#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/27/2012753.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_2012753 loop_ _publ_author_name 'Esther Garc\'ia G.' 'Mendoza G., Virgilio' 'Guzm\'an-B., Jos\'e Agust\'in' 'Graniel, Luis Angel Maldonado' 'Hern\'andez-Ortega, Sim\'on' _publ_section_title ; 2-[3-Furyl(hydroxy)methyl]-2,3-dimethylcyclohexanone ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o336 _journal_page_last o338 _journal_paper_doi 10.1107/S0108270102007527 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C13 H18 O3' _chemical_formula_moiety 'C13 H18 O3' _chemical_formula_sum 'C13 H18 O3' _chemical_formula_weight 222.27 _chemical_melting_point .36E-305 _chemical_name_common FV-LAMAL _chemical_name_systematic ; 2-[(3-Furyl)(hydroxy)methyl]-2,3-dimethylcyclohexanone ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.962(3) _cell_length_b 8.249(4) _cell_length_c 18.931(9) _cell_measurement_reflns_used 512 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.09 _cell_measurement_theta_min 2.69 _cell_volume 1243.4(10) _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT-Plus (Bruker, 1999)' _computing_molecular_graphics 'SHELXTL (Bruker, 2000)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker CCD area-detector' _diffrn_measurement_method '\f and \w' _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 0.1486 _diffrn_reflns_av_sigmaI/netI 0.0667 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 11179 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.15 _diffrn_standards_decay_% <2 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 480 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.149 _refine_diff_density_min -0.122 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 1667 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.988 _refine_ls_R_factor_all 0.0845 _refine_ls_R_factor_gt 0.0524 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.004 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0271P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0891 _refine_ls_wR_factor_ref 0.0983 _reflns_number_gt 1045 _reflns_number_total 1667 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fr1367.cif _cod_data_source_block I _cod_original_cell_volume 1243.3(10) _cod_database_code 2012753 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 O1 -0.0547(2) 0.7757(3) 0.10759(12) 0.0733(7) Uani d . 1 . . O O2 0.2303(3) 0.6215(3) 0.00156(11) 0.0610(6) Uani d . 1 . . O H2 0.287(4) 0.644(3) -0.0319(15) 0.061(11) Uiso d . 1 . . H C1 0.0978(4) 0.7891(3) 0.11498(16) 0.0543(7) Uani d . 1 . . C C2 0.2099(3) 0.6414(3) 0.12763(14) 0.0496(7) Uani d . 1 . . C C3 0.3079(4) 0.6697(4) 0.19776(16) 0.0627(8) Uani d . 1 . . C H3 0.3942 0.5852 0.2008 0.075 Uiso calc R 1 . . H C4 0.3997(4) 0.8345(4) 0.1983(2) 0.0823(11) Uani d . 