#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/74/2227478.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_2227478
loop_
_publ_author_name
'Guo, Meng'
_publ_section_title
;
 1-(4-Chlorophenyl)-3-(3,4-dimethylphenyl)prop-2-en-1-one
;
_journal_coeditor_code           HB5576
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2302
_journal_paper_doi               10.1107/S1600536810031880
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H15 Cl O'
_chemical_formula_moiety         'C17 H15 Cl O'
_chemical_formula_sum            'C17 H15 Cl O'
_chemical_formula_weight         270.74
_chemical_name_systematic
;
1-(4-Chlorophenyl)-3-(3,4-dimethylphenyl)prop-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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.30(3)
_cell_angle_beta                 99.96(3)
_cell_angle_gamma                95.23(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9621(12)
_cell_length_b                   7.7369(15)
_cell_length_c                   15.513(3)
_cell_measurement_reflns_used    2643
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.19
_cell_volume                     692.5(3)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6689
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bar
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.518
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0606
_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)+(0.1287P)²+0.0873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1775
_refine_ls_wR_factor_ref         0.1875
_reflns_number_gt                2643
_reflns_number_total             3141
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5576.cif
_cod_data_source_block           I
_cod_original_cell_volume        692.5(2)
_cod_database_code               2227478
_cod_database_fobs_code          2227478
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 Cl1 0.06653(10) 0.43200(7) -0.40023(3) 0.0645(2) Uani d . 1 . .
C C2 0.2286(3) 0.4248(2) -0.22733(12) 0.0442(4) Uani d . 1 . .
H H2A 0.3675 0.4759 -0.2370 0.053 Uiso calc R 1 . .
C C15 0.3097(3) 0.2253(2) 0.26373(11) 0.0398(4) Uani d . 1 . .
H H15A 0.1822 0.2763 0.2774 0.048 Uiso calc R 1 . .
C C10 0.3326(3) 0.1916(2) 0.17512(11) 0.0372(4) Uani d . 1 . .
C C1 0.0394(3) 0.3865(2) -0.29529(11) 0.0419(4) Uani d . 1 . .
C C9 0.1543(3) 0.2354(2) 0.10668(11) 0.0405(4) Uani d . 1 . .
H H9A 0.0194 0.2644 0.1245 0.049 Uiso calc R 1 . .
C C7 -0.0361(3) 0.2764(2) -0.04009(11) 0.0417(4) Uani d . 1 . .
C C6 -0.1707(3) 0.3131(2) -0.28266(12) 0.0476(4) Uani d . 1 . .
H H6A -0.2959 0.2877 -0.3293 0.057 Uiso calc R 1 . .
O O1 -0.2265(2) 0.2775(2) -0.02091(9) 0.0582(4) Uani d . 1 . .
C C11 0.5261(3) 0.1151(2) 0.15544(12) 0.0425(4) Uani d . 1 . .
H H11A 0.5490 0.0942 0.0972 0.051 Uiso calc R 1 . .
C C8 0.1647(3) 0.2382(2) 0.02181(12) 0.0449(4) Uani d . 1 . .
H H8A 0.2987 0.2161 0.0013 0.054 Uiso calc R 1 . .
C C4 -0.0022(3) 0.3133(2) -0.12946(10) 0.0369(4) Uani d . 1 . .
C C3 0.2072(3) 0.3857(2) -0.14451(11) 0.0425(4) Uani d . 1 . .
H H3A 0.3340 0.4081 -0.0985 0.051 Uiso calc R 1 . .
C C12 0.6825(3) 0.0710(2) 0.22314(12) 0.0445(4) Uani d . 1 . .
H H12A 0.8084 0.0181 0.2092 0.053 Uiso calc R 1 . .
C C14 0.4693(3) 0.1859(2) 0.33241(11) 0.0412(4) Uani d . 1 . .
C C13 0.6579(3) 0.1031(2) 0.31155(12) 0.0417(4) Uani d . 1 . .
C C5 -0.1902(3) 0.2784(2) -0.19930(12) 0.0441(4) Uani d . 1 . .
H H5A -0.3309 0.2311 -0.1895 0.053 Uiso calc R 1 . .
