#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/16/2221623.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_2221623
loop_
_publ_author_name
'Razak, Ibrahim Abdul'
'Fun, Hoong-Kun'
'Ngaini, Zainab'
'Rahman, Norashikin Irdawaty Abd'
'Hussain, Hasnain'
_publ_section_title
;
 (E)-3-[4-(Decyloxy)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
;
_journal_coeditor_code           CI2782
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1092
_journal_page_last               o1093
_journal_paper_doi               10.1107/S160053680901441X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C25 H32 O3'
_chemical_formula_moiety         'C25 H32 O3'
_chemical_formula_sum            'C25 H32 O3'
_chemical_formula_weight         380.51
_chemical_name_systematic
;
(E)-3-[4-(Decyloxy)phenyl]-1-(4-hydroxyphenyl)prop-2-en-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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.5192(3)
_cell_length_b                   9.9839(3)
_cell_length_c                   40.8415(12)
_cell_measurement_reflns_used    4176
_cell_measurement_temperature    100
_cell_measurement_theta_max      23.92
_cell_measurement_theta_min      2.18
_cell_volume                     4289.3(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'π and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            42832
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_correction_T_min  0.9572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.584
_exptl_crystal_size_mid          0.494
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.220
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0641
_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)+(0.0368P)²+2.6345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                3526
_reflns_number_total             4922
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2782.cif
_cod_data_source_block           I
_cod_database_code               2221623
_cod_database_fobs_code          2221623
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_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
O O1 0.97999(14) 0.70636(15) 0.20018(3) 0.0232(3) Uani d . 1 . .
O O2 0.66825(13) 0.56794(14) 0.32684(3) 0.0228(3) Uani d . 1 . .
O O3 0.93786(13) -0.03516(14) 0.45190(3) 0.0227(3) Uani d . 1 . .
C C1 0.79176(18) 0.6934(2) 0.27426(5) 0.0213(4) Uani d . 1 . .
H H1 0.7242 0.7397 0.2836 0.026 Uiso calc R 1 . .
C C2 0.83983(19) 0.7353(2) 0.24449(5) 0.0220(4) Uani d . 1 . .
H H2 0.8051 0.8096 0.2340 0.026 Uiso calc R 1 . .
C C3 0.94058(19) 0.6659(2) 0.23015(5) 0.0198(4) Uani d . 1 . .
C C4 0.9958(2) 0.5589(2) 0.24676(5) 0.0224(4) Uani d . 1 . .
H H4 1.0655 0.5149 0.2378 0.027 Uiso calc R 1 . .
C C5 0.94723(18) 0.5179(2) 0.27665(5) 0.0219(4) Uani d . 1 . .
H H5 0.9847 0.4463 0.2875 0.026 Uiso calc R 1 . .
C C6 0.84262(18) 0.5826(2) 0.29070(4) 0.0193(4) Uani d . 1 . .
C C7 0.77760(18) 0.5307(2) 0.32020(4) 0.0189(4) Uani d . 1 . .
C C8 0.84031(19) 0.4306(2) 0.34137(4) 0.0206(4) Uani d . 1 . .
H H8 0.9248 0.4078 0.3377 0.025 Uiso calc R 1 . .
C C9 0.77621(19) 0.3725(2) 0.36590(4) 0.0204(4) Uani d . 1 . .
H H9 0.6932 0.4018 0.3690 0.024 Uiso calc R 1 . .
C C10 0.82043(18) 0.2687(2) 0.38841(4) 0.0204(4) Uani d . 1 . .
C C11 0.94097(18) 0.2090(2) 0.38649(5) 0.0216(4) Uani d . 1 . .
H H11 0.9981 0.2378 0.3706 0.026 Uiso calc R 1 . .
C C12 0.97590(19) 0.1086(2) 0.40773(5) 0.0222(5) Uani d . 1 . .
H H12 1.0560 0.0698 0.4059 0.027 Uiso calc R 1 . .
C C13 0.89207(19) 0.0645(2) 0.43198(4) 0.0201(4) Uani d . 1 . .
C C14 0.77209(18) 0.1205(2) 0.43435(5) 0.0213(4) Uani d . 1 . .
H H14 0.7153 0.0914 0.4503 0.026 Uiso calc R 1 . .
C C15 0.73770(19) 0.2212(2) 0.41247(4) 0.0223(4) Uani d . 1 . .
