C 0.4489(2) 0.3449(2) -0.00381(17) 0.0284(7) Uani 1 1 d . . . C10B C 0.4625(3) 0.3466(2) -0.08840(17) 0.0327(7) Uani 1 1 d . . . C11B C 0.5122(3) 0.2814(2) 0.13406(18) 0.0293(7) Uani 1 1 d . . . C12B C 0.5115(3) 0.2630(2) 0.20513(19) 0.0339(7) Uani 1 1 d . A . C13B C 0.5996(3) 0.1643(2) 0.35046(18) 0.0347(7) Uani 1 1 d . A . C14B C 0.6697(3) 0.1262(2) 0.3005(2) 0.0390(8) Uani 1 1 d . . . C15B C 0.7428(3) 0.0675(3) 0.3312(2) 0.0464(9) Uani 1 1 d . A . C16B C 0.7484(3) 0.0456(3) 0.4118(2) 0.0515(9) Uani 1 1 d . . . C17B C 0.6787(3) 0.0803(3) 0.4629(2) 0.0517(10) Uani 1 1 d . A . C18B C 0.6057(3) 0.1386(3) 0.43248(19) 0.0430(8) Uani 1 1 d . . . C19B C 0.3448(3) 0.1959(2) 0.33385(16) 0.0311(7) Uani 1 1 d D A . C20B C 0.2983(3) 0.0937(2) 0.34638(17) 0.0337(7) Uani 1 1 d D . . C21B C 0.1777(3) 0.0523(3) 0.35942(19) 0.0391(8) Uani 1 1 d D A . C22B C 0.1011(3) 0.1126(3) 0.36003(19) 0.0466(9) Uani 1 1 d D . . C23B C 0.1429(3) 0.2136(3) 0.3467(2) 0.0501(10) Uani 1 1 d D A . C24B C 0.2643(3) 0.2548(3) 0.33402(19) 0.0441(9) Uani 1 1 d D . . C25B C 0.6055(9) 0.3773(11) 0.3753(6) 0.0251(18) Uani 0.473(4) 1 d PD A 1 C26B C 0.6591(10) 0.4565(11) 0.3381(8) 0.031(2) Uani 0.473(4) 1 d PD A 1 C27B C 0.691(3) 0.5580(14) 0.3770(9) 0.051(3) Uani 0.473(4) 1 d PD A 1 C28B C 0.7388(8) 0.5704(8) 0.4581(7) 0.0398(19) Uani 0.473(4) 1 d PD A 1 C29B C 0.7277(7) 0.4857(5) 0.4994(4) 0.0457(12) Uani 0.473(4) 1 d PD A 1 H29B H 0.7663 0.4927 0.5560 0.069 Uiso 0.473(4) 1 calc PR A 1 C30B C 0.6603(6) 0.3902(5) 0.4586(4) 0.0386(11) Uani 0.473(4) 1 d PD A 1 H30B H 0.6512 0.3322 0.4882 0.058 Uiso 0.473(4) 1 calc PR A 1 C25X C 0.5640(7) 0.3834(10) 0.3689(6) 0.0251(18) Uani 0.53 1 d PD A 2 C26X C 0.6172(8) 0.4659(10) 0.3360(7) 0.031(2) Uani 0.53 1 d PD A 2 H26X H 0.5954 0.4664 0.2777 0.046 Uiso 0.527(4) 1 calc PR A 2 C27X C 0.705(3) 0.5543(13) 0.3830(8) 0.051(3) Uani 0.53 1 d PD A 2 H27X H 0.7754 0.5938 0.3623 0.076 Uiso 0.527(4) 1 calc PR A 2 C28X C 0.6826(7) 0.5778(7) 0.4584(6) 0.0398(19) Uani 0.53 1 d PD A 2 H28X H 0.7289 0.6409 0.4908 0.060 Uiso 0.527(4) 1 calc PR A 2 C29X C 0.5903(6) 0.5082(4) 0.4882(3) 0.0457(12) Uani 0.53 1 d PD A 2 H29X H 0.5668 0.5260 0.5392 0.069 Uiso 0.527(4) 1 calc PR A 2 C30X C 0.5319(6) 0.4127(4) 0.4443(3) 0.0386(11) Uani 0.53 1 d PD A 2 H30X H 0.4685 0.3657 0.4657 0.058 Uiso 0.527(4) 1 calc PR A 2 C31B C 0.2731(5) 0.4340(3) 0.1396(3) 0.0612(12) Uani 1 1 d . . . O1Z O 0.8896(13) 0.3722(11) 0.4457(8) 0.050 Uiso 0.159(4) 1 d P . . H1Z H 0.8168 0.3645 0.4211 0.075 Uiso 0.159(4) 1 calc PR . . C1Z C 0.924(2) 0.4500(16) 0.4961(13) 0.050 Uiso 0.159(4) 1 d P . . H2Z H 0.8588 0.4832 0.4932 0.075 Uiso 0.159(4) 1 calc PR . . H3Z H 0.9997 0.4971 0.4826 0.075 Uiso 0.159(4) 1 calc PR . . H4Z H 0.9427 0.4318 0.5524 0.075 Uiso 0.159(4) 1 calc PR . . H2A H 0.388(3) 1.068(2) -0.0126(18) 0.041(9) Uiso 1 1 d . . . H3A H 0.304(3) 1.113(3) -0.142(2) 0.072(12) Uiso 1 1 d . . . H4A H 0.096(3) 1.054(3) -0.194(2) 0.063(11) Uiso 1 1 d . . . H5A H -0.109(3) 0.939(2) -0.1917(19) 0.049(9) Uiso 1 1 d . . . H6A H -0.244(3) 0.816(2) -0.1238(18) 0.042(8) Uiso 1 1 d . . . H7A H -0.157(3) 0.761(2) 0.0006(16) 0.032(8) Uiso 1 1 d . . . H14A H 0.019(3) 0.535(2) 0.080(2) 0.052(10) Uiso 1 1 d . . . H15A H -0.071(3) 0.363(2) 0.050(2) 0.040(9) Uiso 1 1 d . . . H16A H -0.138(4) 0.259(3) 0.154(2) 0.080(12) Uiso 1 1 d . . . H17A H -0.124(3) 0.340(3) 0.288(2) 0.058(11) Uiso 1 1 d . . . H18A H -0.033(3) 0.516(3) 0.318(2) 0.058(11) Uiso 1 1 d . . . H21A H 0.455(3) 0.611(3) 0.367(2) 0.072(12) Uiso 1 1 d . . . H20A H 0.248(3) 0.574(2) 0.2996(18) 0.037(9) Uiso 1 1 d . . . H22A H 0.578(4) 0.782(3) 0.387(2) 0.081(13) Uiso 1 1 d . . . H23A H 0.501(3) 0.909(3) 0.338(2) 0.064(12) Uiso 1 1 d . . . H24A H 0.293(3) 0.871(3) 0.274(2) 0.059(10) Uiso 1 1 d . . . H26A H -0.128(2) 0.7739(18) 0.2211(16) 0.017(7) Uiso 1 1 d . . . H27A H -0.227(3) 0.838(2) 0.3120(19) 0.051(9) Uiso 1 1 d . . . H28A H -0.154(3) 0.854(2) 0.460(2) 0.056(10) Uiso 1 1 d . . . H29A H 0.021(3) 0.800(2) 0.506(2) 0.042(9) Uiso 1 1 d . . . H30A H 0.105(3) 0.726(2) 0.4110(17) 0.030(8) Uiso 1 1 d . . . H31A H 0.411(3) 0.965(3) 0.174(2) 0.065(12) Uiso 1 1 d . . . H31B H 0.409(3) 1.070(3) 0.1301(19) 0.057(10) Uiso 1 1 d . . . H31C H 0.458(3) 0.990(2) 0.0836(18) 0.043(9) Uiso 1 1 d . . . H2B H 0.249(3) 0.476(2) -0.0049(17) 0.039(8) Uiso 1 1 d . . . H3B H 0.268(3) 0.473(2) -0.1460(18) 0.039(8) Uiso 1 1 d . . . H4B H 0.400(3) 0.391(3) -0.202(2) 0.063(11) Uiso 1 1 d . . . H5B H 0.549(3) 0.304(2) -0.1783(19) 0.042(8) Uiso 1 1 d . . . H6B H 0.677(3) 0.231(2) -0.0881(16) 0.031(8) Uiso 1 1 d . . . H7B H 0.659(3) 0.222(2) 0.0555(19) 0.054(9) Uiso 1 1 d . . . H14B H 0.668(3) 0.148(2) 0.2416(19) 0.046(9) Uiso 1 1 d . . . H15B H 0.783(3) 0.040(3) 0.295(2) 0.064(11) Uiso 1 1 d . . . H16B H 0.802(3) 0.004(3) 0.434(2) 0.059(10) Uiso 1 1 d . . . H17B H 0.684(3) 0.065(2) 0.522(2) 0.058(10) Uiso 1 1 d . . . H18B H 0.550(3) 0.166(2) 0.4672(18) 0.044(8) Uiso 1 1 d . . . H20B H 0.357(3) 0.055(2) 0.3460(17) 0.042(9) Uiso 1 1 d . . . H21B H 0.148(3) -0.017(3) 0.3658(19) 0.048(10) Uiso 1 1 d . . . H22B H 0.016(3) 0.084(2) 0.3692(18) 0.046(9) Uiso 1 1 d . . . H23B H 0.098(3) 0.260(3) 0.348(2) 0.061(11) Uiso 1 1 d . . . H24B H 0.298(2) 0.325(2) 0.3281(15) 0.020(7) Uiso 1 1 d . . . H26B H 0.678(8) 0.430(6) 0.284(5) 0.25(4) Uiso 1 1 d . . . H27B H 0.694(5) 0.617(4) 0.344(3) 0.139(19) Uiso 1 1 d . . . H28B H 0.776(5) 0.633(4) 0.482(3) 0.14(2) Uiso 1 1 d . . . H31X H 0.298(3) 0.510(3) 0.133(2) 0.074(11) Uiso 1 1 d . . . H31Y H 0.289(3) 0.426(3) 0.203(2) 0.068(12) Uiso 1 1 d . . . H31Z H 0.183(5) 0.404(4) 0.102(3) 0.13(2) 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 0.0276(5) 0.0320(5) 0.0302(5) -0.0011(4) 0.0041(4) 0.0056(4) O1A 0.0240(12) 0.0340(12) 0.0637(15) -0.0035(11) 0.0067(11) -0.0007(10) C1A 0.0351(19) 0.0275(17) 0.050(2) -0.0009(15) 0.0192(16) 0.0078(16) C2A 0.038(2) 0.033(2) 0.070(3) -0.0084(19) 0.029(2) -0.0040(18) C3A 0.077(3) 0.034(2) 0.061(3) 0.0052(19) 0.045(3) 0.003(2) C4A 0.067(3) 0.0332(19) 0.047(2) 0.0053(17) 0.033(2) 0.008(2) C5A 0.052(2) 0.0302(18) 0.0278(18) 0.0011(14) 0.0106(16) 0.0139(17) C6A 0.039(2) 0.0342(18) 0.0299(18) -0.0019(14) 0.0015(15) 0.0125(17) C7A 0.0286(17) 0.0246(16) 0.0351(18) 0.0013(14) 0.0086(15) 0.0028(14) C8A 0.0315(17) 0.0240(15) 0.0260(16) -0.0012(12) 0.0107(13) 0.0055(14) C9A 0.0364(18) 0.0217(15) 0.0401(18) -0.0025(13) 0.0176(15) 0.0087(15) C10A 0.052(2) 0.0234(16) 0.0355(18) 0.0011(13) 0.0230(16) 0.0089(16) C11A 0.0228(16) 0.0288(16) 0.0346(18) -0.0107(14) 0.0072(14) 0.0003(14) C12A 0.0230(16) 0.0334(17) 0.0376(18) -0.0016(15) 0.0077(14) 0.0025(14) C13A 0.0276(17) 0.0333(17) 0.0440(19) 0.0015(15) -0.0015(14) 0.0099(15) C14A 0.0393(19) 0.037(2) 0.048(2) -0.0095(17) 0.0015(17) 0.0171(17) C15A 0.049(2) 0.048(2) 0.064(3) -0.017(2) -0.002(2) 0.019(2) C16A 0.047(2) 0.035(2) 0.079(3) -0.004(2) -0.010(2) 0.010(2) C17A 0.064(3) 0.040(2) 0.074(3) 0.015(2) -0.003(2) -0.003(2) C18A 0.063(3) 0.041(2) 0.047(2) 0.0014(19) -0.001(2) 0.003(2) C19A 0.0277(16) 0.0438(19) 0.0242(16) -0.0013(14) 0.0062(13) 0.0070(16) C20A 0.034(2) 0.061(3) 0.0324(19) 0.0160(17) 0.0064(15) 0.011(2) C21A 0.037(2) 0.095(3) 0.045(2) 0.033(2) 0.0084(18) 0.021(2) C22A 0.028(2) 0.111(4) 0.0267(19) 0.004(2) 0.0049(16) 0.010(3) C23A 0.030(2) 0.071(3) 0.047(2) -0.016(2) 0.0068(17) -0.002(2) C24A 0.0332(19) 0.048(2) 0.046(2) -0.0118(17) 0.0059(16) 0.0079(18) C25A 0.0251(16) 0.0243(16) 0.0361(18) 0.0005(13) 