#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/55/2225594.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_2225594
loop_
_publ_author_name
'Dutkiewicz, Grzegorz'
'Chidan Kumar, C. S.'
'Yathirajan, H. S.'
'Narayana, B.'
'Kubicki, Maciej'
_publ_section_title
;
 3-(3-Bromo-4-methoxyphenyl)-1,5-diphenylpentane-1,5-dione
;
_journal_coeditor_code           IS2528
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o816
_journal_paper_doi               10.1107/S1600536810008548
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C24 H21 Br O3'
_chemical_formula_moiety         'C24 H21 Br O3'
_chemical_formula_sum            'C24 H21 Br O3'
_chemical_formula_weight         437.32
_chemical_name_systematic
;
3-(3-Bromo-4-methoxyphenyl)-1,5-diphenylpentane-1,5-dione
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.602(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7305(4)
_cell_length_b                   7.14024(19)
_cell_length_c                   22.8133(8)
_cell_measurement_reflns_used    5038
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      28.0379
_cell_measurement_theta_min      2.9916
_cell_volume                     1997.29(11)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et
al., 2008)
;
_computing_publication_material
;
Stereochemical Workstation Operation Manual (Siemens, 1989) and
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos CCD'
_diffrn_measurement_method       'ω scan'
_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  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7645
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.07
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    2.080
_exptl_absorpt_correction_T_max  0.536
_exptl_absorpt_correction_T_min  0.471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.357
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0238
_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)+(0.0327P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0570
_reflns_number_gt                3289
_reflns_number_total             4094
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2528.cif
_cod_data_source_block           I
_cod_original_cell_volume        1997.28(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225594
_cod_database_fobs_code          2225594
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_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
C C1 0.91462(13) 0.0724(2) 0.35970(8) 0.0145(4) Uani d . 1 . .
O O1 0.86814(9) 0.01848(17) 0.39695(5) 0.0217(3) Uani d . 1 . .
C C2 0.85537(13) 0.0764(2) 0.29248(7) 0.0134(4) Uani d . 1 . .
H H2A 0.7862 0.0060 0.2862 0.016 Uiso calc R 1 . .
H H2B 0.9006 0.0104 0.2698 0.016 Uiso calc R 1 . .
C C3 0.82916(13) 0.2738(2) 0.26526(8) 0.0131(4) Uani d . 1 . .
H H3A 0.8993 0.3445 0.2726 0.016 Uiso calc R 1 . .
C C4 0.77919(13) 0.2605(3) 0.19628(8) 0.0145(4) Uani d . 1 . .
H H4A 0.7216 0.1633 0.1880 0.017 Uiso calc R 1 . .
H H4B 0.7440 0.3815 0.1815 0.017 Uiso calc R 1 . .
O O5 0.95755(9) 0.19514(16) 0.18610(5) 0.0191(3) Uani d . 1 . .
C C5 0.86066(14) 0.2138(2) 0.16057(8) 0.0145(4) Uani d . 1 . .
C C11 1.03092(13) 0.1341(2) 0.37984(8) 0.0149(4) Uani d . 1 . .
C C12 1.08947(14) 0.1805(2) 0.33810(9) 0.0185(4) Uani d . 1 . .
H H12A 1.0549 0.1775 0.2957 0.022 Uiso calc R 1 . .
C C13 1.19792(14) 0.2310(3) 0.35891(10) 0.0261(5) Uani d . 1 . .
H H13A 1.2377 0.2622 0.3305 0.031 Uiso calc R 1 . .
C C14 1.24952(15) 0.2366(3) 0.42059(10) 0.0296(5) Uani d . 1 . .
H H14A 1.3241 0.2716 0.4344 0.035 Uiso calc R 1 . .
C C15 1.19147(15) 0.1907(2) 0.46233(10) 0.0294(5) Uani d . 1 . .
H H15A 1.2262 0.1945 0.5047 0.035 Uiso calc R 1 . .
C C16 1.08349(14) 0.1398(2) 0.44186(9) 0.0209(4) Uani d . 1 . .
H H16A 1.0442 0.1082 0.4705 0.025 Uiso calc R 1 . .
