#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/44/7204490.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_7204490
loop_
_publ_author_name
'Mphahlele, Malose J.'
'Fernandes, Manuel A.'
'El-Nahas, Ahmed M.'
'Ottosson, Henrik'
'Ndlovu, Stephen M.'
'Sithole, Happy M.'
'Dladla, Bongumusa S.'
'De Waal, Danita'
_publ_section_title
;
 Solution phase, solid state and computational structural studies of
 the 2-aryl-3-bromoquinolin-4(1H)-one derivatives1
;
_journal_issue                   12
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              2159
_journal_paper_doi               10.1039/b206657b
_journal_year                    2002
_chemical_formula_moiety         'C15 H9 Br F N O'
_chemical_formula_sum            'C15 H9 Br F N O'
_chemical_formula_weight         318.14
_chemical_name_systematic
; 
3-Bromo-2-(4'-fluorophenyl)quinolin-4(1H)-one   
;
_space_group_IT_number           148
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                120.00
_cell_formula_units_Z            18
_cell_length_a                   19.117(3)
_cell_length_b                   19.117(3)
_cell_length_c                   18.364(5)
_cell_measurement_temperature    293(2)
_cell_volume                     5812(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '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  0.0853
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13404
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    3.184
_exptl_absorpt_correction_T_max  0.6641
_exptl_absorpt_correction_T_min  0.3413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             2844
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0338
_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)+(0.0431P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                2213
_reflns_number_total             3215
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b206657b.txt
_cod_data_source_block           mpq002_s
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Rhombohedral' changed to 'rhombohedral'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               7204490
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.308449(18) 0.086495(16) 0.938390(13) 0.04654(12) Uani 1 1 d . . .
F1 F 0.51533(18) 0.32163(13) 0.68547(13) 0.1186(9) Uani 1 1 d . . .
N1 N 0.34588(13) -0.04195(12) 0.77856(11) 0.0366(5) Uani 1 1 d . . .
H1 H 0.3683(16) -0.0305(15) 0.7396(14) 0.041(7) Uiso 1 1 d . . .
O1 O 0.23093(11) -0.09152(10) 0.97445(9) 0.0446(4) Uani 1 1 d . . .
C1 C 0.34470(14) 0.01845(14) 0.81575(12) 0.0342(5) Uani 1 1 d . . .
C2 C 0.30525(15) 0.00244(14) 0.88163(12) 0.0346(5) Uani 1 1 d . . .
C3 C 0.26454(14) -0.07669(15) 0.91334(12) 0.0348(5) Uani 1 1 d . . .
C4 C 0.26678(15) -0.13948(14) 0.86964(12) 0.0342(5) Uani 1 1 d . . .
C5 C 0.22786(17) -0.22047(16) 0.89321(14) 0.0458(6) Uani 1 1 d . . .
H5 H 0.1999 -0.2346 0.9372 0.055 Uiso 1 1 calc R . .
C6 C 0.23084(18) -0.27806(16) 0.85213(16) 0.0544(7) Uani 1 1 d . . .
H6 H 0.2055 -0.3312 0.8686 0.065 Uiso 1 1 calc R . .
C7 C 0.27154(19) -0.25848(18) 0.78542(15) 0.0523(7) Uani 1 1 d . . .
H7 H 0.2718 -0.2989 0.7574 0.063 Uiso 1 1 calc R . .
C8 C 0.31104(17) -0.18035(16) 0.76101(13) 0.0439(6) Uani 1 1 d . . .
H8 H 0.3394 -0.1672 0.7173 0.053 Uiso 1 1 calc R . .
C9 C 0.30825(15) -0.12011(14) 0.80280(12) 0.0352(5) Uani 1 1 d . . .
C10 C 0.38970(16) 0.09944(14) 0.78148(12) 0.0378(6) Uani 1 1 d . . .
C11 C 0.35246(18) 0.14443(17) 0.76812(13) 0.0476(6) Uani 1 1 d . . .
H11 H 0.2987 0.1242 0.7811 0.057 Uiso 1 1 calc R . .
C12 C 0.3952(2) 0.21950(18) 0.73546(15) 0.0599(8) Uani 1 1 d . . .
H12 H 0.3705 0.2498 0.7257 0.072 Uiso 1 1 calc R . .
C13 C 0.4737(3) 0.24806(18) 0.71788(17) 0.0702(10) Uani 1 1 d . . .
C14 C 0.5120(2) 0.2052(2) 0.72887(19) 0.0742(10) Uani 1 1 d . . .
H14 H 0.5655 0.2261 0.7147 0.089 Uiso 1 1 calc R . .
