############################################################################ # # # # # ### # # ### ### # ### # # ### # # ### # ### # # # # # # # # # # # # # ## ## # ## # # # # # # # # # # ### # # ### ### # ### # # # ### # ## # ### ### # # # # # # # # # # # # # # # # # # ## # # # ### ### # # ### ### # # ### # # # # # # # # # # # # # # # # # ### ### ### # # # # # ## ## # # # # # # # # # # # # # # # ### # ### ### # ### # # # # # # # # # ## # # # # # # # # # # # ### # # # # # ### # # # # # ############################################################################ ############################################################################ # # # This Supplementary Material is written in the Crystallographic # # Information File (CIF) format. For further details see: S.R. Hall, # # F.H. Allen and I.D. Brown, Acta Cryst. (1991) A47, 655-685. # # # ############################################################################ data_5679sad ############################################################################ # # _publ_requested_journal 'test' #_publ_requested_category ?FI ; full inorganic #_publ_requested_category ?FM ; full organometallic #_publ_requested_category ?FO ; full organic #?If CI, CM or CO remember to remove section "..._molecular_graphics" #_publ_requested_category ?CI ; electronic inorganic #_publ_requested_category ?CM ; electronic organometallic #_publ_requested_category ?CO ; electronic organic _publ_section_title ; ? ; loop_ _publ_author_name _publ_author_address 'Krause' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; 'F\"urstner' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; 'Lehmann' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; # # ############################################################################ _audit_creation_date 2006-12-04 _audit_block_code 'KHS-HC-174-04' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_compound_source 'CH2Cl2/Et2O' _chemical_formula_moiety 'C19 H21 N3 O2' _chemical_formula_sum 'C19 H21 N3 O2' _chemical_formula_weight 323.39 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 'P21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 8.1878(2) _cell_length_b 14.1611(4) _cell_length_c 14.4546(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.6920(10) _cell_angle_gamma 90.00 _cell_volume 1674.14(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 12913 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 33.14 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method none _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.681 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS, Bruker AXS (2004)' _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 1.00 _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_monochromator 'focusing multilayer