# Electronic Supplementary Material (ESI) for Chemical Science # 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_s1680rm2 _database_code_depnum_ccdc_archive 'CCDC 856190' #TrackingRef 'S1680RM2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'tert-Butyl-2-(4-bromophenyl)-2-cyano-2-(3-oxocyclohexyl)acetate' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H22 Br N O3, 0.5(C4 H10 O)' _chemical_formula_sum 'C21 H27 Br N O3.50' _chemical_formula_weight 429.35 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 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 8.953(2) _cell_length_b 9.856(2) _cell_length_c 14.208(3) _cell_angle_alpha 89.921(17) _cell_angle_beta 72.269(17) _cell_angle_gamma 70.983(17) _cell_volume 1122.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 8 _cell_measurement_theta_max 11 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 446 _exptl_absorpt_coefficient_mu 1.852 _exptl_absorpt_correction_type Psi-Scan _exptl_absorpt_correction_T_min 0.795 _exptl_absorpt_correction_T_max 0.848 _exptl_absorpt_process_details 'North et al., 1968' _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 'Nicolet P3' _diffrn_measurement_method Wyckoff-Scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 4942 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0955 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 24.00 _reflns_number_total 3524 _reflns_number_gt 1853 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3/PC Data Collection System' _computing_cell_refinement 'Siemens P3/PC Data Collection System' _computing_data_reduction 'SHELXTL-plus, XDISK (Sheldrick, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-plus, XP (Sheldrick, 1991)' _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^)+(0.0409P)^2^+1.4479P] 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_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3524 _refine_ls_number_parameters 264 _refine_ls_number_restraints 32 _refine_ls_R_factor_all 0.1601 _refine_ls_R_factor_gt 0.0800 _refine_ls_wR_factor_ref 0.1622 _refine_ls_wR_factor_gt 0.1409 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.04249(12) 1.00441(10) 0.31879(9) 0.0973(5) Uani 1 1 d . . . O1 O 1.2120(6) 0.3154(6) 0.0092(4) 0.0727(15) Uani 1 1 d . . . C1 C 0.6524(8) 0.4395(6) 0.2323(5) 0.0485(17) Uani 1 1 d . . . N1 N 0.6957(8) 0.3352(7) 0.3958(5) 0.0772(19) Uani 1 1 d . . . O2 O 0.6436(7) 0.3420(5) 0.0803(4) 0.0732(15) Uani 1 1 d . . . C2 C 0.6365(8) 0.3268(7) 0.1648(6) 0.0539(18) Uani 1 1 d . . . O3 O 0.6208(5) 0.2153(4) 0.2120(3) 0.0570(12) Uani 1 1 d . . . C3 C 0.6721(8) 0.3798(7) 0.3247(5) 0.0528(18) Uani 1 1 d . . . C4 C 0.8138(7) 0.4736(6) 0.1776(5) 0.0467(16) Uani 1 1 d . . . H4 H 0.7994 0.5143 0.1166 0.056 Uiso 1 1 calc R . . C5 C 0.9700(8) 0.3373(6) 0.1458(5) 0.058(2) Uani 1 1 d . . . H5A H 0.9868 0.2925 0.2043 0.070 Uiso 1 1 calc R . . H5B H 0.9537 0.2690 0.1043 0.070 Uiso 1 1 calc R . . C6 C 1.1228(9) 0.3722(7) 0.0893(6) 0.0571(19) Uani 1 1 d . . . C7 C 1.1507(8) 0.4898(8) 0.1425(6) 0.074(2) Uani 1 1 d . . . H7A H 1.2405 0.5162 0.0980 0.089 Uiso 1 1 calc R . . H7B H 1.1840 0.4536 0.1992 0.089 Uiso 1 1 calc R . . C8 C 0.9931(9) 0.6234(7) 0.1780(6) 0.072(2) Uani 1 1 d . . . H8A H 1.0105 0.6912 0.2194 0.087 Uiso 1 1 calc R . . H8B H 0.9719 0.6700 0.1209 0.087 Uiso 1 1 calc R . . C9 C 0.8421(8) 0.5853(6) 0.2368(5) 0.0561(19) Uani 1 1 d . . . H9A H 0.8582 0.5482 0.2975 0.067 Uiso 1 1 calc R . . H9B H 0.7439 0.6719 0.2550 0.067 Uiso 1 1 calc R . . C10 C 0.4958(7) 0.5781(6) 0.2561(5) 0.0452(16) Uani 1 1 d . . . C11 C 0.4050(8) 0.6373(7) 0.3506(6) 0.062(2) Uani 1 1 d . . . H11 H 0.4333 0.5913 0.4031 0.074 Uiso 1 1 calc R . . C12 C 0.2705(9) 0.7653(7) 0.3706(6) 0.069(2) Uani 1 1 d . . . H12 H 0.2109 0.8063 0.4357 0.083 Uiso 1 1 calc R . . C13 C 0.2272(8) 0.8299(7) 0.2938(6) 0.060(2) Uani 1 1 d . . . C14 C 0.3176(9) 0.7744(7) 0.1971(6) 0.065(2) Uani 1 1 d . . . H14 H 0.2880 0.8208 0.1451 0.078 Uiso 1 1 calc R . . C15 C 0.4549(8) 0.6470(7) 0.1779(5) 0.0545(18) Uani 1 1 d . . . H15 H 0.5186 0.6087 0.1127 0.065 Uiso 1 1 calc R . . C16 C 0.6199(9) 0.0837(7) 0.1606(6) 0.063(2) Uani 1 1 d . . . C17 C 0.7820(10) 0.0213(8) 0.0784(7) 0.105(3) Uani 1 1 d . . . H17A H 0.7905 0.0881 0.0295 0.158 Uiso 1 1 calc R . . H17B H 0.7870 -0.0678 0.0481 0.158 Uiso 1 1 calc R . . H17C H 0.8725 0.0035 0.1048 0.158 Uiso 1 1 calc R . . C18 C 0.4727(10) 0.1207(8) 0.1245(7) 0.090(3) Uani 1 1 d . . . H18A H 0.3723 0.1639 0.1793 0.135 Uiso 1 1 calc R . . H18B H 0.4691 0.0345 0.0953 0.135 Uiso 1 1 calc R . . H18C H 0.4821 0.1875 0.0756 0.135 Uiso 1 1 calc R . . C19 C 0.6050(11) -0.0139(8) 0.2412(7) 0.103(3) Uani 1 1 d . . . H19A H 0.6962 -0.0298 0.2668 0.154 Uiso 1 1 calc R . . H19B H 0.6079 -0.1046 0.2147 0.154 Uiso 1 1 calc R . . H19C H 0.5015 0.0300 0.2937 0.154 Uiso 1 1 calc R . . O1S O 0.0000 0.5000 0.5000 0.299(10) Uani 1 2 d SDU . . C1S C -0.164(5) 0.642(4) 0.526(3) 0.254(17) Uani 0.70 1 d PU A 1 H1S1 H -0.1713 0.6709 0.5928 0.305 Uiso 0.70 1 calc PR A 1 H1S2 H -0.2475 0.5966 0.5353 0.305 Uiso 0.70 1 calc PR A 1 C2S C -0.265(3) 0.797(2) 0.4987(16) 0.211(11) Uani 0.70 1 d PU A 1 H2S1 H -0.2167 0.8054 0.4297 0.317 Uiso 0.70 1 calc PR A 1 H2S2 H -0.2602 0.8727 0.5387 0.317 Uiso 0.70 1 calc PR A 1 H2S3 H -0.3798 0.8049 0.5117 0.317 Uiso 0.70 1 calc PR A 1 C1S1 C -0.057(5) 0.6389(15) 0.521(6) 0.22(3) Uani 0.30 1 d PDU A 2 H1S3 H 0.0009 0.6823 0.4668 0.266 Uiso 0.30 1 calc PR A 2 H1S4 H -0.0359 0.6636 0.5805 0.266 Uiso 0.30 1 calc PR A 2 C2S1 C -0.240(5) 0.697(6) 0.536(4) 0.133(17) Uani 0.30 1 d PDU A 2 H2S4 H -0.2791 0.8007 0.5493 0.200 Uiso 0.30 1 calc PR A 2 H2S5 H -0.2976 0.6582 0.5920 0.200 Uiso 0.30 1 calc PR A 2 H2S6 H -0.2608 0.6710 0.4778 0.200 Uiso 0.30 1 calc PR A 2 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 0.0743(6) 0.0693(6) 0.1298(10) 0.0104(5) -0.0341(6) 0.0008(4) O1 0.068(3) 0.081(4) 0.060(4) 0.001(3) -0.015(3) -0.019(3) C1 0.061(4) 0.039(3) 0.046(4) 0.005(3) -0.021(4) -0.015(3) N1 0.093(5) 0.069(4) 0.067(5) 0.019(4) -0.031(4) -0.019(4) O2 0.109(4) 0.067(3) 0.062(4) 0.012(3) -0.036(3) -0.046(3) C2 0.054(4) 0.049(4) 0.054(5) 0.006(4) -0.012(4) -0.016(3) O3 0.068(3) 0.042(2) 0.066(3) 0.007(2) -0.028(3) -0.019(2) C3 0.057(4) 0.041(4) 0.056(5) 0.005(3) -0.017(4) -0.012(3) C4 0.050(4) 0.040(3) 0.051(4) 0.008(3) -0.020(3) -0.014(3) C5 0.053(4) 0.038(3) 0.081(6) 0.002(3) -0.019(4) -0.014(3) C6 0.060(5) 0.050(4) 0.070(6) 0.012(4) -0.037(4) -0.016(4) C7 0.047(4) 0.079(5) 0.093(6) 0.009(5) -0.023(4) -0.017(4) C8 0.066(5) 0.056(4) 0.103(7) 0.006(4) -0.028(5) -0.031(4) C9 0.057(4) 0.043(4) 0.068(5) -0.003(4) -0.026(4) -0.011(3) C10 0.047(4) 0.051(4) 0.042(4) 0.004(3) -0.014(3) -0.023(3) C11 0.069(5) 0.056(4) 0.062(5) 0.013(4) -0.029(4) -0.017(4) C12 0.066(5) 0.061(4) 0.068(6) 0.001(4) -0.017(4) -0.010(4) C13 0.048(4) 0.048(4) 0.083(6) 0.011(4) -0.024(4) -0.012(3) C14 0.059(5) 0.064(5) 0.080(6) 0.028(4) -0.031(4) -0.022(4) C15 0.060(4) 0.061(4) 0.050(4) 0.014(3) -0.023(4) -0.025(3) C16 0.074(5) 0.041(4) 0.080(6) 0.001(4) -0.033(4) -0.018(3) C17 0.093(7) 0.055(5) 0.139(9) -0.038(5) -0.018(6) -0.007(5) C18 0.083(6) 0.069(5) 0.142(8) 0.014(5) -0.066(6) -0.031(4) C19 0.131(8) 0.054(5) 0.163(9) 0.039(6) -0.083(7) -0.049(5) O1S 0.299(17) 0.306(19) 0.330(18) -0.007(15) -0.111(14) -0.145(15) C1S 0.25(2) 0.27(3) 0.25(2) 0.037(18) -0.091(19) -0.085(18) C2S 0.26(2) 0.214(17) 0.159(16) 0.003(14) -0.035(14) -0.104(15) C1S1 0.22(4) 0.23(4) 0.23(4) 0.03(2) -0.07(2) -0.09(2) C2S1 0.13(2) 0.13(2) 0.12(2) 0.012(17) -0.027(17) -0.031(17) _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 C13 1.900(6) . ? O1 C6 1.185(8) . ? C1 C3 1.473(9) . ? C1 C2 1.538(9) . ? C1 C10 1.553(8) . ? C1 C4 1.561(8) . ? N1 C3 1.152(8) . ? O2 C2 1.196(8) . ? C2 O3 1.311(7) . ? O3 C16 1.493(8) . ? C4 C9 1.516(8) . ? C4 C5 1.535(7) . ? C4 H4 0.9800 . ? C5 C6 1.506(9) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.512(10) . ? C7 C8 1.529(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.519(9) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.353(8) . ? C10 C15 1.383(8) . ? C11 C12 1.387(9) . ? C11 H11 0.9300 . ? C12 C13 1.357(9) . ? C12 H12 0.9300 . ? C13 C14 1.370(9) . ? C14 C15 1.397(9) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C18 1.494(9) . ? C16 C17 1.495(10) . ? C16 C19 1.497(10) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? O1S C1S1 1.294(10) . ? O1S C1S1 1.294(10) 2_566 ? O1S C1S 1.61(3) . ? O1S C1S 1.61(3) 2_566 ? C1S C2S 1.61(4) . ? C1S H1S1 0.9700 . ? C1S H1S2 0.9700 . ? C2S H2S1 0.9600 . ? C2S H2S2 0.9600 . ? C2S H2S3 0.9600 . ? C1S1 C2S1 1.494(10) . ? C1S1 H1S3 0.9700 . ? C1S1 H1S4 0.9700 . ? C2S1 H2S4 0.9600 . ? C2S1 H2S5 0.9600 . ? C2S1 H2S6 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 C3 C1 C2 110.0(5) . . ? C3 C1 C10 110.5(5) . . ? C2 C1 C10 109.7(5) . . ? C3 C1 C4 107.4(5) . . ? C2 C1 C4 108.4(5) . . ? C10 C1 C4 110.8(5) . . ? O2 C2 O3 127.0(7) . . ? O2 C2 C1 122.3(6) . . ? O3 C2 C1 110.7(6) . . ? C2 O3 C16 121.7(6) . . ? N1 C3 C1 176.0(8) . . ? C9 C4 C5 109.9(5) . . ? C9 C4 C1 113.3(5) . . ? C5 C4 C1 112.4(5) . . ? C9 C4 H4 106.9 . . ? C5 C4 H4 106.9 . . ? C1 C4 H4 106.9 . . ? C6 C5 C4 111.4(5) . . ? C6 C5 H5A 109.4 . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5B 109.4 . . ? C4 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? O1 C6 C5 123.5(7) . . ? O1 C6 C7 122.4(7) . . ? C5 C6 C7 114.1(7) . . ? C6 C7 C8 111.4(6) . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C9 C8 C7 111.8(6) . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? C4 C9 C8 111.6(6) . . ? C4 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? C4 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C15 119.5(6) . . ? C11 C10 C1 121.8(6) . . ? C15 C10 C1 118.6(6) . . ? C10 C11 C12 121.2(7) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C13 C12 C11 119.1(7) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 121.3(6) . . ? C12 C13 Br1 120.1(6) . . ? C14 C13 Br1 118.5(6) . . ? C13 C14 C15 119.0(7) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C10 C15 C14 119.8(7) . . ? C10 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? O3 C16 C18 110.0(5) . . ? O3 C16 C17 108.5(6) . . ? C18 C16 C17 112.6(7) . . ? O3 C16 C19 102.9(6) . . ? C18 C16 C19 111.1(7) . . ? C17 C16 C19 111.3(7) . . ? 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 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C1S1 O1S C1S1 180.000(6) . 2_566 ? C1S1 O1S C1S 35(3) . . ? C1S1 O1S C1S 145(3) 2_566 . ? C1S1 O1S C1S 145(3) . 2_566 ? C1S1 O1S C1S 35(3) 2_566 2_566 ? C1S O1S C1S 180.000(6) . 2_566 ? O1S C1S C2S 150(3) . . ? O1S C1S H1S1 99.0 . . ? C2S C1S H1S1 99.0 . . ? O1S C1S H1S2 99.0 . . ? C2S C1S H1S2 99.0 . . ? H1S1 C1S H1S2 103.9 . . ? O1S C1S1 C2S1 111(3) . . ? O1S C1S1 H1S3 109.5 . . ? C2S1 C1S1 H1S3 109.5 . . ? O1S C1S1 H1S4 109.5 . . ? C2S1 C1S1 H1S4 109.5 . . ? H1S3 C1S1 H1S4 108.1 . . ? C1S1 C2S1 H2S4 109.5 . . ? C1S1 C2S1 H2S5 109.5 . . ? H2S4 C2S1 H2S5 109.5 . . ? C1S1 C2S1 H2S6 109.5 . . ? H2S4 C2S1 H2S6 109.5 . . ? H2S5 C2S1 H2S6 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 C3 C1 C2 O2 -169.0(6) . . . . ? C10 C1 C2 O2 69.3(8) . . . . ? C4 C1 C2 O2 -51.8(8) . . . . ? C3 C1 C2 O3 8.9(7) . . . . ? C10 C1 C2 O3 -112.8(6) . . . . ? C4 C1 C2 O3 126.1(5) . . . . ? O2 C2 O3 C16 3.9(10) . . . . ? C1 C2 O3 C16 -173.9(5) . . . . ? C2 C1 C3 N1 127(10) . . . . ? C10 C1 C3 N1 -112(10) . . . . ? C4 C1 C3 N1 9(10) . . . . ? C3 C1 C4 C9 -61.8(6) . . . . ? C2 C1 C4 C9 179.4(5) . . . . ? C10 C1 C4 C9 59.0(7) . . . . ? C3 C1 C4 C5 63.6(7) . . . . ? C2 C1 C4 C5 -55.3(7) . . . . ? C10 C1 C4 C5 -175.7(5) . . . . ? C9 C4 C5 C6 -55.3(8) . . . . ? C1 C4 C5 C6 177.6(6) . . . . ? C4 C5 C6 O1 -125.5(7) . . . . ? C4 C5 C6 C7 52.9(8) . . . . ? O1 C6 C7 C8 127.9(7) . . . . ? C5 C6 C7 C8 -50.5(8) . . . . ? C6 C7 C8 C9 51.3(9) . . . . ? C5 C4 C9 C8 57.5(7) . . . . ? C1 C4 C9 C8 -175.9(5) . . . . ? C7 C8 C9 C4 -56.1(8) . . . . ? C3 C1 C10 C11 5.8(9) . . . . ? C2 C1 C10 C11 127.2(7) . . . . ? C4 C1 C10 C11 -113.1(7) . . . . ? C3 C1 C10 C15 -178.2(6) . . . . ? C2 C1 C10 C15 -56.8(8) . . . . ? C4 C1 C10 C15 62.9(7) . . . . ? C15 C10 C11 C12 0.6(11) . . . . ? C1 C10 C11 C12 176.6(6) . . . . ? C10 C11 C12 C13 1.7(12) . . . . ? C11 C12 C13 C14 -2.7(12) . . . . ? C11 C12 C13 Br1 179.4(5) . . . . ? C12 C13 C14 C15 1.3(11) . . . . ? Br1 C13 C14 C15 179.3(5) . . . . ? C11 C10 C15 C14 -2.0(10) . . . . ? C1 C10 C15 C14 -178.0(6) . . . . ? C13 C14 C15 C10 1.0(11) . . . . ? C2 O3 C16 C18 -63.3(8) . . . . ? C2 O3 C16 C17 60.3(8) . . . . ? C2 O3 C16 C19 178.3(6) . . . . ? C1S1 O1S C1S C2S 63(8) . . . . ? C1S1 O1S C1S C2S -117(8) 2_566 . . . ? C1S O1S C1S C2S -157(100) 2_566 . . . ? C1S1 O1S C1S1 C2S1 -92(100) 2_566 . . . ? C1S O1S C1S1 C2S1 0(5) . . . . ? C1S O1S C1S1 C2S1 -180(5) 2_566 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.355 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.063 data_s1731rm _database_code_depnum_ccdc_archive 'CCDC 856191' #TrackingRef 'S1731RM.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '(R)-tert-Butyl-2-(4-bromophenyl)-2-cyano-2-((R)-2-oxooxepan-4-yl)acetate' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H22 Br N O4' _chemical_absolute_Configuration rd _chemical_formula_sum 'C19 H22 Br N O4' _chemical_formula_weight 408.29 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 'C 2' _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 28.468(5) _cell_length_b 6.5087(19) _cell_length_c 10.903(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.161(17) _cell_angle_gamma 90.00 _cell_volume 1982.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 48 _cell_measurement_theta_min 10 _cell_measurement_theta_max 13 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.9 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 2.095 _exptl_absorpt_correction_type PSI-Scan _exptl_absorpt_correction_T_min 0.714 _exptl_absorpt_correction_T_max 0.871 _exptl_absorpt_process_details 'North et al., 1968' _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 'Nicolet P3' _diffrn_measurement_method Wyckoff-Scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3 _diffrn_reflns_number 3966 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3888 _reflns_number_gt 2893 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3/PC Data Collection System' _computing_cell_refinement 'Siemens P3/PC Data Collection System' _computing_data_reduction 'SHELXTL-plus, XDISK (Sheldrick, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-plus, XP (Sheldrick, 1991)' _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^)+(0.0611P)^2^+4.9898P] 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 0.0015(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.003(19) _refine_ls_number_reflns 3888 _refine_ls_number_parameters 230 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0986 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.1602 _refine_ls_wR_factor_gt 0.1444 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.91488(3) 0.62505(18) 0.85605(6) 0.0811(3) Uani 1 1 d . . . O1 O 0.91565(19) -0.1869(8) 0.3642(5) 0.0720(15) Uani 1 1 d . . . C1 C 0.8554(2) 0.0542(9) 0.3983(5) 0.0404(13) Uani 1 1 d . . . N1 N 0.8101(2) -0.2705(10) 0.4519(6) 0.0677(17) Uani 1 1 d . . . O2 O 0.91656(12) 0.1299(9) 0.2874(3) 0.0456(8) Uani 1 1 d . . . C2 C 0.8310(2) -0.1329(10) 0.4313(6) 0.0473(15) Uani 1 1 d . . . O3 O 0.8178(2) 0.1924(9) -0.0161(4) 0.0787(19) Uani 1 1 d . . . C3 C 0.8999(2) -0.0193(10) 0.3479(5) 0.0407(13) Uani 1 1 d . . . C4 C 0.8194(2) 0.1689(10) 0.2936(5) 0.0425(14) Uani 1 1 d . . . H4 H 0.8349 0.2952 0.2724 0.051 Uiso 1 1 calc R . . O4 O 0.7493(2) 0.2465(9) 0.0371(5) 0.0718(15) Uani 1 1 d . . . C5 C 0.8075(2) 0.0344(10) 0.1742(5) 0.0488(15) Uani 1 1 d . . . H5A H 0.8355 -0.0458 0.1664 0.059 Uiso 1 1 calc R . . H5B H 0.7820 -0.0606 0.1826 0.059 Uiso 1 1 calc R . . C6 C 0.7924(3) 0.1582(13) 0.0592(6) 0.0592(18) Uani 1 1 d . . . C7 C 0.7180(3) 0.2243(14) 0.1261(8) 0.075(2) Uani 1 1 d . . . H7A H 0.7148 0.0797 0.1445 0.090 Uiso 1 1 calc R . . H7B H 0.6865 0.2762 0.0894 0.090 Uiso 1 1 calc R . . C8 C 0.7367(3) 0.3380(15) 0.2457(8) 0.076(2) Uani 1 1 d . . . H8A H 0.7097 0.3707 0.2846 0.092 Uiso 1 1 calc R . . H8B H 0.7502 0.4671 0.2246 0.092 Uiso 1 1 calc R . . C9 C 0.7743(3) 0.2290(12) 0.3423(7) 0.0593(18) Uani 1 1 d . . . H9A H 0.7602 0.1059 0.3700 0.071 Uiso 1 1 calc R . . H9B H 0.7834 0.3182 0.4143 0.071 Uiso 1 1 calc R . . C10 C 0.8714(2) 0.1912(9) 0.5137(5) 0.0424(15) Uani 1 1 d . . . C11 C 0.8626(2) 0.1372(16) 0.6299(5) 0.0622(18) Uani 1 1 d . . . H11 H 0.8478 0.0125 0.6396 0.075 Uiso 1 1 calc R . . C12 C 0.8755(3) 0.2656(14) 0.7319(6) 0.069(2) Uani 1 1 d . . . H12 H 0.8688 0.2294 0.8093 0.083 Uiso 1 1 calc R . . C13 C 