#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/41/2014151.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_2014151
loop_
_publ_author_name
'Mague, Joel T.'
'Alworth, William L.'
'Payton, Florastina L.'
_publ_section_title
;
 Curcumin and derivatives
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o608
_journal_page_last               o610
_journal_paper_doi               10.1107/S0108270104015434
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C25 H24 O8'
_chemical_formula_moiety         'C25 H24 O8'
_chemical_formula_sum            'C25 H24 O8'
_chemical_formula_weight         452.44
_chemical_name_common            Bis(acetoxy)curcumin
_chemical_name_systematic
;
4-[7-(4-Acetoxy-3-methoxyphenyl)-5-hydroxy-3-oxohepta-1,4,6-trienyl]-2-
methoxyphenyl acetate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.092(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.841(2)
_cell_length_b                   7.7460(10)
_cell_length_c                   16.326(3)
_cell_measurement_reflns_used    4191
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.33
_cell_volume                     1106.9(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2004)'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9606
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         1.26
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_correction_T_min  0.9480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         2794
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0576P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                2222
_reflns_number_total             2794
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fr1497.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2014151
_cod_database_fobs_code          2014151
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 1.7999(3) 0.6181(4) 0.95585(17) 0.0589(7) Uani d . 1 . . O
O2 1.6779(2) 0.8235(3) 0.87438(12) 0.0344(5) Uani d . 1 . . O
O3 1.5224(2) 0.7804(3) 1.00457(12) 0.0383(5) Uani d . 1 . . O
O4 0.8249(2) 0.2979(3) 0.80510(12) 0.0404(6) Uani d . 1 . . O
H4O 0.7384 0.2615 0.7916 0.061 Uiso d PR 0.37(5) . . H
O5 0.5708(2) 0.2440(3) 0.71494(12) 0.0369(5) Uani d . 1 . . O
H5O 0.6430 0.2221 0.7527 0.055 Uiso calc PR 0.63(5) . . H
O6 -0.1248(2) 0.2651(4) 0.39979(13) 0.0574(8) Uani d . 1 . . O
O7 -0.0244(2) 0.4085(3) 0.26887(12) 0.0354(5) Uani d . 1 . . O
O8 -0.1160(3) 0.6337(4) 0.33415(14) 0.0532(7) Uani d . 1 . . O
C1 1.9343(3) 0.8779(6) 0.9272(2) 0.0449(9) Uani d . 1 . . C
H1A 2.0010 0.8620 0.9799 0.067 Uiso calc R 1 . . H
H1B 1.8967 0.9970 0.9232 0.067 Uiso calc R 1 . . H
H1C 1.9919 0.8543 0.8814 0.067 Uiso calc R 1 . . H
C2 1.8025(3) 0.7570(5) 0.92287(19) 0.0356(7) Uani d . 1 . . C
C3 1.5414(3) 0.7294(4) 0.86546(17) 0.0294(6) Uani d . 1 . . C
C4 1.4580(3) 0.7121(4) 0.93153(16) 0.0277(6) Uani d . 1 . . C
C5 1.3174(3) 0.6293(4) 0.91803(17) 0.0290(6) Uani d . 1 . . C
H5 1.2608 0.6143 0.9628 0.035 Uiso calc R 1 . . H
C6 1.2577(3) 0.5674(4) 0.83963(17) 0.0277(6) Uani d . 1 . . C
C7 1.3427(3) 0.5858(4) 0.77447(17) 0.0328(7) Uani d . 1 . . C
H7 1.3038 0.5435 0.7210 0.039 Uiso calc R 1 . . H
C8 1.4852(3) 0.6668(4) 0.78802(17) 0.0324(7) Uani d . 1 . . C
H8 1.5437 0.6787 0.7438 0.039 Uiso calc R 1 . . H
C9 1.4364(3) 0.7679(5) 1.07217(17) 0.0376(7) Uani d . 1 . . C
H9A 1.3368 0.8236 1.0571 0.056 Uiso calc R 1 . . H
H9B 1.4920 0.8255 1.1207 0.056 Uiso calc R 1 . . H
H9C 1.4213 0.6460 1.0850 0.056 Uiso calc R 1 . . H
