# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ah0134 _database_code_depnum_ccdc_archive 'CCDC 620201' #TrackingRef 'AH0134.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H44 N O2 Si +, Cl -' _chemical_formula_sum 'C33 H44 Cl N O2 Si' _chemical_formula_weight 550.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.7549(6) _cell_length_b 13.7175(9) _cell_length_c 20.1662(13) _cell_angle_alpha 84.294(3) _cell_angle_beta 75.250(4) _cell_angle_gamma 89.894(4) _cell_volume 3128.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 240098 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.168 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.189 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.867 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ? _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 26871 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0605 _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 -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 24.97 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.978 _reflns_number_total 10742 _reflns_number_gt 7651 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0471P)^2^+5.4705P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10742 _refine_ls_number_parameters 699 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1063 _refine_ls_R_factor_gt 0.0729 _refine_ls_wR_factor_ref 0.1828 _refine_ls_wR_factor_gt 0.1677 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.512 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.059 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 Cl1 Cl 0.64898(9) 0.50985(7) 0.58598(5) 0.0437(3) Uani 1 1 d . . . Cl2 Cl 0.85144(9) 1.03434(7) 0.41896(5) 0.0435(3) Uani 1 1 d . . . N1_1 N 0.7010(3) 0.3773(2) 0.47484(17) 0.0326(7) Uani 1 1 d D . . H1N_1 H 0.695(4) 0.420(3) 0.5066(18) 0.053(13) Uiso 1 1 d D . . C2_1 C 0.6163(3) 0.4012(3) 0.4326(2) 0.0433(10) Uani 1 1 d . . . H2A_1 H 0.6238 0.4719 0.4162 0.052 Uiso 1 1 calc R . . H2B_1 H 0.5353 0.3879 0.4617 0.052 Uiso 1 1 calc R . . C3_1 C 0.6358(3) 0.3430(4) 0.3712(2) 0.0504(11) Uani 1 1 d . . . H3A_1 H 0.5827 0.3661 0.3422 0.060 Uiso 1 1 calc R . . H3B_1 H 0.6166 0.2729 0.3873 0.060 Uiso 1 1 calc R . . C4_1 C 0.7629(3) 0.3537(4) 0.3285(2) 0.0493(11) Uani 1 1 d . . . H4A_1 H 0.7810 0.4230 0.3098 0.059 Uiso 1 1 calc R . . H4B_1 H 0.7747 0.3134 0.2894 0.059 Uiso 1 1 calc R . . C5_1 C 0.8450(3) 0.3205(3) 0.3738(2) 0.0386(9) Uani 1 1 d . . . H5A_1 H 0.8303 0.2498 0.3891 0.046 Uiso 1 1 calc R . . H5B_1 H 0.9274 0.3291 0.3458 0.046 Uiso 1 1 calc R . . C6_1 C 0.8301(3) 0.3761(3) 0.43686(19) 0.0327(8) Uani 1 1 d . . . C7_1 C 0.8736(3) 0.3210(3) 0.49427(19) 0.0332(8) Uani 1 1 d . . . H7A_1 H 0.8799 0.3647 0.5295 0.040 Uiso 1 1 calc R . . H7B_1 H 0.9515 0.2927 0.4759 0.040 Uiso 1 1 calc R . . C8_1 C 0.7799(3) 0.2400(3) 0.5248(2) 0.0356(9) Uani 1 1 d . . . H8A_1 H 0.8010 0.1812 0.4989 0.043 Uiso 1 1 calc R . . O9_1 O 0.6712(2) 0.28088(18) 0.51102(14) 0.0388(6) Uani 1 1 d . . . C10_1 C 0.7650(3) 0.2100(3) 0.6001(2) 0.0364(9) Uani 1 1 d . . . C11_1 C 0.8457(4) 0.1424(3) 0.6175(2) 0.0485(11) Uani 1 1 d . . . H11A_1 H 0.9029 0.1155 0.5823 0.058 Uiso 1 1 calc R . . C12_1 C 0.8416(4) 0.1158(3) 0.6853(3) 0.0566(12) Uani 1 1 d . . . H12A_1 H 0.8971 0.0710 0.6968 0.068 Uiso 1 1 calc R . . C13_1 C 0.7581(4) 0.1528(4) 0.7374(2) 0.0574(12) Uani 1 1 d . . . H13A_1 H 0.7549 0.1329 0.7843 0.069 Uiso 1 1 calc R . . C14_1 C 0.6791(4) 0.2195(3) 0.7202(2) 0.0526(12) Uani 1 1 d . . . H14A_1 H 0.6217 0.2460 0.7556 0.063 Uiso 1 1 calc R . . C15_1 C 0.6828(4) 0.2477(3) 0.6521(2) 0.0437(10) Uani 1 1 d . . . H15A_1 H 0.6281 0.2936 0.6410 0.052 Uiso 1 1 calc R . . C16_1 C 0.8757(3) 0.4823(3) 0.4192(2) 0.0328(8) Uani 1 1 d . . . H16A_1 H 0.8489 0.5180 0.4605 0.039 Uiso 1 1 calc R . . H16B_1 H 0.8414 0.5140 0.3827 0.039 Uiso 1 1 calc R . . C17_1 C 1.0105(3) 0.4908(3) 0.3944(2) 0.0345(9) Uani 1 1 d . . . H17A_1 H 1.0439 0.4819 0.4349 0.041 Uiso 1 1 calc R . . H17B_1 H 1.0394 0.4374 0.3653 0.041 Uiso 1 1 calc R . . C18_1 C 1.0542(3) 0.5885(3) 0.3536(2) 0.0394(9) Uani 1 1 d . . . H18A_1 H 1.0187 0.6420 0.3810 0.047 Uiso 1 1 calc R . . H18B_1 H 1.1406 0.5939 0.3462 0.047 Uiso 1 1 calc R . . C19_1 C 1.0253(4) 0.6021(3) 0.2846(2) 0.0442(10) Uani 1 1 d . . . H19A_1 H 0.9390 0.6062 0.2917 0.053 Uiso 1 1 calc R . . H19B_1 H 1.0616 0.6644 0.2590 0.053 Uiso 1 1 calc R . . O20_1 O 1.0675(2) 0.52241(19) 0.24449(14) 0.0424(7) Uani 1 1 d . . . Si21_1 Si 1.14417(10) 0.53472(8) 0.16369(6) 0.0406(3) Uani 1 1 d . . . C22_1 C 1.1184(4) 0.4173(3) 0.1275(2) 0.0537(12) Uani 1 1 d . . . C23_1 C 0.9879(4) 0.3924(4) 0.1374(3) 0.0789(17) Uani 1 1 d . . . H23A_1 H 0.9796 0.3268 0.1236 0.118 Uiso 1 1 calc R . . H23B_1 H 0.9543 0.4406 0.1090 0.118 Uiso 1 1 calc R . . H23C_1 H 0.9462 0.3938 0.1860 0.118 Uiso 1 1 calc R . . C24_1 C 1.1695(6) 0.3337(4) 0.1674(4) 0.098(2) Uani 1 1 d . . . H24A_1 H 1.1556 0.2711 0.1509 0.147 Uiso 1 1 calc R . . H24B_1 H 1.1309 0.3318 0.2167 0.147 Uiso 1 1 calc R . . H24C_1 H 1.2542 0.3453 0.1599 0.147 Uiso 1 1 calc R . . C25_1 C 1.1814(6) 0.4212(5) 0.0515(3) 0.112(3) Uani 1 1 d . . . H25A_1 H 1.1686 0.3589 0.0342 0.168 Uiso 1 1 calc R . . H25B_1 H 1.2659 0.4326 0.0454 0.168 Uiso 1 1 calc R . . H25C_1 H 1.1505 0.4747 0.0257 0.168 Uiso 1 1 calc R . . C26_1 C 1.3043(4) 0.5479(3) 0.1616(2) 0.0452(10) Uani 1 1 d . . . C27_1 C 1.3886(4) 0.5780(4) 0.1010(3) 0.0644(14) Uani 1 1 d . . . H27A_1 H 1.3654 0.5951 0.0596 0.077 Uiso 1 1 calc R . . C28_1 C 1.5078(5) 0.5833(4) 0.1007(3) 0.0794(17) Uani 1 1 d . . . H28A_1 H 1.5653 0.6037 0.0592 0.095 Uiso 1 1 calc R . . C29_1 C 1.5414(5) 0.5587(4) 0.1608(3) 0.0719(16) Uani 1 1 d . . . H29A_1 H 1.6221 0.5632 0.1605 0.086 Uiso 1 1 calc R . . C30_1 C 1.4598(4) 0.5280(4) 0.2207(3) 0.0617(13) Uani 1 1 d . . . H30A_1 H 1.4837 0.5101 0.2617 0.074 Uiso 1 1 calc R . . C31_1 C 1.3418(4) 0.5232(3) 0.2210(2) 0.0485(11) Uani 1 1 d . . . H31A_1 H 1.2852 0.5026 0.2628 0.058 Uiso 1 1 calc R . . C32_1 C 1.0966(4) 0.6489(3) 0.1208(2) 0.0444(10) Uani 1 1 d . . . C33_1 C 0.9917(5) 0.6549(4) 0.1004(3) 0.0684(14) Uani 1 1 d . . . H33A_1 H 0.9485 0.5962 0.1011 0.082 Uiso 1 1 calc R . . C34_1 C 0.9481(5) 0.7430(4) 0.0793(3) 0.0766(16) Uani 1 1 d . . . H34A_1 H 0.8765 0.7438 0.0657 0.092 Uiso 1 1 calc R . . C35_1 C 1.0074(5) 0.8289(4) 0.0779(3) 0.0630(13) Uani 1 1 d . . . H35A_1 H 0.9772 0.8894 0.0635 0.076 Uiso 1 1 calc R . . C36_1 C 1.1105(4) 0.8275(4) 0.0975(3) 0.0620(13) Uani 1 1 d . . . H36A_1 H 1.1519 0.8871 0.0969 0.074 Uiso 1 1 calc R . . C37_1 C 1.1547(4) 0.7390(3) 0.1181(2) 0.0540(12) Uani 1 1 d . . . H37A_1 H 1.2271 0.7394 0.1308 0.065 Uiso 1 1 calc R . . N1_2 N 0.7976(3) 0.8655(2) 0.52735(17) 0.0339(7) Uani 1 1 d D . . H1N_2 H 0.808(4) 0.918(2) 0.4953(19) 0.061(14) Uiso 1 1 d D . . C2_2 C 0.8824(3) 0.8744(3) 0.5701(2) 0.0423(10) Uani 1 1 d . . . H2C_2 H 0.8745 0.9393 0.5882 0.051 Uiso 1 1 calc R . . H2D_2 H 0.9635 0.8705 0.5409 0.051 Uiso 1 1 calc R . . C3_2 C 0.8623(3) 0.7951(4) 0.6297(2) 0.0499(11) Uani 1 1 d . . . H3C_2 H 0.9155 0.8070 0.6592 0.060 Uiso 1 1 calc R . . H3D_2 H 0.8811 0.7307 0.6118 0.060 Uiso 1 1 calc R . . C4_2 C 0.7361(4) 0.7929(3) 0.6722(2) 0.0468(10) Uani 1 1 d . . . H4C_2 H 0.7186 0.8556 0.6928 0.056 Uiso 1 1 calc R . . H4D_2 H 0.7242 0.7393 0.7102 0.056 Uiso 1 1 calc R . . C5_2 C 0.6525(3) 0.7771(3) 0.6269(2) 0.0378(9) Uani 1 1 d . . . H5C_2 H 0.6653 0.7114 0.6105 0.045 Uiso 1 1 calc R . . H5D_2 H 0.5704 0.7784 0.6553 0.045 Uiso 1 1 calc R . . C6_2 C 0.6685(3) 0.8533(3) 0.56509(19) 0.0313(8) Uani 1 1 d . . . C7_2 C 0.6251(3) 0.8176(3) 0.5064(2) 0.0337(9) Uani 1 1 d . . . H7C_2 H 0.6188 0.8730 0.4721 0.040 Uiso 1 1 calc R . . H7D_2 H 0.5472 0.7840 0.5240 0.040 Uiso 1 1 calc R . . C8_2 C 0.7189(3) 0.7461(3) 0.4743(2) 0.0362(9) Uani 1 1 d . . . H8B_2 H 0.6974 0.6788 0.4982 0.043 Uiso 1 1 calc R . . O9_2 O 0.8274(2) 0.78065(18) 0.48953(14) 0.0386(6) Uani 1 1 d . . . C10_2 C 0.7344(3) 0.7436(3) 0.3983(2) 0.0384(9) Uani 1 1 d . . . C11_2 C 0.6532(4) 0.6865(3) 0.3778(2) 0.0484(11) Uani 1 1 d . . . H11B_2 H 0.5947 0.6484 0.4116 0.058 Uiso 1 1 calc R . . C12_2 C 0.6574(4) 0.6853(4) 0.3089(3) 0.0609(13) Uani 1 1 d . . . H12B_2 H 0.6019 0.6465 0.2955 0.073 Uiso 1 1 calc R . . C13_2 C 0.7424(5) 0.7404(4) 0.2595(3) 0.0623(13) Uani 1 1 d . . . H13B_2 H 0.7454 0.7394 0.2120 0.075 Uiso 1 1 calc R . . C14_2 C 0.8229(4) 0.7970(3) 