C C31 0.75354(13) 0.3834(2) 0.29399(7) 0.0121(4) Uani d . 1 . .
C C32 0.64779(13) 0.3198(2) 0.28958(7) 0.0137(4) Uani d . 1 . .
H H32A 0.6240 0.2031 0.2706 0.016 Uiso calc R 1 . .
C C33 0.57781(12) 0.4268(2) 0.31288(7) 0.0125(4) Uani d . 1 . .
Br Br33 0.435504(13) 0.33429(2) 0.306668(9) 0.01938(6) Uani d . 1 . .
O O34 0.53210(9) 0.69501(16) 0.36041(6) 0.0191(3) Uani d . 1 . .
C C34 0.60856(13) 0.5983(2) 0.34074(8) 0.0139(4) Uani d . 1 . .
C C35 0.71445(13) 0.6593(2) 0.34608(8) 0.0145(4) Uani d . 1 . .
H H35A 0.7388 0.7746 0.3659 0.017 Uiso calc R 1 . .
C C36 0.78462(13) 0.5528(2) 0.32272(7) 0.0138(4) Uani d . 1 . .
H H36A 0.8564 0.5976 0.3266 0.017 Uiso calc R 1 . .
C C51 0.81896(14) 0.1985(2) 0.09296(8) 0.0155(4) Uani d . 1 . .
C C52 0.70940(15) 0.2171(2) 0.06268(8) 0.0209(4) Uani d . 1 . .
H H52A 0.6576 0.2364 0.0853 0.025 Uiso calc R 1 . .
C C53 0.67473(16) 0.2080(3) -0.00028(9) 0.0266(5) Uani d . 1 . .
H H53A 0.5995 0.2212 -0.0207 0.032 Uiso calc R 1 . .
C C54 0.75009(16) 0.1794(2) -0.03336(8) 0.0254(4) Uani d . 1 . .
H H54A 0.7267 0.1756 -0.0766 0.031 Uiso calc R 1 . .
C C55 0.85911(16) 0.1566(2) -0.00367(8) 0.0238(4) Uani d . 1 . .
H H55A 0.9103 0.1338 -0.0264 0.029 Uiso calc R 1 . .
C C56 0.89418(15) 0.1669(2) 0.05928(8) 0.0187(4) Uani d . 1 . .
H H56A 0.9694 0.1525 0.0795 0.022 Uiso calc R 1 . .
C C341 0.55832(15) 0.8827(2) 0.38057(10) 0.0272(5) Uani d . 1 . .
H H34D 0.4945 0.9417 0.3891 0.041 Uiso calc R 1 . .
H H34A 0.5795 0.9535 0.3488 0.041 Uiso calc R 1 . .
H H34B 0.6189 0.8817 0.4177 0.041 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'
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
O1 C1 C11 . . 120.32(16) ?
O1 C1 C2 . . 120.49(15) ?
C11 C1 C2 . . 119.20(14) ?
C1 C2 C3 . . 114.82(13) ?
C1 C2 H2A . . 108.6 ?
C3 C2 H2A . . 108.6 ?
C1 C2 H2B . . 108.6 ?
C3 C2 H2B . . 108.6 ?
H2A C2 H2B . . 107.5 ?
C31 C3 C4 . . 109.78(13) ?
C31 C3 C2 . . 113.04(13) ?
C4 C3 C2 . . 110.01(14) ?
C31 C3 H3A . . 107.9 ?
C4 C3 H3A . . 107.9 ?
C2 C3 H3A . . 107.9 ?
C5 C4 C3 . . 114.18(13) ?
C5 C4 H4A . . 108.7 ?
C3 C4 H4A . . 108.7 ?
C5 C4 H4B . . 108.7 ?
C3 C4 H4B . . 108.7 ?
H4A C4 H4B . . 107.6 ?
O5 C5 C51 . . 121.14(15) ?
O5 C5 C4 . . 121.06(15) ?
C51 C5 C4 . . 117.76(14) ?
C16 C11 C12 . . 119.09(16) ?
C16 C11 C1 . . 119.11(16) ?
C12 C11 C1 . . 121.77(16) ?
C13 C12 C11 . . 119.63(18) ?
C13 C12 H12A . . 120.2 ?