0.0089(13) -0.0015(14) C26A 0.0349(18) 0.0301(17) 0.0350(19) 0.0021(14) 0.0077(15) 0.0045(15) C27A 0.0388(19) 0.0393(19) 0.045(2) 0.0086(15) 0.0166(17) 0.0133(17) C28A 0.043(2) 0.0358(19) 0.049(2) 0.0012(16) 0.0225(18) 0.0078(17) C29A 0.042(2) 0.043(2) 0.033(2) 0.0009(15) 0.0131(16) 0.0027(17) C30A 0.0312(18) 0.0380(19) 0.0339(19) 0.0052(14) 0.0083(15) 0.0055(16) C31A 0.027(2) 0.048(3) 0.077(3) -0.012(2) 0.006(2) -0.0032(19) Si2 0.0417(5) 0.0280(5) 0.0286(5) 0.0008(4) 0.0131(4) 0.0013(4) O1B 0.0482(14) 0.0353(12) 0.0586(15) 0.0103(11) 0.0307(12) 0.0172(11) C1B 0.0285(17) 0.0235(16) 0.050(2) 0.0034(14) 0.0131(15) -0.0002(15) C2B 0.0266(18) 0.0290(18) 0.071(3) 0.0085(17) 0.0089(17) 0.0042(16) C3B 0.0317(19) 0.039(2) 0.064(3) 0.0154(19) -0.0109(18) -0.0005(17) C4B 0.0345(19) 0.042(2) 0.044(2) 0.0074(16) -0.0029(16) -0.0011(17) C5B 0.0386(19) 0.0376(18) 0.0256(18) 0.0026(14) 0.0073(15) 0.0030(16) C6B 0.0355(18) 0.0361(18) 0.0388(19) -0.0007(15) 0.0186(16) 0.0058(17) C7B 0.0289(17) 0.0289(16) 0.0327(17) 0.0041(14) 0.0071(14) 0.0029(15) C8B 0.0242(15) 0.0252(15) 0.0277(16) -0.0001(12) 0.0057(13) -0.0022(14) C9B 0.0202(15) 0.0227(15) 0.0343(17) 0.0012(13) 0.0021(13) -0.0045(13) C10B 0.0294(17) 0.0317(17) 0.0287(17) 0.0046(13) -0.0012(14) -0.0009(15) C11B 0.0278(16) 0.0220(15) 0.0347(19) -0.0018(13) 0.0088(14) 0.0017(14) C12B 0.0341(18) 0.0291(17) 0.0329(18) -0.0001(14) 0.0089(14) 0.0003(15) C13B 0.0267(16) 0.0361(18) 0.0319(18) -0.0052(14) 0.0071(14) -0.0039(15) C14B 0.0324(18) 0.0383(19) 0.038(2) -0.0049(15) 0.0090(15) -0.0011(16) C15B 0.0296(18) 0.052(2) 0.052(2) -0.0093(18) 0.0101(17) 0.0060(18) C16B 0.035(2) 0.065(3) 0.051(2) -0.0025(19) -0.0026(17) 0.016(2) C17B 0.038(2) 0.077(3) 0.035(2) 0.0043(19) -0.0021(17) 0.013(2) C18B 0.0290(18) 0.064(2) 0.0330(19) -0.0003(16) 0.0038(15) 0.0110(18) C19B 0.0385(18) 0.0316(17) 0.0249(16) 0.0027(13) 0.0107(13) 0.0109(15) C20B 0.0318(18) 0.0391(19) 0.0297(17) 0.0071(14) 0.0054(14) 0.0095(17) C21B 0.0320(18) 0.044(2) 0.0351(19) 0.0080(16) 0.0057(15) 0.0013(18) C22B 0.039(2) 0.071(3) 0.0295(18) 0.0016(17) 0.0120(16) 0.015(2) C23B 0.056(2) 0.073(3) 0.039(2) 0.0042(18) 0.0152(17) 0.044(2) C24B 0.064(2) 0.039(2) 0.040(2) 0.0043(16) 0.0212(17) 0.025(2) C25B 0.014(5) 0.036(2) 0.027(2) 0.0068(18) 0.006(3) 0.009(4) C26B 0.032(6) 0.031(3) 0.031(2) 0.0016(18) 0.010(4) 0.011(4) C27B 0.071(6) 0.033(2) 0.043(3) 0.008(2) 0.021(3) 0.001(3) C28B 0.045(6) 0.031(2) 0.037(2) 0.0011(19) 0.010(4) 0.000(4) C29B 0.059(3) 0.045(3) 0.027(2) 0.001(2) 0.004(2) 0.008(3) C30B 0.048(3) 0.033(3) 0.032(2) 0.006(2) 0.009(2) 0.006(2) C25X 0.014(5) 0.036(2) 0.027(2) 0.0068(18) 0.006(3) 0.009(4) C26X 0.032(6) 0.031(3) 0.031(2) 0.0016(18) 0.010(4) 0.011(4) C27X 0.071(6) 0.033(2) 0.043(3) 0.008(2) 0.021(3) 0.001(3) C28X 0.045(6) 0.031(2) 0.037(2) 0.0011(19) 0.010(4) 0.000(4) C29X 0.059(3) 0.045(3) 0.027(2) 0.001(2) 0.004(2) 0.008(3) C30X 0.048(3) 0.033(3) 0.032(2) 0.006(2) 0.009(2) 0.006(2) C31B 0.071(3) 0.046(2) 0.088(3) 0.016(2) 0.052(3) 0.032(2) _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 C12A 1.813(3) . ? Si1 C19A 1.863(3) . ? Si1 C25A 1.866(3) . ? Si1 C13A 1.866(3) . ? O1A C1A 1.368(4) . ? O1A C31A 1.429(4) . ? C1A C2A 1.375(4) . ? C1A C9A 1.417(4) . ? C2A C3A 1.395(5) . ? C3A C4A 1.351(5) . ? C4A C10A 1.419(4) . ? C5A C6A 1.359(4) . ? C5A C10A 1.406(4) . ? C6A C7A 1.395(4) . ? C7A C8A 1.377(4) . ? C8A C9A 1.435(4) . ? C8A C11A 1.440(4) . ? C9A C10A 1.429(4) . ? C11A C12A 1.216(4) . ? C13A C14A 1.392(4) . ? C13A C18A 1.398(4) . ? C14A C15A 1.388(5) . ? C15A C16A 1.358(5) . ? C16A C17A 1.370(5) . ? C17A C18A 1.385(5) . ? C19A C20A 1.390(4) . ? C19A C24A 1.400(4) . ? C20A C21A 1.387(5) . ? C21A C22A 1.382(6) . ? C22A C23A 1.373(6) . ? C23A C24A 1.383(5) . ? C25A C30A 1.391(4) . ? C25A C26A 1.393(4) . ? C26A C27A 1.384(4) . ? C27A C28A 1.376(4) . ? C28A C29A 1.383(5) . ? C29A C30A 1.385(4) . ? Si2 C12B 1.818(3) . ? Si2 C13B 1.859(3) . ? Si2 C25X 1.865(12) . ? Si2 C19B 1.879(3) . ? Si2 C25B 1.893(13) . ? O1B C1B 1.354(3) . ? O1B C31B 1.432(4) . ? C1B C2B 1.374(4) . ? C1B C9B 1.424(4) . ? C2B C3B 1.400(5) . ? C3B C4B 1.360(5) . ? C4B C10B 1.412(4) . ? C5B C6B 1.358(4) . ? C5B C10B 1.407(4) . ? C6B C7B 1.411(4) . ? C7B C8B 1.380(4) . ? C8B C9B 1.446(4) . ? C8B C11B 1.447(4) . ? C9B C10B 1.416(4) . ? C11B C12B 1.207(4) . ? C13B C14B 1.400(4) . ? C13B C18B 1.407(4) . ? C14B C15B 1.386(5) . ? C15B C16B 1.368(5) . ? C16B C17B 1.385(5) . ? C17B C18B 1.379(5) . ? C19B C24B 1.389(4) . ? C19B C20B 1.395(4) . ? C20B C21B 1.385(4) . ? C21B C22B 1.367(5) . ? C22B C23B 1.377(5) . ? C23B C24B 1.391(5) . ? C25B C26B 1.323(10) . ? C25B C30B 1.387(10) . ? C26B C27B 1.416(14) . ? C27B C28B 1.335(16) . ? C28B C29B 1.371(10) . ? C29B C30B 1.381(8) . ? C25X C26X 1.316(9) . ? C25X C30X 1.402(9) . ? C26X C27X 1.422(13) . ? C27X C28X 1.335(15) . ? C28X C29X 1.379(9) . ? C29X C30X 1.382(7) . ? O1Z C1Z 1.23(2) . ? C1Z C1Z 1.85(4) 2_766 ? 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 C12A Si1 C19A 109.91(13) . . ? C12A Si1 C25A 107.29(13) . . ? C19A Si1 C25A 107.75(13) . . ? C12A Si1 C13A 110.21(14) . . ? C19A Si1 C13A 110.60(13) . . ? C25A Si1 C13A 110.99(13) . . ? C1A O1A C31A 118.3(3) . . ? O1A C1A C2A 123.9(3) . . ? O1A C1A C9A 115.4(3) . . ? C2A C1A C9A 120.6(3) . . ? C1A C2A C3A 120.9(4) . . ? C4A C3A C2A 120.4(4) . . ? C3A C4A C10A 121.0(4) . . ? C6A C5A C10A 121.3(3) . . ? C5A C6A C7A 119.3(3) . . ? C8A C7A C6A 122.4(3) . . ? C7A C8A C9A 119.4(3) . . ? C7A C8A C11A 115.5(2) . . ? C9A C8A C11A 125.1(3) . . ? C1A C9A C10A 117.9(3) . . ? C1A C9A C8A 124.6(3) . . ? C10A C9A C8A 117.5(3) . . ? C5A C10A C4A 120.7(3) . . ? C5A C10A C9A 120.0(3) . . ? C4A C10A C9A 119.2(3) . . ? C12A C11A C8A 169.8(3) . . ? C11A C12A Si1 174.1(3) . . ? C14A C13A C18A 116.4(3) . . ? C14A C13A Si1 122.6(3) . . ? C18A C13A Si1 121.0(2) . . ? C15A C14A C13A 121.5(4) . . ? C16A C15A C14A 120.7(4) . . ? C15A C16A C17A 119.3(4) . . ? C16A C17A C18A 120.7(4) . . ? C17A C18A C13A 121.3(4) . . ? C20A C19A C24A 117.1(3) . . ? C20A C19A Si1 123.6(3) . . ? C24A C19A Si1 119.2(2) . . ? C21A C20A C19A 121.8(4) . . ? C22A C21A C20A 119.1(4) . . ? C23A C22A C21A 121.0(4) . . ? C22A C23A C24A 119.1(4) . . ? C23A C24A C19A 121.9(4) . . ? C30A C25A C26A 116.8(3) . . ? C30A C25A Si1 121.7(2) . . ? C26A C25A Si1 121.4(2) . . ? C27A C26A C25A 122.0(3) . . ? C28A C27A C26A 119.8(3) . . ? C27A C28A C29A 119.7(3) . . ? C28A C29A C30A 119.8(3) . . ? C29A C30A C25A 121.8(3) . . ? C12B Si2 C13B 109.53(13) . . ? C12B Si2 C25X 105.6(3) . . ? C13B Si2 C25X 115.9(3) . . ? C12B Si2 C19B 111.56(13) . . ? C13B Si2 C19B 108.64(13) . . ? C25X Si2 C19B 105.6(3) . . ? C12B Si2 C25B 107.0(4) . . ? C13B Si2 C25B 101.7(3) . . ? C25X Si2 C25B 15.3(4) . . ? C19B Si2 C25B 117.8(3) . . ? C1B O1B C31B 118.0(3) . . ? O1B C1B C2B 124.3(3) . . ? O1B C1B C9B 115.2(3) . . ? C2B C1B C9B 120.5(3) . . ? C1B C2B C3B 120.0(3) . . ? C4B C3B C2B 121.3(3) . . ? C3B C4B C10B 120.1(3) . . ? C6B C5B C10B 121.6(3) . . ? C5B C6B C7B 119.6(3) . . ? C8B C7B C6B 120.9(3) . . ? C7B C8B C9B 120.1(2) . . ? C7B C8B C11B 116.1(2) . . ? C9B C8B C11B 123.8(2) . . ? C10B C9B C1B 118.4(3) . . ? C10B C9B C8B 117.6(2) . . ? C1B C9B C8B 124.0(3) . . ? C5B C10B C4B 120.2(3) . . ? C5B C10B C9B 120.1(3) . . ? C4B C10B C9B 119.7(3) . . ? C12B C11B C8B 173.0(3) . . ? C11B C12B Si2 173.1(3) . . ? C14B C13B C18B 116.8(3) . . ? C14B C13B Si2 123.1(2) . . ? C18B C13B Si2 120.1(2) . . ? C15B C14B C13B 121.2(3) . . ? C16B C15B C14B 120.5(3) . . ? C15B C16B C17B 120.1(3) . . ? C18B C17B C16B 119.5(3) . . ? C17B C18B C13B 121.9(3) . . ? C24B C19B C20B 117.1(3) . . ? C24B C19B Si2 121.6(2) . . ? C20B C19B Si2 121.3(2) . . ? C21B C20B C19B 121.9(3) . . ? C22B C21B C20B 119.6(3) . . ? C21B C22B C23B 120.4(3) . . ? C22B C23B C24B 119.7(3) . . ? C19B C24B C23B 121.4(3) . . ? C26B C25B C30B 110.5(10) . . ? C26B C25B Si2 122.2(9) . . ? C30B C25B Si2 124.5(9) . . ? C25B C26B C27B 121.8(12) . . ? C28B C27B C26B 114.5(18) . . ? C27B C28B C29B 118.9(11) . . ? C28B C29B C30B 120.0(7) . . ? C29B C30B C25B 121.3(8) . . ? C26X C25X C30X 109.0(9) . . ? C26X C25X Si2 125.7(8) . . ? C30X C25X Si2 124.0(8) . . ? C25X C26X C27X 123.6(11) . . ? C28X C27X C26X 114.9(17) . . ? C27X C28X C29X 118.4(10) . . ? C28X C29X C30X 120.3(6) . . ? C29X C30X C25X 121.6(7) . . ? O1Z C1Z C1Z 124(2) . 