#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/06/2200647.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_2200647 loop_ _publ_author_name 'Arrieta, Antonio F.' 'Arvid Mostad' _publ_section_title ; Orthorhombic form of 6-phenylhex-5-ene-2,4-dione ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1198 _journal_page_last o1199 _journal_paper_doi 10.1107/S1600536801018669 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C12 H12 O2' _chemical_formula_sum 'C12 H12 O2' _chemical_formula_weight 188.22 _chemical_name_common Cinnamonylaceton _chemical_name_systematic ; 6-phenyl-hex-5-ene-2,3-dione ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 8.9118(18) _cell_length_b 9.4953(19) _cell_length_c 23.628(5) _cell_measurement_reflns_used 1024 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 56.57 _cell_measurement_theta_min 4.88 _cell_volume 1999.4(7) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'SHELXTL (Bruker, 1998)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 123(2) _diffrn_detector_area_resol_mean 8 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART 1000' _diffrn_measurement_method '\w scans' _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 .022 _diffrn_reflns_av_sigmaI/netI .0099 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 22303 _diffrn_reflns_theta_full 28.29 _diffrn_reflns_theta_max 28.29 _diffrn_reflns_theta_min 1.72 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .084 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 800 _exptl_crystal_size_max .5 _exptl_crystal_size_mid .5 _exptl_crystal_size_min .5 _refine_diff_density_max .27 _refine_diff_density_min -.20 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.12 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 175 _refine_ls_number_reflns 2484 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.12 _refine_ls_R_factor_all .051 _refine_ls_R_factor_gt .041 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0786P)^2^+0.3676P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .137 _reflns_number_gt 2117 _reflns_number_total 2484 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6070.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M Pbca _cod_database_code 2200647 _cod_database_fobs_code 2200647 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' '-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 O2 .15763(11) .41407(11) 1.02601(4) .0451(3) Uani d . 1 . . O C5 .35327(14) .41508(13) .95832(5) .0329(3) Uani d . 1 . . C O1 .17570(12) .26796(11) 1.11420(4) .0448(3) Uani d . 1 . . O C7 .32508(14) .55492(12) .86880(5) .0306(3) Uani d . 1 . . C C3 .36973(14) .27630(13) 1.04732(5) .0338(3) Uani d . 1 . . C C12 .23888(15) .65810(14) .84172(5) .0356(3) Uani d . 1 . . C C6 .27959(14) .50658(13) .92530(5) .0323(3) Uani d . 1 . . C C4 .29333(14) .36701(12) 1.01243(5) .0310(3) Uani d . 1 . . C C2 .30470(15) .22893(12) 1.09945(5) .0337(3) Uani d . 1 . . C C11 .27489(15) .70378(15) .78736(5) .0377(3) Uani d . 1 . . C C10 .39557(15) .64545(14) .75881(5) .0368(3) Uani d . 1 . . C C8 .44917(15) .49877(13) .83985(5) .0341(3) Uani d . 1 . . C C1 .39099(19) .13243(15) 1.13747(6) .0419(3) Uani d . 1 . . C C9 .48290(15) .54290(14) .78535(5) .0371(3) Uani d . 1 . . C H6 .1842(18) .5443(17) .9381(7) .041(4) Uiso d . 1 . . H H9 .5711(19) .4992(17) .7657(7) .043(4) Uiso d . 1 . . H H10 .4183(18) .6761(17) .7205(7) .044(4) Uiso d . 1 . . H H8 .5093(19) .4269(19) .8564(7) .048(4) Uiso d . 1 . . H H3 .4672(19) .2447(17) 1.0373(7) .045(4) Uiso d . 