#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/80/2218083.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_2218083
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Jebas, Samuel Robinson'
'Patil, P. S.'
'Dharmaprakash, S. M.'
_publ_section_title
;
 1-(2,4-Dichlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one
;
_journal_coeditor_code           CI2584
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o936
_journal_paper_doi               10.1107/S1600536808011008
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C16 H12 Cl2 O'
_chemical_formula_moiety         'C16 H12 Cl2 O'
_chemical_formula_sum            'C16 H12 Cl2 O'
_chemical_formula_weight         291.16
_chemical_name_common
;
1-(2,4-Dichlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one
;
_chemical_name_systematic
;
1-(2,4-Dichlorophenyl)-3-(4-methylphenyl)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                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   12.548500(10)
_cell_length_b                   7.477500(10)
_cell_length_c                   28.7764(3)
_cell_measurement_reflns_used    9639
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      34.62
_cell_measurement_theta_min      2.83
_cell_volume                     2700.13(3)
_computing_cell_refinement       'APEX2 (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, 2003)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_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  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            50054
_diffrn_reflns_theta_full        37.90
_diffrn_reflns_theta_max         37.90
_diffrn_reflns_theta_min         1.42
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_T_max  0.9143
_exptl_absorpt_correction_T_min  0.8107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.528
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         7296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0453
_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)+(0.078P)²+0.0443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1483
_reflns_number_gt                4995
_reflns_number_total             7296
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2584.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2218083
_cod_database_fobs_code          2218083
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
Cl Cl1 0.46470(2) 0.76088(4) 0.057148(10) 0.02125(8) Uani d . 1
Cl Cl2 0.36980(3) 0.56187(5) -0.116828(9) 0.02538(9) Uani d . 1
O O1 0.13288(7) 0.72551(12) 0.08499(3) 0.02032(17) Uani d . 1
C C1 0.37202(9) 0.67308(15) 0.01850(4) 0.0158(2) Uani d . 1
C C2 0.40554(10) 0.64861(15) -0.02709(4) 0.0177(2) Uani d . 1
H H2 0.4759 0.6696 -0.0356 0.021 Uiso calc R 1
C C3 0.33080(10) 0.59184(15) -0.05947(4) 0.0177(2) Uani d . 1
C C4 0.22518(9) 0.56292(16) -0.04764(4) 0.0183(2) Uani d . 1
H H4 0.1760 0.5265 -0.0699 0.022 Uiso calc R 1
C C5 0.19470(9) 0.58948(15) -0.00210(4) 0.0173(2) Uani d . 1
H H5 0.1238 0.5715 0.0060 0.021 Uiso calc R 1
C C6 0.26690(9) 0.64245(14) 0.03220(3) 0.01531(19) Uani d . 1
C C7 0.22310(9) 0.66606(15) 0.08060(4) 0.0165(2) Uani d . 1
C C8 0.28861(9) 0.60913(15) 0.12039(4) 0.0168(2) Uani d . 1
H H8 0.3512 0.5458 0.1151 0.020 Uiso calc R 1
C C9 0.25956(10) 0.64712(15) 0.16419(4) 0.0168(2) Uani d . 1
H H9 0.1962 0.7100 0.1680 0.020 Uiso calc R 1