0.2790(2) 0.0562(12) Uani 1 1 d . . . H14B_2 H 0.8811 0.8353 0.2451 0.067 Uiso 1 1 calc R . . C15_2 C 0.8188(4) 0.7979(3) 0.3482(2) 0.0436(10) Uani 1 1 d . . . H15B_2 H 0.8749 0.8365 0.3613 0.052 Uiso 1 1 calc R . . C16_2 C 0.6221(3) 0.9544(3) 0.5843(2) 0.0343(9) Uani 1 1 d . . . H16C_2 H 0.6529 0.9727 0.6228 0.041 Uiso 1 1 calc R . . H16D_2 H 0.6520 1.0038 0.5444 0.041 Uiso 1 1 calc R . . C17_2 C 0.4877(3) 0.9562(3) 0.6055(2) 0.0341(9) Uani 1 1 d . . . H17C_2 H 0.4583 0.9626 0.5634 0.041 Uiso 1 1 calc R . . H17D_2 H 0.4569 0.8932 0.6322 0.041 Uiso 1 1 calc R . . C18_2 C 0.4406(3) 1.0396(3) 0.6484(2) 0.0402(9) Uani 1 1 d . . . H18C_2 H 0.4770 1.1020 0.6232 0.048 Uiso 1 1 calc R . . H18D_2 H 0.3546 1.0431 0.6537 0.048 Uiso 1 1 calc R . . C19_2 C 0.4636(4) 1.0291(3) 0.7192(2) 0.0439(10) Uani 1 1 d . . . H19C_2 H 0.5486 1.0400 0.7146 0.053 Uiso 1 1 calc R . . H19D_2 H 0.4201 1.0796 0.7467 0.053 Uiso 1 1 calc R . . O20_2 O 0.4277(2) 0.9335(2) 0.75459(14) 0.0427(7) Uani 1 1 d . . . Si21_2 Si 0.34763(10) 0.91108(9) 0.83391(6) 0.0395(3) Uani 1 1 d . . . C22_2 C 0.3822(4) 0.7824(3) 0.8623(2) 0.0479(11) Uani 1 1 d . . . C23_2 C 0.5144(4) 0.7697(4) 0.8572(3) 0.0691(15) Uani 1 1 d . . . H23D_2 H 0.5285 0.7014 0.8717 0.104 Uiso 1 1 calc R . . H23E_2 H 0.5392 0.8128 0.8872 0.104 Uiso 1 1 calc R . . H23F_2 H 0.5596 0.7869 0.8095 0.104 Uiso 1 1 calc R . . C24_2 C 0.3470(5) 0.7131(4) 0.8138(3) 0.0650(14) Uani 1 1 d . . . H24D_2 H 0.3666 0.6456 0.8267 0.098 Uiso 1 1 calc R . . H24E_2 H 0.3899 0.7334 0.7660 0.098 Uiso 1 1 calc R . . H24F_2 H 0.2622 0.7167 0.8180 0.098 Uiso 1 1 calc R . . C25_2 C 0.3126(4) 0.7495(4) 0.9365(2) 0.0626(13) Uani 1 1 d . . . H25D_2 H 0.3354 0.6832 0.9501 0.094 Uiso 1 1 calc R . . H25E_2 H 0.2282 0.7495 0.9392 0.094 Uiso 1 1 calc R . . H25F_2 H 0.3298 0.7946 0.9676 0.094 Uiso 1 1 calc R . . C26_2 C 0.1879(3) 0.9165(3) 0.8342(2) 0.0403(9) Uani 1 1 d . . . C27_2 C 0.0975(4) 0.9081(3) 0.8947(2) 0.0513(11) Uani 1 1 d . . . H27B_2 H 0.1167 0.8998 0.9379 0.062 Uiso 1 1 calc R . . C28_2 C -0.0204(4) 0.9117(4) 0.8934(3) 0.0591(13) Uani 1 1 d . . . H28B_2 H -0.0804 0.9080 0.9353 0.071 Uiso 1 1 calc R . . C29_2 C -0.0495(4) 0.9207(3) 0.8316(3) 0.0592(13) Uani 1 1 d . . . H29B_2 H -0.1299 0.9223 0.8306 0.071 Uiso 1 1 calc R . . C30_2 C 0.0377(4) 0.9273(3) 0.7704(3) 0.0539(12) Uani 1 1 d . . . H30B_2 H 0.0175 0.9335 0.7275 0.065 Uiso 1 1 calc R . . C31_2 C 0.1547(4) 0.9248(3) 0.7724(2) 0.0453(10) Uani 1 1 d . . . H31B_2 H 0.2141 0.9289 0.7302 0.054 Uiso 1 1 calc R . . C32_2 C 0.3876(4) 1.0043(3) 0.8867(2) 0.0453(10) Uani 1 1 d . . . C33_2 C 0.5041(4) 1.0221(5) 0.8844(3) 0.0777(17) Uani 1 1 d . . . H33B_2 H 0.5627 0.9838 0.8580 0.093 Uiso 1 1 calc R . . C34_2 C 0.5386(5) 1.0944(5) 0.9197(3) 0.0853(19) Uani 1 1 d . . . H34B_2 H 0.6197 1.1057 0.9162 0.102 Uiso 1 1 calc R . . C35_2 C 0.4574(5) 1.1483(4) 0.9585(3) 0.0740(16) Uani 1 1 d . . . H35B_2 H 0.4809 1.1986 0.9817 0.089 Uiso 1 1 calc R . . C36_2 C 0.3411(6) 1.1301(5) 0.9645(4) 0.104(2) Uani 1 1 d . . . H36B_2 H 0.2832 1.1663 0.9933 0.125 Uiso 1 1 calc R . . C37_2 C 0.3068(5) 1.0589(5) 0.9285(3) 0.086(2) Uani 1 1 d . . . H37B_2 H 0.2253 1.0477 0.9329 0.104 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0473(6) 0.0348(5) 0.0503(6) -0.0099(4) -0.0129(5) 0.0063(4) Cl2 0.0464(6) 0.0340(5) 0.0494(6) -0.0034(4) -0.0116(5) -0.0060(4) N1_1 0.0276(16) 0.0267(17) 0.044(2) -0.0043(14) -0.0090(14) -0.0010(13) C2_1 0.028(2) 0.050(3) 0.054(3) -0.001(2) -0.0165(18) -0.0016(17) C3_1 0.037(2) 0.066(3) 0.052(3) -0.007(2) -0.019(2) -0.007(2) C4_1 0.040(2) 0.067(3) 0.043(3) -0.009(2) -0.0139(19) -0.011(2) C5_1 0.035(2) 0.034(2) 0.046(2) -0.0083(18) -0.0073(18) -0.0005(16) C6_1 0.0224(18) 0.034(2) 0.042(2) -0.0020(17) -0.0089(16) -0.0020(15) C7_1 0.0275(19) 0.028(2) 0.044(2) -0.0055(16) -0.0086(16) 0.0004(15) C8_1 0.031(2) 0.026(2) 0.052(2) -0.0053(17) -0.0131(18) 0.0001(15) O9_1 0.0330(14) 0.0308(15) 0.0524(17) -0.0002(12) -0.0119(12) -0.0077(11) C10_1 0.038(2) 0.025(2) 0.046(2) -0.0022(17) -0.0127(18) -0.0096(16) C11_1 0.047(3) 0.041(3) 0.055(3) 0.000(2) -0.012(2) 0.0001(19) C12_1 0.060(3) 0.046(3) 0.067(3) 0.007(2) -0.026(3) 0.000(2) C13_1 0.073(3) 0.051(3) 0.049(3) 0.004(2) -0.021(3) -0.017(2) C14_1 0.061(3) 0.043(3) 0.049(3) -0.008(2) -0.003(2) -0.008(2) C15_1 0.046(2) 0.036(2) 0.046(3) -0.0029(19) -0.006(2) -0.0047(18) C16_1 0.0277(19) 0.027(2) 0.044(2) -0.0025(16) -0.0090(16) -0.0029(15) C17_1 0.0301(19) 0.031(2) 0.044(2) -0.0030(17) -0.0125(17) -0.0035(15) C18_1 0.039(2) 0.036(2) 0.043(2) -0.0049(18) -0.0088(18) -0.0095(17) C19_1 0.052(3) 0.031(2) 0.046(2) -0.0021(18) -0.005(2) -0.0029(18) O20_1 0.0515(17) 0.0313(15) 0.0445(16) -0.0055(12) -0.0119(13) -0.0028(12) Si21_1 0.0409(6) 0.0411(7) 0.0410(7) -0.0051(5) -0.0122(5) -0.0014(5) C22_1 0.051(3) 0.054(3) 0.061(3) -0.022(2) -0.018(2) 0.002(2) C23_1 0.055(3) 0.072(4) 0.119(5) -0.033(3) -0.031(3) -0.009(3) C24_1 0.099(5) 0.051(4) 0.168(7) -0.029(4) -0.071(5) 0.005(3) C25_1 0.122(6) 0.117(6) 0.087(5) -0.065(4) 0.013(4) -0.036(4) C26_1 0.046(2) 0.038(2) 0.053(3) -0.009(2) -0.013(2) -0.0009(18) C27_1 0.052(3) 0.073(4) 0.063(3) 0.011(3) -0.012(2) 0.001(2) C28_1 0.051(3) 0.077(4) 0.096(5) 0.012(3) 0.000(3) -0.005(3) C29_1 0.049(3) 0.060(3) 0.112(5) -0.006(3) -0.031(3) 0.006(2) C30_1 0.055(3) 0.056(3) 0.083(4) -0.016(3) -0.031(3) 0.008(2) C31_1 0.051(3) 0.037(2) 0.062(3) -0.011(2) -0.021(2) 0.0025(19) C32_1 0.042(2) 0.052(3) 0.038(2) -0.0025(19) -0.0105(19) 0.0011(19) C33_1 0.065(3) 0.060(3) 0.090(4) -0.002(3) -0.039(3) -0.003(3) C34_1 0.073(4) 0.074(4) 0.092(4) 0.002(3) -0.044(3) 0.012(3) C35_1 0.069(3) 0.058(3) 0.060(3) 0.004(2) -0.017(3) 0.015(3) C36_1 0.063(3) 0.047(3) 0.075(4) -0.002(2) -0.019(3) 0.007(2) C37_1 0.052(3) 0.044(3) 0.068(3) -0.004(2) -0.020(2) 0.002(2) N1_2 0.0271(16) 0.0276(18) 0.048(2) -0.0075(15) -0.0090(14) 0.0024(13) C2_2 0.025(2) 0.051(3) 0.055(3) -0.012(2) -0.0146(18) 0.0029(17) C3_2 0.037(2) 0.064(3) 0.052(3) -0.004(2) -0.018(2) 0.012(2) C4_2 0.045(2) 0.054(3) 0.043(2) -0.003(2) -0.0150(19) 0.011(2) C5_2 0.033(2) 0.034(2) 0.046(2) -0.0046(17) -0.0077(17) 0.0018(16) C6_2 0.0223(18) 0.031(2) 0.041(2) -0.0072(16) -0.0089(15) 0.0043(14) C7_2 0.0273(19) 0.028(2) 0.045(2) -0.0067(17) -0.0071(16) 0.0004(15) C8_2 0.031(2) 0.026(2) 0.052(2) -0.0072(17) -0.0111(18) 0.0004(15) O9_2 0.0330(14) 0.0339(15) 0.0501(17) -0.0117(12) -0.0101(12) 0.0078(11) C10_2 0.038(2) 0.030(2) 0.047(2) -0.0081(18) -0.0081(18) 0.0086(17) C11_2 0.048(3) 0.041(3) 0.058(3) -0.015(2) -0.013(2) 0.0025(19) C12_2 0.061(3) 0.061(3) 0.070(4) -0.031(3) -0.025(3) 0.008(2) C13_2 0.074(3) 0.069(3) 0.050(3) -0.021(3) -0.022(3) 0.024(3) C14_2 0.062(3) 0.049(3) 0.051(3) -0.007(2) -0.003(2) 0.012(2) C15_2 0.046(2) 0.036(2) 0.046(3) -0.0110(19) -0.0061(19) 0.0044(18) C16_2 0.032(2) 0.027(2) 0.044(2) -0.0093(17) -0.0095(17) 0.0024(15) C17_2 0.0272(19) 0.035(2) 0.042(2) -0.0059(17) -0.0116(16) 0.0026(15) C18_2 0.037(2) 0.034(2) 0.047(2) -0.0053(18) -0.0071(18) 0.0092(17) C19_2 0.051(3) 0.035(2) 0.045(2) -0.0081(18) -0.0087(19) 0.0020(18) O20_2 0.0484(16) 0.0392(16) 0.0407(16) -0.0050(12) -0.0112(13) 0.0011(12) Si21_2 0.0383(6) 0.0445(7) 0.0372(6) -0.0066(5) -0.0117(5) 0.0007(5) C22_2 0.051(3) 0.054(3) 0.042(2) -0.005(2) -0.018(2) 0.007(2) C23_2 0.055(3) 0.083(4) 0.067(3) 0.000(3) -0.014(3) 0.018(3) C24_2 0.083(4) 0.051(3) 0.067(3) -0.008(2) -0.030(3) 0.006(3) C25_2 0.060(3) 0.069(3) 0.053(3) 0.010(2) -0.011(2) 0.012(2) C26_2 0.043(2) 0.033(2) 0.047(2) -0.0035(18) -0.0151(19) -0.0012(17) C27_2 0.049(3) 0.052(3) 0.053(3) -0.006(2) -0.012(2) 0.000(2) C28_2 0.046(3) 0.055(3) 0.071(3) -0.007(2) -0.006(2) -0.001(2) C29_2 0.046(3) 0.048(3) 0.089(4) -0.001(3) -0.029(3) 0.001(2) C30_2 0.051(3) 0.048(3) 0.068(3) 0.002(2) -0.028(2) -0.005(2) C31_2 0.047(2) 0.039(2) 0.052(3) 0.0008(19) -0.018(2) -0.0024(18) C32_2 0.045(2) 0.049(3) 0.043(2) -0.010(2) -0.0135(19) -0.003(2) C33_2 0.048(3) 0.098(5) 0.093(4) -0.043(4) -0.015(3) -0.004(3) C34_2 0.062(4) 0.107(5) 0.093(4) -0.035(4) -0.022(3) -0.029(3) C35_2 0.085(4) 0.075(4) 0.069(4) -0.022(3) -0.026(3) -0.022(3) C36_2 0.080(4) 0.105(5) 0.148(6) -0.083(5) -0.041(4) 0.012(4) C37_2 0.054(3) 0.098(5) 0.126(5) -0.065(4) -0.037(3) 0.013(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1_1 O9_1 1.443(4) . ? N1_1 C2_1 1.483(5) . ? N1_1 C6_1 1.517(4) . ? N1_1 H1N_1 0.898(19) . ? C2_1 C3_1 1.507(6) . ? C2_1 H2A_1 