#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/41/2014111.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_2014111
loop_
_publ_author_name
'Wang, Lei'
'Zhang, Yong'
'Lu, Cheng-Rong'
'Zhang, De-Chun'
_publ_section_title
;
 1-(4-Bromophenyl)-3-(4-methylphenyl)prop-2-en-1-one
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o696
_journal_page_last               o698
_journal_paper_doi               10.1107/S0108270104017883
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C16 H13 Br O'
_chemical_formula_moiety         'C16 H13 Br O'
_chemical_formula_sum            'C16 H13 Br O'
_chemical_formula_weight         301.17
_chemical_melting_point          .437E-305
_chemical_name_common            4-Methyl-4'-bromo-chalcone
_chemical_name_systematic
;
1-(4-Bromophenyl)-3-(4-methylphenyl)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                90.00
_cell_angle_beta                 92.029(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.600(3)
_cell_length_b                   14.235(3)
_cell_length_c                   5.8621(11)
_cell_measurement_reflns_used    4569
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.0264
_cell_measurement_theta_min      3.1484
_cell_volume                     1301.0(4)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2001)'
_computing_data_reduction        'CrystalStructure (Rigaku, 2001)'
_computing_molecular_graphics    SHELXL97
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997b)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku MercuryCCD area-detector'
_diffrn_measurement_method       ω
_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  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            12258
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    3.144
_exptl_absorpt_correction_T_max  0.3823
_exptl_absorpt_correction_T_min  0.3558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.336
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2267
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.242
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0429
_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)+(0.0295P)²+1.5303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0912
_reflns_number_gt                2144
_reflns_number_total             2267
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            de1246.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_Hall     '-p 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014111
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Br1 -0.38335(2) 0.37129(3) 0.22424(7) 0.04250(16) Uani d . 1 . . Br
O1 0.01755(15) 0.38037(19) -0.1995(4) 0.0432(6) Uani d . 1 . . O
C1 0.22169(19) 0.3884(2) 0.3007(5) 0.0228(6) Uani d . 1 . . C
C2 0.2183(2) 0.3475(2) 0.5172(5) 0.0249(7) Uani d . 1 . . C
H2 0.1650 0.3260 0.5705 0.030 Uiso calc R 1 . . H
C3 0.2920(2) 0.3382(2) 0.6551(5) 0.0262(7) Uani d . 1 . . C
H3 0.2885 0.3095 0.8008 0.031 Uiso calc R 1 . . H
C4 0.3711(2) 0.3702(2) 0.5832(5) 0.0265(7) Uani d . 1 . . C
C5 0.3741(2) 0.4126(2) 0.3704(5) 0.0292(7) Uani d . 1 . . C
H5 0.4272 0.4363 0.3201 0.035 Uiso calc R 1 . . H
C6 0.30137(19) 0.4210(2) 0.2304(5) 0.0252(7) Uani d . 1 . . C
H6 0.3054 0.4493 0.0844 0.030 Uiso calc R 1 . . H
C7 -0.09306(19) 0.3758(2) 0.0649(5) 0.0236(6) Uani d . 1 . . C
C8 -0.1539(2) 0.3431(2) -0.0966(5) 0.0269(7) Uani d . 1 . . C
H8 -0.1358 0.3213 -0.2403 0.032 Uiso calc R 1 . . H
C9 -0.2397(2) 0.3422(2) -0.0500(5) 0.0273(7) Uani d . 1 . . C
H9 -0.2807 0.3195 -0.1601 0.033 Uiso calc R 1 . . H
C10 -0.26536(19) 0.3747(2) 0.1584(5) 0.0261(6) Uani d . 1 . . C
C11 -0.2069(2) 0.4095(2) 0.3208(5) 0.0277(7) Uani d . 1 . . C
H11 -0.2257 0.4336 0.4615 0.033 Uiso calc R 1 . . H
C12 -0.12066(19) 0.4086(2) 0.2744(5) 0.0266(7) Uani d . 1 . . C
H12 -0.0798 0.4304 0.3861 0.032 Uiso calc R 1 . . H
C13 0.1473(2) 0.3945(2) 0.1434(5) 0.0248(7) Uani d . 1 . . C
H13 0.1581 0.4145 -0.0075 0.030 Uiso calc R 1 . . H
C14 0.06604(19) 0.3753(2) 0.1870(5) 0.0271(7) Uani d . 1 . . C
H14 0.0510 0.3597 0.3380 0.033 Uiso calc R 1 . . H
C15 -0.0012(2) 0.3780(2) 0.0020(6) 0.0296(7) Uani d . 1 . . C
C16 0.4515(2) 0.3583(2) 0.7358(5) 0.0315(7) Uani d . 1 . . C
H16A 0.4992 0.3379 0.6432 0.047 Uiso calc R 1 . . H
H16B 0.4410 0.3110 0.8530 0.047 Uiso calc R 1 . . H
H16C 0.4660 0.4183 0.8092 0.047 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'
Br Br -0.2901 2.4595 '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
C2 C1 C6 117.8(3) y
C2 C1 C13 122.9(3) y
C6 C1 C13 119.2(3) y
C3 C2 C1 120.8(3) ?
