#------------------------------------------------------------------------------ #$Date: 2016-03-21 04:34:33 +0200 (Mon, 21 Mar 2016) $ #$Revision: 178473 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/02/94/4029451.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_4029451 loop_ _publ_author_name 'Wang, Siyuan' 'Otani, Yuko' 'Liu, Xin' 'Kawahata, Masatoshi' 'Yamaguchi, Kentaro' 'Ohwada, Tomohiko' _publ_section_title ; Robust trans-Amide Helical Structure of Oligomers of Bicyclic Mimics of \b-Proline: Impact of Positional Switching of Bridgehead Substituent on Amide cis-trans Equilibrium. ; _journal_issue 11 _journal_name_full 'The Journal of organic chemistry' _journal_page_first 5287 _journal_page_last 5300 _journal_paper_doi 10.1021/jo500916j _journal_volume 79 _journal_year 2014 _chemical_absolute_configuration unk _chemical_formula_sum 'C14 H23 N O5' _chemical_formula_weight 285.33 _chemical_name_systematic ; ? ; _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 110.277(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 7.321(6) _cell_length_b 11.808(9) _cell_length_c 9.419(8) _cell_measurement_reflns_used 2483 _cell_measurement_temperature 120 _cell_measurement_theta_max 22.72 _cell_measurement_theta_min 2.31 _cell_volume 763.8(11) _computing_cell_refinement SMART _computing_data_collection SMART _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP-3 for Windows' _computing_publication_material SHELXL-97 _computing_structure_refinement SHELXL-97 _computing_structure_solution SHELXS-97 _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean 8.333 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0490 _diffrn_reflns_av_sigmaI/netI 0.0633 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 8484 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 27.59 _diffrn_reflns_theta_min 2.30 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 308 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.156 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.036 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(8) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 189 _refine_ls_number_reflns 3479 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.951 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0371 _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^)+(0.0339P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0765 _refine_ls_wR_factor_ref 0.0803 _reflns_number_gt 2747 _reflns_number_total 3479 _reflns_threshold_expression >2sigma(I) _cod_data_source_file jo500916j_si_001.cif _cod_data_source_block wsy-02-121#991064 _cod_depositor_comments 'Adding full bibliography for 4029450--4029455.cif.' _cod_original_sg_symbol_H-M P21 _cod_database_code 4029451 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 C1 C 0.2673(2) 0.53659(13) 0.29217(18) 0.0220(3) Uani 1 1 d . H1 H 0.3329 0.5508 0.2167 0.026 Uiso 1 1 calc R C2 C 0.4126(2) 0.47094(12) 0.42926(17) 0.0188(3) Uani 1 1 d . C3 C 0.3148(2) 0.44845(14) 