#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/65/2226508.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_2226508
loop_
_publ_author_name
'van Tonder, Johannes H.'
'Muller, Theunis J.'
'Bezuidenhoudt, Barend C. B.'
_publ_section_title
;
 2',3,4,4'-Tetramethoxychalcone
;
_journal_coeditor_code           HG2688
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1798
_journal_page_last               o1799
_journal_paper_doi               10.1107/S1600536810022142
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H20 O5'
_chemical_formula_moiety         'C19 H20 O5'
_chemical_formula_sum            'C19 H20 O5'
_chemical_formula_weight         328.35
_chemical_name_common
;
2',3,4,4'-Tetramethoxychalcone
;
_chemical_name_systematic
;
1-(2,4-dimethoxyphenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.000
_cell_angle_beta                 109.489(2)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   12.5839(7)
_cell_length_b                   11.7204(7)
_cell_length_c                   12.1339(6)
_cell_measurement_reflns_used    7154
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.57
_cell_measurement_theta_min      2.44
_cell_volume                     1687.07(16)
_computing_cell_refinement       'Saint-Plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenberg & Putz, 2005)'
_computing_publication_material  'WingGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            32681
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.487
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0998P)²+0.0628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1878
_reflns_number_gt                2539
_reflns_number_total             4205
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            hg2688.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226508
_cod_database_fobs_code          2226508
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
C C1 0.57536(15) 0.12721(14) 0.10767(13) 0.0572(4) Uani d . 1 . .
C C2 0.66866(16) 0.07753(15) 0.09002(15) 0.0635(5) Uani d . 1 . .
H H2 0.7138 0.027 0.1449 0.076 Uiso calc R 1 . .
C C3 0.69406(17) 0.10359(16) -0.00938(16) 0.0665(5) Uani d . 1 . .
C C4 0.62632(18) 0.17787(18) -0.09154(16) 0.0724(5) Uani d . 1 . .
H H4 0.6422 0.1941 -0.1594 0.087 Uiso calc R 1 . .
C C5 0.53595(17) 0.22720(17) -0.07222(14) 0.0654(5) Uani d . 1 . .
H H5 0.4918 0.2781 -0.1274 0.079 Uiso calc R 1 . .
C C6 0.50707(15) 0.20426(14) 0.02731(13) 0.0555(4) Uani d . 1 . .
C C7 0.40909(15) 0.26733(15) 0.04011(13) 0.0582(4) Uani d . 1 . .
C C8 0.33980(16) 0.21568(16) 0.10368(15) 0.0603(5) Uani d . 1 . .
C C9 0.25176(15) 0.26831(16) 0.11757(14) 0.0596(5) Uani d . 1 . .
C C10 0.18227(14) 0.22631(15) 0.18413(14) 0.0570(4) Uani d . 1 . .
C C11 0.20392(14) 0.12066(15) 0.24240(14) 0.0571(4) Uani d . 1 . .
H H11 0.2627 0.0756 0.2367 0.068 Uiso calc R 1 . .
C C12 0.14066(14) 0.08267(15) 0.30728(14) 0.0574(4) Uani d . 1 . .
C C13 0.05259(14) 0.15026(17) 0.31711(15) 0.0614(5) Uani d . 1 . .
C C14 0.02979(16) 0.25345(18) 0.26000(16) 0.0692(5) Uani d . 1 . .
H H14 -0.0292 0.2982 0.2656 0.083 Uiso calc R 1 . .
C C15 0.09404(16) 0.29117(17) 0.19425(16) 0.0676(5) Uani d . 1 . .
H H15 0.0777 0.3612 0.1563 0.081 Uiso calc R 1 . .
C C16 0.60374(18) 0.01862(18) 0.28377(17) 0.0782(6) Uani d . 1 . .
H H16A 0.5762 0.0164 0.3486 0.117 Uiso calc R 1 . .
H H16B 0.6836 0.0318 0.312 0.117 Uiso calc R 1 . .
H H16C 0.5882 -0.0529 0.2429 0.117 Uiso calc R 1 . .
C C17 0.86153(19) -0.0100(2) 0.0519(2) 0.0954(7) Uani d . 1 . .
H H17A 0.9212 -0.0335 0.0241 0.143 Uiso calc R 1 . .