1 . . C H4A 0.4549 0.8490 0.2435 0.099 Uiso calc R 1 . . H H4B 0.4855 0.8345 0.1619 0.099 Uiso calc R 1 . . H C5 0.2803(5) 0.9755(4) 0.1856(2) 0.0874(12) Uani d . 1 . . C H5A 0.3439 1.0756 0.1829 0.105 Uiso calc R 1 . . H H5B 0.2028 0.9841 0.2250 0.105 Uiso calc R 1 . . H C6 0.1809(4) 0.9516(3) 0.1167(2) 0.0716(10) Uani d . 1 . . C H6A 0.0963 1.0357 0.1127 0.086 Uiso calc R 1 . . H H6B 0.2564 0.9616 0.0767 0.086 Uiso calc R 1 . . H C7 0.3326(3) 0.6299(3) 0.06395(15) 0.0511(7) Uani d . 1 . . C H7 0.3971 0.7309 0.0620 0.061 Uiso calc R 1 . . H C8 0.1032(3) 0.4871(3) 0.13147(19) 0.0644(9) Uani d . 1 . . C H8A 0.0682 0.4568 0.0848 0.077 Uiso calc R 1 . . H H8B 0.0060 0.5068 0.1603 0.077 Uiso calc R 1 . . H H8C 0.1684 0.4010 0.1518 0.077 Uiso calc R 1 . . H C9 0.1950(4) 0.6520(4) 0.26324(16) 0.0965(12) Uani d . 1 . . C H9A 0.2521 0.6949 0.3038 0.116 Uiso calc R 1 . . H H9B 0.1701 0.5395 0.2709 0.116 Uiso calc R 1 . . H H9C 0.0923 0.7107 0.2559 0.116 Uiso calc R 1 . . H O10 0.6957(2) 0.3527(3) 0.07977(12) 0.0755(7) Uani d . 1 . . O C11 0.6202(3) 0.5009(4) 0.08266(17) 0.0624(8) Uani d . 1 . . C H11 0.6759 0.5968 0.0936 0.075 Uiso calc R 1 . . H C12 0.4551(3) 0.4917(3) 0.06766(15) 0.0504(7) Uani d . 1 . . C C13 0.4257(4) 0.3236(3) 0.05373(18) 0.0645(8) Uani d . 1 . . C H13 0.3237 0.2765 0.0414 0.077 Uiso calc R 1 . . H C14 0.5724(4) 0.2472(4) 0.06168(18) 0.0691(9) Uani d . 1 . . C H14 0.5878 0.1364 0.0556 0.083 Uiso calc R 1 . . H 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 O1 0.0525(12) 0.0876(15) 0.0797(15) 0.0032(11) -0.0070(12) 0.0100(12) O2 0.0610(14) 0.0709(14) 0.0509(12) -0.0047(11) -0.0005(13) 0.0113(11) C1 0.0532(17) 0.0607(19) 0.0491(18) 0.0001(14) -0.0011(16) 0.0009(14) C2 0.0513(16) 0.0477(16) 0.0496(16) -0.0043(13) -0.0005(15) 0.0009(13) C3 0.066(2) 0.0674(19) 0.0550(18) 0.0067(16) -0.0111(17) -0.0015(16) C4 0.079(2) 0.085(2) 0.084(2) -0.006(2) -0.021(2) -0.025(2) C5 0.096(3) 0.061(2) 0.105(3) -0.009(2) 0.001(3) -0.020(2) C6 0.075(2) 0.0487(19) 0.091(3) 0.0036(15) -0.002(2) 0.0025(17) C7 0.0528(16) 0.0461(15) 0.0543(17) -0.0121(13) -0.0063(15) 0.0041(15) C8 0.0647(19) 0.0604(18) 0.068(2) -0.0102(16) 0.0073(17) 0.0102(17) C9 0.127(3) 0.110(3) 0.053(2) -0.005(3) -0.006(2) -0.002(2) O10 0.0615(13) 0.0736(15) 0.0915(17) 0.0112(12) 0.0043(13) 0.0010(13) C11 0.0557(17) 0.0525(17) 0.079(2) -0.0034(16) 0.0073(17) 0.0020(17) C12 0.0513(16) 0.0490(15) 0.0508(16) -0.0049(15) 0.0024(16) -0.0032(15) C13 0.0597(19) 0.0564(17) 0.077(2) -0.0062(15) -0.0081(18) -0.0052(17) C14 0.083(2) 0.0523(16) 0.072(2) 0.0048(19) 0.007(2) -0.0026(17) 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 O2 H2 109(2) ? O1 C1 C6 121.4(3) yes O1 C1 C2 121.6(3) yes C6 C1 C2 116.9(2) yes C1 C2 C8 110.2(2) yes C1 C2 C7 107.1(2) yes C8 C2 C7 109.5(2) ? C1 C2 C3 107.9(2) ? C8 C2 C3 111.2(2) ? C7 C2 C3 110.8(2) ? C9 C3 C4 110.8(3) ? C9 C3 C2 112.3(2) ? C4 C3 