#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/85/2228548.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_2228548
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Kobkeatthawin, Thawanrat'
'Joothamongkhon, Jaruwan'
'Chantrapromma, Suchada'
_publ_section_title
;
 (E)-3-(Anthracen-9-yl)-1-(2-bromophenyl)prop-2-en-1-one
;
_journal_coeditor_code           RZ2527
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3312
_journal_page_last               o3313
_journal_paper_doi               10.1107/S1600536810048476
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C23 H15 Br O'
_chemical_formula_moiety         'C23 H15 Br O'
_chemical_formula_sum            'C23 H15 Br O'
_chemical_formula_weight         387.25
_chemical_melting_point_gt       427
_chemical_melting_point_lt       428
_chemical_name_systematic
;
(E)-3-(Anthracen-9-yl)-1-(2-bromophenyl)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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.86310(10)
_cell_length_b                   20.0583(3)
_cell_length_c                   20.7259(3)
_cell_measurement_reflns_used    4766
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.03
_cell_volume                     3268.90(8)
_computing_cell_refinement       'SAINT (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, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22332
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.522
_exptl_absorpt_correction_T_max  0.6285
_exptl_absorpt_correction_T_min  0.4818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.458
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0336P)²+1.3057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0732
_reflns_number_gt                3717
_reflns_number_total             4766
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2527.cif
_cod_data_source_block           I
_cod_database_code               2228548
_cod_database_fobs_code          2228548
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 -0.28035(2) 0.124729(8) 0.534873(8) 0.01848(6) Uani d . 1 . .
O O1 -0.02804(17) 0.24813(6) 0.51069(6) 0.0207(3) Uani d . 1 . .
C C1 -0.0478(2) 0.09958(8) 0.53816(8) 0.0141(3) Uani d . 1 . .
C C2 -0.0051(2) 0.04186(8) 0.57118(8) 0.0182(3) Uani d . 1 . .
H H2A -0.0883 0.0173 0.5925 0.022 Uiso calc R 1 . .
C C3 0.1634(2) 0.02107(9) 0.57209(8) 0.0187(3) Uani d . 1 . .
H H3A 0.1936 -0.0173 0.5946 0.022 Uiso calc R 1 . .
C C4 0.2868(2) 0.05739(9) 0.53953(8) 0.0169(3) Uani d . 1 . .
H H4A 0.3991 0.0429 0.5396 0.020 Uiso calc R 1 . .
C C5 0.2427(2) 0.11522(8) 0.50691(8) 0.0148(3) Uani d . 1 . .
H H5A 0.3260 0.1393 0.4852 0.018 Uiso calc R 1 . .
C C6 0.0743(2) 0.13775(8) 0.50626(7) 0.0130(3) Uani d . 1 . .
C C7 0.0308(2) 0.20401(8) 0.47631(7) 0.0144(3) Uani d . 1 . .
C C8 0.0571(2) 0.21502(8) 0.40715(8) 0.0152(3) Uani d . 1 . .
H H8A 0.0380 0.2577 0.3913 0.018 Uiso calc R 1 . .
C C9 0.1067(2) 0.16805(8) 0.36499(8) 0.0143(3) Uani d . 1 . .
H H9A 0.1357 0.1266 0.3817 0.017 Uiso calc R 1 . .
C C10 0.1193(2) 0.17648(8) 0.29459(7) 0.0136(3) Uani d . 1 . .
C C11 0.1861(2) 0.23539(8) 0.26620(8) 0.0146(3) Uani d . 1 . .
C C12 0.2644(2) 0.28787(8) 0.30234(9) 0.0172(3) Uani d . 1 . .
H H12A 0.2765 0.2832 0.3467 0.021 Uiso calc R 1 . .
C C13 0.3216(2) 0.34451(9) 0.27314(9) 0.0210(4) Uani d . 1 . .
H H13A 0.3715 0.3779 0.2978 0.025 Uiso calc R 1 . .
C C14 0.3059(2) 0.35296(9) 0.20539(9) 0.0227(4) Uani d . 1 . .
H H14A 0.3417 0.3924 0.1861 0.027 Uiso calc R 1 . .
C C15 0.2388(2) 0.30366(9) 0.16882(9) 0.0211(4) Uani d . 1 . .
H H15A 0.2303 0.3095 0.1244 0.025 Uiso calc R 1 . .
C C16 0.1807(2) 0.24275(8) 0.19713(8) 0.0168(3) Uani d . 1 . .
C C17 0.1193(2) 0.19111(8) 0.15893(8) 0.0184(3) Uani d . 1 . .
H H17A 0.1169 0.1964 0.1144 0.022 Uiso calc R 1 . .
