#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/41/2014134.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_2014134
loop_
_publ_author_name
'Girija, C. R.'
'Begum, Noor Shahina'
'Syed, Akheel Ahmed'
'Thiruvenkatam, Vijay'
_publ_section_title
;
 Hydrogen-bonding and C---H···π interactions in
 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione
 (tetrahydrocurcumin)
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o611
_journal_page_last               o613
_journal_paper_doi               10.1107/S0108270104015549
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C21 H24 O6'
_chemical_formula_moiety         'C21 H24 O6'
_chemical_formula_sum            'C21 H24 O6'
_chemical_formula_weight         372.40
_chemical_melting_point          .371E-305
_chemical_name_common            Tetrahydrocurcumin
_chemical_name_systematic
;
1,7-Bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                117.065(3)
_cell_angle_beta                 100.394(10)
_cell_angle_gamma                94.856(3)
_cell_formula_units_Z            2
_cell_length_a                   7.981(3)
_cell_length_b                   11.388(3)
_cell_length_c                   12.497(3)
_cell_measurement_reflns_used    400
_cell_measurement_temperature    293
_cell_measurement_theta_max      20.9
_cell_measurement_theta_min      2.6
_cell_volume                     976.6(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0.3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10125
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_correction_T_min  0.8932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            off-white
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.357
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0943P)²+0.1978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.1709
_reflns_number_gt                3244
_reflns_number_total             3933
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1755.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        976.7(5)
_cod_database_code               2014134
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-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
O3 0.39116(19) 0.10484(12) 0.15185(11) 0.0695(4) Uani d . 1 . . O
H3 0.4156 0.1174 0.2233 0.083 Uiso calc PR 0.54(4) . . H
O5 0.5533(2) 0.20794(16) 0.37143(12) 0.0866(5) Uani d . 1 . . O
H5 0.5018 0.1472 0.3024 0.104 Uiso calc PR 0.46(4) . . H
O13 0.5788(2) 0.16537(16) -0.39619(13) 0.0808(4) Uani d . 1 . . O
O14 0.30604(19) 0.25057(16) -0.47282(12) 0.0746(4) Uani d . 1 . . O
H14 0.3868 0.2246 -0.5040 0.089 Uiso calc R 1 . . H
O73 1.0931(2) 0.91069(13) 0.84928(12) 0.0770(4) Uani d . 1 . . O
O74 1.17662(19) 0.85429(13) 1.03595(12) 0.0748(4) Uani d . 1 . . O
H74 1.2083 0.9216 1.0309 0.090 Uiso calc R 1 . . H
C1 0.4644(3) 0.32948(19) 0.01914(16) 0.0664(5) Uani d . 1 . . C
H1A 0.5892 0.3570 0.0517 0.080 Uiso calc R 1 . . H
H1B 0.4112 0.4013 0.0705 0.080 Uiso calc R 1 . . H
C2 0.4046(3) 0.20418(18) 0.02555(15) 0.0629(5) Uani d . 1 . . C
H2A 0.2787 0.1840 0.0016 0.075 Uiso calc R 1 . . H
H2B 0.4446 0.1303 -0.0355 0.075 Uiso calc R 1 . . H
C3 0.4626(2) 0.20850(16) 0.14839(14) 0.0519(4) Uani d . 1 . . C
C4 0.5807(2) 0.31142(17) 0.25120(15) 0.0586(4) Uani d . 1 . . C
H4 0.6312 0.3850 0.2464 0.070 Uiso calc R 1 . . H
C5 0.6245(2) 0.30593(19) 0.36145(15) 0.0638(5) Uani d . 1 . . C
C6 0.7564(3) 0.4152(3) 0.47335(18) 0.0936(8) Uani d . 1 . . C
H6A 0.8648 0.3833 0.4796 0.112 Uiso calc R 1 . . H
H6B 0.7772 0.4921 0.4600 0.112 Uiso calc R 1 . . H
