#------------------------------------------------------------------------------ #$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201982 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/10/90/4109054.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_4109054 loop_ _publ_author_name 'Hahn Kim' 'Stephen D. Goble' 'Chulbom Lee' _publ_contact_author_address ; Princeton University Department of Chemistry Princeton, NJ 08544-1009 USA ; _publ_contact_author_email cblee@princeton.edu _publ_contact_author_fax '(609) 258 6746' _publ_contact_author_name 'Professor Chulbom Lee' _publ_contact_author_phone '(609) 258 6253' _publ_section_title ; Ruthenium-Catalyzed Carboxylative Cyclization of 1,6-Diynes ; _journal_name_full 'Journal of the American Chemical Society' _journal_page_first 1030 _journal_page_last 1031 _journal_paper_doi 10.1021/ja067336e _journal_volume 129 _journal_year 2007 _chemical_absolute_configuration unk _chemical_compound_source 'chemical synthesis' _chemical_formula_iupac 'C18 H18 O6' _chemical_formula_moiety 'C18 H18 O6' _chemical_formula_structural 'C18 H18 O6' _chemical_formula_sum 'C18 H18 O6' _chemical_formula_weight 330.32 _chemical_name_systematic ; (E)-5-Benzoyloxymethylenecyclohex-3-ene-1,1-dicarboxylic Acid Dimethyl Ester ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 4 _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_date 'October 24, 2005' _audit_creation_method ; SHELXL and manual editing of form.cif ; _audit_update_record ; Oct. 24, 2005 cbl006f.cif Initial CIF created by DMH. Oct. 24, 2005 Sent to Checkcif. See cbl006f_checkcif.pdf for the alerts that were generated. PLAT024_ALERT_4_B Merging of Friedel pairs is STRONGLY indicated. REFLT03_ALERT_4_G MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases. STRVA01_ALERT_4_C Flack test results are meaningless. From the CIF: _refine_ls_abs_structure_Flack ... -0.01 From the CIF: _refine_ls_abs_structure_Flack_su . 0.90 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High .... 0.90 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ... 0.90 PLAT390_ALERT_3_C Deviating Methyl C14 X-C-H Bond Angle .... 102.70 Deg. 0 ALERT level A = In general, serious problem. 1 ALERT level B = Potentially serious problem. 4 ALERT level C = Check and explain. 1 ALERT level G = General alerts. Check. PLAT024_ALERT_4_B, REFLT03_ALERT_4_G. We have elected not to merge the Friedel pairs since: (a) The C-H bond distances were significantly poorer with the merged (versus the unmerged) data, and (b) the standard uncer- tainties for all distances and angles were also poorer with the merged (versus the unmerged) data. STRVA01_ALERT_4_C, PLAT032_ALERT_4_C, PLAT850_ALERT_2_C. Yes, the Flack test results are meaningless and absolutely no attempt is made to state what the absolute structure of