0.8978(2) 0.4440(11) 0.7176(5) 0.0520(17) Uani 1 1 d . . . C14 C 0.9079(3) 0.5014(11) 0.6049(6) 0.0532(16) Uani 1 1 d . . . H14 H 0.9235 0.6249 0.5971 0.064 Uiso 1 1 calc R . . C15 C 0.8948(2) 0.3732(10) 0.5026(5) 0.0458(15) Uani 1 1 d . . . H15 H 0.9018 0.4106 0.4258 0.055 Uiso 1 1 calc R . . C16 C 0.9580(2) 0.1044(16) 0.2252(5) 0.0575(17) Uani 1 1 d . . . C17 C 0.9634(4) 0.3162(18) 0.1756(9) 0.094(3) Uani 1 1 d . . . H17A H 0.9336 0.3588 0.1248 0.142 Uiso 1 1 calc R . . H17B H 0.9878 0.3154 0.1260 0.142 Uiso 1 1 calc R . . H17C H 0.9722 0.4101 0.2441 0.142 Uiso 1 1 calc R . . C18 C 1.0019(3) 0.0429(19) 0.3196(8) 0.097(4) Uani 1 1 d . . . H18A H 1.0285 0.0262 0.2782 0.146 Uiso 1 1 calc R . . H18B H 0.9959 -0.0845 0.3582 0.146 Uiso 1 1 calc R . . H18C H 1.0092 0.1477 0.3823 0.146 Uiso 1 1 calc R . . C19 C 0.9446(3) -0.0480(18) 0.1200(8) 0.088(3) Uani 1 1 d . . . H19A H 0.9149 -0.0076 0.0680 0.133 Uiso 1 1 calc R . . H19B H 0.9412 -0.1820 0.1541 0.133 Uiso 1 1 calc R . . H19C H 0.9692 -0.0516 0.0710 0.133 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 0.0879(6) 0.1067(7) 0.0469(3) -0.0266(5) 0.0087(3) -0.0014(6) O1 0.065(3) 0.060(3) 0.100(4) 0.025(3) 0.040(3) 0.023(3) C1 0.037(3) 0.045(4) 0.041(3) 0.002(2) 0.012(2) 0.005(3) N1 0.062(4) 0.059(4) 0.083(4) 0.005(3) 0.019(3) -0.007(3) O2 0.043(2) 0.051(2) 0.0471(18) 0.002(2) 0.0190(15) 0.001(3) C2 0.041(3) 0.048(4) 0.055(3) 0.000(3) 0.013(3) 0.000(3) O3 0.082(4) 0.108(6) 0.048(2) 0.003(3) 0.016(3) -0.014(3) C3 0.038(3) 0.046(4) 0.040(3) 0.003(2) 0.011(2) 0.000(3) C4 0.037(3) 0.048(4) 0.043(3) -0.005(2) 0.007(2) 0.008(3) O4 0.071(4) 0.080(4) 0.058(3) 0.014(3) -0.002(3) 0.007(3) C5 0.043(3) 0.055(4) 0.045(3) -0.003(3) 0.002(3) 0.005(3) C6 0.058(4) 0.066(5) 0.050(3) 0.002(3) 0.000(3) -0.004(4) C7 0.045(4) 0.091(6) 0.081(5) 0.011(4) -0.006(4) 0.007(4) C8 0.049(4) 0.092(6) 0.087(6) 0.008(5) 0.011(4) 0.035(4) C9 0.051(4) 0.072(5) 0.059(4) 0.002(3) 0.019(3) 0.013(4) C10 0.041(3) 0.051(4) 0.037(3) 0.005(2) 0.012(2) 0.003(3) C11 0.069(4) 0.077(5) 0.044(3) 0.004(4) 0.020(3) -0.028(5) C12 0.077(5) 0.095(6) 0.040(3) -0.004(3) 0.025(3) -0.025(5) C13 0.050(4) 0.069(5) 0.038(3) -0.011(3) 0.011(3) 0.000(3) C14 0.060(4) 0.054(4) 0.047(3) 0.002(3) 0.013(3) 0.001(3) C15 0.059(4) 0.047(4) 0.032(3) 0.002(2) 0.010(3) 0.009(3) C16 0.046(3) 0.083(5) 0.048(3) -0.002(4) 0.021(2) 0.000(4) C17 0.090(8) 0.121(9) 0.084(6) 0.013(6) 0.045(6) -0.022(7) C18 0.043(4) 0.170(13) 0.080(5) 0.007(6) 0.015(4) -0.002(5) C19 0.076(6) 0.136(9) 0.058(5) -0.037(5) 0.026(4) 0.004(6) _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 C13 1.903(6) . ? O1 C3 1.180(8) . ? C1 C2 1.482(9) . ? C1 C10 1.537(8) . ? C1 C3 1.551(8) . ? C1 C4 1.567(7) . ? N1 C2 1.122(8) . ? O2 C3 1.313(7) . ? O2 C16 1.481(6) . ? O3 C6 1.215(8) . ? C4 C9 1.533(8) . ? C4 C5 1.551(8) . ? C4 H4 0.9800 . ? O4 C6 1.333(9) . ? O4 C7 1.447(9) . ? C5 C6 1.482(9) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C7 C8 1.504(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.524(10) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C15 1.375(8) . ? C10 C11 1.384(7) . ? C11 C12 1.383(10) . ? C11 H11 0.9300 . ? C12 C13 1.347(10) . ? C12 H12 0.9300 . ? C13 C14 1.367(8) . ? C14 C15 1.385(8) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.499(14) . ? C16 C19 1.509(12) . ? C16 C18 1.510(10) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 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 C2 C1 C10 110.9(5) . . ? C2 C1 C3 106.7(5) . . ? C10 C1 C3 109.6(5) . . ? C2 C1 C4 107.2(5) . . ? C10 C1 C4 111.6(4) . . ? C3 C1 C4 110.7(4) . . ? C3 O2 C16 123.0(6) . . ? N1 C2 C1 175.9(7) . . ? O1 C3 O2 126.6(6) . . ? O1 C3 C1 123.0(6) . . ? O2 C3 C1 110.4(5) . . ? C9 C4 C5 111.9(5) . . ? C9 C4 C1 110.1(5) . . ? C5 C4 C1 110.4(5) . . ? C9 C4 H4 108.1 . . ? C5 C4 H4 108.1 . . ? C1 C4 H4 108.1 . . ? C6 O4 C7 120.0(6) . . ? C6 C5 C4 112.5(6) . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5A 109.1 . . ? C6 C5 H5B 109.1 . . ? C4 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? O3 C6 O4 116.4(7) . . ? O3 C6 C5 123.9(7) . . ? O4 C6 C5 119.6(6) . . ? O4 C7 C8 111.8(7) . . ? O4 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? O4 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C7 C8 C9 117.0(7) . . ? C7 C8 H8A 108.1 . . ? C9 C8 H8A 108.1 . . ? C7 C8 H8B 108.1 . . ? C9 C8 H8B 108.1 . . ? H8A C8 H8B 107.3 . . ? C8 C9 C4 113.8(6) . . ? C8 C9 H9A 108.8 . . ? C4 C9 H9A 108.8 . . ? C8 C9 H9B 108.8 . . ? C4 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C15 C10 C11 118.4(6) . . ? C15 C10 C1 120.0(5) . . ? C11 C10 C1 121.7(6) . . ? C12 C11 C10 121.1(8) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C13 C12 C11 119.0(6) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 121.8(6) . . ? C12 C13 Br1 119.7(5) . . ? C14 C13 Br1 118.5(6) . . ? C13 C14 C15 119.2(6) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C10 C15 C14 120.5(6) . . ? C10 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? O2 C16 C17 102.0(7) . . ? O2 C16 C19 108.3(6) . . ? C17 C16 C19 111.0(7) . . ? O2 C16 C18 110.2(5) . . ? C17 C16 C18 111.2(8) . . ? C19 C16 C18 113.5(9) . . ? 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 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C10 C1 C2 N1 115(10) . . . . ? C3 C1 C2 N1 -126(10) . . . . ? C4 C1 C2 N1 -7(10) . . . . ? C16 O2 C3 O1 2.3(10) . . . . ? C16 O2 C3 C1 -178.1(5) . . . . ? C2 C1 C3 O1 -16.5(8) . . . . ? C10 C1 C3 O1 103.7(7) . . . . ? C4 C1 C3 O1 -132.8(7) . . . . ? C2 C1 C3 O2 163.8(5) . . . . ? C10 C1 C3 O2 -76.0(5) . . . . ? C4 C1 C3 O2 47.5(6) . . . . ? C2 C1 C4 C9 60.5(6) . . . . ? C10 C1 C4 C9 -61.1(7) . . . . ? C3 C1 C4 C9 176.5(5) . . . . ? C2 C1 C4 C5 -63.4(6) . . . . ? C10 C1 C4 C5 175.0(5) . . . . ? C3 C1 C4 C5 52.6(6) . . . . ? C9 C4 C5 C6 82.4(7) . . . . ? C1 C4 C5 C6 -154.7(5) . . . . ? C7 O4 C6 O3 -176.2(7) . . . . ? C7 O4 C6 C5 1.1(11) . . . . ? C4 C5 C6 O3 104.2(8) . . . . ? C4 C5 C6 O4 -72.9(8) . . . . ? C6 O4 C7 C8 68.9(9) . . . . ? O4 C7 C8 C9 -83.1(9) . . . . ? C7 C8 C9 C4 58.3(10) . . . . ? C5 C4 C9 C8 -55.8(8) . . . . ? C1 C4 C9 C8 -178.9(6) . . . . ? C2 C1 C10 C15 -179.8(6) . . . . ? C3 C1 C10 C15 62.7(7) . . . . ? C4 C1 C10 C15 -60.3(7) . . . . ? C2 C1 C10 C11 -0.3(8) . . . . ? C3 C1 C10 C11 -117.9(7) . . . . ? C4 C1 C10 C11 119.2(7) . . . . ? C15 C10 C11 C12 2.1(11) . . . . ? C1 C10 C11 C12 -177.3(7) . . . . ? C10 C11 C12 C13 -1.4(13) . . . . ? C11 C12 C13 C14 0.1(13) . . . . ? C11 C12 C13 Br1 179.1(6) . . . . ? C12 C13 C14 C15 0.3(11) . . . . ? Br1 C13 C14 C15 -178.6(5) . . . . ? C11 C10 C15 C14 -1.7(10) . . . . ? C1 C10 C15 C14 177.8(6) . . . . ? C13 C14 C15 C10 0.5(10) . . . . ? C3 O2 C16 C17 -178.0(6) . . . . ? C3 O2 C16 C19 64.8(8) . . . . ? C3 O2 C16 C18 -59.9(10) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.443 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.065 data_s1755rm1 _database_code_depnum_ccdc_archive 'CCDC 856192' #TrackingRef 'S1755RM1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'tert-Butyl-2-cyano-2-(3-hydroxycyclohexyl)-2-(4-methoxyphenyl)acetate' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H27 N O4' _chemical_formula_sum 'C20 H27 N O4' _chemical_formula_weight 345.43 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 n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 16.349(3) _cell_length_b 11.424(3) _cell_length_c 20.499(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3828.6(15) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 10 _cell_measurement_theta_max 12 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Nicolet P3' _diffrn_measurement_method Wyckoff-Scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8508 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0913 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.99 _reflns_number_total 8372 _reflns_number_gt 4570 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3/PC Data Collection System' _computing_cell_refinement 'Siemens P3/PC Data Collection System' _computing_data_reduction 'SHELXTL-plus, XDISK (Sheldrick, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-plus, XP (Sheldrick, 1991)' _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^)+(0.0361P)^2^+1.2232P] 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 SHELXL _refine_ls_extinction_coef 0.00109(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.9(17) _refine_ls_number_reflns 8372 _refine_ls_number_parameters 468 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1600 _refine_ls_R_factor_gt 0.0787 _refine_ls_wR_factor_ref 0.1553 _refine_ls_wR_factor_gt 0.1325 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 O1A O 0.6965(2) 0.7626(4) 0.0742(2) 0.0638(11) Uani 1 1 d . . . H1A H 0.683(4) 0.775(6) 0.115(3) 0.10(3) Uiso 1 1 d . . . N1A N 0.5503(2) 0.3265(4) 0.0112(2) 0.0606(14) Uani 1 1 d . . . C1A C 0.4557(2) 0.5062(5) 0.0340(2) 0.0387(11) Uani 1 1 d . . . O2A O 0.3360(2) 0.5730(3) -0.02415(17) 0.0526(9) Uani 1 1 d . . . C2A C 0.3725(3) 0.4926(5) -0.0013(3) 0.0418(12) Uani 1 1 d . . . O3A O 0.35022(17) 0.3804(3) 0.00131(17) 0.0490(9) Uani 1 1 d . . . C3A C 0.5076(3) 0.4039(5) 0.0209(2) 0.0421(12) Uani 1 1 d . . . O4A O 0.3703(2) 0.5222(4) 0.30338(17) 0.0576(10) Uani 1 1 d . . . C4A C 0.5017(3) 0.6189(4) 0.0133(2) 0.0397(11) Uani 1 1 d . . . H4A H 0.4647 0.6852 0.0202 0.048 Uiso 1 1 calc R . . C5A C 0.5781(3) 0.6394(4) 0.0555(2) 0.0441(12) Uani 1 1 d . . . H5A1 H 0.5618 0.6447 0.1009 0.053 Uiso 1 1 calc R . . H5A2 H 0.6145 0.5728 0.0511 0.053 Uiso 1 1 calc R . . C6A C 0.6235(3) 0.7492(5) 0.0368(3) 0.0507(13) Uani 1 1 d . . . H6A H 0.5880 0.8167 0.0449 0.061 Uiso 1 1 calc R . . C7A C 0.6468(3) 0.7478(6) -0.0344(3) 0.0629(16) Uani 1 1 d . . . H7A1 H 0.6859 0.6854 -0.0422 0.075 Uiso 1 1 calc R . . H7A2 H 0.6729 0.8214 -0.0457 0.075 Uiso 1 1 calc R . . C8A C 0.5718(3) 0.7295(6) -0.0781(3) 0.0611(17) Uani 1 1 d . . . H8A1 H 0.5355 0.7962 -0.0740 0.073 Uiso 1 1 calc R . . H8A2 H 0.5891 0.7243 -0.1233 0.073 Uiso 1 1 calc R . . C9A C 0.5263(3) 0.6186(5) -0.0594(2) 0.0564(15) Uani 1 1 d . . . H9A1 H 0.5607 0.5513 -0.0681 0.068 Uiso 1 1 calc R . . H9A2 H 0.4775 0.6115 -0.0860 0.068 Uiso 1 1 calc R . . C10A C 0.4324(2) 0.5105(4) 0.1069(2) 0.0358(11) Uani 1 1 d . . . C11A C 0.3735(3) 0.5885(5) 0.1283(2) 0.0403(12) Uani 1 1 d . . . H11A H 0.3487 0.6378 0.0982 0.048 Uiso 1 1 calc R . . C12A C 0.3505(3) 0.5954(5) 0.1931(3) 0.0454(13) Uani 1 1 d . . . H12A H 0.3104 0.6480 0.2062 0.054 Uiso 1 1 calc R . . C13A C 0.3877(3) 0.5235(5) 0.2375(3) 0.0419(12) Uani 1 1 d . . . C14A C 0.4463(3) 0.4451(5) 0.2178(3) 0.0497(14) Uani 1 1 d . . . H14A H 0.4717 0.3971 0.2483 0.060 Uiso 1 1 calc R . . C15A C 0.4676(3) 0.4374(5) 0.1527(3) 0.0477(13) Uani 1 1 d . . . H15A H 0.5060 0.3822 0.1396 0.057 Uiso 1 1 calc R . . C16A C 0.3075(4) 0.5981(6) 0.3257(3) 0.077(2) Uani 1 1 d . . . H16A H 0.3221 0.6777 0.3163 0.116 Uiso 1 1 calc R . . H16B H 0.3008 0.5887 0.3719 0.116 Uiso 1 1 calc R . . H16C H 0.2571 0.5792 0.3040 0.116 Uiso 1 1 calc R . . C17A C 0.2629(3) 0.3426(5) -0.0038(2) 0.0443(13) Uani 1 1 d . . . C18A C 0.2264(3) 0.3734(6) -0.0691(3) 0.0645(18) Uani 1 1 d . . . H18A H 0.2211 0.4568 -0.0726 0.097 Uiso 1 1 calc R . . H18B H 0.1734 0.3377 -0.0731 0.097 Uiso 1 1 calc R . . H18C H 0.2614 0.3451 -0.1033 0.097 Uiso 1 1 calc R . . C19A C 0.2161(3) 0.4001(6) 0.0512(3) 0.0669(18) Uani 1 1 d . . . H19A H 0.2129 0.4829 0.0435 0.100 Uiso 1 1 calc R . . H19B H 0.2438 0.3859 0.0917 0.100 Uiso 1 1 calc R . . H19C H 0.1619 0.3679 0.0532 0.100 Uiso 1 1 calc R . . C20A C 0.2692(3) 0.2130(5) 0.0046(3) 0.0683(18) Uani 1 1 d . . . H20A H 0.2154 0.1794 0.0046 0.102 Uiso 1 1 calc R . . H20B H 0.2959 0.1958 0.0451 0.102 Uiso 1 1 calc R . . H20C H 0.3004 0.1806 -0.0308 0.102 Uiso 1 1 calc R . . O1B O 0.6694(2) 0.7346(4) 0.2123(2) 0.0619(12) Uani 1 1 d . . . H1B H 0.690(3) 0.670(4) 0.228(2) 0.050(16) Uiso 1 1 d . . . N1B N 0.5209(2) 1.1675(4) 0.2528(2) 0.0495(11) Uani 1 1 d . . . C1B C 0.4297(2) 0.9921(4) 0.2147(2) 0.0329(10) Uani 1 1 d . . . O2B O 0.29663(17) 0.9262(3) 0.24944(18) 0.0485(9) Uani 1 1 d . . . C2B C 0.3400(2) 1.0088(4) 0.2393(2) 0.0355(10) Uani 1 1 d . . . O3B O 0.32107(16) 1.1195(3) 0.24100(17) 0.0419(8) Uani 1 1 d . . . C3B C 0.4799(2) 1.0945(4) 0.2358(2) 0.0387(11) Uani 1 1 d . . . O4B O 0.4161(2) 0.9705(4) -0.06225(16) 0.0638(12) Uani 1 1 d . . . C4B C 0.4676(2) 0.8786(4) 0.2432(2) 0.0340(10) Uani 1 1 d . . . H4B H 0.4323 0.8130 0.2305 0.041 Uiso 1 1 calc R . . C5B C 0.5531(3) 0.8557(4) 0.2146(2) 0.0409(12) Uani 1 1 d . . . H5B1 H 0.5495 0.8511 0.1675 0.049 Uiso 1 1 calc R . . H5B2 H 0.5890 0.9204 0.2256 0.049 Uiso 1 1 calc R . . C6B C 0.5887(3) 0.7430(5) 0.2409(2) 0.0466(12) Uani 1 1 d . . . H6B H 0.5552 0.6768 0.2265 0.056 Uiso 1 1 calc R . . C7B C 0.5930(3) 0.7442(6) 0.3148(2) 0.0604(16) Uani 1 1 d . . . H7B1 H 0.6305 0.8047 0.3290 0.072 Uiso 1 1 calc R . . H7B2 H 0.6135 0.6695 0.3303 0.072 Uiso 1 1 calc R . . C8B C 0.5079(3) 0.7670(5) 0.3441(2) 0.0573(15) Uani 1 1 d . . . H8B1 H 0.4717 0.7025 0.3334 0.069 Uiso 1 1 calc R . . H8B2 H 0.5120 0.7719 0.3912 0.069 Uiso 1 1 calc R . . C9B C 0.4725(3) 0.8799(5) 0.3177(2) 0.0492(13) Uani 1 1 d . . . H9B1 H 0.5064 0.9450 0.3316 0.059 Uiso 1 1 calc R . . H9B2 H 0.4182 0.8914 0.3356 0.059 Uiso 1 1 calc R . . C10B C 0.4244(3) 0.9891(4) 0.1397(2) 0.0333(10) Uani 1 1 d . . . C11B C 0.3715(3) 0.9109(5) 0.1100(2) 0.0398(12) Uani 1 1 d . . . H11B H 0.3387 0.8633 0.1359 0.048 Uiso 1 1 calc R . . C12B C 0.3662(3) 0.9017(5) 0.0429(2) 0.0418(12) Uani 1 1 d . . . H12B H 0.3295 0.8498 0.0237 0.050 Uiso 1 1 calc R . . C13B C 0.4160(3) 0.9707(5) 0.0052(2) 0.0434(12) Uani 1 1 d . . . C14B C 0.4688(3) 1.0500(5) 0.0335(3) 0.0535(15) Uani 1 1 d . . . H14B H 0.5017 1.0973 0.0075 0.064 Uiso 1 1 calc R . . C15B C 0.4723(3) 1.0585(5) 0.1005(2) 0.0440(13) Uani 1 1 d . . . H15B H 0.5078 1.1123 0.1195 0.053 Uiso 1 1 calc R . . C16B C 0.3636(4) 0.8894(7) -0.0938(3) 0.076(2) Uani 1 1 d . . . H16D H 0.3741 0.8121 -0.0776 0.114 Uiso 1 1 calc R . . H16E H 0.3735 0.8913 -0.1400 0.114 Uiso 1 1 calc R . . H16F H 0.3076 0.9100 -0.0854 0.114 Uiso 1 1 calc R . . C17B C 0.2350(2) 1.1607(5) 0.2483(3) 0.0412(12) Uani 1 1 d . . . C18B C 0.1867(3) 1.1194(6) 0.1899(3) 0.0690(18) Uani 1 1 d . . . H18D H 0.1790 1.0363 0.1926 0.104 Uiso 1 1 calc R . . H18E H 0.2160 1.1382 0.1507 0.104 Uiso 1 1 calc R . . H18F H 0.1344 1.1576 0.1894 0.104 Uiso 1 1 calc R . . C19B C 0.1995(3) 1.1203(5) 0.3121(3) 0.0663(18) Uani 1 1 d . . . H19D H 0.1451 1.1508 0.3167 0.099 Uiso 1 1 calc R . . H19E H 0.2329 1.1481 0.3473 0.099 Uiso 1 1 calc R . . H19F H 0.1977 1.0364 0.3129 0.099 Uiso 1 1 calc R . . C20B C 0.2457(3) 1.2925(5) 0.2465(3) 0.0666(17) Uani 1 1 d . . . H20D H 0.2721 1.3145 0.2065 0.100 Uiso 1 1 calc R . . H20E H 0.2787 1.3168 0.2828 0.100 Uiso 1 1 calc R . . H20F H 0.1931 1.3295 0.2490 0.100 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 O1A 0.0393(19) 0.088(3) 0.064(3) -0.009(3) 0.005(2) -0.021(2) N1A 0.040(2) 0.059(3) 0.083(4) -0.019(3) -0.001(2) 0.007(2) C1A 0.025(2) 0.049(3) 0.042(3) -0.006(2) 0.0014(19) 0.004(2) O2A 0.0398(19) 0.060(2) 0.058(2) 0.010(2) -0.0085(17) 0.0009(18) C2A 0.032(2) 0.046(3) 0.048(3) -0.008(3) -0.003(2) 0.001(2) O3A 0.0268(16) 0.058(2) 0.062(2) -0.005(2) -0.0066(16) -0.0034(15) C3A 0.032(2) 0.048(3) 0.047(3) -0.009(3) -0.006(2) -0.001(2) O4A 0.064(2) 0.069(3) 0.040(2) 0.0021(19) 0.0036(17) 0.005(2) C4A 0.031(2) 0.045(3) 0.043(3) 0.000(2) 0.004(2) -0.004(2) C5A 0.030(2) 0.053(3) 0.049(3) -0.001(2) 0.000(2) -0.003(2) C6A 0.040(3) 0.056(4) 0.056(3) -0.005(3) 0.003(3) -0.005(3) C7A 0.051(3) 0.079(4) 0.058(3) 0.005(4) 0.015(3) -0.017(3) C8A 0.057(4) 0.075(5) 0.051(3) 0.008(3) 0.003(3) -0.009(3) C9A 0.047(3) 0.079(4) 0.043(3) -0.007(3) 0.005(2) -0.002(3) C10A 0.029(2) 0.036(3) 0.043(3) 0.000(2) -0.0020(19) -0.004(2) C11A 0.041(3) 0.041(3) 0.039(3) 0.002(2) -0.003(2) 0.009(2) C12A 0.038(2) 0.042(3) 0.056(3) -0.002(3) 0.001(2) 0.008(2) C13A 0.042(3) 0.042(3) 0.043(3) 0.000(2) 0.000(2) -0.007(2) C14A 0.048(3) 0.053(4) 0.048(3) 0.009(3) -0.003(2) 0.011(3) C15A 0.035(2) 0.056(4) 0.053(3) 0.001(3) -0.004(2) 0.014(2) C16A 0.084(5) 0.093(5) 0.055(4) -0.004(4) 0.024(3) 0.014(4) C17A 0.027(2) 0.063(4) 0.042(3) -0.003(3) -0.005(2) -0.009(2) C18A 0.047(3) 0.095(5) 0.051(3) -0.006(3) -0.009(3) -0.013(3) C19A 0.045(3) 0.101(5) 0.055(4) -0.005(4) 0.007(2) -0.015(3) C20A 0.046(3) 0.061(4) 0.098(5) 0.007(4) -0.010(3) -0.015(3) O1B 0.041(2) 0.073(3) 0.072(3) 0.011(2) 0.0008(18) 0.025(2) N1B 0.039(2) 0.048(3) 0.061(3) -0.007(2) -0.006(2) -0.006(2) C1B 0.025(2) 0.035(3) 0.039(2) -0.004(2) 0.0013(18) -0.0026(19) O2B 0.0328(16) 0.049(2) 0.064(2) -0.005(2) 0.0051(17) -0.0066(16) C2B 0.032(2) 0.043(3) 0.032(2) -0.008(2) -0.002(2) -0.001(2) O3B 0.0236(14) 0.041(2) 0.062(2) -0.0045(19) 0.0005(15) 0.0015(13) C3B 0.027(2) 0.037(3) 0.052(3) -0.007(3) 0.000(2) -0.003(2) O4B 0.073(3) 0.084(3) 0.034(2) 0.002(2) 0.0024(18) -0.022(2) C4B 0.030(2) 0.040(3) 0.031(2) -0.005(2) -0.002(2) -0.0026(19) C5B 0.035(2) 0.047(3) 0.041(3) 0.001(2) 0.000(2) 0.007(2) C6B 0.035(2) 0.054(3) 0.050(3) 0.009(3) -0.005(2) 0.003(2) C7B 0.055(3) 0.068(4) 0.058(3) 0.008(4) -0.017(3) 0.010(3) C8B 0.059(3) 0.076(4) 0.037(3) 0.010(3) -0.001(2) -0.003(3) C9B 0.045(3) 0.064(4) 0.039(3) 0.005(3) 0.002(2) -0.001(3) C10B 0.027(2) 0.033(3) 0.040(2) -0.001(2) -0.0009(18) 0.002(2) C11B 0.031(2) 0.050(4) 0.038(3) 0.003(2) 0.000(2) -0.006(2) C12B 0.044(3) 0.041(3) 0.041(3) -0.001(2) -0.004(2) -0.006(2) C13B 0.044(3) 0.051(3) 0.035(3) 0.002(3) 0.005(2) 0.005(2) C14B 0.047(3) 0.067(4) 0.047(3) 0.010(3) 0.012(3) -0.017(3) C15B 0.037(2) 0.045(3) 0.049(3) -0.004(3) -0.005(2) -0.011(2) C16B 0.069(4) 0.116(6) 0.043(3) -0.009(4) -0.002(3) -0.023(4) C17B 0.024(2) 0.053(3) 0.047(3) -0.003(3) 0.001(2) 0.008(2) C18B 0.043(3) 0.097(5) 0.068(4) -0.008(4) -0.008(3) -0.003(3) C19B 0.058(3) 0.081(5) 0.059(4) 0.005(4) 0.026(3) 0.018(3) C20B 0.042(3) 0.061(4) 0.096(5) -0.003(4) 0.003(3) 0.008(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 O1A C6A 1.427(6) . ? O1A H1A 0.89(6) . ? N1A C3A 1.144(6) . ? C1A C3A 1.470(7) . ? C1A C10A 1.543(6) . ? C1A C2A 1.548(6) . ? C1A C4A 1.550(7) . ? O2A C2A 1.191(6) . ? C2A O3A 1.334(6) . ? O3A C17A 1.495(5) . ? O4A C13A 1.381(6) . ? O4A C16A 1.420(6) . ? C4A C5A 1.538(6) . ? C4A C9A 1.543(6) . ? C4A H4A 0.9800 . ? C5A C6A 1.507(7) . ? C5A H5A1 0.9700 . ? C5A H5A2 0.9700 . ? C6A C7A 1.510(7) . ? C6A H6A 0.9800 . ? C7A C8A 1.532(7) . ? C7A H7A1 0.9700 . ? C7A H7A2 0.9700 . ? C8A C9A 1.519(8) . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C9A H9A1 0.9700 . ? C9A H9A2 0.9700 . ? C10A C15A 1.382(7) . ? C10A C11A 1.382(6) . ? C11A C12A 1.381(7) . ? C11A H11A 0.9300 . ? C12A C13A 1.369(7) . ? C12A H12A 0.9300 . ? C13A C14A 1.372(7) . ? C14A C15A 1.381(7) . ? C14A H14A 0.9300 . ? C15A H15A 0.9300 . ? C16A H16A 0.9600 . ? C16A H16B 0.9600 . ? C16A H16C 0.9600 . ? C17A C20A 1.494(8) . ? C17A C18A 1.508(7) . ? C17A C19A 1.511(7) . ? C18A H18A 0.9600 . ? C18A H18B 0.9600 . ? C18A H18C 0.9600 . ? C19A H19A 0.9600 . ? C19A H19B 0.9600 . ? C19A H19C 0.9600 . ? C20A H20A 0.9600 . ? C20A H20B 0.9600 . ? C20A H20C 0.9600 . ? O1B C6B 1.448(6) . ? O1B H1B 0.87(5) . ? N1B C3B 1.126(5) . ? C1B C3B 1.493(6) . ? C1B C10B 1.540(6) . ? C1B C4B 1.552(6) . ? C1B C2B 1.563(6) . ? O2B C2B 1.199(5) . ? C2B O3B 1.302(5) . ? O3B C17B 1.491(5) . ? O4B C13B 1.383(6) . ? O4B C16B 1.419(7) . ? C4B C9B 1.530(6) . ? C4B C5B 1.539(6) . ? C4B H4B 0.9800 . ? C5B C6B 1.513(6) . ? C5B H5B1 0.9700 . ? C5B H5B2 0.9700 . ? C6B C7B 1.517(7) . ? C6B H6B 0.9800 . ? C7B C8B 1.537(7) . ? C7B H7B1 0.9700 . ? C7B H7B2 0.9700 . ? C8B C9B 1.512(7) . ? C8B H8B1 0.9700 . ? C8B H8B2 0.9700 . ? C9B H9B1 0.9700 . ? C9B H9B2 0.9700 . ? C10B C15B 1.375(6) . ? C10B C11B 1.384(6) . ? C11B C12B 1.383(6) . ? C11B H11B 0.9300 . ? C12B C13B 1.371(6) . ? C12B H12B 0.9300 . ? C13B C14B 1.379(7) . ? C14B C15B 1.378(7) . ? C14B H14B 0.9300 . ? C15B H15B 0.9300 . ? C16B H16D 0.9600 . ? C16B H16E 0.9600 . ? C16B H16F 0.9600 . ? C17B C19B 1.503(7) . ? C17B C18B 1.509(7) . ? C17B C20B 1.516(7) . ? C18B H18D 0.9600 . ? C18B H18E 0.9600 . ? C18B H18F 0.9600 . ? C19B H19D 0.9600 . ? C19B H19E 0.9600 . ? C19B H19F 0.9600 . ? C20B H20D 0.9600 . ? C20B H20E 0.9600 . ? C20B H20F 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 C6A O1A H1A 108(4) . . ? C3A C1A C10A 110.2(4) . . ? C3A C1A C2A 110.0(4) . . ? C10A C1A C2A 103.8(3) . . ? C3A C1A C4A 109.3(4) . . ? C10A C1A C4A 111.1(4) . . ? C2A C1A C4A 112.4(4) . . ? O2A C2A O3A 128.3(4) . . ? O2A C2A C1A 123.2(5) . . ? O3A C2A C1A 108.5(4) . . ? C2A O3A C17A 122.4(4) . . ? N1A C3A C1A 177.6(5) . . ? C13A O4A C16A 117.3(4) . . ? C5A C4A C9A 109.4(4) . . ? C5A C4A C1A 111.5(4) . . ? C9A C4A C1A 112.9(4) . . ? C5A C4A H4A 107.6 . . ? C9A C4A H4A 107.6 . . ? C1A C4A H4A 107.6 . . ? C6A C5A C4A 112.6(4) . . ? C6A C5A H5A1 109.1 . . ? C4A C5A H5A1 109.1 . . ? C6A C5A H5A2 109.1 . . ? C4A C5A H5A2 109.1 . . ? H5A1 C5A H5A2 107.8 . . ? O1A C6A C5A 111.4(4) . . ? O1A C6A C7A 108.0(4) . . ? C5A C6A C7A 111.2(5) . . ? O1A C6A H6A 108.7 . . ? C5A C6A H6A 108.7 . . ? C7A C6A H6A 108.7 . . ? C6A C7A C8A 111.4(4) . . ? C6A C7A H7A1 109.4 . . ? C8A C7A H7A1 109.4 . . ? C6A C7A H7A2 109.4 . . ? C8A C7A H7A2 109.4 . . ? H7A1 C7A H7A2 108.0 . . ? C9A C8A C7A 111.0(5) . . ? C9A C8A H8A1 109.4 . . ? C7A C8A H8A1 109.4 . . ? C9A C8A H8A2 109.4 . . ? C7A C8A H8A2 109.4 . . ? H8A1 C8A H8A2 108.0 . . ? C8A C9A C4A 111.7(4) . . ? C8A C9A H9A1 109.3 . . ? C4A C9A H9A1 109.3 . . ? C8A C9A H9A2 109.3 . . ? C4A C9A H9A2 109.3 . . ? H9A1 C9A H9A2 107.9 . . ? C15A C10A C11A 117.6(4) . . ? C15A C10A C1A 122.4(4) . . ? C11A C10A C1A 120.0(4) . . ? C12A C11A C10A 122.1(5) . . ? C12A C11A H11A 119.0 . . ? C10A C11A H11A 119.0 . . ? C13A C12A C11A 118.9(5) . . ? C13A C12A H12A 120.5 . . ? C11A C12A H12A 120.5 . . ? C12A C13A C14A 120.4(5) . . ? C12A C13A O4A 124.5(5) . . ? C14A C13A O4A 115.1(5) . . ? C13A C14A C15A 120.1(5) . . ? C13A C14A H14A 119.9 . . ? C15A C14A H14A 119.9 . . ? C14A C15A C10A 120.8(5) . . ? C14A C15A H15A 119.6 . . ? C10A C15A H15A 119.6 . . ? O4A C16A H16A 109.5 . . ? O4A C16A H16B 109.5 . . ? H16A C16A H16B 109.5 . . ? O4A C16A H16C 109.5 . . ? H16A C16A H16C 109.5 . . ? H16B C16A H16C 109.5 . . ? C20A C17A O3A 102.2(4) . . ? C20A C17A C18A 111.1(5) . . ? O3A C17A C18A 111.9(4) . . ? C20A C17A C19A 112.4(5) . . ? O3A C17A C19A 107.8(4) . . ? C18A C17A C19A 111.1(5) . . ? C17A C18A H18A 109.5 . . ? C17A C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? C17A C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? C17A C19A H19A 109.5 . . ? C17A C19A H19B 109.5 . . ? H19A C19A H19B 109.5 . . ? C17A C19A H19C 109.5 . . ? H19A C19A H19C 109.5 . . ? H19B C19A H19C 109.5 . . ? C17A C20A H20A 109.5 . . ? C17A C20A H20B 109.5 . . ? H20A C20A H20B 109.5 . . ? C17A C20A H20C 109.5 . . ? H20A C20A H20C 109.5 . . ? H20B C20A H20C 109.5 . . ? C6B O1B H1B 105(3) . . ? C3B C1B C10B 109.8(4) . . ? C3B C1B C4B 109.1(4) . . ? C10B C1B C4B 112.3(4) . . ? C3B C1B C2B 109.0(4) . . ? C10B C1B C2B 105.9(4) . . ? C4B C1B C2B 110.7(4) . . ? O2B C2B O3B 128.2(4) . . ? O2B C2B C1B 121.0(4) . . ? O3B C2B C1B 110.5(4) . . ? C2B O3B C17B 122.3(3) . . ? N1B C3B C1B 176.2(5) . . ? C13B O4B C16B 117.2(4) . . ? C9B C4B C5B 109.5(4) . . ? C9B C4B C1B 112.9(4) . . ? C5B C4B C1B 111.1(4) . . ? C9B C4B H4B 107.7 . . ? C5B C4B H4B 107.7 . . ? C1B C4B H4B 107.7 . . ? C6B C5B C4B 111.0(4) . . ? C6B C5B H5B1 109.4 . . ? C4B C5B H5B1 109.4 . . ? C6B C5B H5B2 109.4 . . ? C4B C5B H5B2 109.4 . . ? H5B1 C5B H5B2 108.0 . . ? O1B C6B C5B 105.2(4) . . ? O1B C6B C7B 111.4(4) . . ? C5B C6B C7B 111.5(5) . . ? O1B C6B H6B 109.6 . . ? C5B C6B H6B 109.6 . . ? C7B C6B H6B 109.6 . . ? C6B C7B C8B 110.4(4) . . ? C6B C7B H7B1 109.6 . . ? C8B C7B H7B1 109.6 . . ? C6B C7B H7B2 109.6 . . ? C8B C7B H7B2 109.6 . . ? H7B1 C7B H7B2 108.1 . . ? C9B C8B C7B 110.6(4) . . ? C9B C8B H8B1 109.5 . . ? C7B C8B H8B1 109.5 . . ? C9B C8B H8B2 109.5 . . ? C7B C8B H8B2 109.5 . . ? H8B1 C8B H8B2 108.1 . . ? C8B C9B C4B 111.6(4) . . ? C8B C9B H9B1 109.3 . . ? C4B C9B H9B1 109.3 . . ? C8B C9B H9B2 109.3 . . ? C4B C9B H9B2 109.3 . . ? H9B1 C9B H9B2 108.0 . . ? C15B C10B C11B 118.1(4) . . ? C15B C10B C1B 122.6(4) . . ? C11B C10B C1B 119.2(4) . . ? C12B C11B C10B 121.7(5) . . ? C12B C11B H11B 119.1 . . ? C10B C11B H11B 119.1 . . ? C13B C12B C11B 118.6(5) . . ? C13B C12B H12B 120.7 . . ? C11B C12B H12B 120.7 . . ? C12B C13B C14B 120.9(5) . . ? C12B C13B O4B 124.3(5) . . ? C14B C13B O4B 114.8(5) . . ? C15B C14B C13B 119.4(5) . . ? C15B C14B H14B 120.3 . . ? C13B C14B H14B 120.3 . . ? C10B C15B C14B 121.2(5) . . ? C10B C15B H15B 119.4 . . ? C14B C15B H15B 119.4 . . ? O4B C16B H16D 109.5 . . ? O4B C16B H16E 109.5 . . ? H16D C16B H16E 109.5 . . ? O4B C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? O3B C17B C19B 110.8(4) . . ? O3B C17B C18B 108.4(4) . . ? C19B C17B C18B 113.0(4) . . ? O3B C17B C20B 101.7(4) . . ? C19B C17B C20B 111.7(5) . . ? C18B C17B C20B 110.5(5) . . ? C17B C18B H18D 109.5 . . ? C17B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? C17B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C17B C19B H19D 109.5 . . ? C17B C19B H19E 109.5 . . ? H19D C19B H19E 109.5 . . ? C17B C19B H19F 109.5 . . ? H19D C19B H19F 109.5 . . ? H19E C19B H19F 109.5 . . ? C17B C20B H20D 109.5 . . ? C17B C20B H20E 109.5 . . ? H20D C20B H20E 109.5 . . ? C17B C20B H20F 109.5 . . ? H20D C20B H20F 109.5 . . ? H20E C20B H20F 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 C3A C1A C2A O2A -144.8(5) . . . . ? C10A C1A C2A O2A 97.2(6) . . . . ? C4A C1A C2A O2A -22.9(7) . . . . ? C3A C1A C2A O3A 37.4(5) . . . . ? C10A C1A C2A O3A -80.5(5) . . . . ? C4A C1A C2A O3A 159.3(4) . . . . ? O2A C2A O3A C17A -21.9(8) . . . . ? C1A C2A O3A C17A 155.7(4) . . . . ? C10A C1A C3A N1A -87(14) . . . . ? C2A C1A C3A N1A 159(14) . . . . ? C4A C1A C3A N1A 35(14) . . . . ? C3A C1A C4A C5A -65.5(5) . . . . ? C10A C1A C4A C5A 56.3(5) . . . . ? C2A C1A C4A C5A 172.2(4) . . . . ? C3A C1A C4A C9A 58.2(5) . . . . ? C10A C1A C4A C9A -180.0(4) . . . . ? C2A C1A C4A C9A -64.1(5) . . . . ? C9A C4A C5A C6A 55.0(6) . . . . ? C1A C4A C5A C6A -179.4(4) . . . . ? C4A C5A C6A O1A -176.7(4) . . . . ? C4A C5A C6A C7A -56.1(6) . . . . ? O1A C6A C7A C8A 178.1(5) . . . . ? C5A C6A C7A C8A 55.6(7) . . . . ? C6A C7A C8A C9A -55.7(7) . . . . ? C7A C8A C9A C4A 55.7(6) . . . . ? C5A C4A C9A C8A -54.7(6) . . . . ? C1A C4A C9A C8A -179.5(4) . . . . ? C3A C1A C10A C15A 9.4(6) . . . . ? C2A C1A C10A C15A 127.1(5) . . . . ? C4A C1A C10A C15A -111.9(5) . . . . ? C3A C1A C10A C11A -169.7(4) . . . . ? C2A C1A C10A C11A -52.0(6) . . . . ? C4A C1A C10A C11A 69.0(5) . . . . ? C15A C10A C11A C12A 0.7(8) . . . . ? C1A C10A C11A C12A 179.9(5) . . . . ? C10A C11A C12A C13A 0.6(8) . . . . ? C11A C12A C13A C14A -0.7(8) . . . . ? C11A C12A C13A O4A 179.9(5) . . . . ? C16A O4A C13A C12A 2.2(8) . . . . ? C16A O4A C13A C14A -177.3(5) . . . . ? C12A C13A C14A C15A -0.7(8) . . . . ? O4A C13A C14A C15A 178.8(5) . . . . ? C13A C14A C15A C10A 2.1(8) . . . . ? C11A C10A C15A C14A -2.1(8) . . . . ? C1A C10A C15A C14A 178.8(5) . . . . ? C2A O3A C17A C20A -177.6(5) . . . . ? C2A O3A C17A C18A 63.5(6) . . . . ? C2A O3A C17A C19A -59.0(6) . . . . ? C3B C1B C2B O2B -153.3(5) . . . . ? C10B C1B C2B O2B 88.6(5) . . . . ? C4B C1B C2B O2B -33.3(6) . . . . ? C3B C1B C2B O3B 31.9(5) . . . . ? C10B C1B C2B O3B -86.1(5) . . . . ? C4B C1B C2B O3B 151.9(4) . . . . ? O2B C2B O3B C17B -8.0(8) . . . . ? C1B C2B O3B C17B 166.2(4) . . . . ? C10B C1B C3B N1B -109(8) . . . . ? C4B C1B C3B N1B 14(9) . . . . ? C2B C1B C3B N1B 135(8) . . . . ? C3B C1B C4B C9B 58.6(5) . . . . ? C10B C1B C4B C9B -179.5(4) . . . . ? C2B C1B C4B C9B -61.4(5) . . . . ? C3B C1B C4B C5B -64.9(5) . . . . ? C10B C1B C4B C5B 57.0(5) . . . . ? C2B C1B C4B C5B 175.1(4) . . . . ? C9B C4B C5B C6B 56.3(5) . . . . ? C1B C4B C5B C6B -178.2(4) . . . . ? C4B C5B C6B O1B -178.0(4) . . . . ? C4B C5B C6B C7B -57.1(5) . . . . ? O1B C6B C7B C8B 173.6(5) . . . . ? C5B C6B C7B C8B 56.4(6) . . . . ? C6B C7B C8B C9B -56.1(6) . . . . ? C7B C8B C9B C4B 57.1(6) . . . . ? C5B C4B C9B C8B -56.9(6) . . . . ? C1B C4B C9B C8B 178.7(4) . . . . ? C3B C1B C10B C15B 11.1(6) . . . . ? C4B C1B C10B C15B -110.4(5) . . . . ? C2B C1B C10B C15B 128.6(5) . . . . ? C3B C1B C10B C11B -171.0(4) . . . . ? C4B C1B C10B C11B 67.4(5) . . . . ? C2B C1B C10B C11B -53.5(6) . . . . ? C15B C10B C11B C12B 0.0(8) . . . . ? C1B C10B C11B C12B -177.9(4) . . . . ? C10B C11B C12B C13B 1.3(8) . . . . ? C11B C12B C13B C14B -1.8(8) . . . . ? C11B C12B C13B O4B -179.4(5) . . . . ? C16B O4B C13B C12B -3.0(8) . . . . ? C16B O4B C13B C14B 179.2(5) . . . . ? C12B C13B C14B C15B 1.0(9) . . . . ? O4B C13B C14B C15B 178.9(5) . . . . ? C11B C10B C15B C14B -0.8(8) . . . . ? C1B C10B C15B C14B 177.0(5) . . . . ? C13B C14B C15B C10B 0.3(9) . . . . ? C2B O3B C17B C19B 61.9(6) . . . . ? C2B O3B C17B C18B -62.7(6) . . . . ? C2B O3B C17B C20B -179.2(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.184 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.044 data_s1758rm _database_code_depnum_ccdc_archive 'CCDC 856193' #TrackingRef 'S1758RM.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'tert-Butyl-2-(4-chlorophenyl)-2-cyano-2- (6,6-dimethyl-2-oxooxepan-4-yl)acetate' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H26 Cl N O4' _chemical_formula_sum 'C21 H26 Cl N O4' _chemical_formula_weight 391.88 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' Cl Cl 0.1484 0.1585 '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/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.807(3) _cell_length_b 9.648(2) _cell_length_c 15.895(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.425(16) _cell_angle_gamma 90.00 _cell_volume 2108.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 10 _cell_measurement_theta_max 12 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Nicolet P3' _diffrn_measurement_method Wyckoff-Scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3870 _diffrn_reflns_av_R_equivalents 0.0698 _diffrn_reflns_av_sigmaI/netI 0.0854 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3706 _reflns_number_gt 1863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3/PC Data Collection System' _computing_cell_refinement 'Siemens P3/PC Data Collection System' _computing_data_reduction 'SHELXTL-plus, XDISK (Sheldrick, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-plus, XP (Sheldrick, 1991)' _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^)+(0.0553P)^2^+1.7000P] 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 0.0050(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3706 _refine_ls_number_parameters 250 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1831 _refine_ls_R_factor_gt 0.0912 _refine_ls_wR_factor_ref 0.1980 _refine_ls_wR_factor_gt 0.1749 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.178 _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 Cl1 Cl 0.11847(13) 0.16825(19) 0.26133(11) 0.0996(7) Uani 1 1 d . . . O1 O 0.4941(3) 0.1582(4) 0.5520(3) 0.0762(12) Uani 1 1 d . . . C1 C 0.2387(3) -0.1237(5) 0.5913(3) 0.0463(12) Uani 1 1 d . . . N1 N 0.1402(4) -0.0337(6) 0.7115(3) 0.0893(17) Uani 1 1 d . . . O2 O 0.5427(2) 0.0516(3) 0.6683(2) 0.0590(10) Uani 1 1 d . . . C2 C 0.2135(4) -0.2794(5) 0.5779(3) 0.0521(13) Uani 1 1 d . . . C3 C 0.1819(4) -0.0721(6) 0.6576(4) 0.0592(14) Uani 1 1 d . . . O3 O 0.1420(4) -0.3268(5) 0.5997(4) 0.135(2) Uani 1 1 d . . . O4 O 0.2785(3) -0.3409(3) 0.5397(2) 0.0615(10) Uani 1 1 d . . . C4 C 0.3477(3) -0.0978(5) 0.6185(3) 0.0443(12) Uani 1 1 d . . . H4 H 0.3852 -0.1359 0.5744 0.053 Uiso 1 1 calc R . . C5 C 0.3691(4) 0.0584(5) 0.6250(3) 0.0552(13) Uani 1 1 d . . . H5A H 0.3254 0.1069 0.5836 0.066 Uiso 1 1 calc R . . H5B H 0.3558 0.0906 0.6806 0.066 Uiso 1 1 calc R . . C6 C 0.4715(4) 0.0944(5) 0.6110(3) 0.0518(13) Uani 1 1 d . . . C7 C 0.5238(4) -0.0172(5) 0.7443(3) 0.0584(14) Uani 1 1 d . . . H7A H 0.4758 0.0361 0.7713 0.070 Uiso 1 1 calc R . . H7B H 0.5831 -0.0177 0.7822 0.070 Uiso 1 1 calc R . . C8 C 0.4871(3) -0.1664(5) 0.7332(3) 0.0504(12) Uani 1 1 d . . . C9 C 0.3793(3) -0.1738(5) 0.7010(3) 0.0489(12) Uani 1 1 d . . . H9A H 0.3419 -0.1369 0.7447 0.059 Uiso 1 1 calc R . . H9B H 0.3617 -0.2706 0.6936 0.059 Uiso 1 1 calc R . . C10 C 0.5493(4) -0.2451(6) 0.6752(3) 0.0715(17) Uani 1 1 d . . . H10A H 0.5322 -0.3415 0.6749 0.107 Uiso 1 1 calc R . . H10B H 0.6168 -0.2348 0.6951 0.107 Uiso 1 1 calc R . . H10C H 0.5383 -0.2087 0.6189 0.107 Uiso 1 1 calc R . . C11 C 0.4998(4) -0.2336(6) 0.8220(3) 0.0771(18) Uani 1 1 d . . . H11A H 0.4751 -0.3266 0.8187 0.116 Uiso 1 1 calc R . . H11B H 0.4646 -0.1807 0.8602 0.116 Uiso 1 1 calc R . . H11C H 0.5676 -0.2351 0.8421 0.116 Uiso 1 1 calc R . . C12 C 0.2054(3) -0.0506(5) 0.5060(3) 0.0435(11) Uani 1 1 d . . . C13 C 0.1272(3) 0.0370(5) 0.4986(3) 0.0559(13) Uani 1 1 d . . . H13 H 0.0921 0.0516 0.5449 0.067 Uiso 1 1 calc R . . C14 C 0.0995(4) 0.1045(6) 0.4231(4) 0.0643(15) Uani 1 1 d . . . H14 H 0.0465 0.1644 0.4189 0.077 Uiso 1 1 calc R . . C15 C 0.1505(4) 0.0823(6) 0.3554(3) 0.0600(14) Uani 1 1 d . . . C16 C 0.2284(4) -0.0066(6) 0.3608(3) 0.0641(15) Uani 1 1 d . . . H16 H 0.2624 -0.0230 0.3140 0.077 Uiso 1 1 calc R . . C17 C 0.2555(4) -0.0716(5) 0.4371(3) 0.0560(14) Uani 1 1 d . . . H17 H 0.3090 -0.1307 0.4414 0.067 Uiso 1 1 calc R . . C18 C 0.2695(5) -0.4857(6) 0.5117(3) 0.0733(18) Uani 1 1 d . . . C19 C 0.2599(7) -0.5817(7) 0.5819(5) 0.134(3) Uani 1 1 d U . . H19A H 0.2001 -0.5634 0.6061 0.201 Uiso 1 1 calc R . . H19B H 0.3136 -0.5692 0.6241 0.201 Uiso 1 1 calc R . . H19C H 0.2596 -0.6753 0.5613 0.201 Uiso 1 1 calc R . . C20 C 0.1989(8) -0.4972(10) 0.4423(6) 0.210(5) Uani 1 1 d U . . H20A H 0.1356 -0.5057 0.4622 0.315 Uiso 1 1 calc R . . H20B H 0.2121 -0.5777 0.4098 0.315 Uiso 1 1 calc R . . H20C H 0.2007 -0.4160 0.4075 0.315 Uiso 1 1 calc R . . C21 C 0.3708(8) -0.5140(10) 0.4865(7) 0.189(5) Uani 1 1 d U . . H21A H 0.3725 -0.6043 0.4614 0.283 Uiso 1 1 calc R . . H21B H 0.4168 -0.5102 0.5357 0.283 Uiso 1 1 calc R . . H21C H 0.3873 -0.4454 0.4465 0.283 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 0.1070(14) 0.0998(13) 0.0874(12) 0.0414(10) -0.0153(9) 0.0179(11) O1 0.087(3) 0.063(3) 0.077(3) 0.024(2) 0.001(2) -0.009(2) C1 0.042(3) 0.041(3) 0.055(3) 0.000(2) 0.002(2) 0.006(2) N1 0.078(4) 0.115(5) 0.075(3) -0.003(3) 0.010(3) 0.035(3) O2 0.056(2) 0.058(2) 0.061(2) 0.0113(18) -0.0052(17) -0.0111(18) C2 0.048(3) 0.047(3) 0.062(3) 0.005(3) 0.007(3) -0.003(3) C3 0.053(3) 0.058(4) 0.066(4) 0.003(3) 0.002(3) 0.014(3) O3 0.099(4) 0.070(3) 0.250(7) -0.030(4) 0.091(4) -0.028(3) O4 0.076(3) 0.043(2) 0.068(2) -0.0094(18) 0.0172(19) -0.0007(19) C4 0.040(3) 0.036(3) 0.055(3) -0.001(2) -0.003(2) 0.003(2) C5 0.058(3) 0.039(3) 0.065(3) 0.002(2) -0.008(3) 0.005(3) C6 0.062(4) 0.037(3) 0.055(3) 0.001(3) -0.005(3) 0.000(3) C7 0.064(4) 0.057(3) 0.050(3) 0.003(3) -0.012(3) -0.009(3) C8 0.051(3) 0.047(3) 0.051(3) 0.004(2) -0.004(2) -0.002(3) C9 0.051(3) 0.042(3) 0.052(3) 0.002(2) -0.002(2) 0.001(2) C10 0.068(4) 0.067(4) 0.077(4) -0.008(3) -0.007(3) 0.017(3) C11 0.082(4) 0.073(4) 0.070(4) 0.020(3) -0.019(3) -0.006(3) C12 0.035(3) 0.041(3) 0.053(3) -0.001(2) -0.003(2) 0.003(2) C13 0.046(3) 0.052(3) 0.069(3) -0.004(3) -0.002(3) 0.004(3) C14 0.056(3) 0.055(3) 0.078(4) 0.003(3) -0.014(3) 0.014(3) C15 0.059(4) 0.051(3) 0.066(4) 0.013(3) -0.013(3) 0.003(3) C16 0.064(4) 0.066(4) 0.062(3) 0.009(3) 0.005(3) 0.001(3) C17 0.054(3) 0.057(3) 0.057(3) 0.005(3) 0.001(3) 0.012(3) C18 0.121(6) 0.043(3) 0.056(3) -0.010(3) 0.004(3) 0.005(3) C19 0.232(9) 0.062(4) 0.106(5) 0.007(4) -0.001(6) 0.026(5) C20 0.315(11) 0.106(7) 0.175(8) -0.051(6) -0.148(8) 0.016(7) C21 0.206(10) 0.124(7) 0.247(10) -0.074(7) 0.076(8) 0.019(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C15 1.731(5) . ? O1 C6 1.188(5) . ? C1 C3 1.460(7) . ? C1 C4 1.546(6) . ? C1 C2 1.553(7) . ? C1 C12 1.560(6) . ? N1 C3 1.137(6) . ? O2 C6 1.341(6) . ? O2 C7 1.424(5) . ? C2 O3 1.169(6) . ? C2 O4 1.275(6) . ? O4 C18 1.468(6) . ? C4 C9 1.531(6) . ? C4 C5 1.537(6) . ? C4 H4 0.9800 . ? C5 C6 1.493(7) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C7 C8 1.530(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C10 1.522(7) . ? C8 C9 1.530(6) . ? C8 C11 1.547(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C17 1.365(6) . ? C12 C13 1.367(6) . ? C13 C14 1.387(7) . ? C13 H13 0.9300 . ? C14 C15 1.358(7) . ? C14 H14 0.9300 . ? C15 C16 1.371(7) . ? C16 C17 1.385(7) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C20 1.406(9) . ? C18 C19 1.466(8) . ? C18 C21 1.516(11) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 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 C3 C1 C4 108.6(4) . . ? C3 C1 C2 107.5(4) . . ? C4 C1 C2 113.2(4) . . ? C3 C1 C12 109.8(4) . . ? C4 C1 C12 111.7(4) . . ? C2 C1 C12 105.9(4) . . ? C6 O2 C7 122.5(4) . . ? O3 C2 O4 127.6(5) . . ? O3 C2 C1 121.4(5) . . ? O4 C2 C1 110.9(4) . . ? N1 C3 C1 177.4(6) . . ? C2 O4 C18 123.0(4) . . ? C9 C4 C5 112.0(4) . . ? C9 C4 C1 110.6(4) . . ? C5 C4 C1 110.7(4) . . ? C9 C4 H4 107.8 . . ? C5 C4 H4 107.8 . . ? C1 C4 H4 107.8 . . ? C6 C5 C4 113.4(4) . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5B 108.9 . . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? O1 C6 O2 117.8(5) . . ? O1 C6 C5 124.1(5) . . ? O2 C6 C5 118.1(4) . . ? O2 C7 C8 115.3(4) . . ? O2 C7 H7A 108.5 . . ? C8 C7 H7A 108.5 . . ? O2 C7 H7B 108.5 . . ? C8 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C10 C8 C9 111.2(4) . . ? C10 C8 C7 109.8(4) . . ? C9 C8 C7 112.5(4) . . ? C10 C8 C11 108.8(4) . . ? C9 C8 C11 108.0(4) . . ? C7 C8 C11 106.4(4) . . ? C8 C9 C4 117.0(4) . . ? C8 C9 H9A 108.0 . . ? C4 C9 H9A 108.0 . . ? C8 C9 H9B 108.0 . . ? C4 C9 H9B 108.0 . . ? H9A C9 H9B 107.3 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C17 C12 C13 118.7(5) . . ? C17 C12 C1 120.0(4) . . ? C13 C12 C1 121.3(4) . . ? C12 C13 C14 121.0(5) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C13 119.4(5) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 120.8(5) . . ? C14 C15 Cl1 120.0(4) . . ? C16 C15 Cl1 119.3(5) . . ? C15 C16 C17 118.9(5) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C12 C17 C16 121.3(5) . . ? C12 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C20 C18 C19 116.2(8) . . ? C20 C18 O4 110.2(6) . . ? C19 C18 O4 112.4(5) . . ? C20 C18 C21 111.6(7) . . ? C19 C18 C21 103.9(7) . . ? O4 C18 C21 101.4(6) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C3 C1 C2 O3 20.1(7) . . . . ? C4 C1 C2 O3 140.1(6) . . . . ? C12 C1 C2 O3 -97.2(6) . . . . ? C3 C1 C2 O4 -161.5(4) . . . . ? C4 C1 C2 O4 -41.5(6) . . . . ? C12 C1 C2 O4 81.1(5) . . . . ? C4 C1 C3 N1 -38(14) . . . . ? C2 C1 C3 N1 85(14) . . . . ? C12 C1 C3 N1 -160(14) . . . . ? O3 C2 O4 C18 4.0(9) . . . . ? C1 C2 O4 C18 -174.3(4) . . . . ? C3 C1 C4 C9 60.3(5) . . . . ? C2 C1 C4 C9 -59.0(5) . . . . ? C12 C1 C4 C9 -178.4(4) . . . . ? C3 C1 C4 C5 -64.4(5) . . . . ? C2 C1 C4 C5 176.3(4) . . . . ? C12 C1 C4 C5 56.9(5) . . . . ? C9 C4 C5 C6 82.8(5) . . . . ? C1 C4 C5 C6 -153.2(4) . . . . ? C7 O2 C6 O1 175.6(4) . . . . ? C7 O2 C6 C5 -4.8(6) . . . . ? C4 C5 C6 O1 112.8(6) . . . . ? C4 C5 C6 O2 -66.8(6) . . . . ? C6 O2 C7 C8 72.4(6) . . . . ? O2 C7 C8 C10 46.4(6) . . . . ? O2 C7 C8 C9 -78.0(5) . . . . ? O2 C7 C8 C11 164.0(4) . . . . ? C10 C8 C9 C4 -67.8(6) . . . . ? C7 C8 C9 C4 55.8(6) . . . . ? C11 C8 C9 C4 172.9(4) . . . . ? C5 C4 C9 C8 -60.0(6) . . . . ? C1 C4 C9 C8 176.0(4) . . . . ? C3 C1 C12 C17 172.9(5) . . . . ? C4 C1 C12 C17 52.4(6) . . . . ? C2 C1 C12 C17 -71.3(5) . . . . ? C3 C1 C12 C13 -5.9(6) . . . . ? C4 C1 C12 C13 -126.5(5) . . . . ? C2 C1 C12 C13 109.9(5) . . . . ? C17 C12 C13 C14 -0.6(7) . . . . ? C1 C12 C13 C14 178.3(4) . . . . ? C12 C13 C14 C15 0.4(8) . . . . ? C13 C14 C15 C16 0.5(8) . . . . ? C13 C14 C15 Cl1 -178.7(4) . . . . ? C14 C15 C16 C17 -1.2(8) . . . . ? Cl1 C15 C16 C17 177.9(4) . . . . ? C13 C12 C17 C16 -0.2(7) . . . . ? C1 C12 C17 C16 -179.1(5) . . . . ? C15 C16 C17 C12 1.1(8) . . . . ? C2 O4 C18 C20 71.8(8) . . . . ? C2 O4 C18 C19 -59.5(8) . . . . ? C2 O4 C18 C21 -169.8(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.512 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.058 data_s1840lm _database_code_depnum_ccdc_archive 'CCDC 856194' #TrackingRef 's1840lm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'tert-Butyl-2-(4-chlorophenyl)-2-cyano-2-(3-oxocyclohexyl)acetate' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H22 Cl N O3' _chemical_formula_sum 'C19 H22 Cl N O3' _chemical_formula_weight 347.83 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' Cl Cl 0.1484 0.1585 '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/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.2391(11) _cell_length_b 13.5132(11) _cell_length_c 12.6257(11) _cell_angle_alpha 90.00 _cell_angle_beta 118.770(4) _cell_angle_gamma 90.00 _cell_volume 1830.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4631 _cell_measurement_theta_min 1.90 _cell_measurement_theta_max 30.61 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.37 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.225 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7068 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Kappa APEX II Duo' _diffrn_measurement_method 'Omega + Phi-Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 38134 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 30.61 _reflns_number_total 5623 _reflns_number_gt 4631 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II Software Suite, 2008' _computing_cell_refinement 'APEX II Software Suite, 2008' _computing_data_reduction 'APEX II Software Suite, 2008' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-plus, (Sheldrick, 1991)' _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^)+(0.0415P)^2^+0.6299P] 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_number_reflns 5623 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.0989 _refine_ls_wR_factor_gt 0.0955 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 Cl1 Cl 0.12210(3) 0.00802(2) 0.79119(3) 0.02869(8) Uani 1 1 d . . . C1 C -0.37296(9) -0.10391(7) 0.36716(9) 0.01511(18) Uani 1 1 d . . . N1 N -0.34494(9) -0.20150(7) 0.20249(9) 0.02152(19) Uani 1 1 d . . . O1 O -0.36595(10) -0.37366(9) 0.62080(9) 0.0457(3) Uani 1 1 d . . . O2 O -0.51874(8) 0.02321(7) 0.35109(8) 0.02525(18) Uani 1 1 d . . . C2 C -0.35719(9) -0.15575(7) 0.27223(9) 0.01624(19) Uani 1 1 d . . . O3 O -0.42895(7) 0.02983(5) 0.23089(7) 0.01697(15) Uani 1 1 d . . . C3 C -0.44041(10) -0.17469(8) 0.41425(9) 0.01725(19) Uani 1 1 d . . . H3 H -0.4542 -0.1376 0.4754 0.021 Uiso 1 1 calc R . . C4 C -0.35887(10) -0.26493(8) 0.47763(10) 0.0192(2) Uani 1 1 d . . . H4A H -0.3387 -0.3001 0.4204 0.023 Uiso 1 1 calc R . . H4B H -0.2796 -0.2423 0.5466 0.023 Uiso 1 1 calc R . . C5 C -0.42258(11) -0.33567(8) 0.52301(10) 0.0223(2) Uani 1 1 d . . . C6 C -0.55674(11) -0.36024(9) 0.43787(11) 0.0258(2) Uani 1 1 d . . . H6A H -0.5945 -0.3899 0.4844 0.031 Uiso 1 1 calc R . . H6B H -0.5604 -0.4102 0.3789 0.031 Uiso 1 1 calc R . . C7 C -0.63309(11) -0.26956(10) 0.36936(12) 0.0291(3) Uani 1 1 d . . . H7A H -0.7152 -0.2915 0.3041 0.035 Uiso 1 1 calc R . . H7B H -0.6477 -0.2273 0.4254 0.035 Uiso 1 1 calc R . . C8 C -0.56742(10) -0.20900(9) 0.31468(10) 0.0236(2) Uani 1 1 d . . . H8A H -0.6190 -0.1508 0.2719 0.028 Uiso 1 1 calc R . . H8B H -0.5564 -0.2498 0.2553 0.028 Uiso 1 1 calc R . . C9 C -0.24591(9) -0.07231(7) 0.47073(9) 0.01485(18) Uani 1 1 d . . . C10 C -0.13504(10) -0.10735(8) 0.47952(10) 0.0173(2) Uani 1 1 d . . . H10 H -0.1370 -0.1477 0.4170 0.021 Uiso 1 1 calc R . . C11 C -0.02131(10) -0.08383(8) 0.57887(10) 0.0200(2) Uani 1 1 d . . . H11 H 0.0543 -0.1090 0.5857 0.024 Uiso 1 1 calc R . . C12 C -0.01996(10) -0.02321(8) 0.66752(10) 0.0200(2) Uani 1 1 d . . . C13 C -0.12861(11) 0.01361(9) 0.66037(10) 0.0226(2) Uani 1 1 d . . . H13 H -0.1257 0.0558 0.7218 0.027 Uiso 1 1 calc R . . C14 C -0.24209(10) -0.01193(8) 0.56211(10) 0.0205(2) Uani 1 1 d . . . H14 H -0.3175 0.0118 0.5571 0.025 Uiso 1 1 calc R . . C15 C -0.45162(10) -0.00902(8) 0.31455(10) 0.01694(19) Uani 1 1 d . . . C16 C -0.49299(10) 0.12176(8) 0.16508(10) 0.0189(2) Uani 1 1 d . . . C17 C -0.43407(11) 0.13902(8) 0.08518(11) 0.0240(2) Uani 1 1 d . . . H17A H -0.3447 0.1514 0.1357 0.036 Uiso 1 1 calc R . . H17B H -0.4731 0.1965 0.0332 0.036 Uiso 1 1 calc R . . H17C H -0.4463 0.0804 0.0350 0.036 Uiso 1 1 calc R . . C18 C -0.63113(11) 0.10028(10) 0.09104(12) 0.0273(2) Uani 1 1 d . . . H18A H -0.6437 0.0434 0.0382 0.041 Uiso 1 1 calc R . . H18B H -0.6737 0.1583 0.0418 0.041 Uiso 1 1 calc R . . H18C H -0.6653 0.0852 0.1453 0.041 Uiso 1 1 calc R . . C19 C -0.46403(13) 0.20664(9) 0.25357(12) 0.0305(3) Uani 1 1 d . . . H19A H -0.5053 0.1950 0.3024 0.046 Uiso 1 1 calc R . . H19B H -0.4943 0.2688 0.2088 0.046 Uiso 1 1 calc R . . H19C H -0.3737 0.2109 0.3066 0.046 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 0.02054(13) 0.03046(15) 0.02338(14) -0.00177(11) 0.00123(11) -0.00516(10) C1 0.0139(4) 0.0168(4) 0.0147(4) 0.0013(3) 0.0069(4) 0.0005(3) N1 0.0231(5) 0.0218(4) 0.0182(4) 0.0001(3) 0.0087(4) 0.0007(4) O1 0.0363(6) 0.0582(7) 0.0313(5) 0.0203(5) 0.0073(4) -0.0129(5) O2 0.0246(4) 0.0288(4) 0.0276(4) 0.0043(3) 0.0168(4) 0.0080(3) C2 0.0156(4) 0.0162(4) 0.0152(4) 0.0033(3) 0.0060(4) 0.0001(3) O3 0.0166(3) 0.0155(3) 0.0191(4) 0.0042(3) 0.0089(3) 0.0032(3) C3 0.0155(4) 0.0201(5) 0.0160(5) 0.0026(4) 0.0075(4) -0.0019(4) C4 0.0158(5) 0.0214(5) 0.0183(5) 0.0051(4) 0.0067(4) -0.0015(4) C5 0.0225(5) 0.0224(5) 0.0219(5) 0.0039(4) 0.0106(4) -0.0032(4) C6 0.0219(5) 0.0276(6) 0.0265(6) 0.0041(5) 0.0103(5) -0.0072(4) C7 0.0175(5) 0.0361(6) 0.0308(6) 0.0087(5) 0.0094(5) -0.0046(5) C8 0.0146(5) 0.0302(6) 0.0209(5) 0.0069(4) 0.0045(4) -0.0035(4) C9 0.0147(4) 0.0147(4) 0.0146(4) 0.0012(3) 0.0067(4) -0.0004(3) C10 0.0173(5) 0.0157(4) 0.0193(5) -0.0003(4) 0.0091(4) -0.0001(4) C11 0.0163(5) 0.0184(5) 0.0233(5) 0.0013(4) 0.0079(4) 0.0006(4) C12 0.0177(5) 0.0194(5) 0.0172(5) 0.0019(4) 0.0039(4) -0.0037(4) C13 0.0239(5) 0.0234(5) 0.0185(5) -0.0039(4) 0.0087(4) -0.0013(4) C14 0.0185(5) 0.0240(5) 0.0202(5) -0.0027(4) 0.0101(4) 0.0009(4) C15 0.0147(4) 0.0179(4) 0.0172(5) 0.0012(4) 0.0069(4) 0.0009(4) C16 0.0192(5) 0.0134(4) 0.0203(5) 0.0030(4) 0.0065(4) 0.0038(4) C17 0.0270(6) 0.0189(5) 0.0244(5) 0.0059(4) 0.0111(5) 0.0006(4) C18 0.0182(5) 0.0295(6) 0.0276(6) 0.0024(5) 0.0057(5) 0.0060(4) C19 0.0392(7) 0.0180(5) 0.0316(6) -0.0047(5) 0.0149(6) 0.0002(5) _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 Cl1 C12 1.7396(11) . ? C1 C2 1.4790(14) . ? C1 C9 1.5339(14) . ? C1 C15 1.5482(14) . ? C1 C3 1.5563(14) . ? N1 C2 1.1432(14) . ? O1 C5 1.2019(15) . ? O2 C15 1.2009(13) . ? O3 C15 1.3231(13) . ? O3 C16 1.4902(12) . ? C3 C8 1.5267(15) . ? C3 C4 1.5344(15) . ? C3 H3 1.0000 . ? C4 C5 1.5100(15) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5043(16) . ? C6 C7 1.5314(18) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5253(16) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.3903(14) . ? C9 C14 1.3954(15) . ? C10 C11 1.3897(15) . ? C10 H10 0.9500 . ? C11 C12 1.3807(16) . ? C11 H11 0.9500 . ? C12 C13 1.3815(17) . ? C13 C14 1.3887(16) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C16 C17 1.5140(16) . ? C16 C18 1.5150(16) . ? C16 C19 1.5193(16) . ? 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 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 C2 C1 C9 110.40(8) . . ? C2 C1 C15 109.96(8) . . ? C9 C1 C15 107.52(8) . . ? C2 C1 C3 108.58(8) . . ? C9 C1 C3 110.61(8) . . ? C15 C1 C3 109.77(8) . . ? N1 C2 C1 175.52(11) . . ? C15 O3 C16 121.32(8) . . ? C8 C3 C4 109.69(9) . . ? C8 C3 C1 112.90(8) . . ? C4 C3 C1 110.87(8) . . ? C8 C3 H3 107.7 . . ? C4 C3 H3 107.7 . . ? C1 C3 H3 107.7 . . ? C5 C4 C3 112.08(9) . . ? C5 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? C5 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? O1 C5 C6 122.09(11) . . ? O1 C5 C4 120.82(11) . . ? C6 C5 C4 117.00(9) . . ? C5 C6 C7 112.73(10) . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 111.95(10) . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C7 C8 C3 109.86(9) . . ? C7 C8 H8A 109.7 . . ? C3 C8 H8A 109.7 . . ? C7 C8 H8B 109.7 . . ? C3 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C10 C9 C14 119.35(10) . . ? C10 C9 C1 121.55(9) . . ? C14 C9 C1 118.98(9) . . ? C11 C10 C9 120.61(10) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 118.90(10) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 C13 121.68(10) . . ? C11 C12 Cl1 119.23(9) . . ? C13 C12 Cl1 119.09(9) . . ? C12 C13 C14 119.09(10) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C13 C14 C9 120.34(10) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? O2 C15 O3 127.43(10) . . ? O2 C15 C1 122.32(10) . . ? O3 C15 C1 110.20(8) . . ? O3 C16 C17 102.04(8) . . ? O3 C16 C18 108.40(9) . . ? C17 C16 C18 111.49(10) . . ? O3 C16 C19 110.20(9) . . ? C17 C16 C19 110.87(10) . . ? C18 C16 C19 113.23(10) . . ? 