data_erk4533 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H23 N' _chemical_formula_weight 253.37 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' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.5993(2) _cell_length_b 17.2910(5) _cell_length_c 10.7919(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.022(2) _cell_angle_gamma 90.00 _cell_volume 1580.17(7) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 1858 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description 'block' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.065 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.457 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.8750 _exptl_absorpt_correction_T_max 0.9346 _exptl_absorpt_process_details 'Denzo (otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11264 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 5.22 _diffrn_reflns_theta_max 67.15 _reflns_number_total 2747 _reflns_number_gt 2423 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Isopropyl group C16-C18 refined with split positions using PART command. ; _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^)+(0.0555P)^2^+0.3159P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'at N1 from difmap, others geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2747 _refine_ls_number_parameters 200 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1233 _refine_ls_wR_factor_gt 0.1175 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.135 _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 N1 N 0.23023(15) 0.72025(8) 0.55110(13) 0.0529(3) Uani 1 1 d . . . H1 H 0.212(2) 0.7529(11) 0.6098(17) 0.063 Uiso 1 1 d . . . C1 C 0.12776(17) 0.67675(8) 0.33609(14) 0.0501(4) Uani 1 1 d . . . C2 C 0.23296(18) 0.61867(9) 0.30313(15) 0.0544(4) Uani 1 1 d . . . H2 H 0.3276 0.6022 0.3534 0.065 Uiso 1 1 calc R . . C3 C 0.1719(2) 0.59171(10) 0.18679(16) 0.0604(4) Uani 1 1 d . . . H3 H 0.2175 0.5532 0.1432 0.073 Uiso 1 1 calc R . . C4 C 0.0272(2) 0.63123(10) 0.14095(16) 0.0623(4) Uani 1 1 d . . . H4 H -0.0382 0.6229 0.0628 0.075 Uiso 1 1 calc R . . C5 C 0.00065(19) 0.68273(9) 0.22934(16) 0.0587(4) Uani 1 1 d . . . H5 H -0.0858 0.7167 0.2226 0.070 Uiso 1 1 calc R . . C6 C 0.12902(17) 0.71975(9) 0.44267(15) 0.0518(4) Uani 1 1 d . . . H6 H 0.0445 0.7547 0.4387 0.062 Uiso 1 1 calc R . . C7 C 0.36737(17) 0.67167(8) 0.58207(14) 0.0488(4) Uani 1 1 d . A . C8 C 0.50961(17) 0.69652(8) 0.54849(13) 0.0497(4) Uani 1 1 d . . . C9 C 0.64017(19) 0.64872(10) 0.58065(15) 0.0585(4) Uani 1 1 d . . . H9 H 0.7374 0.6636 0.5595 0.070 Uiso 1 1 calc R . . C10 C 0.6300(2) 0.57995(10) 0.64286(18) 0.0684(5) Uani 1 1 d . . . H10 H 0.7204 0.5489 0.6649 0.082 Uiso 1 1 calc R . . C11 C 0.4895(2) 0.55645(10) 0.67282(19) 0.0711(5) Uani 1 1 d . A . H11 H 0.4846 0.5091 0.7147 0.085 Uiso 1 1 calc R . . C12 C 0.3533(2) 0.60109(9) 0.64269(16) 0.0605(4) Uani 1 1 d . . . C13 C 0.52005(19) 0.77207(9) 0.47929(15) 0.0576(4) Uani 