the molecule is. These 3 alerts are totally consistent with the absence of a heavy atom or significant anomalous scatterer in the structure. However, the target of this study is only the relative configuration of the molecule (and not the absolute structure). Therefore, these alerts have no bearing. The relative configuration of the molecule is uneqivocally determined regardless of these alerts, nor is there any decrease in the precision or certainty of the metrical results obtained. PLAT390_ALERT_3_C. Deviations in the C-C-H angles at the methyl C(14) atom were noted, and were considered insuf- ficiently alarming to warrant restraints. As indicated in the _geom_special_details section at the end of this file, the C(14) methyl group participates in a number of inter- molecular close contacts. We elected to leave the methyl moiety unrestrained to allow it to better adjust to its surroundings. A brief discussion of the data collection, data reduction, and structure solution and refinement can be found near the middle of this file under the following headings: 7. EXPERIMENTAL DATA FOR cbl006f _exptl_special_details 8. REFINEMENT DATA FOR cbl006f _refine_special_details Also, please read the _geom_special_details section at the very bottom of this file. In that section, miscellaneous details on the structure are provided as well as selected references that may be relevant to this study. ; _cell_angle_alpha 90.00 _cell_angle_beta 108.672(1) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 10.0350(2) _cell_length_b 6.3816(1) _cell_length_c 13.8107(3) _cell_measurement_reflns_used 29751 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 27.51 _cell_measurement_theta_min 1.56 _cell_volume 837.88(3) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'Siemens SHELXTL (Sheldrick, 1996)' _computing_publication_material 'Siemens SHELXTL (Sheldrick, 1996)' _computing_structure_refinement 'Siemens SHELXTL (Sheldrick, 1996)' _computing_structure_solution 'Siemens SHELXTL (Sheldrick, 1996)' _diffrn_ambient_temperature 200(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\w scans, 550 2.0\% rotations' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_av_sigmaI/netI 0.033 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 29751 _diffrn_reflns_theta_full 27.51 _diffrn_reflns_theta_max 27.51 _diffrn_reflns_theta_min 1.56 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.309 _exptl_crystal_description Needle _exptl_crystal_F_000 348 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.230 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.039 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(90) _refine_ls_extinction_coef 0.0477(49) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_all 1.090 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 272 _refine_ls_number_reflns 3852 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.090 _refine_ls_restrained_S_gt 1.064 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0439 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.0984P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1092 _refine_ls_wR_factor_ref 0.0983 _reflns_number_gt 3311 _reflns_number_total 3852 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ja067336esi20061215_051528.cif _cod_data_source_block cbl006f _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 4109054 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0441(10) 0.0331(9) 0.0369(9) 0.0029(7) 0.0149(7) 0.0026(7) C2 0.0649(13) 0.0303(9) 0.0483(10) 0.0006(8) 0.0278(9) -0.0016(9) C3 0.0633(12) 0.0397(10) 0.0433(10) -0.0084(8) 0.0204(9) -0.0197(9) C4 0.0471(11) 0.0446(10) 0.0400(9) -0.0037(8) 0.0151(8) -0.0125(8) C5 0.0418(9) 0.0374(9) 0.0341(8) -0.0016(7) 0.0136(7) -0.0079(8) C6 0.0405(9) 0.0364(9) 0.0370(9) -0.0017(8) 0.0137(7) -0.0013(8) C7 0.0505(10) 0.0450(10) 0.0387(9) 0.0044(8) 0.0194(8) 0.0130(9) O8 0.0719(10) 0.0611(10) 0.0706(10) 0.0280(8) 0.0175(8) 0.0209(9) O9 0.0381(7) 0.0581(8) 0.0658(9) 0.0119(7) 0.0094(6) 0.0025(6) C10 0.0375(11) 0.092(2) 0.074(2) 0.006(2) 0.0087(11) 0.0079(13) C11 0.0355(9) 0.0339(8) 0.0393(9) 0.0004(7) 0.0109(7) -0.0033(7) O12 0.0555(8) 0.0366(7) 0.0526(7) 0.0107(6) 0.0192(6) 0.0085(6) O13 0.0620(8) 0.0419(7) 0.0403(7) 0.0031(5) 0.0236(6) 0.0035(6) C14 0.0678(14) 0.0547(12) 0.0382(10) 0.0040(9) 0.0203(10) -0.0081(11) C15 0.0355(9) 0.0432(9) 0.0417(9) -0.0040(8) 0.0128(7) -0.0065(8) O16 0.0349(6) 0.0412(7) 0.0464(7) -0.0087(6) 0.0131(5) -0.0008(5) C17 0.0392(10) 0.0439(9) 0.0416(9) 0.0012(8) 0.0188(8) 0.0030(8) O18 0.0368(7) 0.0665(9) 0.0602(8) -0.0078(8) 0.0168(6) 0.0056(7) C19 0.0501(11) 0.0410(10) 0.0397(9) -0.0027(7) 0.0208(8) -0.0012(7) C20 0.0669(14) 0.0484(12) 0.0665(13) -0.0095(10) 0.0390(12) -0.0023(10) C21 0.103(2) 0.0522(13) 0.077(2) -0.0233(12) 0.058(2) -0.0148(13) C22 0.089(2) 0.073(2) 0.0586(14) -0.0260(13) 0.0288(13) -0.0287(15) C23 0.0654(15) 0.0693(15) 0.0546(12) -0.0150(12) 0.0112(11) -0.0132(13) C24 0.0498(12) 0.0536(12) 0.0467(11) -0.0099(9) 0.0110(9) -0.0040(9) 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag C1 C 0.1729(2) 0.7479(3) 0.33397(13) 0.0376(4) Uani 1 d C2 C 0.2506(2) 0.9588(3) 0.3594(2) 0.0456(4) Uani 1 d H2A H 0.2180(22) 1.0484(36) 0.2961(17) 0.055 Uiso 1 d H2B H 0.2157(22) 1.0318(37) 0.4055(18) 0.055 Uiso 1 d C3 C 0.4065(2) 0.9297(3) 0.39794(15) 0.0480(5) Uani 1 d H3 H 0.4635(23) 1.0439(37) 0.4426(18) 0.058 Uiso 1 d C4 C 0.4703(2) 0.7623(3) 0.37577(14) 0.0436(4) Uani 1 d H4 H 0.5774(24) 0.7415(35) 0.4026(16) 0.052 Uiso 1 d C5 C 0.3931(2) 0.5972(3) 0.30876(13) 0.0374(4) Uani 1 d C6 C 0.2350(2) 0.6161(3) 0.26528(14) 0.0377(4) Uani 1 d H6A H 0.1927(20) 