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#$Date: 2023-01-28 10:58:51 +0200 (Sat, 28 Jan 2023) $
#$Revision: 280654 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/66/8106613.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106613
loop_
_publ_author_name
'Köysal, Yavuz'
'Bülbül, Hakan'
'Özdemir, Funda'
'İlhan, İlhan Özer'
'Dege, Necmi'
_publ_section_title
;
 Crystal structure of
 3-(4-methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one, C17H16O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              593
_journal_page_last               594
_journal_paper_doi               10.1515/ncrs-2016-0357
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C17 H16 O2'
_chemical_formula_sum            'C17 H16 O2'
_chemical_formula_weight         252.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_cell_angle_alpha                90
_cell_angle_beta                 115.545(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6963(12)
_cell_length_b                   11.1187(8)
_cell_length_c                   11.6902(10)
_cell_measurement_reflns_used    5744
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.79
_cell_measurement_theta_min      1.83
_cell_volume                     1371.7(2)
_computing_cell_refinement       'X-AREA [13] '
_computing_data_collection       'X-AREA [13]'
_computing_data_reduction        'X-RED32 [13]'
_computing_molecular_graphics    'ORTEP-3 for Windows [16]'
_computing_publication_material  'WinGX [16]'
_computing_structure_refinement  'SHELXL-2014/7 [15]'
_computing_structure_solution    'SHELXS97 [14]'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'w scan'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7194
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.930
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_correction_T_min  0.9711
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'STOE X-RED [13]'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.075
_refine_diff_density_min         -0.097
_refine_diff_density_rms         0.019
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.807
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.807
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0350
_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)+(0.0458P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1375
_reflns_number_total             2661
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0357_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106613
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36180(15) 0.32004(16) 0.61559(16) 0.0787(4) Uani 1 1 d . . . . .
C2 C 0.43587(15) 0.27272(15) 0.73366(16) 0.0788(4) Uani 1 1 d . . . . .
C3 C 0.41923(13) 0.15512(14) 0.75852(14) 0.0729(4) Uani 1 1 d . . . . .
C4 C 0.32929(16) 0.08557(15) 0.66461(16) 0.0814(5) Uani 1 1 d . . . . .
C5 C 0.25615(15) 0.13408(14) 0.54835(16) 0.0749(4) Uani 1 1 d . . . . .
C6 C 0.27015(13) 0.25269(13) 0.52017(13) 0.0660(4) Uani 1 1 d . . . . .
C7 C 0.19122(15) 0.30866(15) 0.39781(15) 0.0740(4) Uani 1 1 d . . . . .
C8 C 0.10143(15) 0.25798(15) 0.29722(15) 0.0734(4) Uani 1 1 d . . . . .
C9 C 0.02624(13) 0.32677(13) 0.18103(13) 0.0704(4) Uani 1 1 d . . . . .
C10 C -0.05096(13) 0.26101(12) 0.06163(13) 0.0662(4) Uani 1 1 d . . . . .
C11 C -0.10413(15) 0.32522(16) -0.05156(16) 0.0763(4) Uani 1 1 d . . . . .
C12 C -0.17460(16) 0.26820(16) -0.16466(16) 0.0798(5) Uani 1 1 d . . . . .
C13 C -0.19631(13) 0.14563(15) -0.17099(14) 0.0730(4) Uani 1 1 d . . . . .
C14 C -0.14285(15) 0.08265(16) -0.05865(16) 0.0779(4) Uani 1 1 d . . . . .
C15 C -0.07184(14) 0.13783(13) 0.05549(17) 0.0746(4) Uani 1 1 d . . . . .
C16 C -0.2733(2) 0.0836(2) -0.2941(2) 0.0986(6) Uani 1 1 d . . . . .
C17 C 0.5723(2) 0.1671(2) 0.9754(2) 0.0991(6) Uani 1 1 d . . . . .
O1 O 0.48553(10) 0.09799(10) 0.87164(10) 0.0952(4) Uani 1 1 d . . . . .