H H15 0.6567 0.2581 0.4139 0.027 Uiso calc R 1 . .
C C16 0.85615(19) -0.0838(2) 0.47766(5) 0.0223(5) Uani d . 1 . .
H H16A 0.7759 -0.1141 0.4686 0.027 Uiso calc R 1 . .
H H16B 0.8391 -0.0130 0.4933 0.027 Uiso calc R 1 . .
C C17 0.92412(19) -0.1985(2) 0.49413(5) 0.0226(5) Uani d . 1 . .
H H17A 1.0055 -0.1674 0.5023 0.027 Uiso calc R 1 . .
H H17B 0.9403 -0.2684 0.4782 0.027 Uiso calc R 1 . .
C C18 0.84727(19) -0.2561(2) 0.52231(5) 0.0241(5) Uani d . 1 . .
H H18A 0.7647 -0.2837 0.5142 0.029 Uiso calc R 1 . .
H H18B 0.8337 -0.1867 0.5386 0.029 Uiso calc R 1 . .
C C19 0.91156(19) -0.3754(2) 0.53860(5) 0.0245(5) Uani d . 1 . .
H H19A 0.9968 -0.3496 0.5451 0.029 Uiso calc R 1 . .
H H19B 0.9190 -0.4472 0.5227 0.029 Uiso calc R 1 . .
C C20 0.84121(19) -0.4277(2) 0.56855(5) 0.0246(5) Uani d . 1 . .
H H20A 0.8313 -0.3552 0.5842 0.030 Uiso calc R 1 . .
H H20B 0.7569 -0.4565 0.5620 0.030 Uiso calc R 1 . .
C C21 0.9087(2) -0.5439(2) 0.58526(5) 0.0260(5) Uani d . 1 . .
H H21A 0.9129 -0.6187 0.5701 0.031 Uiso calc R 1 . .
H H21B 0.9951 -0.5172 0.5903 0.031 Uiso calc R 1 . .
C C22 0.8444(2) -0.5903(2) 0.61656(5) 0.0282(5) Uani d . 1 . .
H H22A 0.8427 -0.5161 0.6319 0.034 Uiso calc R 1 . .
H H22B 0.7570 -0.6136 0.6116 0.034 Uiso calc R 1 . .
C C23 0.90728(19) -0.7093(2) 0.63310(5) 0.0266(5) Uani d . 1 . .
H H23A 0.9130 -0.7823 0.6175 0.032 Uiso calc R 1 . .
H H23B 0.9932 -0.6846 0.6393 0.032 Uiso calc R 1 . .
C C24 0.8373(2) -0.7579(2) 0.66318(5) 0.0347(6) Uani d . 1 . .
H H24A 0.7505 -0.7799 0.6572 0.042 Uiso calc R 1 . .
H H24B 0.8342 -0.6861 0.6792 0.042 Uiso calc R 1 . .
C C25 0.8993(2) -0.8805(3) 0.67877(6) 0.0446(7) Uani d . 1 . .
H H25A 0.8492 -0.9095 0.6971 0.067 Uiso calc R 1 . .
H H25B 0.9833 -0.8577 0.6861 0.067 Uiso calc R 1 . .
H H25C 0.9043 -0.9513 0.6629 0.067 Uiso calc R 1 . .
H H1O1 1.046(3) 0.654(3) 0.1909(7) 0.078(10) 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 0.0000 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O1 H1O1 . . 115.1(18) ?
C13 O3 C16 . . 117.84(15) ?
C2 C1 C6 . . 121.44(19) ?
C2 C1 H1 . . 119.3 ?
C6 C1 H1 . . 119.3 ?
C1 C2 C3 . . 119.77(19) ?
C1 C2 H2 . . 120.1 ?
C3 C2 H2 . . 120.1 ?
O1 C3 C4 . . 122.77(18) ?
O1 C3 C2 . . 117.63(18) ?
C4 C3 C2 . . 119.60(18) ?
C5 C4 C3 . . 120.12(19) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C4 C5 C6 . . 121.03(19) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C5 C6 C1 . . 117.92(18) ?
C5 C6 C7 . . 122.43(18) ?
C1 C6 C7 . . 119.38(17) ?
O2 C7 C8 . . 119.34(17) ?
O2 C7 C6 . . 120.14(18) ?
C8 C7 C6 . . 120.48(17) ?
