#------------------------------------------------------------------------------ #$Date: 2008-02-08 10:23:56 +0000 (Fri, 08 Feb 2008) $ #$Revision: 101 $ #$URL: svn://www.crystallography.net/cod/cif/2/2204335.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_2204335 loop_ _publ_author_name 'Yavuz K\"oysal' '\,Samil I\,s\?ik' 'Arzu Karakurt' 'Sevim Dalkara' _publ_section_title ; 2-Bromo-1-(1-hydroxynaphthalene-2-yl)ethanone ; _journal_issue 10 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o1730 _journal_page_last o1732 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C12 H9 Br O2' _chemical_formula_moiety 'C12 H9 Br O2' _chemical_formula_sum 'C12 H9 Br O2' _chemical_formula_weight 265.10 _chemical_name_systematic ; 2-Bromo-1-(1-hydroxynaphthalene-2-yl)ethanone ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 100.293(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.9207(5) _cell_length_b 10.5041(10) _cell_length_c 20.357(2) _cell_measurement_reflns_used 12498 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.05 _cell_measurement_theta_min 1.94 _cell_volume 1035.28(18) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2002)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material 'WinGX (Farrugia, 1997) and PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'STOE IPDS-II' _diffrn_measurement_method '\W 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 0.0922 _diffrn_reflns_av_sigmaI/netI 0.1065 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 7371 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 2.03 _exptl_absorpt_coefficient_mu 3.944 _exptl_absorpt_correction_T_max 0.7944 _exptl_absorpt_correction_T_min 0.3085 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'X-RED32 (Stoe & Cie, 2002)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.230 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.607 _refine_diff_density_min -0.587 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.866 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 136 _refine_ls_number_reflns 2007 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.866 _refine_ls_R_factor_all 0.1372 _refine_ls_R_factor_gt 0.0515 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0602P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1182 _refine_ls_wR_factor_ref 0.1351 _reflns_number_gt 842 _reflns_number_total 2007 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fl6117.cif 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_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' 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_ _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_type_symbol O2 0.0836(10) 0.0531(4) 0.3542(2) 0.0587(14) Uani d . 1 O H2O -0.0546 0.0406 0.3259 0.088 Uiso calc R 1 H Br1 -0.72337(15) 0.25234(9) 0.16152(4) 0.0773(3) Uani d . 1 Br C8 -0.0320(13) 0.2669(6) 0.3189(3) 0.0447(16) Uani d . 1 C O1 -0.3360(10) 0.1106(4) 0.2656(2) 0.0570(12) Uani d . 1 O C11 -0.2695(13) 0.2229(6) 0.2711(3) 0.0453(17) Uani d . 1 C C7 0.1395(13) 0.1805(6) 0.3584(3) 0.0445(16) Uani d . 1 C C6 0.3720(14) 0.2173(5) 0.4045(3) 0.0450(18) Uani d . 1 C C1 0.4335(15) 0.3506(6) 0.4116(3) 0.0472(17) Uani d . 1 C C9 0.0400(14) 0.3992(6) 0.3282(3) 0.0508(18) Uani d . 1 C H9 -0.0704 0.4597 0.3028 0.061 Uiso calc R 1 H C2 0.6664(16) 0.3871(7) 0.4579(3) 0.061(2) Uani d . 1 C H2 0.7096 0.4731 0.4630 0.073 Uiso calc R 1 H C10 0.2584(15) 0.4383(6) 0.3716(3) 0.0526(18) Uani d . 1 C H10 0.2968 0.5249 0.3758 0.063 Uiso calc R 1 H C3 0.8305(16) 0.3011(8) 0.4955(4) 0.064(2) Uani d . 