O2 O 0.02810(11) 0.43693(9) 0.18209(9) 0.0926(4) Uani 1 1 d . . . . .
H1 H 0.3737(14) 0.4032(15) 0.5996(13) 0.093(5) Uiso 1 1 d . . . . .
H2 H 0.4969(14) 0.3226(13) 0.7989(14) 0.091(5) Uiso 1 1 d . . . . .
H4 H 0.3196(15) 0.0037(15) 0.6841(14) 0.104(5) Uiso 1 1 d . . . . .
H5 H 0.1935(13) 0.0848(12) 0.4841(13) 0.081(4) Uiso 1 1 d . . . . .
H7 H 0.2070(13) 0.3943(13) 0.3907(12) 0.085(4) Uiso 1 1 d . . . . .
H8 H 0.0821(13) 0.1756(14) 0.2962(12) 0.082(4) Uiso 1 1 d . . . . .
H11 H -0.0863(14) 0.4102(15) -0.0479(14) 0.097(5) Uiso 1 1 d . . . . .
H12 H -0.2063(13) 0.3136(13) -0.2413(14) 0.085(5) Uiso 1 1 d . . . . .
H14 H -0.1552(13) -0.0036(14) -0.0611(13) 0.092(5) Uiso 1 1 d . . . . .
H15 H -0.0377(13) 0.0903(13) 0.1305(13) 0.081(4) Uiso 1 1 d . . . . .
H17A H 0.6045(19) 0.1107(18) 1.048(2) 0.143(8) Uiso 1 1 d . . . . .
H17B H 0.6404(18) 0.2026(17) 0.9546(16) 0.129(7) Uiso 1 1 d . . . . .
H17C H 0.5260(16) 0.2375(17) 0.9895(14) 0.113(6) Uiso 1 1 d . . . . .
H18A H -0.362(2) 0.100(2) -0.325(2) 0.173(10) Uiso 1 1 d . . . . .
H18B H -0.267(2) -0.001(2) -0.290(2) 0.159(9) Uiso 1 1 d . . . . .
H18C H -0.251(2) 0.1087(19) -0.361(2) 0.159(9) Uiso 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C6 122.22(16) . .
C2 C1 H1 118.6(9) . .
C6 C1 H1 119.2(9) . .
C3 C2 C1 119.38(16) . .
C3 C2 H2 120.4(9) . .
C1 C2 H2 120.2(9) . .
O1 C3 C2 125.08(15) . .
O1 C3 C4 115.34(15) . .
C2 C3 C4 119.58(16) . .
C5 C4 C3 120.29(16) . .
C5 C4 H4 121.7(10) . .
C3 C4 H4 118.0(9) . .
C4 C5 C6 121.64(16) . .
C4 C5 H5 119.4(8) . .
C6 C5 H5 119.0(8) . .
C5 C6 C1 116.88(15) . .
C5 C6 C7 123.16(14) . .
C1 C6 C7 119.93(15) . .
C8 C7 C6 127.84(16) . .
C8 C7 H7 116.5(8) . .
C6 C7 H7 115.6(8) . .
C7 C8 C9 121.96(15) . .
C7 C8 H8 121.4(8) . .
C9 C8 H8 116.6(8) . .
O2 C9 C8 120.56(14) . .
O2 C9 C10 120.14(13) . .
C8 C9 C10 119.29(14) . .
C15 C10 C11 117.42(15) . .
C15 C10 C9 123.78(14) . .
C11 C10 C9 118.79(14) . .
C12 C11 C10 120.97(17) . .
C12 C11 H11 121.6(9) . .
C10 C11 H11 117.4(9) . .
C11 C12 C13 121.75(16) . .
C11 C12 H12 119.3(9) . .
C13 C12 H12 118.9(9) . .
C14 C13 C12 116.92(16) . .
C14 C13 C16 121.33(17) . .
C12 C13 C16 121.75(17) . .
C15 C14 C13 122.29(16) . .
C15 C14 H14 119.4(9) . .
C13 C14 H14 118.3(9) . .
