#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/58/2225887.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_2225887
loop_
_publ_author_name
'Prasath, R.'
'Sarveswari, S.'
'Vijayakumar, V.'
'Narasimhamurthy, T.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 (2E)-3-(4-Bromophenyl)-1-(2-methyl-4-phenyl-3-quinolyl)prop-2-en-1-one
;
_journal_coeditor_code           HG2673
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1110
_journal_paper_doi               10.1107/S1600536810013784
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C25 H18 Br N O'
_chemical_formula_moiety         'C25 H18 Br N O'
_chemical_formula_sum            'C25 H18 Br N O'
_chemical_formula_weight         428.31
_chemical_name_systematic
;
(2E)-3-(4-Bromophenyl)-1-(2-methyl-4-phenyl-3-quinolyl)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                92.192(2)
_cell_angle_beta                 95.234(2)
_cell_angle_gamma                105.869(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6407(3)
_cell_length_b                   10.0395(4)
_cell_length_c                   15.5193(6)
_cell_measurement_reflns_used    4795
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.7
_cell_measurement_theta_min      2.6
_cell_volume                     988.92(7)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       'ω 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  0.027
_diffrn_reflns_av_sigmaI/netI    0.026
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15973
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.1
_exptl_absorpt_coefficient_mu    2.093
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.055
_refine_ls_R_factor_gt           0.033
_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)+(0.0378P)²+0.3122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.074
_refine_ls_wR_factor_ref         0.083
_reflns_number_gt                2545
_reflns_number_total             3470
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2673.cif
_cod_data_source_block           I
_cod_database_code               2225887
_cod_database_fobs_code          2225887
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
Br Br1 0.08613(5) 0.24943(4) 0.49005(2) 0.08720(16) Uani d . 1 . .
O O1 1.1467(3) 0.65490(17) 0.15079(12) 0.0608(5) Uani d . 1 . .
N N1 0.7271(3) 0.91386(18) 0.04962(12) 0.0419(4) Uani d . 1 . .
C C1 0.8532(3) 1.0419(2) 0.07979(14) 0.0377(5) Uani d . 1 . .
C C2 0.8037(4) 1.1593(2) 0.04646(15) 0.0475(6) Uani d . 1 . .
H H2 0.6909 1.1479 0.0040 0.057 Uiso calc R 1 . .
C C3 0.9207(4) 1.2891(2) 0.07632(17) 0.0540(6) Uani d . 1 . .
H H3 0.8868 1.3658 0.0541 0.065 Uiso calc R 1 . .
C C4 1.0909(4) 1.3087(2) 0.13987(16) 0.0527(6) Uani d . 1 . .
H H4 1.1685 1.3982 0.1598 0.063 Uiso calc R 1 . .
C C5 1.1440(4) 1.1977(2) 0.17279(14) 0.0431(5) Uani d . 1 . .
H H5 1.2583 1.2119 0.2148 0.052 Uiso calc R 1 . .
C C6 1.0268(3) 1.0609(2) 0.14360(13) 0.0348(5) Uani d . 1 . .
C C7 1.0703(3) 0.9398(2) 0.17656(13) 0.0344(5) Uani d . 1 . .
C C8 0.9391(3) 0.8119(2) 0.14548(14) 0.0361(5) Uani d . 1 . .
C C9 0.7675(3) 0.8033(2) 0.08138(14) 0.0395(5) Uani d . 1 . .
C C10 1.2501(3) 0.9522(2) 0.24382(13) 0.0361(5) Uani d . 1 . .
C C11 1.4566(4) 1.0046(3) 0.22479(16) 0.0522(6) Uani d . 1 . .
H H11 1.4833 1.0335 0.1697 0.063 Uiso calc R 1 . .
C C12 1.6221(4) 1.0137(3) 0.28757(19) 0.0627(7) Uani d . 1 . .
H H12 1.7597 1.0486 0.2743 0.075 Uiso calc R 1 . .
C C13 1.5861(4) 0.9721(3) 0.36906(18) 0.0591(7) Uani d . 1 . .
H H13 1.6984 0.9783 0.4109 0.071 Uiso calc R 1 . .
C C14 1.3823(4) 0.9209(3) 0.38841(16) 0.0563(6) Uani d . 1 . .
H H14 1.3568 0.8921 0.4436 0.068 Uiso calc R 1 . .
C C15 1.2162(4) 0.9120(2) 0.32667(14) 0.0451(5) Uani d . 1 . .
H H15 1.0791 0.8784 0.3409 0.054 Uiso calc R 1 . .
C C16 0.9910(4) 0.6815(2) 0.17362(15) 0.0433(5) Uani d . 1 . .
C C17 0.8555(4) 0.5880(2) 0.22805(16) 0.0488(6) Uani d . 1 . .
H H17 0.8854 0.5047 0.2391 0.059 Uiso calc R 1 . .