2_766 ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.350 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.065 #===END data_ket-16 _database_code_CSD 178493 _audit_creation_method SHELXL _chemical_name_systematic ; 4-(8-methoxynaphth-1-yl)but-3-yn-2-one ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H12 O2' _chemical_formula_weight 224.25 _chemical_melting_point 329-330 _chemical_compound_source ? 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 8.1848(2) _cell_length_b 13.7072(4) _cell_length_c 20.2962(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2277.04(11) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1899 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 25.01 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method ? _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.930 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R. H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKa _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Phi and Omega scans to fill Ewald sphere' _diffrn_measurement_method 'Enraf Nonius KappaCCD area detector' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18112 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2000 _reflns_number_observed 1622 _reflns_observed_criterion >2sigma(I) _computing_data_collection ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_cell_refinement ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_data_reduction ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEP3 (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXL-93(Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 101 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w = 1/[s^2^(Fo^2^)+( 0.0757P)^2^+0.1064P] 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 ? _refine_ls_number_reflns 1899 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_obs 0.0398 _refine_ls_wR_factor_all 0.1146 _refine_ls_wR_factor_obs 0.1033 _refine_ls_goodness_of_fit_all 1.070 _refine_ls_goodness_of_fit_obs 1.104 _refine_ls_restrained_S_all 1.090 _refine_ls_restrained_S_obs 1.104 _refine_ls_shift/esd_max 0.064 _refine_ls_shift/esd_mean 0.008 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.04019(10) 0.49504(6) 0.19343(4) 0.0300(3) Uani 1 d . . O2 O 0.33223(14) 0.75316(8) 0.04207(5) 0.0521(3) Uani 1 d . . C1 C 0.02811(14) 0.49182(8) 0.26002(6) 0.0247(3) Uani 1 d . . C2 C -0.0607(2) 0.42279(9) 0.29340(7) 0.0298(3) Uani 1 d . . C3 C -0.0656(2) 0.42312(10) 0.36264(7) 0.0342(4) Uani 1 d . . C4 C 0.0189(2) 0.49113(9) 0.39748(7) 0.0324(3) Uani 1 d . . C5 C 0.19795(15) 0.63468(10) 0.40149(7) 0.0306(3) Uani 1 d . . C6 C 0.2875(2) 0.70516(10) 0.37098(7) 0.0311(3) Uani 1 d . . C7 C 0.29194(15) 0.70912(10) 0.30219(6) 0.0277(3) Uani 1 d . . C8 C 0.20774(14) 0.64269(9) 0.26372(6) 0.0233(3) Uani 1 d . . C9 C 0.11083(14) 0.56408(9) 0.36488(6) 0.0263(3) Uani 1 d . . C10 C 0.11536(14) 0.56650(8) 0.29476(6) 0.0229(3) Uani 1 d . . C11 C 0.21913(14) 0.65569(9) 0.19392(6) 0.0248(3) Uani 1 d . . C12 C 0.2379(2) 0.67560(9) 0.13655(6) 0.0285(3) Uani 1 d . . C18 C -0.0262(2) 0.41532(10) 0.15680(7) 0.0359(4) Uani 1 d . . C20 C 0.2525(2) 0.68734(10) 0.06602(6) 0.0322(4) Uani 1 d . . C21 C 0.1615(2) 0.61531(12) 0.02504(8) 0.0428(4) Uani 1 d . . H2 H -0.1218(19) 0.3732(11) 0.2692(7) 0.039(4) Uiso 1 d . . H3 H -0.1314(19) 0.3764(11) 0.3843(8) 0.044(4) Uiso 1 d . . H4 H 0.0156(19) 0.4925(11) 0.4453(9) 0.049(4) Uiso 1 d . . H5 H 0.1917(19) 0.6319(12) 0.4508(8) 0.050(5) Uiso 1 d . . H6 H 0.3470(16) 0.7532(10) 0.3963(7) 0.035(4) Uiso 1 d . . H7 H 0.3570(18) 0.7575(11) 0.2808(7) 0.036(4) Uiso 1 d . . H18A H 0.0194(18) 0.3513(11) 0.1721(7) 0.037(4) Uiso 1 d . . H18B H 0.0023(19) 0.4309(10) 0.1085(9) 0.049(4) Uiso 1 d . . H18C H -0.1488(20) 0.4137(10) 0.1622(7) 0.038(4) Uiso 1 d . . H21A H 0.0466(32) 0.6263(17) 0.0272(11) 0.104(7) Uiso 1 d . . H21B H 0.1977(27) 0.6193(16) -0.0175(12) 0.087(7) Uiso 1 d . . H21C H 0.1768(24) 0.5457(14) 0.0417(9) 0.079(6) Uiso 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 O1 0.0369(5) 0.0315(5) 0.0215(5) -0.0045(3) -0.0027(4) -0.0044(4) O2 0.0627(7) 0.0606(7) 0.0329(7) 0.0134(5) 0.0027(5) -0.0148(6) C1 0.0260(7) 0.0255(7) 0.0226(7) -0.0011(5) -0.0015(5) 0.0060(5) C2 0.0289(7) 0.0252(7) 0.0354(8) 0.0000(6) -0.0011(6) 0.0010(5) C3 0.0357(7) 0.0310(8) 0.0358(8) 0.0082(6) 0.0069(6) 0.0013(6) C4 0.0347(7) 0.0377(8) 0.0248(8) 0.0052(6) 0.0033(6) 0.0064(6) C5 0.0324(7) 0.0377(8) 0.0217(7) -0.0040(6) -0.0026(5) 0.0079(6) C6 0.0314(7) 0.0335(7) 0.0283(8) -0.0089(6) -0.0057(6) 0.0027(6) C7 0.0270(7) 0.0280(7) 0.0281(8) -0.0008(6) -0.0017(5) 0.0010(5) C8 0.0231(6) 0.0255(7) 0.0215(7) -0.0010(5) -0.0010(5) 0.0056(5) C9 0.0259(7) 0.0310(7) 0.0221(7) 0.0000(5) 0.0014(5) 0.0089(5) C10 0.0222(6) 0.0241(6) 0.0224(7) -0.0009(5) -0.0008(5) 0.0070(5) C11 0.0240(6) 0.0244(7) 0.0262(7) -0.0006(5) -0.0001(5) 0.0025(5) C12 0.0293(7) 0.0288(7) 0.0273(8) 0.0001(5) -0.0006(5) 0.0013(5) C18 0.0429(9) 0.0318(8) 0.0330(8) -0.0077(6) -0.0077(7) -0.0023(6) C20 0.0323(7) 0.0399(8) 0.0243(7) 0.0045(6) 0.0004(6) 0.0070(6) C21 0.0454(9) 0.0559(10) 0.0271(8) -0.0060(7) -0.0029(7) 0.0021(8) _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 C1 1.356(2) . ? O1 C18 1.429(2) . ? O2 C20 1.215(2) . ? C1 C2 1.372(2) . ? C1 C10 1.434(2) . ? C2 C3 1.406(2) . ? C3 C4 1.359(2) . ? C4 C9 1.416(2) . ? C5 C6 1.362(2) . ? C5 C9 1.413(2) . ? C6 C7 1.398(2) . ? C7 C8 1.383(2) . ? C8 C11 1.431(2) . ? C8 C10 1.435(2) . ? C9 C10 1.424(2) . ? C11 C12 1.206(2) . ? C12 C20 1.445(2) . ? C20 C21 1.490(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 C1 O1 C18 117.77(10) . . ? O1 C1 C2 123.60(11) . . ? O1 C1 C10 115.51(10) . . ? C2 C1 C10 120.89(12) . . ? C1 C2 C3 120.45(12) . . ? C4 C3 C2 120.50(13) . . ? C3 C4 C9 120.78(13) . . ? C6 C5 C9 121.22(12) . . ? C5 C6 C7 119.72(12) . . ? C8 C7 C6 121.69(12) . . ? C7 C8 C11 116.38(11) . . ? C7 C8 C10 119.59(11) . . ? C11 C8 C10 124.03(11) . . ? C5 C9 C4 120.40(12) . . ? C5 C9 C10 119.76(11) . . ? C4 C9 C10 119.84(11) . . ? C9 C10 C1 117.51(11) . . ? C9 C10 C8 118.00(11) . . ? C1 C10 C8 124.49(11) . . ? C12 C11 C8 173.02(13) . . ? C11 C12 C20 172.78(14) . . ? O2 C20 C12 121.55(13) . . ? O2 C20 C21 122.49(13) . . ? C12 C20 C21 115.95(12) . . ? _refine_diff_density_max 0.188 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.041 #===END data_ester-17 _database_code_CSD 178494 _audit_creation_method SHELXL _chemical_name_systematic ; 3-(8-methoxynaphth-1-yl)propynoate ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H12 O3' _chemical_formula_weight 240.25 _chemical_melting_point 350 _chemical_compound_source ? 