#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/47/2224791.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_2224791
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Narayana, B.'
'Veena, K.'
'Yathirajan, H. S.'
_publ_section_title
;
 (2E)-1-(3-Chlorophenyl)-3-phenylprop-2-en-1-one
;
_journal_coeditor_code           TK2596
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o157
_journal_paper_doi               10.1107/S1600536809053458
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H11 Cl O'
_chemical_formula_moiety         'C15 H11 Cl O'
_chemical_formula_sum            'C15 H11 Cl O'
_chemical_formula_weight         242.69
_chemical_name_systematic
;
(2E)-1-(3-Chlorophenyl)-3-phenylprop-2-en-1-one
;
_space_group_IT_number           2
_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
_cell_angle_alpha                83.182(11)
_cell_angle_beta                 89.422(10)
_cell_angle_gamma                86.662(11)
_cell_formula_units_Z            2
_cell_length_a                   5.8388(7)
_cell_length_b                   7.5975(11)
_cell_length_c                   13.1300(16)
_cell_measurement_reflns_used    3077
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      73.8
_cell_measurement_theta_min      5.9
_cell_volume                     577.35(13)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97) (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_av_sigmaI/netI    0.016
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3661
_diffrn_reflns_theta_full        67.5
_diffrn_reflns_theta_max         73.8
_diffrn_reflns_theta_min         5.9
_diffrn_standards_decay_%        <2%
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.737
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.038
_refine_ls_R_factor_gt           0.036
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0647P)²+0.2987P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.098
_refine_ls_wR_factor_ref         0.099
_reflns_number_gt                2148
_reflns_number_total             2243
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2596.cif
_cod_data_source_block           I
_cod_database_code               2224791
_cod_database_fobs_code          2224791
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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 Cl 0.32652(6) 0.68985(5) 0.56518(3) 0.02296(15) Uani d . 1 . .
O O 0.27901(18) 0.72419(15) 0.96930(8) 0.0224(3) Uani d . 1 . .
C C1 0.5736(2) 0.67070(18) 0.84979(11) 0.0160(3) Uani d . 1 . .
C C2 0.4270(2) 0.69988(18) 0.76536(11) 0.0162(3) Uani d . 1 . .
H H2A 0.2759 0.7510 0.7719 0.019 Uiso calc R 1 . .
C C3 0.5060(3) 0.65289(19) 0.67198(11) 0.0165(3) Uani d . 1 . .
C C4 0.7258(3) 0.57602(19) 0.66031(12) 0.0189(3) Uani d . 1 . .
H H4A 0.7771 0.5448 0.5956 0.023 Uiso calc R 1 . .
C C5 0.8677(3) 0.54612(19) 0.74507(12) 0.0193(3) Uani d . 1 . .
H H5A 1.0170 0.4916 0.7387 0.023 Uiso calc R 1 . .
C C6 0.7950(2) 0.59463(19) 0.83940(12) 0.0177(3) Uani d . 1 . .
H H6A 0.8955 0.5762 0.8966 0.021 Uiso calc R 1 . .
C C7 0.4848(3) 0.72066(19) 0.95085(11) 0.0175(3) Uani d . 1 . .
C C8 0.6548(3) 0.7663(2) 1.02521(12) 0.0192(3) Uani d . 1 . .
H H8A 0.8081 0.7850 1.0035 0.023 Uiso calc R 1 . .
C C9 0.5952(2) 0.78129(19) 1.12239(11) 0.0170(3) Uani d . 1 . .
H H9A 0.4423 0.7560 1.1418 0.020 Uiso calc R 1 . .
C C10 0.7434(2) 0.83314(19) 1.20198(11) 0.0161(3) Uani d . 1 . .
C C11 0.9534(3) 0.90987(19) 1.17865(11) 0.0180(3) Uani d . 1 . .
H H11A 1.0036 0.9293 1.1094 0.022 Uiso calc R 1 . .
C C12 1.0875(3) 0.95730(19) 1.25607(12) 0.0194(3) Uani d . 1 . .
H H12A 1.2287 1.0103 1.2396 0.023 Uiso calc R 1 . .
C C13 1.0172(3) 0.9280(2) 1.35792(12) 0.0217(3) Uani d . 1 . .
H H13A 1.1107 0.9600 1.4108 0.026 Uiso calc R 1 . .
C C14 0.8103(3) 0.8519(2) 1.38218(12) 0.0221(3) Uani d . 1 . .
H H14A 0.7623 0.8313 1.4517 0.026 Uiso calc R 1 . .
C C15 0.6734(3) 0.80576(19) 1.30478(12) 0.0185(3) Uani d . 1 . .
H H15A 0.5309 0.7552 1.3217 0.022 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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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 . . 120.12(14) ?
C2 C1 C7 . . 118.15(13) ?
C6 C1 C7 . . 121.73(13) ?
C3 C2 C1 . . 118.72(13) ?