0.4715(37) 0.2559(15) 0.045 Uiso 1 d H6B H 0.2098(21) 0.6908(32) 0.1988(16) 0.045 Uiso 1 d C7 C 0.0178(2) 0.7839(3) 0.27590(13) 0.0435(4) Uani 1 d O8 O -0.0302(2) 0.9408(3) 0.23074(13) 0.0692(5) Uani 1 d O9 O -0.05978(13) 0.6170(3) 0.27978(11) 0.0557(4) Uani 1 d C10 C -0.2095(2) 0.6337(6) 0.2264(2) 0.0699(7) Uani 1 d H10A H -0.2563(34) 0.4855(62) 0.2218(25) 0.105 Uiso 1 d H10B H -0.2292(33) 0.6694(57) 0.1524(28) 0.105 Uiso 1 d H10C H -0.2495(35) 0.7476(65) 0.2567(23) 0.105 Uiso 1 d C11 C 0.1831(2) 0.6272(3) 0.43182(13) 0.0365(4) Uani 1 d O12 O 0.22768(14) 0.4528(2) 0.45150(10) 0.0478(3) Uani 1 d O13 O 0.13310(14) 0.7440(2) 0.49292(9) 0.0464(3) Uani 1 d C14 C 0.1235(3) 0.6419(4) 0.5845(2) 0.0528(5) Uani 1 d H14A H 0.0718(29) 0.7518(47) 0.6143(20) 0.079 Uiso 1 d H14B H 0.2209(29) 0.6218(49) 0.6348(21) 0.079 Uiso 1 d H14C H 0.0693(29) 0.5048(45) 0.5665(21) 0.079 Uiso 1 d C15 C 0.4612(2) 0.4397(3) 0.28256(13) 0.0400(4) Uani 1 d H15 H 0.5642(24) 0.4156(35) 0.3038(15) 0.048 Uiso 1 d O16 O 0.38273(12) 0.2923(2) 0.21298(9) 0.0408(3) Uani 1 d C17 C 0.4505(2) 0.1405(3) 0.17813(13) 0.0402(4) Uani 1 d O18 O 0.57696(13) 0.1226(3) 0.20643(11) 0.0542(4) Uani 1 d C19 C 0.3497(2) 0.0071(3) 0.10188(14) 0.0420(4) Uani 1 d C20 C 0.3996(3) -0.1731(3) 0.0680(2) 0.0564(6) Uani 1 d H20 H 0.5011(26) -0.2082(44) 0.0987(18) 0.068 Uiso 1 d C21 C 0.3073(3) -0.2992(4) -0.0043(2) 0.0709(8) Uani 1 d H21 H 0.3407(28) -0.4160(52) -0.0314(22) 0.085 Uiso 1 d C22 C 0.1673(3) -0.2481(4) -0.0431(2) 0.0723(7) Uani 1 d H22 H 0.1013(31) -0.3359(51) -0.0911(22) 0.087 Uiso 1 d C23 C 0.1167(3) -0.0690(5) -0.0096(2) 0.0650(6) Uani 1 d H23 H 0.0126(30) -0.0380(46) -0.0380(20) 0.078 Uiso 1 d C24 C 0.2075(2) 0.0581(4) 0.0630(2) 0.0511(5) Uani 1 d H24 H 0.1723(24) 0.1883(42) 0.0826(18) 0.061 Uiso 1 d 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' 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 _geom_angle_publ_flag C7 C1 C11 108.00(14) yes C7 C1 C2 110.2(2) yes C11 C1 C2 110.67(15) yes C7 C1 C6 107.75(14) yes C11 C1 C6 110.07(14) yes C2 C1 C6 110.05(15) yes C3 C2 C1 111.6(2) yes C3 C2 H2A 113.1(12) ? C1 C2 H2A 107.4(13) ? C3 C2 H2B 113.2(13) ? C1 C2 H2B 108.4(14) ? H2A C2 H2B 102.6(19) ? C4 C3 C2 123.0(2) yes C4 C3 H3 120.1(13) ? C2 C3 H3 116.9(13) ? C3 C4 C5 122.1(2) yes C3 C4 H4 123.1(12) ? C5 C4 H4 114.8(12) ? C15 C5 C4 120.4(2) yes C15 C5 C6 121.23(15) yes C4 C5 C6 118.3(2) yes C5 C6 C1 112.28(14) yes C5 C6 H6A 108.9(11) ? C1 C6 H6A 110.0(11) ? C5 C6 H6B 109.3(11) ? C1 C6 H6B 105.9(12) ? H6A C6 H6B 110.4(17) ? O8 C7 O9 123.2(2) yes O8 C7 C1 125.0(2) yes O9 C7 C1 111.7(2) yes C7 O9 C10 116.4(2) yes O9 C10 H10A 109.6(18) ? O9 C10 H10B 111.6(18) ? H10A C10 H10B 101.7(27) ? O9 C10 H10C 109.6(19) ? H10A C10 H10C 117.1(26) ? H10B C10 H10C 106.9(28) ? O12 C11 O13 124.2(2) yes O12 C11 C1 125.6(2) yes O13 C11 C1 