#------------------------------------------------------------------------------ #$Date: 2016-02-14 14:26:36 +0000 (Sun, 14 Feb 2016) $ #$Revision: 176435 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/01/2010185.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2010185 loop_ _publ_author_name 'Mackay, M.F.' 'McLeish, M.J.' 'Campbell, M.' _publ_section_title ; Two nitrogen-containing analogues of chorismic acid ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1734 _journal_page_last 1738 _journal_paper_doi 10.1107/S010827019400212X _journal_volume 50 _journal_year 1994 _chemical_formula_moiety 'C13 H23 N1 O5' _chemical_formula_sum 'C13 H23 N O5' _chemical_formula_weight 273.3 _chemical_name_systematic ; Methyl 3-[(tert-butyloxycarbonyl)amino]-4-hydroxy-cyclohexane-1-carboxylate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90.0 _cell_angle_beta 99.510(10) _cell_angle_gamma 90.0 _cell_formula_units_Z 4 _cell_length_a 14.2140(10) _cell_length_b 6.5930(10) _cell_length_c 16.5430(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 291.0(10) _cell_measurement_theta_max 40 _cell_measurement_theta_min 22 _cell_volume 1529.0(3) _computing_cell_refinement 'Rigaku-AFC software' _computing_data_collection 'Rigaku-AFC software' _computing_data_reduction 'Rigaku-AFC software' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'Xtal3.0 (Hall & Stewart, 1990)' _computing_structure_refinement SHELX76 _computing_structure_solution 'SHELX76 (Sheldrick, 1976)' _diffrn_ambient_temperature 291.0(10) _diffrn_measurement_device 'Rigaku-AFC diffractometer' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source xray_tube _diffrn_radiation_type 'Copper K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_av_sigmaI/netI 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2685 _diffrn_reflns_theta_max 65.0 _diffrn_reflns_theta_min 4.5 _diffrn_standards_decay_% <1.5 _diffrn_standards_interval_count 50 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.72 _exptl_absorpt_correction_T_max 0.801 _exptl_absorpt_correction_T_min 0.656 _exptl_absorpt_correction_type 'gaussian, SHELX76 (Sheldrick, 1976)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_meas 1.189(5) _exptl_crystal_density_method flotation _exptl_crystal_description lathe-shaped _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.21 _refine_diff_density_max 0.36 _refine_diff_density_min -0.26 _refine_ls_abs_structure_Flack 0 _refine_ls_extinction_coef 1.3E-6(1) _refine_ls_extinction_method SHELX76 _refine_ls_goodness_of_fit_obs 3.79 _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 219 _refine_ls_number_reflns 1728 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.070 _refine_ls_shift/esd_max 0.002 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.000045F^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.075 _reflns_number_observed 1728 _reflns_number_total 2134 _reflns_observed_criterion F>6.0\sF _cod_data_source_file hr1005.cif _cod_data_source_block TOZ _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '1/[\s^2^(F) + 0.000045F^2^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(F) + 0.000045F^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1529.0(5) _cod_original_sg_symbol_H-M 'P 21/n' _cod_original_formula_sum 'C13 H23 N1 O5' _cod_database_code 2010185 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 1/2-x,1/2+y,1/2-z 1/2+x,1/2-y,1/2+z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.119(4) 0.076(4) 0.061(3) -0.006(3) 0.028(3) 0.002(3) C2 0.087(4) 0.074(4) 0.066(3) -0.009(3) 0.013(3) 0.010(3) C3 0.055(2) 0.044(3) 0.066(3) 0.000(2) 0.028(2) 0.008(2) C4 0.056(2) 0.044(2) 0.062(3) 0.002(2) 0.023(2) -0.002(2) C5 0.061(3) 0.070(3) 0.087(4) 0.003(2) 0.041(3) 0.003(3) C6 0.126(5) 0.097(5) 0.083(4) 0.011(4) 0.066(4) 0.008(3) C1' 0.102(4) 0.075(4) 0.108(4) -0.023(4) 0.040(4) 0.010(3) O1' 0.128(4) 0.113(4) 