# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_111124a_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H48 N3 Si3 Y' _chemical_formula_weight 575.85 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' Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.1504(16) _cell_length_b 16.584(2) _cell_length_c 17.122(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3166.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 1.973 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.6821 _exptl_absorpt_correction_T_max 0.7178 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27312 _diffrn_reflns_av_R_equivalents 0.0676 _diffrn_reflns_av_sigmaI/netI 0.0788 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.87 _reflns_number_total 7430 _reflns_number_gt 4910 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0442P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.009(6) _refine_ls_number_reflns 7430 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0874 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.0990 _refine_ls_wR_factor_gt 0.0856 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.950 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C14 C 0.5908(3) 0.4987(2) 0.3339(2) 0.0514(10) Uani 1 1 d . . . H14 H 0.6229 0.5445 0.3635 0.062 Uiso 1 1 calc R . . C15 C 0.5284(4) 0.4437(3) 0.3932(2) 0.0750(13) Uani 1 1 d . . . H15A H 0.4917 0.3987 0.3659 0.090 Uiso 1 1 calc R . . H15B H 0.5875 0.4221 0.4291 0.090 Uiso 1 1 calc R . . C16 C 0.4333(4) 0.4887(4) 0.4386(3) 0.105(2) Uani 1 1 d . . . H16A H 0.4710 0.5302 0.4700 0.125 Uiso 1 1 calc R . . H16B H 0.3926 0.4517 0.4735 0.125 Uiso 1 1 calc R . . C17 C 0.3426(4) 0.5271(4) 0.3842(3) 0.113(2) Uani 1 1 d . . . H17A H 0.2976 0.4853 0.3576 0.136 Uiso 1 1 calc R . . H17B H 0.2866 0.5593 0.4143 0.136 Uiso 1 1 calc R . . C18 C 0.4047(3) 0.5803(3) 0.3242(2) 0.0786(14) Uani 1 1 d . . . H18A H 0.4432 0.6250 0.3507 0.094 Uiso 1 1 calc R . . H18B H 0.3453 0.6023 0.2887 0.094 Uiso 1 1 calc R . . C13 C 0.4988(3) 0.5333(2) 0.2773(2) 0.0514(9) Uani 1 1 d . . . H13 H 0.4575 0.4875 0.2530 0.062 Uiso 1 1 calc R . . C19 C 0.6574(4) 0.3988(2) 0.2351(3) 0.0715(12) Uani 1 1 d . . . H19A H 0.6149 0.3575 0.2629 0.107 Uiso 1 1 calc R . . H19B H 0.7272 0.3760 0.2108 0.107 Uiso 1 1 calc R . . H19C H 0.6061 0.4215 0.1958 0.107 Uiso 1 1 calc R . . C20 C 0.7821(3) 0.4281(2) 0.3463(3) 0.0728(13) Uani 1 1 d . . . H20A H 0.7991 0.4668 0.3865 0.109 Uiso 1 1 calc R . . H20B H 0.8548 0.4147 0.3192 0.109 Uiso 1 1 calc R . . H20C H 0.7490 0.3803 0.3694 0.109 Uiso 1 1 calc R . . C11 C 0.3521(4) 0.5252(3) 0.1129(3) 0.0753(13) Uani 1 1 d . . . H11A H 0.3895 0.4732 0.1089 0.113 Uiso 1 1 calc R . . H11B H 0.3130 0.5379 0.0645 0.113 Uiso 1 1 calc R . . H11C H 0.2940 0.5244 0.1542 0.113 Uiso 1 1 calc R . . C12 C 0.3877(4) 0.7006(3) 0.1399(3) 0.0853(15) Uani 1 1 d . . . H12A H 0.3326 0.6994 0.1829 0.128 Uiso 1 1 calc R . . H12B H 0.3444 0.7094 0.0922 0.128 Uiso 1 1 calc R . . H12C H 0.4444 0.7434 0.1475 0.128 Uiso 1 1 calc R . . C10 C 0.5726(4) 0.6074(3) 0.0479(2) 0.0692(12) Uani 1 1 d . . . H10A H 0.5495 0.5655 0.0113 0.083 Uiso 1 1 calc R . . H10B H 0.5617 0.6589 0.0219 0.083 Uiso 1 1 calc R . . C1 C 0.7029(3) 0.5975(3) 0.0667(2) 0.0545(10) Uani 1 1 d . . . C2 C 0.7626(5) 0.5243(3) 0.0768(2) 0.0673(11) Uani 1 1 d . . . H2 H 0.7286 0.4737 0.0694 0.081 Uiso 1 1 calc R . . C3 C 0.8817(4) 0.5384(4) 0.0999(2) 0.0783(15) Uani 1 1 d . . . H3 H 0.9384 0.4992 0.1123 0.094 Uiso 1 1 calc R . . C4 C 0.8997(4) 0.6215(4) 0.1011(2) 0.0722(14) Uani 1 1 d . . . C9 C 1.0002(5) 0.6720(6) 0.1151(3) 0.118(3) Uani 1 1 d . . . H9 H 1.0746 0.6494 0.1260 0.142 Uiso 1 1 calc R . . C8 C 0.9878(9) 0.7517(6) 0.1126(4) 0.144(4) Uani 1 1 d . . . H8 H 1.0545 0.7839 0.1223 0.172 Uiso 1 1 calc R . . C7 C 0.8771(9) 0.7893(5) 0.0958(4) 0.133(3) Uani 1 1 d . . . H7 H 0.8718 0.8453 0.0947 0.160 Uiso 1 1 calc R . . C6 C 0.7771(6) 0.7432(3) 0.0813(3) 0.0934(18) Uani 1 1 d . . . H6 H 0.7037 0.7676 0.0707 0.112 Uiso 1 1 calc R . . C5 C 0.7871(4) 0.6589(3) 0.0825(2) 0.0642(13) Uani 1 1 d . . . C24 C 0.6396(5) 0.7791(3) 0.2902(4) 0.111(2) Uani 1 1 d . . . H24A H 0.6729 0.7973 0.2416 0.166 Uiso 1 1 calc R . . H24B H 0.5977 0.8227 0.3149 0.166 Uiso 1 1 calc R . . H24C H 0.5849 0.7355 0.2805 0.166 Uiso 1 1 calc R . . C25 C 0.6903(7) 0.7143(5) 0.4505(4) 0.183(4) Uani 1 1 d . . . H25A H 0.6363 0.6701 0.4421 0.274 Uiso 1 1 calc R . . H25B H 0.6468 0.7594 0.4712 0.274 Uiso 1 1 calc R . . H25C H 0.7514 0.6984 0.4868 0.274 Uiso 1 1 calc R . . C26 C 0.8564(6) 0.8324(4) 0.3787(5) 0.195(5) Uani 1 1 d . . . H26A H 0.9236 0.8154 0.4096 0.293 Uiso 1 1 calc R . . H26B H 0.8098 0.8709 0.4076 0.293 Uiso 1 1 calc R . . H26C H 0.8846 0.8567 0.3313 0.293 Uiso 1 1 calc R . . C21 C 0.9865(4) 0.6155(3) 0.4487(3) 0.0835(15) Uani 1 1 d . . . H21A H 0.9648 0.6622 0.4787 0.125 Uiso 1 1 calc R . . H21B H 1.0669 0.5996 0.4616 0.125 Uiso 1 1 calc R . . H21C H 0.9323 0.5721 0.4605 0.125 Uiso 1 1 calc R . . C22 C 1.0959(4) 0.7177(3) 0.3237(3) 0.0826(15) Uani 1 1 d . . . H22A H 1.0975 