#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:48:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201957 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/11/2011164.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_2011164 loop_ _publ_author_name 'Niwayama, Satomi' 'Holt, Elizabeth M.' _publ_section_title ; 6-Dimethoxymethyl-1-methoxycarbonylbicyclo[3.1.0]hex-2-ene-2-carboxylic acid ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e300 _journal_page_last e301 _journal_paper_doi 10.1107/S0108270100007757 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C12 H16 O6' _chemical_formula_sum 'C12 H16 O6' _chemical_formula_weight 256.25 _chemical_name_systematic ; 6-Dimethoxymethyl-1-methoxycarbonylbicyclo[3.1.0]hex-2-ene-2-carboxylic acid ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90.00 _cell_angle_beta 94.57(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.537(4) _cell_length_b 13.602(8) _cell_length_c 12.779(5) _cell_measurement_reflns_used 28 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.8 _cell_measurement_theta_min 5.6 _cell_volume 1305.9(12) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1991)' _computing_data_reduction XSCANS _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .944 _diffrn_measured_fraction_theta_max .944 _diffrn_measurement_device_type 'Syntex P4 four-circle' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .126 _diffrn_reflns_av_sigmaI/netI .0904 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 3773 _diffrn_reflns_theta_full 27.10 _diffrn_reflns_theta_max 27.10 _diffrn_reflns_theta_min 4.27 _diffrn_standards_decay_% none _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .105 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_description cube _exptl_crystal_F_000 544 _exptl_crystal_size_max .2 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .2 _refine_diff_density_max .11 _refine_diff_density_min -.08 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .992 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 2845 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .992 _refine_ls_R_factor_all .095 _refine_ls_R_factor_gt .067 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1511P)^2^+0.1243P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .233 _reflns_number_gt 1975 _reflns_number_total 2845 _reflns_threshold_expression I>2\s(I) _cod_data_source_file qa0312.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.1511P)^2^+0.1243P] where P = (Fo^2^+2Fc^2^)/3' 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^(Fo^2^)+(0.1511P)^2^+0.1243P] where P = (Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2011164 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 .7023(3) .72696(17) .15677(19) .0400(6) Uani d . 1 . . C C2 .6771(3) .66163(18) .06139(18) .0394(6) Uani d . 1 . . C C3 .5121(3) .6704(2) .0124(2) .0485(6) Uani d . 1 . . C H3A .4460 .6347 -.0535 .050 Uiso d R 1 . . H C4 .4010(3) .7463(2) .0634(2) .0543(7) Uani d . 1 . . C H4A .2921 .7181 .0837 .080 Uiso d R 1 . . H H4B .3733 .8005 .0169 .080 Uiso d R 1 . . H C5 .5208(3) .77995(18) .1608(2) .0483(7) Uani d . 1 . . C H5A .5221 .8484 .1790 .080 Uiso d R 1 . . H C6 .5815(3) .70636(17) .24505(19) .0421(6) Uani d . 1 . . C H6A .6222 .7353 .3112 .080 Uiso d R 1 . . H C7 .8776(3) .78091(17) .1753(2) .0472(6) Uani d . 1 . . C C8 1.0960(4) .8403(3) .3052(3) .0757(10) Uani d . 1 . . C H8A 1.1178 .8439 .3802 .080 Uiso d R 1 . . H H8B 1.1906 .8045 .2765 .080 Uiso d R 1 . . H H8C 1.0905 .9056 .2765 .080 Uiso d R 1 . . H C9 .8167(3) .59090(18) .03472(18) .0406(6) Uani d . 1 . . C C10 .4876(3) .60834(18) .25657(18) .0413(6) Uani d . 1 . . C H10A .4265 .5917 .1901 .080 Uiso d R 1 . . H C11 .7129(5) .5464(3) .3835(3) .0862(12) Uani d . 1 . . C H11A .7866 .4900 .3998 .080 Uiso d R 1 . . H H11B .7868 .6029 .3750 .080 Uiso d R 1 . . H H11C .6381 .5580 .4396 .080 Uiso d R 1 . . H C12 .2272(4) .5514(3) .3339(3) .0688(9) Uani d . 