0.275(6) -0.015(3) 0.020(4) 0.075(4) O2' 0.119(3) 0.107(3) 0.166(4) -0.016(3) -0.024(3) 0.038(3) C2' 0.153(6) 0.078(4) 0.163(6) 0.003(4) -0.011(5) 0.037(4) O4 0.062(2) 0.054(2) 0.070(2) -0.002(2) 0.011(2) -0.004(2) N3 0.057(2) 0.043(2) 0.079(2) 0.007(2) 0.035(2) 0.018(2) C7' 0.048(2) 0.052(2) 0.068(3) 0.004(2) 0.021(2) 0.009(2) O7' 0.063(2) 0.050(2) 0.095(2) 0.0060(10) 0.034(2) 0.016(2) O8' 0.060(2) 0.057(2) 0.090(2) 0.0050(10) 0.041(2) 0.018(2) C9' 0.053(2) 0.072(3) 0.087(3) 0.001(2) 0.037(2) 0.007(3) C10 0.053(3) 0.152(5) 0.120(4) 0.021(3) 0.025(3) 0.038(4) C11' 0.136(5) 0.124(5) 0.116(5) -0.030(4) 0.074(4) -0.033(4) C12 0.076(3) 0.100(4) 0.114(4) 0.000(3) 0.052(3) 0.036(3) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1 0.3059(4) -0.0170(8) 0.5034(3) C2 0.3630(4) 0.0489(9) 0.4356(3) C3 0.3186(3) -0.0193(6) 0.3494(2) C4 0.2151(3) 0.0474(6) 0.3305(2) C5 0.1604(3) -0.0413(8) 0.3931(3) C6 0.2005(5) 0.0308(10) 0.4784(3) C1' 0.3228(5) -0.2366(8) 0.5275(4) O1' 0.2652(3) -0.3616(7) 0.5267(4) O2' 0.4104(3) -0.2748(6) 0.5565(3) C2' 0.4352(4) -0.4687(8) 0.5953(4) O4 0.1748(2) -0.0127(5) 0.2491(2) N3 0.3733(2) 0.0620(5) 0.2903(2) C7' 0.4465(2) -0.0354(6) 0.2673(2) O7' 0.4679(2) -0.2113(4) 0.2827(2) O8' 0.4937(2) 0.0905(4) 0.2232(2) C9' 0.5734(3) 0.0200(6) 0.1842(3) C10' 0.6544(3) -0.0529(9) 0.2491(3) C11' 0.5398(4) -0.1411(9) 0.1222(3) C12' 0.6011(3) 0.2108(7) 0.1419(3) H2'a 0.5113 -0.4752 0.6160 H2'b 0.3986 -0.4865 0.6471 H2'c 0.4143 -0.5891 0.5518 H10'a 0.7127 -0.1046 0.2200 H10'b 0.6784 -0.0702 0.2904 H10'c 0.6297 -0.1764 0.2830 H11'a 0.5989 -0.1918 0.0938 H11'b 0.5116 -0.2676 0.1521 H11'c 0.4846 -0.0799 0.0758 H12'a 0.6601 0.1775 0.1105 H12'b 0.5401 0.2627 0.0982 H12'c 0.6219 0.3276 0.1872 H1 0.328(3) 0.079(7) 0.553(3) H2a 0.427(3) 0.015(7) 0.444(3) H2b 0.366(3) 0.202(7) 0.433(3) H3 0.320(2) -0.156(5) 0.346(2) H4 0.213(2) 0.200(5) 0.334(2) H5a 0.163(2) -0.190(6) 0.393(2) H5b 0.091(3) -0.003(6) 0.374(2) H6a 0.165(3) -0.033(7) 0.513(3) H6b 0.197(3) 0.198(8) 0.479(3) HO4 0.133(3) 0.060(6) 0.231(3) HN3 0.364(2) 0.188(5) 0.278(2) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .017 .009 International_Tables_Vol_IV H 0 0 International_Tables_Vol_IV N .029 .018 International_Tables_Vol_IV O .0471 .032 International_Tables_Vol_IV loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 1 -4 4 1 -2 -1 -2 -3 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 C1 C6 110.8(4) yes C2 C1 C1' 112.3(4) yes C6 C1 C1' 112.2(4) yes C1 C2 C3 114.0(4) yes C2 C3 C4 110.1(3) yes C2 C3 N3 109.6(3) yes C4 C3 N3 111.3(3) yes C3 C4 C5 109.7(3) yes C3 C4 O4 109.7(3) yes C5 C4 O4 111.5(3) yes C4 C5 C6 111.2(4) yes C1 C6 C5 113.1(4) yes C1 C1' O1' 126.6(5) yes C1 C1' O2' 112.9(4) yes O1' C1' O2' 120.3(4) yes C1' O2' C2' 119.3(4) yes C3 N3 C7' 123.1(3) yes N3 C7' O7' 125.5(2) yes N3 C7' O8' 109.8(2) yes O7' C7' O8' 124.7(2) yes C7' O8' C9' 122.0(3) yes O8' C9' C10' 109.9(3) yes O8' C9' C11' 110.1(3) yes O8' C9' C12' 102.5(3) yes C10' C9' C11' 112.2(3) yes C10' C9' C12' 111.3(3) yes C11' C9' C12' 110.4(3) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.551(8) yes C1 C6 1.520(9) yes C1 C1' 1.510(7) yes C2 C3 1.529(6) yes C3 C4 1.518(6) yes C3 N3 1.449(5) yes C4 C5 1.512(6) yes C4 O4 1.430(5) yes C5 C6 1.509(7) yes C1' O1' 1.160(8) yes C1' O2' 1.283(8) yes O2' C2' 1.448(7) yes N3 C7' 1.331(5) yes C7' O7' 1.215(5) yes C7' O8' 1.354(5) yes O8' C9' 1.469(6) yes C9' C10' 1.517(6) yes C9' C11' 1.499(7) yes C9' C12' 1.523(6) yes 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_publ_flag C1 C6 C5 C4 -56.7(6) yes C6 C5 C4 C3 60.9(5) yes C5 C4 C3 C2 -58.5(4) yes C4 C3 C2 C1 53.1(5) yes C3 C2 C1 C6 -47.7(6) yes C2 C1 C6 C5 48.9(6) yes C6 C1 C1' O1' 1.4(9) yes C1 C1' O2' C2' 169.4(5) yes O4 C4 C3 N3 56.8(4) yes C4 C3 N3 C7' -147.7(3) yes C2 C3 N3 C7' 90.2(4) yes C3 N3 C7' O8' -169.3(3) yes N3 C7' O8' C9' -175.2(3) yes C7' O8' C9' C12' 179.2(3) yes