0.7310 0.2691 0.124 Uiso 1 1 calc R . . H22B H 1.1726 0.6967 0.3390 0.124 Uiso 1 1 calc R . . H22C H 1.0784 0.7653 0.3535 0.124 Uiso 1 1 calc R . . C23 C 1.0305(4) 0.5470(3) 0.2875(3) 0.0761(13) Uani 1 1 d . . . H23A H 0.9777 0.5027 0.2986 0.114 Uiso 1 1 calc R . . H23B H 1.1103 0.5336 0.3039 0.114 Uiso 1 1 calc R . . H23C H 1.0302 0.5576 0.2323 0.114 Uiso 1 1 calc R . . N2 N 0.6945(3) 0.46282(17) 0.29030(18) 0.0499(8) Uani 1 1 d . . . N1 N 0.5543(2) 0.58006(16) 0.21392(16) 0.0434(7) Uani 1 1 d . . . N3 N 0.8357(3) 0.66492(17) 0.31300(17) 0.0476(8) Uani 1 1 d . . . Si1 Si 0.46841(9) 0.60304(6) 0.13423(6) 0.0470(3) Uani 1 1 d . . . Si2 Si 0.76191(16) 0.74380(8) 0.35479(9) 0.0894(5) Uani 1 1 d . . . Si3 Si 0.97743(10) 0.63998(7) 0.34194(7) 0.0531(3) Uani 1 1 d . . . Y1 Y 0.75222(3) 0.587083(18) 0.220183(16) 0.04184(10) 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 C14 0.044(2) 0.062(2) 0.048(2) 0.011(2) -0.0061(18) 0.0012(19) C15 0.063(3) 0.102(4) 0.060(3) 0.033(2) -0.004(2) -0.002(3) C16 0.063(3) 0.185(6) 0.066(3) 0.051(3) 0.013(3) 0.022(4) C17 0.060(3) 0.203(7) 0.077(4) 0.052(4) 0.016(3) 0.032(4) C18 0.050(2) 0.128(4) 0.058(3) 0.013(3) 0.005(2) 0.029(3) C13 0.039(2) 0.067(2) 0.049(2) 0.010(2) -0.0087(19) 0.0013(18) C19 0.080(3) 0.051(2) 0.084(3) 0.001(2) 0.004(3) 0.000(2) C20 0.052(3) 0.074(3) 0.092(3) 0.026(3) -0.011(2) 0.008(2) C11 0.074(3) 0.084(3) 0.068(3) -0.002(2) -0.015(2) -0.014(3) C12 0.101(4) 0.079(3) 0.076(3) 0.001(3) -0.020(3) 0.032(3) C10 0.076(3) 0.085(3) 0.047(2) 0.004(2) -0.010(2) 0.002(3) C1 0.057(2) 0.072(3) 0.0341(19) -0.002(2) 0.0032(16) 0.000(2) C2 0.073(3) 0.084(3) 0.044(2) -0.018(2) 0.003(3) 0.001(3) C3 0.068(3) 0.118(5) 0.049(3) -0.007(3) 0.008(2) 0.018(3) C4 0.055(3) 0.121(5) 0.041(2) 0.002(3) 0.009(2) -0.023(3) C9 0.084(4) 0.220(9) 0.051(3) 0.023(4) 0.002(3) -0.062(5) C8 0.192(9) 0.166(9) 0.072(4) 0.023(5) 0.004(5) -0.126(8) C7 0.215(9) 0.106(5) 0.078(4) 0.028(4) 0.009(5) -0.078(7) C6 0.133(5) 0.087(3) 0.060(3) 0.022(3) 0.017(3) -0.021(4) C5 0.081(4) 0.075(3) 0.037(2) 0.003(2) 0.011(2) -0.021(3) C24 0.099(4) 0.087(4) 0.147(5) -0.038(4) -0.048(4) 0.038(3) C25 0.175(7) 0.281(11) 0.091(5) -0.080(6) 0.008(5) 0.101(7) C26 0.140(6) 0.085(4) 0.360(13) -0.107(6) -0.117(8) 0.037(4) C21 0.081(3) 0.097(4) 0.072(3) 0.017(3) -0.027(3) -0.002(3) C22 0.062(3) 0.103(4) 0.083(4) 0.001(3) -0.003(3) -0.028(3) C23 0.049(2) 0.091(3) 0.088(3) -0.010(3) -0.002(3) 0.007(2) N2 0.0443(16) 0.0416(16) 0.064(2) 0.0041(16) -0.0035(15) 0.0021(13) N1 0.0424(15) 0.0434(16) 0.0443(16) 0.0021(15) -0.0019(13) 0.0018(13) N3 0.0436(18) 0.0462(18) 0.0531(18) -0.0015(14) -0.0081(15) 0.0004(14) Si1 0.0467(6) 0.0477(6) 0.0464(6) 0.0002(5) -0.0089(5) 0.0050(5) Si2 0.0795(9) 0.0785(8) 0.1102(11) -0.0504(8) -0.0394(10) 0.0296(9) Si3 0.0428(6) 0.0604(7) 0.0562(6) 0.0047(6) -0.0088(5) -0.0044(5) Y1 0.04113(16) 0.04778(17) 0.03662(15) -0.00085(15) -0.0005(2) -0.0027(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 C14 N2 1.500(5) . ? C14 C13 1.524(5) . ? C14 C15 1.532(5) . ? C14 H14 0.9800 . ? C15 C16 1.512(7) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.516(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.520(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C13 1.534(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C13 N1 1.470(4) . ? C13 H13 0.9800 . ? C19 N2 1.480(5) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 N2 1.485(5) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C11 Si1 1.866(4) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 Si1 1.854(4) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C10 C1 1.497(5) . ? C10 Si1 1.881(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C1 C2 1.395(6) . ? C1 C5 1.412(5) . ? C1 Y1 2.691(3) . ? C2 C3 1.406(7) . ? C2 Y1 2.669(4) . ? C2 H2 0.9300 . ? C3 C4 1.393(7) . ? C3 Y1 2.641(4) . ? C3 H3 0.9300 . ? C4 C9 1.420(8) . ? C4 C5 1.436(6) . ? C4 Y1 2.681(4) . ? C9 C8 1.329(10) . ? C9 H9 0.9300 . ? C8 C7 1.413(11) . ? C8 H8 0.9300 . ? C7 C6 1.375(9) . ? C7 H7 0.9300 . ? C6 C5 1.402(7) . ? C6 H6 0.9300 . ? C5 Y1 2.670(4) . ? C24 Si2 1.851(5) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 Si2 1.887(8) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 Si2 1.853(6) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C21 Si3 1.875(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 Si3 1.872(4) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 Si3 1.897(5) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? N2 Y1 2.470(3) . ? N1 Si1 1.710(3) . ? N1 Y1 2.212(3) . ? N3 Si2 1.703(3) . ? N3 Si3 1.707(3) . ? N3 Y1 2.249(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 N2 C14 C13 110.6(3) . . ? N2 C14 C15 116.3(3) . . ? C13 C14 C15 109.9(3) . . ? N2 C14 H14 106.5 . . ? C13 C14 H14 106.5 . . ? C15 C14 H14 106.5 . . ? C16 C15 C14 111.4(4) . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15B 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C15 C16 C17 111.1(4) . . ? C15 C16 H16A 109.4 . . ? C17 C16 H16A 109.4 . . ? C15 C16 H16B 109.4 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C18 C17 C16 110.8(4) . . ? C18 C17 H17A 109.5 . . ? C16 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C17 C18 C13 111.7(4) . . ? C17 C18 H18A 109.3 . . ? C13 C18 H18A 109.3 . . ? C17 C18 H18B 109.3 . . ? C13 C18 H18B 109.3 . . ? H18A C18 H18B 107.9 . . ? N1 C13 C14 112.6(3) . . ? N1 C13 C18 114.0(3) . . ? C14 C13 C18 108.6(3) . . ? N1 C13 H13 107.1 . . ? C14 C13 H13 107.1 . . ? C18 C13 H13 107.1 . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N2 C20 H20A 109.5 . . ? N2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? Si1 C11 H11A 109.5 . . ? Si1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? Si1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? Si1 C12 H12A 109.5 . . ? Si1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? Si1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C1 C10 Si1 115.2(3) . . ? C1 C10 H10A 108.5 . . ? Si1 C10 H10A 108.5 . . ? C1 C10 H10B 108.5 . . ? Si1 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? C2 C1 C5 106.6(4) . . ? C2 C1 C10 125.9(4) . . ? C5 C1 C10 127.4(4) . . ? C2 C1 Y1 74.0(2) . . ? C5 C1 Y1 73.9(2) . . ? C10 C1 Y1 114.5(2) . . ? C3 C2 C1 110.0(4) . . ? C3 C2 Y1 73.6(2) . . ? C1 C2 Y1 75.8(2) . . ? C3 C2 H2 125.0 . . ? C1 C2 H2 125.0 . . ? Y1 C2 H2 117.4 . . ? C4 C3 C2 107.7(5) . . ? C4 C3 Y1 76.4(3) . . ? C2 C3 Y1 75.7(2) . . ? C4 C3 H3 126.2 . . ? C2 C3 H3 126.2 . . ? Y1 C3 H3 114.1 . . ? C3 C4 C9 134.4(6) . . ? C3 C4 C5 107.4(4) . . ? C9 C4 C5 118.2(6) . . ? C3 C4 Y1 73.3(3) . . ? C9 C4 Y1 118.7(3) . . ? C5 C4 Y1 74.0(2) . . ? C8 C9 C4 120.0(7) . . ? C8 C9 H9 120.0 . . ? C4 C9 H9 120.0 . . ? C9 C8 C7 122.4(8) . . ? C9 C8 H8 118.8 . . ? C7 C8 H8 118.8 . . ? C6 C7 C8 120.0(7) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C6 C5 119.1(6) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C5 C1 131.5(5) . . ? C6 C5 C4 120.3(5) . . ? C1 C5 C4 108.2(4) . . ? C6 C5 Y1 116.5(3) . . ? C1 C5 Y1 75.6(2) . . ? C4 C5 Y1 74.9(2) . . ? Si2 C24 H24A 109.5 . . ? Si2 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? Si2 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? Si2 C25 H25A 109.5 . . ? Si2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? Si2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? Si2 C26 H26A 109.5 . . ? Si2 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? Si2 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? Si3 C21 H21A 109.5 . . ? Si3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? Si3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? Si3 C22 H22A 109.5 . . ? Si3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? Si3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? Si3 C23 H23A 109.5 . . ? Si3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? Si3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C19 N2 C20 108.5(3) . . ? C19 N2 C14 112.8(3) . . ? C20 N2 C14 109.9(3) . . ? C19 N2 Y1 111.1(2) . . ? C20 N2 Y1 117.8(2) . . ? C14 N2 Y1 96.40(19) . . ? C13 N1 Si1 118.0(2) . . ? C13 N1 Y1 114.35(19) . . ? Si1 N1 Y1 125.86(15) . . ? Si2 N3 Si3 120.75(18) . . ? Si2 N3 Y1 122.55(16) . . ? Si3 N3 Y1 116.69(15) . . ? N1 Si1 C12 115.14(19) . . ? N1 Si1 C11 113.05(17) . . ? C12 Si1 C11 106.1(2) . . ? N1 Si1 C10 106.84(16) . . ? C12 Si1 C10 107.9(2) . . ? C11 Si1 C10 107.5(2) . . ? N3 Si2 C26 115.3(3) . . ? N3 Si2 C24 110.3(2) . . ? C26 Si2 C24 107.5(3) . . ? N3 Si2 C25 111.7(3) . . ? C26 Si2 C25 104.7(4) . . ? C24 Si2 C25 106.8(3) . . ? N3 Si3 C21 112.7(2) . . ? N3 Si3 C22 116.0(2) . . ? C21 Si3 C22 105.9(2) . . ? N3 Si3 C23 110.05(18) . . ? C21 Si3 C23 106.7(2) . . ? C22 Si3 C23 104.9(2) . . ? N1 Y1 N3 118.50(11) . . ? N1 Y1 N2 73.74(10) . . ? N3 Y1 N2 104.07(10) . . ? N1 Y1 C3 119.44(14) . . ? N3 Y1 C3 120.01(15) . . ? N2 Y1 C3 105.43(16) . . ? N1 Y1 C2 88.74(14) . . ? N3 Y1 C2 148.86(14) . . ? N2 Y1 C2 97.64(12) . . ? C3 Y1 C2 30.70(15) . . ? N1 Y1 C5 97.24(13) . . ? N3 Y1 C5 107.92(12) . . ? N2 Y1 C5 147.07(12) . . ? C3 Y1 C5 50.84(16) . . ? C2 Y1 C5 49.87(14) . . ? N1 Y1 C4 125.87(13) . . ? N3 Y1 C4 99.30(14) . . ? N2 Y1 C4 134.98(16) . . ? C3 Y1 C4 30.33(15) . . ? C2 Y1 C4 49.97(15) . . ? C5 Y1 C4 31.13(14) . . ? N1 Y1 C1 75.64(11) . . ? N3 Y1 C1 137.57(12) . . ? N2 Y1 C1 118.35(12) . . ? C3 Y1 C1 50.95(13) . . ? C2 Y1 C1 30.16(12) . . ? C5 Y1 C1 30.54(12) . . ? C4 Y1 C1 50.86(13) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.703 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 960598' ####################################################################### # # 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_121108b_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(4-bromobenzoyl)-2-methyl-4,4-diphenylpyrrolidine ; _chemical_absolute_configuration R _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 Br N O' _chemical_formula_weight 420.34 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.3286(12) _cell_length_b 11.6063(13) _cell_length_c 16.6657(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1997.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 2.