C9 C8 C7 . . 120.40(18) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C8 C9 C10 . . 128.13(19) ?
C8 C9 H9 . . 115.9 ?
C10 C9 H9 . . 115.9 ?
C15 C10 C11 . . 117.26(18) ?
C15 C10 C9 . . 119.05(18) ?
C11 C10 C9 . . 123.63(18) ?
C12 C11 C10 . . 121.05(18) ?
C12 C11 H11 . . 119.5 ?
C10 C11 H11 . . 119.5 ?
C11 C12 C13 . . 120.53(19) ?
C11 C12 H12 . . 119.7 ?
C13 C12 H12 . . 119.7 ?
O3 C13 C14 . . 124.86(17) ?
O3 C13 C12 . . 115.28(17) ?
C14 C13 C12 . . 119.86(18) ?
C13 C14 C15 . . 118.92(18) ?
C13 C14 H14 . . 120.5 ?
C15 C14 H14 . . 120.5 ?
C14 C15 C10 . . 122.36(19) ?
C14 C15 H15 . . 118.8 ?
C10 C15 H15 . . 118.8 ?
O3 C16 C17 . . 107.35(15) ?
O3 C16 H16A . . 110.2 ?
C17 C16 H16A . . 110.2 ?
O3 C16 H16B . . 110.2 ?
C17 C16 H16B . . 110.2 ?
H16A C16 H16B . . 108.5 ?
C16 C17 C18 . . 111.91(17) ?
C16 C17 H17A . . 109.2 ?
C18 C17 H17A . . 109.2 ?
C16 C17 H17B . . 109.2 ?
C18 C17 H17B . . 109.2 ?
H17A C17 H17B . . 107.9 ?
C17 C18 C19 . . 113.01(17) ?
C17 C18 H18A . . 109.0 ?
C19 C18 H18A . . 109.0 ?
C17 C18 H18B . . 109.0 ?
C19 C18 H18B . . 109.0 ?
H18A C18 H18B . . 107.8 ?
C18 C19 C20 . . 113.81(17) ?
C18 C19 H19A . . 108.8 ?
C20 C19 H19A . . 108.8 ?
C18 C19 H19B . . 108.8 ?
C20 C19 H19B . . 108.8 ?
H19A C19 H19B . . 107.7 ?
C21 C20 C19 . . 113.30(17) ?
C21 C20 H20A . . 108.9 ?
C19 C20 H20A . . 108.9 ?
C21 C20 H20B . . 108.9 ?
C19 C20 H20B . . 108.9 ?
H20A C20 H20B . . 107.7 ?
C22 C21 C20 . . 113.74(17) ?
C22 C21 H21A . . 108.8 ?
C20 C21 H21A . . 108.8 ?
C22 C21 H21B . . 108.8 ?
C20 C21 H21B . . 108.8 ?
H21A C21 H21B . . 107.7 ?
C23 C22 C21 . . 114.78(17) ?
C23 C22 H22A . . 108.6 ?
C21 C22 H22A . . 108.6 ?
C23 C22 H22B . . 108.6 ?
C21 C22 H22B . . 108.6 ?
H22A C22 H22B . . 107.5 ?
C24 C23 C22 . . 113.59(18) ?
C24 C23 H23A . . 108.8 ?
C22 C23 H23A . . 108.8 ?
C24 C23 H23B . . 108.8 ?
C22 C23 H23B . . 108.8 ?
H23A C23 H23B . . 107.7 ?
C23 C24 C25 . . 112.84(19) ?
C23 C24 H24A . . 109.0 ?
C25 C24 H24A . . 109.0 ?
C23 C24 H24B . . 109.0 ?
C25 C24 H24B . . 109.0 ?
H24A C24 H24B . . 107.8 ?
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 C3 . 1.354(2) ?
O1 H1O1 . 0.94(3) ?
O2 C7 . 1.239(2) ?
O3 C13 . 1.373(2) ?
O3 C16 . 1.443(2) ?
C1 C2 . 1.382(3) ?
C1 C6 . 1.400(3) ?
C1 H1 . 0.93 ?
C2 C3 . 1.395(3) ?
C2 H2 . 0.93 ?
C3 C4 . 1.392(3) ?
C4 C5 . 1.385(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.399(3) ?
C5 H5 . 0.93 ?
C6 C7 . 1.479(3) ?