H H17B 0.8224 -0.0761 0.0653 0.143 Uiso calc R 1 . .
H H17C 0.8927 0.0315 0.1237 0.143 Uiso calc R 1 . .
C C18 0.24973(17) -0.08614(17) 0.36379(18) 0.0710(5) Uani d . 1 . .
H H18A 0.2528 -0.1544 0.4085 0.107 Uiso calc R 1 . .
H H18B 0.3184 -0.0439 0.3967 0.107 Uiso calc R 1 . .
H H18C 0.2405 -0.1061 0.2844 0.107 Uiso calc R 1 . .
C C19 -0.09188(18) 0.1716(2) 0.4026(2) 0.0927(7) Uani d . 1 . .
H H19A -0.1252 0.1302 0.451 0.139 Uiso calc R 1 . .
H H19B -0.1484 0.1879 0.3286 0.139 Uiso calc R 1 . .
H H19C -0.0607 0.2418 0.4403 0.139 Uiso calc R 1 . .
O O1 0.54938(13) 0.10796(12) 0.20672(10) 0.0780(4) Uani d . 1 . .
O O2 0.78452(13) 0.06147(14) -0.03354(13) 0.0874(5) Uani d . 1 . .
O O3 0.38578(12) 0.36122(11) -0.00560(11) 0.0767(4) Uani d . 1 . .
O O4 0.15725(11) -0.01826(11) 0.36644(12) 0.0717(4) Uani d . 1 . .
O O5 -0.00515(11) 0.10484(13) 0.38441(12) 0.0785(4) Uani d . 1 . .
H H8 0.3591(17) 0.1401(19) 0.1332(17) 0.075(6) Uiso d . 1 . .
H H9 0.2294(16) 0.3460(17) 0.0808(16) 0.071(5) Uiso d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C2 . . 121.95(15) ?
O1 C1 C6 . . 116.73(16) ?
C2 C1 C6 . . 121.24(15) ?
C3 C2 C1 . . 119.70(17) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
O2 C3 C2 . . 124.22(19) ?
O2 C3 C4 . . 115.62(17) ?
C2 C3 C4 . . 120.16(18) ?
C5 C4 C3 . . 119.46(17) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
C4 C5 C6 . . 122.60(18) ?
C4 C5 H5 . . 118.7 ?
C6 C5 H5 . . 118.7 ?
C1 C6 C5 . . 116.82(17) ?
C1 C6 C7 . . 125.93(15) ?
C5 C6 C7 . . 117.21(15) ?
O3 C7 C8 . . 120.85(17) ?
O3 C7 C6 . . 118.74(16) ?
C8 C7 C6 . . 120.39(15) ?
C9 C8 C7 . . 122.73(18) ?
C9 C8 H8 . . 120.1(12) ?
C7 C8 H8 . . 117.1(12) ?
C8 C9 C10 . . 126.39(18) ?
C8 C9 H9 . . 118.9(11) ?
C10 C9 H9 . . 114.7(11) ?
C15 C10 C11 . . 117.73(17) ?
C15 C10 C9 . . 120.67(17) ?
C11 C10 C9 . . 121.57(16) ?
C12 C11 C10 . . 121.57(16) ?
C12 C11 H11 . . 119.2 ?
C10 C11 H11 . . 119.2 ?
O4 C12 C11 . . 124.71(16) ?
O4 C12 C13 . . 115.65(15) ?
C11 C12 C13 . . 119.64(17) ?
O5 C13 C14 . . 125.41(17) ?
O5 C13 C12 . . 115.08(17) ?
C14 C13 C12 . . 119.51(17) ?
C13 C14 C15 . . 120.49(17) ?
C13 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
C14 C15 C10 . . 121.04(18) ?
C14 C15 H15 . . 119.5 ?
C10 C15 H15 . . 119.5 ?
O1 C16 H16A . . 109.5 ?
O1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O1 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O2 C17 H17A . . 109.5 ?
O2 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O2 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O4 C18 H18A . . 109.5 ?
O4 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O4 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O5 C19 H19A . . 109.5 ?
O5 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O5 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C1 O1 C16 . . 119.85(15) ?
C3 O2 C17 . . 118.05(17) ?
C12 O4 C18 . . 117.21(14) ?
C13 O5 C19 . . 117.86(18) ?