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.714049 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17894 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0485 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 29.06 _reflns_number_total 4936 _reflns_number_gt 3367 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1367P)^2^+0.6106P] 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 -0.004(13) _refine_ls_number_reflns 4936 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0808 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1775 _refine_ls_wR_factor_gt 0.1500 _refine_ls_goodness_of_fit_ref 0.835 _refine_ls_restrained_S_all 0.835 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.16694(6) -0.22980(7) 0.14296(4) 0.0983(3) Uani 1 1 d . . . N1 N 0.7637(3) 0.0532(2) 0.12528(18) 0.0409(7) Uani 1 1 d . . . C11 C 0.8057(4) 0.3101(3) -0.0670(2) 0.0473(8) Uani 1 1 d . . . H11 H 0.8410 0.3770 -0.0455 0.057 Uiso 1 1 calc R . . C22 C 0.3346(4) -0.1654(3) 0.1291(2) 0.0516(9) Uani 1 1 d . . . C18 C 0.7241(4) -0.0554(3) 0.1096(2) 0.0445(8) Uani 1 1 d . . . C2 C 0.7658(3) 0.2444(3) 0.07492(19) 0.0364(7) Uani 1 1 d . . . O1 O 0.8012(3) -0.1328(2) 0.0942(2) 0.0623(8) Uani 1 1 d . . . C1 C 0.6833(3) 0.1567(3) 0.1226(2) 0.0393(7) Uani 1 1 d . . . H1A H 0.6654 0.1848 0.1763 0.047 Uiso 1 1 calc R . . H1B H 0.6019 0.1415 0.0956 0.047 Uiso 1 1 calc R . . C6 C 0.7601(3) 0.2258(3) -0.0162(2) 0.0387(7) Uani 1 1 d . . . C3 C 0.9020(3) 0.2119(3) 0.1073(2) 0.0440(8) Uani 1 1 d . . . H3A H 0.9686 0.2354 0.0697 0.053 Uiso 1 1 calc R . . H3B H 0.9180 0.2493 0.1584 0.053 Uiso 1 1 calc R . . C20 C 0.5092(4) -0.0609(3) 0.1832(2) 0.0466(8) Uani 1 1 d . . . H20 H 0.5444 -0.0162 0.2241 0.056 Uiso 1 1 calc R . . C4 C 0.9022(4) 0.0818(3) 0.1173(2) 0.0451(8) Uani 1 1 d . . . H4 H 0.9365 0.0461 0.0684 0.054 Uiso 1 1 calc R . . C19 C 0.5825(4) -0.0829(3) 0.1151(2) 0.0415(8) Uani 1 1 d . . . C10 C 0.8003(5) 0.2973(4) -0.1504(2) 0.0600(10) Uani 1 1 d . . . H10 H 0.8285 0.3566 -0.1835 0.072 Uiso 1 1 calc R . . C12 C 0.7266(4) 0.3675(3) 0.0943(2) 0.0394(7) Uani 1 1 d . . . C13 C 0.5983(4) 0.3997(3) 0.0879(2) 0.0455(8) Uani 1 1 d . . . H13 H 0.5371 0.3454 0.0721 0.055 Uiso 1 1 calc R . . C8 C 0.7085(5) 0.1125(4) -0.1345(3) 0.0601(10) Uani 1 1 d . . . H8 H 0.6751 0.0451 -0.1566 0.072 Uiso 1 1 calc R . . C21 C 0.3856(4) -0.1036(3) 0.1916(2) 0.0518(9) Uani 1 1 d . . . H21 H 0.3382 -0.0910 0.2382 0.062 Uiso 1 1 calc R . . C16 C 0.7767(5) 0.5633(4) 0.1323(3) 0.0587(11) Uani 1 1 d . . . H16 H 0.8376 0.6185 0.1470 0.070 Uiso 1 1 calc R . . C15 C 0.6497(5) 0.5933(3) 0.1268(3) 0.0594(11) Uani 1 1 d . . . H15 H 0.6240 0.6685 0.1380 0.071 Uiso 1 1 calc R . . C17 C 0.8167(4) 0.4508(3) 0.1163(2) 0.0486(9) Uani 1 1 d . . . H17 H 0.9038 0.4314 0.1203 0.058 Uiso 1 1 calc R . . C24 C 0.5256(4) -0.1458(4) 0.0535(2) 0.0513(9) Uani 1 1 d . . . H24 H 0.5730 -0.1610 0.0072 0.062 Uiso 1 1 calc R . . C9 C 0.7533(5) 0.1970(4) -0.1835(2) 0.0601(11) Uani 1 1 d . . . H9 H 0.7522 0.1872 -0.2389 0.072 Uiso 1 1 calc R . . C14 C 0.5587(5) 0.5118(4) 0.1045(3) 0.0553(10) Uani 1 1 d . . . H14 H 0.4717 0.5318 0.1007 0.066 Uiso 1 1 calc R . . C5 C 0.9809(5) 0.0417(4) 0.1889(3) 0.0676(13) Uani 1 1 d . . . H5A H 0.9469 0.0759 0.2369 0.101 Uiso 1 1 calc R . . H5B H 1.0696 0.0646 0.1821 0.101 Uiso 1 1 calc R . . H5C H 0.9761 -0.0407 0.1930 0.101 Uiso 1 1 calc R . . C23 C 0.4012(4) -0.1858(4) 0.0595(2) 0.0557(10) Uani 1 1 d . . . H23 H 0.3630 -0.2260 0.0174 0.067 Uiso 1 1 calc R . . C7 C 0.7120(4) 0.1259(4) -0.0508(2) 0.0513(9) Uani 1 1 d . . . H7 H 0.6817 0.0669 -0.0181 0.062 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 Br1 0.0714(3) 0.1255(6) 0.0981(4) -0.0400(4) 0.0159(3) -0.0442(4) N1 0.0414(15) 0.0319(14) 0.0495(17) 0.0048(12) 0.0016(12) 0.0047(12) C11 0.051(2) 0.0449(19) 0.0456(19) 0.0006(15) 0.0046(15) -0.0030(16) C22 0.056(2) 0.0384(18) 0.060(2) -0.0019(16) -0.0030(19) -0.0074(17) C18 0.055(2) 0.0326(17) 0.0463(18) 0.0027(15) 0.0065(16) 0.0072(16) C2 0.0351(15) 0.0341(16) 0.0399(15) -0.0031(14) -0.0011(12) -0.0018(13) O1 0.0597(17) 0.0413(14) 0.086(2) -0.0083(14) 0.0124(15) 0.0101(13) C1 0.0395(17) 0.0310(15) 0.0473(18) 0.0009(13) 0.0041(13) 0.0047(13) C6 0.0362(16) 0.0363(17) 0.0437(17) 0.0021(14) 0.0040(13) 0.0036(13) C3 0.0377(17) 0.0453(19) 0.0491(18) 0.0003(16) -0.0022(14) -0.0006(15) C20 0.060(2) 0.042(2) 0.0370(17) -0.0024(15) 0.0037(16) -0.0063(17) C4 0.0410(18) 0.0405(18) 0.054(2) 0.0083(16) 0.0046(15) 0.0038(15) C19 0.053(2) 0.0265(15) 0.0450(18) 0.0014(14) 0.0022(16) 0.0037(15) C10 0.075(3) 0.059(3) 0.046(2) 0.0060(19) 0.0111(19) 0.001(2) C12 0.0479(19) 0.0334(16) 0.0370(16) 0.0025(13) -0.0004(14) -0.0034(14) C13 0.055(2) 0.0324(18) 0.049(2) -0.0028(14) -0.0054(16) 0.0001(16) C8 0.075(3) 0.052(2) 0.054(2) -0.0132(19) -0.012(2) 0.001(2) C21 0.060(2) 0.052(2) 0.0426(19) -0.0078(17) 0.0078(17) -0.0071(19) C16 0.081(3) 0.0376(19) 0.058(2) -0.0069(18) -0.006(2) -0.012(2) C15 0.089(3) 0.0307(18) 0.058(2) 0.0012(16) -0.009(2) 0.0037(19) C17 0.055(2) 