C C18 0.6945(4) 0.6130(2) 0.26255(15) 0.0457(6) Uani d . 1 . .
H H18 0.6660 0.6964 0.2503 0.055 Uiso calc R 1 . .
C C19 0.5548(3) 0.5238(2) 0.31818(15) 0.0444(5) Uani d . 1 . .
C C20 0.3842(4) 0.5633(3) 0.34362(17) 0.0547(6) Uani d . 1 . .
H H20 0.3621 0.6461 0.3258 0.066 Uiso calc R 1 . .
C C21 0.2463(4) 0.4832(3) 0.39470(17) 0.0602(7) Uani d . 1 . .
H H21 0.1321 0.5112 0.4110 0.072 Uiso calc R 1 . .
C C22 0.2791(4) 0.3614(3) 0.42126(16) 0.0524(6) Uani d . 1 . .
C C23 0.4469(4) 0.3192(3) 0.39775(17) 0.0580(7) Uani d . 1 . .
H H23 0.4680 0.2365 0.4161 0.070 Uiso calc R 1 . .
C C24 0.5839(4) 0.4003(2) 0.34676(17) 0.0550(6) Uani d . 1 . .
H H24 0.6984 0.3719 0.3311 0.066 Uiso calc R 1 . .
C C26 0.6217(4) 0.6658(2) 0.04495(17) 0.0538(6) Uani d . 1 . .
H H26A 0.5103 0.6364 0.0813 0.081 Uiso calc R 1 . .
H H26B 0.6990 0.5979 0.0430 0.081 Uiso calc R 1 . .
H H26C 0.5630 0.6755 -0.0126 0.081 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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 N1 C1 . . 118.80(18) ?
N1 C1 C2 . . 117.86(19) ?
N1 C1 C6 . . 122.80(18) ?
C2 C1 C6 . . 119.33(19) ?
C3 C2 C1 . . 120.1(2) ?
C3 C2 H2 . . 120.0 ?
C1 C2 H2 . . 120.0 ?
C2 C3 C4 . . 121.0(2) ?
C2 C3 H3 . . 119.5 ?
C4 C3 H3 . . 119.5 ?
C5 C4 C3 . . 120.4(2) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.5(2) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C5 C6 C1 . . 118.67(18) ?
C5 C6 C7 . . 123.60(19) ?
C1 C6 C7 . . 117.71(18) ?
C8 C7 C6 . . 118.19(19) ?
C8 C7 C10 . . 121.31(18) ?
C6 C7 C10 . . 120.49(18) ?
C7 C8 C9 . . 120.04(18) ?
C7 C8 C16 . . 119.47(18) ?
C9 C8 C16 . . 120.24(18) ?
N1 C9 C8 . . 122.44(19) ?
N1 C9 C26 . . 115.76(19) ?
C8 C9 C26 . . 121.80(19) ?
C15 C10 C11 . . 118.4(2) ?
C15 C10 C7 . . 120.84(19) ?
C11 C10 C7 . . 120.77(19) ?
C12 C11 C10 . . 120.1(2) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C13 C12 C11 . . 120.8(2) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C12 C13 C14 . . 119.3(2) ?
C12 C13 H13 . . 120.3 ?
C14 C13 H13 . . 120.3 ?
C15 C14 C13 . . 120.4(2) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
C14 C15 C10 . . 120.9(2) ?
C14 C15 H15 . . 119.6 ?
C10 C15 H15 . . 119.6 ?
O1 C16 C17 . . 120.1(2) ?
O1 C16 C8 . . 119.41(19) ?
C17 C16 C8 . . 120.4(2) ?
C18 C17 C16 . . 125.0(2) ?
C18 C17 H17 . . 117.5 ?
C16 C17 H17 . . 117.5 ?
C17 C18 C19 . . 127.3(2) ?
C17 C18 H18 . . 116.4 ?
C19 C18 H18 . . 116.4 ?
C20 C19 C24 . . 117.6(2) ?
C20 C19 C18 . . 119.0(2) ?
C24 C19 C18 . . 123.4(2) ?
C21 C20 C19 . . 121.6(2) ?
C21 C20 H20 . . 119.2 ?
C19 C20 H20 . . 119.2 ?
C20 C21 C22 . . 119.2(2) ?
C20 C21 H21 . . 120.4 ?
C22 C21 H21 . . 120.4 ?
C23 C22 C21 . . 120.9(2) ?
C23 C22 Br1 . . 119.93(19) ?
C21 C22 Br1 . . 119.18(19) ?
C22 C23 C24 . . 119.4(2) ?
C22 C23 H23 . . 120.3 ?
C24 C23 H23 . . 120.3 ?
C23 C24 C19 . . 121.3(2) ?
C23 C24 H24 . . 119.3 ?
C19 C24 H24 . . 119.3 ?
C9 C26 H26A . . 109.5 ?
C9 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C9 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 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 C22 . 1.897(2) ?
O1 C16 . 1.215(3) ?
