#------------------------------------------------------------------------------ #$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/65/1516523.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1516523 loop_ _publ_author_name 'Kise, Naoki' 'Hamada, Yusuke' 'Sakurai, Toshihiko' _publ_section_title ; Electroreductive Coupling of Optically Active \a,\b-Unsaturated Carbonyl Compounds with Diaryl Ketones: Asymmetric Synthesis of 4,5,5-Trisubstituted \g-Butyrolactones. ; _journal_issue 12 _journal_name_full 'Organic letters' _journal_page_first 3348 _journal_page_last 3351 _journal_paper_doi 10.1021/ol5013789 _journal_volume 16 _journal_year 2014 _chemical_absolute_configuration rm _chemical_formula_moiety 'C15 H18 N2 O2' _chemical_formula_sum 'C15 H18 N2 O2' _chemical_formula_weight 258.31 _chemical_melting_point 428.0(10) _chemical_name_systematic ; (4R,5S,E)-1-but-2-enoyl-3,4-dimethyl-5-phenylimidazolidin-2-one ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 97.94(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 6.546(3) _cell_length_b 12.058(6) _cell_length_c 8.846(5) _cell_measurement_temperature 298(2) _cell_volume 691.5(6) _computing_cell_refinement PROCESS-AUTO _computing_data_collection PROCESS-AUTO _computing_data_reduction PROCESS-AUTO _computing_publication_material yadokari-XG _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 10.00 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 6124 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 3.14 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 0.9835 _exptl_absorpt_correction_T_min 0.9595 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 276 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.094 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.028 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(11) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.924 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 175 _refine_ls_number_reflns 3032 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.924 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0358 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0526P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0784 _refine_ls_wR_factor_ref 0.0828 _reflns_number_gt 2246 _reflns_number_total 3032 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ol5013789_si_002.cif _cod_data_source_block 2a _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '427-429' was changed to '428.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius Adding full bibliography for 1516523--1516526.cif. ; _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 1516523 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 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 N1 N 0.79590(17) 0.23709(10) 1.04951(13) 0.0420(3) Uani 1 1 d . C1 C 0.6473(2) 0.30771(12) 0.97161(17) 0.0450(3) Uani 1 1 d . N2 N 0.7327(2) 0.35430(11) 0.85806(15) 0.0506(3) Uani 1 1 d . C2 C 0.9562(2) 0.33531(13) 