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.5576(5) _cell_length_b 7.5977(3) _cell_length_c 10.9690(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.847(3) _cell_angle_gamma 90.00 _cell_volume 592.43(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2005 _cell_measurement_theta_min 1.97 _cell_measurement_theta_max 25.05 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method ? _exptl_crystal_F_000 252 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.944 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R. H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKa _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Phi and Omega scans to fill Ewald sphere' _diffrn_measurement_method 'Enraf Nonius KappaCCD area detector' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6681 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0461 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2046 _reflns_number_observed 1822 _reflns_observed_criterion >2sigma(I) _computing_data_collection ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_cell_refinement ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_data_reduction ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEP3 (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 41 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[s^2^(Fo^2^)+( 0.0747P)^2^+0.0641P] 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 ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.45(141) _refine_ls_number_reflns 2005 _refine_ls_number_parameters 211 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_obs 0.0463 _refine_ls_wR_factor_all 0.1271 _refine_ls_wR_factor_obs 0.1221 _refine_ls_goodness_of_fit_all 1.155 _refine_ls_goodness_of_fit_obs 1.186 _refine_ls_restrained_S_all 1.157 _refine_ls_restrained_S_obs 1.186 _refine_ls_shift/esd_max -0.030 _refine_ls_shift/esd_mean 0.003 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.2739(3) 0.1626(2) 0.0645(2) 0.0314(5) Uani 1 d . . O2 O 0.6270(3) -0.1048(3) 0.3576(2) 0.0477(6) Uani 1 d . . O3 O 0.5419(3) -0.3877(3) 0.3205(2) 0.0339(5) Uani 1 d . . C1 C 0.1585(3) 0.1795(3) -0.0604(2) 0.0247(5) Uani 1 d . . C2 C 0.0498(4) 0.3258(4) -0.1091(3) 0.0307(6) Uani 1 d . . C3 C -0.0650(4) 0.3315(4) -0.2401(3) 0.0338(6) Uani 1 d . . C4 C -0.0716(4) 0.1934(4) -0.3209(3) 0.0310(6) Uani 1 d . . C5 C 0.0277(4) -0.1055(3) -0.3561(2) 0.0309(6) Uani 1 d . . C6 C 0.1295(4) -0.2550(4) -0.3108(2) 0.0326(6) Uani 1 d . . C7 C 0.2443(4) -0.2674(3) -0.1810(2) 0.0289(6) Uani 1 d . . C8 C 0.2573(3) -0.1300(3) -0.0956(2) 0.0247(6) Uani 1 d . . C9 C 0.0370(3) 0.0397(3) -0.2730(2) 0.0266(6) Uani 1 d . . C10 C 0.1538(3) 0.0303(3) -0.1408(2) 0.0230(5) Uani 1 d . . C11 C 0.3714(4) -0.1599(3) 0.0369(3) 0.0254(5) Uani 1 d . . C12 C 0.4638(4) -0.1996(3) 0.1460(3) 0.0282(6) Uani 1 d . . C13 C 0.5536(4) -0.2218(3) 0.2837(2) 0.0277(6) Uani 1 d . . C14 C 0.6180(5) -0.4208(4) 0.4581(3) 0.0411(7) Uani 1 d . . C18 C 0.2880(5) 0.3069(4) 0.1505(3) 0.0399(7) Uani 1 d . . H2 H 0.0578(58) 0.4211(62) -0.0500(37) 0.078(12) Uiso 1 d . . H3 H -0.1449(41) 0.4362(44) -0.2694(27) 0.037(7) Uiso 1 d . . H4 H -0.1562(37) 0.1974(41) -0.4165(27) 0.026(6) Uiso 1 d . . H5 H -0.0640(41) -0.1006(41) -0.4527(29) 0.039(8) Uiso 1 d . . H6 H 0.1302(39) -0.3589(44) -0.3649(27) 0.034(7) Uiso 1 d . . H7 H 0.3155(38) -0.3775(43) -0.1477(25) 0.028(7) Uiso 1 d . . H14A H 0.5992(70) -0.5654(85) 0.4686(45) 0.114(18) Uiso 1 d . . H14B H 0.7461(52) -0.4105(47) 0.4911(30) 0.048(9) Uiso 1 d . . H14C H 0.5536(50) -0.3479(52) 0.5024(35) 0.063(11) Uiso 1 d . . H18A H 0.3850(54) 0.2725(46) 0.2348(37) 0.053(10) Uiso 1 d . . H18B H 0.1730(57) 0.3274(51) 0.1667(33) 0.060(10) Uiso 1 d . . H18C H 0.3404(42) 0.4093(48) 0.1179(29) 0.044(9) Uiso 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 O1 0.0356(10) 0.0296(11) 0.0248(9) -0.0081(7) 0.0048(8) 0.0025(8) O2 0.0676(14) 0.0335(11) 0.0297(11) -0.0024(9) 0.0004(10) -0.0070(10) O3 0.0390(11) 0.0319(10) 0.0252(10) 0.0043(8) 0.0035(8) -0.0008(8) C1 0.0229(12) 0.0274(13) 0.0241(13) -0.0022(10) 0.0082(10) -0.0046(10) C2 0.0331(14) 0.0273(14) 0.035(2) -0.0001(11) 0.0157(12) 0.0007(12) C3 0.0324(14) 0.0299(15) 0.040(2) 0.0064(12) 0.0135(12) 0.0068(12) C4 0.0294(14) 0.0357(14) 0.0264(14) 0.0104(12) 0.0075(11) 0.0020(12) C5 0.0350(15) 0.0349(15) 0.0203(13) 0.0019(11) 0.0062(11) -0.0075(12) C6 0.0401(15) 0.0336(15) 0.0224(13) -0.0045(11) 0.0086(12) -0.0036(12) C7 0.0354(14) 0.0257(15) 0.0252(14) -0.0001(10) 0.0098(11) 0.0007(11) C8 0.0224(12) 0.0257(14) 0.0251(13) 0.0004(10) 0.0069(10) -0.0028(10) C9 0.0242(12) 0.0321(14) 0.0237(14) 0.0038(10) 0.0083(11) -0.0033(10) C10 0.0219(11) 0.0270(13) 0.0212(13) 0.0010(9) 0.0090(10) -0.0028(10) C11 0.0248(12) 0.0247(13) 0.0276(14) 0.0004(10) 0.0102(11) -0.0005(10) C12 0.0290(13) 0.0252(14) 0.031(2) 0.0005(10) 0.0105(12) 0.0014(10) C13 0.0276(12) 0.0269(14) 0.0265(13) 0.0003(11) 0.0065(11) 0.0022(11) C14 0.047(2) 0.048(2) 0.024(2) 0.0073(13) 0.0062(14) 0.0058(15) C18 0.041(2) 0.038(2) 0.036(2) -0.0161(13) 0.0075(14) 0.0053(14) _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 C1 1.357(3) . ? O1 C18 1.426(3) . ? O2 C13 1.204(3) . ? O3 C13 1.336(3) . ? O3 C14 1.443(3) . ? C1 C2 1.378(4) . ? C1 C10 1.429(3) . ? C2 C3 1.405(4) . ? C3 C4 1.364(4) . ? C4 C9 1.421(4) . ? C5 C6 1.367(4) . ? C5 C9 1.418(4) . ? C6 C7 1.397(4) . ? C7 C8 1.384(3) . ? C8 C11 1.434(3) . ? C8 C10 1.441(3) . ? C9 C10 1.421(3) . ? C11 C12 1.202(4) . ? C12 C13 1.440(4) . ? 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 O1 C18 118.2(2) . . ? C13 O3 C14 115.9(2) . . ? O1 C1 C2 124.2(2) . . ? O1 C1 C10 114.9(2) . . ? C2 C1 C10 121.0(2) . . ? C1 C2 C3 120.1(2) . . ? C4 C3 C2 121.0(2) . . ? C3 C4 C9 120.1(2) . . ? C6 C5 C9 120.9(2) . . ? C5 C6 C7 120.3(2) . . ? C8 C7 C6 121.1(2) . . ? C7 C8 C11 116.5(2) . . ? C7 C8 C10 120.0(2) . . ? C11 C8 C10 123.5(2) . . ? C5 C9 C10 119.7(2) . . ? C5 C9 C4 120.3(2) . . ? C10 C9 C4 120.0(2) . . ? C9 C10 C1 117.8(2) . . ? C9 C10 C8 118.1(2) . . ? C1 C10 C8 124.1(2) . . ? C12 C11 C8 174.6(3) . . ? C11 C12 C13 169.0(2) . . ? O2 C13 O3 123.8(2) . . ? O2 C13 C12 124.4(2) . . ? O3 C13 C12 111.8(2) . . ? _refine_diff_density_max 0.212 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.066 #===END data_amidech-18 _database_code_CSD 178495 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common '3-(8-methoxnaphth-1-yl)N-phenyl-prop-2-ynamide' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H15 N O2' _chemical_formula_weight 301.33 _chemical_melting_point 417-418 _chemical_compound_source ? 