#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/16/2011653.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_2011653 loop_ _publ_author_name 'Arrieta, Antonio F' 'Haglund, Kjersti Ann' 'Mostad, Arvid' _publ_section_title ; Conjugation and hydrogen bonding in a curcumin analogue ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e594 _journal_page_last e595 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C16 H14 O3' _chemical_formula_sum 'C16 H14 O3' _chemical_formula_weight 254.27 _chemical_melting_point 363 _chemical_name_systematic 5-(methylfur-2-yl)-1-phenylpent-4-ene-1,3-dione _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 90.00 _cell_angle_beta 96.10(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.0907(14) _cell_length_b 8.0793(16) _cell_length_c 23.070(5) _cell_measurement_reflns_used 5595 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 26.40 _cell_measurement_theta_min 2.67 _cell_volume 1314.1(5) _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction SAINT _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 8 _diffrn_measured_fraction_theta_full .995 _diffrn_measured_fraction_theta_max .995 _diffrn_measurement_device_type 'Simens SMART diffractometer' _diffrn_measurement_method 'w scan' _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 .0399 _diffrn_reflns_av_sigmaI/netI .0291 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 13412 _diffrn_reflns_theta_max 26.40 _diffrn_reflns_theta_min 2.67 _exptl_absorpt_coefficient_mu .088 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'transparent plates' _exptl_crystal_F_000 536 _exptl_crystal_size_max .3 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .2 _refine_diff_density_max .18 _refine_diff_density_min -.18 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 228 _refine_ls_number_reflns 2684 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all .060 _refine_ls_R_factor_gt .040 _refine_ls_shift/su_max .005 _refine_ls_shift/su_mean .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0350P)^2^+0.4300P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .098 _reflns_number_gt 2094 _reflns_number_total 2684 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file qa0450.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '363K' was changed to '363' - the value should be numeric and without a unit designator. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '363K' was changed to '363' - the value should be numeric and without a unit designator. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1314.2(5) _cod_database_code 2011653 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 O1 1.40232(15) .44540(14) .14142(4) .0418(3) Uani d . 1 . . O O2 1.10575(16) .49405(14) .07803(4) .0384(3) Uani d . 1 . . O O3 .51191(14) .84032(12) .07622(4) .0325(3) Uani d . 1 . . O C1 1.4325(2) .6696(2) .27951(6) .0353(4) Uani d . 