#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:03:30 +0200 (mar 06 de oct de 2020) $
#$Revision: 258168 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/81/1558184.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_1558184
loop_
_publ_author_name
'RESENDE, Pamela C. S.'
'COURI, Mara R. C.'
'MIGUEL, Fábio B.'
'CUIN, Alexandre'
_publ_section_title
;
 Analytical, Spectroscopic and Crystallographic Characterization of
 3-[(2E)-3-Phenylprop-2-en-1-ylidene]pentane-2,4-dione
;
_journal_issue                   0
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              15
_journal_page_last               16
_journal_paper_doi               10.2116/xraystruct.36.15
_journal_volume                  36
_journal_year                    2020
_chemical_formula_moiety         'C14 H14 O2'
_chemical_formula_sum            'C14 H14 O2'
_chemical_formula_weight         214.25
_chemical_name_common            'Compound X'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-10-25T18:00:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 106.525(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.7006(4)
_cell_length_b                   10.0271(5)
_cell_length_c                   20.1044(10)
_cell_measurement_reflns_used    10638
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.546
_cell_volume                     2454.55(19)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows(Farrugia, 2012)'
_computing_publication_material  'ORTEP-3 for Windows(Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.801199E-1
_diffrn_orient_matrix_UB_12      -0.216614E-1
_diffrn_orient_matrix_UB_13      0.127141E-1
_diffrn_orient_matrix_UB_21      -0.144714E-1
_diffrn_orient_matrix_UB_22      -0.678834E-1
_diffrn_orient_matrix_UB_23      -0.379697E-1
_diffrn_orient_matrix_UB_31      0.107938E-1
_diffrn_orient_matrix_UB_32      0.697757E-1
_diffrn_orient_matrix_UB_33      -0.32993E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1136
_diffrn_reflns_av_unetI/netI     0.0767
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24070
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.63
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.16
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.163
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1494
_refine_ls_R_factor_gt           0.0831
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0958P)²+1.8484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2238
_refine_ls_wR_factor_ref         0.2565
_reflns_number_gt                2517
_reflns_number_total             4711
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            36_15_1.txt
_cod_data_source_block           s93
_cod_depositor_comments          'Adding full bibliography for 1558184.cif.'
_cod_original_sg_symbol_Hall     -P2yab
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               1558184
_publcif_datablock.id            {b53be10c-262c-43f3-b232-8edc12746352}
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O11 O 0.1300(3) 0.4370(3) -0.06726(16) 0.0947(10) Uani 1 1 d . . .
O12 O 0.3107(3) 0.2599(3) -0.14794(17) 0.0928(10) Uani 1 1 d . . .
C11 C 0.1968(3) 0.2200(4) -0.07749(19) 0.0618(10) Uani 1 1 d . . .
C12 C 0.1778(3) 0.1506(4) -0.0246(2) 0.0658(10) Uani 1 1 d . . .
H12 H 0.2185 0.0728 -0.0119 0.079 Uiso 1 1 calc R . .
C13 C 0.1024(3) 0.1819(4) 0.0146(2) 0.0672(10) Uani 1 1 d . . .
H13 H 0.0606 0.2593 0.0044 0.081 Uiso 1 1 calc R . .
C14 C 0.0910(3) 0.1018(4) 0.0655(2) 0.0669(10) Uani 1 1 d . . .
H14 H 0.1333 0.0246 0.0728 0.08 Uiso 1 1 calc R . .
C15 C 0.0213(3) 0.1200(4) 0.11093(19) 0.0596(9) Uani 1 1 d . . .
C16 C -0.0403(4) 0.2351(4) 0.1111(2) 0.0799(12) Uani 1 1 d . . .
H16 H -0.04 0.3029 0.0796 0.096 Uiso 1 1 calc R . .
C17 C -0.1013(4) 0.2496(5) 0.1570(3) 0.0886(14) Uani 1 1 d . . .
H17 H -0.1429 0.3263 0.1562 0.106 Uiso 1 1 calc R . .
C18 C -0.1009(4) 0.1497(5) 0.2047(2) 0.0819(12) Uani 1 1 d . . .
H18 H -0.141 0.1604 0.2364 0.098 Uiso 1 1 calc R . .
C19 C -0.0421(3) 0.0359(4) 0.2053(2) 0.0734(11) Uani 1 1 d . . .
H19 H -0.0434 -0.0318 0.2368 0.088 Uiso 1 1 calc R . .