optic' _diffrn_measurement_device_type 'Bruker AXS X8 Proteum' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 12401 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.37 _diffrn_reflns_theta_max 63.48 _reflns_number_total 2538 _reflns_number_gt 2235 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'PROTEUM2 (Bruker AXS, 2004)' _computing_cell_refinement 'PROTEUM2 (Bruker AXS, 2004)' _computing_data_reduction 'SAINT software (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _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^)+(0.0417P)^2^+0.5535P] 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_number_reflns 2538 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0842 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _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 C1 C 0.15249(18) 0.70906(11) 0.04722(10) 0.0199(4) Uani 1 1 d . . . C2 C 0.26518(18) 0.73773(11) -0.01653(10) 0.0207(4) Uani 1 1 d . . . H2 H 0.2797 0.7009 -0.0705 0.025 Uiso 1 1 calc R . . C3 C 0.35616(18) 0.81929(11) -0.00206(10) 0.0201(4) Uani 1 1 d . . . H3 H 0.4297 0.8391 -0.0471 0.024 Uiso 1 1 calc R . . C4 C 0.34068(19) 0.87243(10) 0.07805(10) 0.0199(4) Uani 1 1 d . . . C5 C 0.21176(19) 0.85177(11) 0.13440(10) 0.0212(4) Uani 1 1 d . . . H5 H 0.1882 0.8928 0.1841 0.025 Uiso 1 1 calc R . . C6 C 0.11799(18) 0.77162(11) 0.11809(10) 0.0210(4) Uani 1 1 d . . . H6 H 0.0286 0.7591 0.1559 0.025 Uiso 1 1 calc R . . C11 C 0.09370(19) 0.60856(11) 0.04906(10) 0.0230(4) Uani 1 1 d . . . H11A H 0.1253 0.5756 -0.0078 0.028 Uiso 1 1 calc R . . H11B H -0.0271 0.6076 0.0505 0.028 Uiso 1 1 calc R . . C12 C 0.16900(18) 0.55647(11) 0.13553(11) 0.0225(4) Uani 1 1 d . . . H12A H 0.1078 0.5753 0.1901 0.027 Uiso 1 1 calc R . . H12B H 0.1531 0.4877 0.1265 0.027 Uiso 1 1 calc R . . C13 C 0.34987(18) 0.57492(10) 0.15693(10) 0.0190(3) Uani 1 1 d . . . C14 C 0.39213(18) 0.63947(10) 0.23482(10) 0.0203(4) Uani 1 1 d . . . H14 H 0.3404 0.6239 0.2903 0.024 Uiso 1 1 calc R . . C15 C 0.48908(18) 0.71563(11) 0.24266(10) 0.0198(3) Uani 1 1 d . . . H15 H 0.5028 0.7395 0.3039 0.024 Uiso 1 1 calc R . . C16 C 0.57843(17) 0.76910(10) 0.17326(10) 0.0182(3) Uani 1 1 d . . . C17 C 0.58839(19) 0.87543(11) 0.18621(10) 0.0216(4) Uani 1 1 d . . . H17A H 0.7038 0.8953 0.1825 0.026 Uiso 1 1 calc R . . H17B H 0.5536 0.8912 0.2490 0.026 Uiso 1 1 calc R . . C18 C 0.48144(19) 0.93307(11) 0.11367(11) 0.0225(4) Uani 1 1 d . . . H18A H 0.4393 0.9908 0.1429 0.027 Uiso 1 1 calc R . . H18B H 0.5485 0.9523 0.0617 0.027 Uiso 1 1 calc R . . C21 C 0.46227(18) 0.52275(11) 0.11577(10) 0.0205(4) Uani 1 1 d . . . H21 H 0.4275 0.4844 0.0646 0.025 Uiso 1 1 calc R . . C22 C 0.6321(2) 0.52174(11) 0.14474(10) 0.0215(4) Uani 1 1 d . . . N23 N 0.76595(18) 0.51291(10) 0.17110(9) 0.0291(3) Uani 1 1 d . . . N31 N 0.64135(15) 0.72197(9) 