C11 C12 H12A . . 120.2 ?
C12 C13 C14 . . 120.94(18) ?
C12 C13 H13A . . 119.5 ?
C14 C13 H13A . . 119.5 ?
C13 C14 C15 . . 119.63(17) ?
C13 C14 H14A . . 120.2 ?
C15 C14 H14A . . 120.2 ?
C16 C15 C14 . . 119.69(19) ?
C16 C15 H15A . . 120.2 ?
C14 C15 H15A . . 120.2 ?
C15 C16 C11 . . 121.02(18) ?
C15 C16 H16A . . 119.5 ?
C11 C16 H16A . . 119.5 ?
C36 C31 C32 . . 117.75(15) ?
C36 C31 C3 . . 121.46(14) ?
C32 C31 C3 . . 120.72(15) ?
C33 C32 C31 . . 119.98(15) ?
C33 C32 H32A . . 120.0 ?
C31 C32 H32A . . 120.0 ?
C32 C33 C34 . . 122.15(15) ?
C32 C33 Br33 . . 118.64(12) ?
C34 C33 Br33 . . 119.20(12) ?
C34 O34 C341 . . 117.10(13) ?
O34 C34 C33 . . 117.34(14) ?
O34 C34 C35 . . 125.00(15) ?
C33 C34 C35 . . 117.66(15) ?
C36 C35 C34 . . 120.34(16) ?
C36 C35 H35A . . 119.8 ?
C34 C35 H35A . . 119.8 ?
C31 C36 C35 . . 122.09(15) ?
C31 C36 H36A . . 119.0 ?
C35 C36 H36A . . 119.0 ?
C52 C51 C56 . . 119.20(16) ?
C52 C51 C5 . . 122.53(15) ?
C56 C51 C5 . . 118.26(15) ?
C51 C52 C53 . . 120.60(17) ?
C51 C52 H52A . . 119.7 ?
C53 C52 H52A . . 119.7 ?
C54 C53 C52 . . 119.80(18) ?
C54 C53 H53A . . 120.1 ?
C52 C53 H53A . . 120.1 ?
C55 C54 C53 . . 120.14(17) ?
C55 C54 H54A . . 119.9 ?
C53 C54 H54A . . 119.9 ?
C54 C55 C56 . . 120.20(17) ?
C54 C55 H55A . . 119.9 ?
C56 C55 H55A . . 119.9 ?
C55 C56 C51 . . 120.03(17) ?
C55 C56 H56A . . 120.0 ?
C51 C56 H56A . . 120.0 ?
O34 C341 H34D . . 109.5 ?
O34 C341 H34A . . 109.5 ?
H34D C341 H34A . . 109.5 ?
O34 C341 H34B . . 109.5 ?
H34D C341 H34B . . 109.5 ?
H34A C341 H34B . . 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
C1 O1 . 1.2210(19) ?
C1 C11 . 1.494(2) ?
C1 C2 . 1.516(2) ?
C2 C3 . 1.540(2) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C31 . 1.519(2) ?
C3 C4 . 1.533(2) ?
C3 H3A . 1.0000 ?
C4 C5 . 1.518(2) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
O5 C5 . 1.2214(19) ?
C5 C51 . 1.494(2) ?
C11 C16 . 1.394(2) ?
C11 C12 . 1.398(2) ?
C12 C13 . 1.382(2) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.384(3) ?
C13 H13A . 0.9500 ?
C14 C15 . 1.392(3) ?
C14 H14A . 0.9500 ?
C15 C16 . 1.376(2) ?
C15 H15A . 0.9500 ?
C16 H16A . 0.9500 ?
C31 C36 . 1.382(2) ?
C31 C32 . 1.399(2) ?
C32 C33 . 1.384(2) ?
C32 H32A . 0.9500 ?
C33 C34 . 1.387(2) ?
C33 Br33 . 1.8975(15) ?
O34 C34 . 1.3639(19) ?
O34 C341 . 1.427(2) ?
C34 C35 . 1.390(2) ?
C35 C36 . 1.384(2) ?
C35 H35A . 0.9500 ?
C36 H36A . 0.9500 ?
C51 C52 . 1.386(2) ?