1 C H3 0.9854 0.3279 0.5254 0.077 Uiso calc R 1 H C4 0.7645(16) 0.1709(8) 0.4889(4) 0.067(2) Uani d . 1 C H4 0.8735 0.1116 0.5155 0.080 Uiso calc R 1 H C5 0.5443(15) 0.1312(7) 0.4443(3) 0.058(2) Uani d . 1 C H5 0.5066 0.0446 0.4399 0.069 Uiso calc R 1 H C12 -0.4318(14) 0.3209(6) 0.2264(3) 0.0544(18) Uani d . 1 C H12A -0.3063 0.3672 0.2034 0.065 Uiso calc R 1 H H12B -0.5099 0.3813 0.2539 0.065 Uiso calc R 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O2 0.064(3) 0.029(2) 0.081(3) -0.002(2) 0.004(3) -0.003(2) Br1 0.0750(5) 0.0705(5) 0.0777(5) 0.0110(6) -0.0100(3) -0.0114(5) C8 0.055(4) 0.032(4) 0.051(3) 0.003(3) 0.020(3) -0.005(3) O1 0.062(3) 0.033(3) 0.074(3) -0.006(2) 0.007(2) -0.008(2) C11 0.049(4) 0.041(5) 0.049(3) 0.002(3) 0.015(3) -0.010(3) C7 0.055(4) 0.026(3) 0.054(4) -0.003(3) 0.014(3) -0.004(3) C6 0.052(4) 0.036(5) 0.049(3) -0.005(3) 0.016(3) -0.003(3) C1 0.058(4) 0.045(4) 0.042(4) -0.014(4) 0.020(3) -0.007(3) C9 0.059(5) 0.038(4) 0.058(4) 0.000(3) 0.019(4) 0.000(3) C2 0.072(5) 0.059(4) 0.051(4) -0.024(4) 0.010(4) -0.009(4) C10 0.066(5) 0.035(4) 0.061(4) -0.013(3) 0.022(4) -0.004(3) C3 0.052(5) 0.082(5) 0.058(5) -0.011(4) 0.007(4) -0.002(4) C4 0.062(5) 0.079(6) 0.055(5) 0.001(5) -0.001(4) 0.005(4) C5 0.066(5) 0.048(4) 0.057(4) 0.002(4) 0.006(4) 0.009(4) C12 0.055(4) 0.039(4) 0.068(4) 0.001(3) 0.009(4) -0.006(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O2 C7 1.366(7) yes O2 H2O 0.8200 ? Br1 C12 1.909(6) yes C8 C7 1.392(8) ? C8 C9 1.439(9) ? C8 C11 1.456(8) ? O1 C11 1.224(7) yes C11 C12 1.506(8) ? C7 C6 1.399(8) ? C6 C5 1.394(8) ? C6 C1 1.435(9) ? C1 C2 1.402(9) ? C1 C10 1.415(9) ? C9 C10 1.329(8) ? C9 H9 0.9300 ? C2 C3 1.354(10) ? C2 H2 0.9300 ? C10 H10 0.9300 ? C3 C4 1.407(10) ? C3 H3 0.9300 ? C4 C5 1.349(9) ? C4 H4 0.9300 ? C5 H5 0.9300 ? C12 H12A 0.9700 ? C12 H12B 0.9700 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C7 O2 H2O 109.5 ? C7 C8 C9 116.4(5) ? C7 C8 C11 120.7(6) ? C9 C8 C11 122.9(6) ? O1 C11 C8 122.4(5) yes O1 C11 C12 119.9(6) yes C8 C11 C12 117.6(5) yes O2 C7 C8 120.5(5) ? O2 C7 C6 116.3(5) ? C8 C7 C6 123.1(6) ? C5 C6 C7 123.4(6) ? C5 C6 C1 118.6(6) ? C7 C6 C1 118.0(5) ? C2 C1 C10 123.4(6) ? C2 C1 C6 117.8(6) ? C10 C1 C6 118.8(5) ? C10 C9 C8 122.4(6) ? C10 C9 H9 118.8 ? C8 C9 H9 118.8 ? C3 C2 C1 122.1(7) ? C3 C2 H2 118.9 ? C1 C2 H2 118.9 ? C9 C10 C1 121.3(6) ? C9 C10 H10 119.4 ? C1 C10 H10 119.4 ? C2 C3 C4 119.3(7) ? C2 C3 H3 120.3 ? C4 C3 H3 120.3 ? C5 C4 C3 120.6(7) ? C5 C4 H4 119.7 ? C3 C4 H4 119.7 ? C4 C5 C6 121.5(7) ? C4 C5 H5 119.3 ? C6 C5 H5 119.3 ? C11 C12 Br1 114.4(4) ? C11 C12 H12A 108.7 ? Br1 C12 H12A 108.7 ? C11 C12 H12B 108.7 ? Br1 C12 H12B 108.7 ? H12A C12 H12B 107.6 ? 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_publ_flag C7 C8 C11 O1 3.4(10) yes C9 C8 C11 O1 -176.8(6) ? C7 C8 C11 C12 -175.2(6) ? C9 C8 C11 C12 4.6(9) ? C9 C8 C7 O2 178.4(6) yes C11 C8 C7 O2 -1.8(9) ? C9 C8 C7 C6 -0.5(10) ? C11 C8 C7 C6 179.3(6) ? O2 C7 C6 C5 0.9(10) ? C8 C7 C6 C5 179.9(7) ? O2 C7 C6 C1 -178.5(6) ? C8 C7 C6 C1 0.6(10) ? C5 C6 C1 C2 0.5(10) ? C7 C6 C1 C2 179.9(7) ? C5 C6 C1 C10 -179.7(6) ? C7 C6 C1 C10 -0.3(10) ? C7 C8 C9 C10 0.2(10) ? C11 C8 C9 C10 -179.5(6) ? C10 C1 C2 C3 -180.0(7) ? C6 C1 C2 C3 -0.2(11) ? C8 C9 C10 C1 0.0(11) ? C2 C1 C10 C9 179.8(7) ? C6 C1 C10 C9 0.0(10) ? C1 C2 C3 C4 -1.0(13) ? C2 C3 C4 C5 1.8(14) ? C3 C4 C5 C6 -1.5(12) ? C7 C6 C5 C4 -179.0(7) ? C1 C6 C5 C4 0.3(11) ? O1 C11 C12 Br1 -2.7(9) ? C8 C11 C12 Br1 175.9(5) yes 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 C12 H12B O1 2_455 0.97 2.53 3.265(8) 132.0 O2 H2O O1 . 0.82 1.83 2.559(6) 147