0.10764(8) 0.0191(3) Uani 1 1 d . . . O32 O 0.72097(12) 0.78783(7) 0.04907(7) 0.0201(3) Uani 1 1 d . . . O33 O 0.71560(13) 0.66898(7) -0.05865(7) 0.0248(3) Uani 1 1 d . . . C34 C 0.75698(17) 0.74754(11) -0.03462(10) 0.0189(3) Uani 1 1 d . . . N35 N 0.83826(15) 0.81039(9) -0.08539(8) 0.0213(3) Uani 1 1 d . . . C36 C 0.8945(2) 0.90279(11) -0.05248(11) 0.0258(4) Uani 1 1 d . . . H36A H 0.8283 0.9232 -0.0014 0.039 Uiso 1 1 calc R . . H36B H 0.8835 0.9486 -0.1032 0.039 Uiso 1 1 calc R . . H36C H 1.0095 0.8986 -0.0307 0.039 Uiso 1 1 calc R . . C37 C 0.9036(2) 0.77934(12) -0.17204(10) 0.0258(4) Uani 1 1 d . . . H37A H 1.0233 0.7784 -0.1659 0.039 Uiso 1 1 calc R . . H37B H 0.8683 0.8229 -0.2217 0.039 Uiso 1 1 calc R . . H37C H 0.8632 0.7157 -0.1869 0.039 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 C1 0.0162(8) 0.0218(9) 0.0210(8) 0.0014(6) -0.0060(6) 0.0020(6) C2 0.0212(9) 0.0236(9) 0.0169(8) -0.0005(6) -0.0035(6) 0.0030(6) C3 0.0194(9) 0.0213(9) 0.0194(8) 0.0048(6) -0.0008(6) 0.0009(6) C4 0.0225(9) 0.0150(8) 0.0217(8) 0.0031(6) -0.0033(6) 0.0031(6) C5 0.0243(9) 0.0184(9) 0.0208(8) 0.0001(6) -0.0013(6) 0.0061(6) C6 0.0172(9) 0.0244(9) 0.0214(8) 0.0048(7) -0.0008(6) 0.0028(6) C11 0.0212(9) 0.0227(9) 0.0247(8) 0.0001(7) -0.0023(7) -0.0016(6) C12 0.0203(9) 0.0197(9) 0.0275(8) 0.0017(7) 0.0011(6) -0.0022(6) C13 0.0221(9) 0.0161(8) 0.0187(8) 0.0067(6) 0.0004(6) -0.0017(6) C14 0.0204(9) 0.0216(9) 0.0190(8) 0.0047(6) 0.0015(6) 0.0042(6) C15 0.0214(9) 0.0212(9) 0.0165(7) 0.0007(6) -0.0027(6) 0.0038(6) C16 0.0166(8) 0.0201(9) 0.0173(8) 0.0001(6) -0.0059(6) 0.0007(6) C17 0.0259(9) 0.0193(9) 0.0194(8) -0.0027(6) -0.0014(6) -0.0015(6) C18 0.0261(9) 0.0159(8) 0.0254(8) -0.0006(6) -0.0005(7) 0.0009(6) C21 0.0226(9) 0.0200(9) 0.0189(8) 0.0025(6) 0.0010(6) -0.0030(6) C22 0.0257(11) 0.0165(9) 0.0226(8) 0.0029(6) 0.0058(7) 0.0011(6) N23 0.0261(9) 0.0268(8) 0.0345(8) 0.0075(6) 0.0044(6) 0.0031(6) N31 0.0198(7) 0.0184(7) 0.0189(7) 0.0040(5) -0.0004(5) -0.0025(5) O32 0.0233(6) 0.0177(6) 0.0194(5) 0.0003(4) 0.0033(4) -0.0029(4) O33 0.0286(7) 0.0203(6) 0.0257(6) -0.0046(5) 0.0015(5) -0.0047(5) C34 0.0164(8) 0.0198(9) 0.0201(8) -0.0004(7) -0.0024(6) 0.0022(6) N35 0.0229(7) 0.0209(7) 0.0201(7) 0.0006(5) 0.0021(5) -0.0035(5) C36 0.0280(10) 0.0206(9) 0.0289(9) 0.0020(7) 0.0018(7) -0.0030(7) C37 0.0240(9) 0.0331(10) 0.0203(8) 0.0000(7) 0.0003(7) -0.0015(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 C1 C6 1.393(2) . Y C1 C2 1.395(2) . Y C1 C11 1.503(2) . Y C2 C3 1.385(2) . Y C2 H2 0.9500 . N C3 C4 1.392(2) . Y C3 H3 0.9500 . N C4 C5 1.394(2) . Y C4 C18 1.508(2) . Y C5 C6 1.384(2) . Y C5 H5 0.9500 . N C6 H6 0.9500 . N C11 C12 1.554(2) . Y C11 H11A 0.9900 . N C11 H11B 0.9900 . N C12 C13 1.521(2) . Y C12 H12A 0.9900 . N C12 H12B 0.9900 . N C13 C21 1.341(2) . Y C13 C14 