#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/67/2206799.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_2206799
loop_
_publ_author_name
'Lei Wang'
'Wen Yang'
'De-Chun Zhang'
_publ_section_title
;
1,3-Bis(4-chlorophenyl)prop-2-en-1-one
;
_journal_coeditor_code           TK6238
_journal_issue                   9
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o2820
_journal_page_last               2822
_journal_paper_doi               10.1107/S1600536805024566
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C15 H10 Cl2 O'
_chemical_formula_moiety         'C15 H10 Cl2 O'
_chemical_formula_sum            'C15 H10 Cl2 O'
_chemical_formula_weight         277.13
_chemical_melting_point          .428E-305
_chemical_name_systematic
;
1,3-Bis(4-chlorophenyl)prop-2-en-1-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 92.908(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.325(3)
_cell_length_b                   14.009(2)
_cell_length_c                   5.8501(10)
_cell_measurement_reflns_used    4017
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      3.0
_cell_volume                     1254.3(4)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalStructure (Rigaku, 2000)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_av_sigmaI/netI    0.030
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            12957
_diffrn_reflns_theta_full        26.4
_diffrn_reflns_theta_max         26.4
_diffrn_reflns_theta_min         3.0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Jacobson, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.15
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.15
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_gt           0.048
_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)+(0.0351P)²+0.6039P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.098
_refine_ls_wR_factor_ref         0.105
_reflns_number_gt                2109
_reflns_number_total             2549
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk6238.cif
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206799
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_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
Cl1 0.13688(4) 0.87551(5) 0.24181(12) 0.0520(2) Uani d . 1 Cl
Cl2 0.98538(4) 0.85574(5) 0.76034(11) 0.0515(2) Uani d . 1 Cl
O1 0.52958(11) 0.87320(13) -0.1987(3) 0.0462(4) Uani d . 1 O
C1 0.41966(14) 0.87436(14) 0.0693(4) 0.0293(5) Uani d . 1 C
C2 0.39509(14) 0.90720(15) 0.2824(4) 0.0325(5) Uani d . 1 C
H2 0.4385 0.9277 0.3934 0.039 Uiso calc R 1 H
C3 0.30778(15) 0.90992(15) 0.3322(4) 0.0351(5) Uani d . 1 C
H3 0.2908 0.9341 0.4751 0.042 Uiso calc R 1 H
C4 0.24574(14) 0.87724(15) 0.1726(4) 0.0332(5) Uani d . 1 C
C5 0.26815(14) 0.84412(15) -0.0390(4) 0.0344(5) Uani d . 1 C
H5 0.2245 0.8222 -0.1477 0.041 Uiso calc R 1 H
C6 0.35493(14) 0.84341(14) -0.0895(4) 0.0321(5) Uani d . 1 C
H6 0.3710 0.8214 -0.2352 0.039 Uiso calc R 1 H
C7 0.74095(13) 0.88928(14) 0.3031(3) 0.0283(5) Uani d . 1 C
C8 0.82155(14) 0.92138(15) 0.2331(4) 0.0334(5) Uani d . 1 C
H8 0.8247 0.9503 0.0868 0.040 Uiso calc R 1 H
C9 0.89706(15) 0.91220(16) 0.3713(4) 0.0370(5) Uani d . 1 C
H9 0.9514 0.9345 0.3211 0.044 Uiso calc R 1 H
C10 0.89194(14) 0.87001(15) 0.5835(4) 0.0336(5) Uani d . 1 C
C11 0.81306(14) 0.83811(15) 0.6594(4) 0.0331(5) Uani d . 1 C
H11 0.8106 0.8093 0.8060 0.040 Uiso calc R 1 H
C12 0.73804(14) 0.84827(14) 0.5214(4) 0.0306(5) Uani d . 1 C
H12 0.6837 0.8273 0.5746 0.037 Uiso calc R 1 H
C13 0.51247(14) 0.87384(15) 0.0047(4) 0.0332(5) Uani d . 1 C
C14 0.58259(14) 0.87272(15) 0.1879(4) 0.0326(5) Uani d . 1 C
H14 0.5688 0.8556 0.3391 0.039 Uiso calc R 1 H
C15 0.66429(14) 0.89506(14) 0.1455(4) 0.0308(5) Uani d . 1 C
H15 0.6740 0.9173 -0.0045 0.037 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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C6 C1 C2 118.8(2) y
C6 C1 C13 119.05(19) y
C2 C1 C13 122.11(19) y
C3 C2 C1 120.3(2) ?
C3 C2 H2 119.9 ?
C1 C2 H2 119.9 ?