C C18 0.0612(2) 0.13157(8) 0.18586(8) 0.0161(3) Uani d . 1 . .
C C19 0.0007(2) 0.07806(9) 0.14641(8) 0.0206(4) Uani d . 1 . .
H H19A 0.0033 0.0825 0.1018 0.025 Uiso calc R 1 . .
C C20 -0.0605(2) 0.02092(9) 0.17272(9) 0.0213(4) Uani d . 1 . .
H H20A -0.0984 -0.0134 0.1462 0.026 Uiso calc R 1 . .
C C21 -0.0666(2) 0.01375(9) 0.24085(9) 0.0208(4) Uani d . 1 . .
H H21A -0.1095 -0.0252 0.2589 0.025 Uiso calc R 1 . .
C C22 -0.0101(2) 0.06361(8) 0.28000(8) 0.0178(3) Uani d . 1 . .
H H22A -0.0167 0.0581 0.3245 0.021 Uiso calc R 1 . .
C C23 0.0591(2) 0.12412(8) 0.25471(8) 0.0143(3) Uani d . 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'
Br Br -0.2901 2.4595 '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 . . 121.74(16) ?
C2 C1 Br1 . . 118.21(13) ?
C6 C1 Br1 . . 120.02(12) ?
C1 C2 C3 . . 119.22(16) ?
C1 C2 H2A . . 120.4 ?
C3 C2 H2A . . 120.4 ?
C4 C3 C2 . . 120.15(16) ?
C4 C3 H3A . . 119.9 ?
C2 C3 H3A . . 119.9 ?
C5 C4 C3 . . 120.10(16) ?
C5 C4 H4A . . 120.0 ?
C3 C4 H4A . . 120.0 ?
C4 C5 C6 . . 120.76(15) ?
C4 C5 H5A . . 119.6 ?
C6 C5 H5A . . 119.6 ?
C1 C6 C5 . . 118.00(15) ?
C1 C6 C7 . . 121.57(15) ?
C5 C6 C7 . . 120.25(15) ?
O1 C7 C8 . . 120.84(14) ?
O1 C7 C6 . . 118.86(14) ?
C8 C7 C6 . . 120.29(14) ?
C9 C8 C7 . . 124.87(15) ?
C9 C8 H8A . . 117.6 ?
C7 C8 H8A . . 117.6 ?
C8 C9 C10 . . 125.72(15) ?
C8 C9 H9A . . 117.1 ?
C10 C9 H9A . . 117.1 ?
C23 C10 C11 . . 119.88(14) ?
C23 C10 C9 . . 118.06(14) ?
C11 C10 C9 . . 122.05(14) ?
C10 C11 C12 . . 123.65(15) ?
C10 C11 C16 . . 119.09(15) ?
C12 C11 C16 . . 117.23(15) ?
C13 C12 C11 . . 121.50(16) ?
C13 C12 H12A . . 119.3 ?
C11 C12 H12A . . 119.3 ?
C12 C13 C14 . . 120.64(17) ?
C12 C13 H13A . . 119.7 ?
C14 C13 H13A . . 119.7 ?
C15 C14 C13 . . 120.04(16) ?
C15 C14 H14A . . 120.0 ?
C13 C14 H14A . . 120.0 ?
C14 C15 C16 . . 121.28(17) ?
C14 C15 H15A . . 119.4 ?
C16 C15 H15A . . 119.4 ?
C17 C16 C15 . . 120.92(16) ?
C17 C16 C11 . . 120.00(15) ?
C15 C16 C11 . . 119.08(16) ?
C16 C17 C18 . . 121.58(15) ?
C16 C17 H17A . . 119.2 ?
C18 C17 H17A . . 119.2 ?
C17 C18 C19 . . 121.51(15) ?
C17 C18 C23 . . 119.39(15) ?
C19 C18 C23 . . 119.09(15) ?
C20 C19 C18 . . 121.46(16) ?
C20 C19 H19A . . 119.3 ?
C18 C19 H19A . . 119.3 ?
C19 C20 C21 . . 119.79(16) ?
C19 C20 H20A . . 120.1 ?
C21 C20 H20A . . 120.1 ?
C22 C21 C20 . . 120.45(17) ?
C22 C21 H21A . . 119.8 ?
C20 C21 H21A . . 119.8 ?
C21 C22 C23 . . 121.94(16) ?
C21 C22 H22A . . 119.0 ?
C23 C22 H22A . . 119.0 ?
C10 C23 C22 . . 122.83(15) ?
C10 C23 C18 . . 119.92(14) ?
C22 C23 C18 . . 117.22(15) ?
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 C1 . 1.8983(17) ?
O1 C7 . 1.2269(19) ?
C1 C2 . 1.386(2) ?