C C17 0.4398(4) 0.2300(4) 0.42722(13) 0.0626(6) Uani d . 1 . .
H H17A 0.5647 0.1938 0.4657 0.094 Uiso calc R 1 . .
H H17B 0.2977 0.1697 0.4343 0.094 Uiso calc R 1 . .
H H17C 0.4381 0.3546 0.4422 0.094 Uiso calc R 1 . .
C C16 0.8291(4) 0.0483(3) 0.38260(15) 0.0594(5) Uani d . 1 . .
H H16A 0.9448 -0.0063 0.3562 0.089 Uiso calc R 1 . .
H H16B 0.7525 -0.0338 0.4119 0.089 Uiso calc R 1 . .
H H16C 0.8994 0.1499 0.4250 0.089 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 C2 C3 . . 118.67(15) ?
C1 C2 H2A . . 120.7 ?
C3 C2 H2A . . 120.7 ?
C14 C15 C10 . . 122.73(15) ?
C14 C15 H15A . . 118.6 ?
C10 C15 H15A . . 118.6 ?
C15 C10 C11 . . 118.03(15) ?
C15 C10 C9 . . 119.14(14) ?
C11 C10 C9 . . 122.83(15) ?
C2 C1 C6 . . 122.03(16) ?
C2 C1 Cl1 . . 118.89(13) ?
C6 C1 Cl1 . . 119.08(13) ?
C8 C9 C10 . . 127.04(15) ?
C8 C9 H9A . . 116.5 ?
C10 C9 H9A . . 116.5 ?
O1 C7 C8 . . 122.36(16) ?
O1 C7 C4 . . 119.56(16) ?
C8 C7 C4 . . 118.08(14) ?
C5 C6 C1 . . 118.51(15) ?
C5 C6 H6A . . 120.7 ?
C1 C6 H6A . . 120.7 ?
C12 C11 C10 . . 119.58(15) ?
C12 C11 H11A . . 120.2 ?
C10 C11 H11A . . 120.2 ?
C9 C8 C7 . . 120.28(16) ?
C9 C8 H8A . . 119.9 ?
C7 C8 H8A . . 119.9 ?
C3 C4 C5 . . 119.06(15) ?
C3 C4 C7 . . 122.57(14) ?
C5 C4 C7 . . 118.34(15) ?
C2 C3 C4 . . 120.69(15) ?
C2 C3 H3A . . 119.7 ?
C4 C3 H3A . . 119.7 ?
C11 C12 C13 . . 122.25(15) ?
C11 C12 H12A . . 118.9 ?
C13 C12 H12A . . 118.9 ?
C15 C14 C13 . . 118.70(15) ?
C15 C14 C17 . . 120.56(15) ?
C13 C14 C17 . . 120.74(16) ?
C12 C13 C14 . . 118.63(15) ?
C12 C13 C16 . . 120.30(16) ?
C14 C13 C16 . . 121.07(16) ?
C6 C5 C4 . . 121.01(16) ?
C6 C5 H5A . . 119.5 ?
C4 C5 H5A . . 119.5 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 . 1.7455(17) ?
C2 C1 . 1.382(3) ?
C2 C3 . 1.386(3) ?
C2 H2A . 0.9300 ?
C15 C14 . 1.389(2) ?
C15 C10 . 1.394(2) ?
C15 H15A . 0.9300 ?
C10 C11 . 1.403(2) ?
C10 C9 . 1.467(2) ?
C1 C6 . 1.385(3) ?
C9 C8 . 1.332(2) ?
C9 H9A . 0.9300 ?
C7 O1 . 1.222(2) ?
C7 C8 . 1.481(2) ?
C7 C4 . 1.499(2) ?
C6 C5 . 1.380(3) ?
C6 H6A . 0.9300 ?
C11 C12 . 1.383(3) ?
C11 H11A . 0.9300 ?
C8 H8A . 0.9300 ?
C4 C3 . 1.392(2) ?
C4 C5 . 1.394(2) ?
C3 H3A . 0.9300 ?
C12 C13 . 1.394(2) ?
C12 H12A . 0.9300 ?
C14 C13 . 1.406(2) ?
C14 C17 . 1.505(3) ?
C13 C16 . 1.504(2) ?
C5 H5A . 0.9300 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745773