C10 1.1054(3) 0.4876(4) 0.82861(18) 0.0312(7) Uani d . 1 . . C
H10 1.0692 0.4427 0.8764 0.037 Uiso calc R 1 . . H
C11 1.0145(3) 0.4735(4) 0.75673(18) 0.0330(7) Uani d . 1 . . C
H11 1.0493 0.5197 0.7088 0.040 Uiso calc R 1 . . H
C12 0.8636(3) 0.3908(5) 0.74705(17) 0.0334(7) Uani d . 1 . . C
C13 0.7635(3) 0.4175(5) 0.67279(18) 0.0345(7) Uani d . 1 . . C
H13 0.7950 0.4897 0.6313 0.041 Uiso calc R 1 . . H
C14 0.6206(3) 0.3411(4) 0.65902(18) 0.0317(7) Uani d . 1 . . C
C15 0.5217(3) 0.3657(5) 0.58061(18) 0.0351(7) Uani d . 1 . . C
H15 0.5560 0.4410 0.5412 0.042 Uiso calc R 1 . . H
C16 0.3870(3) 0.2898(5) 0.56064(17) 0.0345(7) Uani d . 1 . . C
H16 0.3531 0.2153 0.6006 0.041 Uiso calc R 1 . . H
C17 0.2855(3) 0.3117(5) 0.48149(18) 0.0349(7) Uani d . 1 . . C
C18 0.1306(3) 0.2681(5) 0.47871(17) 0.0393(8) Uani d . 1 . . C
H18 0.0963 0.2163 0.5255 0.047 Uiso calc R 1 . . H
C19 0.0275(3) 0.3002(5) 0.40827(17) 0.0371(7) Uani d . 1 . . C
C20 0.0796(3) 0.3764(5) 0.34048(17) 0.0344(7) Uani d . 1 . . C
C21 0.2311(3) 0.4133(5) 0.34066(18) 0.0348(7) Uani d . 1 . . C
H21 0.2652 0.4605 0.2928 0.042 Uiso calc R 1 . . H
C22 0.3350(3) 0.3813(5) 0.41129(17) 0.0341(7) Uani d . 1 . . C
H22 0.4401 0.4072 0.4116 0.041 Uiso calc R 1 . . H
C23 -0.1892(3) 0.2297(7) 0.4687(2) 0.0578(11) Uani d . 1 . . C
H23A -0.1479 0.1209 0.4930 0.087 Uiso calc R 1 . . H
H23B -0.3001 0.2195 0.4539 0.087 Uiso calc R 1 . . H
H23C -0.1659 0.3232 0.5089 0.087 Uiso calc R 1 . . H
C24 -0.1231(3) 0.5426(5) 0.27468(18) 0.0358(7) Uani d . 1 . . C
C25 -0.2348(4) 0.5595(5) 0.19709(18) 0.0399(8) Uani d . 1 . . C
H25A -0.3214 0.6306 0.2081 0.060 Uiso calc R 1 . . H
H25B -0.2715 0.4447 0.1784 0.060 Uiso calc R 1 . . H
H25C -0.1845 0.6142 0.1540 0.060 Uiso calc R 1 . . H
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
C2 O2 C3 118.6(2) ?
C4 O3 C9 116.8(2) ?
C12 O4 H4O 109.4 ?
C14 O5 H5O 109.5 ?
C23 O6 C19 118.7(2) ?
C24 O7 C20 115.2(2) ?
C2 C1 H1A 109.5 ?
C2 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C2 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
O1 C2 O2 122.1(3) ?
O1 C2 C1 127.2(3) ?
O2 C2 C1 110.7(3) ?
C8 C3 C4 120.9(2) ?
C8 C3 O2 118.2(2) ?
C4 C3 O2 120.7(2) ?
O3 C4 C5 125.2(2) ?
O3 C4 C3 116.1(2) ?
C5 C4 C3 118.7(2) ?
C4 C5 C6 121.2(3) ?
C4 C5 H5 119.4 ?
C6 C5 H5 119.4 ?
C7 C6 C5 119.3(3) ?
C7 C6 C10 122.2(3) ?
C5 C6 C10 118.5(3) ?
C6 C7 C8 119.8(3) ?
C6 C7 H7 120.1 ?
C8 C7 H7 120.1 ?
C3 C8 C7 120.2(3) ?
C3 C8 H8 119.9 ?
C7 C8 H8 119.9 ?
O3 C9 H9A 109.5 ?
O3 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
O3 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C11 C10 C6 124.9(3) ?
C11 C10 H10 117.6 ?
C6 C10 H10 117.6 ?
C10 C11 C12 123.9(3) ?
C10 C11 H11 118.0 ?
C12 C11 H11 118.0 ?
O4 C12 C13 121.4(3) y
O4 C12 C11 120.1(2) y
C13 C12 C11 118.6(3) y
C14 C13 C12 121.6(3) y
C14 C13 H13 119.2 ?
C12 C13 H13 119.2 ?
O5 C14 C13 121.5(3) y
O5 C14 C15 118.0(2) y
C13 C14 C15 120.5(3) y
C16 C15 C14 124.4(3) ?
C16 C15 H15 117.8 ?
C14 C15 H15 117.8 ?
C15 C16 C17 125.3(3) ?
C15 C16 H16 117.3 ?
C17 C16 H16 117.3 ?
C22 C17 C18 119.0(3) ?
C22 C17 C16 122.9(2) ?
C18 C17 C16 118.1(3) ?
C19 C18 C17 120.6(3) ?
C19 C18 H18 119.7 ?
C17 C18 H18 119.7 ?
O6 C19 C18 125.1(3) ?
O6 C19 C20 116.0(2) ?
C18 C19 C20 118.9(2) ?
C21 C20 C19 121.4(3) ?
C21 C20 O7 119.4(3) ?
C19 C20 O7 119.2(2) ?
C20 C21 C22 119.7(3) ?
C20 C21 H21 120.1 ?
C22 C21 H21 120.1 ?
C21 C22 C17 120.3(3) ?
C21 C22 H22 119.9 ?
C17 C22 H22 119.9 ?