C3 C2 H2 119.6 ?
C1 C2 H2 119.6 ?
C2 C3 C4 121.0(3) ?
C2 C3 H3 119.5 ?
C4 C3 H3 119.5 ?
C5 C4 C3 118.2(3) y
C5 C4 C16 121.4(3) y
C3 C4 C16 120.3(3) y
C6 C5 C4 121.2(3) ?
C6 C5 H5 119.4 ?
C4 C5 H5 119.4 ?
C5 C6 C1 121.0(3) ?
C5 C6 H6 119.5 ?
C1 C6 H6 119.5 ?
C12 C7 C8 119.0(3) y
C12 C7 C15 122.6(3) y
C8 C7 C15 118.3(3) y
C9 C8 C7 120.7(3) ?
C9 C8 H8 119.6 ?
C7 C8 H8 119.6 ?
C8 C9 C10 119.2(3) ?
C8 C9 H9 120.4 ?
C10 C9 H9 120.4 ?
C9 C10 C11 121.5(3) y
C9 C10 Br1 119.1(2) y
C11 C10 Br1 119.3(2) y
C12 C11 C10 118.9(3) ?
C12 C11 H11 120.6 ?
C10 C11 H11 120.6 ?
C11 C12 C7 120.6(3) ?
C11 C12 H12 119.7 ?
C7 C12 H12 119.7 ?
C14 C13 C1 127.5(3) y
C14 C13 H13 116.3 ?
C1 C13 H13 116.3 ?
C13 C14 C15 120.6(3) y
C13 C14 H14 119.7 ?
C15 C14 H14 119.7 ?
O1 C15 C14 121.3(3) y
O1 C15 C7 120.1(3) y
C14 C15 C7 118.6(3) ?
C4 C16 H16A 109.5 ?
C4 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C4 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
Br1 C10 . 1.895(3) y
O1 C15 . 1.228(4) y
C1 C2 . 1.398(4) ?
C1 C6 . 1.403(4) ?
C1 C13 . 1.460(4) y
C2 C3 . 1.388(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.394(4) y
C3 H3 . 0.9500 ?
C4 C5 . 1.389(5) ?
C4 C16 . 1.524(4) y
C5 C6 . 1.382(4) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C12 . 1.396(4) ?
C7 C8 . 1.397(4) ?
C7 C15 . 1.493(4) y
C8 C9 . 1.375(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.379(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.387(4) ?
C11 C12 . 1.381(4) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 C14 . 1.330(4) y
C13 H13 . 0.9500 ?
C14 C15 . 1.482(4) y
C14 H14 . 0.9500 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2 O1 1_554 1_554 0.95 2.82 3.627(3) 144 y
C14 H14 O1 1_554 1_554 0.95 2.80 3.702(4) 160 y
C12 H12 O1 1_554 1_554 0.95 2.91 3.722(4) 145 y
C5 H5 Br1 1_455 1_455 0.95 3.17 3.953(5) 141 y
C16 H16A Br1 1_455 1_455 0.98 3.15 4.026(4) 149 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 -1.3(4) ?
C13 C1 C2 C3 176.0(3) y
C1 C2 C3 C4 0.8(5) ?
C2 C3 C4 C5 0.6(5) ?
C2 C3 C4 C16 -179.3(3) ?
C3 C4 C5 C6 -1.6(5) ?
C16 C4 C5 C6 178.3(3) ?
C4 C5 C6 C1 1.1(5) ?
C2 C1 C6 C5 0.3(4) ?
C13 C1 C6 C5 -177.1(3) y
C12 C7 C8 C9 -0.6(5) ?
C15 C7 C8 C9 -178.1(3) y
C7 C8 C9 C10 0.5(5) ?
C8 C9 C10 C11 0.9(5) ?
C8 C9 C10 Br1 -178.9(2) y
C9 C10 C11 C12 -2.1(5) ?
Br1 C10 C11 C12 177.7(2) y
C10 C11 C12 C7 2.0(5) ?
C8 C7 C12 C11 -0.6(5) ?
C15 C7 C12 C11 176.7(3) y
C2 C1 C13 C14 9.5(5) y
C6 C1 C13 C14 -173.3(3) y
C1 C13 C14 C15 -175.1(3) y
C13 C14 C15 O1 13.8(5) y
C13 C14 C15 C7 -167.5(3) y
C12 C7 C15 O1 -154.7(3) y
C8 C7 C15 O1 22.7(5) y
C12 C7 C15 C14 26.5(4) y
C8 C7 C15 C14 -156.1(3) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652392