1 . . C H12A .1464 .5683 .3854 .080 Uiso d R 1 . . H H12B .1629 .5462 .2662 .080 Uiso d R 1 . . H H12C .2831 .4897 .3521 .080 Uiso d R 1 . . H O1 .9631(3) .81238(18) .10620(19) .0708(7) Uani d . 1 . . O O2 .9284(3) .79096(16) .27818(17) .0628(6) Uani d . 1 . . O O3 .9586(2) .58392(15) .08861(15) .0550(6) Uani d . 1 . . O O4 .7758(2) .53716(16) -.05012(15) .0590(6) Uani d . 1 . . O H4C .8645 .4866 -.0518 .050 Uiso d R 1 . . H O5 .6047(3) .52982(14) .28781(16) .0576(6) Uani d . 1 . . O O6 .3600(2) .62621(14) .32987(15) .0529(5) Uani d . 1 . . O 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 .0363(12) .0356(11) .0497(13) .0031(9) .0133(10) -.0003(9) C2 .0377(12) .0417(12) .0402(12) .0013(10) .0123(9) .0031(9) C3 .0431(13) .0599(15) .0435(13) .0041(12) .0087(10) .0068(11) C4 .0413(13) .0602(16) .0626(16) .0137(12) .0127(11) .0164(13) C5 .0400(13) .0375(12) .0700(17) .0049(10) .0206(11) -.0011(11) C6 .0432(13) .0387(12) .0460(13) -.0001(10) .0138(10) -.0081(10) C7 .0409(13) .0350(12) .0673(17) .0024(10) .0147(11) -.0059(11) C8 .0465(16) .079(2) .101(3) -.0055(16) -.0009(16) -.031(2) C9 .0398(12) .0439(12) .0392(11) .0002(10) .0104(9) -.0045(9) C10 .0435(12) .0428(13) .0389(12) -.0020(10) .0113(9) -.0023(9) C11 .062(2) .096(3) .098(3) .014(2) -.0106(19) .025(2) C12 .0543(16) .082(2) .071(2) -.0231(16) .0148(14) .0068(17) O1 .0568(13) .0771(15) .0816(15) -.0193(11) .0250(11) .0044(12) O2 .0467(11) .0706(14) .0714(13) -.0107(10) .0059(9) -.0171(11) O3 .0470(10) .0614(12) .0559(11) .0141(9) .0000(8) -.0175(9) O4 .0450(10) .0710(13) .0606(12) .0110(9) .0023(8) -.0241(10) O5 .0607(12) .0435(10) .0706(13) .0059(9) .0170(9) .0057(9) O6 .0454(10) .0592(11) .0564(11) -.0067(8) .0194(8) -.0044(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 C2 C1 C7 117.63(19) no C2 C1 C6 116.36(19) no C7 C1 C6 122.5(2) no C2 C1 C5 104.3(2) no C7 C1 C5 122.1(2) no C6 C1 C5 58.83(16) no C3 C2 C9 126.4(2) no C3 C2 C1 112.0(2) no C9 C2 C1 121.4(2) no C2 C3 C4 112.4(2) no C2 C3 H3A 133.1 no C4 C3 H3A 114.5 no C3 C4 C5 104.0(2) no C3 C4 H4A 111.1 no C5 C4 H4A 110.9 no C3 C4 H4B 111.1 no C5 C4 H4B 110.8 no H4A C4 H4B 108.9 no C6 C5 C1 59.93(15) no C6 C5 C4 120.0(2) no C1 C5 C4 107.1(2) no C6 C5 H5A 118.2 no C1 C5 H5A 117.8 no C4 C5 H5A 118.4 no C5 C6 C10 122.1(2) no C5 C6 C1 61.24(15) no C10 C6 C1 122.68(19) no C5 C6 H6A 114.3 no C10 C6 H6A 113.1 no C1 C6 H6A 114.0 no O1 C7 O2 123.3(2) no O1 C7 C1 124.5(3) no O2 C7 C1 112.2(2) no O2 C8 H8A 109.8 no O2 C8 H8B 109.5 no H8A C8 H8B 109.5 no O2 C8 H8C 109.1 no H8A C8 H8C 109.5 no H8B C8 H8C 109.5 no O3 C9 O4 123.5(2) no O3 C9 C2 121.5(2) no O4 C9 C2 115.0(2) no O6 C10 O5 112.48(19) no O6 C10 C6 105.02(19) no O5 C10 C6 113.7(2) no O6 C10 H10A 108.8 no O5 C10 H10A 108.3 no C6 C10 H10A 108.3 no O5 C11 H11A 109.8 no O5 C11 H11B 109.0 no H11A C11 H11B 109.5 no O5 C11 H11C 109.6 no H11A C11 H11C 109.5 no H11B C11 H11C 109.5 no O6 C12 H12A 109.8 no O6 C12 H12B 109.0 no H12A C12 H12B 109.5 no O6 C12 H12C 109.7 no H12A C12 H12C 109.5 no H12B C12 H12C 109.5 no C7 O2 C8 117.1(3) no C9 O4 H4C 107.2 no C10 O5 C11 114.8(2) no C10 O6 C12 114.5(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 . 1.508(3) yes C1 C7 . 1.513(4) yes C1 C6 . 1.531(3) yes C1 C5 . 1.551(3) yes C2 C3 . 1.353(4) yes C2 C9 . 1.485(3) yes C3 C4 . 1.509(4) yes C3 H3A . 1.0613 no C4 C5 . 1.548(4) yes C4 H4A . .9600 no C4 H4B . .9599 no C5 C6 . 1.514(4) yes C5 H5A . .9601 no C6 C10 . 1.522(3) yes C6 H6A . .9600 no C7 O1 . 1.212(3) yes C7 O2 . 1.347(3) yes C8 O2 . 1.448(4) yes C8 H8A . .9601 no C8 H8B . .9600 no C8 H8C . .9601 no C9 O3 . 1.228(3) yes C9 O4 . 1.323(3) yes C10 O6 . 1.416(3) yes C10 O5 . 1.422(3) yes C10 H10A . .9600 no C11 O5 . 1.433(4) yes C11 H11A . .9600 no C11 H11B . .9600 no C11 H11C . .9600 no C12 O6 . 1.431(3) yes C12 H12A . .9600 no C12 H12B . .9600 no C12 H12C . .9600 no O4 H4C . .9600 yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O4 H4c O3 3_765 .96 1.74 2.668(3) 162 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 C3 C2 C9 O4 5.0(4) no C2 C1 C7 O1 34.3(4) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 355729