0.9900 . ? C2_1 H2B_1 0.9900 . ? C3_1 C4_1 1.521(6) . ? C3_1 H3A_1 0.9900 . ? C3_1 H3B_1 0.9900 . ? C4_1 C5_1 1.528(6) . ? C4_1 H4A_1 0.9900 . ? C4_1 H4B_1 0.9900 . ? C5_1 C6_1 1.520(5) . ? C5_1 H5A_1 0.9900 . ? C5_1 H5B_1 0.9900 . ? C6_1 C7_1 1.516(5) . ? C6_1 C16_1 1.529(5) . ? C7_1 C8_1 1.534(5) . ? C7_1 H7A_1 0.9900 . ? C7_1 H7B_1 0.9900 . ? C8_1 O9_1 1.473(4) . ? C8_1 C10_1 1.501(5) . ? C8_1 H8A_1 1.0000 . ? C10_1 C15_1 1.375(6) . ? C10_1 C11_1 1.408(6) . ? C11_1 C12_1 1.368(6) . ? C11_1 H11A_1 0.9500 . ? C12_1 C13_1 1.379(7) . ? C12_1 H12A_1 0.9500 . ? C13_1 C14_1 1.385(7) . ? C13_1 H13A_1 0.9500 . ? C14_1 C15_1 1.378(6) . ? C14_1 H14A_1 0.9500 . ? C15_1 H15A_1 0.9500 . ? C16_1 C17_1 1.536(5) . ? C16_1 H16A_1 0.9900 . ? C16_1 H16B_1 0.9900 . ? C17_1 C18_1 1.519(5) . ? C17_1 H17A_1 0.9900 . ? C17_1 H17B_1 0.9900 . ? C18_1 C19_1 1.509(6) . ? C18_1 H18A_1 0.9900 . ? C18_1 H18B_1 0.9900 . ? C19_1 O20_1 1.437(5) . ? C19_1 H19A_1 0.9900 . ? C19_1 H19B_1 0.9900 . ? O20_1 Si21_1 1.641(3) . ? Si21_1 C32_1 1.868(4) . ? Si21_1 C26_1 1.880(4) . ? Si21_1 C22_1 1.889(4) . ? C22_1 C25_1 1.519(7) . ? C22_1 C23_1 1.530(6) . ? C22_1 C24_1 1.544(8) . ? C23_1 H23A_1 0.9800 . ? C23_1 H23B_1 0.9800 . ? C23_1 H23C_1 0.9800 . ? C24_1 H24A_1 0.9800 . ? C24_1 H24B_1 0.9800 . ? C24_1 H24C_1 0.9800 . ? C25_1 H25A_1 0.9800 . ? C25_1 H25B_1 0.9800 . ? C25_1 H25C_1 0.9800 . ? C26_1 C27_1 1.389(6) . ? C26_1 C31_1 1.390(6) . ? C27_1 C28_1 1.401(7) . ? C27_1 H27A_1 0.9500 . ? C28_1 C29_1 1.378(8) . ? C28_1 H28A_1 0.9500 . ? C29_1 C30_1 1.366(7) . ? C29_1 H29A_1 0.9500 . ? C30_1 C31_1 1.387(6) . ? C30_1 H30A_1 0.9500 . ? C31_1 H31A_1 0.9500 . ? C32_1 C33_1 1.396(6) . ? C32_1 C37_1 1.402(6) . ? C33_1 C34_1 1.382(7) . ? C33_1 H33A_1 0.9500 . ? C34_1 C35_1 1.364(7) . ? C34_1 H34A_1 0.9500 . ? C35_1 C36_1 1.366(7) . ? C35_1 H35A_1 0.9500 . ? C36_1 C37_1 1.387(6) . ? C36_1 H36A_1 0.9500 . ? C37_1 H37A_1 0.9500 . ? N1_2 O9_2 1.449(4) . ? N1_2 C2_2 1.487(5) . ? N1_2 C6_2 1.516(4) . ? N1_2 H1N_2 0.902(19) . ? C2_2 C3_2 1.510(6) . ? C2_2 H2C_2 0.9900 . ? C2_2 H2D_2 0.9900 . ? C3_2 C4_2 1.512(6) . ? C3_2 H3C_2 0.9900 . ? C3_2 H3D_2 0.9900 . ? C4_2 C5_2 1.531(6) . ? C4_2 H4C_2 0.9900 . ? C4_2 H4D_2 0.9900 . ? C5_2 C6_2 1.519(5) . ? C5_2 H5C_2 0.9900 . ? C5_2 H5D_2 0.9900 . ? C6_2 C7_2 1.526(5) . ? C6_2 C16_2 1.538(5) . ? C7_2 C8_2 1.535(5) . ? C7_2 H7C_2 0.9900 . ? C7_2 H7D_2 0.9900 . ? C8_2 O9_2 1.474(4) . ? C8_2 C10_2 1.501(6) . ? C8_2 H8B_2 1.0000 . ? C10_2 C15_2 1.380(6) . ? C10_2 C11_2 1.401(6) . ? C11_2 C12_2 1.379(6) . ? C11_2 H11B_2 0.9500 . ? C12_2 C13_2 1.382(7) . ? C12_2 H12B_2 0.9500 . ? C13_2 C14_2 1.382(7) . ? C13_2 H13B_2 0.9500 . ? C14_2 C15_2 1.384(6) . ? C14_2 H14B_2 0.9500 . ? C15_2 H15B_2 0.9500 . ? C16_2 C17_2 1.529(5) . ? C16_2 H16C_2 0.9900 . ? C16_2 H16D_2 0.9900 . ? C17_2 C18_2 1.521(5) . ? C17_2 H17C_2 0.9900 . ? C17_2 H17D_2 0.9900 . ? C18_2 C19_2 1.513(6) . ? C18_2 H18C_2 0.9900 . ? C18_2 H18D_2 0.9900 . ? C19_2 O20_2 1.438(5) . ? C19_2 H19C_2 0.9900 . ? C19_2 H19D_2 0.9900 . ? O20_2 Si21_2 1.636(3) . ? Si21_2 C32_2 1.876(4) . ? Si21_2 C22_2 1.877(5) . ? Si21_2 C26_2 1.877(4) . ? C22_2 C25_2 1.534(6) . ? C22_2 C23_2 1.542(6) . ? C22_2 C24_2 1.559(6) . ? C23_2 H23D_2 0.9800 . ? C23_2 H23E_2 0.9800 . ? C23_2 H23F_2 0.9800 . ? C24_2 H24D_2 0.9800 . ? C24_2 H24E_2 0.9800 . ? C24_2 H24F_2 0.9800 . ? C25_2 H25D_2 0.9800 . ? C25_2 H25E_2 0.9800 . ? C25_2 H25F_2 0.9800 . ? C26_2 C31_2 1.393(6) . ? C26_2 C27_2 1.395(6) . ? C27_2 C28_2 1.393(6) . ? C27_2 H27B_2 0.9500 . ? C28_2 C29_2 1.369(7) . ? C28_2 H28B_2 0.9500 . ? C29_2 C30_2 1.383(7) . ? C29_2 H29B_2 0.9500 . ? C30_2 C31_2 1.386(6) . ? C30_2 H30B_2 0.9500 . ? C31_2 H31B_2 0.9500 . ? C32_2 C37_2 1.373(7) . ? C32_2 C33_2 1.380(6) . ? C33_2 C34_2 1.394(7) . ? C33_2 H33B_2 0.9500 . ? C34_2 C35_2 1.342(8) . ? C34_2 H34B_2 0.9500 . ? C35_2 C36_2 1.363(8) . ? C35_2 H35B_2 0.9500 . ? C36_2 C37_2 1.392(7) . ? C36_2 H36B_2 0.9500 . ? C37_2 H37B_2 0.9500 . ? 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 O9_1 N1_1 C2_1 108.5(3) . . ? O9_1 N1_1 C6_1 106.5(3) . . ? C2_1 N1_1 C6_1 117.0(3) . . ? O9_1 N1_1 H1N_1 108(3) . . ? C2_1 N1_1 H1N_1 111(3) . . ? C6_1 N1_1 H1N_1 106(3) . . ? N1_1 C2_1 C3_1 112.5(3) . . ? N1_1 C2_1 H2A_1 109.1 . . ? C3_1 C2_1 H2A_1 109.1 . . ? N1_1 C2_1 H2B_1 109.1 . . ? C3_1 C2_1 H2B_1 109.1 . . ? H2A_1 C2_1 H2B_1 107.8 . . ? C2_1 C3_1 C4_1 110.9(3) . . ? C2_1 C3_1 H3A_1 109.5 . . ? C4_1 C3_1 H3A_1 109.5 . . ? C2_1 C3_1 H3B_1 109.5 . . ? C4_1 C3_1 H3B_1 109.5 . . ? H3A_1 C3_1 H3B_1 108.1 . . ? C3_1 C4_1 C5_1 109.5(3) . . ? C3_1 C4_1 H4A_1 109.8 . . ? C5_1 C4_1 H4A_1 109.8 . . ? C3_1 C4_1 H4B_1 109.8 . . ? C5_1 C4_1 H4B_1 109.8 . . ? H4A_1 C4_1 H4B_1 108.2 . . ? C6_1 C5_1 C4_1 113.6(3) . . ? C6_1 C5_1 H5A_1 108.8 . . ? C4_1 C5_1 H5A_1 108.8 . . ? C6_1 C5_1 H5B_1 108.8 . . ? C4_1 C5_1 H5B_1 108.8 . . ? H5A_1 C5_1 H5B_1 107.7 . . ? C7_1 C6_1 N1_1 97.6(3) . . ? C7_1 C6_1 C5_1 113.4(3) . . ? N1_1 C6_1 C5_1 109.9(3) . . ? C7_1 C6_1 C16_1 113.7(3) . . ? N1_1 C6_1 C16_1 107.9(3) . . ? C5_1 C6_1 C16_1 113.1(3) . . ? C6_1 C7_1 C8_1 104.2(3) . . ? C6_1 C7_1 H7A_1 110.9 . . ? C8_1 C7_1 H7A_1 110.9 . . ? C6_1 C7_1 H7B_1 110.9 . . ? C8_1 C7_1 H7B_1 110.9 . . ? H7A_1 C7_1 H7B_1 108.9 . . ? O9_1 C8_1 C10_1 111.6(3) . . ? O9_1 C8_1 C7_1 104.3(3) . . ? C10_1 C8_1 C7_1 114.1(3) . . ? O9_1 C8_1 H8A_1 108.9 . . ? C10_1 C8_1 H8A_1 108.9 . . ? C7_1 C8_1 H8A_1 108.9 . . ? N1_1 O9_1 C8_1 107.2(2) . . ? C15_1 C10_1 C11_1 119.0(4) . . ? C15_1 C10_1 C8_1 124.4(4) . . ? C11_1 C10_1 C8_1 116.6(4) . . ? C12_1 C11_1 C10_1 119.8(4) . . ? C12_1 C11_1 H11A_1 120.1 . . ? C10_1 C11_1 H11A_1 120.1 . . ? C11_1 C12_1 C13_1 121.1(5) . . ? C11_1 C12_1 H12A_1 119.5 . . ? C13_1 C12_1 H12A_1 119.5 . . ? C12_1 C13_1 C14_1 119.0(4) . . ? C12_1 C13_1 H13A_1 120.5 . . ? C14_1 C13_1 H13A_1 120.5 . . ? C15_1 C14_1 C13_1 120.6(4) . . ? C15_1 C14_1 H14A_1 119.7 . . ? C13_1 C14_1 H14A_1 119.7 . . ? C10_1 C15_1 C14_1 120.5(4) . . ? C10_1 C15_1 H15A_1 119.7 . . ? C14_1 C15_1 H15A_1 119.7 . . ? C6_1 C16_1 C17_1 112.9(3) . . ? C6_1 C16_1 H16A_1 109.0 . . ? C17_1 C16_1 H16A_1 109.0 . . ? C6_1 C16_1 H16B_1 109.0 . . ? C17_1 C16_1 H16B_1 109.0 . . ? H16A_1 C16_1 H16B_1 107.8 . . ? C18_1 C17_1 C16_1 113.0(3) . . ? C18_1 C17_1 H17A_1 109.0 . . ? C16_1 C17_1 H17A_1 109.0 . . ? C18_1 C17_1 H17B_1 109.0 . . ? C16_1 C17_1 H17B_1 109.0 . . ? H17A_1 C17_1 H17B_1 107.8 . . ? C19_1 C18_1 C17_1 113.4(3) . . ? C19_1 C18_1 H18A_1 108.9 . . ? C17_1 C18_1 H18A_1 108.9 . . ? C19_1 C18_1 H18B_1 108.9 . . ? C17_1 C18_1 H18B_1 108.9 . . ? H18A_1 C18_1 H18B_1 107.7 . . ? O20_1 C19_1 C18_1 111.2(3) . . ? O20_1 C19_1 H19A_1 109.4 . . ? C18_1 C19_1 H19A_1 109.4 . . ? O20_1 C19_1 H19B_1 109.4 . . ? C18_1 C19_1 H19B_1 109.4 . . ? H19A_1 C19_1 H19B_1 108.0 . . ? C19_1 O20_1 Si21_1 124.9(2) . . ? O20_1 Si21_1 C32_1 107.82(17) . . ? O20_1 Si21_1 C26_1 108.45(18) . . ? C32_1 Si21_1 C26_1 109.24(19) . . ? O20_1 Si21_1 C22_1 105.90(18) . . ? C32_1 Si21_1 C22_1 115.6(2) . . ? C26_1 Si21_1 C22_1 109.56(19) . . ? C25_1 C22_1 C23_1 109.4(5) . . ? C25_1 C22_1 C24_1 108.8(5) . . ? C23_1 C22_1 C24_1 107.2(4) . . ? C25_1 C22_1 Si21_1 111.0(4) . . ? C23_1 C22_1 Si21_1 113.2(3) . . ? C24_1 C22_1 Si21_1 107.0(3) . . ? C22_1 C23_1 H23A_1 109.5 . . ? C22_1 C23_1 H23B_1 109.5 . . ? H23A_1 C23_1 H23B_1 109.5 . . ? C22_1 C23_1 H23C_1 109.5 . . ? H23A_1 C23_1 H23C_1 109.5 . . ? H23B_1 C23_1 H23C_1 109.5 . . ? C22_1 C24_1 H24A_1 109.5 . . ? C22_1 C24_1 H24B_1 109.5 . . ? H24A_1 C24_1 H24B_1 109.5 . . ? C22_1 C24_1 H24C_1 109.5 . . ? H24A_1 C24_1 H24C_1 109.5 . . ? H24B_1 C24_1 H24C_1 109.5 . . ? C22_1 C25_1 H25A_1 109.5 . . ? C22_1 C25_1 H25B_1 109.5 . . ? H25A_1 C25_1 H25B_1 109.5 . . ? C22_1 C25_1 H25C_1 109.5 . . ? H25A_1 C25_1 H25C_1 109.5 . . ? H25B_1 C25_1 H25C_1 109.5 . . ? C27_1 C26_1 C31_1 118.1(4) . . ? C27_1 C26_1 Si21_1 121.8(4) . . ? C31_1 C26_1 Si21_1 120.1(3) . . ? C26_1 C27_1 C28_1 120.3(5) . . ? C26_1 C27_1 H27A_1 119.8 . . ? C28_1 C27_1 H27A_1 119.8 . . ? C29_1 C28_1 C27_1 119.8(5) . . ? C29_1 C28_1 H28A_1 120.1 . . ? C27_1 C28_1 H28A_1 120.1 . . ? C30_1 C29_1 C28_1 120.7(5) . . ? C30_1 C29_1 H29A_1 119.6 . . ? C28_1 C29_1 H29A_1 119.6 . . ? C29_1 C30_1 C31_1 119.4(5) . . ? C29_1 C30_1 H30A_1 120.3 . . ? C31_1 C30_1 H30A_1 120.3 . . ? C30_1 C31_1 C26_1 121.7(5) . . ? C30_1 C31_1 H31A_1 119.2 . . ? C26_1 C31_1 H31A_1 119.2 . . ? C33_1 