#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/32/2213244.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_2213244
loop_
_publ_author_name
'Jeannie Bee-Jan Teh'
'P. S. Patil'
'Hoong-Kun Fun'
'Ibrahim Abdul Razak'
'S. M. Dharmaprakash'
_publ_section_title
;
 1,3-Bis(3,4-dimethoxyphenyl)prop-2-en-1-one
;
_journal_coeditor_code           CI2365
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2613
_journal_page_last               o2613
_journal_paper_doi               10.1107/S160053680701865X
_journal_volume                  63
_journal_year                    2007
_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_systematic
;
1,3-Bis(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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.148(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3543(2)
_cell_length_b                   7.9014(2)
_cell_length_c                   24.0405(6)
_cell_measurement_reflns_used    3229
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      30.10
_cell_measurement_theta_min      2.27
_cell_volume                     1706.78(7)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            21071
_diffrn_reflns_theta_full        30.10
_diffrn_reflns_theta_max         30.10
_diffrn_reflns_theta_min         2.27
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9695
_exptl_absorpt_correction_T_min  0.9612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         5021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1475
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0671P)²+0.0194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1628
_reflns_number_gt                2222
_reflns_number_total             5021
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2365.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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      'P 21/c'
_cod_database_code               2213244
_cod_database_fobs_code          2213244
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
O O1 0.67098(13) 0.57700(17) 0.16281(5) 0.0677(4) Uani d . 1
O O2 0.75255(13) 0.59791(19) 0.06831(5) 0.0759(4) Uani d . 1
O O3 -0.08215(15) 1.0025(2) 0.06712(5) 0.0941(5) Uani d . 1
O O4 -0.38043(13) 1.09985(18) 0.20964(5) 0.0733(4) Uani d . 1
O O5 -0.22752(14) 0.96920(17) 0.30656(5) 0.0698(4) Uani d . 1
C C1 0.43616(18) 0.7133(2) 0.11822(7) 0.0543(5) Uani d . 1
H H1 0.4059 0.7016 0.1517 0.065 Uiso calc R 1
C C2 0.57227(18) 0.6523(2) 0.11712(7) 0.0536(4) Uani d . 1
C C3 0.61759(19) 0.6654(2) 0.06602(7) 0.0591(5) Uani d . 1
C C4 0.5246(2) 0.7434(3) 0.01857(7) 0.0720(6) Uani d . 1
H H4 0.5538 0.7533 -0.0152 0.086 Uiso calc R 1
C C5 0.3879(2) 0.8078(3) 0.02014(7) 0.0678(5) Uani d . 1
H H5 0.3271 0.8611 -0.0124 0.081 Uiso calc R 1
C C6 0.34124(18) 0.7934(2) 0.06965(7) 0.0558(5) Uani d . 1
C C7 0.19693(19) 0.8618(2) 0.07048(7) 0.0618(5) Uani d . 1
H H7 0.1403 0.9114 0.0364 0.074 Uiso calc R 1
C C8 0.13802(19) 0.8609(2) 0.11453(7) 0.0618(5) Uani d . 1
H H8 0.1914 0.8103 0.1490 0.074 Uiso calc R 1
C C9 -0.0071(2) 0.9355(2) 0.11174(7) 0.0610(5) Uani d . 1
C C10 -0.06215(18) 0.9333(2) 0.16383(7) 0.0522(4) Uani d . 1
C C11 -0.19713(18) 1.0139(2) 0.16105(7) 0.0555(5) Uani d . 1
H H11 -0.2515 1.0622 0.1263 0.067 Uiso calc R 1
C C12 -0.25045(18) 1.0230(2) 0.20840(7) 0.0535(4) Uani d . 1
C C13 -0.16737(19) 0.9508(2) 0.26100(7) 0.0560(5) Uani d . 1
C C14 -0.03606(19) 0.8694(2) 0.26395(7) 0.0610(5) Uani d . 1
H H14 0.0183 0.8205 0.2986 0.073 Uiso calc R 1
C C15 0.01550(19) 0.8599(2) 0.21544(7) 0.0581(5) Uani d . 1
H H15 0.1040 0.8031 0.2176 0.070 Uiso calc R 1
C C16 0.6347(2) 0.5778(3) 0.21637(7) 0.0736(6) Uani d . 1
H H16A 0.7159 0.5310 0.2461 0.110 Uiso calc R 1
H H16B 0.5469 0.5110 0.2129 0.110 Uiso calc R 1
H H16C 0.6167 0.6919 0.2264 0.110 Uiso calc R 1
C C17 0.7989(2) 0.6041(3) 0.01652(8) 0.0914(7) Uani d . 1