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
C1 O1 . 1.3654(19) ?
C1 C2 . 1.390(3) ?
C1 C6 . 1.395(2) ?
C2 C3 . 1.381(3) ?
C2 H2 . 0.93 ?
C3 O2 . 1.359(2) ?
C3 C4 . 1.382(3) ?
C4 C5 . 1.364(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.398(2) ?
C5 H5 . 0.93 ?
C6 C7 . 1.489(3) ?
C7 O3 . 1.223(2) ?
C7 C8 . 1.473(3) ?
C8 C9 . 1.327(3) ?
C8 H8 . 0.96(2) ?
C9 C10 . 1.460(3) ?
C9 H9 . 1.01(2) ?
C10 C15 . 1.384(3) ?
C10 C11 . 1.407(2) ?
C11 C12 . 1.367(2) ?
C11 H11 . 0.93 ?
C12 O4 . 1.363(2) ?
C12 C13 . 1.399(2) ?
C13 O5 . 1.369(2) ?
C13 C14 . 1.376(3) ?
C14 C15 . 1.384(3) ?
C14 H14 . 0.93 ?
C15 H15 . 0.93 ?
C16 O1 . 1.418(2) ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 O2 . 1.430(3) ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C18 O4 . 1.419(2) ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C19 O5 . 1.418(3) ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 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
C8 H8 O1 . 0.96(2) 2.29(2) 2.813(3) 113.6(15)
C18 H18B O3 4_566 0.96 2.46 3.253(3) 140.1
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . -177.22(16) ?
C6 C1 C2 C3 . . . . -0.7(3) ?
C1 C2 C3 O2 . . . . 178.59(16) ?
C1 C2 C3 C4 . . . . -0.7(3) ?
O2 C3 C4 C5 . . . . -177.74(17) ?
C2 C3 C4 C5 . . . . 1.6(3) ?
C3 C4 C5 C6 . . . . -1.2(3) ?
O1 C1 C6 C5 . . . . 177.78(15) ?
C2 C1 C6 C5 . . . . 1.1(2) ?
O1 C1 C6 C7 . . . . 0.2(2) ?
C2 C1 C6 C7 . . . . -176.47(15) ?
C4 C5 C6 C1 . . . . -0.2(3) ?
C4 C5 C6 C7 . . . . 177.62(16) ?
C1 C6 C7 O3 . . . . 150.16(17) ?
C5 C6 C7 O3 . . . . -27.4(2) ?
C1 C6 C7 C8 . . . . -31.7(2) ?
C5 C6 C7 C8 . . . . 150.79(16) ?
O3 C7 C8 C9 . . . . -1.9(3) ?
C6 C7 C8 C9 . . . . 179.96(15) ?
C7 C8 C9 C10 . . . . -176.58(15) ?
C8 C9 C10 C15 . . . . 178.36(17) ?
C8 C9 C10 C11 . . . . 0.0(3) ?
C15 C10 C11 C12 . . . . -0.2(2) ?
C9 C10 C11 C12 . . . . 178.26(15) ?
C10 C11 C12 O4 . . . . -179.63(15) ?
C10 C11 C12 C13 . . . . -0.4(2) ?
O4 C12 C13 O5 . . . . -0.4(2) ?
C11 C12 C13 O5 . . . . -179.68(14) ?
O4 C12 C13 C14 . . . . -179.86(15) ?
C11 C12 C13 C14 . . . . 0.9(3) ?
O5 C13 C14 C15 . . . . 179.90(17) ?
C12 C13 C14 C15 . . . . -0.7(3) ?
C13 C14 C15 C10 . . . . 0.1(3) ?
C11 C10 C15 C14 . . . . 0.3(3) ?
C9 C10 C15 C14 . . . . -178.11(16) ?
C2 C1 O1 C16 . . . . -12.8(3) ?
C6 C1 O1 C16 . . . . 170.51(17) ?
C2 C3 O2 C17 . . . . -3.2(3) ?
C4 C3 O2 C17 . . . . 176.09(18) ?
C11 C12 O4 C18 . . . . 2.6(2) ?
C13 C12 O4 C18 . . . . -176.60(15) ?
C14 C13 O5 C19 . . . . -3.6(3) ?
C12 C13 O5 C19 . . . . 176.98(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4755731