0.54739(18) 0.0259(4) Uani 1 1 d . H3A H 0.2494 0.5175 0.5657 0.031 Uiso 1 1 calc R H3B H 0.4115 0.4228 0.6445 0.031 Uiso 1 1 calc R C4 C 0.1648(2) 0.35402(16) 0.4749(2) 0.0301(4) Uani 1 1 d . H4A H 0.1975 0.2829 0.5341 0.036 Uiso 1 1 calc R H4B H 0.0311 0.3776 0.4650 0.036 Uiso 1 1 calc R C5 C 0.1865(2) 0.34089(14) 0.32125(19) 0.0239(4) Uani 1 1 d . H5 H 0.1355 0.2677 0.2692 0.029 Uiso 1 1 calc R C6 C 0.1046(2) 0.44715(14) 0.22484(19) 0.0267(4) Uani 1 1 d . H6A H -0.0194 0.4716 0.2354 0.032 Uiso 1 1 calc R H6B H 0.0829 0.4331 0.1166 0.032 Uiso 1 1 calc R C7 C 0.2016(3) 0.64873(14) 0.33393(19) 0.0282(4) Uani 1 1 d . C8 C 0.6108(2) 0.52423(13) 0.49567(17) 0.0203(3) Uani 1 1 d . H8A H 0.6634 0.5411 0.4143 0.024 Uiso 1 1 calc R H8B H 0.6011 0.5962 0.5465 0.024 Uiso 1 1 calc R C9 C 0.9126(2) 0.50148(16) 0.69322(19) 0.0304(4) Uani 1 1 d . H9A H 0.8842 0.5555 0.7618 0.046 Uiso 1 1 calc R H9B H 0.9703 0.5417 0.6280 0.046 Uiso 1 1 calc R H9C H 1.0042 0.4442 0.7526 0.046 Uiso 1 1 calc R C10 C 0.4902(2) 0.33220(13) 0.25953(18) 0.0202(3) Uani 1 1 d . C11 C 0.4659(2) 0.20104(14) 0.05145(18) 0.0257(4) Uani 1 1 d . C12 C 0.6780(3) 0.1648(2) 0.1100(2) 0.0411(5) Uani 1 1 d . H12A H 0.7001 0.1122 0.1947 0.062 Uiso 1 1 calc R H12B H 0.7611 0.2316 0.1443 0.062 Uiso 1 1 calc R H12C H 0.7098 0.1274 0.0286 0.062 Uiso 1 1 calc R C13 C 0.3349(3) 0.10027(18) -0.0050(2) 0.0451(5) Uani 1 1 d . H13A H 0.1986 0.1248 -0.0387 0.068 Uiso 1 1 calc R H13B H 0.3584 0.0449 0.0769 0.068 Uiso 1 1 calc R H13C H 0.3624 0.0655 -0.0899 0.068 Uiso 1 1 calc R C14 C 0.4243(3) 0.29138(18) -0.0684(2) 0.0442(5) Uani 1 1 d . H14A H 0.5118 0.3558 -0.0295 0.066 Uiso 1 1 calc R H14B H 0.2889 0.3165 -0.0955 0.066 Uiso 1 1 calc R H14C H 0.4451 0.2606 -0.1582 0.066 Uiso 1 1 calc R N1 N 0.40066(17) 0.35607(11) 0.36219(14) 0.0181(3) Uani 1 1 d . O1 O 0.32762(19) 0.72997(11) 0.33584(15) 0.0338(3) Uani 1 1 d . O2 O 0.0575(2) 0.66425(12) 0.3647(2) 0.0595(5) Uani 1 1 d . O3 O 0.73723(15) 0.44789(9) 0.60227(13) 0.0279(3) Uani 1 1 d . O4 O 0.62901(16) 0.38297(10) 0.24860(13) 0.0300(3) Uani 1 1 d . O5 O 0.40669(16) 0.24085(9) 0.17772(12) 0.0256(3) Uani 1 1 d . H1A H 0.299(3) 0.794(2) 0.362(3) 0.061(8) Uiso 1 1 d . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0223(8) 0.0184(8) 0.0250(8) -0.0014(7) 0.0078(7) 0.0003(6) C2 0.0203(7) 0.0145(8) 0.0230(8) -0.0024(6) 0.0093(6) -0.0004(6) C3 0.0256(8) 0.0275(9) 0.0282(9) -0.0043(7) 0.0138(7) -0.0020(7) C4 0.0284(9) 0.0310(9) 0.0378(10) -0.0020(8) 0.0203(8) -0.0045(8) C5 0.0181(8) 0.0210(8) 0.0334(9) -0.0059(7) 0.0097(7) -0.0030(7) C6 0.0182(8) 0.0249(8) 0.0321(9) -0.0049(7) 0.0026(7) 0.0004(7) C7 0.0255(9) 0.0226(9) 0.0340(10) -0.0017(8) 0.0071(8) 0.0038(7) C8 0.0192(7) 0.0173(8) 0.0225(8) 0.0000(6) 0.0049(6) -0.0004(6) C9 0.0201(8) 0.0313(10) 0.0342(10) -0.0057(8) 0.0024(7) -0.0002(8) C10 0.0203(8) 0.0186(8) 0.0200(8) 0.0016(7) 0.0048(6) 0.0027(6) C11 0.0293(9) 0.0274(9) 0.0212(8) -0.0055(7) 0.0099(7) 0.0043(7) C12 0.0335(10) 0.0590(13) 0.0307(9) -0.0058(10) 