C14 C15 C10 120.65(16) . .
C14 C15 H15 118.9(8) . .
C10 C15 H15 120.4(8) . .
C13 C16 H18A 112.2(14) . .
C13 C16 H18B 114.3(14) . .
H18A C16 H18B 105(2) . .
C13 C16 H18C 112.6(13) . .
H18A C16 H18C 105.4(18) . .
H18B C16 H18C 106.2(19) . .
O1 C17 H17A 104.9(12) . .
O1 C17 H17B 110.6(10) . .
H17A C17 H17B 113.9(16) . .
O1 C17 H17C 108.9(9) . .
H17A C17 H17C 112.7(15) . .
H17B C17 H17C 105.9(15) . .
C3 O1 C17 118.13(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.379(2) .
C1 C6 1.387(2) .
C1 H1 0.965(16) .
C2 C3 1.371(2) .
C2 H2 0.964(15) .
C3 O1 1.3672(17) .
C3 C4 1.383(2) .
C4 C5 1.366(2) .
C4 H4 0.957(17) .
C5 C6 1.3859(19) .
C5 H5 0.963(14) .
C6 C7 1.465(2) .
C7 C8 1.318(2) .
C7 H7 0.980(14) .
C8 C9 1.474(2) .
C8 H8 0.942(15) .
C9 O2 1.2250(16) .
C9 C10 1.487(2) .
C10 C15 1.3875(19) .
C10 C11 1.3920(19) .
C11 C12 1.375(2) .
C11 H11 0.965(16) .
C12 C13 1.382(2) .
C12 H12 0.953(14) .
C13 C14 1.378(2) .
C13 C16 1.497(2) .
C14 C15 1.375(2) .
C14 H14 0.969(15) .
C15 H15 0.952(14) .
C16 H18A 0.95(2) .
C16 H18B 0.95(2) .
C16 H18C 0.97(2) .
C17 O1 1.425(2) .
C17 H17A 0.99(2) .
C17 H17B 1.01(2) .
C17 H17C 1.004(18) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 O2 0.965(16) 2.595(16) 3.3591(19) 136.3(11) 3_565
C11 H11 O2 0.965(16) 2.450(14) 2.784(2) 100.0(10) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 0.1(2) . . . .
C1 C2 C3 O1 -179.39(14) . . . .
C1 C2 C3 C4 0.6(2) . . . .
O1 C3 C4 C5 178.99(14) . . . .
C2 C3 C4 C5 -1.0(2) . . . .
C3 C4 C5 C6 0.7(3) . . . .
C4 C5 C6 C1 -0.1(2) . . . .
C4 C5 C6 C7 -178.32(15) . . . .
C2 C1 C6 C5 -0.3(2) . . . .
C2 C1 C6 C7 177.97(14) . . . .
C5 C6 C7 C8 -2.6(2) . . . .
C1 C6 C7 C8 179.23(16) . . . .
C6 C7 C8 C9 177.92(13) . . . .
C7 C8 C9 O2 -13.8(2) . . . .
C7 C8 C9 C10 165.42(14) . . . .
O2 C9 C10 C15 -171.11(14) . . . .
C8 C9 C10 C15 9.6(2) . . . .
O2 C9 C10 C11 10.0(2) . . . .
C8 C9 C10 C11 -169.21(13) . . . .
C15 C10 C11 C12 0.1(2) . . . .
C9 C10 C11 C12 178.99(13) . . . .
C10 C11 C12 C13 0.4(2) . . . .
C11 C12 C13 C14 -0.7(2) . . . .
C11 C12 C13 C16 179.87(17) . . . .
C12 C13 C14 C15 0.6(2) . . . .
C16 C13 C14 C15 -179.99(17) . . . .
C13 C14 C15 C10 -0.1(2) . . . .
C11 C10 C15 C14 -0.2(2) . . . .
C9 C10 C15 C14 -179.05(13) . . . .
C2 C3 O1 C17 5.0(2) . . . .
C4 C3 O1 C17 -174.97(16) . . . .
