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#$Date: 2023-02-13 11:24:35 +0200 (Mon, 13 Feb 2023) $
#$Revision: 280870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106766.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_8106766
loop_
_publ_author_name
'Maluleka, Marole M.'
'Mphahlele, Malose J.'
_publ_section_title
;
 Crystal structure of (1E,4E)-1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one,
 C17H12Cl2O
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1049
_journal_page_last               1050
_journal_paper_doi               10.1515/ncrs-2017-0212
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C17 H12 Cl2 O'
_chemical_formula_sum            'C17 H12 Cl2 O'
_chemical_formula_weight         303.17
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 99.088(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.2845(14)
_cell_length_b                   14.2007(11)
_cell_length_c                   5.8795(5)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    263(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      3.58
_cell_measurement_wavelength     0.71073
_cell_volume                     1425.0(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX3 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      263(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            42558
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_min         2.785
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_T_max  0.9569
_exptl_absorpt_correction_T_min  0.8639
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 1999)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.393
_exptl_crystal_size_min          0.178
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0354P)²+1.2982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1395
_reflns_Friedel_coverage         0
_reflns_number_gt                2804
_reflns_number_total             3435
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0212_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106766
_shelx_estimated_absorpt_t_min   0.819
_shelx_estimated_absorpt_t_max   0.925
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_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 0.61986(13) 0.12231(15) 0.2819(4) 0.0380(5) Uani 1 1 d . . . . .
C2 C 0.68207(14) 0.16086(16) 0.1870(4) 0.0429(5) Uani 1 1 d . . . . .
H2 H 0.6723 0.1887 0.0421 0.051 Uiso 1 1 calc R U . . .
C3 C 0.75795(14) 0.15824(17) 0.3055(4) 0.0470(6) Uani 1 1 d . . . . .
H3 H 0.7992 0.1832 0.2407 0.056 Uiso 1 1 calc R U . . .
C4 C 0.77126(14) 0.11781(17) 0.5218(4) 0.0462(5) Uani 1 1 d . . . . .
C5 C 0.71169(16) 0.07918(17) 0.6194(4) 0.0481(6) Uani 1 1 d . . . . .
H5 H 0.7219 0.0517 0.7646 0.058 Uiso 1 1 calc R U . . .
C6 C 0.63620(15) 0.08159(17) 0.4990(4) 0.0456(5) Uani 1 1 d . . . . .
H6 H 0.5956 0.0554 0.5646 0.055 Uiso 1 1 calc R U . . .
C7 C 0.53826(14) 0.12290(16) 0.1603(4) 0.0428(5) Uani 1 1 d . . . . .
H7 H 0.4995 0.1062 0.2461 0.051 Uiso 1 1 calc R U . . .
C8 C 0.51484(14) 0.14464(18) -0.0575(4) 0.0461(6) Uani 1 1 d . . . . .
H8 H 0.5526 0.1665 -0.1411 0.055 Uiso 1 1 calc R U . . .
C9 C 0.43368(14) 0.13719(17) -0.1798(4) 0.0445(5) Uani 1 1 d . . . . .
C10 C 0.36899(14) 0.13437(17) -0.0432(4) 0.0445(5) Uani 1 1 d . . . . .
H10 H 0.3791 0.1501 0.1122 0.053 Uiso 1 1 calc R U . . .
C11 C 0.29709(13) 0.11013(16) -0.1362(4) 0.0389(5) Uani 1 1 d . . . . .
H11 H 0.2907 0.0883 -0.2871 0.047 Uiso 1 1 calc R U . . .
C12 C 0.22634(13) 0.11380(15) -0.0283(4) 0.0357(4) Uani 1 1 d . . . . .
C13 C 0.15572(13) 0.08123(16) -0.1481(4) 0.0404(5) Uani 1 1 d . . . . .
H13 H 0.155 0.0528 -0.2908 0.049 Uiso 1 1 calc R U . . .
C14 C 0.08632(14) 0.09002(17) -0.0603(4) 0.0452(5) Uani 1 1 d . . . . .
H14 H 0.0395 0.0683 -0.1434 0.054 Uiso 1 1 calc R U . . .
C15 C 0.08789(13) 0.13147(17) 0.1517(4) 0.0415(5) Uani 1 1 d . . . . .
C16 C 0.15760(14) 0.16321(16) 0.2785(4) 0.0399(5) Uani 1 1 d . . . . .
H16 H 0.158 0.1904 0.4225 0.048 Uiso 1 1 calc R U . . .
C17 C 0.22622(13) 0.15406(15) 0.1892(4) 0.0387(5) Uani 1 1 d . . . . .
H17 H 0.273 0.1749 0.2744 0.046 Uiso 1 1 calc R U . . .
O1 O 0.42181(11) 0.13427(15) -0.3897(3) 0.0605(5) Uani 1 1 d . . . . .
Cl1 Cl 0.00210(4) 0.14457(6) 0.26720(14) 0.0703(3) Uani 1 1 d . . . . .
Cl2 Cl 0.86568(5) 0.11711(7) 0.67445(15) 0.0759(3) Uani 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 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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 118.1(2) . .