C2 112.0(3) ? C9 C3 H3 107.1 ? C4 C3 H3 107.1 ? C2 C3 H3 107.1 ? C5 C4 C3 112.1(2) ? C5 C4 H4A 109.2 ? C3 C4 H4A 109.2 ? C5 C4 H4B 109.2 ? C3 C4 H4B 109.2 ? H4A C4 H4B 107.9 ? C4 C5 C6 110.9(3) ? C4 C5 H5A 109.4 ? C6 C5 H5A 109.5 ? C4 C5 H5B 109.5 ? C6 C5 H5B 109.4 ? H5A C5 H5B 108.0 ? C1 C6 C5 111.2(3) ? C1 C6 H6A 109.4 ? C5 C6 H6A 109.4 ? C1 C6 H6B 109.4 ? C5 C6 H6B 109.4 ? H6A C6 H6B 108.0 ? O2 C7 C12 111.7(2) ? O2 C7 C2 106.5(2) yes C12 C7 C2 114.7(2) ? O2 C7 H7 107.9 ? C12 C7 H7 107.9 ? C2 C7 H7 107.9 ? C2 C8 H8A 109.5 ? C2 C8 H8B 109.5 ? H8A C8 H8B 109.5 ? C2 C8 H8C 109.5 ? H8A C8 H8C 109.5 ? H8B C8 H8C 109.5 ? C3 C9 H9A 109.5 ? C3 C9 H9B 109.5 ? H9A C9 H9B 109.5 ? C3 C9 H9C 109.5 ? H9A C9 H9C 109.5 ? H9B C9 H9C 109.5 ? C14 O10 C11 105.4(2) yes C12 C11 O10 111.8(3) yes C12 C11 H11 124.1 ? O10 C11 H11 124.1 ? C11 C12 C13 104.7(3) yes C11 C12 C7 126.9(2) ? C13 C12 C7 128.4(2) ? C14 C13 C12 107.1(3) yes C14 C13 H13 126.5 ? C12 C13 H13 126.5 ? C13 C14 O10 111.1(3) yes C13 C14 H14 124.5 ? O10 C14 H14 124.5 ? 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 O1 C1 . 1.227(3) yes O2 C7 . 1.436(3) yes O2 H2 . 0.80(3) ? C1 C6 . 1.496(4) ? C1 C2 . 1.529(4) yes C2 C8 . 1.532(3) yes C2 C7 . 1.554(4) yes C2 C3 . 1.558(4) yes C3 C9 . 1.538(4) ? C3 C4 . 1.544(4) ? C3 H3 . 0.9800 ? C4 C5 . 1.521(4) ? C4 H4A . 0.9700 ? C4 H4B . 0.9700 ? C5 C6 . 1.538(5) ? C5 H5A . 0.9700 ? C5 H5B . 0.9700 ? C6 H6A . 0.9700 ? C6 H6B . 0.9700 ? C7 C12 . 1.502(4) ? C7 H7 . 0.9800 ? C8 H8A . 0.9600 ? C8 H8B . 0.9600 ? C8 H8C . 0.9600 ? C9 H9A . 0.9600 ? C9 H9B . 0.9600 ? C9 H9C . 0.9600 ? O10 C14 . 1.356(3) yes O10 C11 . 1.364(3) yes C11 C12 . 1.347(3) yes C11 H11 . 0.9300 ? C12 C13 . 1.430(4) yes C13 C14 . 1.335(4) yes C13 H13 . 0.9300 ? C14 H14 . 0.9300 ? 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 O2 H2 O1 4_565 0.80(3) 2.02(3) 2.814(3) 172(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 _geom_torsion_publ_flag O1 C1 C2 C8 -1.8(4) yes C6 C1 C2 C8 174.3(3) ? O1 C1 C2 C7 117.3(3) yes C6 C1 C2 C7 -66.6(3) ? O1 C1 C2 C3 -123.4(3) ? C6 C1 C2 C3 52.8(3) ? C1 C2 C3 C9 73.1(3) ? C8 C2 C3 C9 -47.9(3) ? C7 C2 C3 C9 -170.0(3) ? C1 C2 C3 C4 -52.3(3) ? C8 C2 C3 C4 -173.3(2) ? C7 C2 C3 C4 64.6(3) ? C9 C3 C4 C5 -69.8(4) ? C2 C3 C4 C5 56.5(4) ? C3 C4 C5 C6 -55.0(4) ? O1 C1 C6 C5 122.6(3) ? C2 C1 C6 C5 -53.5(4) ? C4 C5 C6 C1 52.1(4) ? C1 C2 C7 O2 -56.5(3) yes C8 C2 C7 O2 63.0(3) yes C3 C2 C7 O2 -173.9(2) ? C1 C2 C7 C12 179.3(2) ? C8 C2 C7 C12 -61.2(3) ? C3 C2 C7 C12 61.9(3) ? C14 O10 C11 C12 0.5(3) ? O10 C11 C12 C13 -0.5(4) ? O10 C11 C12 C7 -178.4(3) ? O2 C7 C12 C11 133.0(3) ? C2 C7 C12 C11 -105.6(3) ? O2 C7 C12 C13 -44.4(4) ? C2 C7 C12 C13 77.0(4) ? C11 C12 C13 C14 0.3(4) ? C7 C12 C13 C14 178.2(3) ? C12 C13 C14 O10 0.0(4) ? C11 O10 C14 C13 -0.3(4) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21181806 2 PubChem 139058583