0.0368(17) 0.054(2) -0.0044(16) -0.0012(17) -0.0133(16) C24 0.066(2) 0.046(2) 0.0426(19) -0.0101(17) 0.0070(17) 0.0002(18) C9 0.072(3) 0.068(3) 0.0395(19) -0.0050(19) 0.0045(18) 0.015(2) C14 0.066(3) 0.041(2) 0.059(2) 0.0001(18) -0.011(2) 0.0119(19) C5 0.055(2) 0.062(3) 0.086(3) 0.021(3) -0.013(2) 0.002(2) C23 0.066(3) 0.054(2) 0.047(2) -0.0098(18) -0.0030(18) -0.002(2) C7 0.061(2) 0.0438(19) 0.049(2) -0.0009(17) -0.0024(17) -0.0052(18) _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 Br1 C22 1.900(4) . ? N1 C18 1.351(5) . ? N1 C4 1.475(5) . ? N1 C1 1.461(4) . ? C11 C6 1.378(5) . ? C11 C10 1.398(5) . ? C11 H11 0.9300 . ? C22 C23 1.369(6) . ? C22 C21 1.369(5) . ? C18 O1 1.227(5) . ? C18 C19 1.500(6) . ? C2 C12 1.520(5) . ? C2 C6 1.534(5) . ? C2 C1 1.547(5) . ? C2 C3 1.553(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C6 C7 1.387(5) . ? C3 C4 1.519(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C20 C21 1.377(6) . ? C20 C19 1.388(5) . ? C20 H20 0.9300 . ? C4 C5 1.517(6) . ? C4 H4 0.9800 . ? C19 C24 1.390(6) . ? C10 C9 1.377(7) . ? C10 H10 0.9300 . ? C12 C13 1.382(5) . ? C12 C17 1.390(5) . ? C13 C14 1.392(5) . ? C13 H13 0.9300 . ? C8 C9 1.358(7) . ? C8 C7 1.405(6) . ? C8 H8 0.9300 . ? C21 H21 0.9300 . ? C16 C15 1.361(7) . ? C16 C17 1.396(6) . ? C16 H16 0.9300 . ? C15 C14 1.384(6) . ? C15 H15 0.9300 . ? C17 H17 0.9300 . ? C24 C23 1.370(6) . ? C24 H24 0.9300 . ? C9 H9 0.9300 . ? C14 H14 0.9300 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C23 H23 0.9300 . ? C7 H7 0.9300 . ? 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 C18 N1 C4 119.1(3) . . ? C18 N1 C1 126.1(3) . . ? C4 N1 C1 111.3(3) . . ? C6 C11 C10 121.4(4) . . ? C6 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C23 C22 C21 122.7(4) . . ? C23 C22 Br1 119.5(3) . . ? C21 C22 Br1 117.7(3) . . ? O1 C18 N1 121.8(4) . . ? O1 C18 C19 119.3(4) . . ? N1 C18 C19 118.8(3) . . ? C12 C2 C6 109.4(3) . . ? C12 C2 C1 111.2(3) . . ? C6 C2 C1 113.2(3) . . ? C12 C2 C3 113.3(3) . . ? C6 C2 C3 110.2(3) . . ? C1 C2 C3 99.2(3) . . ? N1 C1 C2 104.1(3) . . ? N1 C1 H1A 110.9 . . ? C2 C1 H1A 110.9 . . ? N1 C1 H1B 110.9 . . ? C2 C1 H1B 110.9 . . ? H1A C1 H1B 109.0 . . ? C11 C6 C7 117.4(3) . . ? C11 C6 C2 119.7(3) . . ? C7 C6 C2 122.9(3) . . ? C4 C3 C2 106.3(3) . . ? C4 C3 H3A 110.5 . . ? C2 C3 H3A 110.5 . . ? C4 C3 H3B 110.5 . . ? C2 C3 H3B 110.5 . . ? H3A C3 H3B 108.7 . . ? C21 C20 C19 121.5(3) . . ? C21 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? N1 C4 C3 103.4(3) . . ? N1 C4 C5 112.3(3) . . ? C3 C4 C5 113.1(4) . . ? N1 C4 H4 109.3 . . ? C3 C4 H4 109.3 . . ? C5 C4 H4 109.3 . . ? C24 C19 C20 118.0(4) . . ? C24 C19 C18 118.6(3) . . ? C20 C19 C18 122.9(3) . . ? C9 C10 C11 120.2(4) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C13 C12 C17 118.3(4) . . ? C13 C12 C2 119.5(3) . . ? C17 C12 C2 122.1(3) . . ? C12 C13 C14 121.3(4) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C9 C8 C7 120.6(4) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C22 C21 C20 117.9(4) . . ? C22 C21 H21 121.0 . . ? C20 C21 H21 121.0 . . ? C15 C16 C17 120.8(4) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C16 C15 C14 119.9(4) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C12 C17 C16 120.2(4) . . ? C12 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C19 C24 C23 121.3(4) . . ? C19 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C10 C9 C8 119.3(4) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C13 C14 C15 119.5(4) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C22 C23 C24 118.4(4) . . ? C22 C23 H23 120.8 . . ? C24 C23 H23 120.8 . . ? C6 C7 C8 121.0(4) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 29.06 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.969 _refine_diff_density_min -0.929 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 960599' ####################################################################### # # 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_130110a_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(4-bromobenzoyl)-2-methyl-5,5-diphenypiperidine ; _chemical_absolute_configuration R _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H24 Br N O' _chemical_formula_weight 434.36 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.7847(9) _cell_length_b 12.8744(12) _cell_length_c 9.3892(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.2710(10) _cell_angle_gamma 90.00 _cell_volume 1057.41(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 1.958 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.767053 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8880 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.41 _reflns_number_total 4636 _reflns_number_gt 4145 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0824P)^2^+0.0000P] 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 0.018(7) _refine_ls_number_reflns 4636 _refine_ls_number_parameters 254 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0784 _refine_ls_wR_factor_gt 0.0735 _refine_ls_goodness_of_fit_ref 0.656 _refine_ls_restrained_S_all 