C7 0.7092(3) 0.4592(2) 0.58977(19) 0.0894(7) Uani d . 1 . . C
H7A 0.6813 0.3809 0.6000 0.107 Uiso calc R 1 . . H
H7B 0.6040 0.4953 0.5843 0.107 Uiso calc R 1 . . H
C11 0.4176(2) 0.30701(18) -0.11265(16) 0.0606(4) Uani d . 1 . . C
C12 0.5203(2) 0.24394(18) -0.19180(16) 0.0604(4) Uani d . 1 . . C
H12 0.6155 0.2148 -0.1636 0.072 Uiso calc R 1 . . H
C13 0.4842(2) 0.22343(17) -0.31199(16) 0.0573(4) Uani d . 1 . . C
C14 0.3407(2) 0.26661(18) -0.35512(16) 0.0585(4) Uani d . 1 . . C
C15 0.2363(3) 0.3266(2) -0.2782(2) 0.0697(5) Uani d . 1 . . C
H15 0.1397 0.3541 -0.3069 0.084 Uiso calc R 1 . . H
C16 0.2739(3) 0.3464(2) -0.1577(2) 0.0712(5) Uani d . 1 . . C
H16 0.2015 0.3867 -0.1064 0.085 Uiso calc R 1 . . H
C17 0.7194(3) 0.1110(3) -0.3642(2) 0.0909(7) Uani d . 1 . . C
H17A 0.8035 0.1810 -0.2934 0.136 Uiso calc R 1 . . H
H17B 0.7720 0.0720 -0.4327 0.136 Uiso calc R 1 . . H
H17C 0.6787 0.0431 -0.3447 0.136 Uiso calc R 1 . . H
C71 0.8420(2) 0.56352(18) 0.70586(16) 0.0635(5) Uani d . 1 . . C
C72 0.9076(2) 0.68742(18) 0.71750(15) 0.0606(4) Uani d . 1 . . C
H72 0.8751 0.7043 0.6513 0.073 Uiso calc R 1 . . H
C73 1.0208(2) 0.78580(16) 0.82674(15) 0.0541(4) Uani d . 1 . . C
C74 1.0678(2) 0.76016(16) 0.92587(15) 0.0536(4) Uani d . 1 . . C
C75 1.0056(2) 0.63703(18) 0.91353(17) 0.0615(4) Uani d . 1 . . C
H75 1.0393 0.6193 0.9791 0.074 Uiso calc R 1 . . H
C76 0.8930(2) 0.53917(19) 0.80371(18) 0.0665(5) Uani d . 1 . . C
H76 0.8516 0.4563 0.7963 0.080 Uiso calc R 1 . . H
C77 1.0531(4) 0.9437(2) 0.7527(2) 0.0900(7) Uani d . 1 . . C
H77A 1.0913 0.8826 0.6827 0.135 Uiso calc R 1 . . H
H77B 1.1108 1.0338 0.7808 0.135 Uiso calc R 1 . . H
H77C 0.9300 0.9373 0.7290 0.135 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
O O 0.0106 0.0060 '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'
C C 0.0033 0.0016 '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
C3 O3 H3 109.5 ?
C5 O5 H5 109.5 ?
C13 O13 C17 118.73(16) ?
C14 O14 H14 109.5 ?
C73 O73 C77 117.94(14) ?
C74 O74 H74 109.5 ?
C2 C1 C11 111.59(15) ?
C2 C1 H1A 109.3 ?
C11 C1 H1A 109.3 ?
C2 C1 H1B 109.3 ?
C11 C1 H1B 109.3 ?
H1A C1 H1B 108.0 ?
C1 C2 C3 116.56(14) y
C3 C2 H2A 108.2 ?
C1 C2 H2A 108.2 ?
C3 C2 H2B 108.2 ?
C1 C2 H2B 108.2 ?
H2A C2 H2B 107.3 ?
O3 C3 C2 113.52(14) y
O3 C3 C4 121.12(15) y
C2 C3 C4 125.36(15) y
C3 C4 C5 120.71(16) y
C3 C4 H4 119.6 ?
C5 C4 H4 119.6 ?
O5 C5 C4 120.83(15) y
O5 C5 C6 117.67(17) y
C4 C5 C6 121.50(17) y
C7 C6 C5 115.39(18) ?
C7 C6 H6A 108.4 ?
C5 C6 H6A 108.4 ?
C7 C6 H6B 108.4 ?
C5 C6 H6B 108.4 ?
H6A C6 H6B 107.5 ?
C6 C7 C71 117.27(18) ?
C6 C7 H7A 108.0 ?
C71 C7 H7A 108.0 ?
C6 C7 H7B 108.0 ?
C71 C7 H7B 108.0 ?
H7A C7 H7B 107.2 ?
C12 C11 C16 118.39(17) ?
C12 C11 C1 119.31(17) ?
C16 C11 C1 122.30(18) ?
C13 C12 C11 121.26(16) ?
C13 C12 H12 119.4 ?
C11 C12 H12 119.4 ?
O13 C13 C12 125.91(16) ?
O13 C13 C14 114.48(15) ?
C12 C13 C14 119.61(17) ?
C15 C14 O14 120.17(16) ?
C15 C14 C13 119.51(16) ?
O14 C14 C13 120.32(17) ?
C14 C15 C16 120.32(18) ?
C14 C15 H15 119.8 ?
C16 C15 H15 119.8 ?
C11 C16 C15 120.89(19) ?
C11 C16 H16 119.6 ?
C15 C16 H16 119.6 ?
O13 C17 H17A 109.5 ?
O13 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
O13 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C76 C71 C72 119.02(15) ?
C76 C71 C7 119.99(19) ?
C72 C71 C7 120.92(19) ?
C73 C72 C71 120.80(17) ?
C73 C72 H72 119.6 ?
C71 C72 H72 119.6 ?
O73 C73 C72 126.16(16) ?
O73 C73 C74 114.58(13) ?
C72 C73 C74 119.26(16) ?
O74 C74 C75 118.54(15) ?
O74 C74 C73 121.55(15) ?
C75 C74 C73 119.90(15) ?
C74 C75 C76 120.35(17) ?
C74 C75 H75 119.8 ?
C76 C75 H75 119.8 ?
C71 C76 C75 120.65(17) ?
C71 C76 H76 119.7 ?