C32_1 C37_1 115.0(4) . . ? C33_1 C32_1 Si21_1 123.2(4) . . ? C37_1 C32_1 Si21_1 120.9(3) . . ? C34_1 C33_1 C32_1 122.5(5) . . ? C34_1 C33_1 H33A_1 118.7 . . ? C32_1 C33_1 H33A_1 118.7 . . ? C35_1 C34_1 C33_1 120.4(5) . . ? C35_1 C34_1 H34A_1 119.8 . . ? C33_1 C34_1 H34A_1 119.8 . . ? C34_1 C35_1 C36_1 119.6(5) . . ? C34_1 C35_1 H35A_1 120.2 . . ? C36_1 C35_1 H35A_1 120.2 . . ? C35_1 C36_1 C37_1 120.0(5) . . ? C35_1 C36_1 H36A_1 120.0 . . ? C37_1 C36_1 H36A_1 120.0 . . ? C36_1 C37_1 C32_1 122.5(4) . . ? C36_1 C37_1 H37A_1 118.7 . . ? C32_1 C37_1 H37A_1 118.7 . . ? O9_2 N1_2 C2_2 108.3(3) . . ? O9_2 N1_2 C6_2 106.6(2) . . ? C2_2 N1_2 C6_2 117.0(3) . . ? O9_2 N1_2 H1N_2 106(3) . . ? C2_2 N1_2 H1N_2 109(3) . . ? C6_2 N1_2 H1N_2 110(3) . . ? N1_2 C2_2 C3_2 112.0(3) . . ? N1_2 C2_2 H2C_2 109.2 . . ? C3_2 C2_2 H2C_2 109.2 . . ? N1_2 C2_2 H2D_2 109.2 . . ? C3_2 C2_2 H2D_2 109.2 . . ? H2C_2 C2_2 H2D_2 107.9 . . ? C2_2 C3_2 C4_2 110.9(3) . . ? C2_2 C3_2 H3C_2 109.5 . . ? C4_2 C3_2 H3C_2 109.5 . . ? C2_2 C3_2 H3D_2 109.5 . . ? C4_2 C3_2 H3D_2 109.5 . . ? H3C_2 C3_2 H3D_2 108.0 . . ? C3_2 C4_2 C5_2 110.1(3) . . ? C3_2 C4_2 H4C_2 109.6 . . ? C5_2 C4_2 H4C_2 109.6 . . ? C3_2 C4_2 H4D_2 109.6 . . ? C5_2 C4_2 H4D_2 109.6 . . ? H4C_2 C4_2 H4D_2 108.2 . . ? C6_2 C5_2 C4_2 113.5(3) . . ? C6_2 C5_2 H5C_2 108.9 . . ? C4_2 C5_2 H5C_2 108.9 . . ? C6_2 C5_2 H5D_2 108.9 . . ? C4_2 C5_2 H5D_2 108.9 . . ? H5C_2 C5_2 H5D_2 107.7 . . ? N1_2 C6_2 C5_2 110.2(3) . . ? N1_2 C6_2 C7_2 97.4(3) . . ? C5_2 C6_2 C7_2 113.2(3) . . ? N1_2 C6_2 C16_2 108.2(3) . . ? C5_2 C6_2 C16_2 113.3(3) . . ? C7_2 C6_2 C16_2 113.3(3) . . ? C6_2 C7_2 C8_2 104.3(3) . . ? C6_2 C7_2 H7C_2 110.9 . . ? C8_2 C7_2 H7C_2 110.9 . . ? C6_2 C7_2 H7D_2 110.9 . . ? C8_2 C7_2 H7D_2 110.9 . . ? H7C_2 C7_2 H7D_2 108.9 . . ? O9_2 C8_2 C10_2 111.5(3) . . ? O9_2 C8_2 C7_2 104.3(3) . . ? C10_2 C8_2 C7_2 113.4(3) . . ? O9_2 C8_2 H8B_2 109.2 . . ? C10_2 C8_2 H8B_2 109.2 . . ? C7_2 C8_2 H8B_2 109.2 . . ? N1_2 O9_2 C8_2 107.2(2) . . ? C15_2 C10_2 C11_2 118.6(4) . . ? C15_2 C10_2 C8_2 124.1(4) . . ? C11_2 C10_2 C8_2 117.2(4) . . ? C12_2 C11_2 C10_2 120.5(4) . . ? C12_2 C11_2 H11B_2 119.7 . . ? C10_2 C11_2 H11B_2 119.7 . . ? C11_2 C12_2 C13_2 120.0(5) . . ? C11_2 C12_2 H12B_2 120.0 . . ? C13_2 C12_2 H12B_2 120.0 . . ? C14_2 C13_2 C12_2 120.0(5) . . ? C14_2 C13_2 H13B_2 120.0 . . ? C12_2 C13_2 H13B_2 120.0 . . ? C13_2 C14_2 C15_2 119.9(5) . . ? C13_2 C14_2 H14B_2 120.1 . . ? C15_2 C14_2 H14B_2 120.1 . . ? C10_2 C15_2 C14_2 121.0(4) . . ? C10_2 C15_2 H15B_2 119.5 . . ? C14_2 C15_2 H15B_2 119.5 . . ? C17_2 C16_2 C6_2 112.6(3) . . ? C17_2 C16_2 H16C_2 109.1 . . ? C6_2 C16_2 H16C_2 109.1 . . ? C17_2 C16_2 H16D_2 109.1 . . ? C6_2 C16_2 H16D_2 109.1 . . ? H16C_2 C16_2 H16D_2 107.8 . . ? C18_2 C17_2 C16_2 113.1(3) . . ? C18_2 C17_2 H17C_2 109.0 . . ? C16_2 C17_2 H17C_2 109.0 . . ? C18_2 C17_2 H17D_2 109.0 . . ? C16_2 C17_2 H17D_2 109.0 . . ? H17C_2 C17_2 H17D_2 107.8 . . ? C19_2 C18_2 C17_2 113.9(3) . . ? C19_2 C18_2 H18C_2 108.8 . . ? C17_2 C18_2 H18C_2 108.8 . . ? C19_2 C18_2 H18D_2 108.8 . . ? C17_2 C18_2 H18D_2 108.8 . . ? H18C_2 C18_2 H18D_2 107.7 . . ? O20_2 C19_2 C18_2 111.3(3) . . ? O20_2 C19_2 H19C_2 109.4 . . ? C18_2 C19_2 H19C_2 109.4 . . ? O20_2 C19_2 H19D_2 109.4 . . ? C18_2 C19_2 H19D_2 109.4 . . ? H19C_2 C19_2 H19D_2 108.0 . . ? C19_2 O20_2 Si21_2 125.7(2) . . ? O20_2 Si21_2 C32_2 108.47(17) . . ? O20_2 Si21_2 C22_2 105.32(17) . . ? C32_2 Si21_2 C22_2 113.3(2) . . ? O20_2 Si21_2 C26_2 109.00(17) . . ? C32_2 Si21_2 C26_2 111.40(19) . . ? C22_2 Si21_2 C26_2 109.13(19) . . ? C25_2 C22_2 C23_2 108.6(4) . . ? C25_2 C22_2 C24_2 108.2(4) . . ? C23_2 C22_2 C24_2 107.7(4) . . ? C25_2 C22_2 Si21_2 111.9(3) . . ? C23_2 C22_2 Si21_2 112.3(3) . . ? C24_2 C22_2 Si21_2 108.0(3) . . ? C22_2 C23_2 H23D_2 109.5 . . ? C22_2 C23_2 H23E_2 109.5 . . ? H23D_2 C23_2 H23E_2 109.5 . . ? C22_2 C23_2 H23F_2 109.5 . . ? H23D_2 C23_2 H23F_2 109.5 . . ? H23E_2 C23_2 H23F_2 109.5 . . ? C22_2 C24_2 H24D_2 109.5 . . ? C22_2 C24_2 H24E_2 109.5 . . ? H24D_2 C24_2 H24E_2 109.5 . . ? C22_2 C24_2 H24F_2 109.5 . . ? H24D_2 C24_2 H24F_2 109.5 . . ? H24E_2 C24_2 H24F_2 109.5 . . ? C22_2 C25_2 H25D_2 109.5 . . ? C22_2 C25_2 H25E_2 109.5 . . ? H25D_2 C25_2 H25E_2 109.5 . . ? C22_2 C25_2 H25F_2 109.5 . . ? H25D_2 C25_2 H25F_2 109.5 . . ? H25E_2 C25_2 H25F_2 109.5 . . ? C31_2 C26_2 C27_2 116.8(4) . . ? C31_2 C26_2 Si21_2 120.3(3) . . ? C27_2 C26_2 Si21_2 122.8(3) . . ? C28_2 C27_2 C26_2 121.6(4) . . ? C28_2 C27_2 H27B_2 119.2 . . ? C26_2 C27_2 H27B_2 119.2 . . ? C29_2 C28_2 C27_2 119.8(5) . . ? C29_2 C28_2 H28B_2 120.1 . . ? C27_2 C28_2 H28B_2 120.1 . . ? C28_2 C29_2 C30_2 120.3(4) . . ? C28_2 C29_2 H29B_2 119.9 . . ? C30_2 C29_2 H29B_2 119.9 . . ? C29_2 C30_2 C31_2 119.4(4) . . ? C29_2 C30_2 H30B_2 120.3 . . ? C31_2 C30_2 H30B_2 120.3 . . ? C30_2 C31_2 C26_2 122.1(4) . . ? C30_2 C31_2 H31B_2 119.0 . . ? C26_2 C31_2 H31B_2 119.0 . . ? C37_2 C32_2 C33_2 116.1(4) . . ? C37_2 C32_2 Si21_2 123.9(3) . . ? C33_2 C32_2 Si21_2 120.0(4) . . ? C32_2 C33_2 C34_2 122.1(5) . . ? C32_2 C33_2 H33B_2 118.9 . . ? C34_2 C33_2 H33B_2 118.9 . . ? C35_2 C34_2 C33_2 120.2(5) . . ? C35_2 C34_2 H34B_2 119.9 . . ? C33_2 C34_2 H34B_2 119.9 . . ? C34_2 C35_2 C36_2 119.5(5) . . ? C34_2 C35_2 H35B_2 120.2 . . ? C36_2 C35_2 H35B_2 120.2 . . ? C35_2 C36_2 C37_2 120.3(6) . . ? C35_2 C36_2 H36B_2 119.9 . . ? C37_2 C36_2 H36B_2 119.9 . . ? C32_2 C37_2 C36_2 121.7(5) . . ? C32_2 C37_2 H37B_2 119.1 . . ? C36_2 C37_2 H37B_2 119.1 . . ? 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 O9_1 N1_1 C2_1 C3_1 -71.8(4) . . . . ? C6_1 N1_1 C2_1 C3_1 48.6(5) . . . . ? N1_1 C2_1 C3_1 C4_1 -53.5(5) . . . . ? C2_1 C3_1 C4_1 C5_1 57.7(5) . . . . ? C3_1 C4_1 C5_1 C6_1 -57.5(5) . . . . ? O9_1 N1_1 C6_1 C7_1 -42.6(3) . . . . ? C2_1 N1_1 C6_1 C7_1 -164.0(3) . . . . ? O9_1 N1_1 C6_1 C5_1 75.7(3) . . . . ? C2_1 N1_1 C6_1 C5_1 -45.7(4) . . . . ? O9_1 N1_1 C6_1 C16_1 -160.6(3) . . . . ? C2_1 N1_1 C6_1 C16_1 78.0(4) . . . . ? C4_1 C5_1 C6_1 C7_1 158.0(3) . . . . ? C4_1 C5_1 C6_1 N1_1 49.9(4) . . . . ? C4_1 C5_1 C6_1 C16_1 -70.7(4) . . . . ? N1_1 C6_1 C7_1 C8_1 41.8(3) . . . . ? C5_1 C6_1 C7_1 C8_1 -73.8(4) . . . . ? C16_1 C6_1 C7_1 C8_1 155.2(3) . . . . ? C6_1 C7_1 C8_1 O9_1 -27.7(4) . . . . ? C6_1 C7_1 C8_1 C10_1 -149.7(3) . . . . ? C2_1 N1_1 O9_1 C8_1 153.8(3) . . . . ? C6_1 N1_1 O9_1 C8_1 27.0(3) . . . . ? C10_1 C8_1 O9_1 N1_1 124.2(3) . . . . ? C7_1 C8_1 O9_1 N1_1 0.6(4) . . . . ? O9_1 C8_1 C10_1 C15_1 -23.6(5) . . . . ? C7_1 C8_1 C10_1 C15_1 94.3(4) . . . . ? O9_1 C8_1 C10_1 C11_1 159.9(3) . . . . ? C7_1 C8_1 C10_1 C11_1 -82.2(4) . . . . ? C15_1 C10_1 C11_1 C12_1 -0.2(6) . . . . ? C8_1 C10_1 C11_1 C12_1 176.5(4) . . . . ? C10_1 C11_1 C12_1 C13_1 1.0(7) . . . . ? C11_1 C12_1 C13_1 C14_1 -1.3(7) . . . . ? C12_1 C13_1 C14_1 C15_1 0.7(7) . . . . ? C11_1 C10_1 C15_1 C14_1 -0.3(6) . . . . ? C8_1 C10_1 C15_1 C14_1 -176.8(4) . . . . ? C13_1 C14_1 C15_1 C10_1 0.1(6) . . . . ? C7_1 C6_1 C16_1 C17_1 60.8(4) . . . . ? N1_1 C6_1 C16_1 C17_1 167.9(3) . . . . ? C5_1 C6_1 C16_1 C17_1 -70.4(4) . . . . ? C6_1 C16_1 C17_1 C18_1 159.6(3) . . . . ? C16_1 C17_1 C18_1 C19_1 -68.3(4) . . . . ? C17_1 C18_1 C19_1 O20_1 -54.4(4) . . . . ? C18_1 C19_1 O20_1 Si21_1 -131.3(3) . . . . ? C19_1 O20_1 Si21_1 C32_1 -31.6(3) . . . . ? C19_1 O20_1 Si21_1 C26_1 86.6(3) . . . . ? C19_1 O20_1 Si21_1 C22_1 -155.9(3) . . . . ? O20_1 Si21_1 C22_1 C25_1 177.8(4) . . . . ? C32_1 Si21_1 C22_1 C25_1 58.5(5) . . . . ? C26_1 Si21_1 C22_1 C25_1 -65.4(5) . . . . ? O20_1 Si21_1 C22_1 C23_1 54.3(4) . . . . ? C32_1 Si21_1 C22_1 C23_1 -65.0(4) . . . . ? C26_1 Si21_1 C22_1 C23_1 171.0(4) . . . . ? O20_1 Si21_1 C22_1 C24_1 -63.6(4) . . . . ? C32_1 Si21_1 C22_1 C24_1 177.1(4) . . . . ? C26_1 Si21_1 C22_1 C24_1 53.2(4) . . . . ? O20_1 Si21_1 C26_1 C27_1 -167.5(4) . . . . ? C32_1 Si21_1 C26_1 C27_1 -50.3(4) . . . . ? C22_1 Si21_1 C26_1 C27_1 77.3(4) . . . . ? O20_1 Si21_1 C26_1 C31_1 15.3(4) . . . . ? C32_1 Si21_1 C26_1 C31_1 132.5(3) . . . . ? C22_1 Si21_1 C26_1 C31_1 -99.9(4) . . . . ? C31_1 C26_1 C27_1 C28_1 -0.2(7) . . . . ? Si21_1 C26_1 C27_1 C28_1 -177.4(4) . . . . ? C26_1 C27_1 C28_1 C29_1 -0.1(9) . . . . ? C27_1 C28_1 C29_1 C30_1 0.8(9) . . . . ? C28_1 C29_1 C30_1 C31_1 -1.1(8) . . . . ? C29_1 C30_1 C31_1 C26_1 0.8(7) . . . . ? C27_1 C26_1 C31_1 C30_1 -0.1(7) . . . . ? Si21_1 C26_1 C31_1 C30_1 177.2(3) . . . . ? O20_1 