1 . . C C2 1.5615(2) .6906(2) .32879(7) .0375(4) Uani d . 1 . . C C3 1.7399(2) .6205(2) .33153(7) .0394(4) Uani d . 1 . . C C4 1.7920(3) .5301(2) .28470(8) .0450(4) Uani d . 1 . . C C5 1.6644(2) .5095(2) .23531(7) .0404(4) Uani d . 1 . . C C6 1.4827(2) .57759(18) .23230(6) .0316(3) Uani d . 1 . . C C7 1.3503(2) .54835(19) .17850(6) .0326(3) Uani d . 1 . . C C8 1.1726(2) .62980(19) .16814(6) .0332(3) Uani d . 1 . . C C9 1.0554(2) .60045(18) .11708(6) .0319(3) Uani d . 1 . . C C10 .8739(2) .68233(19) .10420(7) .0334(3) Uani d . 1 . . C C11 .7644(2) .65873(19) .05353(6) .0316(3) Uani d . 1 . . C C12 .5835(2) .73296(18) .03742(6) .0309(3) Uani d . 1 . . C C13 .4577(2) .7199(2) -.01133(7) .0355(4) Uani d . 1 . . C C14 .3020(2) .8232(2) -.00273(7) .0403(4) Uani d . 1 . . C C15 .3394(2) .89405(19) .05026(7) .0357(4) Uani d . 1 . . C C16 .2361(3) 1.0122(2) .08449(9) .0455(4) Uani d . 1 . . C H1 1.307(2) .718(2) .2792(7) .044(5) Uiso d . 1 . . H H8 1.131(2) .707(2) .1959(7) .038(4) Uiso d . 1 . . H H10 .835(2) .753(2) .1332(7) .034(4) Uiso d . 1 . . H H13 .474(2) .656(2) -.0446(7) .036(4) Uiso d . 1 . . H H11 .809(2) .585(2) .0243(7) .035(4) Uiso d . 1 . . H H2 1.525(2) .751(2) .3626(7) .040(4) Uiso d . 1 . . H H3 1.834(2) .634(2) .3665(7) .040(4) Uiso d . 1 . . H H5 1.698(2) .450(2) .2035(8) .053(5) Uiso d . 1 . . H H4 1.917(3) .482(2) .2858(8) .055(5) Uiso d . 1 . . H H16A .205(3) .967(3) .1206(10) .080(7) Uiso d . 1 . . H H14 .183(3) .837(2) -.0284(8) .053(5) Uiso d . 1 . . H H16B .312(3) 1.114(3) .0962(10) .087(8) Uiso d . 1 . . H H16C .124(4) 1.056(3) .0608(12) .110(9) Uiso d . 1 . . H HO2 1.233(4) .454(3) .0931(11) .100(8) Uiso d . 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 .0429(6) .0475(7) .0350(6) .0133(5) .0031(5) -.0090(5) O2 .0409(6) .0432(7) .0313(6) .0093(5) .0043(5) -.0049(5) O3 .0323(6) .0322(6) .0331(5) .0026(4) .0040(4) -.0025(4) C1 .0385(9) .0360(8) .0327(8) .0021(7) .0096(6) .0006(7) C2 .0471(9) .0371(9) .0293(8) -.0044(7) .0088(7) -.0010(7) C3 .0464(10) .0368(9) .0337(8) -.0047(7) -.0019(7) .0029(7) C4 .0413(9) .0437(10) .0486(10) .0080(8) -.0024(7) -.0015(8) C5 .0432(9) .0398(9) .0382(9) .0086(7) .0040(7) -.0053(7) C6 .0381(8) .0285(8) .0289(7) .0011(6) .0062(6) .0025(6) C7 .0372(8) .0312(8) .0304(7) .0015(6) .0090(6) .0013(6) C8 .0370(8) .0340(8) .0296(8) .0057(7) .0074(6) -.0023(6) C9 .0372(8) .0304(8) .0292(7) .0019(6) .0095(6) .0015(6) C10 .0363(8) .0337(8) .0311(8) .0035(6) .0082(6) -.0010(7) C11 .0345(8) .0291(8) .0322(8) .0006(6) .0076(6) .0006(6) C12 .0354(8) .0272(7) .0312(8) .0002(6) .0093(6) -.0006(6) C13 .0385(9) .0375(9) .0308(8) -.0008(7) .0044(6) -.0023(7) C14 .0342(9) .0472(10) .0388(9) .0034(7) .0006(7) -.0008(7) C15 .0312(8) .0358(8) .0406(9) .0021(6) .0062(6) .0021(7) C16 .0425(10) .0459(11) .0495(11) .0093(8) .0112(8) -.0036(9) 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 C7 . 1.2754(18) yes O2 C9 . 