0.656 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br -0.51513(2) 0.43688(3) 0.85296(2) 0.05919(9) Uani 1 1 d . . . C23 C -0.3963(2) 0.55977(16) 0.8503(2) 0.0400(4) Uani 1 1 d . . . O1 O -0.1478(2) 0.90696(12) 0.8836(2) 0.0589(4) Uani 1 1 d . . . N1 N 0.04498(18) 0.80370(12) 0.82202(18) 0.0392(3) Uani 1 1 d . . . C1 C 0.1455(2) 0.89258(15) 0.8085(2) 0.0376(4) Uani 1 1 d . . . H1A H 0.2199 0.8956 0.8914 0.045 Uiso 1 1 calc R . . H1B H 0.0856 0.9559 0.8063 0.045 Uiso 1 1 calc R . . C21 C -0.2591(3) 0.6940(2) 0.9792(2) 0.0497(5) Uani 1 1 d . . . H21 H -0.2315 0.7283 1.0648 0.060 Uiso 1 1 calc R . . C19 C -0.1001(2) 0.82080(16) 0.8563(2) 0.0405(4) Uani 1 1 d . . . C25 C -0.2546(3) 0.6811(2) 0.7263(2) 0.0491(5) Uani 1 1 d . . . H25 H -0.2225 0.7063 0.6412 0.059 Uiso 1 1 calc R . . C2 C 0.2301(2) 0.88607(14) 0.6718(2) 0.0353(3) Uani 1 1 d . . . C22 C -0.3539(3) 0.60861(18) 0.9777(2) 0.0483(5) Uani 1 1 d . . . H22 H -0.3888 0.5844 1.0621 0.058 Uiso 1 1 calc R . . C13 C 0.3369(2) 0.98002(15) 0.67210(19) 0.0359(4) Uani 1 1 d . . . C6 C 0.2093(4) 0.6782(2) 0.9655(3) 0.0619(6) Uani 1 1 d . . . H6A H 0.2939 0.7255 0.9772 0.093 Uiso 1 1 calc R . . H6B H 0.2469 0.6081 0.9662 0.093 Uiso 1 1 calc R . . H6C H 0.1457 0.6873 1.0424 0.093 Uiso 1 1 calc R . . C7 C 0.1214(2) 0.89044(14) 0.5338(2) 0.0374(4) Uani 1 1 d . . . C15 C 0.3669(3) 1.16659(16) 0.6554(2) 0.0513(5) Uani 1 1 d . . . H15 H 0.3231 1.2319 0.6408 0.062 Uiso 1 1 calc R . . C4 C 0.2104(3) 0.69101(16) 0.6937(3) 0.0470(5) Uani 1 1 d . . . H4A H 0.2697 0.6274 0.7019 0.056 Uiso 1 1 calc R . . H4B H 0.1417 0.6865 0.6069 0.056 Uiso 1 1 calc R . . C8 C -0.0324(2) 0.91586(15) 0.5319(2) 0.0447(5) Uani 1 1 d . . . H8 H -0.0750 0.9276 0.6176 0.054 Uiso 1 1 calc R . . C14 C 0.2745(3) 1.07885(17) 0.6502(2) 0.0420(4) Uani 1 1 d . . . H14 H 0.1692 1.0862 0.6319 0.050 Uiso 1 1 calc R . . C20 C -0.2048(2) 0.72887(16) 0.8546(2) 0.0385(4) Uani 1 1 d . . . C3 C 0.3179(2) 0.78203(16) 0.6812(3) 0.0431(4) Uani 1 1 d . . . H3A H 0.3720 0.7735 0.5964 0.052 Uiso 1 1 calc R . . H3B H 0.3929 0.7832 0.7637 0.052 Uiso 1 1 calc R . . C12 C 0.1809(3) 0.8755(2) 0.4027(2) 0.0523(5) Uani 1 1 d . . . H12 H 0.2840 0.8596 0.4009 0.063 Uiso 1 1 calc R . . C18 C 0.4955(2) 0.97225(18) 0.6978(3) 0.0489(5) Uani 1 1 d . . . H18 H 0.5406 0.9073 0.7124 0.059 Uiso 1 1 calc R . . C17 C 0.5867(3) 1.0605(2) 0.7017(3) 0.0587(6) Uani 1 1 d . . . H17 H 0.6923 1.0540 0.7180 0.070 Uiso 1 1 calc R . . C5 C 0.1155(2) 0.69975(15) 0.8227(2) 0.0447(4) Uani 1 1 d . . . H5 H 0.0332 0.6482 0.8108 0.054 Uiso 1 1 calc R . . C16 C 0.5222(3) 1.1573(2) 0.6817(3) 0.0579(6) Uani 1 1 d . . . H16 H 0.5838 1.2162 0.6861 0.070 Uiso 1 1 calc R . . C11 C 0.0890(3) 0.8837(2) 0.2751(3) 0.0634(6) Uani 1 1 d . . . H11 H 0.1304 0.8729 0.1887 0.076 Uiso 1 1 calc R . . C9 C -0.1235(3) 0.9239(2) 0.4028(3) 0.0555(5) Uani 1 1 d . . . H9 H -0.2265 0.9404 0.4035 0.067 Uiso 1 1 calc R . . C24 C -0.3514(3) 0.59625(19) 0.7234(2) 0.0495(5) Uani 1 1 d . . . H24 H -0.3854 0.5646 0.6373 0.059 Uiso 1 1 calc R . . C10 C -0.0641(3) 0.90802(19) 0.2760(3) 0.0611(6) Uani 1 1 d . . . H10 H -0.1261 0.9135 0.1905 0.073 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 Br1 0.04963(12) 0.05274(12) 0.07393(15) 0.00041(12) -0.00115(9) -0.01414(11) C23 0.0332(8) 0.0403(9) 0.0458(10) 0.0012(8) 0.0005(7) -0.0010(7) O1 0.0554(9) 0.0444(9) 0.0808(11) -0.0074(7) 0.0266(8) 0.0028(6) N1 0.0371(8) 0.0327(8) 0.0481(9) 0.0036(7) 0.0059(6) 0.0016(6) C1 0.0398(9) 0.0303(8) 0.0429(10) -0.0006(7) 0.0041(7) -0.0012(7) C21 0.0610(14) 0.0546(12) 0.0339(10) -0.0024(9) 0.0059(9) -0.0133(11) C19 0.0432(10) 0.0420(10) 0.0371(9) -0.0007(8) 0.0080(8) 0.0006(8) C25 0.0546(12) 0.0620(13) 0.0318(9) 0.0034(9) 0.0092(8) -0.0107(11) C2 0.0344(8) 0.0307(8) 0.0408(9) -0.0019(7) 0.0038(7) 0.0018(7) C22 0.0564(12) 0.0527(12) 0.0368(10) 0.0033(9) 0.0094(8) -0.0097(10) C13 0.0411(9) 0.0359(8) 0.0311(8) -0.0027(7) 0.0057(7) -0.0013(7) C6 0.0675(16) 0.0508(13) 0.0668(16) 0.0169(12) 0.0028(13) 0.0143(12) C7 0.0399(9) 0.0311(8) 0.0407(9) -0.0048(7) 0.0009(7) -0.0006(7) C15 0.0803(16) 0.0372(10) 0.0364(10) 0.0025(8) 0.0051(10) -0.0088(10) C4 0.0477(11) 0.0308(9) 0.0625(13) -0.0042(9) 0.0048(9) 0.0068(8) C8 0.0409(9) 0.0431(13) 0.0493(10) 0.0063(8) 0.0006(7) 0.0024(7) C14 0.0510(12) 0.0391(10) 0.0350(9) 0.0015(8) -0.0001(8) -0.0024(8) C20 0.0385(9) 0.0422(9) 0.0352(9) 0.0028(8) 0.0062(7) 0.0007(8) C3 0.0381(10) 0.0370(10) 0.0543(12) -0.0011(9) 0.0046(8) 0.0056(8) C12 0.0541(12) 0.0558(13) 0.0468(11) -0.0121(10) 0.0039(9) 0.0022(10) C18 0.0414(10) 0.0486(11) 0.0576(12) -0.0061(9) 0.0104(8) -0.0023(8) C17 0.0463(12) 0.0613(14) 0.0700(15) -0.0081(12) 0.0125(10) -0.0126(10) C5 0.0427(10) 0.0301(9) 0.0612(12) 0.0046(8) 0.0040(9) 0.0009(7) C16 0.0692(16) 0.0521(13) 0.0539(12) -0.0031(10) 0.0133(11) -0.0261(11) C11 0.0801(17) 0.0698(16) 0.0395(11) -0.0139(11) 0.0010(10) -0.0026(13) C9 0.0479(10) 0.0515(14) 0.0642(12) 0.0072(11) -0.0099(9) -0.0014(10) C24 0.0549(12) 0.0576(13) 0.0355(10) -0.0048(9) 0.0018(8) -0.0076(10) C10 