C C10 0.31720(9) 0.59981(15) 0.20655(4) 0.01556(19) Uani d . 1
C C11 0.27256(10) 0.64353(15) 0.24970(4) 0.0179(2) Uani d . 1
H H11 0.2075 0.7031 0.2508 0.021 Uiso calc R 1
C C12 0.32405(10) 0.59919(16) 0.29076(4) 0.0189(2) Uani d . 1
H H12 0.2929 0.6294 0.3190 0.023 Uiso calc R 1
C C13 0.42150(10) 0.51030(16) 0.29039(4) 0.0182(2) Uani d . 1
C C14 0.46702(9) 0.46835(16) 0.24731(4) 0.0185(2) Uani d . 1
H H14 0.5325 0.4102 0.2463 0.022 Uiso calc R 1
C C15 0.41598(9) 0.51215(16) 0.20617(4) 0.0177(2) Uani d . 1
H H15 0.4476 0.4831 0.1779 0.021 Uiso calc R 1
C C16 0.47564(11) 0.45835(18) 0.33516(4) 0.0251(3) Uani d . 1
H H16A 0.4802 0.5608 0.3552 0.038 Uiso calc R 1
H H16B 0.5460 0.4149 0.3286 0.038 Uiso calc R 1
H H16C 0.4352 0.3662 0.3503 0.038 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
C2 C1 C6 122.08(10)
C2 C1 Cl1 116.83(9)
C6 C1 Cl1 120.90(8)
C3 C2 C1 118.00(11)
C3 C2 H2 121.0
C1 C2 H2 121.0
C4 C3 C2 121.92(10)
C4 C3 Cl2 118.90(9)
C2 C3 Cl2 119.15(10)
C5 C4 C3 118.45(10)
C5 C4 H4 120.8
C3 C4 H4 120.8
C4 C5 C6 122.15(11)
C4 C5 H5 118.9
C6 C5 H5 118.9
C1 C6 C5 117.38(10)
C1 C6 C7 125.90(10)
C5 C6 C7 116.70(10)
O1 C7 C8 122.79(10)
O1 C7 C6 118.40(10)
C8 C7 C6 118.75(10)
C9 C8 C7 121.15(11)
C9 C8 H8 119.4
C7 C8 H8 119.4
C8 C9 C10 126.71(11)
C8 C9 H9 116.6
C10 C9 H9 116.6
C11 C10 C15 118.00(10)
C11 C10 C9 119.02(10)
C15 C10 C9 122.98(10)
C12 C11 C10 120.88(11)
C12 C11 H11 119.6
C10 C11 H11 119.6
C11 C12 C13 121.12(10)
C11 C12 H12 119.4
C13 C12 H12 119.4
C12 C13 C14 118.17(10)
C12 C13 C16 120.83(10)
C14 C13 C16 120.99(11)
C15 C14 C13 121.00(11)
C15 C14 H14 119.5
C13 C14 H14 119.5
C14 C15 C10 120.83(10)
C14 C15 H15 119.6
C10 C15 H15 119.6
C13 C16 H16A 109.5
C13 C16 H16B 109.5
H16A C16 H16B 109.5
C13 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7380(11)
Cl2 C3 1.7360(11)
O1 C7 1.2228(14)
C1 C2 1.3895(15)
C1 C6 1.3957(16)
C2 C3 1.3887(16)
C2 H2 0.93
C3 C4 1.3854(17)
C4 C5 1.3795(15)
C4 H4 0.93
C5 C6 1.3971(15)
C5 H5 0.93
C6 C7 1.5077(15)
C7 C8 1.4725(15)
C8 C9 1.3424(14)
C8 H8 0.93
C9 C10 1.4609(15)
C9 H9 0.93
C10 C11 1.4008(15)
C10 C15 1.4022(17)
C11 C12 1.3871(16)
C11 H11 0.93
C12 C13 1.3919(18)
C12 H12 0.93
C13 C14 1.4006(16)
C13 C16 1.5072(16)
C14 C15 1.3855(16)
C14 H14 0.93
C15 H15 0.93
C16 H16A 0.96
C16 H16B 0.96
C16 H16C 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
C2 H2 O1 4_565 0.93 2.55 3.4352(15) 159
C8 H8 O1 8_655 0.93 2.55 3.1995(14) 127
C11 H11 Cg1 8_665 0.93 2.81 3.5611(13) 139
C14 H14 Cg1 3_645 0.93 2.93 3.7066(13) 142
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
C6 C1 C2 C3 0.00(17)
Cl1 C1 C2 C3 -175.09(9)
C1 C2 C3 C4 1.20(17)
C1 C2 C3 Cl2 179.44(9)
C2 C3 C4 C5 -0.88(17)
Cl2 C3 C4 C5 -179.12(9)
C3 C4 C5 C6 -0.67(17)
C2 C1 C6 C5 -1.44(17)
Cl1 C1 C6 C5 173.45(9)
C2 C1 C6 C7 -179.70(10)
Cl1 C1 C6 C7 -4.80(16)
C4 C5 C6 C1 1.79(17)
C4 C5 C6 C7 -179.80(10)
C1 C6 C7 O1 142.55(12)
C5 C6 C7 O1 -35.72(15)
C1 C6 C7 C8 -40.19(15)
C5 C6 C7 C8 141.55(11)
O1 C7 C8 C9 -11.25(18)
C6 C7 C8 C9 171.61(10)
C7 C8 C9 C10 -179.61(11)
C8 C9 C10 C11 -177.16(12)
C8 C9 C10 C15 2.91(19)
C15 C10 C11 C12 -0.83(17)
C9 C10 C11 C12 179.24(11)
C10 C11 C12 C13 0.09(19)
C11 C12 C13 C14 0.69(18)
C11 C12 C13 C16 -178.42(11)
C12 C13 C14 C15 -0.73(18)
C16 C13 C14 C15 178.38(11)
C13 C14 C15 C10 -0.01(18)
C11 C10 C15 C14 0.79(17)
C9 C10 C15 C14 -179.29(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655471