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 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C9 C1 C2 N1 93.7(14) . . . . ? C15 C1 C2 N1 -147.9(14) . . . . ? C3 C1 C2 N1 -27.7(14) . . . . ? C2 C1 C3 C8 -58.45(11) . . . . ? C9 C1 C3 C8 -179.73(9) . . . . ? C15 C1 C3 C8 61.78(12) . . . . ? C2 C1 C3 C4 65.09(11) . . . . ? C9 C1 C3 C4 -56.19(11) . . . . ? C15 C1 C3 C4 -174.68(8) . . . . ? C8 C3 C4 C5 -53.94(12) . . . . ? C1 C3 C4 C5 -179.30(9) . . . . ? C3 C4 C5 O1 -137.99(13) . . . . ? C3 C4 C5 C6 45.36(14) . . . . ? O1 C5 C6 C7 141.35(14) . . . . ? C4 C5 C6 C7 -42.05(15) . . . . ? C5 C6 C7 C8 48.11(15) . . . . ? C6 C7 C8 C3 -58.81(14) . . . . ? C4 C3 C8 C7 61.34(12) . . . . ? C1 C3 C8 C7 -174.48(10) . . . . ? C2 C1 C9 C10 -11.72(13) . . . . ? C15 C1 C9 C10 -131.67(10) . . . . ? C3 C1 C9 C10 108.48(11) . . . . ? C2 C1 C9 C14 172.36(9) . . . . ? C15 C1 C9 C14 52.40(12) . . . . ? C3 C1 C9 C14 -67.44(12) . . . . ? C14 C9 C10 C11 0.85(16) . . . . ? C1 C9 C10 C11 -175.06(9) . . . . ? C9 C10 C11 C12 -1.44(16) . . . . ? C10 C11 C12 C13 0.66(17) . . . . ? C10 C11 C12 Cl1 -179.12(8) . . . . ? C11 C12 C13 C14 0.71(17) . . . . ? Cl1 C12 C13 C14 -179.51(9) . . . . ? C12 C13 C14 C9 -1.32(17) . . . . ? C10 C9 C14 C13 0.55(16) . . . . ? C1 C9 C14 C13 176.56(10) . . . . ? C16 O3 C15 O2 -2.83(17) . . . . ? C16 O3 C15 C1 179.76(8) . . . . ? C2 C1 C15 O2 149.00(11) . . . . ? C9 C1 C15 O2 -90.77(12) . . . . ? C3 C1 C15 O2 29.61(14) . . . . ? C2 C1 C15 O3 -33.43(11) . . . . ? C9 C1 C15 O3 86.80(10) . . . . ? C3 C1 C15 O3 -152.82(9) . . . . ? C15 O3 C16 C17 177.67(9) . . . . ? C15 O3 C16 C18 -64.57(12) . . . . ? C15 O3 C16 C19 59.85(13) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.61 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.707 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.065 data_s1841lm _database_code_depnum_ccdc_archive 'CCDC 856195' #TrackingRef 's1841lm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'tert-Butyl-2-(4-bromophenyl)-2-cyano-2-(3,3-dimethyl-5-oxocyclo- hexyl)acetate' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H26 Br N O3' _chemical_formula_sum 'C21 H26 Br N O3' _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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 19.981(2) _cell_length_b 10.4357(12) _cell_length_c 20.133(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.963(7) _cell_angle_gamma 90.00 _cell_volume 4055.8(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4780 _cell_measurement_theta_min 1.67 _cell_measurement_theta_max 25.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 2.046 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6649 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Kappa APEXII Duo' _diffrn_measurement_method 'Omega + Phi Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 44613 _diffrn_reflns_av_R_equivalents 0.0939 _diffrn_reflns_av_sigmaI/netI 0.0868 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.50 _reflns_number_total 7529 _reflns_number_gt 4780 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII Software Suite, 2008' _computing_cell_refinement 'Bruker APEXII Software Suite, 2008' _computing_data_reduction 'Bruker APEXII Software Suite, 2008' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-plus, XP (Sheldrick, 1991)' _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^)+(0.0475P)^2^+7.9823P] 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_number_reflns 7529 _refine_ls_number_parameters 467 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1147 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1349 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 Br1A Br 0.69500(3) 0.05258(5) 0.16469(3) 0.02435(16) Uani 1 1 d . . . N1A N 0.7282(2) 0.7681(4) 0.1547(2) 0.0163(10) Uani 1 1 d . . . C1A C 0.6268(3) 0.6194(5) 0.0889(2) 0.0146(12) Uani 1 1 d . . . O1A O 0.4358(2) 0.9263(4) 0.04088(19) 0.0317(10) Uani 1 1 d . . . O2A O 0.57973(18) 0.5510(4) -0.02797(17) 0.0217(8) Uani 1 1 d . . . C2A C 0.6845(3) 0.7053(5) 0.1250(2) 0.0125(11) Uani 1 1 d . . . O3A O 0.65934(18) 0.7117(3) -0.00570(16) 0.0172(8) Uani 1 1 d . . . C3A C 0.5578(3) 0.6759(5) 0.1017(2) 0.0155(12) Uani 1 1 d . . . H3A H 0.5190 0.6155 0.0817 0.019 Uiso 1 1 calc R . . C4A C 0.5411(3) 0.8062(5) 0.0656(3) 0.0194(13) Uani 1 1 d . . . H4A1 H 0.5828 0.8613 0.0783 0.023 Uiso 1 1 calc R . . H4A2 H 0.5295 0.7929 0.0152 0.023 Uiso 1 1 calc R . . C5A C 0.4820(3) 0.8737(5) 0.0839(3) 0.0209(13) Uani 1 1 d . . . C6A C 0.4852(3) 0.8775(5) 0.1598(3) 0.0229(13) Uani 1 1 d . . . H6A1 H 0.4405 0.9102 0.1655 0.027 Uiso 1 1 calc R . . H6A2 H 0.5219 0.9385 0.1828 0.027 Uiso 1 1 calc R . . C7A C 0.5000(3) 0.7470(5) 0.1954(3) 0.0171(12) Uani 1 1 d . . . C8A C 0.5638(3) 0.6893(5) 0.1783(2) 0.0155(12) Uani 1 1 d . . . H8A1 H 0.6044 0.7438 0.1990 0.019 Uiso 1 1 calc R . . H8A2 H 0.5725 0.6035 0.1999 0.019 Uiso 1 1 calc R . . C9A C 0.5145(3) 0.7642(6) 0.2724(3) 0.0252(14) Uani 1 1 d . . . H9A1 H 0.5218 0.6803 0.2949 0.038 Uiso 1 1 calc R . . H9A2 H 0.4750 0.8069 0.2834 0.038 Uiso 1 1 calc R . . H9A3 H 0.5562 0.8168 0.2888 0.038 Uiso 1 1 calc R . . C10A C 0.4366(3) 0.6584(6) 0.1696(3) 0.0290(14) Uani 1 1 d . . . H10A H 0.4480 0.5720 0.1880 0.043 Uiso 1 1 calc R . . H10B H 0.4243 0.6553 0.1192 0.043 Uiso 1 1 calc R . . H10C H 0.3974 0.6919 0.1851 0.043 Uiso 1 1 calc R . . C11A C 0.6407(3) 0.4823(5) 0.1145(2) 0.0120(11) Uani 1 1 d . . . C12A C 0.5919(3) 0.3871(5) 0.0902(3) 0.0178(12) Uani 1 1 d . . . H12A H 0.5479 0.4100 0.0616 0.021 Uiso 1 1 calc R . . C13A C 0.6065(3) 0.2580(5) 0.1072(3) 0.0201(12) Uani 1 1 d . . . H13A H 0.5730 0.1930 0.0907 0.024 Uiso 1 1 calc R . . C14A C 0.6711(3) 0.2290(5) 0.1486(3) 0.0158(12) Uani 1 1 d . . . C15A C 0.7189(3) 0.3202(5) 0.1758(3) 0.0191(12) Uani 1 1 d . . . H15A H 0.7631 0.2977 0.2044 0.023 Uiso 1 1 calc R . . C16A C 0.7009(3) 0.4466(5) 0.1605(2) 0.015 Uiso 1 1 d . . . H16A H 0.7318 0.5117 0.1830 0.023 Uiso 1 1 calc R . . C17A C 0.6189(3) 0.6216(5) 0.0106(3) 0.0159(12) Uani 1 1 d . . . C18A C 0.6611(3) 0.7332(5) -0.0790(2) 0.0155(12) Uani 1 1 d . . . C19A C 0.6951(3) 0.6166(5) -0.1009(3) 0.0244(13) Uani 1 1 d . . . H19A H 0.7404 0.6027 -0.0685 0.037 Uiso 1 1 calc R . . H19B H 0.7012 0.6304 -0.1471 0.037 Uiso 1 1 calc R . . H19C H 0.6658 0.5413 -0.1011 0.037 Uiso 1 1 calc R . . C20A C 0.5889(3) 0.7585(6) -0.1234(3) 0.0257(14) Uani 1 1 d . . . H20A H 0.5613 0.6799 -0.1274 0.039 Uiso 1 1 calc R . . H20B H 0.5915 0.7859 -0.1692 0.039 Uiso 1 1 calc R . . H20C H 0.5671 0.8260 -0.1024 0.039 Uiso 1 1 calc R . . C21A C 0.7058(3) 0.8502(5) -0.0725(3) 0.0278(14) Uani 1 1 d . . . H21A H 0.6846 0.9203 -0.0526 0.042 Uiso 1 1 calc R . . H21B H 0.7103 0.8755 -0.1180 0.042 Uiso 1 1 calc R . . H21C H 0.7518 0.8313 -0.0425 0.042 Uiso 1 1 calc R . . Br1B Br 0.16788(3) 0.05684(5) 0.19257(3) 0.02329(16) Uani 1 1 d . . . N1B N 0.1550(2) 0.7697(4) 0.2294(2) 0.0154(10) Uani 1 1 d . . . O1B O 0.0391(2) 0.9269(4) -0.06289(19) 0.0314(10) Uani 1 1 d . . . C1B C 0.0871(3) 0.6240(5) 0.1281(2) 0.0130(11) Uani 1 1 d . . . O2B O -0.03139(18) 0.5591(4) 0.08084(17) 0.0195(8) Uani 1 1 d . . . C2B C 0.1234(3) 0.7073(5) 0.1862(3) 0.0131(11) Uani 1 1 d . . . O3B O -0.00782(17) 0.7183(3) 0.15996(17) 0.0165(8) Uani 1 1 d . . . C3B C 0.0998(3) 0.6799(5) 0.0599(3) 0.0161(12) Uani 1 1 d . . . H3B H 0.0797 0.6191 0.0215 0.019 Uiso 1 1 calc R . . C4B C 0.0636(3) 0.8104(5) 0.0429(3) 0.0187(12) Uani 1 1 d . . . H4B1 H 0.0128 0.7975 0.0311 0.022 Uiso 1 1 calc R . . H4B2 H 0.0763 0.8660 0.0841 0.022 Uiso 1 1 calc R . . C5B C 0.0829(3) 0.8769(5) -0.0162(3) 0.0235(13) Uani 1 1 d . . . C6B C 0.1588(3) 0.8801(5) -0.0127(3) 0.0241(13) Uani 1 1 d . . . H6B1 H 0.1821 0.9406 0.0239 0.029 Uiso 1 1 calc R . . H6B2 H 0.1650 0.9129 -0.0569 0.029 Uiso 1 1 calc R . . C7B C 0.1937(3) 0.7493(5) 0.0018(2) 0.0162(12) Uani 1 1 d . . . C8B C 0.1770(3) 0.6925(5) 0.0663(2) 0.0154(12) Uani 1 1 d . . . H8B1 H 0.1986 0.6068 0.0754 0.018 Uiso 1 1 calc R . . H8B2 H 0.1978 0.7478 0.1063 0.018 Uiso 1 1 calc R . . C9B C 0.1657(3) 0.6603(6) -0.0609(3) 0.0274(14) Uani 1 1 d . . . H9B1 H 0.1795 0.6941 -0.1008 0.041 Uiso 1 1 calc R . . H9B2 H 0.1150 0.6565 -0.0713 0.041 Uiso 1 1 calc R . . H9B3 H 0.1849 0.5740 -0.0502 0.041 Uiso 1 1 calc R . . C10B C 0.2715(3) 0.7629(6) 0.0149(3) 0.0263(14) Uani 1 1 d . . . H10D H 0.2824 0.8056 -0.0244 0.039 Uiso 1 1 calc R . . H10E H 0.2930 0.6778 0.0211 0.039 Uiso 1 1 calc R . . H10F H 0.2895 0.8141 0.0565 0.039 Uiso 1 1 calc R . . C11B C 0.1123(3) 0.4860(5) 0.1425(3) 0.0132(11) Uani 1 1 d . . . C12B C 0.1570(2) 0.4494(5) 0.2038(2) 0.011 Uiso 1 1 d . . . H12B H 0.1771 0.5137 0.2362 0.016 Uiso 1 1 calc R . . C13B C 0.1735(3) 0.3230(5) 0.2197(3) 0.0174(12) Uani 1 1 d . . . H13B H 0.2014 0.2992 0.2638 0.021 Uiso 1 1 calc R . . C14B C 0.1488(3) 0.2336(5) 0.1705(3) 0.0160(12) Uani 1 1 d . . . C15B C 0.1073(3) 0.2646(5) 0.1064(3) 0.0161(12) Uani 1 1 d . . . H15B H 0.0912 0.2005 0.0725 0.019 Uiso 1 1 calc R . . C16B C 0.0900(3) 0.3918(5) 0.0931(2) 0.0167(12) Uani 1 1 d . . . H16B H 0.0621 0.4154 0.0490 0.020 Uiso 1 1 calc R . . C17B C 0.0084(3) 0.6278(5) 0.1204(3) 0.0157(12) Uani 1 1 d . . . C18B C -0.0813(2) 0.7434(5) 0.1606(2) 0.0159(12) Uani 1 1 d . . . C19B C -0.1071(3) 0.6283(5) 0.1921(3) 0.0246(14) Uani 1 1 d . . . H19D H -0.1089 0.5538 0.1621 0.037 Uiso 1 1 calc R . . H19E H -0.1535 0.6460 0.1976 0.037 Uiso 1 1 calc R . . H19F H -0.0755 0.6104 0.2372 0.037 Uiso 1 1 calc R . . C20B C -0.1247(3) 0.7731(5) 0.0886(3) 0.0237(13) Uani 1 1 d . . . H20D H -0.1017 0.8395 0.0681 0.036 Uiso 1 1 calc R . . H20E H -0.1704 0.8038 0.0909 0.036 Uiso 1 1 calc R . . H20F H -0.1301 0.6954 0.0605 0.036 Uiso 1 1 calc R . . C21B C -0.0753(3) 0.8608(5) 0.2058(3) 0.0272(14) Uani 1 1 d . . . H21D H -0.0444 0.8423 0.2511 0.041 Uiso 1 1 calc R . . H21E H -0.1213 0.8839 0.2109 0.041 Uiso 1 1 calc R . . H21F H -0.0565 0.9321 0.1846 0.041 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 Br1A 0.0321(4) 0.0145(3) 0.0251(3) 0.0025(2) 0.0049(3) 0.0053(3) N1A 0.014(3) 0.013(2) 0.021(2) 0.0001(19) 0.004(2) 0.004(2) C1A 0.013(3) 0.019(3) 0.013(3) -0.001(2) 0.006(2) -0.002(2) O1A 0.032(2) 0.033(3) 0.029(2) 0.0000(19) 0.0055(19) 0.016(2) O2A 0.020(2) 0.025(2) 0.0191(19) -0.0040(18) 0.0033(16) -0.0056(19) C2A 0.018(3) 0.011(3) 0.011(3) 0.009(2) 0.008(2) 0.005(2) O3A 0.021(2) 0.022(2) 0.0114(18) 0.0005(15) 0.0079(16) -0.0054(17) C3A 0.011(3) 0.016(3) 0.018(3) -0.002(2) 0.002(2) 0.005(2) C4A 0.018(3) 0.019(3) 0.023(3) 0.000(2) 0.008(3) 0.002(2) C5A 0.019(3) 0.013(3) 0.028(3) -0.005(2) 0.000(3) 0.000(2) C6A 0.024(3) 0.023(3) 0.023(3) -0.007(2) 0.010(3) 0.006(3) C7A 0.016(3) 0.017(3) 0.020(3) -0.003(2) 0.006(2) -0.001(2) C8A 0.015(3) 0.022(3) 0.011(3) -0.001(2) 0.004(2) 0.002(2) C9A 0.019(3) 0.035(4) 0.024(3) 0.000(3) 0.010(3) 0.005(3) C10A 0.021(3) 0.033(4) 0.035(4) -0.009(3) 0.011(3) -0.005(3) C11A 0.015(3) 0.011(3) 0.012(3) 0.002(2) 0.007(2) 0.006(2) C12A 0.012(3) 0.020(3) 0.020(3) 0.004(2) 0.001(2) 0.003(2) C13A 0.018(3) 0.019(3) 0.021(3) -0.003(2) 0.002(3) -0.002(2) C14A 0.021(3) 0.013(3) 0.016(3) 0.004(2) 0.008(2) 0.000(2) C15A 0.018(3) 0.024(3) 0.016(3) 0.005(2) 0.006(2) 0.000(3) C17A 0.013(3) 0.017(3) 0.018(3) 0.008(2) 0.004(2) 0.008(2) C18A 0.017(3) 0.022(3) 0.010(3) 0.006(2) 0.007(2) -0.001(2) C19A 0.023(3) 0.031(3) 0.022(3) 0.003(3) 0.011(3) 0.007(3) C20A 0.027(3) 0.036(4) 0.017(3) 0.006(3) 0.012(3) 0.007(3) C21A 0.034(4) 0.022(3) 0.033(3) 0.003(3) 0.018(3) 0.001(3) Br1B 0.0254(3) 0.0137(3) 0.0299(3) 0.0043(3) 0.0057(3) 0.0035(3) N1B 0.013(2) 0.016(2) 0.018(2) 0.0014(19) 0.005(2) 0.002(2) O1B 0.028(2) 0.036(3) 0.028(2) 0.016(2) 0.0040(19) 0.006(2) C1B 0.014(3) 0.016(3) 0.010(3) -0.002(2) 0.005(2) 0.001(2) O2B 0.016(2) 0.024(2) 0.0174(18) -0.0033(17) 0.0034(16) -0.0019(18) C2B 0.006(3) 0.015(3) 0.017(3) 0.004(2) 0.002(2) 0.006(2) O3B 0.009(2) 0.021(2) 0.0201(19) -0.0040(16) 0.0046(16) 0.0015(16) C3B 0.020(3) 0.012(3) 0.016(3) 0.004(2) 0.005(2) -0.001(2) C4B 0.022(3) 0.019(3) 0.017(3) 0.006(2) 0.007(3) 0.001(2) C5B 0.028(4) 0.012(3) 0.032(3) -0.002(3) 0.011(3) -0.004(3) C6B 0.019(3) 0.025(3) 0.030(3) 0.004(3) 0.010(3) -0.005(3) C7B 0.013(3) 0.021(3) 0.016(3) -0.001(2) 0.006(2) -0.006(2) C8B 0.011(3) 0.019(3) 0.016(3) -0.001(2) 0.004(2) 0.001(2) C9B 0.027(4) 0.031(4) 0.026(3) -0.006(3) 0.011(3) -0.010(3) C10B 0.020(3) 0.032(4) 0.028(3) 0.006(3) 0.007(3) -0.004(3) C11B 0.011(3) 0.013(3) 0.018(3) 0.005(2) 0.008(2) 0.002(2) C13B 0.012(3) 0.022(3) 0.017(3) 0.007(2) 0.000(2) 0.005(2) C14B 0.011(3) 0.017(3) 0.022(3) 0.000(2) 0.009(2) 0.006(2) C15B 0.015(3) 0.015(3) 0.017(3) -0.004(2) 0.003(2) -0.002(2) C16B 0.019(3) 0.018(3) 0.013(3) 0.003(2) 0.003(2) 0.001(2) C17B 0.017(3) 0.015(3) 0.017(3) 0.003(2) 0.008(2) 0.004(2) C18B 0.003(3) 0.029(3) 0.015(3) 0.000(2) 0.002(2) 0.003(2) C19B 0.024(3) 0.026(3) 0.027(3) 0.006(3) 0.012(3) 0.007(3) C20B 0.016(3) 0.026(3) 0.032(3) 0.007(3) 0.013(3) 0.005(3) C21B 0.031(4) 0.023(3) 0.031(3) -0.009(3) 0.013(3) 0.002(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 Br1A C14A 1.909(5) . ? N1A C2A 1.130(6) . ? C1A C2A 1.494(7) . ? C1A C11A 1.522(7) . ? C1A C17A 1.543(7) . ? C1A C3A 1.581(7) . ? O1A C5A 1.222(6) . ? O2A C17A 1.202(6) . ? O3A C17A 1.334(6) . ? O3A C18A 1.503(5) . ? C3A C8A 1.523(7) . ? C3A C4A 1.537(7) . ? C3A H3A 1.0000 . ? C4A C5A 1.500(7) . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C5A C6A 1.513(7) . ? C6A C7A 1.532(7) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C7A C9A 1.513(7) . ? C7A C8A 1.527(7) . ? C7A C10A 1.545(7) . ? C8A H8A1 0.9900 . ? C8A H8A2 0.9900 . ? C9A H9A1 0.9800 . ? C9A H9A2 0.9800 . ? C9A H9A3 0.9800 . ? C10A H10A 0.9800 . ? C10A H10B 0.9800 . ? C10A H10C 0.9800 . ? C11A C16A 1.367(7) . ? C11A C12A 1.389(7) . ? C12A C13A 1.402(7) . ? C12A H12A 0.9500 . ? C13A C14A 1.378(7) . ? C13A H13A 0.9500 . ? C14A C15A 1.359(7) . ? C15A C16A 1.381(7) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C18A C21A 1.499(7) . ? C18A C20A 1.511(7) . ? C18A C19A 1.514(7) . ? C19A H19A 0.9800 . ? C19A H19B 0.9800 . ? C19A H19C 0.9800 . ? C20A H20A 0.9800 . ? C20A H20B 0.9800 . ? C20A H20C 0.9800 . ? C21A H21A 0.9800 . ? C21A H21B 0.9800 . ? C21A H21C 0.9800 . ? Br1B C14B 1.912(5) . ? N1B C2B 1.138(6) . ? O1B C5B 1.223(6) . ? C1B C2B 1.488(7) . ? C1B C11B 1.529(7) . ? C1B C17B 1.539(7) . ? C1B C3B 1.571(7) . ? O2B C17B 1.206(6) . ? O3B C17B 1.330(6) . ? O3B C18B 1.494(6) . ? C3B C8B 1.518(7) . ? C3B C4B 1.539(7) . ? C3B H3B 1.0000 . ? C4B C5B 1.511(7) . ? C4B H4B1 0.9900 . ? C4B H4B2 0.9900 . ? C5B C6B 1.500(8) . ? C6B C7B 1.527(7) . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C7B C10B 1.516(7) . ? C7B C8B 1.541(7) . ? C7B C9B 1.550(7) . ? C8B H8B1 0.9900 . ? C8B H8B2 0.9900 . ? C9B H9B1 0.9800 . ? C9B H9B2 0.9800 . ? C9B H9B3 0.9800 . ? C10B H10D 0.9800 . ? C10B H10E 0.9800 . ? C10B H10F 0.9800 . ? C11B C12B 1.378(6) . ? C11B C16B 1.387(7) . ? C12B C13B 1.378(7) . ? C12B H12B 0.9500 . ? C13B C14B 1.358(7) . ? C13B H13B 0.9500 . ? C14B C15B 1.381(7) . ? C15B C16B 1.380(7) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? C18B C19B 1.509(7) . ? C18B C21B 1.511(7) . ? C18B C20B 1.517(7) . ? C19B H19D 0.9800 . ? C19B H19E 0.9800 . ? C19B H19F 0.9800 . ? C20B H20D 0.9800 . ? C20B H20E 0.9800 . ? C20B H20F 0.9800 . ? C21B H21D 0.9800 . ? C21B H21E 0.9800 . ? C21B H21F 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 C2A C1A C11A 110.4(4) . . ? C2A C1A C17A 110.5(4) . . ? C11A C1A C17A 108.8(4) . . ? C2A C1A C3A 107.0(4) . . ? C11A C1A C3A 112.7(4) . . ? C17A C1A C3A 107.4(4) . . ? N1A C2A C1A 177.4(5) . . ? C17A O3A C18A 121.0(4) . . ? C8A C3A C4A 110.5(4) . . ? C8A C3A C1A 110.8(4) . . ? C4A C3A C1A 110.1(4) . . ? C8A C3A H3A 108.5 . . ? C4A C3A H3A 108.5 . . ? C1A C3A H3A 108.5 . . ? C5A C4A C3A 112.8(4) . . ? C5A C4A H4A1 109.0 . . ? C3A C4A H4A1 109.0 . . ? C5A C4A H4A2 109.0 . . ? C3A C4A H4A2 109.0 . . ? H4A1 C4A H4A2 107.8 . . ? O1A C5A C4A 122.4(5) . . ? O1A C5A C6A 122.1(5) . . ? C4A C5A C6A 115.5(5) . . ? C5A C6A C7A 113.7(4) . . ? C5A C6A H6A1 108.8 . . ? C7A C6A H6A1 108.8 . . ? C5A C6A H6A2 108.8 . . ? C7A C6A H6A2 108.8 . . ? H6A1 C6A H6A2 107.7 . . ? C9A C7A C8A 109.1(4) . . ? C9A C7A C6A 109.7(4) . . ? C8A C7A C6A 108.4(4) . . ? C9A C7A C10A 109.9(4) . . ? C8A C7A C10A 110.4(4) . . ? C6A C7A C10A 109.4(4) . . ? C3A C8A C7A 114.3(4) . . ? C3A C8A H8A1 108.7 . . ? C7A C8A H8A1 108.7 . . ? C3A C8A H8A2 108.7 . . ? C7A C8A H8A2 108.7 . . ? H8A1 C8A H8A2 107.6 . . ? C7A C9A H9A1 109.5 . . ? C7A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C7A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? C7A C10A H10A 109.5 . . ? C7A C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? C7A C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C16A C11A C12A 117.3(5) . . ? C16A C11A C1A 122.6(5) . . ? C12A C11A C1A 120.2(4) . . ? C11A C12A C13A 121.3(5) . . ? C11A C12A H12A 119.4 . . ? C13A C12A H12A 119.4 . . ? C14A C13A C12A 117.5(5) . . ? C14A C13A H13A 121.3 . . ? C12A C13A H13A 121.3 . . ? C15A C14A C13A 122.8(5) . . ? C15A C14A Br1A 119.2(4) . . ? C13A C14A Br1A 117.9(4) . . ? C14A C15A C16A 117.6(5) . . ? C14A C15A H15A 121.2 . . ? C16A C15A H15A 121.2 . . ? C11A C16A C15A 123.0(5) . . ? C11A C16A H16A 118.5 . . ? C15A C16A H16A 118.5 . . ? O2A C17A O3A 127.5(5) . . ? O2A C17A C1A 121.9(5) . . ? O3A C17A C1A 110.7(4) . . ? C21A C18A O3A 101.5(4) . . ? C21A C18A C20A 111.5(5) . . ? O3A C18A C20A 110.3(4) . . ? C21A C18A C19A 112.2(4) . . ? O3A C18A C19A 106.9(4) . . ? C20A C18A C19A 113.6(4) . . ? C18A C19A H19A 109.5 . . ? C18A C19A H19B 109.5 . . ? H19A C19A H19B 109.5 . . ? C18A C19A H19C 109.5 . . ? H19A C19A H19C 109.5 . . ? H19B C19A H19C 109.5 . . ? C18A C20A H20A 109.5 . . ? C18A C20A H20B 109.5 . . ? H20A C20A H20B 109.5 . . ? C18A C20A H20C 109.5 . . ? H20A C20A H20C 109.5 . . ? H20B C20A H20C 109.5 . . ? C18A C21A H21A 109.5 . . ? C18A C21A H21B 109.5 . . ? H21A C21A H21B 109.5 . . ? C18A C21A H21C 109.5 . . ? H21A C21A H21C 109.5 . . ? H21B C21A H21C 109.5 . . ? C2B C1B C11B 