C3 C2 H2A . . 120.6 ?
C1 C2 H2A . . 120.6 ?
C2 C3 C4 . . 121.96(13) ?
C2 C3 Cl . . 119.50(11) ?
C4 C3 Cl . . 118.54(11) ?
C5 C4 C3 . . 118.53(14) ?
C5 C4 H4A . . 120.7 ?
C3 C4 H4A . . 120.7 ?
C4 C5 C6 . . 120.91(14) ?
C4 C5 H5A . . 119.5 ?
C6 C5 H5A . . 119.5 ?
C5 C6 C1 . . 119.74(14) ?
C5 C6 H6A . . 120.1 ?
C1 C6 H6A . . 120.1 ?
O C7 C8 . . 122.19(14) ?
O C7 C1 . . 120.25(13) ?
C8 C7 C1 . . 117.56(13) ?
C9 C8 C7 . . 120.80(14) ?
C9 C8 H8A . . 119.6 ?
C7 C8 H8A . . 119.6 ?
C8 C9 C10 . . 126.15(14) ?
C8 C9 H9A . . 116.9 ?
C10 C9 H9A . . 116.9 ?
C15 C10 C11 . . 118.75(13) ?
C15 C10 C9 . . 119.08(13) ?
C11 C10 C9 . . 122.18(13) ?
C12 C11 C10 . . 120.27(14) ?
C12 C11 H11A . . 119.9 ?
C10 C11 H11A . . 119.9 ?
C11 C12 C13 . . 120.46(14) ?
C11 C12 H12A . . 119.8 ?
C13 C12 H12A . . 119.8 ?
C14 C13 C12 . . 119.92(14) ?
C14 C13 H13A . . 120.0 ?
C12 C13 H13A . . 120.0 ?
C13 C14 C15 . . 119.97(14) ?
C13 C14 H14A . . 120.0 ?
C15 C14 H14A . . 120.0 ?
C14 C15 C10 . . 120.63(14) ?
C14 C15 H15A . . 119.7 ?
C10 C15 H15A . . 119.7 ?
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
Cl C3 . 1.7452(15) ?
O C7 . 1.2226(19) ?
C1 C2 . 1.396(2) ?
C1 C6 . 1.397(2) ?
C1 C7 . 1.502(2) ?
C2 C3 . 1.385(2) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.393(2) ?
C4 C5 . 1.383(2) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.389(2) ?
C5 H5A . 0.9500 ?
C6 H6A . 0.9500 ?
C7 C8 . 1.483(2) ?
C8 C9 . 1.335(2) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.467(2) ?
C9 H9A . 0.9500 ?
C10 C15 . 1.402(2) ?
C10 C11 . 1.404(2) ?
C11 C12 . 1.383(2) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.391(2) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.387(2) ?
C13 H13A . 0.9500 ?
C14 C15 . 1.389(2) ?
C14 H14A . 0.9500 ?
C15 H15A . 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
C2 H2A Cg2 2_677 0.95 2.90 3.5541(16) 127
C5 H5A Cg2 2_767 0.95 2.90 3.5338(17) 125
C12 H12A Cg1 2_777 0.95 2.92 3.6040(17) 130
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 . . . . -0.3(2) ?
C7 C1 C2 C3 . . . . -179.41(12) ?
C1 C2 C3 C4 . . . . 0.7(2) ?
C1 C2 C3 Cl . . . . -179.48(10) ?
C2 C3 C4 C5 . . . . 0.1(2) ?
Cl C3 C4 C5 . . . . -179.76(11) ?
C3 C4 C5 C6 . . . . -1.2(2) ?
C4 C5 C6 C1 . . . . 1.6(2) ?
C2 C1 C6 C5 . . . . -0.8(2) ?
C7 C1 C6 C5 . . . . 178.26(12) ?
C2 C1 C7 O . . . . 26.0(2) ?
C6 C1 C7 O . . . . -153.08(14) ?
C2 C1 C7 C8 . . . . -153.42(13) ?
C6 C1 C7 C8 . . . . 27.50(19) ?
O C7 C8 C9 . . . . 12.5(2) ?
C1 C7 C8 C9 . . . . -168.11(14) ?
C7 C8 C9 C10 . . . . -177.12(13) ?
C8 C9 C10 C15 . . . . -166.17(15) ?
C8 C9 C10 C11 . . . . 14.0(2) ?
C15 C10 C11 C12 . . . . 0.0(2) ?
C9 C10 C11 C12 . . . . 179.79(13) ?
C10 C11 C12 C13 . . . . 0.6(2) ?
C11 C12 C13 C14 . . . . -0.5(2) ?
C12 C13 C14 C15 . . . . -0.2(2) ?
C13 C14 C15 C10 . . . . 0.9(2) ?
C11 C10 C15 C14 . . . . -0.7(2) ?
C9 C10 C15 C14 . . . . 179.46(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 554537