C51 C56 . 1.398(2) ?
C52 C53 . 1.386(3) ?
C52 H52A . 0.9500 ?
C53 C54 . 1.386(3) ?
C53 H53A . 0.9500 ?
C54 C55 . 1.381(3) ?
C54 H54A . 0.9500 ?
C55 C56 . 1.386(2) ?
C55 H55A . 0.9500 ?
C56 H56A . 0.9500 ?
C341 H34D . 0.9800 ?
C341 H34A . 0.9800 ?
C341 H34B . 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_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C13 H13A Br33 1_655 0.95 2.76 3.613(2) 149
C35 H35A O1 1_565 0.95 2.37 3.245(2) 153
C36 H36A O5 2_755 0.95 2.56 3.493(2) 168
C54 H54A Cg1 4_565 0.95 2.60 3.489(3) 155
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
O1 C1 C2 C3 . . . . 109.67(17) ?
C11 C1 C2 C3 . . . . -70.76(18) ?
C1 C2 C3 C31 . . . . -62.13(18) ?
C1 C2 C3 C4 . . . . 174.75(13) ?
C31 C3 C4 C5 . . . . 160.56(14) ?
C2 C3 C4 C5 . . . . -74.43(17) ?
C3 C4 C5 O5 . . . . -2.1(2) ?
C3 C4 C5 C51 . . . . -179.88(14) ?
O1 C1 C11 C16 . . . . -3.8(2) ?
C2 C1 C11 C16 . . . . 176.60(15) ?
O1 C1 C11 C12 . . . . 174.16(15) ?
C2 C1 C11 C12 . . . . -5.4(2) ?
C16 C11 C12 C13 . . . . 0.1(2) ?
C1 C11 C12 C13 . . . . -177.90(16) ?
C11 C12 C13 C14 . . . . -0.2(3) ?
C12 C13 C14 C15 . . . . 0.0(3) ?
C13 C14 C15 C16 . . . . 0.2(3) ?
C14 C15 C16 C11 . . . . -0.2(3) ?
C12 C11 C16 C15 . . . . 0.1(3) ?
C1 C11 C16 C15 . . . . 178.16(16) ?
C4 C3 C31 C36 . . . . -115.94(17) ?
C2 C3 C31 C36 . . . . 120.81(17) ?
C4 C3 C31 C32 . . . . 61.0(2) ?
C2 C3 C31 C32 . . . . -62.3(2) ?
C36 C31 C32 C33 . . . . 0.8(2) ?
C3 C31 C32 C33 . . . . -176.20(15) ?
C31 C32 C33 C34 . . . . 0.3(2) ?
C31 C32 C33 Br33 . . . . -179.41(12) ?
C341 O34 C34 C33 . . . . -170.80(15) ?
C341 O34 C34 C35 . . . . 8.7(2) ?
C32 C33 C34 O34 . . . . 177.99(15) ?
Br33 C33 C34 O34 . . . . -2.3(2) ?
C32 C33 C34 C35 . . . . -1.5(2) ?
Br33 C33 C34 C35 . . . . 178.17(12) ?
O34 C34 C35 C36 . . . . -177.85(15) ?
C33 C34 C35 C36 . . . . 1.6(2) ?
C32 C31 C36 C35 . . . . -0.7(2) ?
C3 C31 C36 C35 . . . . 176.29(15) ?
C34 C35 C36 C31 . . . . -0.5(3) ?
O5 C5 C51 C52 . . . . 179.37(16) ?
C4 C5 C51 C52 . . . . -2.9(2) ?
O5 C5 C51 C56 . . . . -1.6(2) ?
C4 C5 C51 C56 . . . . 176.14(15) ?
C56 C51 C52 C53 . . . . -1.1(3) ?
C5 C51 C52 C53 . . . . 177.88(16) ?
C51 C52 C53 C54 . . . . 0.2(3) ?
C52 C53 C54 C55 . . . . 1.2(3) ?
C53 C54 C55 C56 . . . . -1.7(3) ?
C54 C55 C56 C51 . . . . 0.7(3) ?
C52 C51 C56 C55 . . . . 0.7(3) ?
C5 C51 C56 C55 . . . . -178.35(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744650