Si21_1 C32_1 C33_1 -76.8(4) . . . . ? C26_1 Si21_1 C32_1 C33_1 165.5(4) . . . . ? C22_1 Si21_1 C32_1 C33_1 41.4(5) . . . . ? O20_1 Si21_1 C32_1 C37_1 91.7(4) . . . . ? C26_1 Si21_1 C32_1 C37_1 -25.9(4) . . . . ? C22_1 Si21_1 C32_1 C37_1 -150.0(4) . . . . ? C37_1 C32_1 C33_1 C34_1 -0.1(8) . . . . ? Si21_1 C32_1 C33_1 C34_1 169.0(4) . . . . ? C32_1 C33_1 C34_1 C35_1 -0.3(9) . . . . ? C33_1 C34_1 C35_1 C36_1 0.1(9) . . . . ? C34_1 C35_1 C36_1 C37_1 0.4(8) . . . . ? C35_1 C36_1 C37_1 C32_1 -0.9(8) . . . . ? C33_1 C32_1 C37_1 C36_1 0.7(7) . . . . ? Si21_1 C32_1 C37_1 C36_1 -168.7(4) . . . . ? O9_2 N1_2 C2_2 C3_2 -71.2(4) . . . . ? C6_2 N1_2 C2_2 C3_2 49.3(4) . . . . ? N1_2 C2_2 C3_2 C4_2 -54.0(5) . . . . ? C2_2 C3_2 C4_2 C5_2 57.7(5) . . . . ? C3_2 C4_2 C5_2 C6_2 -56.5(5) . . . . ? O9_2 N1_2 C6_2 C5_2 75.4(3) . . . . ? C2_2 N1_2 C6_2 C5_2 -46.0(4) . . . . ? O9_2 N1_2 C6_2 C7_2 -42.7(3) . . . . ? C2_2 N1_2 C6_2 C7_2 -164.0(3) . . . . ? O9_2 N1_2 C6_2 C16_2 -160.3(3) . . . . ? C2_2 N1_2 C6_2 C16_2 78.4(4) . . . . ? C4_2 C5_2 C6_2 N1_2 48.9(4) . . . . ? C4_2 C5_2 C6_2 C7_2 156.8(3) . . . . ? C4_2 C5_2 C6_2 C16_2 -72.5(4) . . . . ? N1_2 C6_2 C7_2 C8_2 41.5(3) . . . . ? C5_2 C6_2 C7_2 C8_2 -74.2(4) . . . . ? C16_2 C6_2 C7_2 C8_2 155.1(3) . . . . ? C6_2 C7_2 C8_2 O9_2 -27.1(4) . . . . ? C6_2 C7_2 C8_2 C10_2 -148.6(3) . . . . ? C2_2 N1_2 O9_2 C8_2 154.4(3) . . . . ? C6_2 N1_2 O9_2 C8_2 27.7(3) . . . . ? C10_2 C8_2 O9_2 N1_2 122.7(3) . . . . ? C7_2 C8_2 O9_2 N1_2 0.0(4) . . . . ? O9_2 C8_2 C10_2 C15_2 -22.1(5) . . . . ? C7_2 C8_2 C10_2 C15_2 95.3(4) . . . . ? O9_2 C8_2 C10_2 C11_2 161.7(3) . . . . ? C7_2 C8_2 C10_2 C11_2 -80.9(4) . . . . ? C15_2 C10_2 C11_2 C12_2 -0.3(6) . . . . ? C8_2 C10_2 C11_2 C12_2 176.1(4) . . . . ? C10_2 C11_2 C12_2 C13_2 0.2(7) . . . . ? C11_2 C12_2 C13_2 C14_2 -0.2(7) . . . . ? C12_2 C13_2 C14_2 C15_2 0.4(7) . . . . ? C11_2 C10_2 C15_2 C14_2 0.6(6) . . . . ? C8_2 C10_2 C15_2 C14_2 -175.6(4) . . . . ? C13_2 C14_2 C15_2 C10_2 -0.6(6) . . . . ? N1_2 C6_2 C16_2 C17_2 165.1(3) . . . . ? C5_2 C6_2 C16_2 C17_2 -72.4(4) . . . . ? C7_2 C6_2 C16_2 C17_2 58.2(4) . . . . ? C6_2 C16_2 C17_2 C18_2 159.1(3) . . . . ? C16_2 C17_2 C18_2 C19_2 -67.7(4) . . . . ? C17_2 C18_2 C19_2 O20_2 -50.2(5) . . . . ? C18_2 C19_2 O20_2 Si21_2 -131.9(3) . . . . ? C19_2 O20_2 Si21_2 C32_2 -35.5(4) . . . . ? C19_2 O20_2 Si21_2 C22_2 -157.1(3) . . . . ? C19_2 O20_2 Si21_2 C26_2 86.0(3) . . . . ? O20_2 Si21_2 C22_2 C25_2 -179.6(3) . . . . ? C32_2 Si21_2 C22_2 C25_2 62.0(4) . . . . ? C26_2 Si21_2 C22_2 C25_2 -62.7(4) . . . . ? O20_2 Si21_2 C22_2 C23_2 57.9(3) . . . . ? C32_2 Si21_2 C22_2 C23_2 -60.5(4) . . . . ? C26_2 Si21_2 C22_2 C23_2 174.8(3) . . . . ? O20_2 Si21_2 C22_2 C24_2 -60.7(3) . . . . ? C32_2 Si21_2 C22_2 C24_2 -179.0(3) . . . . ? C26_2 Si21_2 C22_2 C24_2 56.2(4) . . . . ? O20_2 Si21_2 C26_2 C31_2 8.1(4) . . . . ? C32_2 Si21_2 C26_2 C31_2 127.8(3) . . . . ? C22_2 Si21_2 C26_2 C31_2 -106.4(3) . . . . ? O20_2 Si21_2 C26_2 C27_2 -174.8(3) . . . . ? C32_2 Si21_2 C26_2 C27_2 -55.2(4) . . . . ? C22_2 Si21_2 C26_2 C27_2 70.6(4) . . . . ? C31_2 C26_2 C27_2 C28_2 -2.4(6) . . . . ? Si21_2 C26_2 C27_2 C28_2 -179.6(3) . . . . ? C26_2 C27_2 C28_2 C29_2 2.0(7) . . . . ? C27_2 C28_2 C29_2 C30_2 -0.8(7) . . . . ? C28_2 C29_2 C30_2 C31_2 0.0(7) . . . . ? C29_2 C30_2 C31_2 C26_2 -0.5(7) . . . . ? C27_2 C26_2 C31_2 C30_2 1.6(6) . . . . ? Si21_2 C26_2 C31_2 C30_2 178.8(3) . . . . ? O20_2 Si21_2 C32_2 C37_2 129.1(5) . . . . ? C22_2 Si21_2 C32_2 C37_2 -114.3(5) . . . . ? C26_2 Si21_2 C32_2 C37_2 9.2(6) . . . . ? O20_2 Si21_2 C32_2 C33_2 -50.1(5) . . . . ? C22_2 Si21_2 C32_2 C33_2 66.4(5) . . . . ? C26_2 Si21_2 C32_2 C33_2 -170.1(4) . . . . ? C37_2 C32_2 C33_2 C34_2 -3.0(9) . . . . ? Si21_2 C32_2 C33_2 C34_2 176.3(5) . . . . ? C32_2 C33_2 C34_2 C35_2 1.4(10) . . . . ? C33_2 C34_2 C35_2 C36_2 1.4(11) . . . . ? C34_2 C35_2 C36_2 C37_2 -2.4(11) . . . . ? C33_2 C32_2 C37_2 C36_2 2.0(10) . . . . ? Si21_2 C32_2 C37_2 C36_2 -177.2(6) . . . . ? C35_2 C36_2 C37_2 C32_2 0.6(12) . . . . ? data_ah0118 _database_code_depnum_ccdc_archive 'CCDC 865489' #TrackingRef 'AH0118.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H41 N O2 Si' _chemical_formula_weight 403.67 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.7031(3) _cell_length_b 9.8991(6) _cell_length_c 15.8805(8) _cell_angle_alpha 90.00 _cell_angle_beta 98.831(3) _cell_angle_gamma 90.00 _cell_volume 1196.59(11) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4554 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.120 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.890 _exptl_absorpt_correction_T_max 1.120 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; Absolute structure determination. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 7454 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0650 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.76 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.988 _reflns_number_total 4564 _reflns_number_gt 3846 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0603P)^2^+0.0031P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _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 0.08(11) _refine_ls_number_reflns 4564 _refine_ls_number_parameters 260 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1107 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.215 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.062 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 1.22139(7) 0.29807(6) 0.84887(3) 0.02241(15) Uani 1 1 d . . . O1 O 0.86524(18) 0.69937(17) 0.54541(9) 0.0268(4) Uani 1 1 d . . . O2 O 0.5426(2) 0.38154(18) 0.53729(11) 0.0448(5) Uani 1 1 d . . . H2 H 0.4689 0.3500 0.4977 0.067 Uiso 1 1 calc R . . N1 N 0.7134(2) 0.72055(18) 0.59123(10) 0.0194(4) Uani 1 1 d . . . C1 C 0.7896(2) 0.7987(3) 0.66816(11) 0.0202(4) Uani 1 1 d . . . C2 C 0.6762(3) 0.7886(3) 0.73887(13) 0.0288(5) Uani 1 1 d . . . H2B H 0.7408 0.8294 0.7914 0.035 Uiso 1 1 calc R . . H2C H 0.5675 0.8417 0.7221 0.035 Uiso 1 1 calc R . . C3 C 0.6264(3) 0.6443(3) 0.75817(14) 0.0327(6) Uani 1 1 d . . . H3A H 0.7329 0.5922 0.7812 0.039 Uiso 1 1 calc R . . H3B H 0.5459 0.6442 0.8011 0.039 Uiso 1 1 calc R . . C4 C 0.5368(3) 0.5806(3) 0.67575(14) 0.0351(6) Uani 1 1 d . . . H4A H 0.5035 0.4864 0.6870 0.042 Uiso 1 1 calc R . . H4B H 0.4281 0.6312 0.6545 0.042 Uiso 1 1 calc R . . C5 C 0.6565(3) 0.5810(2) 0.60807(13) 0.0236(5) Uani 1 1 d . . . H5A H 0.7627 0.5250 0.6285 0.028 Uiso 1 1 calc R . . C6 C 0.9759(3) 0.7379(2) 0.68967(12) 0.0217(4) Uani 1 1 d . . . H6A H 0.9653 0.6410 0.7061 0.026 Uiso 1 1 calc R . . C7 C 1.0245(3) 0.7436(3) 0.59985(13) 0.0283(5) Uani 1 1 d . . . H7A H 1.1239 0.6806 0.5948 0.034 Uiso 1 1 calc R . . C8 C 1.0681(3) 0.8852(3) 0.57374(16) 0.0382(6) Uani 1 1 d . . . H8A H 1.1086 0.8830 0.5175 0.046 Uiso 1 1 calc R . . H8B H 1.1636 0.9233 0.6159 0.046 Uiso 1 1 calc R . . C9 C 0.9035(3) 0.9733(3) 0.56892(14) 0.0357(6) Uani 1 1 d . . . H9A H 0.8255 0.9550 0.5146 0.043 Uiso 1 1 calc R . . H9B H 0.9384 1.0696 0.5690 0.043 Uiso 1 1 calc R . . C10 C 0.8017(3) 0.9482(2) 0.64303(13) 0.0271(5) Uani 1 1 d . . . H10A H 0.6811 0.9842 0.6274 0.033 Uiso 1 1 calc R . . H10B H 0.8588 0.9993 0.6933 0.033 Uiso 1 1 calc R . . C11 C 1.0979(3) 0.8080(3) 0.75851(12) 0.0255(5) Uani 1 1 d . . . H11A H 1.1084 0.9033 0.7545 0.031 Uiso 1 1 calc R . . C12 C 1.1930(3) 0.7469(2) 0.82499(14) 0.0274(5) Uani 1 1 d . . . H12A H 1.2623 0.8022 0.8660 0.033 Uiso 1 1 calc R . . C13 C 1.1980(3) 0.6049(2) 0.83882(12) 0.0245(5) Uani 1 1 d . . . C14 C 1.2092(3) 0.4845(2) 0.84936(13) 0.0265(5) Uani 1 1 d . . . C15 C 0.5637(3) 0.5225(2) 0.52407(14) 0.0289(5) Uani 1 1 d . . . H15A H 0.4478 0.5662 0.5076 0.035 Uiso 1 1 calc R . . H15B H 0.6350 0.5379 0.4781 0.035 Uiso 1 1 calc R . . C16 C 1.4605(3) 0.2522(3) 0.85527(16) 0.0354(6) Uani 1 1 d . . . H16A H 1.4988 0.2899 0.8026 0.042 Uiso 1 1 calc R . . C17 C 1.5784(3) 0.3174(5) 0.9300(2) 0.0746(12) Uani 1 1 d . . . H17A H 1.7018 0.3032 0.9239 0.112 Uiso 1 1 calc R . . H17B H 1.5554 0.2765 0.9834 0.112 Uiso 1 1 calc R . . H17C H 1.5540 0.4145 0.9308 0.112 Uiso 1 1 calc R . . C18 C 1.4904(4) 0.1001(3) 0.8521(3) 0.0768(12) Uani 1 1 d . . . H18A H 1.6125 0.0823 0.8450 0.115 Uiso 1 1 calc R . . H18B H 1.4112 0.0613 0.8040 0.115 Uiso 1 1 calc R . . H18C H 1.4668 0.0589 0.9053 0.115 Uiso 1 1 calc R . . C19 C 1.1099(3) 