1.479(2) . Y C14 C15 1.341(2) . Y C14 H14 0.9500 . N C15 C16 1.478(2) . Y C15 H15 0.9500 . N C16 N31 1.2870(19) . Y C16 C17 1.519(2) . Y C17 C18 1.564(2) . Y C17 H17A 0.9900 . N C17 H17B 0.9900 . N C18 H18A 0.9900 . N C18 H18B 0.9900 . N C21 C22 1.433(2) . Y C21 H21 0.9500 . N C22 N23 1.1502(19) . Y N31 O32 1.4365(15) . Y O32 C34 1.3818(18) . Y O33 C34 1.2092(18) . Y C34 N35 1.3489(19) . Y N35 C37 1.453(2) . Y N35 C36 1.459(2) . Y C36 H36A 0.9800 . N C36 H36B 0.9800 . N C36 H36C 0.9800 . N C37 H37A 0.9800 . N C37 H37B 0.9800 . N C37 H37C 0.9800 . N 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 C1 C2 117.64(14) . . Y C6 C1 C11 120.86(13) . . Y C2 C1 C11 120.64(14) . . Y C3 C2 C1 120.72(14) . . Y C3 C2 H2 119.6 . . N C1 C2 H2 119.6 . . N C2 C3 C4 120.48(14) . . Y C2 C3 H3 119.8 . . N C4 C3 H3 119.8 . . N C3 C4 C5 118.27(14) . . Y C3 C4 C18 119.59(14) . . Y C5 C4 C18 120.49(13) . . Y C6 C5 C4 120.10(14) . . Y C6 C5 H5 119.9 . . N C4 C5 H5 119.9 . . N C5 C6 C1 121.10(14) . . Y C5 C6 H6 119.4 . . N C1 C6 H6 119.4 . . N C1 C11 C12 110.39(12) . . Y C1 C11 H11A 109.6 . . N C12 C11 H11A 109.6 . . N C1 C11 H11B 109.6 . . N C12 C11 H11B 109.6 . . N H11A C11 H11B 108.1 . . N C13 C12 C11 115.33(12) . . Y C13 C12 H12A 108.4 . . N C11 C12 H12A 108.4 . . N C13 C12 H12B 108.4 . . N C11 C12 H12B 108.4 . . N H12A C12 H12B 107.5 . . N C21 C13 C14 122.51(13) . . Y C21 C13 C12 119.81(13) . . Y C14 C13 C12 116.86(13) . . Y C15 C14 C13 132.70(14) . . Y C15 C14 H14 113.7 . . N C13 C14 H14 113.7 . . N C14 C15 C16 131.66(14) . . Y C14 C15 H15 114.2 . . N C16 C15 H15 114.2 . . N N31 C16 C15 117.56(13) . . Y N31 C16 C17 125.72(13) . . Y C15 C16 C17 116.72(12) . . Y C16 C17 C18 114.17(12) . . Y C16 C17 H17A 108.7 . . N C18 C17 H17A 108.7 . . N C16 C17 H17B 108.7 . . N C18 C17 H17B 108.7 . . N H17A C17 H17B 107.6 . . N C4 C18 C17 109.06(12) . . Y C4 C18 H18A 109.9 . . N C17 C18 H18A 109.9 . . N C4 C18 H18B 109.9 . . N C17 C18 H18B 109.9 . . N H18A C18 H18B 108.3 . . N C13 C21 C22 123.53(14) . . Y C13 C21 H21 118.2 . . N C22 C21 H21 118.2 . . N N23 C22 C21 173.81(16) . . Y C16 N31 O32 107.82(11) . . Y C34 O32 N31 111.67(10) . . Y O33 C34 N35 126.13(14) . . Y O33 C34 O32 124.26(13) . . Y N35 C34 O32 109.57(12) . . Y C34 N35 C37 118.70(13) . . Y C34 N35 C36 124.78(12) . . Y C37 N35 C36 115.41(12) . . Y N35 C36 H36A 109.5 . . N N35 C36 H36B 109.5 . . N H36A C36 H36B 109.5 . . N N35 C36 H36C 109.5 . . N H36A C36 H36C 109.5 . . N H36B C36 H36C 109.5 . . N N35 C37 H37A 109.5 . . N N35 C37 H37B 109.5 . . N H37A C37 H37B 109.5 . . N N35 C37 H37C 109.5 . . N H37A C37 H37C 109.5 . . N H37B C37 H37C 109.5 . . N _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 63.48 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 0.183 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.040