109.3(4) . . ? C2B C1B C17B 110.1(4) . . ? C11B C1B C17B 108.7(4) . . ? C2B C1B C3B 108.3(4) . . ? C11B C1B C3B 113.3(4) . . ? C17B C1B C3B 107.1(4) . . ? N1B C2B C1B 175.7(5) . . ? C17B O3B C18B 121.5(4) . . ? C8B C3B C4B 110.5(4) . . ? C8B C3B C1B 110.4(4) . . ? C4B C3B C1B 110.5(4) . . ? C8B C3B H3B 108.5 . . ? C4B C3B H3B 108.5 . . ? C1B C3B H3B 108.5 . . ? C5B C4B C3B 112.4(4) . . ? C5B C4B H4B1 109.1 . . ? C3B C4B H4B1 109.1 . . ? C5B C4B H4B2 109.1 . . ? C3B C4B H4B2 109.1 . . ? H4B1 C4B H4B2 107.9 . . ? O1B C5B C6B 122.7(5) . . ? O1B C5B C4B 121.6(5) . . ? C6B C5B C4B 115.7(5) . . ? C5B C6B C7B 113.2(4) . . ? C5B C6B H6B1 108.9 . . ? C7B C6B H6B1 108.9 . . ? C5B C6B H6B2 108.9 . . ? C7B C6B H6B2 108.9 . . ? H6B1 C6B H6B2 107.7 . . ? C10B C7B C6B 110.3(4) . . ? C10B C7B C8B 109.0(4) . . ? C6B C7B C8B 108.5(4) . . ? C10B C7B C9B 109.6(4) . . ? C6B C7B C9B 109.2(4) . . ? C8B C7B C9B 110.2(4) . . ? C3B C8B C7B 113.5(4) . . ? C3B C8B H8B1 108.9 . . ? C7B C8B H8B1 108.9 . . ? C3B C8B H8B2 108.9 . . ? C7B C8B H8B2 108.9 . . ? H8B1 C8B H8B2 107.7 . . ? C7B C9B H9B1 109.5 . . ? C7B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C7B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? C7B C10B H10D 109.5 . . ? C7B C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? C7B C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? C12B C11B C16B 117.4(5) . . ? C12B C11B C1B 122.4(4) . . ? C16B C11B C1B 120.2(4) . . ? C13B C12B C11B 122.4(5) . . ? C13B C12B H12B 118.8 . . ? C11B C12B H12B 118.8 . . ? C14B C13B C12B 117.9(5) . . ? C14B C13B H13B 121.1 . . ? C12B C13B H13B 121.1 . . ? C13B C14B C15B 122.6(5) . . ? C13B C14B Br1B 118.7(4) . . ? C15B C14B Br1B 118.6(4) . . ? C16B C15B C14B 117.8(5) . . ? C16B C15B H15B 121.1 . . ? C14B C15B H15B 121.1 . . ? C15B C16B C11B 121.6(5) . . ? C15B C16B H16B 119.2 . . ? C11B C16B H16B 119.2 . . ? O2B C17B O3B 126.6(5) . . ? O2B C17B C1B 122.3(4) . . ? O3B C17B C1B 111.0(4) . . ? O3B C18B C19B 107.9(4) . . ? O3B C18B C21B 102.9(4) . . ? C19B C18B C21B 112.0(4) . . ? O3B C18B C20B 110.4(4) . . ? C19B C18B C20B 113.0(4) . . ? C21B C18B C20B 110.2(5) . . ? C18B C19B H19D 109.5 . . ? C18B C19B H19E 109.5 . . ? H19D C19B H19E 109.5 . . ? C18B C19B H19F 109.5 . . ? H19D C19B H19F 109.5 . . ? H19E C19B H19F 109.5 . . ? C18B C20B H20D 109.5 . . ? C18B C20B H20E 109.5 . . ? H20D C20B H20E 109.5 . . ? C18B C20B H20F 109.5 . . ? H20D C20B H20F 109.5 . . ? H20E C20B H20F 109.5 . . ? C18B C21B H21D 109.5 . . ? C18B C21B H21E 109.5 . . ? H21D C21B H21E 109.5 . . ? C18B C21B H21F 109.5 . . ? H21D C21B H21F 109.5 . . ? H21E C21B H21F 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 C11A C1A C2A N1A -44(12) . . . . ? C17A C1A C2A N1A -164(12) . . . . ? C3A C1A C2A N1A 79(12) . . . . ? C2A C1A C3A C8A -55.8(5) . . . . ? C11A C1A C3A C8A 65.7(5) . . . . ? C17A C1A C3A C8A -174.5(4) . . . . ? C2A C1A C3A C4A 66.7(5) . . . . ? C11A C1A C3A C4A -171.8(4) . . . . ? C17A C1A C3A C4A -52.0(5) . . . . ? C8A C3A C4A C5A -49.1(6) . . . . ? C1A C3A C4A C5A -171.8(4) . . . . ? C3A C4A C5A O1A -135.7(5) . . . . ? C3A C4A C5A C6A 46.9(6) . . . . ? O1A C5A C6A C7A 133.8(5) . . . . ? C4A C5A C6A C7A -48.9(6) . . . . ? C5A C6A C7A C9A 170.2(5) . . . . ? C5A C6A C7A C8A 51.2(6) . . . . ? C5A C6A C7A C10A -69.2(6) . . . . ? C4A C3A C8A C7A 56.0(6) . . . . ? C1A C3A C8A C7A 178.3(4) . . . . ? C9A C7A C8A C3A -175.8(4) . . . . ? C6A C7A C8A C3A -56.4(6) . . . . ? C10A C7A C8A C3A 63.4(6) . . . . ? C2A C1A C11A C16A -4.4(6) . . . . ? C17A C1A C11A C16A 117.0(5) . . . . ? C3A C1A C11A C16A -124.0(5) . . . . ? C2A C1A C11A C12A 176.8(4) . . . . ? C17A C1A C11A C12A -61.8(6) . . . . ? C3A C1A C11A C12A 57.2(6) . . . . ? C16A C11A C12A C13A -5.9(7) . . . . ? C1A C11A C12A C13A 173.0(5) . . . . ? C11A C12A C13A C14A -0.3(8) . . . . ? C12A C13A C14A C15A 3.4(8) . . . . ? C12A C13A C14A Br1A -173.9(4) . . . . ? C13A C14A C15A C16A -0.2(8) . . . . ? Br1A C14A C15A C16A 177.1(4) . . . . ? C12A C11A C16A C15A 9.4(7) . . . . ? C1A C11A C16A C15A -169.4(5) . . . . ? C14A C15A C16A C11A -6.5(7) . . . . ? C18A O3A C17A O2A -1.5(8) . . . . ? C18A O3A C17A C1A -180.0(4) . . . . ? C2A C1A C17A O2A 173.4(5) . . . . ? C11A C1A C17A O2A 52.0(6) . . . . ? C3A C1A C17A O2A -70.2(6) . . . . ? C2A C1A C17A O3A -8.1(6) . . . . ? C11A C1A C17A O3A -129.5(4) . . . . ? C3A C1A C17A O3A 108.3(5) . . . . ? C17A O3A C18A C21A 173.7(4) . . . . ? C17A O3A C18A C20A 55.4(6) . . . . ? C17A O3A C18A C19A -68.5(5) . . . . ? C11B C1B C2B N1B 69(7) . . . . ? C17B C1B C2B N1B -172(7) . . . . ? C3B C1B C2B N1B -55(7) . . . . ? C2B C1B C3B C8B 55.4(5) . . . . ? C11B C1B C3B C8B -66.1(5) . . . . ? C17B C1B C3B C8B 174.1(4) . . . . ? C2B C1B C3B C4B -67.2(5) . . . . ? C11B C1B C3B C4B 171.4(4) . . . . ? C17B C1B C3B C4B 51.5(5) . . . . ? C8B C3B C4B C5B 49.1(6) . . . . ? C1B C3B C4B C5B 171.6(4) . . . . ? C3B C4B C5B O1B 134.4(5) . . . . ? C3B C4B C5B C6B -47.1(6) . . . . ? O1B C5B C6B C7B -131.9(5) . . . . ? C4B C5B C6B C7B 49.6(6) . . . . ? C5B C6B C7B C10B -171.8(5) . . . . ? C5B C6B C7B C8B -52.4(6) . . . . ? C5B C6B C7B C9B 67.7(6) . . . . ? C4B C3B C8B C7B -56.3(6) . . . . ? C1B C3B C8B C7B -178.9(4) . . . . ? C10B C7B C8B C3B 177.6(4) . . . . ? C6B C7B C8B C3B 57.4(6) . . . . ? C9B C7B C8B C3B -62.1(6) . . . . ? C2B C1B C11B C12B 5.5(6) . . . . ? C17B C1B C11B C12B -114.7(5) . . . . ? C3B C1B C11B C12B 126.3(5) . . . . ? C2B C1B C11B C16B -174.8(4) . . . . ? C17B C1B C11B C16B 65.0(6) . . . . ? C3B C1B C11B C16B -54.0(6) . . . . ? C16B C11B C12B C13B -7.2(7) . . . . ? C1B C11B C12B C13B 172.5(5) . . . . ? C11B C12B C13B C14B 5.3(7) . . . . ? C12B C13B C14B C15B -1.0(8) . . . . ? C12B C13B C14B Br1B -177.5(4) . . . . ? C13B C14B C15B C16B -1.1(8) . . . . ? Br1B C14B C15B C16B 175.4(4) . . . . ? C14B C15B C16B C11B -1.0(8) . . . . ? C12B C11B C16B C15B 4.9(7) . . . . ? C1B C11B C16B C15B -174.8(5) . . . . ? C18B O3B C17B O2B 1.6(8) . . . . ? C18B O3B C17B C1B 178.6(4) . . . . ? C2B C1B C17B O2B -173.2(5) . . . . ? C11B C1B C17B O2B -53.4(6) . . . . ? C3B C1B C17B O2B 69.3(6) . . . . ? C2B C1B C17B O3B 9.6(6) . . . . ? C11B C1B C17B O3B 129.4(4) . . . . ? C3B C1B C17B O3B -107.9(4) . . . . ? C17B O3B C18B C19B 67.4(5) . . . . ? C17B O3B C18B C21B -174.1(4) . . . . ? C17B O3B C18B C20B -56.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.936 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.106 data_s1844lc2 _database_code_depnum_ccdc_archive 'CCDC 856196' #TrackingRef 's1844lc2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ' tert-Butyl-2-cyano-2-(3-hydroxycyclohexyl)-2-phenylacetate' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H25 N O3' _chemical_formula_sum 'C19 H25 N O3' _chemical_formula_weight 315.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0052(5) _cell_length_b 19.3148(11) _cell_length_c 11.0511(7) _cell_angle_alpha 90.00 _cell_angle_beta 110.477(2) _cell_angle_gamma 90.00 _cell_volume 1800.70(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3003 _cell_measurement_theta_min 4.58 _cell_measurement_theta_max 6652 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.163 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.624 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6657 _exptl_absorpt_correction_T_max 0.7526 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source I\mS _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEXII Duo' _diffrn_measurement_method 'Omega + Phi Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 17943 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.58 _diffrn_reflns_theta_max 66.52 _reflns_number_total 3067 _reflns_number_gt 3003 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II Software Suite, 2008' _computing_cell_refinement 'Bruker APEX II Software Suite, 2008' _computing_data_reduction 'Bruker APEX II Software Suite, 2008' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-plus, XP (Sheldrick, 1991)' _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^)+(0.0341P)^2^+0.9396P] 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 0.00137(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3067 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0889 _refine_ls_wR_factor_gt 0.0877 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.22781(11) 0.66048(5) 0.64485(9) 0.0249(2) Uani 1 1 d . . . H1 H 0.1589 0.6486 0.5744 0.037 Uiso 1 1 calc R . . N1 N 0.02650(13) 0.38163(6) 0.59665(11) 0.0241(3) Uani 1 1 d . . . C1 C 0.25589(14) 0.41815(6) 0.80874(11) 0.0166(3) Uani 1 1 d . . . O2 O 0.53842(10) 0.43265(5) 0.87788(9) 0.0241(2) Uani 1 1 d . . . C2 C 0.12999(14) 0.39637(6) 0.68783(12) 0.0180(3) Uani 1 1 d . . . O3 O 0.41162(10) 0.38186(5) 0.68512(8) 0.0201(2) Uani 1 1 d . . . C3 C 0.22773(14) 0.49626(6) 0.83186(11) 0.0164(3) Uani 1 1 d . . . H3 H 0.3131 0.5109 0.9135 0.020 Uiso 1 1 calc R . . C4 C 0.23946(14) 0.54248(6) 0.72272(12) 0.0178(3) Uani 1 1 d . . . H4A H 0.3454 0.5368 0.7157 0.021 Uiso 1 1 calc R . . H4B H 0.1591 0.5277 0.6399 0.021 Uiso 1 1 calc R . . C5 C 0.21341(15) 0.61860(6) 0.74620(12) 0.0191(3) Uani 1 1 d . . . H5 H 0.2993 0.6328 0.8280 0.023 Uiso 1 1 calc R . . C6 C 0.05590(16) 0.62918(7) 0.76550(13) 0.0236(3) Uani 1 1 d . . . H6A H -0.0320 0.6176 0.6846 0.028 Uiso 1 1 calc R . . H6B H 0.0449 0.6784 0.7860 0.028 Uiso 1 1 calc R . . C7 C 0.04551(16) 0.58350(7) 0.87511(14) 0.0253(3) Uani 1 1 d . . . H7A H 0.1277 0.5979 0.9573 0.030 Uiso 1 1 calc R . . H7B H -0.0594 0.5897 0.8839 0.030 Uiso 1 1 calc R . . C8 C 0.06870(15) 0.50736(7) 0.84977(13) 0.0214(3) Uani 1 1 d . . . H8A H -0.0183 0.4920 0.7712 0.026 Uiso 1 1 calc R . . H8B H 0.0647 0.4791 0.9233 0.026 Uiso 1 1 calc R . . C9 C 0.25269(14) 0.37226(6) 0.92181(12) 0.0177(3) Uani 1 1 d . . . C10 C 0.35810(15) 0.38620(7) 1.04598(13) 0.0228(3) Uani 1 1 d . . . H10 H 0.4294 0.4241 1.0599 0.027 Uiso 1 1 calc R . . C11 C 0.35951(16) 0.34513(7) 1.14938(13) 0.0266(3) Uani 1 1 d . . . H11 H 0.4327 0.3547 1.2334 0.032 Uiso 1 1 calc R . . C12 C 0.25475(16) 0.29029(7) 1.13072(14) 0.0269(3) Uani 1 1 d . . . H12 H 0.2565 0.2620 1.2015 0.032 Uiso 1 1 calc R . . C13 C 0.14764(16) 0.27693(7) 1.00839(14) 0.0260(3) Uani 1 1 d . . . H13 H 0.0741 0.2400 0.9955 0.031 Uiso 1 1 calc R . . C14 C 0.14715(15) 0.31747(7) 0.90412(13) 0.0210(3) Uani 1 1 d . . . H14 H 0.0741 0.3076 0.8202 0.025 Uiso 1 1 calc R . . C15 C 0.42087(14) 0.41159(6) 0.79533(11) 0.0168(3) Uani 1 1 d . . . C16 C 0.55629(15) 0.37202(7) 0.64960(13) 0.0249(3) Uani 1 1 d . . . C17 C 0.48579(18) 0.34396(10) 0.51337(15) 0.0408(4) Uani 1 1 d . . . H17A H 0.5704 0.3367 0.4780 0.061 Uiso 1 1 calc R . . H17B H 0.4087 0.3772 0.4593 0.061 Uiso 1 1 calc R . . H17C H 0.4327 0.2998 0.5147 0.061 Uiso 1 1 calc R . . C18 C 0.63614(18) 0.44126(8) 0.65118(16) 0.0358(4) Uani 1 1 d . . . H18A H 0.6896 0.4561 0.7408 0.054 Uiso 1 1 calc R . . H18B H 0.5563 0.4757 0.6056 0.054 Uiso 1 1 calc R . . H18C H 0.7142 0.4367 0.6083 0.054 Uiso 1 1 calc R . . C19 C 0.66417(18) 0.31972(8) 0.74036(16) 0.0357(4) Uani 1 1 d . . . H19A H 0.7528 0.3090 0.7115 0.053 Uiso 1 1 calc R . . H19B H 0.6044 0.2773 0.7405 0.053 Uiso 1 1 calc R . . H19C H 0.7051 0.3390 0.8279 0.053 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0269(5) 0.0243(5) 0.0213(5) 0.0027(4) 0.0058(4) -0.0045(4) N1 0.0216(6) 0.0260(6) 0.0221(6) -0.0046(5) 0.0043(5) -0.0005(5) C1 0.0151(6) 0.0184(6) 0.0150(6) -0.0019(5) 0.0038(5) -0.0012(5) O2 0.0167(5) 0.0312(5) 0.0224(5) -0.0063(4) 0.0043(4) -0.0023(4) C2 0.0188(6) 0.0166(6) 0.0200(7) -0.0007(5) 0.0085(6) 0.0009(5) O3 0.0176(4) 0.0266(5) 0.0177(4) -0.0030(4) 0.0082(4) -0.0020(4) C3 0.0171(6) 0.0164(6) 0.0150(6) -0.0006(5) 0.0048(5) -0.0007(5) C4 0.0166(6) 0.0210(6) 0.0161(6) -0.0005(5) 0.0059(5) -0.0015(5) C5 0.0202(6) 0.0193(6) 0.0160(6) 0.0018(5) 0.0042(5) -0.0015(5) C6 0.0250(7) 0.0202(6) 0.0261(7) 0.0030(5) 0.0096(6) 0.0041(5) C7 0.0279(7) 0.0241(7) 0.0291(7) 0.0028(6) 0.0167(6) 0.0055(5) C8 0.0215(6) 0.0224(7) 0.0234(6) 0.0030(5) 0.0116(5) 0.0015(5) C9 0.0170(6) 0.0172(6) 0.0197(6) 0.0008(5) 0.0073(5) 0.0028(5) C10 0.0201(6) 0.0249(7) 0.0221(7) 0.0022(5) 0.0057(5) -0.0028(5) C11 0.0237(7) 0.0337(8) 0.0209(7) 0.0056(6) 0.0059(5) 0.0021(6) C12 0.0303(7) 0.0248(7) 0.0294(8) 0.0109(6) 0.0154(6) 0.0060(6) C13 0.0291(7) 0.0175(6) 0.0355(8) 0.0019(6) 0.0165(6) -0.0017(5) C14 0.0210(6) 0.0191(6) 0.0234(7) -0.0029(5) 0.0083(5) -0.0006(5) C15 0.0185(6) 0.0153(6) 0.0163(6) 0.0014(5) 0.0057(5) 0.0009(5) C16 0.0185(6) 0.0358(8) 0.0246(7) -0.0040(6) 0.0125(5) -0.0011(6) C17 0.0295(8) 0.0708(12) 0.0278(8) -0.0153(8) 0.0172(7) -0.0075(8) C18 0.0297(8) 0.0436(9) 0.0406(9) 0.0036(7) 0.0202(7) -0.0062(7) C19 0.0299(8) 0.0379(9) 0.0412(9) -0.0029(7) 0.0149(7) 0.0097(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.4238(15) . ? O1 H1 0.8400 . ? N1 C2 1.1437(17) . ? C1 C2 1.4791(17) . ? C1 C9 1.5404(17) . ? C1 C15 1.5489(17) . ? C1 C3 1.5655(16) . ? O2 C15 1.2010(15) . ? O3 C15 1.3226(15) . ? O3 C16 1.4983(15) . ? C3 C8 1.5279(17) . ? C3 C4 1.5336(17) . ? C3 H3 1.0000 . ? C4 C5 1.5253(17) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5201(18) . ? C5 H5 1.0000 . ? C6 C7 1.5277(18) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5250(18) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.3898(18) . ? C9 C10 1.3947(18) . ? C10 C11 1.3875(19) . ? C10 H10 0.9500 . ? C11 C12 1.385(2) . ? C11 H11 0.9500 . ? C12 C13 1.383(2) . ? C12 H12 0.9500 . ? C13 C14 1.3919(19) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C16 C19 1.513(2) . ? C16 C17 1.515(2) . ? C16 C18 1.516(2) . ? 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 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 C5 O1 H1 109.5 . . ? C2 C1 C9 110.07(10) . . ? C2 C1 C15 110.37(10) . . ? C9 C1 C15 108.74(9) . . ? C2 C1 C3 107.75(10) . . ? C9 C1 C3 111.84(10) . . ? C15 C1 C3 108.06(9) . . ? N1 C2 C1 176.00(13) . . ? C15 O3 C16 121.06(9) . . ? C8 C3 C4 110.23(10) . . ? C8 C3 C1 111.66(10) . . ? C4 C3 C1 111.90(10) . . ? C8 C3 H3 107.6 . . ? C4 C3 H3 107.6 . . ? C1 C3 H3 107.6 . . ? C5 C4 C3 111.74(10) . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? O1 C5 C6 112.35(10) . . ? O1 C5 C4 110.61(10) . . ? C6 C5 C4 111.10(10) . . ? O1 C5 H5 107.5 . . ? C6 C5 H5 107.5 . . ? C4 C5 H5 107.5 . . ? C5 C6 C7 110.65(10) . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C8 C7 C6 111.16(11) . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7B 109.4 . . ? C6 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C7 C8 C3 110.72(10) . . ? C7 C8 H8A 109.5 . . ? C3 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C14 C9 C10 118.81(12) . . ? C14 C9 C1 122.00(11) . . ? C10 C9 C1 119.19(11) . . ? C11 C10 C9 120.46(12) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 120.33(13) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 119.62(12) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.23(12) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C9 C14 C13 120.53(12) . . ? C9 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? O2 C15 O3 126.96(11) . . ? O2 C15 C1 121.31(11) . . ? O3 C15 C1 111.72(10) . . ? O3 C16 C19 109.06(11) . . ? O3 C16 C17 101.85(10) . . ? C19 C16 C17 111.63(13) . . ? O3 C16 C18 109.73(11) . . ? C19 C16 C18 112.92(12) . . ? C17 C16 C18 111.06(13) . . ? 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 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C9 C1 C2 N1 80(2) . . . . ? C15 C1 C2 N1 -160.2(19) . . . . ? C3 C1 C2 N1 -42(2) . . . . ? C2 C1 C3 C8 62.22(13) . . . . ? C9 C1 C3 C8 -58.87(13) . . . . ? C15 C1 C3 C8 -178.52(10) . . . . ? C2 C1 C3 C4 -61.87(12) . . . . ? C9 C1 C3 C4 177.03(10) . . . . ? C15 C1 C3 C4 57.39(12) . . . . ? C8 C3 C4 C5 55.62(13) . . . . ? C1 C3 C4 C5 -179.49(10) . . . . ? C3 C4 C5 O1 178.92(9) . . . . ? C3 C4 C5 C6 -55.59(13) . . . . ? O1 C5 C6 C7 -179.87(10) . . . . ? C4 C5 C6 C7 55.62(14) . . . . ? C5 C6 C7 C8 -56.86(15) . . . . ? C6 C7 C8 C3 57.42(14) . . . . ? C4 C3 C8 C7 -56.23(14) . . . . ? C1 C3 C8 C7 178.74(10) . . . . ? C2 C1 C9 C14 2.31(16) . . . . ? C15 C1 C9 C14 -118.70(12) . . . . ? C3 C1 C9 C14 122.05(12) . . . . ? C2 C1 C9 C10 -177.30(11) . . . . ? C15 C1 C9 C10 61.69(14) . . . . ? C3 C1 C9 C10 -57.56(14) . . . . ? C14 C9 C10 C11 1.32(19) . . . . ? C1 C9 C10 C11 -179.05(12) . . . . ? C9 C10 C11 C12 -0.8(2) . . . . ? C10 C11 C12 C13 -0.5(2) . . . . ? C11 C12 C13 C14 1.3(2) . . . . ? C10 C9 C14 C13 -0.51(18) . . . . ? C1 C9 C14 C13 179.87(11) . . . . ? C12 C13 C14 C9 -0.8(2) . . . . ? C16 O3 C15 O2 -1.04(19) . . . . ? C16 O3 C15 C1 178.18(10) . . . . ? C2 C1 C15 O2 172.98(11) . . . . ? C9 C1 C15 O2 -66.19(14) . . . . ? C3 C1 C15 O2 55.39(15) . . . . ? C2 C1 C15 O3 -6.30(14) . . . . ? C9 C1 C15 O3 114.53(11) . . . . ? C3 C1 C15 O3 -123.88(10) . . . . ? C15 O3 C16 C19 67.64(15) . . . . ? C15 O3 C16 C17 -174.26(12) . . . . ? C15 O3 C16 C18 -56.54(15) . . . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 66.52 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.480 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.035 data_s1845lc2 _database_code_depnum_ccdc_archive 'CCDC 856197' #TrackingRef 's1845lc2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '(S)-tert-Butyl-2-cyano-2-((1R,3S)-3-hydroxycyclohexyl)-2-phenylacetate' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H25 N O3' _chemical_absolute_configuration rd _chemical_formula_sum 'C19 H25 N O3' _chemical_formula_weight 315.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 8.2536(3) _cell_length_b 12.3017(5) _cell_length_c 17.9593(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1823.47(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2907 _cell_measurement_theta_min 4.36 _cell_measurement_theta_max 66.59 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.149 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.616 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6458 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source I\mS _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEXII Duo' _diffrn_measurement_method 'Omega + Phi Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 18241 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.36 _diffrn_reflns_theta_max 66.59 _reflns_number_total 3112 _reflns_number_gt 2907 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII Software Suite, 2008' _computing_cell_refinement 'Bruker APEXII Software Suite, 2008' _computing_data_reduction 'Bruker APEXII Software Suite, 2008' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-plus, XP (Sheldrick, 1991)' _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^)+(0.0333P)^2^+0.2950P] 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 0.11(15) _refine_ls_number_reflns 3112 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0343 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0640 _refine_ls_wR_factor_gt 0.0637 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.19181(10) 0.49466(7) 0.23340(4) 0.02349(19) Uani 1 1 d . . . C1 C 0.21833(14) 0.47599(9) 0.36646(6) 0.0178(2) Uani 1 1 d . . . N1 N 0.44363(13) 0.53395(8) 0.46111(6) 0.0243(2) Uani 1 1 d . . . O2 O 0.44151(10) 0.47344(7) 0.28329(4) 0.0247(2) Uani 1 1 d . . . C2 C 0.34763(14) 0.50777(10) 0.41892(6) 0.0191(2) Uani 1 1 d . . . O3 O -0.24305(11) 0.59193(7) 0.52553(5) 0.0252(2) Uani 1 1 d . . . H3 H -0.351(3) 0.5805(15) 0.5166(9) 0.050(5) Uiso 1 1 d . . . C3 C 0.28200(14) 0.48431(9) 0.28556(6) 0.0188(2) Uani 1 1 d . . . C4 C 0.07120(14) 0.55508(9) 0.37620(6) 0.0179(2) Uani 1 1 d . . . H4 H -0.0081 0.5380 0.3358 0.022 Uiso 1 1 calc R . . C5 C 0.11898(15) 0.67449(10) 0.36745(6) 0.0200(2) Uani 1 1 d . . . H5A H 0.1716 0.6854 0.3185 0.024 Uiso 1 1 calc R . . H5B H 0.1978 0.6944 0.4067 0.024 Uiso 1 1 calc R . . C6 C -0.03055(16) 0.74783(10) 0.37333(7) 0.0239(3) Uani 1 1 d . . . H6A H 0.0032 0.8249 0.3704 0.029 Uiso 1 1 calc R . . H6B H -0.1043 0.7329 0.3311 0.029 Uiso 1 1 calc R . . C7 C -0.11992(15) 0.72823(10) 0.44651(7) 0.0232(3) Uani 1 1 d . . . H7A H -0.0500 0.7506 0.4886 0.028 Uiso 1 1 calc R . . H7B H -0.2192 0.7734 0.4478 0.028 Uiso 1 1 calc R . . C8 C -0.16552(13) 0.60966(10) 0.45537(6) 0.0201(2) Uani 1 1 d . . . H8 H -0.2422 0.5891 0.4146 0.024 Uiso 1 1 calc R . . C9 C -0.01582(14) 0.53724(9) 0.45053(6) 0.0196(2) Uani 1 1 d . . . H9A H -0.0484 0.4601 0.4550 0.024 Uiso 1 1 calc R . . H9B H 0.0587 0.5544 0.4921 0.024 Uiso 1 1 calc R . . C10 C 0.16757(14) 0.35706(10) 0.37980(6) 0.0182(2) Uani 1 1 d . . . C11 C 0.21890(15) 0.29838(10) 0.44130(7) 0.0237(3) Uani 1 1 d . . . H11 H 0.2937 0.3299 0.4752 0.028 Uiso 1 1 calc R . . C12 C 0.16151(16) 0.19364(11) 0.45364(7) 0.0282(3) Uani 1 1 d . . . H12 H 0.1965 0.1543 0.4962 0.034 Uiso 1 1 calc R . . C13 C 0.05362(17) 0.14644(10) 0.40416(7) 0.0276(3) Uani 1 1 d . . . H13 H 0.0145 0.0749 0.4126 0.033 Uiso 1 1 calc R . . C14 C 0.00351(17) 0.20412(11) 0.34259(7) 0.0284(3) Uani 1 1 d . . . H14 H -0.0696 0.1718 0.3083 0.034 Uiso 1 1 calc R . . C15 C 0.05906(16) 0.30907(10) 0.33033(7) 0.0238(3) Uani 1 1 d . . . H15 H 0.0229 0.3484 0.2880 0.029 Uiso 1 1 calc R . . C16 C 0.52813(15) 0.46392(11) 0.21018(7) 0.0278(3) Uani 1 1 d . . . C17 C 0.70270(18) 0.45280(19) 0.23472(9) 0.0513(5) Uani 1 1 d . . . H17A H 0.7348 0.5177 0.2628 0.077 Uiso 1 1 calc R . . H17B H 0.7724 0.4451 0.1909 0.077 Uiso 1 1 calc R . . H17C H 0.7140 0.3884 0.2665 0.077 Uiso 1 1 calc R . . C18 C 0.5047(2) 0.56627(13) 0.16486(8) 0.0387(4) Uani 1 1 d . . . H18A H 0.3909 0.5721 0.1496 0.058 Uiso 1 1 calc R . . H18B H 0.5737 0.5634 0.1205 0.058 Uiso 1 1 calc R . . H18C H 0.5340 0.6297 0.1950 0.058 Uiso 1 1 calc R . . C19 C 0.47008(19) 0.36264(12) 0.17076(8) 0.0351(3) Uani 1 1 d . . . H19A H 0.4772 0.3004 0.2047 0.053 Uiso 1 1 calc R . . H19B H 0.5381 0.3492 0.1270 0.053 Uiso 1 1 calc R . . H19C H 0.3573 0.3726 0.1550 0.053 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0215(4) 0.0295(5) 0.0194(4) 0.0009(4) -0.0006(4) 0.0036(3) C1 0.0161(5) 0.0204(6) 0.0170(5) -0.0016(5) -0.0013(4) 0.0003(5) N1 0.0210(5) 0.0277(5) 0.0243(5) 0.0005(5) -0.0030(5) -0.0006(4) O2 0.0162(4) 0.0389(5) 0.0189(4) -0.0027(4) 0.0018(3) 0.0014(4) C2 0.0173(6) 0.0202(6) 0.0198(5) 0.0007(5) 0.0012(5) 0.0016(4) O3 0.0198(5) 0.0350(5) 0.0209(4) -0.0014(4) 0.0024(4) -0.0012(4) C3 0.0183(6) 0.0171(5) 0.0209(6) -0.0008(5) 0.0009(5) 0.0001(4) C4 0.0145(5) 0.0199(6) 0.0194(5) -0.0007(5) -0.0024(5) 0.0005(4) C5 0.0212(6) 0.0210(6) 0.0177(5) 0.0000(5) 0.0009(5) -0.0016(5) C6 0.0266(7) 0.0217(6) 0.0233(6) 0.0010(5) 0.0009(5) 0.0038(5) C7 0.0241(6) 0.0235(6) 0.0221(6) -0.0016(5) 0.0008(5) 0.0069(5) C8 0.0163(6) 0.0275(6) 0.0163(5) -0.0022(5) -0.0002(4) 0.0000(4) C9 0.0185(5) 0.0198(6) 0.0205(5) -0.0004(5) 0.0016(5) -0.0012(4) C10 0.0167(6) 0.0199(6) 0.0179(5) -0.0020(5) 0.0038(5) 0.0019(4) C11 0.0226(6) 0.0260(6) 0.0226(6) 0.0007(5) -0.0022(5) 0.0019(5) C12 0.0313(7) 0.0247(6) 0.0287(6) 0.0070(6) 0.0005(6) 0.0050(5) C13 0.0323(7) 0.0193(6) 0.0312(7) -0.0003(5) 0.0072(6) -0.0012(5) C14 0.0330(7) 0.0266(7) 0.0256(6) -0.0037(5) -0.0004(6) -0.0060(5) C15 0.0272(6) 0.0237(6) 0.0205(6) 0.0010(5) -0.0014(5) -0.0011(5) C16 0.0207(6) 0.0428(8) 0.0200(6) -0.0025(6) 0.0066(5) 0.0000(5) C17 0.0217(7) 0.0994(15) 0.0328(7) -0.0085(9) 0.0063(6) 0.0049(8) C18 0.0432(9) 0.0394(8) 0.0334(7) 0.0027(6) 0.0149(7) -0.0079(6) C19 0.0383(8) 0.0377(8) 0.0293(7) -0.0059(6) 0.0114(6) 0.0020(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.2031(14) . ? C1 C2 1.4761(16) . ? C1 C10 1.5406(16) . ? C1 C3 1.5485(15) . ? C1 C4 1.5659(15) . ? N1 C2 1.1427(16) . ? O2 C3 1.3240(14) . ? O2 C16 1.4996(14) . ? O3 C8 1.4299(14) . ? O3 H3 0.91(2) . ? C4 C5 1.5291(16) . ? C4 C9 1.5316(16) . ? C4 H4 1.0000 . ? C5 C6 1.5324(17) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.5263(17) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5147(17) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.5258(15) . ? C8 H8 1.0000 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.3858(17) . ? C10 C15 1.3928(17) . ? C11 C12 1.3905(19) . ? C11 H11 0.9500 . ? C12 C13 1.3856(19) . ? C12 H12 0.9500 . ? C13 C14 1.3774(19) . ? C13 H13 0.9500 . ? C14 C15 1.3876(18) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C19 1.511(2) . ? C16 C18 1.512(2) . ? C16 C17 1.5129(19) . ? 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 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 C2 C1 C10 110.42(9) . . ? C2 C1 C3 109.63(9) . . ? C10 C1 C3 107.51(9) . . ? C2 C1 C4 108.95(9) . . ? C10 C1 C4 111.21(9) . . ? C3 C1 C4 109.08(9) . . ? C3 O2 C16 120.59(9) . . ? N1 C2 C1 177.58(12) . . ? C8 O3 H3 107.7(11) . . ? O1 C3 O2 127.01(11) . . ? O1 C3 C1 121.84(10) . . ? O2 C3 C1 111.07(10) . . ? C5 C4 C9 110.38(9) . . ? C5 C4 C1 112.67(10) . . ? C9 C4 C1 111.84(9) . . ? C5 C4 H4 107.2 . . ? C9 C4 H4 107.2 . . ? C1 C4 H4 107.2 . . ? C4 C5 C6 110.53(10) . . ? C4 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? C7 C6 C5 110.83(10) . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C8 C7 C6 111.27(10) . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7B 109.4 . . ? C6 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? O3 C8 C7 110.53(9) . . ? O3 C8 C9 108.88(9) . . ? C7 C8 C9 110.80(9) . . ? O3 C8 H8 108.9 . . ? C7 C8 H8 108.9 . . ? C9 C8 H8 108.9 . . ? C8 C9 C4 110.22(9) . . ? C8 C9 H9A 109.6 . . ? C4 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C4 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C11 C10 C15 118.96(11) . . ? C11 C10 C1 122.37(10) . . ? C15 C10 C1 118.57(10) . . ? C10 C11 C12 120.37(12) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 120.33(12) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 119.47(12) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C15 120.50(12) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C10 120.37(11) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? O2 C16 C19 108.87(11) . . ? O2 C16 C18 110.20(11) . . ? C19 C16 C18 113.19(11) . . ? O2 C16 C17 101.89(10) . . ? C19 C16 C17 111.34(13) . . ? C18 C16 C17 110.75(13) . . ? 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 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C10 C1 C2 N1 -97(3) . . . . ? C3 C1 C2 N1 145(3) . . . . ? C4 C1 C2 N1 26(3) . . . . ? C16 O2 C3 O1 -5.03(18) . . . . ? C16 O2 C3 C1 171.88(10) . . . . ? C2 C1 C3 O1 -157.42(11) . . . . ? C10 C1 C3 O1 82.51(13) . . . . ? C4 C1 C3 O1 -38.19(15) . . . . ? C2 C1 C3 O2 25.49(13) . . . . ? C10 C1 C3 O2 -94.58(11) . . . . ? C4 C1 C3 O2 144.72(10) . . . . ? C2 C1 C4 C5 55.01(13) . . . . ? C10 C1 C4 C5 176.95(9) . . . . ? C3 C1 C4 C5 -64.64(12) . . . . ? C2 C1 C4 C9 -70.02(12) . . . . ? C10 C1 C4 C9 51.92(12) . . . . ? C3 C1 C4 C9 170.33(9) . . . . ? C9 C4 C5 C6 -57.21(12) . . . . ? C1 C4 C5 C6 176.98(9) . . . . ? C4 C5 C6 C7 55.98(13) . . . . ? C5 C6 C7 C8 -55.89(13) . . . . ? C6 C7 C8 O3 177.58(9) . . . . ? C6 C7 C8 C9 56.81(13) . . . . ? O3 C8 C9 C4 -179.45(9) . . . . ? C7 C8 C9 C4 -57.69(12) . . . . ? C5 C4 C9 C8 57.96(12) . . . . ? C1 C4 C9 C8 -175.75(9) . . . . ? C2 C1 C10 C11 10.41(15) . . . . ? C3 C1 C10 C11 129.97(11) . . . . ? C4 C1 C10 C11 -110.68(12) . . . . ? C2 C1 C10 C15 -173.23(10) . . . . ? C3 C1 C10 C15 -53.66(13) . . . . ? C4 C1 C10 C15 65.69(13) . . . . ? C15 C10 C11 C12 -0.62(17) . . . . ? C1 C10 C11 C12 175.73(11) . . . . ? C10 C11 C12 C13 0.65(19) . . . . ? C11 C12 C13 C14 0.0(2) . . . . ? C12 C13 C14 C15 -0.6(2) . . . . ? C13 C14 C15 C10 0.6(2) . . . . ? C11 C10 C15 C14 -0.02(18) . . . . ? C1 C10 C15 C14 -176.51(11) . . . . ? C3 O2 C16 C19 -62.02(15) . . . . ? C3 O2 C16 C18 62.67(15) . . . . ? C3 O2 C16 C17 -179.73(13) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 66.59 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.153 _refine_diff_density_min -0.128 _refine_diff_density_rms 0.030 data_s1900lc _database_code_depnum_ccdc_archive 'CCDC 884921' #TrackingRef 's1900lc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '(S)-5-((1R,3S)-3-Methoxycyclohexyl)-5-phenylimidazolidine-2,4-dione' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H20 N2 O3, 0.33(O)' _chemical_absolute_configuration rd _chemical_formula_sum 'C16 H20 N2 O3.33' _chemical_formula_weight 293.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 9.4884(4) _cell_length_b 7.3139(3) _cell_length_c 12.2804(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.801(2) _cell_angle_gamma 90.00 _cell_volume 820.02(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2514 _cell_measurement_theta_min 3.74 _cell_measurement_theta_max 65.37 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 313 _exptl_absorpt_coefficient_mu 0.685 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6768 _exptl_absorpt_correction_T_max 0.7526 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source I\mS _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEXII Duo' _diffrn_measurement_method 'Omega + Phi Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11301 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 65.37 _reflns_number_total 2559 _reflns_number_gt 2514 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII Software Suite, 2008' _computing_cell_refinement 'Bruker APEXII Software Suite, 2008' _computing_data_reduction 'Bruker APEXII Software Suite, 2008' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-plus, XP (Sheldrick, 1991)' _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^)+(0.0372P)^2^+0.1437P] 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 SHELXL _refine_ls_extinction_coef 0.0047(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.09(18) _refine_ls_number_reflns 2559 _refine_ls_number_parameters 218 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0694 _refine_ls_wR_factor_gt 0.0688 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.103 _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 O1 O 0.01272(11) 0.22727(16) 0.47384(8) 0.0268(2) Uani 1 1 d . . . N1 N -0.08199(14) 0.08099(18) 0.60631(11) 0.0223(3) Uani 1 1 d . . . H1 H -0.060(2) -0.032(3) 0.5903(16) 0.035(5) Uiso 1 1 d . . . C1 C -0.04471(15) 0.2335(2) 0.55299(11) 0.0210(3) Uani 1 1 d . . . N2 N -0.08115(14) 0.38254(18) 0.60126(10) 0.0221(3) Uani 1 1 d . . . H2 H -0.0602(18) 0.489(3) 0.5802(14) 0.027(5) Uiso 1 1 d . . . O2 O -0.17286(11) 0.02911(14) 0.76017(8) 0.0260(2) Uani 1 1 d . . . C2 C -0.14323(15) 0.3414(2) 0.69541(11) 0.0191(3) Uani 1 1 d . . . O3 O 0.34994(11) 0.32150(17) 0.97126(10) 0.0352(3) Uani 1 1 d . . . C3 C -0.13818(15) 0.1316(2) 0.69473(12) 0.0204(3) Uani 1 1 d . . . C4 C -0.04390(14) 0.4160(2) 0.80868(11) 0.0189(3) Uani 1 1 d . A . H4 H -0.0919 0.3847 0.8694 0.023 Uiso 1 1 calc R . . C5 C 0.10819(15) 0.3257(2) 0.84037(12) 0.0239(3) Uani 1 1 d . . . H5A H 0.0970 0.1926 0.8503 0.029 Uiso 1 1 calc R A . H5B H 0.1541 0.3432 0.7777 0.029 Uiso 1 1 calc R . . C6 C 0.20827(15) 0.4050(2) 0.94885(13) 0.0275(4) Uani 1 1 d . A . H6 H 0.1656 0.3775 1.0131 0.033 Uiso 1 1 calc R . . C7 C 0.22279(16) 0.6097(2) 0.93962(13) 0.0306(4) Uani 1 1 d . . . H7A H 0.2676 0.6391 0.8777 0.037 Uiso 1 1 calc R A . H7B H 0.2869 0.6588 1.0112 0.037 Uiso 1 1 calc R . . C8 C 0.07133(17) 0.6966(2) 0.91556(13) 0.0279(4) Uani 1 1 d . A . H8A H 0.0290 0.6709 0.9793 0.034 Uiso 1 1 calc R . . H8B H 0.0804 0.8308 0.9096 0.034 Uiso 1 1 calc R . . C9 C -0.03081(16) 0.6232(2) 0.80623(12) 0.0225(3) Uani 1 1 d . . . H9A H -0.1290 0.6784 0.7947 0.027 Uiso 1 1 calc R A . H9B H 0.0069 0.6592 0.7417 0.027 Uiso 1 1 calc R . . C10 C -0.30050(15) 0.4112(2) 0.67316(11) 0.0213(3) Uani 1 1 d . . . C11 C -0.39017(17) 0.3414(2) 0.73568(13) 0.0296(4) Uani 1 1 d . . . H11 H -0.3537 0.2492 0.7906 0.036 Uiso 1 1 calc R . . C12 C -0.53175(18) 0.4045(3) 0.71885(15) 0.0386(4) Uani 1 1 d . . . H12 H -0.5919 0.3548 0.7619 0.046 Uiso 1 1 calc R . . C13 C -0.58624(18) 0.5385(3) 0.64038(15) 0.0430(5) Uani 1 1 d . . . H13 H -0.6836 0.5817 0.6290 0.052 Uiso 1 1 calc R . . C14 C -0.49763(19) 0.6098(3) 0.57813(15) 0.0439(5) Uani 1 1 d . . . H14 H -0.5340 0.7034 0.5242 0.053 Uiso 1 1 calc R . . C15 C -0.35623(17) 0.5456(2) 0.59396(13) 0.0321(4) Uani 1 1 d . . . H15 H -0.2969 0.5945 0.5500 0.039 Uiso 1 1 calc R . . C16 C 0.3608(3) 0.1529(4) 1.0302(3) 0.0562(8) Uani 0.75 1 d PU A 1 H16A H 0.3104 0.1629 1.0898 0.084 Uiso 0.75 1 calc PR A 1 H16B H 0.4643 0.1235 1.0642 0.084 Uiso 0.75 1 calc PR A 1 H16C H 0.3154 0.0558 0.9772 0.084 Uiso 0.75 1 calc PR A 1 C16A C 0.4335(6) 0.3709(4) 1.0969(3) 0.071(3) Uani 0.25 1 d PRU A 2 H16D H 0.4148 0.4990 1.1117 0.106 Uiso 0.25 1 calc PR A 2 H16E H 0.5389 0.3526 1.1085 0.106 Uiso 0.25 1 calc PR A 2 H16F H 0.3990 0.2919 1.1488 0.106 Uiso 0.25 1 calc PR A 2 O1W O 0.6079(4) 0.5093(5) 1.1036(4) 0.083(3) Uani 0.19 1 d PR A 3 O2W O 0.7495(5) 0.4589(4) 1.3334(3) 0.074(4) Uani 0.14 1 d PR A 4 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 0.0439(6) 0.0185(5) 0.0248(5) 0.0001(4) 0.0209(4) 0.0005(5) N1 0.0327(7) 0.0141(7) 0.0235(6) -0.0004(5) 0.0136(5) 0.0001(5) C1 0.0291(7) 0.0153(7) 0.0196(6) -0.0005(6) 0.0084(5) -0.0008(6) N2 0.0345(7) 0.0147(8) 0.0215(6) 0.0007(5) 0.0153(5) -0.0006(5) O2 0.0367(6) 0.0174(6) 0.0290(5) 0.0043(5) 0.0174(4) -0.0003(4) C2 0.0259(7) 0.0166(8) 0.0172(7) 0.0008(6) 0.0100(6) 0.0001(6) O3 0.0184(5) 0.0422(7) 0.0428(6) 0.0085(6) 0.0048(5) 0.0041(5) C3 0.0221(7) 0.0199(8) 0.0202(7) -0.0010(6) 0.0077(5) -0.0016(6) C4 0.0198(7) 0.0198(8) 0.0182(7) 0.0011(5) 0.0072(5) 0.0020(6) C5 0.0220(7) 0.0240(8) 0.0280(7) 0.0034(6) 0.0108(6) 0.0032(6) C6 0.0186(7) 0.0363(9) 0.0281(8) 0.0046(7) 0.0071(6) 0.0009(6) C7 0.0254(8) 0.0374(10) 0.0283(8) -0.0040(7) 0.0063(6) -0.0072(7) C8 0.0333(8) 0.0254(10) 0.0250(7) -0.0048(6) 0.0077(6) -0.0034(6) C9 0.0265(7) 0.0202(9) 0.0211(7) 0.0000(6) 0.0068(6) 0.0004(6) C10 0.0243(7) 0.0192(8) 0.0187(7) -0.0028(6) 0.0030(5) 0.0007(6) C11 0.0281(8) 0.0332(10) 0.0278(8) 0.0048(7) 0.0081(6) 0.0039(7) C12 0.0261(8) 0.0511(12) 0.0393(9) 0.0043(8) 0.0101(7) 0.0025(8) C13 0.0246(8) 0.0581(13) 0.0420(10) 0.0016(9) 0.0015(7) 0.0117(8) C14 0.0383(10) 0.0478(12) 0.0398(10) 0.0117(9) 0.0009(8) 0.0155(8) C15 0.0329(8) 0.0329(10) 0.0298(8) 0.0062(7) 0.0073(6) 0.0027(7) C16 0.0305(13) 0.0498(16) 0.0850(19) 0.0283(15) 0.0100(12) 0.0090(11) C16A 0.060(4) 0.079(4) 0.069(4) -0.001(3) 0.012(3) 0.017(3) O1W 0.072(6) 0.060(6) 0.094(7) 0.002(5) -0.017(5) -0.010(5) O2W 0.066(7) 0.088(10) 0.061(7) -0.001(6) 0.008(6) -0.017(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2378(16) . ? N1 C3 1.3842(18) . ? N1 C1 1.387(2) . ? N1 H1 0.89(2) . ? C1 N2 1.3305(19) . ? N2 C2 1.4647(17) . ? N2 H2 0.86(2) . ? O2 C3 1.2085(17) . ? C2 C10 1.530(2) . ? C2 C3 1.535(2) . ? C2 C4 1.5514(19) . ? O3 C16 1.419(3) . ? O3 C6 1.4331(18) . ? O3 C16A 1.573(3) . ? C4 C9 1.521(2) . ? C4 C5 1.5377(19) . ? C4 H4 1.0000 . ? C5 C6 1.524(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.511(3) . ? C6 H6 1.0000 . ? C7 C8 1.525(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.524(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C15 1.383(2) . ? C10 C11 1.389(2) . ? C11 C12 1.382(2) . ? C11 H11 0.9500 . ? C12 C13 1.373(3) . ? C12 H12 0.9500 . ? C13 C14 1.383(3) . ? C13 H13 0.9500 . ? C14 C15 1.384(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C16A H16D 0.9800 . ? C16A H16E 0.9800 . ? C16A H16F 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 C3 N1 C1 110.93(13) . . ? C3 N1 H1 125.9(13) . . ? C1 N1 H1 122.6(13) . . ? O1 C1 N2 127.12(14) . . ? O1 C1 N1 124.35(14) . . ? N2 C1 N1 108.53(11) . . ? C1 N2 C2 113.12(12) . . ? C1 N2 H2 119.9(12) . . ? C2 N2 H2 126.7(12) . . ? N2 C2 C10 111.90(11) . . ? N2 C2 C3 100.43(12) . . ? C10 C2 C3 111.27(12) . . ? N2 C2 C4 111.03(11) . . ? C10 C2 C4 111.58(11) . . ? C3 C2 C4 110.13(12) . . ? C16 O3 C6 113.73(14) . . ? C16 O3 C16A 75.65(14) . . ? C6 O3 C16A 106.7(2) . . ? O2 C3 N1 126.04(14) . . ? O2 C3 C2 127.01(13) . . ? N1 C3 C2 106.92(12) . . ? C9 C4 C5 110.90(12) . . ? C9 C4 C2 111.44(12) . . ? C5 C4 C2 112.02(12) . . ? C9 C4 H4 107.4 . . ? C5 C4 H4 107.4 . . ? C2 C4 H4 107.4 . . ? C6 C5 C4 112.10(12) . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5B 109.2 . . ? C4 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? O3 C6 C7 109.67(12) . . ? O3 C6 C5 109.53(13) . . ? C7 C6 C5 111.05(13) . . ? O3 C6 H6 108.8 . . ? C7 C6 H6 108.8 . . ? C5 C6 H6 108.8 . . ? C6 C7 C8 109.10(13) . . ? C6 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? C6 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C9 C8 C7 111.32(13) . . ? C9 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? C9 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C4 C9 C8 111.68(12) . . ? C4 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? C4 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 107.9 . . ? C15 C10 C11 118.40(14) . . ? C15 C10 C2 122.03(13) . . ? C11 C10 C2 119.55(13) . . ? C12 C11 C10 120.75(16) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C13 C12 C11 120.57(16) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.18(15) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C13 C14 C15 120.42(16) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C10 C15 C14 120.68(15) . . ? C10 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? O3 C16A H16D 109.5 . . ? O3 C16A H16E 109.5 . . ? H16D C16A H16E 109.5 . . ? O3 C16A H16F 109.5 . . ? H16D C16A H16F 109.5 . . ? H16E C16A H16F 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 C3 N1 C1 O1 177.34(12) . . . . ? C3 N1 C1 N2 -2.70(15) . . . . ? O1 C1 N2 C2 -178.24(13) . . . . ? N1 C1 N2 C2 1.80(15) . . . . ? C1 N2 C2 C10 -118.44(14) . . . . ? C1 N2 C2 C3 -0.30(15) . . . . ? C1 N2 C2 C4 116.16(14) . . . . ? C1 N1 C3 O2 -175.88(14) . . . . ? C1 N1 C3 C2 2.46(16) . . . . ? N2 C2 C3 O2 177.02(14) . . . . ? C10 C2 C3 O2 -64.39(19) . . . . ? C4 C2 C3 O2 59.88(19) . . . . ? N2 C2 C3 N1 -1.29(15) . . . . ? C10 C2 C3 N1 117.30(12) . . . . ? C4 C2 C3 N1 -118.43(12) . . . . ? N2 C2 C4 C9 62.30(15) . . . . ? C10 C2 C4 C9 -63.28(15) . . . . ? C3 C2 C4 C9 172.63(12) . . . . ? N2 C2 C4 C5 -62.61(15) . . . . ? C10 C2 C4 C5 171.81(12) . . . . ? C3 C2 C4 C5 47.72(16) . . . . ? C9 C4 C5 C6 52.20(16) . . . . ? C2 C4 C5 C6 177.41(12) . . . . ? C16 O3 C6 C7 153.06(18) . . . . ? C16A O3 C6 C7 71.75(19) . . . . ? C16 O3 C6 C5 -84.8(2) . . . . ? C16A O3 C6 C5 -166.13(17) . . . . ? C4 C5 C6 O3 -177.46(12) . . . . ? C4 C5 C6 C7 -56.17(16) . . . . ? O3 C6 C7 C8 179.89(11) . . . . ? C5 C6 C7 C8 58.69(16) . . . . ? C6 C7 C8 C9 -59.15(17) . . . . ? C5 C4 C9 C8 -52.27(15) . . . . ? C2 C4 C9 C8 -177.80(11) . . . . ? C7 C8 C9 C4 56.69(17) . . . . ? N2 C2 C10 C15 -19.8(2) . . . . ? C3 C2 C10 C15 -131.26(15) . . . . ? C4 C2 C10 C15 105.30(16) . . . . ? N2 C2 C10 C11 161.70(14) . . . . ? C3 C2 C10 C11 50.24(18) . . . . ? C4 C2 C10 C11 -73.20(18) . . . . ? C15 C10 C11 C12 0.2(2) . . . . ? C2 C10 C11 C12 178.73(15) . . . . ? C10 C11 C12 C13 -0.4(3) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? C12 C13 C14 C15 0.6(3) . . . . ? C11 C10 C15 C14 0.5(2) . . . . ? C2 C10 C15 C14 -178.05(16) . . . . ? C13 C14 C15 C10 -0.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 65.37 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.175 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.028 data_s1948lc _database_code_depnum_ccdc_archive 'CCDC 916148' #TrackingRef 's1948cam.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'compound (S,R,S)-7' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H27 N O4' _chemical_absolute_configuration ad _chemical_formula_sum 'C19 H27 N O4' _chemical_formula_weight 333.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 10.7474(7) _cell_length_b 7.1883(5) _cell_length_c 12.3435(8) _cell_angle_alpha 90.00 _cell_angle_beta 112.278(2) _cell_angle_gamma 90.00 _cell_volume 882.42(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2897 _cell_measurement_theta_min 3.87 _cell_measurement_theta_max 66.15 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.706 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6480 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source I\mS _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEXII Duo' _diffrn_measurement_method 'Omega + Phi Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10176 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.87 _diffrn_reflns_theta_max 66.15 _reflns_number_total 2903 _reflns_number_gt 2897 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII Software Suite, 2008' _computing_cell_refinement 'Bruker APEXII Software Suite, 2008' _computing_data_reduction 'Bruker APEXII Software Suite, 2008' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-plus, XP (Sheldrick, 1991)' _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^)+(0.0354P)^2^+0.1720P] 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 SHELXL _refine_ls_extinction_coef 0.0063(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(13) _refine_ls_number_reflns 2903 _refine_ls_number_parameters 233 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0251 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0664 _refine_ls_wR_factor_gt 0.0662 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.43540(10) -0.60394(14) 0.10026(9) 0.0275(2) Uani 1 1 d D . . H1 H 0.517(2) -0.664(4) 0.115(2) 0.093(9) Uiso 1 1 d D . . N1 N 0.87050(12) 0.2041(2) 0.37195(11) 0.0289(3) Uani 1 1 d . . . H1A H 0.9080(16) 0.146(3) 0.4411(15) 0.023(4) Uiso 1 1 d . . . H1B H 0.897(2) 0.320(4) 0.3583(18) 0.050(6) Uiso 1 1 d . . . C1 C 0.72480(12) -0.06998(18) 0.31363(10) 0.0178(3) Uani 1 1 d . . . O2 O 0.69635(9) 0.21626(14) 0.19923(8) 0.0234(2) Uani 1 1 d . . . C2 C 0.76007(13) 0.13142(19) 0.28912(11) 0.0199(3) Uani 1 1 d . . . O3 O 0.92518(9) -0.26721(17) 0.39469(8) 0.0316(3) Uani 1 1 d . . . C3 C 0.84603(12) -0.18459(19) 0.31219(11) 0.0193(3) Uani 1 1 d . . . O4 O 0.85137(8) -0.17308(13) 0.20702(7) 0.0188(2) Uani 1 1 d . . . C4 C 0.59496(12) -0.13622(18) 0.21060(11) 0.0165(3) Uani 1 1 d . . . H4 H 0.6055 -0.1019 0.1361 0.020 Uiso 1 1 calc R . . C5 C 0.57565(12) -0.34768(19) 0.20909(11) 0.0172(3) Uani 1 1 d . . . H5A H 0.6588 -0.4103 0.2118 0.021 Uiso 1 1 calc R . . H5B H 0.5583 -0.3859 0.2791 0.021 Uiso 1 1 calc R . . C6 C 0.45837(13) -0.40737(18) 0.09915(11) 0.0195(3) Uani 1 1 d . . . H6 H 0.4803 -0.3770 0.0293 0.023 Uiso 1 1 calc R . . C7 C 0.32877(13) -0.30879(19) 0.08699(12) 0.0211(3) Uani 1 1 d . . . H7A H 0.2983 -0.3536 0.1487 0.025 Uiso 1 1 calc R . . H7B H 0.2582 -0.3398 0.0101 0.025 Uiso 1 1 calc R . . C8 C 0.34738(12) -0.0981(2) 0.09713(11) 0.0209(3) Uani 1 1 d . . . H8A H 0.2641 -0.0397 0.0975 0.025 Uiso 1 1 calc R . . H8B H 0.3632 -0.0508 0.0281 0.025 Uiso 1 1 calc R . . C9 C 0.46545(13) -0.04312(18) 0.20851(11) 0.0187(3) Uani 1 1 d . . . H9A H 0.4473 -0.0823 0.2780 0.022 Uiso 1 1 calc R . . H9B H 0.4765 0.0937 0.2114 0.022 Uiso 1 1 calc R . . C10 C 0.70688(12) -0.08185(19) 0.43116(11) 0.0184(3) Uani 1 1 d . . . C11 C 0.65805(13) 0.0718(2) 0.47165(12) 0.0218(3) Uani 1 1 d . . . H11 H 0.6457 0.1864 0.4306 0.026 Uiso 1 1 calc R . . C12 C 0.62710(13) 0.0601(2) 0.57104(11) 0.0240(3) Uani 1 1 d . . . H12 H 0.5944 0.1667 0.5974 0.029 Uiso 1 1 calc R . . C13 C 0.64354(13) -0.1053(2) 0.63173(11) 0.0242(3) Uani 1 1 d . . . H13 H 0.6226 -0.1131 0.6998 0.029 Uiso 1 1 calc R . . C14 C 0.69084(13) -0.2597(2) 0.59224(11) 0.0231(3) Uani 1 1 d . . . H14 H 0.7020 -0.3742 0.6334 0.028 Uiso 1 1 calc R . . C15 C 0.72223(12) -0.2490(2) 0.49283(11) 0.0203(3) Uani 1 1 d . . . H15 H 0.7544 -0.3562 0.4667 0.024 Uiso 1 1 calc R . . C16 C 0.96907(12) -0.2451(2) 0.18409(11) 0.0202(3) Uani 1 1 d . . . C17 C 1.09251(13) -0.1365(2) 0.25965(12) 0.0268(3) Uani 1 1 d . . . H17A H 1.0741 -0.0029 0.2481 0.040 Uiso 1 1 calc R . . H17B H 1.1683 -0.1685 0.2375 0.040 Uiso 1 1 calc R . . H17C H 1.1149 -0.1678 0.3422 0.040 Uiso 1 1 calc R . . C18 C 0.98405(14) -0.4539(2) 0.20432(13) 0.0266(3) Uani 1 1 d . . . H18A H 1.0199 -0.4793 0.2886 0.040 Uiso 1 1 calc R . . H18B H 1.0459 -0.5032 0.1700 0.040 Uiso 1 1 calc R . . H18C H 0.8960 -0.5137 0.1674 0.040 Uiso 1 1 calc R . . C19 C 0.93097(14) -0.1984(2) 0.05547(12) 0.0256(3) Uani 1 1 d . . . H19A H 0.8451 -0.2579 0.0093 0.038 Uiso 1 1 calc R . . H19B H 1.0009 -0.2441 0.0294 0.038 Uiso 1 1 calc R . . H19C H 0.9223 -0.0633 0.0448 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0298(5) 0.0217(5) 0.0299(5) -0.0010(4) 0.0102(4) -0.0026(4) N1 0.0266(6) 0.0343(7) 0.0227(7) 0.0010(6) 0.0056(5) -0.0109(6) C1 0.0145(6) 0.0226(7) 0.0165(6) 0.0005(5) 0.0061(5) 0.0009(5) O2 0.0241(4) 0.0246(5) 0.0210(5) 0.0016(4) 0.0077(4) -0.0025(4) C2 0.0181(6) 0.0252(7) 0.0184(6) -0.0020(5) 0.0094(5) -0.0017(5) O3 0.0198(5) 0.0538(7) 0.0216(5) 0.0112(5) 0.0084(4) 0.0129(5) C3 0.0141(6) 0.0259(7) 0.0178(6) 0.0003(5) 0.0058(5) -0.0010(5) O4 0.0143(4) 0.0264(5) 0.0174(4) 0.0009(4) 0.0080(3) 0.0026(4) C4 0.0143(6) 0.0192(7) 0.0156(6) -0.0004(5) 0.0051(5) -0.0008(5) C5 0.0166(6) 0.0181(6) 0.0180(6) 0.0008(5) 0.0078(5) 0.0023(5) C6 0.0220(6) 0.0197(7) 0.0182(6) 0.0009(5) 0.0091(5) -0.0023(5) C7 0.0164(6) 0.0252(7) 0.0205(6) 0.0014(5) 0.0058(5) -0.0030(5) C8 0.0153(6) 0.0238(7) 0.0239(6) 0.0045(6) 0.0076(5) 0.0017(5) C9 0.0164(6) 0.0180(7) 0.0233(6) 0.0023(5) 0.0092(5) 0.0021(5) C10 0.0124(6) 0.0261(7) 0.0160(6) -0.0010(5) 0.0044(5) -0.0008(5) C11 0.0213(6) 0.0219(7) 0.0212(6) -0.0009(6) 0.0068(5) -0.0011(5) C12 0.0211(6) 0.0300(8) 0.0224(7) -0.0070(6) 0.0100(5) -0.0015(6) C13 0.0193(6) 0.0364(8) 0.0180(6) -0.0026(6) 0.0083(5) -0.0031(6) C14 0.0182(6) 0.0304(7) 0.0197(6) 0.0033(6) 0.0059(5) -0.0007(6) C15 0.0170(6) 0.0248(7) 0.0190(6) -0.0009(6) 0.0067(5) 0.0024(5) C16 0.0164(6) 0.0246(7) 0.0236(7) 0.0004(6) 0.0120(5) 0.0024(6) C17 0.0175(6) 0.0328(8) 0.0322(7) -0.0017(6) 0.0119(6) -0.0019(6) C18 0.0248(7) 0.0257(8) 0.0322(8) 0.0029(6) 0.0142(6) 0.0038(6) C19 0.0256(7) 0.0307(8) 0.0258(7) 0.0021(6) 0.0156(6) 0.0038(6) _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 C6 1.4354(17) . ? O1 H1 0.936(18) . ? N1 C2 1.3443(18) . ? N1 H1A 0.898(18) . ? N1 H1B 0.92(2) . ? C1 C10 1.5364(16) . ? C1 C3 1.5474(18) . ? C1 C2 1.5551(19) . ? C1 C4 1.5639(16) . ? O2 C2 1.2231(16) . ? O3 C3 1.2068(17) . ? C3 O4 1.3236(16) . ? O4 C16 1.4899(14) . ? C4 C5 1.5332(18) . ? C4 C9 1.5358(17) . ? C4 H4 1.0000 . ? C5 C6 1.5224(18) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.5186(18) . ? C6 H6 1.0000 . ? C7 C8 1.527(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.5277(18) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.3943(19) . ? C10 C15 1.398(2) . ? C11 C12 1.3899(19) . ? C11 H11 0.9500 . ? C12 C13 1.381(2) . ? C12 H12 0.9500 . ? C13 C14 1.384(2) . ? C13 H13 0.9500 . ? C14 C15 1.3926(18) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.5171(19) . ? C16 C19 1.5191(18) . ? C16 C18 1.520(2) . ? 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 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 C6 O1 H1 108(2) . . ? C2 N1 H1A 119.3(11) . . ? C2 N1 H1B 117.5(13) . . ? H1A N1 H1B 122.7(17) . . ? C10 C1 C3 112.88(10) . . ? C10 C1 C2 111.26(11) . . ? C3 C1 C2 103.00(9) . . ? C10 C1 C4 110.99(10) . . ? C3 C1 C4 108.92(10) . . ? C2 C1 C4 109.48(10) . . ? O2 C2 N1 121.69(13) . . ? O2 C2 C1 123.15(11) . . ? N1 C2 C1 115.09(12) . . ? O3 C3 O4 125.42(12) . . ? O3 C3 C1 125.42(11) . . ? O4 C3 C1 109.13(10) . . ? C3 O4 C16 121.35(9) . . ? C5 C4 C9 108.31(10) . . ? C5 C4 C1 112.75(10) . . ? C9 C4 C1 113.87(10) . . ? C5 C4 H4 107.2 . . ? C9 C4 H4 107.2 . . ? C1 C4 H4 107.2 . . ? C6 C5 C4 110.66(10) . . ? C6 C5 H5A 109.5 . . ? C4 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? O1 C6 C7 107.80(10) . . ? O1 C6 C5 110.87(10) . . ? C7 C6 C5 112.02(10) . . ? O1 C6 H6 108.7 . . ? C7 C6 H6 108.7 . . ? C5 C6 H6 108.7 . . ? C6 C7 C8 111.60(11) . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C7 C8 C9 111.64(11) . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? C8 C9 C4 109.92(10) . . ? C8 C9 H9A 109.7 . . ? C4 C9 H9A 109.7 . . ? C8 C9 H9B 109.7 . . ? C4 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C11 C10 C15 117.93(11) . . ? C11 C10 C1 119.56(12) . . ? C15 C10 C1 122.05(11) . . ? C12 C11 C10 121.14(13) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C13 C12 C11 120.44(13) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 119.22(12) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C13 C14 C15 120.66(14) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C10 120.61(13) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? O4 C16 C17 108.17(10) . . ? O4 C16 C19 102.12(10) . . ? C17 C16 C19 110.81(11) . . ? O4 C16 C18 110.88(10) . . ? C17 C16 C18 113.19(12) . . ? C19 C16 C18 111.07(12) . . ? 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 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C10 C1 C2 O2 -125.98(13) . . . . ? C3 C1 C2 O2 112.82(13) . . . . ? C4 C1 C2 O2 -2.94(16) . . . . ? C10 C1 C2 N1 56.99(14) . . . . ? C3 C1 C2 N1 -64.20(13) . . . . ? C4 C1 C2 N1 -179.96(11) . . . . ? C10 C1 C3 O3 -4.25(19) . . . . ? C2 C1 C3 O3 115.84(15) . . . . ? C4 C1 C3 O3 -128.00(14) . . . . ? C10 C1 C3 O4 177.57(10) . . . . ? C2 C1 C3 O4 -62.34(12) . . . . ? C4 C1 C3 O4 53.81(13) . . . . ? O3 C3 O4 C16 -7.6(2) . . . . ? C1 C3 O4 C16 170.57(10) . . . . ? C10 C1 C4 C5 -73.33(13) . . . . ? C3 C1 C4 C5 51.54(13) . . . . ? C2 C1 C4 C5 163.46(10) . . . . ? C10 C1 C4 C9 50.59(14) . . . . ? C3 C1 C4 C9 175.46(11) . . . . ? C2 C1 C4 C9 -72.61(13) . . . . ? C9 C4 C5 C6 60.18(13) . . . . ? C1 C4 C5 C6 -172.89(9) . . . . ? C4 C5 C6 O1 -176.96(10) . . . . ? C4 C5 C6 C7 -56.50(14) . . . . ? O1 C6 C7 C8 174.36(10) . . . . ? C5 C6 C7 C8 52.12(14) . . . . ? C6 C7 C8 C9 -52.87(14) . . . . ? C7 C8 C9 C4 57.71(14) . . . . ? C5 C4 C9 C8 -60.69(13) . . . . ? C1 C4 C9 C8 173.02(10) . . . . ? C3 C1 C10 C11 146.35(12) . . . . ? C2 C1 C10 C11 31.13(15) . . . . ? C4 C1 C10 C11 -91.05(14) . . . . ? C3 C1 C10 C15 -41.64(16) . . . . ? C2 C1 C10 C15 -156.86(11) . . . . ? C4 C1 C10 C15 80.96(14) . . . . ? C15 C10 C11 C12 0.78(19) . . . . ? C1 C10 C11 C12 173.12(11) . . . . ? C10 C11 C12 C13 -0.35(19) . . . . ? C11 C12 C13 C14 -0.2(2) . . . . ? C12 C13 C14 C15 0.28(19) . . . . ? C13 C14 C15 C10 0.17(19) . . . . ? C11 C10 C15 C14 -0.69(18) . . . . ? C1 C10 C15 C14 -172.83(11) . . . . ? C3 O4 C16 C17 -62.07(15) . . . . ? C3 O4 C16 C19 -179.00(11) . . . . ? C3 O4 C16 C18 62.61(15) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 66.15 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.368 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.030