110.12(14) yes C11 O13 C14 116.20(15) yes O13 C14 H14A 102.9(15) ? O13 C14 H14B 109.7(15) ? H14A C14 H14B 108.1(23) ? O13 C14 H14C 110.7(16) ? H14A C14 H14C 112.5(21) ? H14B C14 H14C 112.5(24) ? C5 C15 O16 118.1(2) yes C5 C15 H15 127.9(13) ? O16 C15 H15 113.9(13) ? C17 O16 C15 119.27(14) yes O18 C17 O16 123.1(2) yes O18 C17 C19 125.9(2) yes O16 C17 C19 110.96(14) yes C24 C19 C20 119.9(2) yes C24 C19 C17 121.6(2) yes C20 C19 C17 118.5(2) yes C21 C20 C19 119.5(2) yes C21 C20 H20 122.3(16) ? C19 C20 H20 118.2(15) ? C22 C21 C20 120.6(2) yes C22 C21 H21 118.8(18) ? C20 C21 H21 120.4(18) ? C21 C22 C23 120.2(2) yes C21 C22 H22 121.8(18) ? C23 C22 H22 118.0(18) ? C24 C23 C22 119.9(2) yes C24 C23 H23 121.7(16) ? C22 C23 H23 118.3(16) ? C23 C24 C19 119.9(2) yes C23 C24 H24 119.3(14) ? C19 C24 H24 120.7(14) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C7 1.523(3) yes C1 C11 1.530(2) yes C1 C2 1.539(3) yes C1 C6 1.541(2) yes C2 C3 1.493(3) yes C2 H2A 1.01(2) ? C2 H2B 0.94(2) ? C3 C4 1.330(3) yes C3 H3 1.01(2) ? C4 C5 1.452(2) yes C4 H4 1.03(2) ? C5 C15 1.329(3) yes C5 C6 1.511(2) yes C6 H6A 1.01(2) ? C6 H6B 0.99(2) ? C7 O8 1.196(2) yes C7 O9 1.331(3) yes O9 C10 1.450(3) yes C10 H10A 1.05(4) ? C10 H10B 1.00(4) ? C10 H10C 0.99(4) ? C11 O12 1.198(2) yes C11 O13 1.338(2) yes O13 C14 1.453(2) yes C14 H14A 1.03(3) ? C14 H14B 1.01(3) ? C14 H14C 1.02(3) ? C15 O16 1.394(2) yes C15 H15 0.99(2) ? O16 C17 1.357(2) yes C17 O18 1.207(2) yes C17 C19 1.475(3) yes C19 C24 1.393(3) yes C19 C20 1.393(3) yes C20 C21 1.382(4) yes C20 H20 1.00(2) ? C21 C22 1.374(4) yes C21 H21 0.94(3) ? C22 C23 1.389(4) yes C22 H22 0.95(3) ? C23 C24 1.382(3) yes C23 H23 1.01(3) ? C24 H24 0.97(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 C7 C1 C2 C3 -168.95(14) C11 C1 C2 C3 71.6(2) C6 C1 C2 C3 -50.2(2) C1 C2 C3 C4 24.6(2) C2 C3 C4 C5 2.3(3) C3 C4 C5 C15 175.2(2) C3 C4 C5 C6 -1.3(3) C15 C5 C6 C1 157.0(2) C4 C5 C6 C1 -26.4(2) C7 C1 C6 C5 171.67(14) C11 C1 C6 C5 -70.8(2) C2 C1 C6 C5 51.5(2) C11 C1 C7 O8 141.1(2) C2 C1 C7 O8 20.1(2) C6 C1 C7 O8 -100.0(2) C11 C1 C7 O9 -39.8(2) C2 C1 C7 O9 -160.9(2) C6 C1 C7 O9 79.0(2) O8 C7 O9 C10 -0.6(3) C1 C7 O9 C10 -179.7(2) C7 C1 C11 O12 114.8(2) C2 C1 C11 O12 -124.5(2) C6 C1 C11 O12 -2.6(2) C7 C1 C11 O13 -64.5(2) C2 C1 C11 O13 56.3(2) C6 C1 C11 O13 178.14(14) O12 C11 O13 C14 -5.0(3) C1 C11 O13 C14 174.2(2) C4 C5 C15 O16 -176.04(15) C6 C5 C15 O16 0.4(3) C5 C15 O16 C17 174.3(2) C15 O16 C17 O18 1.9(3) C15 O16 C17 C19 -177.27(14) O18 C17 C19 C24 -170.4(2) O16 C17 C19 C24 8.8(2) O18 C17 C19 C20 9.1(3) O16 C17 C19 C20 -171.7(2) C24 C19 C20 C21 0.3(3) C17 C19 C20 C21 -179.3(2) C19 C20 C21 C22 0.2(4) C20 C21 C22 C23 -0.3(4) C21 C22 C23 C24 -0.1(4) C22 C23 C24 C19 0.5(4) C20 C19 C24 C23 -0.6(3) C17 C19 C24 C23 178.9(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30660353