0.2359(3) 0.93880(14) 0.0298(5) Uani 1 1 d . . . H19A H 0.9947 0.2844 0.9322 0.036 Uiso 1 1 calc R . . C20 C 1.2033(4) 0.2735(3) 1.02770(15) 0.0491(8) Uani 1 1 d . . . H20A H 1.1236 0.2591 1.0694 0.074 Uiso 1 1 calc R . . H20B H 1.2385 0.3686 1.0283 0.074 Uiso 1 1 calc R . . H20C H 1.3078 0.2167 1.0424 0.074 Uiso 1 1 calc R . . C21 C 1.0634(4) 0.0858(3) 0.93470(17) 0.0479(7) Uani 1 1 d . . . H21A H 0.9954 0.0637 0.9802 0.072 Uiso 1 1 calc R . . H21B H 1.1715 0.0320 0.9419 0.072 Uiso 1 1 calc R . . H21C H 0.9934 0.0652 0.8793 0.072 Uiso 1 1 calc R . . C22 C 1.0927(3) 0.2447(3) 0.74318(14) 0.0309(5) Uani 1 1 d . . . H22A H 1.1010 0.1442 0.7391 0.037 Uiso 1 1 calc R . . C23 C 0.8980(3) 0.2819(3) 0.73702(16) 0.0424(7) Uani 1 1 d . . . H23A H 0.8363 0.2586 0.6802 0.064 Uiso 1 1 calc R . . H23B H 0.8870 0.3791 0.7466 0.064 Uiso 1 1 calc R . . H23C H 0.8462 0.2319 0.7802 0.064 Uiso 1 1 calc R . . C24 C 1.1688(4) 0.3060(4) 0.66788(15) 0.0566(8) Uani 1 1 d . . . H24A H 1.0982 0.2770 0.6143 0.085 Uiso 1 1 calc R . . H24B H 1.2903 0.2754 0.6696 0.085 Uiso 1 1 calc R . . H24C H 1.1664 0.4048 0.6717 0.085 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Si1 0.0256(3) 0.0195(3) 0.0214(3) 0.0003(3) 0.0014(2) 0.0004(3) O1 0.0241(7) 0.0375(10) 0.0194(7) -0.0073(7) 0.0052(6) -0.0051(7) O2 0.0551(12) 0.0230(10) 0.0473(11) -0.0037(8) -0.0210(9) -0.0089(9) N1 0.0185(8) 0.0214(11) 0.0184(8) -0.0024(7) 0.0030(6) -0.0012(7) C1 0.0244(10) 0.0178(10) 0.0173(9) -0.0001(10) -0.0006(7) 0.0003(10) C2 0.0333(11) 0.0318(13) 0.0218(10) -0.0037(11) 0.0063(8) 0.0028(12) C3 0.0348(12) 0.0408(16) 0.0239(11) 0.0013(10) 0.0090(9) -0.0078(11) C4 0.0348(12) 0.0394(15) 0.0314(12) -0.0017(11) 0.0063(10) -0.0141(12) C5 0.0230(10) 0.0212(12) 0.0245(11) -0.0006(9) -0.0029(8) -0.0023(10) C6 0.0240(10) 0.0183(11) 0.0212(10) -0.0024(9) -0.0017(8) -0.0015(9) C7 0.0200(10) 0.0381(14) 0.0252(11) -0.0017(10) -0.0013(8) -0.0020(10) C8 0.0344(12) 0.0491(17) 0.0309(12) 0.0012(12) 0.0048(10) -0.0163(13) C9 0.0466(14) 0.0296(15) 0.0281(12) 0.0084(11) -0.0033(10) -0.0105(12) C10 0.0322(11) 0.0194(11) 0.0265(11) 0.0001(10) -0.0055(8) -0.0019(11) C11 0.0275(10) 0.0175(12) 0.0291(11) -0.0018(10) -0.0035(8) -0.0028(10) C12 0.0296(11) 0.0201(11) 0.0292(11) -0.0032(9) -0.0056(9) -0.0052(10) C13 0.0242(11) 0.0259(13) 0.0203(10) -0.0021(9) -0.0063(8) 0.0015(10) C14 0.0292(11) 0.0256(14) 0.0228(11) 0.0004(9) -0.0024(8) -0.0024(10) C15 0.0293(11) 0.0231(13) 0.0306(12) -0.0040(10) -0.0069(9) -0.0033(10) C16 0.0316(12) 0.0345(15) 0.0417(13) -0.0008(11) 0.0106(10) 0.0046(12) C17 0.0264(13) 0.120(4) 0.073(2) -0.024(2) -0.0082(13) 0.0034(19) C18 0.0431(16) 0.041(2) 0.149(4) 0.003(2) 0.0257(19) 0.0162(16) C19 0.0325(12) 0.0283(13) 0.0293(11) 0.0008(10) 0.0071(9) 0.0011(11) C20 0.0597(16) 0.063(2) 0.0260(12) 0.0011(13) 0.0102(11) -0.0024(16) C21 0.0621(17) 0.0389(17) 0.0456(16) 0.0087(14) 0.0180(13) -0.0079(15) C22 0.0410(13) 0.0227(12) 0.0280(11) -0.0007(10) 0.0022(9) -0.0078(11) C23 0.0456(14) 0.0288(16) 0.0447(14) 0.0006(12) -0.0181(11) 0.0033(13) C24 0.083(2) 0.064(2) 0.0219(12) -0.0052(14) 0.0063(12) -0.035(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 C14 1.848(2) . ? Si1 C19 1.879(2) . ? Si1 C16 1.885(2) . ? Si1 C22 1.889(2) . ? O1 C7 1.456(3) . ? O1 N1 1.484(2) . ? O2 C15 1.424(3) . ? O2 H2 0.8400 . ? N1 C5 1.486(3) . ? N1 C1 1.489(3) . ? C1 C2 1.528(3) . ? C1 C10 1.539(3) . ? C1 C6 1.545(3) . ? C2 C3 1.522(4) . ? C2 H2B 0.9900 . ? C2 H2C 0.9900 . ? C3 C4 1.520(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.520(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C15 1.527(3) . ? C5 H5A 1.0000 . ? C6 C11 1.498(3) . ? C6 C7 1.530(3) . ? C6 H6A 1.0000 . ? C7 C8 1.513(4) . ? C7 H7A 1.0000 . ? C8 C9 1.531(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.532(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.334(3) . ? C11 H11A 0.9500 . ? C12 C13 1.423(3) . ? C12 H12A 0.9500 . ? C13 C14 1.205(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.523(4) . ? C16 C18 1.525(4) . ? C16 H16A 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C21 1.528(4) . ? C19 C20 1.529(3) . ? C19 H19A 1.0000 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.533(3) . ? C22 C24 1.535(3) . ? C22 H22A 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 C14 Si1 C19 107.11(11) . . ? C14 Si1 C16 106.89(11) . . ? C19 Si1 C16 115.91(11) . . ? C14 Si1 C22 105.24(10) . . ? C19 Si1 C22 110.17(10) . . ? C16 Si1 C22 110.84(11) . . ? C7 O1 N1 108.78(14) . . ? C15 O2 H2 109.5 . . ? O1 N1 C5 103.49(15) . . ? O1 N1 C1 103.58(13) . . ? C5 N1 C1 115.19(16) . . ? N1 C1 C2 111.78(17) . . ? N1 C1 C10 108.59(15) . . ? C2 C1 C10 108.5(2) . . ? N1 C1 C6 102.39(16) . . ? C2 C1 C6 115.34(17) . . ? C10 C1 C6 109.95(18) . . ? C3 C2 C1 113.6(2) . . ? C3 C2 H2B 108.9 . . ? C1 C2 H2B 108.9 . . ? C3 C2 H2C 108.9 . . ? C1 C2 H2C 108.9 . . ? H2B C2 H2C 107.7 . . ? C4 C3 C2 108.12(19) . . ? C4 C3 H3A 110.1 . . ? C2 C3 H3A 110.1 . . ? C4 C3 H3B 110.1 . . ? C2 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? C5 C4 C3 111.31(18) . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? N1 C5 C4 110.93(18) . . ? N1 C5 C15 107.84(17) . . ? C4 C5 C15 111.30(18) . . ? N1 C5 H5A 108.9 . . ? C4 C5 H5A 108.9 . . ? C15 C5 H5A 108.9 . . ? C11 C6 C7 116.54(17) . . ? C11 C6 C1 115.98(19) . . ? C7 C6 C1 97.53(15) . . ? C11 C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? C1 C6 H6A 108.7 . . ? O1 C7 C8 108.55(18) . . ? O1 C7 C6 103.76(16) . . ? C8 C7 C6 112.7(2) . . ? O1 C7 H7A 110.5 . . ? C8 C7 H7A 110.5 . . ? C6 C7 H7A 110.5 . . ? C7 C8 C9 108.93(18) . . ? C7 C8 H8A 109.9 . . ? C9 C8 H8A 109.9 . . ? C7 C8 H8B 109.9 . . ? C9 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? C8 C9 C10 112.75(19) . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C9 C10 C1 114.46(19) . . ? C9 C10 H10A 108.6 . . ? C1 C10 H10A 108.6 . . ? C9 C10 H10B 108.6 . . ? C1 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C6 125.1(2) . . ? C12 C11 H11A 117.5 . . ? C6 C11 H11A 117.5 . . ? C11 C12 C13 124.6(2) . . ? C11 C12 H12A 117.7 . . ? C13 C12 H12A 117.7 . . ? C14 C13 C12 177.2(3) . . ? C13 C14 Si1 171.87(19) . . ? O2 C15 C5 106.93(18) . . ? O2 C15 H15A 110.3 . . ? C5 C15 H15A 110.3 . . ? O2 C15 H15B 110.3 . . ? C5 C15 H15B 110.3 . . ? H15A C15 H15B 108.6 . . ? C17 C16 C18 111.7(3) . . ? C17 C16 Si1 113.64(18) . . ? C18 C16 Si1 112.80(19) . . ? C17 C16 H16A 106.0 . . ? C18 C16 H16A 106.0 . . ? Si1 C16 H16A 106.0 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C21 C19 C20 110.5(2) . . ? C21 C19 Si1 114.69(17) . . ? C20 C19 Si1 114.63(17) . . ? C21 C19 H19A 105.3 . . ? C20 C19 H19A 105.3 . . ? Si1 C19 H19A 105.3 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C24 110.0(2) . . ? C23 C22 Si1 111.36(17) . . ? C24 C22 Si1 111.75(17) . . ? C23 C22 H22A 107.9 . . ? C24 C22 H22A 107.9 . . ? Si1 C22 H22A 107.9 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? 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 C7 O1 N1 C5 -111.86(17) . . . . ? C7 O1 N1 C1 8.7(2) . . . . ? O1 N1 C1 C2 -159.64(18) . . . . ? C5 N1 C1 C2 -47.4(2) . . . . ? O1 N1 C1 C10 80.66(18) . . . . ? C5 N1 C1 C10 -167.09(16) . . . . ? O1 N1 C1 C6 -35.61(19) . . . . ? C5 N1 C1 C6 76.6(2) . . . . ? N1 C1 C2 C3 49.7(2) . . . . ? C10 C1 C2 C3 169.42(17) . . . . ? C6 C1 C2 C3 -66.7(2) . . . . ? C1 C2 C3 C4 -55.4(2) . . . . ? C2 C3 C4 C5 58.9(3) . . . . ? O1 N1 C5 C4 163.86(15) . . . . ? C1 N1 C5 C4 51.5(2) . . . . ? O1 N1 C5 C15 -74.03(18) . . . . ? C1 N1 C5 C15 173.67(16) . . . . ? C3 C4 C5 N1 -57.5(2) . . . . ? C3 C4 C5 C15 -177.5(2) . . . . ? N1 C1 C6 C11 172.17(17) . . . . ? C2 C1 C6 C11 -66.2(3) . . . . ? C10 C1 C6 C11 56.9(2) . . . . ? N1 C1 C6 C7 47.7(2) . . . . ? C2 C1 C6 C7 169.3(2) . . . . ? C10 C1 C6 C7 -67.57(19) . . . . ? N1 O1 C7 C8 -98.06(19) . . . . ? N1 O1 C7 C6 22.1(2) . . . . ? C11 C6 C7 O1 -166.16(19) . . . . ? C1 C6 C7 O1 -42.1(2) . . . . ? C11 C6 C7 C8 -48.9(3) . . . . ? C1 C6 C7 C8 75.1(2) . . . . ? O1 C7 C8 C9 49.9(2) . . . . ? C6 C7 C8 C9 -64.4(2) . . . . ? C7 C8 C9 C10 42.0(3) . . . . ? C8 C9 C10 C1 -40.5(3) . . . . ? N1 C1 C10 C9 -55.1(2) . . . . ? C2 C1 C10 C9 -176.77(16) . . . . ? C6 C1 C10 C9 56.2(2) . . . . ? C7 C6 C11 C12 -115.5(2) . . . . ? C1 C6 C11 C12 130.6(2) . . . . ? C6 C11 C12 C13 2.6(4) . . . . ? N1 C5 C15 O2 168.31(17) . . . . ? C4 C5 C15 O2 -69.8(2) . . . . ? C14 Si1 C16 C17 53.7(3) . . . . ? C19 Si1 C16 C17 -65.6(3) . . . . ? C22 Si1 C16 C17 167.9(2) . . . . ? C14 Si1 C16 C18 -177.9(2) . . . . ? C19 Si1 C16 C18 62.8(3) . . . . ? C22 Si1 C16 C18 -63.7(3) . . . . ? C14 Si1 C19 C21 164.54(18) . . . . ? C16 Si1 C19 C21 -76.3(2) . . . . ? C22 Si1 C19 C21 50.6(2) . . . . ? C14 Si1 C19 C20 -66.1(2) . . . . ? C16 Si1 C19 C20 53.1(2) . . . . ? C22 Si1 C19 C20 179.95(19) . . . . ? C14 Si1 C22 C23 -64.6(2) . . . . ? C19 Si1 C22 C23 50.6(2) . . . . ? C16 Si1 C22 C23 -179.79(18) . . . . ? C14 Si1 C22 C24 58.9(2) . . . . ? C19 Si1 C22 C24 174.0(2) . . . . ? C16 Si1 C22 C24 -56.3(2) . . . . ? data_ah0125 _database_code_depnum_ccdc_archive 'CCDC 881632' #TrackingRef '11234_web_deposit_cif_file_0_AndrewBond_1336728016.AH0125.