N1 C9 . 1.314(3) ?
N1 C1 . 1.367(3) ?
C1 C2 . 1.411(3) ?
C1 C6 . 1.415(3) ?
C2 C3 . 1.360(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.396(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.361(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.415(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.427(3) ?
C7 C8 . 1.380(3) ?
C7 C10 . 1.487(3) ?
C8 C9 . 1.424(3) ?
C8 C16 . 1.513(3) ?
C9 C26 . 1.507(3) ?
C10 C15 . 1.382(3) ?
C10 C11 . 1.392(3) ?
C11 C12 . 1.381(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.368(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.375(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.375(3) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 C17 . 1.463(3) ?
C17 C18 . 1.316(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.469(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.383(3) ?
C19 C24 . 1.389(3) ?
C20 C21 . 1.376(3) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.371(4) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.369(4) ?
C23 C24 . 1.376(3) ?
C23 H23 . 0.9300 ?
C24 H24 . 0.9300 ?
C26 H26A . 0.9600 ?
C26 H26B . 0.9600 ?
C26 H26C . 0.9600 ?
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
C9 N1 C1 C2 . . . . -178.4(2) ?
C9 N1 C1 C6 . . . . 0.4(3) ?
N1 C1 C2 C3 . . . . 178.0(2) ?
C6 C1 C2 C3 . . . . -0.7(3) ?
C1 C2 C3 C4 . . . . 0.1(4) ?
C2 C3 C4 C5 . . . . 0.5(4) ?
C3 C4 C5 C6 . . . . -0.5(4) ?
C4 C5 C6 C1 . . . . -0.2(3) ?
C4 C5 C6 C7 . . . . -178.5(2) ?
N1 C1 C6 C5 . . . . -177.97(19) ?
C2 C1 C6 C5 . . . . 0.8(3) ?
N1 C1 C6 C7 . . . . 0.5(3) ?
C2 C1 C6 C7 . . . . 179.20(19) ?
C5 C6 C7 C8 . . . . 177.32(19) ?
C1 C6 C7 C8 . . . . -1.0(3) ?
C5 C6 C7 C10 . . . . -1.5(3) ?
C1 C6 C7 C10 . . . . -179.90(18) ?
C6 C7 C8 C9 . . . . 0.8(3) ?
C10 C7 C8 C9 . . . . 179.66(18) ?
C6 C7 C8 C16 . . . . 175.09(18) ?
C10 C7 C8 C16 . . . . -6.1(3) ?
C1 N1 C9 C8 . . . . -0.6(3) ?
C1 N1 C9 C26 . . . . -179.99(19) ?
C7 C8 C9 N1 . . . . 0.0(3) ?
C16 C8 C9 N1 . . . . -174.19(19) ?
C7 C8 C9 C26 . . . . 179.3(2) ?
C16 C8 C9 C26 . . . . 5.1(3) ?
C8 C7 C10 C15 . . . . -65.7(3) ?
C6 C7 C10 C15 . . . . 113.1(2) ?
C8 C7 C10 C11 . . . . 114.2(2) ?
C6 C7 C10 C11 . . . . -67.0(3) ?
C15 C10 C11 C12 . . . . 0.8(3) ?
C7 C10 C11 C12 . . . . -179.1(2) ?
C10 C11 C12 C13 . . . . -0.2(4) ?
C11 C12 C13 C14 . . . . -0.2(4) ?
C12 C13 C14 C15 . . . . -0.2(4) ?
C13 C14 C15 C10 . . . . 0.9(4) ?
C11 C10 C15 C14 . . . . -1.2(3) ?
C7 C10 C15 C14 . . . . 178.7(2) ?
C7 C8 C16 O1 . . . . -66.9(3) ?
C9 C8 C16 O1 . . . . 107.3(2) ?
C7 C8 C16 C17 . . . . 112.9(2) ?
C9 C8 C16 C17 . . . . -72.8(3) ?
O1 C16 C17 C18 . . . . 173.7(2) ?
C8 C16 C17 C18 . . . . -6.1(4) ?
C16 C17 C18 C19 . . . . -179.4(2) ?
C17 C18 C19 C20 . . . . -175.6(2) ?
C17 C18 C19 C24 . . . . 4.1(4) ?
C24 C19 C20 C21 . . . . -0.6(4) ?
C18 C19 C20 C21 . . . . 179.1(2) ?
C19 C20 C21 C22 . . . . 0.2(4) ?
C20 C21 C22 C23 . . . . 0.1(4) ?
C20 C21 C22 Br1 . . . . -178.94(19) ?
C21 C22 C23 C24 . . . . 0.0(4) ?
Br1 C22 C23 C24 . . . . 179.02(19) ?
C22 C23 C24 C19 . . . . -0.4(4) ?
C20 C19 C24 C23 . . . . 0.7(4) ?
C18 C19 C24 C23 . . . . -179.0(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744901
2 PubChem 139078807