0.0681(14) 0.0596(15) 0.0513(12) 0.0003(9) -0.0176(10) -0.0079(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 Br1 C23 1.897(2) . ? C23 C24 1.372(3) . ? C23 C22 1.372(3) . ? O1 C19 1.221(3) . ? N1 C19 1.361(3) . ? N1 C1 1.458(2) . ? N1 C5 1.475(2) . ? C1 C2 1.543(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C21 C22 1.378(3) . ? C21 C20 1.378(3) . ? C21 H21 0.9300 . ? C19 C20 1.498(3) . ? C25 C24 1.382(3) . ? C25 C20 1.388(3) . ? C25 H25 0.9300 . ? C2 C13 1.531(3) . ? C2 C7 1.538(3) . ? C2 C3 1.544(3) . ? C22 H22 0.9300 . ? C13 C14 1.393(3) . ? C13 C18 1.395(3) . ? C6 C5 1.533(4) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C12 1.394(3) . ? C7 C8 1.389(3) . ? C15 C16 1.369(4) . ? C15 C14 1.389(3) . ? C15 H15 0.9300 . ? C4 C3 1.516(3) . ? C4 C5 1.536(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C8 C9 1.393(3) . ? C8 H8 0.9300 . ? C14 H14 0.9300 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C12 C11 1.387(3) . ? C12 H12 0.9300 . ? C18 C17 1.388(3) . ? C18 H18 0.9300 . ? C17 C16 1.375(4) . ? C17 H17 0.9300 . ? C5 H5 0.9800 . ? C16 H16 0.9300 . ? C11 C10 1.382(4) . ? C11 H11 0.9300 . ? C9 C10 1.359(4) . ? C9 H9 0.9300 . ? C24 H24 0.9300 . ? C10 H10 0.9300 . ? 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 C24 C23 C22 121.57(19) . . ? C24 C23 Br1 119.95(15) . . ? C22 C23 Br1 118.45(15) . . ? C19 N1 C1 118.79(15) . . ? C19 N1 C5 123.24(15) . . ? C1 N1 C5 117.06(15) . . ? N1 C1 C2 111.81(15) . . ? N1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? N1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 107.9 . . ? C22 C21 C20 120.5(2) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? O1 C19 N1 122.91(18) . . ? O1 C19 C20 119.84(18) . . ? N1 C19 C20 117.21(16) . . ? C24 C25 C20 120.75(19) . . ? C24 C25 H25 119.6 . . ? C20 C25 H25 119.6 . . ? C13 C2 C7 107.80(15) . . ? C13 C2 C3 112.46(15) . . ? C7 C2 C3 110.36(16) . . ? C13 C2 C1 107.31(14) . . ? C7 C2 C1 112.93(15) . . ? C3 C2 C1 106.02(16) . . ? C21 C22 C23 119.31(19) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C14 C13 C18 117.66(19) . . ? C14 C13 C2 119.22(17) . . ? C18 C13 C2 123.09(18) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C12 C7 C8 117.71(18) . . ? C12 C7 C2 118.96(17) . . ? C8 C7 C2 123.17(17) . . ? C16 C15 C14 120.3(2) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C3 C4 C5 113.04(18) . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C7 C8 C9 120.6(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C15 C14 C13 121.1(2) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C21 C20 C25 119.11(19) . . ? C21 C20 C19 120.55(18) . . ? C25 C20 C19 120.26(17) . . ? C4 C3 C2 111.30(16) . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C11 C12 C7 121.1(2) . . ? C11 C12 H12 119.5 . . ? C7 C12 H12 119.5 . . ? C17 C18 C13 120.7(2) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? C18 C17 C16 120.6(2) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? N1 C5 C6 111.10(19) . . ? N1 C5 C4 108.75(16) . . ? C6 C5 C4 112.91(19) . . ? N1 C5 H5 108.0 . . ? C6 C5 H5 108.0 . . ? C4 C5 H5 108.0 . . ? C15 C16 C17 119.7(2) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C10 C11 C12 120.2(2) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C10 C9 C8 121.0(2) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C23 C24 C25 118.60(19) . . ? C23 C24 H24 120.7 . . ? C25 C24 H24 120.7 . . ? C9 C10 C11 119.4(2) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.194 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.034 _database_code_depnum_ccdc_archive 'CCDC 960600' ####################################################################### # # 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_130117a_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(4-bromobenzoyl)-2,4,4-trimethylpyrrolidine ; _chemical_absolute_configuration R _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 Br N O' _chemical_formula_weight 296.20 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.4870(11) _cell_length_b 9.5208(14) _cell_length_c 19.774(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1409.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 2.901 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.779874 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12032 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0374 _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 -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.41 _reflns_number_total 3209 _reflns_number_gt 2474 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0969P)^2^+0.2517P] 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 0.012(14) _refine_ls_number_reflns 3209 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.1201 _refine_ls_wR_factor_gt 0.1045 _refine_ls_goodness_of_fit_ref 0.815 _refine_ls_restrained_S_all 0.815 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br -0.10607(5) 0.75442(4) 0.16299(2) 0.07718(17) Uani 1 1 d . . . C12 C 0.1063(4) 0.7565(3) 0.21591(14) 0.0515(6) Uani 1 1 d . . . C9 C 0.4010(4) 0.7497(3) 0.29894(14) 