C4 C3 C2 119.31(19) ?
C4 C3 H3 120.3 ?
C2 C3 H3 120.3 ?
C3 C4 C5 121.7(2) y
C3 C4 Cl1 119.00(17) y
C5 C4 Cl1 119.31(17) y
C6 C5 C4 118.8(2) ?
C6 C5 H5 120.6 ?
C4 C5 H5 120.6 ?
C5 C6 C1 121.15(19) ?
C5 C6 H6 119.4 ?
C1 C6 H6 119.4 ?
C8 C7 C12 117.96(19) y
C8 C7 C15 119.53(18) y
C12 C7 C15 122.44(19) y
C9 C8 C7 121.66(19) ?
C9 C8 H8 119.2 ?
C7 C8 H8 119.2 ?
C10 C9 C8 118.8(2) ?
C10 C9 H9 120.6 ?
C8 C9 H9 120.6 ?
C9 C10 C11 121.2(2) y
C9 C10 Cl2 120.17(17) y
C11 C10 Cl2 118.67(17) y
C12 C11 C10 119.7(2) ?
C12 C11 H11 120.2 ?
C10 C11 H11 120.2 ?
C11 C12 C7 120.76(19) ?
C11 C12 H12 119.6 ?
C7 C12 H12 119.6 ?
O1 C13 C14 121.2(2) y
O1 C13 C1 119.9(2) y
C14 C13 C1 118.95(18) y
C15 C14 C13 121.34(19) y
C15 C14 H14 119.3 ?
C13 C14 H14 119.3 ?
C14 C15 C7 127.33(19) y
C14 C15 H15 116.3 ?
C7 C15 H15 116.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4 1.737(2) y
Cl2 C10 1.735(2) y
O1 C13 1.231(3) y
C1 C6 1.394(3) ?
C1 C2 1.398(3) ?
C1 C13 1.490(3) y
C2 C3 1.384(3) ?
C2 H2 0.9500 ?
C3 C4 1.377(3) ?
C3 H3 0.9500 ?
C4 C5 1.382(3) ?
C5 C6 1.377(3) ?
C5 H5 0.9500 ?
C6 H6 0.9500 ?
C7 C8 1.395(3) ?
C7 C12 1.403(3) ?
C7 C15 1.458(3) y
C8 C9 1.384(3) ?
C8 H8 0.9500 ?
C9 C10 1.381(3) ?
C9 H9 0.9500 ?
C10 C11 1.383(3) ?
C11 C12 1.378(3) ?
C11 H11 0.9500 ?
C12 H12 0.9500 ?
C13 C14 1.479(3) y
C14 C15 1.326(3) y
C14 H14 0.9500 ?
C15 H15 0.9500 ?
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
C2 H2 O1 1_556 0.95 2.81 3.613(3) 143 y
C14 H14 O1 1_556 0.95 2.81 3.719(3) 160 y
C12 H12 O1 1_556 0.95 2.84 3.680(3) 148 y
C9 H9 Cl1 1_655 0.95 3.02 3.825(2) 144 y
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_publ_flag
C6 C1 C2 C3 -0.9(3) ?
C13 C1 C2 C3 177.48(19) y
C1 C2 C3 C4 2.0(3) ?
C2 C3 C4 C5 -1.8(3) ?
C2 C3 C4 Cl1 176.91(16) y
C3 C4 C5 C6 0.5(3) ?
Cl1 C4 C5 C6 -178.24(16) y
C4 C5 C6 C1 0.7(3) ?
C2 C1 C6 C5 -0.5(3) ?
C13 C1 C6 C5 -178.89(19) y
C12 C7 C8 C9 1.0(3) ?
C15 C7 C8 C9 -176.1(2) y
C7 C8 C9 C10 0.1(3) ?
C8 C9 C10 C11 -0.7(3) ?
C8 C9 C10 Cl2 179.14(17) y
C9 C10 C11 C12 0.1(3) ?
Cl2 C10 C11 C12 -179.68(16) y
C10 C11 C12 C7 1.0(3) ?
C8 C7 C12 C11 -1.5(3) ?
C15 C7 C12 C11 175.48(19) y
C6 C1 C13 O1 20.7(3) y
C2 C1 C13 O1 -157.7(2) y
C6 C1 C13 C14 -158.45(19) y
C2 C1 C13 C14 23.2(3) y
O1 C13 C14 C15 17.3(3) y
C1 C13 C14 C15 -163.6(2) y
C13 C14 C15 C7 -174.3(2) y
C8 C7 C15 C14 -176.1(2) y
C12 C7 C15 C14 6.9(3) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654850