C6 C1 C7 119.2(2) . .
C2 C1 C7 122.7(2) . .
C3 C2 C1 121.0(2) . .
C3 C2 H2 119.5 . .
C1 C2 H2 119.5 . .
C4 C3 C2 118.8(2) . .
C4 C3 H3 120.6 . .
C2 C3 H3 120.6 . .
C5 C4 C3 121.7(2) . .
C5 C4 Cl2 119.29(19) . .
C3 C4 Cl2 119.0(2) . .
C4 C5 C6 119.1(2) . .
C4 C5 H5 120.5 . .
C6 C5 H5 120.5 . .
C5 C6 C1 121.3(2) . .
C5 C6 H6 119.4 . .
C1 C6 H6 119.4 . .
C8 C7 C1 126.5(2) . .
C8 C7 H7 116.7 . .
C1 C7 H7 116.7 . .
C7 C8 C9 125.4(2) . .
C7 C8 H8 117.3 . .
C9 C8 H8 117.3 . .
O1 C9 C8 119.4(2) . .
O1 C9 C10 121.9(2) . .
C8 C9 C10 118.7(2) . .
C11 C10 C9 121.7(2) . .
C11 C10 H10 119.1 . .
C9 C10 H10 119.1 . .
C10 C11 C12 127.3(2) . .
C10 C11 H11 116.3 . .
C12 C11 H11 116.3 . .
C13 C12 C17 118.1(2) . .
C13 C12 C11 119.74(19) . .
C17 C12 C11 122.1(2) . .
C14 C13 C12 121.7(2) . .
C14 C13 H13 119.2 . .
C12 C13 H13 119.2 . .
C15 C14 C13 118.8(2) . .
C15 C14 H14 120.6 . .
C13 C14 H14 120.6 . .
C14 C15 C16 121.1(2) . .
C14 C15 Cl1 120.32(18) . .
C16 C15 Cl1 118.56(18) . .
C17 C16 C15 119.5(2) . .
C17 C16 H16 120.3 . .
C15 C16 H16 120.3 . .
C16 C17 C12 120.8(2) . .
C16 C17 H17 119.6 . .
C12 C17 H17 119.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.389(3) .
C1 C2 1.399(3) .
C1 C7 1.477(3) .
C2 C3 1.385(3) .
C2 H2 0.93 .
C3 C4 1.381(3) .
C3 H3 0.93 .
C4 C5 1.370(4) .
C4 Cl2 1.734(3) .
C5 C6 1.383(4) .
C5 H5 0.93 .
C6 H6 0.93 .
C7 C8 1.317(3) .
C7 H7 0.93 .
C8 C9 1.476(3) .
C8 H8 0.93 .
C9 O1 1.220(3) .
C9 C10 1.476(3) .
C10 C11 1.322(3) .
C10 H10 0.93 .
C11 C12 1.464(3) .
C11 H11 0.93 .
C12 C13 1.389(3) .
C12 C17 1.402(3) .
C13 C14 1.384(3) .
C13 H13 0.93 .
C14 C15 1.375(3) .
C14 H14 0.93 .
C15 C16 1.388(3) .
C15 Cl1 1.736(2) .
C16 C17 1.377(3) .
C16 H16 0.93 .
C17 H17 0.93 .
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 0.3(3) . . . .
C7 C1 C2 C3 -179.4(2) . . . .
C1 C2 C3 C4 -0.9(4) . . . .
C2 C3 C4 C5 1.1(4) . . . .
C2 C3 C4 Cl2 -178.28(19) . . . .
C3 C4 C5 C6 -0.6(4) . . . .
Cl2 C4 C5 C6 178.70(18) . . . .
C4 C5 C6 C1 0.0(4) . . . .
C2 C1 C6 C5 0.2(3) . . . .
C7 C1 C6 C5 179.9(2) . . . .
C6 C1 C7 C8 -168.4(2) . . . .
C2 C1 C7 C8 11.2(4) . . . .
C1 C7 C8 C9 174.7(2) . . . .
C7 C8 C9 O1 -160.2(3) . . . .
C7 C8 C9 C10 20.3(4) . . . .
O1 C9 C10 C11 13.6(4) . . . .
C8 C9 C10 C11 -167.0(2) . . . .
C9 C10 C11 C12 -173.1(2) . . . .
C10 C11 C12 C13 -176.9(2) . . . .
C10 C11 C12 C17 6.6(4) . . . .
C17 C12 C13 C14 1.7(3) . . . .
C11 C12 C13 C14 -174.9(2) . . . .
C12 C13 C14 C15 -0.5(4) . . . .
C13 C14 C15 C16 -0.7(4) . . . .
C13 C14 C15 Cl1 179.58(19) . . . .
C14 C15 C16 C17 0.8(4) . . . .
Cl1 C15 C16 C17 -179.55(18) . . . .
C15 C16 C17 C12 0.5(3) . . . .
C13 C12 C17 C16 -1.7(3) . . . .
C11 C12 C17 C16 174.9(2) . . . .