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.061(9) _cell_length_b 5.001(9) _cell_length_c 44.011(9) _cell_angle_alpha 90.00 _cell_angle_beta 91.99(4) _cell_angle_gamma 90.00 _cell_volume 3092.9(59) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 24 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method ? _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type 'psi-scans' _exptl_absorpt_correction_T_min 0.666 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKa _diffrn_radiation_source ? _diffrn_radiation_monochromator ? _diffrn_measurement_device 'Rigaku AFC7R diffractometer' _diffrn_measurement_method 'omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5061 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0721 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -50 _diffrn_reflns_limit_l_max 50 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 23.98 _reflns_number_total 4838 _reflns_number_observed 2970 _reflns_observed_criterion >2sigm'a(I) _computing_data_collection 'Rigaku AFC7R control software' _computing_cell_refinement 'Rigaku AFC7R control software' _computing_data_reduction 'teXsan' _computing_structure_solution 'teXsan' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEP3 (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; The (N)-H atoms were located in a difference map and refined, other H atoms were placed geometrically and refined with the riding model. Refinement on F^2^ for ALL reflections except for 580 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[s^2^(Fo^2^)+( 0.0508P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'located and geometrically fixed' _refine_ls_hydrogen_treatment 'mixed' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4258 _refine_ls_number_parameters 461 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.1067 _refine_ls_R_factor_obs 0.0541 _refine_ls_wR_factor_all 0.1404 _refine_ls_wR_factor_obs 0.1144 _refine_ls_goodness_of_fit_all 1.031 _refine_ls_goodness_of_fit_obs 1.129 _refine_ls_restrained_S_all 1.058 _refine_ls_restrained_S_obs 1.135 _refine_ls_shift/esd_max -0.094 _refine_ls_shift/esd_mean 0.006 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N -0.7512(2) 0.5313(5) 1.01767(6) 0.0352(7) Uani 1 d . . H1 H -0.7346(24) 0.3627(74) 1.0232(8) 0.063(11) Uiso 1 d . . O1 O -0.4544(2) 0.9954(5) 1.05750(5) 0.0498(6) Uani 1 d . . O2 O -0.7255(2) 0.9733(4) 1.02579(5) 0.0442(6) Uani 1 d . . C1 C -0.3914(2) 0.9432(7) 1.08107(7) 0.0425(9) Uani 1 d . . C2 C -0.3057(2) 1.0744(7) 1.08496(7) 0.0491(9) Uani 1 d . . H2 H -0.2884(2) 1.2062(7) 1.07132(7) 0.059 Uiso 1 calc R . C3 C -0.2448(2) 1.0069(9) 1.10977(8) 0.0577(11) Uani 1 d . . H3 H -0.1871(2) 1.0962(9) 1.11245(8) 0.069 Uiso 1 calc R . C4 C -0.2682(2) 0.8152(8) 1.12984(8) 0.0537(10) Uani 1 d . . H4 H -0.2264(2) 0.7745(8) 1.14601(8) 0.064 Uiso 1 calc R . C5 C -0.3800(3) 0.4712(8) 1.14689(7) 0.0502(10) Uani 1 d . . H5 H -0.3383(3) 0.4300(8) 1.16308(7) 0.060 Uiso 1 calc R . C6 C -0.4625(3) 0.3332(8) 1.14352(7) 0.0506(10) Uani 1 d . . H6 H -0.4770(3) 0.1991(8) 1.15725(7) 0.061 Uiso 1 calc R . C7 C -0.5260(2) 0.3933(7) 1.11925(7) 0.0443(9) Uani 1 d . . H7 H -0.5820(2) 0.2954(7) 1.11683(7) 0.053 Uiso 1 calc R . C8 C -0.5074(2) 0.5938(7) 1.09889(7) 0.0381(8) Uani 1 d . . C9 C -0.3556(2) 0.6758(7) 1.12652(7) 0.0450(9) Uani 1 d . . C10 C -0.4198(2) 0.7399(7) 1.10162(7) 0.0385(8) Uani 1 d . . C11 C -0.5789(2) 0.6432(6) 1.07523(7) 0.0371(8) Uani 1 d . . C12 C -0.6416(2) 0.6684(6) 1.05653(7) 0.0341(7) Uani 1 d . . C13 C -0.7097(2) 0.7394(6) 1.03226(6) 0.0306(7) Uani 1 d . . C18 C -0.4300(2) 1.1906(7) 1.03563(7) 0.0537(10) Uani 1 d . . H18A H -0.4806(7) 1.2060(33) 1.0205(3) 0.081 Uiso 1 calc R . H18B H -0.3726(9) 1.1376(24) 1.0261(4) 0.081 Uiso 1 calc R . H18C H -0.4203(16) 1.3600(12) 1.04552(11) 0.081 Uiso 1 calc R . C20 C -0.8183(2) 0.5513(5) 0.99266(6) 0.0317(7) Uani 1 d DU . C21A C -0.7983(7) 0.4263(12) 0.96585(15) 0.037(2) Uani 0.50 d PDU 1 H21A H -0.7406(7) 0.3381(12) 0.96378(15) 0.044 Uiso 0.50 calc PR 1 C21B C -0.8269(5) 0.3412(14) 0.97259(15) 0.035(2) Uani 0.50 d PDU 2 H21B H -0.7888(5) 0.1909(14) 0.97561(15) 0.042 Uiso 0.50 calc PR 2 C22A C -0.8647(5) 0.4331(14) 0.9420(2) 0.047(3) Uani 0.50 d PDU 1 H22A H -0.8520(5) 0.3446(14) 0.9240(2) 0.056 Uiso 0.50 calc PR 1 C22B C -0.8909(5) 0.3483(16) 0.9480(2) 0.047(2) Uani 0.50 d PDU 2 H22B H -0.8946(5) 0.2070(16) 0.9343(2) 0.056 Uiso 0.50 calc PR 2 C23 C -0.9487(2) 0.5673(6) 0.94432(7) 0.0484(9) Uani 1 d DU . H23 H -0.9923 0.5731 0.9280 0.058 Uiso 1 d . . C24A C -0.9691(5) 0.6824(14) 0.97235(14) 0.045(2) Uani 0.50 d PDU 1 H24A H -1.0277(5) 0.7644(14) 0.97468(14) 0.054 Uiso 0.50 calc PR 1 C24B C -0.9394(5) 0.7865(13) 0.9629(2) 0.045(2) Uani 0.50 d PDU 2 H24B H -0.9755(5) 0.9396(13) 0.9591(2) 0.054 Uiso 0.50 calc PR 2 C25A C -0.9038(4) 0.6770(15) 0.9968(2) 0.045(2) Uani 0.50 d PDU 1 H25A H -0.9175(4) 0.7556(15) 1.0153(2) 0.054 Uiso 0.50 calc PR 1 C25B C -0.8750(5) 0.7749(13) 0.9874(2) 0.041(2) Uani 0.50 d PDU 2 H25B H -0.8697(5) 0.9198(13) 1.0006(2) 0.049 Uiso 0.50 calc PR 2 N1' N 0.0224(2) 0.8232(5) 0.84558(5) 0.0307(6) Uani 1 d . . H1' H 0.0444(21) 0.9920(64) 0.8420(6) 0.041(9) Uiso 1 d . . O1' O 0.1498(2) 0.4691(5) 0.74560(5) 0.0528(7) Uani 1 d . . O2' O 0.0456(2) 0.3814(4) 0.83597(6) 0.0542(7) Uani 1 d . . C1' C 0.2148(2) 0.5829(7) 0.72754(7) 0.0430(9) Uani 1 d . . C2' C 0.2255(3) 0.5221(8) 0.69754(8) 0.0608(11) Uani 1 d . . H2' H 0.1858(3) 0.3958(8) 0.68816(8) 0.073 Uiso 1 calc R . C3' C 0.2951(3) 0.6475(10) 0.68091(9) 0.0737(13) Uani 1 d . . H3' H 0.3021(3) 0.6009(10) 0.66066(9) 0.088 Uiso 1 calc R . C4' C 0.3530(3) 0.8362(9) 0.69368(8) 0.0650(12) Uani 1 d . . H4' H 0.3990(3) 0.9182(9) 0.68220(8) 0.078 Uiso 1 calc R . C5' C 0.4018(2) 1.1060(7) 0.73811(9) 0.0531(10) Uani 1 d . . H5' H 0.4469(2) 1.1910(7) 0.72652(9) 0.064 Uiso 1 calc R . C6' C 0.3940(2) 1.1757(7) 0.76790(9) 0.0526(10) Uani 1 d . . H6' H 0.4342(2) 1.3047(7) 0.77653(9) 0.063 Uiso 1 calc R . C7' C 0.3255(2) 1.0531(6) 0.78536(8) 0.0428(8) Uani 1 d . . H7' H 0.3202(2) 1.1022(6) 0.80561(8) 0.051 Uiso 1 calc R . C8' C 0.2658(2) 0.8611(6) 0.77314(7) 0.0320(7) Uani 1 d . . C9' C 0.3432(2) 0.9084(7) 0.72457(7) 0.0451(9) Uani 1 d . . C10' C 0.2741(2) 0.7806(6) 0.74208(7) 0.0352(8) Uani 1 d . . C11' C 0.1945(2) 0.7597(6) 0.79288(7) 0.0319(7) Uani 1 d . . C12' C 0.1388(2) 0.6974(6) 0.81155(7) 0.0330(7) Uani 1 d . . C13' C 0.0655(2) 0.6164(6) 0.83191(7) 0.0329(7) Uani 1 d . . C18' C 0.0844(3) 0.2810(8) 0.73263(9) 0.0727(13) Uani 1 d . . H18D H 0.0429(12) 0.2184(41) 0.7480(2) 0.109 Uiso 1 calc R . H18E H 0.1187(3) 0.1325(27) 0.7246(5) 0.109 Uiso 1 calc R . H18F H 0.0473(13) 0.3649(17) 0.7166(4) 0.109 Uiso 1 calc R . C20' C -0.0541(2) 0.8080(6) 0.86604(6) 0.0296(7) Uani 1 d . . C21' C -0.0582(2) 1.0039(6) 0.88835(6) 0.0352(8) Uani 1 d . . H21' H -0.0112(2) 1.1343(6) 0.89007(6) 0.042 Uiso 1 calc R . C22' C -0.1330(2) 1.0031(6) 0.90799(6) 0.0379(8) Uani 1 d . . H22' H -0.1358(2) 1.1340(6) 0.92294(6) 0.045 Uiso 1 calc R . C23' C -0.2032(2) 0.8119(7) 0.90575(7) 0.0392(8) Uani 1 d . . H23' H -0.2532 0.8127 0.9191 0.047 Uiso 1 d . . C24' C -0.1983(2) 0.6175(6) 0.88337(7) 0.0394(8) Uani 1 d . . H24' H -0.2456(2) 0.4880(6) 0.88161(7) 0.047 Uiso 1 calc R . C25' C -0.1238(2) 0.6142(6) 0.86366(7) 0.0324(7) Uani 1 d . . H25' H -0.1208(2) 0.4820(6) 0.84886(7) 0.039 Uiso 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 N1 0.044(2) 0.0216(15) 0.039(2) 0.0004(13) -0.0083(13) 0.0003(13) O1 0.0484(14) 0.061(2) 0.0394(13) 0.0021(13) -0.0066(11) -0.0054(13) O2 0.068(2) 0.0218(12) 0.0418(13) 0.0018(10) -0.0138(11) 0.0013(12) C1 0.037(2) 0.058(2) 0.032(2) -0.012(2) -0.0036(15) 0.008(2) C2 0.036(2) 0.068(3) 0.044(2) -0.016(2) 0.004(2) 0.001(2) C3 0.037(2) 0.081(3) 0.054(2) -0.022(2) -0.003(2) 0.005(2) C4 0.041(2) 0.074(3) 0.045(2) -0.020(2) -0.012(2) 0.017(2) C5 0.056(2) 0.058(2) 0.036(2) -0.009(2) -0.011(2) 0.026(2) C6 0.059(2) 0.053(2) 0.039(2) 0.003(2) 0.002(2) 0.020(2) C7 0.048(2) 0.047(2) 0.038(2) -0.002(2) -0.005(2) 0.011(2) C8 0.038(2) 0.046(2) 0.030(2) -0.008(2) -0.0037(15) 0.016(2) C9 0.042(2) 0.058(2) 0.035(2) -0.018(2) -0.006(2) 0.018(2) C10 0.038(2) 0.046(2) 0.031(2) -0.011(2) -0.0035(15) 0.014(2) C11 0.039(2) 0.037(2) 0.035(2) -0.005(2) 0.000(2) 0.006(2) C12 0.038(2) 0.031(2) 