1.3217(17) yes O2 HO2 . .99(3) no O3 C15 . 1.3738(18) yes O3 C12 . 1.3812(17) yes C1 C2 . 1.392(2) yes C1 C6 . 1.396(2) yes C1 H1 . .968(17) no C2 C3 . 1.381(2) yes C2 H2 . .978(17) no C3 C4 . 1.386(2) yes C3 H3 . .996(16) no C4 C5 . 1.388(2) yes C4 H4 . .965(19) no C5 C6 . 1.395(2) yes C5 H5 . .930(19) no C6 C7 . 1.494(2) yes C7 C8 . 1.419(2) yes C8 C9 . 1.388(2) yes C8 H8 . .961(17) no C9 C10 . 1.450(2) yes C10 C11 . 1.346(2) yes C10 H10 . .942(16) no C11 C12 . 1.429(2) yes C11 H11 . .977(16) no C12 C13 . 1.363(2) yes C13 C14 . 1.414(2) yes C13 H13 . .942(16) no C14 C15 . 1.351(2) yes C14 H14 . .984(18) no C15 C16 . 1.481(2) yes C16 H16A . .96(2) no C16 H16B . 1.00(3) no C16 H16C . .98(3) no 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 C9 O2 HO2 106.0(15) no C15 O3 C12 106.71(11) yes C2 C1 C6 120.13(15) no C2 C1 H1 118.6(10) no C6 C1 H1 121.2(10) no C3 C2 C1 120.45(15) no C3 C2 H2 119.1(9) no C1 C2 H2 120.4(10) no C2 C3 C4 119.93(15) no C2 C3 H3 121.5(9) no C4 C3 H3 118.6(9) no C5 C4 C3 119.91(16) no C5 C4 H4 119.2(11) no C3 C4 H4 120.9(11) no C4 C5 C6 120.77(15) no C4 C5 H5 120.7(11) no C6 C5 H5 118.6(11) no C5 C6 C1 118.81(14) no C5 C6 C7 118.34(13) yes C1 C6 C7 122.86(14) yes O1 C7 C8 120.30(14) yes O1 C7 C6 117.34(13) yes C8 C7 C6 122.36(13) yes C9 C8 C7 120.30(14) yes C9 C8 H8 118.5(9) no C7 C8 H8 121.2(9) no O2 C9 C8 120.60(14) yes O2 C9 C10 117.08(13) yes C8 C9 C10 122.32(14) yes C11 C10 C9 122.06(14) yes C11 C10 H10 121.2(9) no C9 C10 H10 116.8(9) no C10 C11 C12 125.81(14) yes C10 C11 H11 119.2(9) no C12 C11 H11 115.0(9) no C13 C12 O3 109.27(13) yes C13 C12 C11 132.27(14) yes O3 C12 C11 118.46(13) yes C12 C13 C14 106.89(14) yes C12 C13 H13 125.9(10) no C14 C13 H13 127.2(10) no C15 C14 C13 107.23(15) yes C15 C14 H14 124.6(11) no C13 C14 H14 128.1(11) no C14 C15 O3 109.91(13) yes C14 C15 C16 134.05(16) yes O3 C15 C16 116.04(14) yes C15 C16 H16A 112.9(14) no C15 C16 H16B 112.8(13) no H16A C16 H16B 104.1(19) no C15 C16 H16C 110.7(16) no H16A C16 H16C 112(2) no H16B C16 H16C 104(2) no 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 C6 C1 C2 C3 -.2(2) no C1 C2 C3 C4 .8(2) no C2 C3 C4 C5 -.4(3) no C3 C4 C5 C6 -.5(3) no C4 C5 C6 C1 1.1(2) no C4 C5 C6 C7 -178.78(15) no C2 C1 C6 C5 -.8(2) no C2 C1 C6 C7 179.13(14) no C5 C6 C7 O1 8.7(2) no C1 C6 C7 O1 -171.25(14) no C5 C6 C7 C8 -171.57(15) no C1 C6 C7 C8 8.5(2) no O1 C7 C8 C9 -1.2(2) no C6 C7 C8 C9 179.06(13) no C7 C8 C9 O2 1.4(2) no C7 C8 C9 C10 -179.14(14) no O2 C9 C10 C11 -3.4(2) no C8 C9 C10 C11 177.13(14) no C9 C10 C11 C12 179.43(14) no C15 O3 C12 C13 -.30(15) no C15 O3 C12 C11 179.66(13) no C10 C11 C12 C13 -179.35(16) no C10 C11 C12 O3 .7(2) no O3 C12 C13 C14 .16(17) no C11 C12 C13 C14 -179.80(16) no C12 C13 C14 C15 .05(19) no C13 C14 C15 O3 -.24(18) no C13 C14 C15 C16 179.9(8) no C12 O3 C15 C14 .33(16) no C12 O3 C15 C16 -179.85(14) no _cod_database_fobs_code 2011653