C1 C6 . 1.395(2) ?
C2 C3 . 1.389(2) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.388(2) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.387(2) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.399(2) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.506(2) ?
C7 C8 . 1.465(2) ?
C8 C9 . 1.343(2) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.472(2) ?
C9 H9A . 0.9300 ?
C10 C23 . 1.418(2) ?
C10 C11 . 1.421(2) ?
C11 C12 . 1.431(2) ?
C11 C16 . 1.440(2) ?
C12 C13 . 1.364(2) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.420(3) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.353(3) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.430(2) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.390(2) ?
C17 C18 . 1.395(2) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.431(2) ?
C18 C23 . 1.435(2) ?
C19 C20 . 1.357(3) ?
C19 H19A . 0.9300 ?
C20 C21 . 1.420(2) ?
C20 H20A . 0.9300 ?
C21 C22 . 1.362(2) ?
C21 H21A . 0.9300 ?
C22 C23 . 1.430(2) ?
C22 H22A . 0.9300 ?
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
C5 H5A O1 4_556 0.93 2.53 3.301(2) 140 y
C15 H15A Cg1 8_554 0.93 2.99 3.6989(19) 135 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_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 . . . . -0.6(3) ?
Br1 C1 C2 C3 . . . . 177.50(13) ?
C1 C2 C3 C4 . . . . -0.8(3) ?
C2 C3 C4 C5 . . . . 1.1(3) ?
C3 C4 C5 C6 . . . . 0.0(2) ?
C2 C1 C6 C5 . . . . 1.7(2) ?
Br1 C1 C6 C5 . . . . -176.39(12) ?
C2 C1 C6 C7 . . . . -173.58(15) ?
Br1 C1 C6 C7 . . . . 8.4(2) ?
C4 C5 C6 C1 . . . . -1.4(2) ?
C4 C5 C6 C7 . . . . 173.95(15) ?
C1 C6 C7 O1 . . . . 58.3(2) ?
C5 C6 C7 O1 . . . . -116.82(18) ?
C1 C6 C7 C8 . . . . -121.07(17) ?
C5 C6 C7 C8 . . . . 63.8(2) ?
O1 C7 C8 C9 . . . . -173.96(17) ?
C6 C7 C8 C9 . . . . 5.4(3) ?
C7 C8 C9 C10 . . . . 174.24(16) ?
C8 C9 C10 C23 . . . . -137.39(17) ?
C8 C9 C10 C11 . . . . 41.4(3) ?
C23 C10 C11 C12 . . . . -173.75(15) ?
C9 C10 C11 C12 . . . . 7.5(2) ?
C23 C10 C11 C16 . . . . 4.2(2) ?
C9 C10 C11 C16 . . . . -174.54(15) ?
C10 C11 C12 C13 . . . . -177.81(16) ?
C16 C11 C12 C13 . . . . 4.2(2) ?
C11 C12 C13 C14 . . . . -0.4(3) ?
C12 C13 C14 C15 . . . . -2.3(3) ?
C13 C14 C15 C16 . . . . 0.8(3) ?
C14 C15 C16 C17 . . . . -176.97(17) ?
C14 C15 C16 C11 . . . . 3.2(3) ?
C10 C11 C16 C17 . . . . -3.5(2) ?
C12 C11 C16 C17 . . . . 174.62(15) ?
C10 C11 C16 C15 . . . . 176.38(15) ?
C12 C11 C16 C15 . . . . -5.5(2) ?
C15 C16 C17 C18 . . . . -179.59(16) ?
C11 C16 C17 C18 . . . . 0.2(3) ?
C16 C17 C18 C19 . . . . -178.97(16) ?
C16 C17 C18 C23 . . . . 2.2(3) ?
C17 C18 C19 C20 . . . . -178.01(17) ?
C23 C18 C19 C20 . . . . 0.8(3) ?
C18 C19 C20 C21 . . . . 0.6(3) ?
C19 C20 C21 C22 . . . . -0.6(3) ?
C20 C21 C22 C23 . . . . -0.9(3) ?
C11 C10 C23 C22 . . . . -179.81(15) ?
C9 C10 C23 C22 . . . . -1.0(2) ?
C11 C10 C23 C18 . . . . -1.8(2) ?
C9 C10 C23 C18 . . . . 176.97(15) ?
C21 C22 C23 C10 . . . . -179.72(16) ?
C21 C22 C23 C18 . . . . 2.2(2) ?
C17 C18 C23 C10 . . . . -1.4(2) ?
C19 C18 C23 C10 . . . . 179.73(15) ?
C17 C18 C23 C22 . . . . 176.71(15) ?
C19 C18 C23 C22 . . . . -2.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26231287