0.87222(17) 0.0468(4) Uani 1 1 d . H1 H 1.0267 0.3960 0.9319 0.056 Uiso 1 1 calc R C3 C 0.9779(2) 0.22920(13) 0.96975(16) 0.0443(3) Uani 1 1 d . H2 H 1.1034 0.2335 1.0440 0.053 Uiso 1 1 calc R C4 C 0.7963(3) 0.18479(13) 1.18834(18) 0.0472(4) Uani 1 1 d . O1 O 0.9449(2) 0.12875(11) 1.23800(13) 0.0665(3) Uani 1 1 d . C5 C 0.6186(3) 0.20254(13) 1.27073(18) 0.0528(4) Uani 1 1 d . H3 H 0.5030 0.2393 1.2221 0.063 Uiso 1 1 calc R C6 C 0.6198(3) 0.16779(14) 1.4107(2) 0.0595(5) Uani 1 1 d . H4 H 0.7366 0.1307 1.4568 0.071 Uiso 1 1 calc R C7 C 0.4459(3) 0.1837(2) 1.5016(2) 0.0800(6) Uani 1 1 d . H5 H 0.4904 0.2301 1.5880 0.120 Uiso 1 1 calc R H6 H 0.4036 0.1129 1.5363 0.120 Uiso 1 1 calc R H7 H 0.3320 0.2181 1.4389 0.120 Uiso 1 1 calc R O2 O 0.47130(17) 0.32230(11) 0.99909(14) 0.0631(3) Uani 1 1 d . C8 C 0.6355(3) 0.44827(16) 0.7756(2) 0.0701(5) Uani 1 1 d . H8 H 0.4982 0.4572 0.8003 0.105 Uiso 1 1 calc R H9 H 0.6296 0.4359 0.6679 0.105 Uiso 1 1 calc R H10 H 0.7142 0.5141 0.8038 0.105 Uiso 1 1 calc R C9 C 1.0345(3) 0.33020(16) 0.72011(19) 0.0607(5) Uani 1 1 d . H11 H 0.9547 0.2773 0.6557 0.091 Uiso 1 1 calc R H12 H 1.1767 0.3080 0.7349 0.091 Uiso 1 1 calc R H13 H 1.0219 0.4020 0.6728 0.091 Uiso 1 1 calc R C10 C 0.9793(2) 0.12408(13) 0.87983(16) 0.0443(3) Uani 1 1 d . C11 C 0.8023(3) 0.06621(15) 0.8275(2) 0.0560(4) Uani 1 1 d . H14 H 0.6764 0.0910 0.8520 0.067 Uiso 1 1 calc R C12 C 0.8081(3) -0.02754(16) 0.7398(2) 0.0666(5) Uani 1 1 d . H15 H 0.6871 -0.0658 0.7057 0.080 Uiso 1 1 calc R C13 C 0.9927(3) -0.06436(16) 0.7030(2) 0.0665(5) Uani 1 1 d . H16 H 0.9969 -0.1264 0.6411 0.080 Uiso 1 1 calc R C14 C 1.1713(3) -0.00968(16) 0.7576(2) 0.0698(5) Uani 1 1 d . H17 H 1.2969 -0.0361 0.7346 0.084 Uiso 1 1 calc R C15 C 1.1666(3) 0.08350(15) 0.8457(2) 0.0618(5) Uani 1 1 d . H18 H 1.2888 0.1197 0.8827 0.074 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 N1 0.0424(7) 0.0420(6) 0.0431(6) 0.0034(6) 0.0114(5) 0.0016(6) C1 0.0430(8) 0.0419(8) 0.0499(9) -0.0006(7) 0.0051(6) 0.0007(7) N2 0.0508(7) 0.0433(7) 0.0576(8) 0.0100(6) 0.0075(6) 0.0027(6) C2 0.0476(8) 0.0408(8) 0.0522(9) 0.0002(7) 0.0078(6) -0.0052(7) C3 0.0399(7) 0.0487(9) 0.0450(8) 0.0031(7) 0.0079(6) 0.0006(7) C4 0.0558(10) 0.0402(8) 0.0466(8) 0.0005(7) 0.0107(7) -0.0006(8) O1 0.0717(8) 0.0702(8) 0.0594(7) 0.0189(6) 0.0150(6) 0.0226(7) C5 0.0601(10) 0.0474(9) 0.0533(9) 0.0022(7) 0.0166(8) -0.0023(8) C6 0.0690(12) 0.0578(10) 0.0542(9) -0.0012(8) 0.0172(8) -0.0053(9) C7 0.0929(15) 0.0894(15) 0.0637(11) -0.0014(11) 0.0326(11) -0.0081(12) O2 0.0449(6) 0.0687(8) 0.0767(8) 0.0120(6) 0.0121(5) 0.0095(6) C8 0.0727(12) 0.0534(11) 0.0809(14) 0.0207(10) -0.0015(10) 0.0058(9) C9 0.0718(11) 0.0596(11) 0.0534(10) 0.0086(8) 0.0185(8) -0.0056(10) C10 0.0437(8) 0.0447(8) 0.0467(8) 0.0074(7) 0.0136(6) 0.0046(7) C11 0.0485(10) 0.0529(10) 0.0666(11) -0.0072(9) 0.0077(8) 0.0045(8) C12 0.0726(13) 0.0545(11) 0.0713(12) -0.0098(9) 0.0045(9) 0.0046(10) C13 0.0965(16) 0.0475(9) 0.0592(11) 0.0016(9) 