C15 C 0.47007(18) 0.12996(17) 0.76142(15) 0.0535(7) Uani 1 1 d . . .
H15 H 0.4954 0.1000 0.7698 0.064 Uiso 1 1 calc R . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 123.0(2) . . ?
C1 N1 H1 116.8(19) . . ?
C9 N1 H1 120.1(19) . . ?
N1 C1 C2 119.7(2) . . ?
N1 C1 C10 115.4(2) . . ?
C2 C1 C10 124.9(2) . . ?
C1 C2 C3 122.6(2) . . ?
C1 C2 Br1 120.95(17) . . ?
C3 C2 Br1 116.27(16) . . ?
O1 C3 C2 123.3(2) . . ?
O1 C3 C4 121.9(2) . . ?
C2 C3 C4 114.8(2) . . ?
C9 C4 C5 118.4(2) . . ?
C9 C4 C3 120.4(2) . . ?
C5 C4 C3 121.2(2) . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 119.2(2) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
N1 C9 C4 119.4(2) . . ?
N1 C9 C8 120.1(2) . . ?
C4 C9 C8 120.5(2) . . ?
C11 C10 C15 119.7(2) . . ?
C11 C10 C1 120.9(2) . . ?
C15 C10 C1 119.5(2) . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 118.8(3) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 F1 118.6(3) . . ?
C12 C13 C14 122.9(3) . . ?
F1 C13 C14 118.4(4) . . ?
C13 C14 C15 118.9(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C10 119.6(3) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.890(2) . ?
F1 C13 1.359(3) . ?
N1 C1 1.351(3) . ?
N1 C9 1.369(3) . ?
N1 H1 0.81(3) . ?
O1 C3 1.253(3) . ?
C1 C2 1.377(3) . ?
C1 C10 1.484(3) . ?
C2 C3 1.434(3) . ?
C3 C4 1.462(3) . ?
C4 C9 1.407(3) . ?
C4 C5 1.409(3) . ?
C5 C6 1.359(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.398(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.369(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.407(3) . ?
C8 H8 0.9300 . ?
C10 C11 1.385(4) . ?
C10 C15 1.393(4) . ?
C11 C12 1.384(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.355(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.359(5) . ?
C14 C15 1.384(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 1.0(4) . . . . ?
C9 N1 C1 C10 179.3(2) . . . . ?
N1 C1 C2 C3 0.0(4) . . . . ?
C10 C1 C2 C3 -178.2(2) . . . . ?
N1 C1 C2 Br1 175.66(18) . . . . ?
C10 C1 C2 Br1 -2.5(3) . . . . ?
C1 C2 C3 O1 177.3(2) . . . . ?
Br1 C2 C3 O1 1.4(3) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
Br1 C2 C3 C4 -177.00(16) . . . . ?
O1 C3 C4 C9 -177.0(2) . . . . ?
C2 C3 C4 C9 1.5(3) . . . . ?
O1 C3 C4 C5 2.9(4) . . . . ?
C2 C3 C4 C5 -178.6(2) . . . . ?
C9 C4 C5 C6 0.2(4) . . . . ?
C3 C4 C5 C6 -179.7(2) . . . . ?
C4 C5 C6 C7 -0.8(4) . . . . ?
C5 C6 C7 C8 1.7(5) . . . . ?
C6 C7 C8 C9 -1.9(4) . . . . ?
C1 N1 C9 C4 -0.6(4) . . . . ?
C1 N1 C9 C8 179.3(2) . . . . ?
C5 C4 C9 N1 179.4(2) . . . . ?
C3 C4 C9 N1 -0.7(3) . . . . ?
C5 C4 C9 C8 -0.4(4) . . . . ?
C3 C4 C9 C8 179.4(2) . . . . ?
C7 C8 C9 N1 -178.6(2) . . . . ?
C7 C8 C9 C4 1.3(4) . . . . ?
N1 C1 C10 C11 125.9(3) . . . . ?
C2 C1 C10 C11 -55.9(3) . . . . ?
N1 C1 C10 C15 -53.1(3) . . . . ?
C2 C1 C10 C15 125.1(3) . . . . ?
C15 C10 C11 C12 -0.4(4) . . . . ?
C1 C10 C11 C12 -179.4(2) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C11 C12 C13 F1 179.7(3) . . . . ?
C11 C12 C13 C14 2.0(5) . . . . ?
C12 C13 C14 C15 -2.0(6) . . . . ?
F1 C13 C14 C15 -179.6(3) . . . . ?
C13 C14 C15 C10 0.7(5) . . . . ?
C11 C10 C15 C14 0.5(4) . . . . ?
C1 C10 C15 C14 179.5(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4416929