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H16 N2 O' _chemical_formula_sum 'C11 H16 N2 O' _chemical_formula_weight 192.26 _chemical_absolute_configuration unk 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 orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 9.6609(9) _cell_length_b 11.5354(11) _cell_length_c 9.1360(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1018.14(15) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3249 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.982 _exptl_absorpt_correction_T_max 1.029 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ? _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 5693 _diffrn_reflns_av_R_equivalents 0.0974 _diffrn_reflns_av_sigmaI/netI 0.1020 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.57 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _reflns_number_total 1705 _reflns_number_gt 1153 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo/Scalepack _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement SHELXL-97 _computing_publication_material SHELXL-97 _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^)+(0.0377P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.032(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; In the absence of significant anomalous scattering effects, the absolute structure cannot be determined. Friedel pairs have *not* been merged. ; _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1705 _refine_ls_number_parameters 128 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0803 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.0878 _refine_ls_wR_factor_gt 0.0754 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.982 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.126 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.034 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.64750(17) 0.13179(13) 0.26238(16) 0.0327(5) Uani 1 1 d . . . N1 N 0.5821(2) 0.18605(18) 0.13256(19) 0.0298(5) Uani 1 1 d . . . N2 N 0.9405(3) 0.28558(19) 0.1993(3) 0.0460(7) Uani 1 1 d . . . C1 C 0.4924(3) 0.2753(2) 0.2033(3) 0.0311(7) Uani 1 1 d . . . C2 C 0.3616(3) 0.2249(2) 0.2736(3) 0.0381(7) Uani 1 1 d . . . H2A H 0.3876 0.1838 0.3647 0.046 Uiso 1 1 calc R . . H2B H 0.2989 0.2893 0.3006 0.046 Uiso 1 1 calc R . . C3 C 0.2848(3) 0.1416(2) 0.1742(3) 0.0465(8) Uani 1 1 d . . . H3A H 0.2511 0.1831 0.0863 0.056 Uiso 1 1 calc R . . H3B H 0.2039 0.1089 0.2263 0.056 Uiso 1 1 calc R . . C4 C 0.3834(3) 0.0441(2) 0.1289(3) 0.0432(8) Uani 1 1 d . . . H4A H 0.4126 0.0000 0.2165 0.052 Uiso 1 1 calc R . . H4B H 0.3352 -0.0098 0.0618 0.052 Uiso 1 1 calc R . . C5 C 0.5091(2) 0.0941(2) 0.0535(3) 0.0339(7) Uani 1 1 d . . . H5A H 0.5752 0.0302 0.0348 0.041 Uiso 1 1 calc R . . H5B H 0.4799 0.1251 -0.0427 0.041 Uiso 1 1 calc R . . C6 C 0.4699(3) 0.3720(2) 0.0898(3) 0.0372(7) Uani 1 1 d . . . H6A H 0.4553 0.3391 -0.0091 0.045 Uiso 1 1 calc R . . H6B H 0.3890 0.4204 0.1160 0.045 Uiso 1 1 calc R . . C7 C 0.6035(3) 0.4429(2) 0.0955(3) 0.0369(7) Uani 1 1 d . . . H7A H 0.6784 0.4046 0.0396 0.044 Uiso 1 1 calc R . . H7B H 0.5890 0.5220 0.0562 0.044 Uiso 1 1 calc R . . C8 C 0.6371(3) 0.4463(2) 0.2590(3) 0.0403(7) Uani 1 1 d . . . H8A H 0.5847 0.5089 0.3083 0.048 Uiso 1 1 calc R . . H8B H 0.7373 0.4592 0.2749 0.048 Uiso 1 1 calc R . . C9 C 0.5931(3) 0.3271(2) 0.3170(2) 0.0325(7) Uani 1 1 d . . . H9A H 0.5450 0.3362 0.4133 0.039 Uiso 1 1 calc R . . C10 C 0.7061(3) 0.2317(2) 0.3290(2) 0.0333(7) Uani 1 1 d . . . H10A H 0.7254 0.2152 0.4346 0.040 Uiso 1 1 calc R . . C11 C 0.8375(3) 0.2628(2) 0.2536(3) 0.0338(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0385(11) 0.0315(10) 0.0281(9) 0.0022(8) -0.0066(8) 0.0035(8) N1 0.0331(13) 0.0341(13) 0.0221(11) -0.0006(9) -0.0028(10) 0.0029(11) N2 0.0440(17) 0.0500(16) 0.0439(14) 0.0015(12) -0.0060(12) -0.0047(13) C1 0.0366(17) 0.0325(16) 0.0243(13) 0.0002(12) 0.0001(11) 0.0060(12) C2 0.0373(17) 0.0450(16) 0.0321(14) 0.0010(14) 0.0077(13) 0.0075(14) C3 0.0347(17) 0.057(2) 0.0474(16) 0.0035(14) 0.0064(14) -0.0067(15) C4 0.0403(17) 0.0452(18) 0.0440(16) -0.0043(13) 0.0000(14) -0.0089(16) C5 0.0360(17) 0.0382(17) 0.0276(15) -0.0057(12) -0.0012(11) -0.0046(14) C6 0.0458(18) 0.0378(16) 0.0280(14) 0.0037(12) -0.0036(12) 0.0094(14) C7 0.0507(18) 0.0300(15) 0.0298(15) 0.0043(12) -0.0008(13) 0.0006(14) C8 0.0539(19) 0.0344(16) 0.0327(14) -0.0025(14) -0.0030(14) 0.0040(14) C9 0.0421(18) 0.0326(15) 0.0226(14) 0.0016(12) 0.0027(11) 0.0027(13) C10 0.0392(17) 0.0364(16) 0.0243(13) -0.0038(11) -0.0023(12) -0.0025(14) C11 0.0408(17) 0.0342(16) 0.0265(14) -0.0010(13) -0.0099(13) 0.0026(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 C10 1.421(3) . ? O1 N1 1.483(2) . ? N1 C5 1.464(3) . ? N1 C1 1.493(3) . ? N2 C11 1.142(3) . ? C1 C2 1.531(4) . ? C1 C6 1.538(3) . ? C1 C9 1.544(4) . ? C2 C3 1.516(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.531(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.510(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.529(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.529(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.534(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.554(3) . ? C9 H9A 1.0000 . ? C10 C11 1.489(4) . ? C10 H10A 1.0000 . ? 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 C10 O1 N1 99.82(15) . . ? C5 N1 O1 107.10(17) . . ? C5 N1 C1 115.71(19) . . ? O1 N1 C1 101.08(16) . . ? N1 C1 C2 113.5(2) . . ? N1 C1 C6 106.9(2) . . ? C2 C1 C6 116.2(2) . . ? N1 C1 C9 101.1(2) . . ? C2 C1 C9 112.6(2) . . ? C6 C1 C9 105.18(19) . . ? C3 C2 C1 113.2(2) . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2B 108.9 . . ? C1 C2 H2B 108.9 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 108.8(2) . . ? C2 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? C2 C3 H3B 109.9 . . ? C4 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? C5 C4 C3 110.1(2) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.2 . . ? N1 C5 C4 116.0(2) . . ? N1 C5 H5A 108.3 . . ? C4 C5 H5A 108.3 . . ? N1 C5 H5B 108.3 . . ? C4 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? C7 C6 C1 104.2(2) . . ? C7 C6 H6A 110.9 . . ? C1 C6 H6A 110.9 . . ? C7 C6 H6B 110.9 . . ? C1 C6 H6B 110.9 . . ? H6A C6 H6B 108.9 . . ? C8 C7 C6 103.1(2) . . ? C8 C7 H7A 111.1 . . ? C6 C7 H7A 111.1 . . ? C8 C7 H7B 111.1 . . ? C6 C7 H7B 111.1 . . ? H7A C7 H7B 109.1 . . ? C7 C8 C9 104.8(2) . . ? C7 C8 H8A 110.8 . . ? C9 C8 H8A 110.8 . . ? C7 C8 H8B 110.8 . . ? C9 C8 H8B 110.8 . . ? H8A C8 H8B 108.9 . . ? C8 C9 C1 106.79(19) . . ? C8 C9 C10 117.7(2) . . ? C1 C9 C10 102.47(18) . . ? C8 C9 H9A 109.8 . . ? C1 C9 H9A 109.8 . . ? C10 C9 H9A 109.8 . . ? O1 C10 C11 109.69(19) . . ? O1 C10 C9 105.34(19) . . ? C11 C10 C9 113.3(2) . . ? O1 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? N2 C11 C10 177.9(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 C10 O1 N1 C5 -177.12(17) . . . . ? C10 O1 N1 C1 -55.60(19) . . . . ? C5 N1 C1 C2 39.4(3) . . . . ? O1 N1 C1 C2 -75.8(2) . . . . ? C5 N1 C1 C6 -89.9(2) . . . . ? O1 N1 C1 C6 154.79(18) . . . . ? C5 N1 C1 C9 160.30(18) . . . . ? O1 N1 C1 C9 45.03(19) . . . . ? N1 C1 C2 C3 -47.6(3) . . . . ? C6 C1 C2 C3 76.9(3) . . . . ? C9 C1 C2 C3 -161.7(2) . . . . ? C1 C2 C3 C4 57.0(3) . . . . ? C2 C3 C4 C5 -57.8(3) . . . . ? O1 N1 C5 C4 68.7(3) . . . . ? C1 N1 C5 C4 -43.1(3) . . . . ? C3 C4 C5 N1 52.3(3) . . . . ? N1 C1 C6 C7 -79.0(2) . . . . ? C2 C1 C6 C7 153.2(2) . . . . ? C9 C1 C6 C7 27.9(3) . . . . ? C1 C6 C7 C8 -39.8(3) . . . . ? C6 C7 C8 C9 36.2(3) . . . . ? C7 C8 C9 C1 -19.0(3) . . . . ? C7 C8 C9 C10 95.4(2) . . . . ? N1 C1 C9 C8 105.6(2) . . . . ? C2 C1 C9 C8 -133.0(2) . . . . ? C6 C1 C9 C8 -5.5(3) . . . . ? N1 C1 C9 C10 -18.8(2) . . . . ? C2 C1 C9 C10 102.7(2) . . . . ? C6 C1 C9 C10 -129.8(2) . . . . ? N1 O1 C10 C11 -79.7(2) . . . . ? N1 O1 C10 C9 42.55(19) . . . . ? C8 C9 C10 O1 -131.5(2) . . . . ? C1 C9 C10 O1 -14.8(2) . . . . ? C8 C9 C10 C11 -11.6(3) . . . . ? C1 C9 C10 C11 105.1(2) . . . . ? data_cam49 _database_code_depnum_ccdc_archive 'CCDC 885212' #TrackingRef '11682_web_deposit_cif_file_0_AndrewBond_1338806903.CAM49.