# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 188 loop_ _publ_author_name 'Mphahlele, Malose Jack' 'De Waal, Danita' 'Dladla, Bongumusa S.' 'Fernandes, Manuel' 'Ndlovu, Stephen M.' _publ_contact_author_name 'Prof MALOSE JACK MPHAHLELE' _publ_contact_author_address ; Chemistry and Biochemistry Medical University of Southern Africa P.O. Box 235, MEDUNSA 0204, SA PRETORIA 0204 SOUTH AFRICA ; _publ_contact_author_email MPHAHLELE@MEDUNSA.AC.ZA _publ_requested_journal ; J. Chem. Soc. Perkin Trans. 2 ; _publ_section_title ; Solution Phase, Solid State and Computational Structural Studies of the 2-Aryl-3-bromoquinolin-4(1H)-one Derivatives1 ; data_mpq002_s _database_code_CSD 189746 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Bromo-2-(4'-fluorophenyl)quinolin-4(1H)-one ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H9 Br F N O' _chemical_formula_sum 'C15 H9 Br F N O' _chemical_formula_weight 318.14 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' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3 _symmetry_space_group_name_Hall '-R 3' 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' _cell_length_a 19.117(3) _cell_length_b 19.117(3) _cell_length_c 18.364(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5812(2) _cell_formula_units_Z 18 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour 'Pale Yellow' _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2844 _exptl_absorpt_coefficient_mu 3.184 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3413 _exptl_absorpt_correction_T_max 0.6641 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13404 _diffrn_reflns_av_R_equivalents 0.0853 _diffrn_reflns_av_sigmaI/netI 0.0556 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 28.35 _reflns_number_total 3215 _reflns_number_gt 2213 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0431P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3215 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0892 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0602(2) 0.03815(16) 0.03963(16) -0.00385(11) 0.00769(12) 0.02331(14) F1 0.157(2) 0.0550(13) 0.1244(19) 0.0508(13) 0.0446(17) 0.0383(15) N1 0.0478(13) 0.0345(11) 0.0277(10) 0.0052(9) 0.0075(9) 0.0208(10) O1 0.0498(11) 0.0417(10) 0.0322(9) 0.0025(7) 0.0078(8) 0.0153(9) C1 0.0367(13) 0.0332(13) 0.0319(11) 0.0013(10) -0.0002(10) 0.0169(11) C2 0.0387(14) 0.0322(12) 0.0306(11) -0.0031(9) -0.0001(10) 0.0160(11) C3 0.0324(13) 0.0365(13) 0.0287(11) 0.0009(10) -0.0028(10) 0.0122(11) C4 0.0364(13) 0.0306(12) 0.0326(12) 0.0025(9) -0.0035(10) 0.0145(11) C5 0.0508(16) 0.0397(15) 0.0412(13) 0.0075(11) 0.0039(12) 0.0182(13) C6 0.0631(19) 0.0311(14) 0.0638(18) 0.0060(13) -0.0005(15) 0.0197(14) C7 0.0665(19) 0.0418(16) 0.0571(16) -0.0057(13) -0.0033(14) 0.0334(15) C8 0.0556(17) 0.0431(15) 0.0399(13) -0.0001(11) 0.0015(12) 0.0299(14) C9 0.0411(14) 0.0334(13) 0.0319(11) 0.0000(9) -0.0041(10) 0.0192(11) C10 0.0497(16) 0.0313(13) 0.0310(12) 0.0029(10) 0.0030(10) 0.0191(12) C11 0.0611(18) 0.0442(16) 0.0425(14) 0.0016(12) -0.0018(12) 0.0302(14) C12 0.094(3) 0.0469(17) 0.0518(17) 0.0051(13) 0.0018(17) 0.0455(19) C13 0.103(3) 0.0333(16) 0.0622(19) 0.0193(14) 0.0211(19) 0.0256(19) C14 0.068(2) 0.055(2) 0.085(2) 0.0236(18) 0.0346(18) 0.0195(19) C15 0.0584(19) 0.0435(16) 0.0600(17) 0.0132(13) 0.0175(14) 0.0265(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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_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_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) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.658 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.067