0.0108(8) 0.0174(10) C13 0.0503(13) 0.0397(11) 0.0501(12) -0.0226(10) 0.0234(10) -0.0090(10) C14 0.0607(13) 0.0420(12) 0.0290(10) 0.0048(9) 0.0145(10) 0.0110(11) N1 0.0159(6) 0.0179(7) 0.0213(6) -0.0031(5) 0.0075(5) -0.0021(5) O1 0.0377(7) 0.0182(7) 0.0479(8) -0.0040(6) 0.0178(6) -0.0015(6) O2 0.0394(9) 0.0338(8) 0.1167(13) -0.0185(9) 0.0414(9) 0.0015(7) O3 0.0211(6) 0.0188(6) 0.0356(6) 0.0011(5) -0.0008(5) -0.0017(5) O4 0.0285(6) 0.0327(7) 0.0346(7) -0.0079(6) 0.0182(5) -0.0094(5) O5 0.0290(6) 0.0218(6) 0.0301(6) -0.0088(5) 0.0155(5) -0.0036(5) 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 C7 C1 C6 115.79(14) C7 C1 C2 114.03(14) C6 C1 C2 101.89(13) C7 C1 H1 108.2 C6 C1 H1 108.2 C2 C1 H1 108.2 N1 C2 C8 117.71(13) N1 C2 C3 100.14(12) C8 C2 C3 113.22(13) N1 C2 C1 100.27(12) C8 C2 C1 114.71(13) C3 C2 C1 109.16(14) C2 C3 C4 103.99(13) C2 C3 H3A 111.0 C4 C3 H3A 111.0 C2 C3 H3B 111.0 C4 C3 H3B 111.0 H3A C3 H3B 109.0 C5 C4 C3 101.63(13) C5 C4 H4A 111.4 C3 C4 H4A 111.4 C5 C4 H4B 111.4 C3 C4 H4B 111.4 H4A C4 H4B 109.3 N1 C5 C4 100.92(13) N1 C5 C6 102.35(12) C4 C5 C6 109.29(15) N1 C5 H5 114.3 C4 C5 H5 114.3 C6 C5 H5 114.3 C5 C6 C1 103.05(13) C5 C6 H6A 111.2 C1 C6 H6A 111.2 C5 C6 H6B 111.2 C1 C6 H6B 111.2 H6A C6 H6B 109.1 O2 C7 O1 123.44(17) O2 C7 C1 125.71(16) O1 C7 C1 110.83(15) O3 C8 C2 109.00(13) O3 C8 H8A 109.9 C2 C8 H8A 109.9 O3 C8 H8B 109.9 C2 C8 H8B 109.9 H8A C8 H8B 108.3 O3 C9 H9A 109.5 O3 C9 H9B 109.5 H9A C9 H9B 109.5 O3 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 O4 C10 O5 125.13(15) O4 C10 N1 125.19(14) O5 C10 N1 109.61(13) O5 C11 C13 101.96(13) O5 C11 C14 109.82(15) C13 C11 C14 110.91(17) O5 C11 C12 110.24(13) C13 C11 C12 110.61(17) C14 C11 C12 112.78(17) C11 C12 H12A 109.5 C11 C12 H12B 109.5 H12A C12 H12B 109.5 C11 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C11 C13 H13A 109.5 C11 C13 H13B 109.5 H13A C13 H13B 109.5 C11 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C11 C14 H14A 109.5 C11 C14 H14B 109.5 H14A C14 H14B 109.5 C11 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C10 N1 C2 120.98(12) C10 N1 C5 120.64(13) C2 N1 C5 96.98(11) C7 O1 H1A 114.2(16) C9 O3 C8 111.93(13) C10 O5 C11 121.03(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C7 1.507(2) C1 C6 1.553(2) C1 C2 1.565(2) C1 H1 1.0000 C2 N1 1.486(2) C2 C8 1.504(2) C2 C3 1.541(2) C3 C4 1.548(2) C3 H3A 0.9900 C3 H3B 0.9900 C4 C5 1.518(3) C4 H4A 0.9900 C4 H4B 0.9900 C5 N1 1.490(2) C5 C6 1.543(3) C5 H5 1.0000 C6 H6A 0.9900 C6 H6B 0.9900 C7 O2 1.201(2) C7 O1 1.327(2) C8 O3 1.4260(19) C8 H8A 0.9900 C8 H8B 0.9900 C9 O3 1.421(2) C9 H9A 0.9800 C9 H9B 0.9800 C9 H9C 0.9800 C10 O4 1.215(2) C10 O5 1.343(2) C10 N1 1.372(2) C11 O5 1.477(2) C11 C13 1.505(3) C11 C14 1.506(3) C11 C12 1.518(3) C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 H13A 0.9800 C13 H13B 0.9800 C13 H13C 0.9800 C14 H14A 0.9800 C14 H14B 0.9800 C14 H14C 0.9800 O1 H1A 0.85(3) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A O3 0.85(3) 1.88(3) 2.716(3) 169(2) 2_656