1 . . H H11 .2108(18) .7779(18) .7699(7) .043(4) Uiso d . 1 . . H H5 .4498(18) .3775(17) .9478(7) .042(4) Uiso d . 1 . . H H12 .1520(19) .6994(19) .8607(7) .046(4) Uiso d . 1 . . H H20 .135(3) .370(2) 1.0631(11) .088(7) Uiso d . 1 . . H H1B .326(3) .058(3) 1.1518(10) .084(7) Uiso d . 1 . . H H1C .480(3) .095(2) 1.1227(10) .087(7) Uiso d . 1 . . H H1A .422(3) .182(3) 1.1705(13) .110(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 O2 .0438(6) .0507(6) .0409(5) .0088(4) .0110(4) .0086(4) C5 .0355(6) .0370(6) .0263(5) -.0023(5) .0014(4) -.0010(4) O1 .0500(6) .0454(6) .0390(5) -.0015(4) .0139(4) .0056(4) C7 .0360(6) .0296(5) .0261(5) -.0035(4) -.0026(4) -.0009(4) C3 .0363(6) .0384(6) .0269(6) -.0022(5) .0012(5) .0003(4) C12 .0370(6) .0380(6) .0317(6) .0026(5) -.0022(5) -.0011(5) C6 .0367(6) .0327(6) .0273(5) -.0022(5) .0008(4) -.0018(4) C4 .0350(6) .0310(6) .0270(5) -.0047(4) .0009(4) -.0035(4) C2 .0446(6) .0292(6) .0272(5) -.0086(5) .0010(5) -.0036(4) C11 .0411(7) .0400(7) .0320(6) .0003(5) -.0080(5) .0035(5) C10 .0447(7) .0390(6) .0267(6) -.0066(5) -.0026(5) .0009(4) C8 .0376(6) .0309(6) .0340(6) .0004(5) .0007(5) .0028(4) C1 .0566(8) .0410(7) .0280(6) -.0043(6) -.0024(6) .0019(5) C9 .0413(7) .0358(6) .0341(6) -.0015(5) .0051(5) -.0001(5) 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 C4 O2 H20 105.0(14) n C6 C5 C4 122.26(12) y C6 C5 H5 121.9(9) n C4 C5 H5 115.9(9) n C12 C7 C8 118.35(11) n C12 C7 C6 118.86(11) y C8 C7 C6 122.75(11) y C4 C3 C2 120.81(12) y C4 C3 H3 120.2(10) n C2 C3 H3 119.0(10) n C11 C12 C7 120.86(12) n C11 C12 H12 118.7(10) n C7 C12 H12 120.5(10) n C5 C6 C7 126.63(12) y C5 C6 H6 119.1(9) n C7 C6 H6 114.2(9) n O2 C4 C3 121.16(11) y O2 C4 C5 116.09(11) y C3 C4 C5 122.74(12) y O1 C2 C3 121.02(12) y O1 C2 C1 118.96(11) y C3 C2 C1 120.02(12) y C10 C11 C12 120.22(12) n C10 C11 H11 121.7(9) n C12 C11 H11 118.1(9) n C11 C10 C9 119.55(12) n C11 C10 H10 119.7(10) n C9 C10 H10 120.7(10) n C9 C8 C7 120.52(12) n C9 C8 H8 118.4(10) n C7 C8 H8 121.0(10) n C2 C1 H1B 110.5(15) n C2 C1 H1C 116.3(15) n H1B C1 H1C 111(2) n C2 C1 H1A 109.5(17) n H1B C1 H1A 104(2) n H1C C1 H1A 104(2) n C8 C9 C10 120.47(12) n C8 C9 H9 118.3(9) n C10 C9 H9 121.2(9) n 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 O2 C4 . 1.3286(16) y O2 H20 . .99(3) n C5 C6 . 1.3397(17) y C5 C4 . 1.4589(16) y C5 H5 . .964(16) n O1 C2 . 1.2571(17) y C7 C12 . 1.3998(17) n C7 C8 . 1.4054(18) n C7 C6 . 1.4687(16) y C3 C4 . 1.3729(17) y C3 C2 . 1.4337(16) y C3 H3 . .949(17) n C12 C11 . 1.3931(18) n C12 H12 . .976(17) n C6 H6 . .971(16) n C2 C1 . 1.4960(19) y C11 C10 . 1.3851(19) n C11 H11 . .996(17) n C10 C9 . 1.3955(19) n C10 H10 . .972(17) n C8 C9 . 1.3871(18) n C8 H8 . .951(18) n C1 H1B . .97(3) n C1 H1C . .94(2) n C1 H1A . .95(3) n C9 H9 . 1.002(17) n 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 H20 O1 . .99(3) 1.59(3) 2.5085(14) 152(2) C8 H8 O1 4_557 .951(18) 2.471(18) 3.4159(17) 172.0(14) 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 C8 C7 C12 C11 .17(19) n C6 C7 C12 C11 -177.86(12) n C4 C5 C6 C7 -175.97(11) y C12 C7 C6 C5 -176.01(12) y C8 C7 C6 C5 6.1(2) y C2 C3 C4 O2 .35(19) y C2 C3 C4 C5 -178.34(11) y C6 C5 C4 O2 3.09(18) y C6 C5 C4 C3 -178.16(12) y C4 C3 C2 O1 .79(19) y C4 C3 C2 C1 -178.74(11) y C7 C12 C11 C10 1.2(2) n C12 C11 C10 C9 -1.4(2) n C12 C7 C8 C9 -1.30(18) n C6 C7 C8 C9 176.64(11) n C7 C8 C9 C10 1.07(19) n C11 C10 C9 C8 .3(2) n loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654630 2 PubChem 5385594