H H17A 0.8921 0.5461 0.0226 0.137 Uiso calc R 1
H H17B 0.8104 0.7200 0.0065 0.137 Uiso calc R 1
H H17C 0.7253 0.5505 -0.0144 0.137 Uiso calc R 1
C C18 -0.4705(2) 1.1666(3) 0.15663(8) 0.0774(6) Uani d . 1
H H18A -0.5612 1.2104 0.1623 0.116 Uiso calc R 1
H H18C -0.4935 1.0786 0.1280 0.116 Uiso calc R 1
H H18B -0.4179 1.2560 0.1437 0.116 Uiso calc R 1
C C19 -0.1418(3) 0.9055(3) 0.36133(8) 0.0897(7) Uani d . 1
H H19C -0.1914 0.9313 0.3903 0.135 Uiso calc R 1
H H19A -0.0452 0.9573 0.3716 0.135 Uiso calc R 1
H H19B -0.1313 0.7851 0.3589 0.135 Uiso calc R 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 0.0000 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
C2 O1 C16 116.78(13)
C3 O2 C17 117.08(15)
C12 O4 C18 117.07(13)
C13 O5 C19 116.69(14)
C2 C1 C6 121.24(14)
C2 C1 H1 119.4
C6 C1 H1 119.4
O1 C2 C1 124.40(14)
O1 C2 C3 115.76(15)
C1 C2 C3 119.84(16)
O2 C3 C4 125.27(15)
O2 C3 C2 115.93(16)
C4 C3 C2 118.81(16)
C3 C4 C5 121.21(16)
C3 C4 H4 119.4
C5 C4 H4 119.4
C6 C5 C4 120.52(17)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C1 118.35(15)
C5 C6 C7 119.75(16)
C1 C6 C7 121.90(14)
C8 C7 C6 127.00(16)
C8 C7 H7 116.5
C6 C7 H7 116.5
C7 C8 C9 123.26(17)
C7 C8 H8 118.4
C9 C8 H8 118.4
O3 C9 C8 120.76(16)
O3 C9 C10 119.71(16)
C8 C9 C10 119.51(15)
C15 C10 C11 118.48(15)
C15 C10 C9 123.09(15)
C11 C10 C9 118.41(15)
C12 C11 C10 121.20(15)
C12 C11 H11 119.4
C10 C11 H11 119.4
C11 C12 O4 125.09(15)
C11 C12 C13 119.27(15)
O4 C12 C13 115.63(14)
C14 C13 O5 124.69(15)
C14 C13 C12 119.97(15)
O5 C13 C12 115.34(15)
C13 C14 C15 119.98(16)
C13 C14 H14 120.0
C15 C14 H14 120.0
C10 C15 C14 121.07(16)
C10 C15 H15 119.5
C14 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 H18C 109.5
H18A C18 H18C 109.5
O4 C18 H18B 109.5
H18A C18 H18B 109.5
H18C C18 H18B 109.5
O5 C19 H19C 109.5
O5 C19 H19A 109.5
H19C C19 H19A 109.5
O5 C19 H19B 109.5
H19C C19 H19B 109.5
H19A C19 H19B 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3599(19)
O1 C16 1.4200(19)
O2 C3 1.357(2)
O2 C17 1.428(2)
O3 C9 1.2268(19)
O4 C12 1.3667(19)
O4 C18 1.420(2)
O5 C13 1.3712(18)
O5 C19 1.429(2)
C1 C2 1.368(2)
C1 C6 1.405(2)
C1 H1 0.93
C2 C3 1.411(2)
C3 C4 1.373(2)
C4 C5 1.386(2)
C4 H4 0.93
C5 C6 1.382(2)
C5 H5 0.93
C6 C7 1.460(2)
C7 C8 1.323(2)
C7 H7 0.93
C8 C9 1.465(2)
C8 H8 0.93
C9 C10 1.480(2)
C10 C15 1.379(2)
C10 C11 1.399(2)
C11 C12 1.366(2)
C11 H11 0.93
C12 C13 1.408(2)
C13 C14 1.371(2)
C14 C15 1.382(2)
C14 H14 0.93
C15 H15 0.93
C16 H16A 0.96
C16 H16B 0.96
C16 H16C 0.96
C17 H17A 0.96
C17 H17B 0.96
C17 H17C 0.96
C18 H18A 0.96
C18 H18C 0.96
C18 H18B 0.96
C19 H19C 0.96
C19 H19A 0.96
C19 H19B 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
C5 H5 O3 3_575 0.93 2.54 3.390(2) 151 y
C7 H7 O3 3_575 0.93 2.49 3.357(2) 155 y
C17 H17C Cg1 3_665 0.96 2.98 3.865(2) 154 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
C16 O1 C2 C1 -6.4(3)
C16 O1 C2 C3 173.75(15)
C6 C1 C2 O1 178.49(16)
C6 C1 C2 C3 -1.7(3)
C17 O2 C3 C4 -2.1(3)
C17 O2 C3 C2 177.85(17)
O1 C2 C3 O2 1.4(2)
C1 C2 C3 O2 -178.40(16)
O1 C2 C3 C4 -178.63(17)
C1 C2 C3 C4 1.5(3)
O2 C3 C4 C5 179.54(18)
C2 C3 C4 C5 -0.4(3)
C3 C4 C5 C6 -0.6(3)
C4 C5 C6 C1 0.5(3)
C4 C5 C6 C7 -179.96(18)
C2 C1 C6 C5 0.7(3)
C2 C1 C6 C7 -178.87(16)
C5 C6 C7 C8 -178.66(19)
C1 C6 C7 C8 0.9(3)
C6 C7 C8 C9 178.91(18)
C7 C8 C9 O3 0.5(3)
C7 C8 C9 C10 -178.07(17)
O3 C9 C10 C15 179.77(18)
C8 C9 C10 C15 -1.7(3)
O3 C9 C10 C11 -2.2(3)
C8 C9 C10 C11 176.37(16)
C15 C10 C11 C12 1.1(3)
C9 C10 C11 C12 -176.99(16)
C10 C11 C12 O4 179.64(16)
C10 C11 C12 C13 0.4(3)
C18 O4 C12 C11 3.8(3)
C18 O4 C12 C13 -176.98(16)
C19 O5 C13 C14 3.3(3)
C19 O5 C13 C12 -176.65(17)
C11 C12 C13 C14 -1.4(3)
O4 C12 C13 C14 179.34(16)
C11 C12 C13 O5 178.57(15)
O4 C12 C13 O5 -0.7(2)
O5 C13 C14 C15 -179.22(16)
C12 C13 C14 C15 0.7(3)
C11 C10 C15 C14 -1.8(3)
C9 C10 C15 C14 176.23(16)
C13 C14 C15 C10 0.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655215