0.0238(11) 0.0145(11) C14 0.0733(13) 0.0572(11) 0.0876(14) 0.0060(10) 0.0416(11) 0.0172(11) C15 0.0523(10) 0.0560(10) 0.0819(12) 0.0026(9) 0.0264(9) 0.0035(9) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C4 N1 C1 129.15(12) C4 N1 C3 119.73(12) C1 N1 C3 110.94(12) O2 C1 N2 126.27(15) O2 C1 N1 126.82(14) N2 C1 N1 106.89(13) C1 N2 C8 120.44(14) C1 N2 C2 112.64(13) C8 N2 C2 121.92(14) N2 C2 C9 112.83(14) N2 C2 C3 101.02(11) C9 C2 C3 116.78(13) N2 C2 H1 108.6 C9 C2 H1 108.6 C3 C2 H1 108.6 N1 C3 C10 112.02(12) N1 C3 C2 101.38(12) C10 C3 C2 114.39(12) N1 C3 H2 109.6 C10 C3 H2 109.6 C2 C3 H2 109.6 O1 C4 N1 118.57(14) O1 C4 C5 123.36(15) N1 C4 C5 118.04(14) C6 C5 C4 121.44(16) C6 C5 H3 119.3 C4 C5 H3 119.3 C5 C6 C7 124.35(18) C5 C6 H4 117.8 C7 C6 H4 117.8 C6 C7 H5 109.5 C6 C7 H6 109.5 H5 C7 H6 109.5 C6 C7 H7 109.5 H5 C7 H7 109.5 H6 C7 H7 109.5 N2 C8 H8 109.5 N2 C8 H9 109.5 H8 C8 H9 109.5 N2 C8 H10 109.5 H8 C8 H10 109.5 H9 C8 H10 109.5 C2 C9 H11 109.5 C2 C9 H12 109.5 H11 C9 H12 109.5 C2 C9 H13 109.5 H11 C9 H13 109.5 H12 C9 H13 109.5 C11 C10 C15 118.36(16) C11 C10 C3 122.74(14) C15 C10 C3 118.90(15) C12 C11 C10 121.25(16) C12 C11 H14 119.4 C10 C11 H14 119.4 C13 C12 C11 119.69(19) C13 C12 H15 120.2 C11 C12 H15 120.2 C12 C13 C14 119.92(18) C12 C13 H16 120.0 C14 C13 H16 120.0 C15 C14 C13 120.63(17) C15 C14 H17 119.7 C13 C14 H17 119.7 C14 C15 C10 120.09(18) C14 C15 H18 120.0 C10 C15 H18 120.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C4 1.380(2) N1 C1 1.4005(19) N1 C3 1.469(2) C1 O2 1.2225(18) C1 N2 1.339(2) N2 C8 1.447(2) N2 C2 1.469(2) C2 C9 1.506(2) C2 C3 1.539(2) C2 H1 0.9800 C3 C10 1.497(2) C3 H2 0.9800 C4 O1 1.216(2) C4 C5 1.471(2) C5 C6 1.306(2) C5 H3 0.9300 C6 C7 1.494(3) C6 H4 0.9300 C7 H5 0.9600 C7 H6 0.9600 C7 H7 0.9600 C8 H8 0.9600 C8 H9 0.9600 C8 H10 0.9600 C9 H11 0.9600 C9 H12 0.9600 C9 H13 0.9600 C10 C11 1.377(2) C10 C15 1.392(2) C11 C12 1.374(3) C11 H14 0.9300 C12 C13 1.368(3) C12 H15 0.9300 C13 C14 1.371(3) C13 H16 0.9300 C14 C15 1.370(3) C14 H17 0.9300 C15 H18 0.9300 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 C4 N1 C1 O2 -13.5(2) C3 N1 C1 O2 171.57(15) C4 N1 C1 N2 168.16(15) C3 N1 C1 N2 -6.78(16) O2 C1 N2 C8 14.4(2) N1 C1 N2 C8 -167.22(14) O2 C1 N2 C2 169.87(15) N1 C1 N2 C2 -11.78(16) C1 N2 C2 C9 149.49(14) C8 N2 C2 C9 -55.5(2) C1 N2 C2 C3 24.04(15) C8 N2 C2 C3 179.07(15) C4 N1 C3 C10 82.91(16) C1 N1 C3 C10 -101.62(15) C4 N1 C3 C2 -154.69(13) C1 N1 C3 C2 20.78(15) N2 C2 C3 N1 -25.16(14) C9 C2 C3 N1 -147.91(14) N2 C2 C3 C10 95.58(14) C9 C2 C3 C10 -27.17(19) C1 N1 C4 O1 -177.97(14) C3 N1 C4 O1 -3.4(2) C1 N1 C4 C5 0.3(2) C3 N1 C4 C5 174.83(13) O1 C4 C5 C6 7.1(3) N1 C4 C5 C6 -171.06(16) C4 C5 C6 C7 179.50(17) N1 C3 C10 C11 24.5(2) C2 C3 C10 C11 -90.11(17) N1 C3 C10 C15 -156.29(14) C2 C3 C10 C15 89.06(18) C15 C10 C11 C12 -1.9(2) C3 C10 C11 C12 177.24(16) C10 C11 C12 C13 -0.2(3) C11 C12 C13 C14 2.0(3) C12 C13 C14 C15 -1.7(3) C13 C14 C15 C10 -0.4(3) C11 C10 C15 C14 2.2(3) C3 C10 C15 C14 -176.98(16)