C75 C76 H76 119.7 ?
O73 C77 H77A 109.5 ?
O73 C77 H77B 109.5 ?
H77A C77 H77B 109.5 ?
O73 C77 H77C 109.5 ?
H77A C77 H77C 109.5 ?
H77B C77 H77C 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
O3 C3 . 1.289(2) y
O3 H3 . 0.82 ?
O5 C5 . 1.276(2) y
O5 H5 . 0.82 ?
O13 C13 . 1.361(2) ?
O13 C17 . 1.408(3) ?
O14 C14 . 1.369(2) ?
O14 H14 . 0.82 ?
O73 C73 . 1.369(2) ?
O73 C77 . 1.412(2) ?
O74 C74 . 1.3657(19) ?
O74 H74 . 0.82 ?
C1 C2 . 1.508(3) y
C1 C11 . 1.515(2) y
C1 H1A . 0.97 ?
C1 H1B . 0.97 ?
C2 C3 . 1.498(2) y
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 C4 . 1.385(2) y
C4 C5 . 1.390(2) y
C4 H4 . 0.93 ?
C5 C6 . 1.509(2) y
C6 C7 . 1.441(3) y
C6 H6A . 0.97 ?
C6 H6B . 0.97 ?
C7 C71 . 1.518(2) y
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C11 C12 . 1.383(3) ?
C11 C16 . 1.385(3) ?
C12 C13 . 1.381(2) ?
C12 H12 . 0.93 ?
C13 C14 . 1.399(2) ?
C14 C15 . 1.368(3) ?
C15 C16 . 1.388(3) ?
C15 H15 . 0.93 ?
C16 H16 . 0.93 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C71 C76 . 1.373(3) ?
C71 C72 . 1.395(3) ?
C72 C73 . 1.388(2) ?
C72 H72 . 0.93 ?
C73 C74 . 1.393(2) ?
C74 C75 . 1.376(2) ?
C75 C76 . 1.388(3) ?
C75 H75 . 0.93 ?
C76 H76 . 0.93 ?
C77 H77A . 0.96 ?
C77 H77B . 0.96 ?
C77 H77C . 0.96 ?
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
_geom_hbond_publ_flag
O3 H3 O5 . 0.82 1.74 2.472(2) 147 y
O5 H5 O3 . 0.82 1.75 2.472(2) 146 y
O14 H14 O5 1_554 0.82 2.18 2.934(2) 153 y
O14 H14 O13 . 0.82 2.21 2.655(2) 114 y
O74 H74 O3 1_666 0.82 2.14 2.773(2) 134 y
O74 H74 O73 . 0.82 2.23 2.678(2) 115 y
C7 H7A O13 1_556 0.97 2.54 3.510(3) 173 y
C12 H12 O74 2_766 0.93 2.51 3.411(2) 162 y
C1 H1B Cg1 2_665 0.97 3.29 3.891 122 y
C2 H2A Cg2 2_666 0.97 3.20 3.821 123 y
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
C11 C1 C2 C3 172.57(16)
C1 C2 C3 O3 172.36(17)
C1 C2 C3 C4 -7.5(3)
O3 C3 C4 C5 -0.4(3)
C2 C3 C4 C5 179.42(18)
C3 C4 C5 O5 -2.0(3)
C3 C4 C5 C6 178.3(2)
O5 C5 C6 C7 -43.9(4)
C4 C5 C6 C7 135.7(3)
C5 C6 C7 C71 176.7(2)
C2 C1 C11 C12 -80.3(2)
C2 C1 C11 C16 99.1(2)
C16 C11 C12 C13 1.7(3)
C1 C11 C12 C13 -178.90(16)
C17 O13 C13 C12 5.2(3)
C17 O13 C13 C14 -176.06(19)
C11 C12 C13 O13 178.44(17)
C11 C12 C13 C14 -0.3(3)
O13 C13 C14 C15 -179.96(17)
C12 C13 C14 C15 -1.1(3)
O13 C13 C14 O14 -0.8(2)
C12 C13 C14 O14 178.08(16)
O14 C14 C15 C16 -178.18(17)
C13 C14 C15 C16 1.0(3)
C12 C11 C16 C15 -1.8(3)
C1 C11 C16 C15 178.82(17)
C14 C15 C16 C11 0.5(3)
C6 C7 C71 C76 -125.7(3)
C6 C7 C71 C72 57.5(3)
C76 C71 C72 C73 -0.9(3)
C7 C71 C72 C73 175.95(17)
C77 O73 C73 C72 -1.3(3)
C77 O73 C73 C74 179.3(2)
C71 C72 C73 O73 -179.85(17)
C71 C72 C73 C74 -0.5(3)
O73 C73 C74 O74 0.4(3)
C72 C73 C74 O74 -178.99(16)
O73 C73 C74 C75 -178.86(16)
C72 C73 C74 C75 1.7(3)
O74 C74 C75 C76 179.18(17)
C73 C74 C75 C76 -1.5(3)
C72 C71 C76 C75 1.1(3)
C7 C71 C76 C75 -175.75(18)
C74 C75 C76 C71 0.1(3)