0.033(2) -0.0040(15) 0.001(2) 0.001(2) C13 0.035(2) 0.026(2) 0.030(2) 0.0010(14) 0.0029(14) -0.0022(15) C18 0.056(2) 0.062(3) 0.043(2) 0.004(2) 0.007(2) -0.004(2) C20 0.038(2) 0.021(2) 0.037(2) 0.0060(14) -0.0024(15) -0.0030(15) C21A 0.040(5) 0.032(5) 0.039(4) -0.004(4) 0.000(4) -0.004(4) C21B 0.045(6) 0.026(4) 0.034(4) 0.007(4) -0.002(4) 0.007(4) C22A 0.057(5) 0.048(6) 0.036(5) -0.014(4) 0.006(4) -0.003(5) C22B 0.054(6) 0.049(5) 0.035(5) -0.004(4) -0.014(4) 0.006(5) C23 0.053(2) 0.045(2) 0.047(2) 0.004(2) -0.014(2) -0.002(2) C24A 0.030(4) 0.036(5) 0.068(5) 0.000(4) -0.009(4) -0.007(4) C24B 0.035(5) 0.026(4) 0.074(6) 0.011(4) -0.014(4) 0.005(4) C25A 0.034(4) 0.055(6) 0.046(5) -0.012(4) 0.005(4) 0.005(4) C25B 0.034(5) 0.041(5) 0.047(5) -0.017(4) -0.005(4) 0.000(4) N1' 0.0351(15) 0.0201(15) 0.0369(15) 0.0012(12) 0.0016(12) -0.0045(13) O1' 0.0490(14) 0.055(2) 0.0533(14) -0.0100(13) -0.0126(12) -0.0169(13) O2' 0.055(2) 0.0247(13) 0.084(2) 0.0045(12) 0.0277(13) -0.0021(12) C1' 0.043(2) 0.043(2) 0.042(2) -0.003(2) -0.009(2) 0.009(2) C2' 0.072(3) 0.066(3) 0.043(2) -0.009(2) -0.014(2) 0.021(2) C3' 0.092(3) 0.094(4) 0.035(2) -0.002(2) 0.000(2) 0.040(3) C4' 0.067(3) 0.081(3) 0.048(2) 0.018(2) 0.018(2) 0.023(3) C5' 0.040(2) 0.049(2) 0.072(3) 0.021(2) 0.020(2) 0.004(2) C6' 0.038(2) 0.040(2) 0.079(3) -0.003(2) 0.005(2) -0.007(2) C7' 0.036(2) 0.043(2) 0.050(2) -0.006(2) 0.007(2) -0.002(2) C8' 0.026(2) 0.033(2) 0.038(2) 0.000(2) 0.0007(14) 0.0018(15) C9' 0.042(2) 0.047(2) 0.047(2) 0.015(2) 0.009(2) 0.014(2) C10' 0.036(2) 0.033(2) 0.036(2) 0.006(2) -0.0036(15) 0.008(2) C11' 0.029(2) 0.030(2) 0.036(2) -0.0034(15) -0.0083(15) -0.0014(15) C12' 0.029(2) 0.031(2) 0.038(2) 0.0011(15) 0.000(2) -0.0007(15) C13' 0.031(2) 0.031(2) 0.036(2) 0.004(2) -0.0039(14) -0.001(2) C18' 0.061(3) 0.060(3) 0.095(3) -0.023(2) -0.029(2) -0.007(2) C20' 0.031(2) 0.029(2) 0.029(2) 0.0077(14) -0.0021(13) 0.0023(15) C21' 0.037(2) 0.032(2) 0.036(2) 0.0030(15) -0.0037(15) 0.000(2) C22' 0.049(2) 0.034(2) 0.030(2) 0.0000(15) 0.003(2) 0.004(2) C23' 0.040(2) 0.038(2) 0.040(2) 0.009(2) 0.008(2) 0.005(2) C24' 0.034(2) 0.031(2) 0.054(2) 0.007(2) 0.003(2) -0.001(2) C25' 0.033(2) 0.025(2) 0.039(2) 0.0001(14) 0.0011(14) 0.0001(15) _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 N1 C13 1.345(4) . ? N1 C20 1.429(4) . ? O1 C1 1.366(4) . ? O1 C18 1.421(4) . ? O2 C13 1.222(4) . ? C1 C2 1.377(5) . ? C1 C10 1.427(5) . ? C2 C3 1.405(5) . ? C3 C4 1.352(5) . ? C4 C9 1.416(5) . ? C5 C6 1.353(5) . ? C5 C9 1.411(5) . ? C6 C7 1.400(4) . ? C7 C8 1.376(5) . ? C8 C10 1.433(5) . ? C8 C11 1.443(4) . ? C9 C10 1.432(4) . ? C11 C12 1.192(4) . ? C12 C13 1.453(4) . ? C20 C21A 1.373(6) . ? C20 C25A 1.374(6) . ? C20 C21B 1.375(6) . ? C20 C25B 1.388(6) . ? C21A C22A 1.382(7) . ? C21B C22B 1.382(7) . ? C22A C23 1.366(7) . ? C22B C23 1.371(7) . ? C23 C24B 1.371(6) . ? C23 C24A 1.400(6) . ? C24A C25A 1.390(7) . ? C24B C25B 1.384(7) . ? N1' C13' 1.350(4) . ? N1' C20' 1.429(4) . ? O1' C1' 1.358(4) . ? O1' C18' 1.421(4) . ? O2' C13' 1.223(4) . ? C1' C2' 1.368(5) . ? C1' C10' 1.430(5) . ? C2' C3' 1.392(6) . ? C3' C4' 1.355(6) . ? C4' C9' 1.418(5) . ? C5' C6' 1.365(5) . ? C5' C9' 1.405(5) . ? C6' C7' 1.395(4) . ? C7' C8' 1.372(4) . ? C8' C10' 1.434(4) . ? C8' C11' 1.441(4) . ? C9' C10' 1.414(4) . ? C11' C12' 1.197(4) . ? C12' C13' 1.447(4) . ? C20' C25' 1.380(4) . ? C20' C21' 1.390(4) . ? C21' C22' 1.384(4) . ? C22' C23' 1.376(5) . ? C23' C24' 1.387(4) . ? C24' C25' 1.383(4) . ? 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 C13 N1 C20 125.3(3) . . ? C1 O1 C18 118.7(3) . . ? O1 C1 C2 123.0(3) . . ? O1 C1 C10 115.4(3) . . ? C2 C1 C10 121.6(3) . . ? C1 C2 C3 119.3(4) . . ? C4 C3 C2 121.5(4) . . ? C3 C4 C9 120.8(3) . . ? C6 C5 C9 121.8(3) . . ? C5 C6 C7 119.7(4) . . ? C8 C7 C6 121.5(3) . . ? C7 C8 C10 119.9(3) . . ? C7 C8 C11 116.8(3) . . ? C10 C8 C11 123.2(3) . . ? C5 C9 C4 121.5(3) . . ? C5 C9 C10 119.2(3) . . ? C4 C9 C10 119.4(4) . . ? C1 C10 C9 117.5(3) . . ? C1 C10 C8 124.7(3) . . ? C9 C10 C8 117.9(3) . . ? C12 C11 C8 175.2(4) . . ? C11 C12 C13 170.4(3) . . ? O2 C13 N1 123.8(3) . . ? O2 C13 C12 121.0(3) . . ? N1 C13 C12 115.2(3) . . ? C21A C20 C25A 121.9(6) . . ? C21B C20 C25B 118.1(6) . . ? C21A C20 N1 118.7(5) . . ? C25A C20 N1 119.2(4) . . ? C21B C20 N1 118.8(4) . . ? C25B C20 N1 123.1(4) . . ? C20 C21A C22A 119.2(8) . . ? C20 C21B C22B 121.5(8) . . ? C23 C22A C21A 121.2(9) . . ? C23 C22B C21B 118.8(9) . . ? C22B C23 C24B 121.6(6) . . ? C22A C23 C24A 118.2(6) . . ? C25A C24A C23 121.6(7) . . ? C23 C24B C25B 118.5(6) . . ? C20 C25A C24A 117.6(7) . . ? C24B C25B C20 121.3(6) . . ? C13' N1' C20' 126.8(3) . . ? C1' O1' C18' 118.8(3) . . ? O1' C1' C2' 124.8(3) . . ? O1' C1' C10' 115.0(3) . . ? C2' C1' C10' 120.3(4) . . ? C1' C2' C3' 120.6(4) . . ? C4' C3' C2' 121.3(4) . . ? C3' C4' C9' 119.9(4) . . ? C6' C5' C9' 121.4(3) . . ? C5' C6' C7' 119.8(3) . . ? C8' C7' C6' 121.1(3) . . ? C7' C8' C10' 120.1(3) . . ? C7' C8' C11' 116.0(3) . . ? C10' C8' C11' 123.8(3) . . ? C5' C9' C10' 119.4(3) . . ? C5' C9' C4' 120.7(4) . . ? C10' C9' C4' 119.9(4) . . ? C9' C10' C1' 118.0(3) . . ? C9' C10' C8' 118.2(3) . . ? C1' C10' C8' 123.7(3) . . ? C12' C11' C8' 172.6(3) . . ? C11' C12' C13' 174.9(3) . . ? O2' C13' N1' 124.3(3) . . ? O2' C13' C12' 122.1(3) . . ? N1' C13' C12' 113.7(3) . . ? C25' C20' C21' 120.1(3) . . ? C25' C20' N1' 122.6(3) . . ? C21' C20' N1' 117.3(3) . . ? C22' C21' C20' 119.4(3) . . ? C23' C22' C21' 121.1(3) . . ? C22' C23' C24' 119.0(3) . . ? C25' C24' C23' 120.8(3) . . ? C20' C25' C24' 119.7(3) . . ? _refine_diff_density_max 0.166 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.042 #===END data_nit-19 _database_code_CSD 178496 _audit_creation_method SHELXL _chemical_name_systematic ; 3-(8-methoxynaphth-1-yl)-prop-2-ynenitrile ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H9 N O' _chemical_formula_weight 207.22 _chemical_melting_point 370-371 _chemical_compound_source ? 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.9353(2) _cell_length_b 11.2675(9) _cell_length_c 23.736(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.519(4) _cell_angle_gamma 90.00 _cell_volume 1050.48(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2059 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 27.45 _exptl_crystal_description needles _exptl_crystal_colour white _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.125 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method ? _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.926 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R. H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKa _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Phi and Omega scans to fill Ewald sphere' _diffrn_measurement_method 'Enraf Nonius KappaCCD area detector' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12879 _diffrn_reflns_av_R_equivalents 0.0900 _diffrn_reflns_av_sigmaI/netI 0.0787 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2361 _reflns_number_observed 1336 _reflns_observed_criterion >2sigma(I) _computing_data_collection ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_cell_refinement ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_data_reduction ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEP3 (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 302 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[s^2^(Fo^2^)+( 0.0712P)^2^+0.0000P] 