#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/51/2205183.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_2205183
loop_
_publ_author_name
'Sathiya Moorthi, S.'
'Chinnakali, K.'
'Nanjundan, S.'
'Radhika, R.'
'Fun, Hoong-Kun'
'Yu, Xiao-Lan'
_publ_section_title
;
 1-(4-Hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o480
_journal_page_last               o482
_journal_paper_doi               10.1107/S1600536805001698
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C16 H14 O3'
_chemical_formula_moiety         'C16 H14 O3'
_chemical_formula_sum            'C16 H14 O3'
_chemical_formula_weight         254.27
_chemical_name_systematic
;
1-(4-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-ene-1-one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.4346(8)
_cell_length_b                   11.4998(7)
_cell_length_c                   16.6055(10)
_cell_measurement_reflns_used    6162
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.726
_cell_measurement_theta_min      4.906
_cell_volume                     2565.5(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Siemens SMART 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  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15000
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       Block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.218
_refine_ls_extinction_coef       0.0097(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0440
_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)+(0.0671P)²+0.4382P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1260
_reflns_number_gt                2513
_reflns_number_total             3015
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6322.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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_database_code               2205183
_cod_database_fobs_code          2205183
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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_type_symbol
O1 0.29376(7) 0.63939(9) 0.08155(6) 0.0562(3) Uani d . 1 O
O2 0.43974(7) 0.06151(9) 0.36966(6) 0.0586(3) Uani d . 1 O
O3 -0.17087(6) 0.67671(9) 0.01419(7) 0.0562(3) Uani d . 1 O
H3 -0.1735 0.7338 -0.0153 0.084 Uiso calc R 1 H
C1 0.45688(9) 0.31078(11) 0.23901(8) 0.0448(3) Uani d . 1 C
H1 0.5070 0.3530 0.2138 0.054 Uiso calc R 1 H
C2 0.48204(9) 0.21708(12) 0.28625(8) 0.0487(3) Uani d . 1 C
H2 0.5485 0.1965 0.2926 0.058 Uiso calc R 1 H
C3 0.40830(9) 0.15332(11) 0.32447(7) 0.0424(3) Uani d . 1 C
C4 0.30962(9) 0.18459(12) 0.31520(8) 0.0489(3) Uani d . 1 C
H4 0.2598 0.1425 0.3409 0.059 Uiso calc R 1 H
C5 0.28576(9) 0.27863(12) 0.26760(8) 0.0497(3) Uani d . 1 C
H5 0.2192 0.2991 0.2617 0.060 Uiso calc R 1 H
C6 0.35787(9) 0.34405(10) 0.22805(7) 0.0401(3) Uani d . 1 C
C7 0.33350(9) 0.44287(11) 0.17658(7) 0.0429(3) Uani d . 1 C
H7 0.3866 0.4838 0.1545 0.051 Uiso calc R 1 H
C8 0.24320(10) 0.47962(12) 0.15846(8) 0.0504(3) Uani d . 1 C
H8 0.1891 0.4399 0.1800 0.060 Uiso calc R 1 H
C9 0.22370(9) 0.58009(11) 0.10598(8) 0.0425(3) Uani d . 1 C
C10 0.11971(8) 0.60669(10) 0.08370(7) 0.0388(3) Uani d . 1 C
C11 0.03902(9) 0.54121(11) 0.11133(7) 0.0433(3) Uani d . 1 C
H11 0.0505 0.4792 0.1461 0.052 Uiso calc R 1 H
C12 -0.05700(9) 0.56614(11) 0.08838(8) 0.0460(3) Uani d . 1 C
H12 -0.1095 0.5214 0.1077 0.055 Uiso calc R 1 H