C110 C 0.0194(3) 0.0214(4) 0.1591(2) 0.0644(10) Uani 1 1 d . . .
H110 H 0.0603 -0.056 0.1602 0.077 Uiso 1 1 calc R . .
C111 C 0.1341(3) 0.3435(4) -0.1053(2) 0.0665(10) Uani 1 1 d . . .
C112 C 0.0708(4) 0.3464(5) -0.1797(2) 0.0849(13) Uani 1 1 d . . .
H11A H 0.0029 0.2992 -0.186 0.127 Uiso 1 1 calc R . .
H11B H 0.1129 0.3048 -0.2067 0.127 Uiso 1 1 calc R . .
H11C H 0.0557 0.4373 -0.1944 0.127 Uiso 1 1 calc R . .
C113 C 0.2827(3) 0.1800(4) -0.1094(2) 0.0704(11) Uani 1 1 d . . .
C114 C 0.3356(4) 0.0459(5) -0.0956(3) 0.0919(14) Uani 1 1 d . . .
H11D H 0.378 0.03 -0.1275 0.138 Uiso 1 1 calc R . .
H11E H 0.28 -0.0215 -0.1016 0.138 Uiso 1 1 calc R . .
H11F H 0.3829 0.0428 -0.0489 0.138 Uiso 1 1 calc R . .
O21 O 0.4606(3) 0.2705(4) 0.65313(18) 0.0995(11) Uani 1 1 d . . .
O22 O 0.2088(3) 0.0818(3) 0.57425(16) 0.0921(10) Uani 1 1 d . . .
C21 C 0.2811(3) 0.3010(4) 0.58264(19) 0.0612(9) Uani 1 1 d . . .
C22 C 0.2108(3) 0.3672(4) 0.5302(2) 0.0683(10) Uani 1 1 d . . .
H22 H 0.237 0.446 0.5163 0.082 Uiso 1 1 calc R . .
C23 C 0.1006(3) 0.3310(4) 0.4932(2) 0.0694(11) Uani 1 1 d . . .
H23 H 0.0695 0.2559 0.5071 0.083 Uiso 1 1 calc R . .
C24 C 0.0411(3) 0.4024(4) 0.4391(2) 0.0712(11) Uani 1 1 d . . .
H24 H 0.0745 0.4793 0.4289 0.085 Uiso 1 1 calc R . .
C25 C -0.0688(3) 0.3753(4) 0.39427(19) 0.0632(10) Uani 1 1 d . . .
C26 C -0.1141(3) 0.4574(4) 0.3385(2) 0.0735(11) Uani 1 1 d . . .
H26 H -0.0747 0.531 0.3308 0.088 Uiso 1 1 calc R . .
C27 C -0.2170(3) 0.4324(5) 0.2938(2) 0.0799(12) Uani 1 1 d . . .
H27 H -0.2461 0.4895 0.2566 0.096 Uiso 1 1 calc R . .
C28 C -0.2759(3) 0.3245(5) 0.3040(2) 0.0796(12) Uani 1 1 d . . .
H28 H -0.3447 0.3071 0.2735 0.095 Uiso 1 1 calc R . .
C29 C -0.2332(3) 0.2419(5) 0.3594(3) 0.0818(12) Uani 1 1 d . . .
H29 H -0.2739 0.1692 0.3669 0.098 Uiso 1 1 calc R . .
C210 C -0.1308(3) 0.2653(5) 0.4041(2) 0.0771(12) Uani 1 1 d . . .
H210 H -0.1024 0.2077 0.4411 0.093 Uiso 1 1 calc R . .
C211 C 0.3954(3) 0.3444(4) 0.6126(2) 0.0714(11) Uani 1 1 d . . .
C212 C 0.4344(3) 0.4756(5) 0.5937(2) 0.0832(13) Uani 1 1 d . . .
H21A H 0.3982 0.5463 0.6107 0.125 Uiso 1 1 calc R . .
H21B H 0.4178 0.4821 0.5441 0.125 Uiso 1 1 calc R . .
H21C H 0.5123 0.4827 0.614 0.125 Uiso 1 1 calc R . .
C213 C 0.2468(3) 0.1747(4) 0.6118(2) 0.0675(10) Uani 1 1 d . . .
C214 C 0.2548(4) 0.1718(5) 0.6867(2) 0.0961(15) Uani 1 1 d . . .
H21D H 0.189 0.2084 0.6938 0.144 Uiso 1 1 calc R . .
H21E H 0.3169 0.2237 0.7118 0.144 Uiso 1 1 calc R . .