1 1 d . . . H13 H 0.4179 0.7799 0.4224 0.069 Uiso 1 1 calc R . . C14 C 0.5451(2) 0.84031(10) 0.56956(19) 0.0713(5) Uani 1 1 d . . . H14A H 0.4609 0.8416 0.6189 0.107 Uiso 1 1 calc R . . H14B H 0.5443 0.8880 0.5221 0.107 Uiso 1 1 calc R . . H14C H 0.6459 0.8349 0.6253 0.107 Uiso 1 1 calc R . . C15 C 0.6491(3) 0.77132(14) 0.3986(2) 0.0876(6) Uani 1 1 d . . . H15A H 0.7518 0.7702 0.4526 0.131 Uiso 1 1 calc R . . H15B H 0.6405 0.8174 0.3466 0.131 Uiso 1 1 calc R . . H15C H 0.6371 0.7258 0.3451 0.131 Uiso 1 1 calc R . . C16A C 0.1973(2) 0.57221(11) 0.6727(2) 0.0764(5) Uani 0.577(19) 1 d PD A 1 H16A H 0.1127 0.5977 0.6126 0.092 Uiso 0.577(19) 1 calc PR A 1 C17A C 0.1697(13) 0.5920(7) 0.8008(8) 0.120(3) Uani 0.577(19) 1 d PDU A 1 H17A H 0.0654 0.5745 0.8108 0.179 Uiso 0.577(19) 1 calc PR A 1 H17B H 0.1770 0.6476 0.8125 0.179 Uiso 0.577(19) 1 calc PR A 1 H17C H 0.2487 0.5668 0.8628 0.179 Uiso 0.577(19) 1 calc PR A 1 C18A C 0.1829(11) 0.4849(3) 0.6465(8) 0.0808(19) Uani 0.577(19) 1 d PDU A 1 H18A H 0.2622 0.4576 0.7053 0.121 Uiso 0.577(19) 1 calc PR A 1 H18B H 0.1986 0.4747 0.5612 0.121 Uiso 0.577(19) 1 calc PR A 1 H18C H 0.0786 0.4674 0.6565 0.121 Uiso 0.577(19) 1 calc PR A 1 C16B C 0.1973(2) 0.57221(11) 0.6727(2) 0.0764(5) Uani 0.423(19) 1 d PD A 2 H16B H 0.1192 0.6135 0.6451 0.092 Uiso 0.423(19) 1 calc PR A 2 C17B C 0.2106(14) 0.5662(7) 0.8185(6) 0.084(3) Uani 0.423(19) 1 d PDU A 2 H17D H 0.2436 0.6157 0.8566 0.126 Uiso 0.423(19) 1 calc PR A 2 H17E H 0.2878 0.5270 0.8508 0.126 Uiso 0.423(19) 1 calc PR A 2 H17F H 0.1087 0.5522 0.8388 0.126 Uiso 0.423(19) 1 calc PR A 2 C18B C 0.1286(18) 0.4998(7) 0.6119(13) 0.117(4) Uani 0.423(19) 1 d PDU A 2 H18D H 0.2036 0.4578 0.6321 0.176 Uiso 0.423(19) 1 calc PR A 2 H18E H 0.1054 0.5070 0.5214 0.176 Uiso 0.423(19) 1 calc PR A 2 H18F H 0.0321 0.4874 0.6426 0.176 Uiso 0.423(19) 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 N1 0.0500(7) 0.0481(7) 0.0622(8) -0.0040(6) 0.0144(6) 0.0059(5) C1 0.0446(8) 0.0443(8) 0.0625(9) 0.0060(6) 0.0127(7) -0.0030(6) C2 0.0522(8) 0.0493(8) 0.0624(9) 0.0023(7) 0.0116(7) 0.0014(7) C3 0.0675(10) 0.0533(9) 0.0629(10) 0.0001(7) 0.0178(8) -0.0039(8) C4 0.0637(10) 0.0609(10) 0.0600(9) 0.0084(8) 0.0047(8) -0.0123(8) C5 0.0494(9) 0.0549(9) 0.0708(10) 0.0099(8) 0.0079(7) -0.0022(7) C6 0.0410(8) 0.0464(8) 0.0695(10) 0.0049(7) 0.0142(7) 0.0028(6) C7 0.0498(8) 0.0433(8) 0.0533(8) -0.0028(6) 0.0093(6) 0.0038(6) C8 0.0506(8) 0.0497(8) 0.0486(8) -0.0016(6) 0.0084(6) 0.0029(6) C9 0.0504(9) 0.0636(10) 0.0622(9) -0.0036(8) 0.0113(7) 0.0075(7) C10 0.0678(11) 0.0546(10) 0.0812(12) 0.0003(8) 0.0086(9) 0.0192(8) C11 0.0799(12) 0.0455(9) 0.0870(12) 0.0103(8) 0.0125(10) 0.0085(8) C12 0.0654(10) 0.0464(8) 0.0704(10) 0.0023(7) 0.0141(8) -0.0013(7) C13 0.0507(9) 0.0625(10) 0.0581(9) 0.0116(7) 0.0049(7) -0.0023(7) C14 0.0732(11) 0.0523(10) 0.0897(13) 0.0096(9) 0.0180(10) 0.0005(8) C15 0.0942(15) 0.1040(16) 0.0707(12) 0.0143(11) 0.0310(11) -0.0072(12) C16A 