C13 -0.07549(9) 0.65788(10) 0.03645(7) 0.0409(3) Uani d . 1 C
C14 0.00312(9) 0.72515(11) 0.00864(8) 0.0431(3) Uani d . 1 C
H14 -0.0089 0.7875 -0.0257 0.052 Uiso calc R 1 H
C15 0.09898(9) 0.69932(11) 0.03210(8) 0.0441(3) Uani d . 1 C
H15 0.1512 0.7448 0.0131 0.053 Uiso calc R 1 H
C16 0.36787(13) -0.00137(14) 0.41476(11) 0.0679(4) Uani d . 1 C
H16A 0.4007 -0.0594 0.4467 0.102 Uiso calc R 1 H
H16B 0.3219 -0.0383 0.3786 0.102 Uiso calc R 1 H
H16C 0.3325 0.0511 0.4494 0.102 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
C3 O2 C16 118.32(11)
C13 O3 H3 109.5
C2 C1 C6 121.56(12)
C2 C1 H1 119.2
C6 C1 H1 119.2
C1 C2 C3 120.00(11)
C1 C2 H2 120.0
C3 C2 H2 120.0
O2 C3 C4 124.08(12)
O2 C3 C2 116.13(11)
C4 C3 C2 119.79(12)
C5 C4 C3 119.43(12)
C5 C4 H4 120.3
C3 C4 H4 120.3
C4 C5 C6 122.24(12)
C4 C5 H5 118.9
C6 C5 H5 118.9
C5 C6 C1 116.98(11)
C5 C6 C7 122.78(11)
C1 C6 C7 120.24(11)
C8 C7 C6 126.11(12)
C8 C7 H7 116.9
C6 C7 H7 116.9
C7 C8 C9 123.40(12)
C7 C8 H8 118.3
C9 C8 H8 118.3
O1 C9 C8 119.62(11)
O1 C9 C10 121.72(11)
C8 C9 C10 118.65(11)
C15 C10 C11 117.27(11)
C15 C10 C9 120.04(11)
C11 C10 C9 122.68(11)
C12 C11 C10 121.62(11)
C12 C11 H11 119.2
C10 C11 H11 119.2
C11 C12 C13 119.97(11)
C11 C12 H12 120.0
C13 C12 H12 120.0
O3 C13 C12 117.55(11)
O3 C13 C14 122.77(11)
C12 C13 C14 119.67(11)
C15 C14 C13 119.80(11)
C15 C14 H14 120.1
C13 C14 H14 120.1
C14 C15 C10 121.65(11)
C14 C15 H15 119.2
C10 C15 H15 119.2
O2 C16 H16A 109.5
O2 C16 H16B 109.5
H16A C16 H16B 109.5
O2 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.2311(15)
O2 C3 1.3624(15)
O2 C16 1.4199(18)
O3 C13 1.3511(14)
O3 H3 0.82
C1 C2 1.3750(18)
C1 C6 1.3959(16)
C1 H1 0.93
C2 C3 1.3863(18)
C2 H2 0.93
C3 C4 1.3822(17)
C4 C5 1.3773(19)
C4 H4 0.93
C5 C6 1.3913(17)
C5 H5 0.93
C6 C7 1.4592(17)
C7 C8 1.3194(18)
C7 H7 0.93
C8 C9 1.4707(18)
C8 H8 0.93
C9 C10 1.4772(16)
C10 C15 1.3952(17)
C10 C11 1.3974(16)
C11 C12 1.3753(17)
C11 H11 0.93
C12 C13 1.3850(17)
C12 H12 0.93
C13 C14 1.3882(17)
C14 C15 1.3779(17)
C14 H14 0.93
C15 H15 0.93
C16 H16A 0.96
C16 H16B 0.96
C16 H16C 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
O3 H3 O1 4_465 0.82 1.88 2.688(2) 169
C1 H1 O2 3_655 0.93 2.86 3.674(2) 147
C4 H4 O3 3_545 0.93 2.72 3.393(2) 130
C7 H7 O1 1_555 0.93 2.50 2.808(2) 100
C7 H7 O2 3_655 0.93 2.53 3.425(2) 162
C14 H14 O1 4_465 0.93 2.93 3.547(2) 125
C14 H14 O2 2_564 0.93 2.63 3.455(2) 149
C15 H15 O1 1_555 0.93 2.54 2.828(2) 99
C15 H15 O3 4_565 0.93 2.60 3.490(2) 162
C16 H16A O1 7_566 0.96 2.82 3.344(2) 116
C16 H16C O3 3_545 0.96 2.68 3.548(2) 151
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
C6 C1 C2 C3 -0.1(2)
C16 O2 C3 C4 -4.7(2)
C16 O2 C3 C2 175.46(14)
C1 C2 C3 O2 179.61(12)
C1 C2 C3 C4 -0.3(2)
O2 C3 C4 C5 -179.54(13)
C2 C3 C4 C5 0.3(2)
C3 C4 C5 C6 0.0(2)
C4 C5 C6 C1 -0.4(2)
C4 C5 C6 C7 179.13(12)
C2 C1 C6 C5 0.48(19)
C2 C1 C6 C7 -179.09(12)
C5 C6 C7 C8 -2.8(2)
C1 C6 C7 C8 176.71(13)
C6 C7 C8 C9 -179.96(12)
C7 C8 C9 O1 -5.4(2)
C7 C8 C9 C10 174.34(13)
O1 C9 C10 C15 1.6(2)
C8 C9 C10 C15 -178.10(12)
O1 C9 C10 C11 -179.40(13)
C8 C9 C10 C11 0.88(19)
C15 C10 C11 C12 0.42(19)
C9 C10 C11 C12 -178.59(12)
C10 C11 C12 C13 0.2(2)
C11 C12 C13 O3 178.32(12)
C11 C12 C13 C14 -0.8(2)
O3 C13 C14 C15 -178.30(12)
C12 C13 C14 C15 0.8(2)
C13 C14 C15 C10 -0.1(2)
C11 C10 C15 C14 -0.45(19)
C9 C10 C15 C14 178.59(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5653390