0.0482(6) Uani 1 1 d . . . N1 N 0.6089(4) 0.6302(2) 0.37420(13) 0.0476(5) Uani 1 1 d . . . O1 O 0.6284(5) 0.8634(3) 0.36121(15) 0.0797(8) Uani 1 1 d . . . C8 C 0.5555(4) 0.7518(3) 0.34712(15) 0.0546(6) Uani 1 1 d . . . C2 C 0.5413(4) 0.4422(3) 0.44740(15) 0.0488(7) Uani 1 1 d . . . C1 C 0.5109(4) 0.4969(3) 0.37609(15) 0.0480(7) Uani 1 1 d . . . H1A H 0.5575 0.4317 0.3428 0.058 Uiso 1 1 calc R . . H1B H 0.3848 0.5117 0.3675 0.058 Uiso 1 1 calc R . . C10 C 0.2771(5) 0.8587(3) 0.30372(17) 0.0548(7) Uani 1 1 d . . . H10 H 0.2950 0.9298 0.3352 0.066 Uiso 1 1 calc R . . C14 C 0.3759(4) 0.6483(3) 0.24981(15) 0.0490(6) Uani 1 1 d . . . H14 H 0.4601 0.5772 0.2449 0.059 Uiso 1 1 calc R . . C4 C 0.7529(4) 0.6307(3) 0.42519(16) 0.0525(7) Uani 1 1 d . . . H4 H 0.7283 0.7042 0.4586 0.063 Uiso 1 1 calc R . . C13 C 0.2277(4) 0.6505(3) 0.20775(15) 0.0498(6) Uani 1 1 d . . . H13 H 0.2113 0.5818 0.1749 0.060 Uiso 1 1 calc R . . C11 C 0.1299(5) 0.8626(3) 0.26291(17) 0.0587(8) Uani 1 1 d . . . H11 H 0.0472 0.9351 0.2666 0.070 Uiso 1 1 calc R . . C3 C 0.7344(4) 0.4876(4) 0.45891(18) 0.0578(8) Uani 1 1 d . . . H3A H 0.8162 0.4206 0.4388 0.069 Uiso 1 1 calc R . . H3B H 0.7598 0.4943 0.5069 0.069 Uiso 1 1 calc R . . C7 C 0.5177(6) 0.2830(3) 0.45151(18) 0.0648(9) Uani 1 1 d . . . H7A H 0.5456 0.2515 0.4964 0.097 Uiso 1 1 calc R . . H7B H 0.5962 0.2383 0.4197 0.097 Uiso 1 1 calc R . . H7C H 0.3962 0.2590 0.4410 0.097 Uiso 1 1 calc R . . C6 C 0.4148(6) 0.5131(5) 0.49619(19) 0.0786(11) Uani 1 1 d . . . H6A H 0.4444 0.4862 0.5416 0.118 Uiso 1 1 calc R . . H6B H 0.2945 0.4851 0.4863 0.118 Uiso 1 1 calc R . . H6C H 0.4252 0.6132 0.4917 0.118 Uiso 1 1 calc R . . C5 C 0.9355(5) 0.6552(5) 0.3950(2) 0.0790(11) Uani 1 1 d . . . H5A H 0.9595 0.5846 0.3616 0.119 Uiso 1 1 calc R . . H5B H 1.0241 0.6504 0.4300 0.119 Uiso 1 1 calc R . . H5C H 0.9390 0.7463 0.3742 0.119 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 Br1 0.0710(2) 0.0731(3) 0.0874(3) 0.0128(2) -0.02174(16) 0.0042(2) C12 0.0550(14) 0.0456(14) 0.0541(14) 0.0165(13) -0.0020(11) 0.0022(17) C9 0.0608(14) 0.0344(12) 0.0493(14) 0.0119(12) 0.0023(11) 0.0022(17) N1 0.0470(12) 0.0376(11) 0.0582(13) 0.0055(10) -0.0056(12) -0.0066(11) O1 0.098(2) 0.0420(12) 0.0995(19) 0.0118(12) -0.0289(18) -0.0198(14) C8 0.0647(15) 0.0385(14) 0.0607(16) 0.0102(15) -0.0025(12) -0.0046(15) C2 0.0535(16) 0.0430(15) 0.0498(16) 0.0070(12) 0.0005(13) 0.0016(13) C1 0.0552(16) 0.0349(14) 0.0538(16) 0.0095(12) -0.0050(13) -0.0081(13) C10 0.0709(19) 0.0367(14) 0.0569(17) 0.0035(13) 0.0005(15) 0.0049(14) C14 0.0600(16) 0.0340(12) 0.0530(15) 0.0072(12) 0.0008(14) 0.0079(12) C4 0.0487(15) 0.0482(16) 0.0606(18) 0.0005(14) -0.0063(13) -0.0053(13) C13 0.0639(17) 0.0387(14) 0.0468(15) 0.0037(12) 0.0016(13) 0.0005(13) C11 0.069(2) 0.0414(14) 0.0656(19) 0.0052(14) 0.0083(16) 0.0138(15) C3 0.0575(17) 0.0553(18) 0.0605(18) 0.0100(15) -0.0095(14) 0.0029(15) C7 0.080(2) 0.051(2) 0.0640(19) 0.0207(15) -0.0066(16) -0.0042(16) C6 0.081(2) 0.083(3) 0.072(2) 0.006(2) 0.022(2) 0.014(2) C5 0.057(2) 0.081(3) 0.100(3) 0.005(2) -0.0005(19) -0.0153(19) _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 Br1 C12 1.903(3) . ? C12 C13 1.368(4) . ? C12 C11 1.384(4) . ? C9 C14 1.382(4) . ? C9 C10 1.395(4) . ? C9 C8 1.499(4) . ? N1 C8 1.337(4) . ? N1 C1 1.466(3) . ? N1 C4 1.476(4) . ? O1 C8 1.226(4) . ? C2 C6 1.511(5) . ? C2 C3 1.526(4) . ? C2 C7 1.529(4) . ? C2 C1 1.520(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C10 C11 1.367(5) . ? C10 H10 0.9300 . ? C14 C13 1.387(4) . ? C14 H14 0.9300 . ? C4 C5 1.510(5) . ? C4 C3 1.523(5) . ? C4 H4 0.9800 . ? C13 H13 0.9300 . ? C11 H11 0.9300 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? 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 C12 C11 122.2(3) . . ? C13 C12 Br1 118.9(2) . . ? C11 C12 Br1 118.9(2) . . ? C14 C9 C10 118.5(3) . . ? C14 C9 C8 124.1(3) . . ? C10 C9 C8 117.4(3) . . ? C8 N1 C1 127.6(3) . . ? C8 N1 C4 119.3(2) . . ? C1 N1 C4 110.5(2) . . ? O1 C8 N1 121.8(3) . . ? O1 C8 C9 120.0(3) . . ? N1 C8 C9 118.3(3) . . ? C6 C2 C3 111.8(3) . . ? C6 C2 C7 109.7(3) . . ? C3 C2 C7 112.5(3) . . ? C6 C2 C1 110.2(3) . . ? C3 C2 C1 100.5(3) . . ? C7 C2 C1 111.8(3) . . ? N1 C1 C2 104.2(2) . . ? N1 C1 H1A 110.9 . . ? C2 C1 H1A 110.9 . . ? N1 C1 H1B 110.9 . . ? C2 C1 H1B 110.9 . . ? H1A C1 H1B 108.9 . . ? C11 C10 C9 121.1(3) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C9 C14 C13 121.3(3) . . ? C9 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? N1 C4 C5 113.1(3) . . ? N1 C4 C3 103.3(2) . . ? C5 C4 C3 113.2(3) . . ? N1 C4 H4 109.0 . . ? C5 C4 H4 109.0 . . ? C3 C4 H4 109.0 . . ? C12 C13 C14 118.2(3) . . ? C12 C13 H13 120.9 . . ? C14 C13 H13 120.9 . . ? C12 C11 C10 118.6(3) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C2 C3 C4 105.9(3) . . ? C2 C3 H3A 110.6 . . ? C4 C3 H3A 110.6 . . ? C2 C3 H3B 110.6 . . ? C4 C3 H3B 110.6 . . ? H3A C3 H3B 108.7 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.339 _refine_diff_density_min -0.678 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 960601'