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H24 N2 O2' _chemical_formula_sum 'C19 H24 N2 O2' _chemical_formula_weight 312.40 _chemical_absolute_configuration unk 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 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.4675(15) _cell_length_b 11.662(2) _cell_length_c 8.6820(16) _cell_angle_alpha 90.00 _cell_angle_beta 103.279(5) _cell_angle_gamma 90.00 _cell_volume 834.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5022 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 29.43 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9968 _exptl_absorpt_correction_T_max 0.9992 _exptl_absorpt_process_details 'SADABS (Bruker, 1997)' _exptl_special_details ? _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6885 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'synchrotron gapped beam' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method '0.15 deg step phi scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 7499 _diffrn_reflns_av_R_equivalents 0.0575 _diffrn_reflns_av_sigmaI/netI 0.0779 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 29.29 _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 29.29 _diffrn_measured_fraction_theta_full 0.927 _reflns_number_total 3867 _reflns_number_gt 3224 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXL97 _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^)+(0.1018P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; In the absence of significant anomalous scattering effects, the absolute structure is not determined. Friedel pairs have *not* been merged. ; _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3867 _refine_ls_number_parameters 208 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_ref 0.1555 _refine_ls_wR_factor_gt 0.1524 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.550 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.079 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 N1 N 0.09780(19) -0.02584(17) 0.7385(2) 0.0208(4) Uani 1 1 d . . . C1 C -0.0230(2) -0.1202(2) 0.6985(3) 0.0213(4) Uani 1 1 d . . . C2 C 0.0113(3) -0.2188(2) 0.8187(3) 0.0299(5) Uani 1 1 d . . . H2A H -0.0875 -0.2667 0.8045 0.036 Uiso 1 1 calc R . . H2B H 0.0982 -0.2674 0.7940 0.036 Uiso 1 1 calc R . . C3 C 0.0617(3) -0.1835(3) 0.9908(3) 0.0349(6) Uani 1 1 d . . . H3A H -0.0321 -0.1499 1.0250 0.042 Uiso 1 1 calc R . . H3B H 0.0994 -0.2514 1.0576 0.042 Uiso 1 1 calc R . . C4 C 0.1971(3) -0.0962(2) 1.0100(3) 0.0312(5) Uani 1 1 d . . . H4A H 0.2923 -0.1314 0.9805 0.037 Uiso 1 1 calc R . . H4B H 0.2300 -0.0722 1.1222 0.037 Uiso 1 1 calc R . . C5 C 0.1431(2) 0.0081(2) 0.9068(3) 0.0227(4) Uani 1 1 d . . . H5A H 0.0469 0.0434 0.9371 0.027 Uiso 1 1 calc R . . C6 C -0.0182(3) -0.1673(2) 0.5340(3) 0.0273(5) Uani 1 1 d . . . H6A H 0.0851 -0.2091 0.5422 0.033 Uiso 1 1 calc R . . H6B H -0.1077 -0.2231 0.5012 0.033 Uiso 1 1 calc R . . C7 C -0.0332(3) -0.0758(3) 0.4062(3) 0.0351(6) Uani 1 1 d . . . H7A H 0.0718 -0.0353 0.4194 0.042 Uiso 1 1 calc R . . H7B H -0.0573 -0.1132 0.3011 0.042 Uiso 1 1 calc R . . C8 C -0.1652(3) 0.0109(3) 0.4119(3) 0.0345(6) Uani 1 1 d . . . H8A H -0.1523 0.0792 0.3481 0.041 Uiso 1 1 calc R . . H8B H -0.2731 -0.0231 0.3673 0.041 Uiso 1 1 calc R . . C9 C -0.1527(2) 0.0457(2) 0.5826(3) 0.0279(5) Uani 1 1 d . . . H9A H -0.2280 0.1105 0.5895 0.034 Uiso 1 1 calc R . . C10 C -0.1885(2) -0.0576(2) 0.6762(3) 0.0256(5) Uani 1 1 d . . . H10A H -0.2749 -0.1052 0.6074 0.031 Uiso 1 1 calc R . . O1 O 0.01375(18) 0.07589(15) 0.65616(19) 0.0267(4) Uani 1 1 d . . . C11 C -0.2410(3) -0.0254(2) 0.8202(3) 0.0325(5) Uani 1 1 d . . . N2 N -0.2899(3) 0.0022(3) 0.9270(3) 0.0475(7) Uani 1 1 d . . . C12 C 0.2785(3) 0.0968(2) 0.9264(3) 0.0275(5) Uani 1 1 d . . . H12A H 0.3773 0.0625 0.9030 0.033 Uiso 1 1 calc R . . H12B H 0.2443 0.1625 0.8542 0.033 Uiso 1 1 calc R . . C13 C 0.4519(3) 0.1969(2) 1.1385(3) 0.0263(5) Uani 1 1 d . . . H13A H 0.4425 0.2716 1.0829 0.032 Uiso 1 1 calc R . . H13B H 0.5454 0.1549 1.1156 0.032 Uiso 1 1 calc R . . C14 C 0.4763(2) 0.2155(2) 1.3137(3) 0.0222(4) Uani 1 1 d . . . C15 C 0.3998(3) 0.1450(2) 1.4040(3) 0.0275(5) Uani 1 1 d . . . H15A H 0.3316 0.0847 1.3539 0.033 Uiso 1 1 calc R . . C16 C 0.4214(3) 0.1614(2) 1.5642(3) 0.0334(6) Uani 1 1 d . . . H16A H 0.3688 0.1120 1.6238 0.040 Uiso 1 1 calc R . . C17 C 0.5192(3) 0.2492(2) 1.6393(3) 0.0316(6) Uani 1 1 d . . . H17A H 0.5334 0.2609 1.7500 0.038 Uiso 1 1 calc R . . C18 C 0.5968(3) 0.3204(2) 1.5505(3) 0.0312(5) Uani 1 1 d . . . H18A H 0.6646 0.3808 1.6011 0.037 Uiso 1 1 calc R . . C19 C 0.5756(2) 0.3036(2) 1.3894(3) 0.0261(5) Uani 1 1 d . . . H19A H 0.6290 0.3524 1.3299 0.031 Uiso 1 1 calc R . . O2 O 0.30856(19) 0.13295(19) 1.0867(2) 0.0359(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0175(7) 0.0213(9) 0.0247(9) -0.0008(7) 0.0073(6) 0.0003(7) C1 0.0168(8) 0.0208(11) 0.0283(10) -0.0022(9) 0.0092(7) 0.0004(8) C2 0.0304(11) 0.0225(12) 0.0390(13) 0.0039(10) 0.0127(9) 0.0009(9) C3 0.0396(12) 0.0312(14) 0.0360(12) 0.0110(11) 0.0128(10) 0.0018(11) C4 0.0317(11) 0.0321(14) 0.0285(12) 0.0035(10) 0.0046(9) 0.0043(10) C5 0.0191(8) 0.0263(12) 0.0247(10) -0.0020(9) 0.0090(7) -0.0006(8) C6 0.0229(9) 0.0297(13) 0.0309(11) -0.0089(10) 0.0098(8) -0.0040(9) C7 0.0346(12) 0.0438(17) 0.0291(12) -0.0043(11) 0.0116(9) -0.0056(11) C8 0.0306(11) 0.0366(15) 0.0329(13) 0.0053(11) 0.0006(9) -0.0037(10) C9 0.0160(8) 0.0284(13) 0.0384(12) 0.0046(10) 0.0040(8) 0.0008(8) C10 0.0155(9) 0.0293(13) 0.0341(11) -0.0011(10) 0.0097(8) 0.0008(8) O1 0.0220(7) 0.0249(9) 0.0328(9) 0.0048(7) 0.0050(6) -0.0021(6) C11 0.0225(9) 0.0333(13) 0.0457(14) -0.0009(12) 0.0160(9) -0.0014(9) N2 0.0368(11) 0.0538(18) 0.0607(16) -0.0074(14) 0.0291(11) 0.0033(12) C12 0.0202(9) 0.0372(14) 0.0272(11) -0.0077(10) 0.0101(8) -0.0074(9) C13 0.0209(9) 0.0300(13) 0.0298(12) -0.0039(10) 0.0098(8) -0.0068(9) C14 0.0176(8) 0.0220(11) 0.0284(11) -0.0014(9) 0.0080(7) 0.0009(8) C15 0.0256(10) 0.0268(13) 0.0315(12) -0.0030(10) 0.0091(8) -0.0049(9) C16 0.0320(12) 0.0380(16) 0.0334(13) 0.0037(11) 0.0141(9) -0.0018(10) C17 0.0307(11) 0.0401(15) 0.0243(11) -0.0058(10) 0.0069(8) 0.0049(10) C18 0.0237(10) 0.0295(13) 0.0379(12) -0.0100(11) 0.0021(8) -0.0011(9) C19 0.0175(9) 0.0250(12) 0.0356(12) 0.0000(10) 0.0061(8) -0.0015(8) O2 0.0228(7) 0.0591(13) 0.0300(9) -0.0163(9) 0.0149(6) -0.0172(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 N1 C5 1.477(3) . ? N1 O1 1.480(2) . ? N1 C1 1.488(3) . ? C1 C2 1.535(3) . ? C1 C6 1.539(3) . ? C1 C10 1.553(3) . ? C2 C3 1.514(4) . ? C3 C4 1.514(4) . ? C4 C5 1.517(3) . ? C5 C12 1.524(3) . ? C6 C7 1.524(4) . ? C7 C8 1.517(4) . ? C8 C9 1.516(4) . ? C9 O1 1.451(3) . ? C9 C10 1.522(4) . ? C10 C11 1.468(3) . ? C11 N2 1.145(3) . ? C12 O2 1.420(3) . ? C13 O2 1.407(3) . ? C13 C14 1.503(3) . ? C14 C19 1.393(3) . ? C14 C15 1.393(3) . ? C15 C16 1.374(3) . ? C16 C17 1.383(4) . ? C17 C18 1.396(4) . ? C18 C19 1.383(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 C5 N1 O1 104.47(16) . . ? C5 N1 C1 115.96(17) . . ? O1 N1 C1 104.56(14) . . ? N1 C1 C2 112.49(17) . . ? N1 C1 C6 108.52(17) . . ? C2 C1 C6 108.8(2) . . ? N1 C1 C10 103.51(17) . . ? C2 C1 C10 117.49(19) . . ? C6 C1 C10 105.52(18) . . ? C3 C2 C1 115.7(2) . . ? C4 C3 C2 109.0(2) . . ? C3 C4 C5 110.90(19) . . ? N1 C5 C4 110.09(19) . . ? N1 C5 C12 108.06(17) . . ? C4 C5 C12 111.18(18) . . ? C7 C6 C1 114.2(2) . . ? C8 C7 C6 112.4(2) . . ? C9 C8 C7 108.9(2) . . ? O1 C9 C8 109.75(19) . . ? O1 C9 C10 104.46(17) . . ? C8 C9 C10 109.5(2) . . ? C11 C10 C9 112.9(2) . . ? C11 C10 C1 117.1(2) . . ? C9 C10 C1 98.84(17) . . ? C9 O1 N1 109.19(16) . . ? N2 C11 C10 176.0(3) . . ? O2 C12 C5 105.75(17) . . ? O2 C13 C14 107.91(18) . . ? C19 C14 C15 118.5(2) . . ? C19 C14 C13 120.7(2) . . ? C15 C14 C13 120.7(2) . . ? C16 C15 C14 121.1(2) . . ? C15 C16 C17 120.4(2) . . ? C16 C17 C18 119.2(2) . . ? C19 C18 C17 120.4(2) . . ? C18 C19 C14 120.4(2) . . ? C13 O2 C12 114.68(17) . . ?