H21F H 0.2637 0.0813 0.703 0.144 Uiso 1 1 calc R . .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C11 C113 121.6(4) . . ?
C12 C11 C111 121.8(4) . . ?
C113 C11 C111 116.5(3) . . ?
C11 C12 C13 128.0(4) . . ?
C11 C12 H12 116 . . ?
C13 C12 H12 116 . . ?
C14 C13 C12 121.4(4) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 128.5(4) . . ?
C13 C14 H14 115.8 . . ?
C15 C14 H14 115.8 . . ?
C110 C15 C16 117.8(3) . . ?
C110 C15 C14 118.9(3) . . ?
C16 C15 C14 123.2(4) . . ?
C17 C16 C15 120.9(4) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 119.8(4) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.5(4) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C110 119.7(4) . . ?
C18 C19 H19 120.2 . . ?
C110 C19 H19 120.2 . . ?
C19 C110 C15 121.3(4) . . ?
C19 C110 H110 119.4 . . ?
C15 C110 H110 119.4 . . ?
O11 C111 C112 120.6(4) . . ?
O11 C111 C11 121.1(4) . . ?
C112 C111 C11 118.2(4) . . ?
C111 C112 H11A 109.5 . . ?
C111 C112 H11B 109.5 . . ?
H11A C112 H11B 109.5 . . ?
C111 C112 H11C 109.5 . . ?
H11A C112 H11C 109.5 . . ?
H11B C112 H11C 109.5 . . ?
O12 C113 C11 118.6(4) . . ?
O12 C113 C114 120.3(4) . . ?
C11 C113 C114 121.0(4) . . ?
C113 C114 H11D 109.5 . . ?
C113 C114 H11E 109.5 . . ?
H11D C114 H11E 109.5 . . ?
C113 C114 H11F 109.5 . . ?
H11D C114 H11F 109.5 . . ?
H11E C114 H11F 109.5 . . ?
C22 C21 C211 122.1(4) . . ?
C22 C21 C213 121.1(4) . . ?
C211 C21 C213 116.7(3) . . ?
C21 C22 C23 127.8(4) . . ?
C21 C22 H22 116.1 . . ?
C23 C22 H22 116.1 . . ?
C24 C23 C22 121.8(4) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C23 C24 C25 128.5(4) . . ?
C23 C24 H24 115.8 . . ?
C25 C24 H24 115.8 . . ?
C26 C25 C210 117.6(4) . . ?
C26 C25 C24 119.8(4) . . ?
C210 C25 C24 122.5(4) . . ?
C25 C26 C27 121.3(4) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 H26 119.3 . . ?
C28 C27 C26 120.3(4) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C29 119.6(4) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C28 C29 C210 120.7(4) . . ?
C28 C29 H29 119.7 . . ?
C210 C29 H29 119.7 . . ?
C29 C210 C25 120.5(4) . . ?
C29 C210 H210 119.8 . . ?
C25 C210 H210 119.8 . . ?
O21 C211 C21 119.5(4) . . ?
O21 C211 C212 119.4(4) . . ?
C21 C211 C212 121.1(4) . . ?
C211 C212 H21A 109.5 . . ?
C211 C212 H21B 109.5 . . ?
H21A C212 H21B 109.5 . . ?
C211 C212 H21C 109.5 . . ?
H21A C212 H21C 109.5 . . ?
H21B C212 H21C 109.5 . . ?
O22 C213 C214 121.3(4) . . ?
O22 C213 C21 120.8(4) . . ?
C214 C213 C21 117.8(4) . . ?
C213 C214 H21D 109.5 . . ?
C213 C214 H21E 109.5 . . ?
H21D C214 H21E 109.5 . . ?
C213 C214 H21F 109.5 . . ?
H21D C214 H21F 109.5 . . ?
H21E C214 H21F 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C111 1.220(5) . ?
O12 C113 1.235(5) . ?
C11 C12 1.350(5) . ?
C11 C113 1.469(5) . ?
C11 C111 1.492(6) . ?
C12 C13 1.436(5) . ?
C12 H12 0.93 . ?
C13 C14 1.341(5) . ?
C13 H13 0.93 . ?
C14 C15 1.452(5) . ?
C14 H14 0.93 . ?
C15 C110 1.390(5) . ?
C15 C16 1.395(5) . ?
C16 C17 1.372(6) . ?
C16 H16 0.93 . ?
C17 C18 1.385(6) . ?
C17 H17 0.93 . ?