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 ? _refine_ls_number_reflns 2059 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1218 _refine_ls_R_factor_obs 0.0562 _refine_ls_wR_factor_all 0.1479 _refine_ls_wR_factor_obs 0.1194 _refine_ls_goodness_of_fit_all 1.010 _refine_ls_goodness_of_fit_obs 1.138 _refine_ls_restrained_S_all 1.031 _refine_ls_restrained_S_obs 1.138 _refine_ls_shift/esd_max 0.062 _refine_ls_shift/esd_mean 0.006 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.4446(3) 0.37320(12) 0.18369(5) 0.0383(4) Uani 1 d . . N1 N 1.1106(5) 0.7360(2) 0.16134(9) 0.0638(6) Uani 1 d . . C1 C 0.3587(4) 0.2692(2) 0.15758(8) 0.0332(5) Uani 1 d . . C2 C 0.2083(5) 0.1754(2) 0.18340(9) 0.0392(5) Uani 1 d . . C3 C 0.1278(5) 0.0712(2) 0.15256(10) 0.0418(6) Uani 1 d . . C4 C 0.1867(5) 0.0631(2) 0.09701(9) 0.0394(5) Uani 1 d . . C5 C 0.3884(5) 0.1531(2) 0.01056(9) 0.0363(5) Uani 1 d . . C6 C 0.5371(5) 0.2444(2) -0.01682(9) 0.0385(5) Uani 1 d . . C7 C 0.6438(5) 0.3456(2) 0.01286(8) 0.0338(5) Uani 1 d . . C8 C 0.5954(4) 0.3563(2) 0.07006(8) 0.0303(5) Uani 1 d . . C9 C 0.3363(4) 0.1587(2) 0.06884(8) 0.0325(5) Uani 1 d . . C10 C 0.4328(4) 0.2631(2) 0.09949(8) 0.0300(5) Uani 1 d . . C11 C 0.7262(4) 0.4618(2) 0.09713(8) 0.0336(5) Uani 1 d . . C12 C 0.8547(5) 0.5518(2) 0.11545(8) 0.0365(5) Uani 1 d . . C13 C 0.9927(5) 0.6519(2) 0.14053(9) 0.0424(5) Uani 1 d . . C18 C 0.3196(6) 0.3950(2) 0.23811(9) 0.0454(6) Uani 1 d . . H2 H 0.1633(43) 0.1820(16) 0.2240(8) 0.036(5) Uiso 1 d . . H3 H 0.0227(47) 0.0054(18) 0.1708(8) 0.043(6) Uiso 1 d . . H4 H 0.1281(47) -0.0100(19) 0.0752(8) 0.043(5) Uiso 1 d . . H5 H 0.3140(46) 0.0836(17) -0.0111(8) 0.036(5) Uiso 1 d . . H6 H 0.5780(45) 0.2389(17) -0.0579(9) 0.039(5) Uiso 1 d . . H7 H 0.7574(47) 0.4135(17) -0.0069(8) 0.040(5) Uiso 1 d . . H18A H 0.4191(49) 0.3378(19) 0.2676(9) 0.044(6) Uiso 1 d . . H18B H 0.3889(51) 0.4781(21) 0.2473(8) 0.049(6) Uiso 1 d . . H18C H 0.0641(59) 0.3848(18) 0.2358(8) 0.053(6) Uiso 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 O1 0.0418(8) 0.0419(9) 0.0316(8) -0.0024(6) 0.0064(6) -0.0031(6) N1 0.0652(13) 0.0606(14) 0.0670(15) -0.0215(12) 0.0140(11) -0.0182(11) C1 0.0294(9) 0.0335(12) 0.0363(11) 0.0008(9) -0.0015(8) 0.0017(9) C2 0.0350(11) 0.0455(14) 0.0368(13) 0.0094(10) 0.0014(9) 0.0005(10) C3 0.0386(11) 0.0365(13) 0.0503(15) 0.0117(10) 0.0020(10) -0.0048(10) C4 0.0365(11) 0.0311(12) 0.0499(14) 0.0002(10) -0.0042(10) -0.0004(9) C5 0.0350(11) 0.0324(12) 0.0408(13) -0.0061(10) -0.0042(9) 0.0053(9) C6 0.0407(11) 0.0415(13) 0.0334(13) -0.0025(10) 0.0020(9) 0.0093(10) C7 0.0337(10) 0.0324(12) 0.0354(12) 0.0045(9) 0.0023(8) 0.0058(9) C8 0.0290(9) 0.0284(11) 0.0332(11) -0.0004(8) -0.0007(8) 0.0046(8) C9 0.0294(10) 0.0281(11) 0.0395(12) 0.0017(9) -0.0029(8) 0.0049(8) C10 0.0258(9) 0.0292(11) 0.0346(11) 0.0039(8) -0.0014(8) 0.0058(8) C11 0.0318(10) 0.0361(13) 0.0332(11) 0.0061(9) 0.0049(8) 0.0038(9) C12 0.0391(11) 0.0346(13) 0.0359(12) 0.0020(10) 0.0037(9) -0.0025(10) C13 0.0431(12) 0.0453(14) 0.0395(12) -0.0021(11) 0.0091(9) -0.0033(11) C18 0.0455(14) 0.056(2) 0.0346(13) -0.0056(12) 0.0053(10) -0.0033(12) _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 C1 1.359(2) . ? O1 C18 1.431(2) . ? N1 C13 1.153(3) . ? C1 C2 1.374(3) . ? C1 C10 1.428(3) . ? C2 C3 1.409(3) . ? C3 C4 1.356(3) . ? C4 C9 1.414(3) . ? C5 C6 1.367(3) . ? C5 C9 1.412(3) . ? C6 C7 1.392(3) . ? C7 C8 1.388(3) . ? C8 C11 1.431(3) . ? C8 C10 1.434(3) . ? C9 C10 1.422(3) . ? C11 C12 1.203(3) . ? C12 C13 1.372(3) . ? 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 O1 C18 118.0(2) . . ? O1 C1 C2 124.2(2) . . ? O1 C1 C10 115.0(2) . . ? C2 C1 C10 120.8(2) . . ? C1 C2 C3 119.9(2) . . ? C4 C3 C2 121.0(2) . . ? C3 C4 C9 120.6(2) . . ? C6 C5 C9 121.6(2) . . ? C5 C6 C7 120.0(2) . . ? C8 C7 C6 120.7(2) . . ? C7 C8 C11 116.4(2) . . ? C7 C8 C10 120.3(2) . . ? C11 C8 C10 123.2(2) . . ? C5 C9 C4 121.2(2) . . ? C5 C9 C10 119.2(2) . . ? C4 C9 C10 119.6(2) . . ? C9 C10 C1 118.0(2) . . ? C9 C10 C8 118.0(2) . . ? C1 C10 C8 124.0(2) . . ? C12 C11 C8 173.7(2) . . ? C11 C12 C13 175.4(2) . . ? N1 C13 C12 179.5(2) . . ? _refine_diff_density_max 0.271 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.095 #===END data_dimethylamino-36 _database_code_CSD 178497 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 8-Dimethylamino-1-(triphenylsilylethynyl)naphthalene ; _chemical_name_common ? _chemical_melting_point 393-394 _chemical_formula_moiety ? _chemical_formula_sum 'C32 H27 N Si' _chemical_formula_weight 453.64 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' 'Si' 'Si' 0.0817 0.0704 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2787(2) _cell_length_b 9.0356(2) _cell_length_c 18.6385(7) _cell_angle_alpha 80.0224(10) _cell_angle_beta 80.9641(10) _cell_angle_gamma 65.704(2) _cell_volume 1245.79(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11459 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.449 _exptl_absorpt_correction_T_max 0.449 _exptl_absorpt_process_details ? _exptl_special_details ; using multiple and symmetry-related data measurements via the program SORTAV (Blessing, Acta Cryst. 1995, A51, 33-38) ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18940 _diffrn_reflns_av_R_equivalents 0.0806 _diffrn_reflns_av_sigmaI/netI 0.0728 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.53 _reflns_number_total 5619 _reflns_number_gt 3974 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson and Burnett, 1996)' _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^)+(0.1126P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5619 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0929 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1704 _refine_ls_wR_factor_gt 0.1574 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.001 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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Si1 Si 0.67617(6) 0.12721(6) 0.19010(3) 0.02566(17) Uani 1 1 d . . . N1 N 0.1945(2) 0.2672(2) 0.36007(9) 0.0326(4) Uani 1 1 d . . . C1 C 0.1760(2) 0.1855(2) 0.43145(10) 0.0298(4) Uani 1 1 d . . . C2 C 0.0419(3) 0.2597(3) 0.48347(12) 0.0387(5) Uani 1 1 d . . . C3 C 0.0202(3) 0.1736(3) 0.55290(12) 0.0428(5) Uani 1 1 d . . . C4 C 0.1289(3) 0.0169(3) 0.56925(11) 0.0389(5) Uani 1 1 d . . . C5 C 0.3886(3) -0.2273(3) 0.53767(11) 0.0383(5) Uani 1 1 d . . . C6 C 0.5331(3) -0.3061(3) 0.49178(12) 0.0382(5) Uani 1 1 d . . . C7 C 0.5694(3) -0.2209(2) 0.42532(11) 0.0318(4) Uani 1 1 d . . . C8 C 0.4597(2) -0.0618(2) 0.40338(9) 0.0254(4) Uani 1 1 d . . . C9 C 0.3021(2) 0.0222(2) 0.44930(9) 0.0261(4) Uani 1 1 d . . . C10 C 0.2733(3) -0.0642(3) 0.51875(9) 0.0306(4) Uani 1 1 d . . . C11 C 0.5187(2) 0.0107(2) 0.33515(9) 0.0271(4) Uani 1 1 d . . . C12 C 0.5870(2) 0.0530(2) 0.27734(10) 0.0310(4) Uani 1 1 d . . . C13 C 0.5176(2) 0.1717(2) 0.12034(10) 0.0284(4) Uani 1 1 d . . . C14 C 0.4260(4) 0.0727(3) 0.12106(13) 0.0523(7) Uani 1 1 d . . . C15 C 0.3076(4) 0.1053(4) 0.06944(15) 0.0627(8) Uani 1 1 d . . . C16 C 0.2781(3) 0.2374(3) 0.01713(12) 0.0468(6) Uani 1 1 d . . . C17 C 0.3666(4) 0.3359(4) 0.01515(14) 0.0564(7) Uani 1 1 d . . . C18 C 0.4855(3) 0.3039(3) 0.06659(13) 0.0469(6) Uani 1 1 d . . . C19 C 0.8974(2) -0.0345(2) 0.16456(10) 0.0283(4) Uani 1 1 d . . . C20 C 1.0224(3) -0.1042(3) 0.21571(12) 0.0411(5) Uani 1 1 d . . . C21 C 1.1877(3) -0.2239(3) 0.20028(14) 0.0529(6) Uani 1 1 d . . . C22 C 1.2320(4) -0.2787(4) 0.13264(17) 0.0629(8) Uani 1 1 d . . . C23 C 1.1111(3) -0.2121(4) 0.08056(16) 0.0613(7) Uani 1 1 d . . . C24 C 0.9468(3) -0.0904(3) 0.09613(12) 0.0410(5) Uani 1 1 d . . . C25 C 0.7076(3) 0.3147(2) 0.20148(10) 0.0326(4) Uani 1 1 d . . . C26 C 0.8358(3) 0.3600(3) 0.15679(13) 0.0442(6) Uani 1 1 d . . . C27 C 0.8587(5) 0.4997(4) 0.16497(18) 0.0659(9) Uani 1 1 d . . . C28 C 0.7557(5) 0.5962(3) 0.2178(2) 0.0749(11) Uani 1 1 d . . . C29 C 0.6294(5) 0.5542(3) 0.2626(2) 0.0689(10) Uani 1 1 d . . . C30 C 0.6036(3) 0.4143(3) 0.25476(14) 0.0467(6) Uani 1 1 d . . . C31 C 0.1395(3) 0.2079(3) 0.30361(12) 0.0406(5) Uani 1 1 d . . . C32 C 0.1189(4) 0.4434(3) 0.35344(16) 0.0507(6) Uani 1 1 d . . . H2 H -0.040(3) 0.373(3) 0.4679(13) 0.045(6) Uiso 1 1 d . . . H3 H -0.077(4) 0.230(3) 0.5891(16) 0.067(8) Uiso 1 1 d . . . H4 H 0.112(3) -0.044(3) 0.6172(16) 0.069(8) Uiso 1 1 d . . . H5 H 0.362(3) -0.287(3) 0.5858(14) 0.057(7) Uiso 1 1 d . . . H6 H 0.611(3) -0.416(3) 0.5032(13) 0.040(6) Uiso 1 1 d . . . H7 H 0.672(3) -0.273(3) 0.3941(13) 0.047(6) Uiso 1 1 d . . . H14 H 0.464(4) -0.032(4) 0.1527(18) 0.087(10) Uiso 1 1 d . . . H15 H 0.247(3) 0.034(3) 0.0686(14) 0.061(7) Uiso 1 1 d . . . H16 H 0.175(4) 0.270(3) -0.0178(16) 0.069(8) Uiso 1 1 d . . . H17 H 0.333(4) 0.444(4) -0.0196(17) 0.079(9) Uiso 1 1 d . . . H18 H 0.548(3) 0.385(3) 0.0637(14) 0.057(7) Uiso 1 1 d . . . H20 H 0.990(3) -0.069(3) 0.2620(16) 0.062(8) Uiso 1 1 d . . . H21 H 1.281(3) -0.274(3) 0.2368(15) 0.062(7) Uiso 1 1 d . . . H22 H 1.335(4) -0.365(4) 0.1214(16) 0.077(9) Uiso 1 1 d . . . H23 H 1.143(5) -0.244(4) 0.031(2) 0.106(12) Uiso 1 1 d . . . H24 H 0.860(3) -0.037(3) 0.0580(15) 0.063(8) Uiso 1 1 d . . . H26 H 0.911(3) 0.292(3) 0.1244(14) 0.047(7) Uiso 1 1 d . . . H27 H 0.952(4) 0.531(4) 0.1349(17) 0.077(9) Uiso 1 1 d . . . H28 H 0.772(4) 0.696(4) 0.2274(18) 0.096(10) Uiso 1 1 d . . . H29 H 0.559(4) 0.610(4) 0.2972(16) 0.065(9) Uiso 1 1 d . . . H30 H 0.512(4) 0.381(3) 0.2856(15) 0.058(8) Uiso 1 1 d . . . H31A H 0.005(3) 0.253(3) 0.3051(13) 0.050(6) Uiso 1 1 d . . . H31B H 0.191(3) 0.078(3) 0.3108(13) 0.046(6) Uiso 1 1 d . . . H31C H 0.186(3) 0.250(3) 0.2536(15) 0.059(7) Uiso 1 1 d . . . H32A H -0.010(3) 0.490(3) 0.3563(13) 0.048(7) Uiso 1 1 d . . . H32B H 0.163(3) 0.483(3) 0.3919(15) 0.060(7) Uiso 1 1 d . . . H32C H 0.171(3) 0.484(3) 0.3029(14) 0.053(7) 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 0.0284(3) 0.0355(3) 0.0140(3) -0.0038(2) -0.00131(19) -0.0135(2) N1 0.0343(9) 0.0379(10) 0.0238(8) 0.0007(7) -0.0044(7) -0.0135(7) C1 0.0315(10) 0.0411(11) 0.0210(9) -0.0068(8) -0.0007(7) -0.0180(9) C2 0.0333(11) 0.0481(14) 0.0365(12) -0.0134(10) 0.0013(9) -0.0163(10) C3 0.0405(12) 0.0693(17) 0.0275(11) -0.0213(11) 0.0096(9) -0.0290(12) C4 0.0465(12) 0.0663(16) 0.0171(10) -0.0093(10) 0.0053(8) -0.0368(12) C5 0.0495(13) 0.0527(14) 0.0228(11) 0.0064(9) -0.0100(9) -0.0324(11) C6 0.0468(12) 0.0380(12) 0.0333(12) 0.0042(10) -0.0136(9) -0.0200(10) C7 0.0355(11) 0.0370(11) 0.0256(10) -0.0050(9) -0.0045(8) -0.0160(9) C8 0.0311(9) 0.0354(10) 0.0155(9) -0.0041(7) -0.0027(7) -0.0183(8) C9 0.0320(10) 0.0389(11) 0.0145(8) -0.0053(8) -0.0012(7) -0.0208(8) C10 0.0392(10) 0.0500(12) 0.0141(9) -0.0044(8) -0.0027(7) -0.0288(10) C11 0.0264(9) 0.0396(11) 0.0167(9) -0.0066(8) -0.0002(7) -0.0138(8) C12 0.0288(9) 0.0418(12) 0.0230(10) -0.0076(8) -0.0029(7) -0.0130(8) C13 0.0297(9) 0.0387(11) 0.0169(9) -0.0051(8) 0.0013(7) -0.0142(8) C14 0.0693(16) 0.0652(17) 0.0401(13) 0.0167(12) -0.0271(12) -0.0455(14) C15 0.0754(19) 0.083(2) 0.0547(16) 0.0172(14) -0.0356(14) -0.0558(17) C16 0.0504(13) 0.0673(16) 0.0307(12) 0.0052(11) -0.0186(10) -0.0303(12) C17 0.0676(16) 0.0671(17) 0.0422(14) 0.0200(13) -0.0301(12) -0.0357(14) C18 0.0558(14) 0.0508(14) 0.0421(13) 0.0121(11) -0.0229(11) -0.0295(12) C19 0.0324(10) 0.0351(11) 0.0195(9) -0.0045(8) 0.0005(7) -0.0159(8) C20 0.0392(11) 0.0518(14) 0.0249(11) -0.0019(10) -0.0030(9) -0.0117(10) C21 0.0379(12) 0.0578(16) 0.0468(15) 0.0043(12) -0.0064(11) -0.0059(11) C22 0.0435(14) 0.0587(17) 0.0636(19) -0.0132(14) 0.0110(13) -0.0008(13) C23 0.0532(15) 0.0738(19) 0.0466(16) -0.0297(14) 0.0132(12) -0.0125(13) C24 0.0406(12) 0.0567(14) 0.0274(11) -0.0151(10) 0.0041(9) -0.0196(10) C25 0.0412(11) 0.0345(11) 0.0241(10) -0.0014(8) -0.0153(8) -0.0134(9) C26 0.0615(15) 0.0510(14) 0.0296(12) 0.0090(10) -0.0180(11) -0.0324(12) C27 0.098(2) 0.0653(19) 0.0598(18) 0.0295(15) -0.0511(17) -0.0569(18) C28 0.104(3) 0.0390(15) 0.099(3) 0.0099(16) -0.077(2) -0.0294(16) C29 0.0681(18) 0.0461(16) 0.091(2) -0.0319(17) -0.0495(18) 0.0030(14) C30 0.0396(12) 0.0493(14) 0.0508(14) -0.0201(11) -0.0216(11) -0.0055(10) C31 0.0364(12) 0.0607(16) 0.0236(11) 0.0013(10) -0.0080(8) -0.0187(11) C32 0.0487(15) 0.0400(14) 0.0523(16) 0.0025(12) -0.0053(12) -0.0093(11) _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 C12 1.814(2) . ? Si1 C19 1.8656(19) . ? Si1 C25 1.867(2) . ? Si1 C13 1.8698(18) . ? N1 C1 1.424(2) . ? N1 C32 1.442(3) . ? N1 C31 1.465(3) . ? N1 C11 2.766(2) . ? C1 C2 1.378(3) . ? C1 C9 1.431(3) . ? C2 C3 1.416(3) . ? C3 C4 1.340(3) . ? C4 C10 1.420(3) . ? C5 C6 1.363(3) . ? C5 C10 1.406(3) . ? C6 C7 1.400(3) . ? C7 C8 1.377(3) . ? C8 C11 1.437(2) . ? C8 C9 1.439(3) . ? C9 C10 1.431(3) . ? C11 C12 1.212(3) . ? C13 C18 1.382(3) . ? C13 C14 1.389(3) . ? C14 C15 1.390(3) . ? C15 C16 1.366(3) . ? C16 C17 1.359(3) . ? C17 C18 1.393(3) . ? C19 C24 1.392(3) . ? C19 C20 1.394(3) . ? C20 C21 1.375(3) . ? C21 C22 1.375(4) . ? C22 C23 1.383(4) . ? C23 C24 1.378(3) . ? C25 C30 1.393(3) . ? C25 C26 1.397(3) . ? C26 C27 1.387(3) . ? C27 C28 1.371(5) . ? C28 C29 1.370(5) . ? C29 C30 1.399(4) . ? 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 C12 Si1 C19 107.92(9) . . ? C12 Si1 C25 108.50(9) . . ? C19 Si1 C25 108.95(8) . . ? C12 Si1 C13 108.83(8) . . ? C19 Si1 C13 111.18(8) . . ? C25 Si1 C13 111.36(8) . . ? C1 N1 C32 115.97(18) . . ? C1 N1 C31 113.23(16) . . ? C32 N1 C31 111.22(19) . . ? C1 N1 C11 88.40(11) . . ? C32 N1 C11 139.71(14) . . ? C31 N1 C11 84.25(12) . . ? C2 C1 N1 121.86(19) . . ? C2 C1 C9 119.54(19) . . ? N1 C1 C9 118.59(16) . . ? C1 C2 C3 121.0(2) . . ? C4 C3 C2 120.6(2) . . ? C3 C4 C10 120.8(2) . . ? C6 C5 C10 121.38(19) . . ? C5 C6 C7 119.1(2) . . ? C8 C7 C6 122.09(19) . . ? C7 C8 C11 115.39(16) . . ? C7 C8 C9 120.05(17) . . ? C11 C8 C9 124.51(17) . . ? C10 C9 C1 118.16(17) . . ? C10 C9 C8 116.80(17) . . ? C1 C9 C8 125.02(16) . . ? C5 C10 C4 119.97(18) . . ? C5 C10 C9 120.46(18) . . ? C4 C10 C9 119.6(2) . . ? C12 C11 C8 171.7(2) . . ? C12 C11 N1 105.94(14) . . ? C8 C11 N1 82.36(11) . . ? C11 C12 Si1 176.45(18) . . ? C18 C13 C14 117.28(18) . . ? C18 C13 Si1 121.87(15) . . ? C14 C13 Si1 120.85(15) . . ? C13 C14 C15 121.1(2) . . ? C16 C15 C14 120.2(2) . . ? C17 C16 C15 119.7(2) . . ? C16 C17 C18 120.4(2) . . ? C13 C18 C17 121.2(2) . . ? C24 C19 C20 117.17(19) . . ? C24 C19 Si1 123.54(15) . . ? C20 C19 Si1 119.30(14) . . ? C21 C20 C19 122.1(2) . . ? C20 C21 C22 119.5(2) . . ? C21 C22 C23 119.9(2) . . ? C24 C23 C22 120.2(2) . . ? C23 C24 C19 121.1(2) . . ? C30 C25 C26 117.7(2) . . ? C30 C25 Si1 121.12(17) . . ? C26 C25 Si1 121.16(17) . . ? C27 C26 C25 121.2(3) . . ? C28 C27 C26 120.4(3) . . ? C29 C28 C27 119.6(3) . . ? C28 C29 C30 120.8(3) . . ? C25 C30 C29 120.3(3) . . ? 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 C31 N1 C1 C2 -105.9(2) . . . . ? C32 N1 C1 C2 24.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.636 _refine_diff_density_min -0.747 _refine_diff_density_rms 0.074