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#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/90/2229062.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_2229062
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Yeap, Chin Sing'
'Prasad, D. Jagadeesh'
'Nayak, Suresh P.'
'Laxmana, K.'
_publ_section_title
;
 (E)-3-(4-Chlorophenyl)-1-(2,3,4-trichlorophenyl)prop-2-en-1-one
;
_journal_coeditor_code           HB5777
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o241
_journal_paper_doi               10.1107/S1600536810053213
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H8 Cl4 O'
_chemical_formula_moiety         'C15 H8 Cl4 O'
_chemical_formula_sum            'C15 H8 Cl4 O'
_chemical_formula_weight         346.01
_chemical_name_systematic
;
(E)-3-(4-Chlorophenyl)-1-(2,3,4-trichlorophenyl)prop-2-en-1-one
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.620(2)
_cell_angle_beta                 96.177(2)
_cell_angle_gamma                92.017(2)
_cell_formula_units_Z            1
_cell_length_a                   3.8879(2)
_cell_length_b                   6.7510(3)
_cell_length_c                   13.7788(5)
_cell_measurement_reflns_used    5499
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      3.00
_cell_volume                     355.93(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7510
_diffrn_reflns_theta_full        29.97
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         1.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_T_max  0.8368
_exptl_absorpt_correction_T_min  0.5735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             174
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.178
_refine_ls_abs_structure_details 'Flack (1983), 1324 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0303
_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)+(0.0435P)²+0.0513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0823
_reflns_number_gt                3183
_reflns_number_total             3395
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5777.cif
_cod_data_source_block           I
_cod_database_code               2229062
_cod_database_fobs_code          2229062
loop_
_symmetry_equiv_pos_as_xyz
'x, y, 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
Cl Cl1 0.18842(18) 1.21292(10) -0.08423(5) 0.05987(19) Uani d . 1 . .
Cl Cl2 1.09977(14) 0.85687(8) 0.46292(4) 0.04498(14) Uani d . 1 . .
Cl Cl3 0.99789(19) 0.85943(10) 0.68403(5) 0.05664(17) Uani d . 1 . .
Cl Cl4 0.67317(19) 0.47391(11) 0.75284(5) 0.0645(2) Uani d . 1 . .
O O1 0.9846(5) 0.3188(3) 0.28530(12) 0.0512(4) Uani d . 1 . .
C C1 0.5993(6) 0.7313(4) 0.00979(16) 0.0407(5) Uani d . 1 . .
H H1A 0.6920 0.6148 -0.0180 0.049 Uiso calc R 1 . .
C C2 0.4793(7) 0.8687(4) -0.05019(16) 0.0445(5) Uani d . 1 . .
H H2A 0.4894 0.8451 -0.1178 0.053 Uiso calc R 1 . .
C C3 0.3445(6) 1.0413(4) -0.00805(17) 0.0399(5) Uani d . 1 . .
C C4 0.3247(6) 1.0802(4) 0.09119(18) 0.0428(5) Uani d . 1 . .
H H4A 0.2311 1.1973 0.1179 0.051 Uiso calc R 1 . .
C C5 0.4465(6) 0.9424(3) 0.15142(15) 0.0386(5) Uani d . 1 . .
H H5A 0.4366 0.9685 0.2190 0.046 Uiso calc R 1 . .
C C6 0.5836(5) 0.7650(3) 0.11160(14) 0.0336(4) Uani d . 1 . .
C C7 0.7206(6) 0.6183(3) 0.17296(15) 0.0369(4) Uani d . 1 . .
H H7A 0.8342 0.5133 0.1418 0.044 Uiso calc R 1 . .
C C8 0.6995(6) 0.6198(3) 0.26870(15) 0.0372(4) Uani d . 1 . .
H H8A 0.5872 0.7226 0.3021 0.045 Uiso calc R 1 . .
C C9 0.8480(6) 0.4641(3) 0.32376(14) 0.0348(4) Uani d . 1 . .
C C10 0.8101(5) 0.4806(3) 0.43238(14) 0.0319(4) Uani d . 1 . .
C C11 0.9116(5) 0.6485(3) 0.50096(15) 0.0309(4) Uani d . 1 . .
C C12 0.8730(6) 0.6515(3) 0.60100(16) 0.0357(4) Uani d . 1 . .
C C13 0.7287(6) 0.4796(4) 0.63117(16) 0.0384(5) Uani d . 1 . .
C C14 0.6308(6) 0.3128(3) 0.56447(18) 0.0432(5) Uani d . 1 . .
H H14A 0.5364 0.1997 0.5856 0.052 Uiso calc R 1 . .
C C15 0.6713(6) 0.3117(3) 0.46607(16) 0.0384(4) Uani d . 1 . .
H H15A 0.6054 0.1972 0.4216 0.046 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 121.0(2) ?
C2 C1 H1A . . 119.5 ?
C6 C1 H1A . . 119.5 ?
C3 C2 C1 . . 118.9(2) ?
C3 C2 H2A . . 120.6 ?
C1 C2 H2A . . 120.6 ?
C4 C3 C2 . . 122.0(2) ?
C4 C3 Cl1 . . 119.28(18) ?