0.0740(12) 0.0627(11) 0.0954(14) 0.0119(10) 0.0231(10) -0.0103(9) C17A 0.099(5) 0.117(6) 0.158(5) -0.076(4) 0.065(4) -0.022(4) C18A 0.091(4) 0.065(3) 0.093(4) -0.019(2) 0.035(3) -0.032(2) C16B 0.0740(12) 0.0627(11) 0.0954(14) 0.0119(10) 0.0231(10) -0.0103(9) C17B 0.083(5) 0.079(5) 0.104(5) -0.038(3) 0.056(3) -0.026(4) C18B 0.094(6) 0.167(8) 0.092(6) -0.027(5) 0.017(4) -0.055(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 N1 C6 1.331(2) . ? N1 C7 1.4391(19) . ? C1 C6 1.368(2) . ? C1 C2 1.437(2) . ? C1 C5 1.447(2) . ? C2 C3 1.356(2) . ? C3 C4 1.431(2) . ? C4 C5 1.353(2) . ? C7 C12 1.400(2) . ? C7 C8 1.402(2) . ? C8 C9 1.389(2) . ? C8 C13 1.515(2) . ? C9 C10 1.376(2) . ? C10 C11 1.366(3) . ? C11 C12 1.393(2) . ? C12 C16A 1.518(2) . ? C13 C14 1.521(3) . ? C13 C15 1.526(3) . ? C16A C17A 1.483(6) . ? C16A C18A 1.537(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C7 125.75(13) . . ? C6 C1 C2 132.43(15) . . ? C6 C1 C5 121.66(14) . . ? C2 C1 C5 105.88(14) . . ? C3 C2 C1 108.09(15) . . ? C2 C3 C4 109.21(15) . . ? C5 C4 C3 108.30(15) . . ? C4 C5 C1 108.51(15) . . ? N1 C6 C1 130.61(14) . . ? C12 C7 C8 122.57(14) . . ? C12 C7 N1 118.90(13) . . ? C8 C7 N1 118.53(13) . . ? C9 C8 C7 117.18(14) . . ? C9 C8 C13 121.44(14) . . ? C7 C8 C13 121.38(13) . . ? C10 C9 C8 121.27(15) . . ? C11 C10 C9 120.44(16) . . ? C10 C11 C12 121.50(16) . . ? C11 C12 C7 117.02(15) . . ? C11 C12 C16A 120.41(16) . . ? C7 C12 C16A 122.56(15) . . ? C8 C13 C14 111.53(13) . . ? C8 C13 C15 112.68(15) . . ? C14 C13 C15 109.66(15) . . ? C17A C16A C12 114.4(4) . . ? C17A C16A C18A 112.1(5) . . ? C12 C16A C18A 109.3(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 177.10(16) . . . . ? C5 C1 C2 C3 -0.72(17) . . . . ? C1 C2 C3 C4 0.23(18) . . . . ? C2 C3 C4 C5 0.38(18) . . . . ? C3 C4 C5 C1 -0.83(18) . . . . ? C6 C1 C5 C4 -177.15(14) . . . . ? C2 C1 C5 C4 0.96(17) . . . . ? C7 N1 C6 C1 -1.1(3) . . . . ? C2 C1 C6 N1 -0.6(3) . . . . ? C5 C1 C6 N1 176.93(15) . . . . ? C6 N1 C7 C12 -92.11(19) . . . . ? C6 N1 C7 C8 86.94(19) . . . . ? C12 C7 C8 C9 -1.5(2) . . . . ? N1 C7 C8 C9 179.43(13) . . . . ? C12 C7 C8 C13 178.06(14) . . . . ? N1 C7 C8 C13 -1.0(2) . . . . ? C7 C8 C9 C10 0.0(2) . . . . ? C13 C8 C9 C10 -179.63(15) . . . . ? C8 C9 C10 C11 1.0(3) . . . . ? C9 C10 C11 C12 -0.5(3) . . . . ? C10 C11 C12 C7 -1.0(3) . . . . ? C10 C11 C12 C16A 177.69(18) . . . . ? C8 C7 C12 C11 2.0(2) . . . . ? N1 C7 C12 C11 -178.96(15) . . . . ? C8 C7 C12 C16A -176.60(16) . . . . ? N1 C7 C12 C16A 2.4(2) . . . . ? C9 C8 C13 C14 -96.66(18) . . . . ? C7 C8 C13 C14 83.74(18) . . . . ? C9 C8 C13 C15 27.2(2) . . . . ? C7 C8 C13 C15 -152.42(16) . . . . ? C11 C12 C16A C17A 87.5(7) . . . . ? C7 C12 C16A C17A -94.0(7) . . . . ? C11 C12 C16A C18A -39.2(5) . . . . ? C7 C12 C16A C18A 139.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 67.15 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.151 _refine_diff_density_min -0.132 _refine_diff_density_rms 0.025