C18 C19 1.362(6) . ?
C18 H18 0.93 . ?
C19 C110 1.382(5) . ?
C19 H19 0.93 . ?
C110 H110 0.93 . ?
C111 C112 1.483(6) . ?
C112 H11A 0.96 . ?
C112 H11B 0.96 . ?
C112 H11C 0.96 . ?
C113 C114 1.494(6) . ?
C114 H11D 0.96 . ?
C114 H11E 0.96 . ?
C114 H11F 0.96 . ?
O21 C211 1.231(5) . ?
O22 C213 1.210(5) . ?
C21 C22 1.347(5) . ?
C21 C211 1.471(5) . ?
C21 C213 1.511(5) . ?
C22 C23 1.432(5) . ?
C22 H22 0.93 . ?
C23 C24 1.342(5) . ?
C23 H23 0.93 . ?
C24 C25 1.456(5) . ?
C24 H24 0.93 . ?
C25 C26 1.378(5) . ?
C25 C210 1.402(6) . ?
C26 C27 1.382(6) . ?
C26 H26 0.93 . ?
C27 C28 1.364(6) . ?
C27 H27 0.93 . ?
C28 C29 1.371(6) . ?
C28 H28 0.93 . ?
C29 C210 1.374(6) . ?
C29 H29 0.93 . ?
C210 H210 0.93 . ?
C211 C212 1.492(6) . ?
C212 H21A 0.96 . ?
C212 H21B 0.96 . ?
C212 H21C 0.96 . ?
C213 C214 1.480(6) . ?
C214 H21D 0.96 . ?
C214 H21E 0.96 . ?
C214 H21F 0.96 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C113 C11 C12 C13 175.5(4) . . . . ?
C111 C11 C12 C13 -2.6(6) . . . . ?
C11 C12 C13 C14 179.0(4) . . . . ?
C12 C13 C14 C15 178.3(4) . . . . ?
C13 C14 C15 C110 177.8(4) . . . . ?
C13 C14 C15 C16 -5.4(7) . . . . ?
C110 C15 C16 C17 -0.4(6) . . . . ?
C14 C15 C16 C17 -177.3(4) . . . . ?
C15 C16 C17 C18 0.9(7) . . . . ?
C16 C17 C18 C19 -1.4(7) . . . . ?
C17 C18 C19 C110 1.4(7) . . . . ?
C18 C19 C110 C15 -1.0(6) . . . . ?
C16 C15 C110 C19 0.5(6) . . . . ?
C14 C15 C110 C19 177.5(4) . . . . ?
C12 C11 C111 O11 54.9(5) . . . . ?
C113 C11 C111 O11 -123.4(4) . . . . ?
C12 C11 C111 C112 -121.3(4) . . . . ?
C113 C11 C111 C112 60.5(5) . . . . ?
C12 C11 C113 O12 -166.3(4) . . . . ?
C111 C11 C113 O12 11.9(5) . . . . ?
C12 C11 C113 C114 13.6(6) . . . . ?
C111 C11 C113 C114 -168.2(4) . . . . ?
C211 C21 C22 C23 175.2(4) . . . . ?
C213 C21 C22 C23 -2.4(6) . . . . ?
C21 C22 C23 C24 -176.2(4) . . . . ?
C22 C23 C24 C25 176.5(4) . . . . ?
C23 C24 C25 C26 -176.4(4) . . . . ?
C23 C24 C25 C210 1.7(7) . . . . ?
C210 C25 C26 C27 0.0(6) . . . . ?
C24 C25 C26 C27 178.2(4) . . . . ?
C25 C26 C27 C28 -0.4(7) . . . . ?
C26 C27 C28 C29 0.9(7) . . . . ?
C27 C28 C29 C210 -1.2(7) . . . . ?
C28 C29 C210 C25 0.9(7) . . . . ?
C26 C25 C210 C29 -0.3(6) . . . . ?
C24 C25 C210 C29 -178.4(4) . . . . ?
C22 C21 C211 O21 -169.4(4) . . . . ?
C213 C21 C211 O21 8.3(6) . . . . ?
C22 C21 C211 C212 9.5(6) . . . . ?
C213 C21 C211 C212 -172.8(4) . . . . ?
C22 C21 C213 O22 54.1(5) . . . . ?
C211 C21 C213 O22 -123.6(4) . . . . ?
C22 C21 C213 C214 -122.2(4) . . . . ?
C211 C21 C213 C214 60.0(5) . . . . ?