C7 C8 . 1.477(3) ?
C8 C9 . 1.340(3) ?
C8 H8 . 0.93 ?
C9 C10 . 1.461(3) ?
C9 H9 . 0.93 ?
C10 C15 . 1.396(3) ?
C10 C11 . 1.403(3) ?
C11 C12 . 1.376(3) ?
C11 H11 . 0.93 ?
C12 C13 . 1.397(3) ?
C12 H12 . 0.93 ?
C13 C14 . 1.384(3) ?
C14 C15 . 1.393(3) ?
C14 H14 . 0.93 ?
C15 H15 . 0.93 ?
C16 C17 . 1.508(3) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 C18 . 1.520(3) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
C18 C19 . 1.522(3) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 C20 . 1.522(3) ?
C19 H19A . 0.97 ?
C19 H19B . 0.97 ?
C20 C21 . 1.522(3) ?
C20 H20A . 0.97 ?
C20 H20B . 0.97 ?
C21 C22 . 1.518(3) ?
C21 H21A . 0.97 ?
C21 H21B . 0.97 ?
C22 C23 . 1.518(3) ?
C22 H22A . 0.97 ?
C22 H22B . 0.97 ?
C23 C24 . 1.513(3) ?
C23 H23A . 0.97 ?
C23 H23B . 0.97 ?
C24 C25 . 1.526(3) ?
C24 H24A . 0.97 ?
C24 H24B . 0.97 ?
C25 H25A . 0.96 ?
C25 H25B . 0.96 ?
C25 H25C . 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
O1 H1O1 O2 6_656 0.95(3) 1.71(3) 2.655(2) 177(3) yes
C5 H5 O1 3_745 0.93 2.48 3.340(2) 155 yes
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
C6 C1 C2 C3 . . . . 0.5(3) ?
C1 C2 C3 O1 . . . . 176.56(18) ?
C1 C2 C3 C4 . . . . -3.1(3) ?
O1 C3 C4 C5 . . . . -176.75(18) ?
C2 C3 C4 C5 . . . . 2.9(3) ?
C3 C4 C5 C6 . . . . -0.1(3) ?
C4 C5 C6 C1 . . . . -2.5(3) ?
C4 C5 C6 C7 . . . . 171.60(18) ?
C2 C1 C6 C5 . . . . 2.3(3) ?
C2 C1 C6 C7 . . . . -171.99(18) ?
C5 C6 C7 O2 . . . . -160.79(19) ?
C1 C6 C7 O2 . . . . 13.2(3) ?
C5 C6 C7 C8 . . . . 17.0(3) ?
C1 C6 C7 C8 . . . . -168.94(18) ?
O2 C7 C8 C9 . . . . 5.4(3) ?
C6 C7 C8 C9 . . . . -172.41(18) ?
C7 C8 C9 C10 . . . . 177.52(18) ?
C8 C9 C10 C15 . . . . -179.9(2) ?
C8 C9 C10 C11 . . . . -2.7(3) ?
C15 C10 C11 C12 . . . . -0.6(3) ?
C9 C10 C11 C12 . . . . -177.86(19) ?
C10 C11 C12 C13 . . . . -0.6(3) ?
C16 O3 C13 C14 . . . . -1.2(3) ?
C16 O3 C13 C12 . . . . 179.30(17) ?
C11 C12 C13 O3 . . . . -179.39(17) ?
C11 C12 C13 C14 . . . . 1.1(3) ?
O3 C13 C14 C15 . . . . -179.93(18) ?
C12 C13 C14 C15 . . . . -0.5(3) ?
C13 C14 C15 C10 . . . . -0.7(3) ?
C11 C10 C15 C14 . . . . 1.2(3) ?
C9 C10 C15 C14 . . . . 178.62(19) ?
C13 O3 C16 C17 . . . . 175.86(16) ?
O3 C16 C17 C18 . . . . 178.90(16) ?
C16 C17 C18 C19 . . . . 177.92(17) ?
C17 C18 C19 C20 . . . . 175.44(17) ?
C18 C19 C20 C21 . . . . -178.11(18) ?
C19 C20 C21 C22 . . . . 175.79(18) ?
C20 C21 C22 C23 . . . . 177.99(18) ?
C21 C22 C23 C24 . . . . -176.90(19) ?
C22 C23 C24 C25 . . . . 178.0(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742206