C2 C3 Cl1 . . 118.73(17) ?
C3 C4 C5 . . 119.1(2) ?
C3 C4 H4A . . 120.5 ?
C5 C4 H4A . . 120.5 ?
C4 C5 C6 . . 120.77(19) ?
C4 C5 H5A . . 119.6 ?
C6 C5 H5A . . 119.6 ?
C5 C6 C1 . . 118.25(19) ?
C5 C6 C7 . . 122.28(18) ?
C1 C6 C7 . . 119.43(18) ?
C8 C7 C6 . . 126.72(19) ?
C8 C7 H7A . . 116.6 ?
C6 C7 H7A . . 116.6 ?
C7 C8 C9 . . 122.32(19) ?
C7 C8 H8A . . 118.8 ?
C9 C8 H8A . . 118.8 ?
O1 C9 C8 . . 123.42(18) ?
O1 C9 C10 . . 118.57(18) ?
C8 C9 C10 . . 117.92(17) ?
C11 C10 C15 . . 118.23(18) ?
C11 C10 C9 . . 124.79(18) ?
C15 C10 C9 . . 116.95(19) ?
C10 C11 C12 . . 121.51(18) ?
C10 C11 Cl2 . . 119.60(14) ?
C12 C11 Cl2 . . 118.87(16) ?
C11 C12 C13 . . 118.2(2) ?
C11 C12 Cl3 . . 120.83(17) ?
C13 C12 Cl3 . . 120.94(16) ?
C14 C13 C12 . . 120.76(19) ?
C14 C13 Cl4 . . 118.73(17) ?
C12 C13 Cl4 . . 120.51(18) ?
C13 C14 C15 . . 120.4(2) ?
C13 C14 H14A . . 119.8 ?
C15 C14 H14A . . 119.8 ?
C14 C15 C10 . . 120.9(2) ?
C14 C15 H15A . . 119.6 ?
C10 C15 H15A . . 119.6 ?
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
Cl1 C3 . 1.745(2) ?
Cl2 C11 . 1.730(2) ?
Cl3 C12 . 1.709(2) ?
Cl4 C13 . 1.718(2) ?
O1 C9 . 1.218(3) ?
C1 C2 . 1.383(3) ?
C1 C6 . 1.399(3) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.378(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.369(3) ?
C4 C5 . 1.389(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.398(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.463(3) ?
C7 C8 . 1.329(3) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.474(3) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.509(3) ?
C10 C11 . 1.392(3) ?
C10 C15 . 1.399(3) ?
C11 C12 . 1.400(3) ?
C12 C13 . 1.403(3) ?
C13 C14 . 1.370(4) ?
C14 C15 . 1.381(3) ?
C14 H14A . 0.9300 ?
C15 H15A . 0.9300 ?
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 . . . . 0.4(4) ?
C1 C2 C3 C4 . . . . -0.3(4) ?
C1 C2 C3 Cl1 . . . . -179.2(2) ?
C2 C3 C4 C5 . . . . 0.5(4) ?
Cl1 C3 C4 C5 . . . . 179.44(19) ?
C3 C4 C5 C6 . . . . -0.8(4) ?
C4 C5 C6 C1 . . . . 0.9(3) ?
C4 C5 C6 C7 . . . . 178.7(2) ?
C2 C1 C6 C5 . . . . -0.7(3) ?
C2 C1 C6 C7 . . . . -178.6(2) ?
C5 C6 C7 C8 . . . . 8.2(4) ?
C1 C6 C7 C8 . . . . -174.0(2) ?
C6 C7 C8 C9 . . . . -179.9(2) ?
C7 C8 C9 O1 . . . . -3.7(4) ?
C7 C8 C9 C10 . . . . 179.8(2) ?
O1 C9 C10 C11 . . . . 129.4(2) ?
C8 C9 C10 C11 . . . . -53.9(3) ?
O1 C9 C10 C15 . . . . -48.7(3) ?
C8 C9 C10 C15 . . . . 127.9(2) ?
C15 C10 C11 C12 . . . . -0.9(3) ?
C9 C10 C11 C12 . . . . -178.96(19) ?
C15 C10 C11 Cl2 . . . . 177.53(17) ?
C9 C10 C11 Cl2 . . . . -0.6(3) ?
C10 C11 C12 C13 . . . . 0.1(3) ?
Cl2 C11 C12 C13 . . . . -178.29(16) ?
C10 C11 C12 Cl3 . . . . -179.78(17) ?
Cl2 C11 C12 Cl3 . . . . 1.8(2) ?
C11 C12 C13 C14 . . . . 0.5(3) ?
Cl3 C12 C13 C14 . . . . -179.62(19) ?
C11 C12 C13 Cl4 . . . . -179.80(16) ?
Cl3 C12 C13 Cl4 . . . . 0.1(3) ?
C12 C13 C14 C15 . . . . -0.3(3) ?
Cl4 C13 C14 C15 . . . . 179.98(19) ?
C13 C14 C15 C10 . . . . -0.5(4) ?
C11 C10 C15 C14 . . . . 1.1(3) ?
C9 C10 C15 C14 . . . . 179.3(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 6254370
2 PubChem 7947994