O6 C23 H23A 109.5 ?
O6 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
O6 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
O8 C24 O7 122.9(3) ?
O8 C24 C25 126.1(3) ?
O7 C24 C25 111.0(3) ?
C24 C25 H25A 109.5 ?
C24 C25 H25B 109.5 ?
H25A C25 H25B 109.5 ?
C24 C25 H25C 109.5 ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
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 C2 . 1.204(4) ?
O2 C2 . 1.364(4) ?
O2 C3 . 1.399(3) ?
O3 C4 . 1.354(3) ?
O3 C9 . 1.429(3) ?
O4 C12 . 1.274(4) y
O4 H4O . 0.8160 ?
O5 C14 . 1.306(3) y
O5 H5O . 0.8400 ?
O6 C23 . 1.359(4) ?
O6 C19 . 1.361(3) ?
O7 C24 . 1.368(4) ?
O7 C20 . 1.404(3) ?
O8 C24 . 1.195(4) ?
C1 C2 . 1.489(5) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C3 C8 . 1.380(4) ?
C3 C4 . 1.396(4) ?
C4 C5 . 1.388(4) ?
C5 C6 . 1.399(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.393(4) ?
C6 C10 . 1.469(4) ?
C7 C8 . 1.397(4) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 C11 . 1.330(4) y
C10 H10 . 0.9500 ?
C11 C12 . 1.469(4) y
C11 H11 . 0.9500 ?
C12 C13 . 1.412(4) y
C13 C14 . 1.384(4) y
C13 H13 . 0.9500 ?
C14 C15 . 1.457(4) y
C15 C16 . 1.327(4) y
C15 H15 . 0.9500 ?
C16 C17 . 1.475(4) ?
C16 H16 . 0.9500 ?
C17 C22 . 1.392(4) ?
C17 C18 . 1.405(4) ?
C18 C19 . 1.386(4) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.389(4) ?
C20 C21 . 1.369(4) ?
C21 C22 . 1.392(4) ?
C21 H21 . 0.9500 ?
C22 H22 . 0.9500 ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 0.9800 ?
C24 C25 . 1.498(4) ?
C25 H25A . 0.9800 ?
C25 H25B . 0.9800 ?
C25 H25C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O4 H4O O5 0.82 1.80 2.541(3) 149
O5 H5O O4 0.84 1.81 2.541(3) 145
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 O2 C2 O1 2.4(4) ?
C3 O2 C2 C1 -177.9(2) ?
C2 O2 C3 C8 -115.3(3) ?
C2 O2 C3 C4 70.1(4) y
C9 O3 C4 C5 -1.2(4) ?
C9 O3 C4 C3 178.3(3) ?
C8 C3 C4 O3 -179.0(3) ?
O2 C3 C4 O3 -4.5(4) ?
C8 C3 C4 C5 0.5(4) ?
O2 C3 C4 C5 175.0(3) ?
O3 C4 C5 C6 177.9(3) ?
C3 C4 C5 C6 -1.5(4) ?
C4 C5 C6 C7 1.5(4) ?
C4 C5 C6 C10 -177.4(3) ?
C5 C6 C7 C8 -0.6(4) ?
C10 C6 C7 C8 178.4(3) ?
C4 C3 C8 C7 0.5(5) ?
O2 C3 C8 C7 -174.2(3) ?
C6 C7 C8 C3 -0.4(5) ?
C7 C6 C10 C11 -21.5(5) y
C5 C6 C10 C11 157.5(3) ?
C6 C10 C11 C12 179.0(3) y
C10 C11 C12 O4 -13.9(5) ?
C10 C11 C12 C13 165.7(3) y
O4 C12 C13 C14 -1.5(5) ?
C11 C12 C13 C14 178.9(3) ?
C12 C13 C14 O5 1.6(5) ?
C12 C13 C14 C15 -177.7(3) y
O5 C14 C15 C16 -3.1(5) ?
C13 C14 C15 C16 176.2(3) y
C14 C15 C16 C17 -179.5(3) y
C15 C16 C17 C22 16.0(6) y
C15 C16 C17 C18 -160.7(4) ?
C22 C17 C18 C19 -2.5(5) ?
C16 C17 C18 C19 174.3(3) ?
C23 O6 C19 C18 14.4(6) ?
C23 O6 C19 C20 -164.5(4) ?
C17 C18 C19 O6 -179.1(4) ?
C17 C18 C19 C20 -0.1(5) ?
O6 C19 C20 C21 -178.1(3) ?
C18 C19 C20 C21 2.9(5) ?
O6 C19 C20 O7 -1.2(5) ?
C18 C19 C20 O7 179.8(3) ?
C24 O7 C20 C21 -109.7(4) ?
C24 O7 C20 C19 73.3(4) y
C19 C20 C21 C22 -2.9(5) ?
O7 C20 C21 C22 -179.8(3) ?
C20 C21 C22 C17 0.2(5) ?
C18 C17 C22 C21 2.5(5) ?
C16 C17 C22 C21 -174.2(3) ?
C20 O7 C24 O8 4.7(4) ?
C20 O7 C24 C25 -176.7(3) ?
