#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2200694.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_2200694 loop_ _publ_author_name 'Usman, Anwar' 'Razak, Ibrahim Abdul' 'Fun, Hoong-Kun' 'Chantrapromma, Suchada' 'Zhang, Yan' 'Xu, Jian-Hua' _publ_section_title ; 1-Acetyl-3-(benzofuran-3-yl)-1,2-dihydro-3-hydroxy-2-oxo-3H-indole ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1070 _journal_page_last o1072 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C18 H13 N O4' _chemical_formula_sum 'C18 H13 N O4' _chemical_formula_weight 307.29 _chemical_melting_point 383 _chemical_name_systematic ; 1-Acetyl-1,2-dihydro-3-hydroxy-3-(benzofuran-3-yl)-2-oxo-(3H)indole ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL-97 _cell_angle_alpha 74.141(2) _cell_angle_beta 83.650(2) _cell_angle_gamma 78.772(2) _cell_formula_units_Z 2 _cell_length_a 7.5900(6) _cell_length_b 9.6858(8) _cell_length_c 10.4040(9) _cell_measurement_reflns_used 2226 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.47 _cell_measurement_theta_min 2.04 _cell_volume 720.32(10) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full .955 _diffrn_measured_fraction_theta_max .955 _diffrn_measurement_device_type ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0906 _diffrn_reflns_av_sigmaI/netI .1754 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 3999 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.04 _diffrn_standards_decay_% negligible _diffrn_standards_interval_count none _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .101 _exptl_absorpt_correction_T_max .9820 _exptl_absorpt_correction_T_min .9645 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 320 _exptl_crystal_size_max .36 _exptl_crystal_size_mid .24 _exptl_crystal_size_min .18 _refine_diff_density_max .297 _refine_diff_density_min -.309 _refine_ls_extinction_coef .133(14) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref .857 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 214 _refine_ls_number_reflns 2421 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .857 _refine_ls_R_factor_all .1221 _refine_ls_R_factor_gt .0724 _refine_ls_shift/su_max .000 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0390P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1740 _reflns_number_gt 1233 _reflns_number_total 2421 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file na6100.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '383K' was changed to '383' - the value should be numeric and without a unit designator. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 720.30(10) _cod_database_code 2200694 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 O1 1.0255(3) .3011(3) 1.0070(3) .0569(8) Uani d . 1 O O2 .4559(3) .3894(3) .8736(3) .0524(8) Uani d . 1 O O3 .6435(4) .1983(3) .7059(3) .0546(8) Uani d . 1 O O4 .7760(4) .4837(3) .3466(3) .0630(8) Uani d . 1 O N1 .7128(4) .4195(3) .5713(3) .0392(7) Uani d . 1 N C1 .9184(5) .3920(4) .9110(4) .0506(10) Uani d . 1 C H1A .9451 .4803 .8575 .061 Uiso calc R 1 H C2 .9391(5) .1833(4) 1.0637(4) .0430(9) Uani d . 1 C C3 1.0016(5) .0626(4) 1.1637(4) .0504(10) Uani d . 1 C H3A 1.1098 .0536 1.2020 .061 Uiso calc R 1 H C4 .8961(5) -.0433(4) 1.2039(4) .0507(10) Uani d . 1 C H4A .9339 -.1269 1.2705 .061 Uiso calc R 1 H C5 .7330(5) -.0281(4) 1.1466(4) .0528(10) Uani d . 1 C H5A .6637 -.1013 1.1770 .063 Uiso calc R 1 H C6 .6719(5) .0930(4) 1.0462(4) .0468(10) Uani d . 1 C H6A .5636 .1021 1.0082 .056 Uiso calc R 1 H C7 .7794(5) .2016(3) 1.0034(3) .0387(9) Uani d . 1 C C8 .7680(4) .3392(3) .9021(3) .0380(9) Uani d . 1 C C9 .6267(5) .4061(3) .8034(3) .0399(9) Uani d . 1 C C10 .6608(4) .3223(4) .6925(3) .0373(9) Uani d . 1 C C11 .6940(4) .5627(3) .5910(3) .0373(9) Uani d . 1 C C12 .7191(5) .6924(4) .4996(4) .0508(10) Uani d . 1 C H12A .7554 .6959 .4106 .061 Uiso calc R 1 H C13 .6877(5) .8172(4) .5461(4) .0535(11) Uani d . 1 C H13A .7026 .9057 .4864 .064 Uiso calc R 1 H C14 .6362(5) .8138(4) .6761(4) .0533(11) Uani d . 1 C H14A .6147 .8996 .7035 .064 Uiso calc R 1 H C15 .6154(5) .6839(4) .7678(4) .0507(10) Uani d . 1 C H15A .5839 .6809 .8574 .061 Uiso calc R 1 H C16 .6420(4) .5586(3) .7243(3) .0385(9) Uani d . 1 C C17 .7630(5) .3847(4) .4477(4) .0447(9) Uani d . 1 C C18 .7987(6) .2292(4) .4452(4) .0650(12) Uani d . 1 C H18A .8736 .1732 .5165 .097 Uiso calc R 1 H H18B .8588 .2201 .3609 .097 Uiso calc R 1 H H18C .6869 .1938 .4564 .097 Uiso calc R 1 H H2A .359(5) .447(3) .818(4) .056(11) Uiso d . 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 O1 .0574(17) .0555(16) .067(2) -.0260(13) -.0204(15) -.0133(13) O2 .0431(15) .0678(18) .0403(17) -.0134(13) .0023(13) -.0030(13) O3 .079(2) .0406(15) .0519(18) -.0261(13) -.0107(15) -.0112(12) O4 .082(2) .0761(19) .0350(17) -.0253(16) .0035(15) -.0157(15) N1 .0486(18) .0426(17) .0289(17) -.0168(14) -.0009(14) -.0080(13) C1 .059(2) .046(2) .052(3) -.0161(19) -.018(2) -.0096(18) C2 .049(2) .046(2) .040(2) -.0130(17) -.0072(18) -.0168(17) C3 .057(2) .055(2) .041(2) -.003(2) -.017(2) -.0135(18) C4 .065(3) .044(2) .037(2) -.0015(19) -.004(2) -.0043(17) C5 .059(2) .050(2) .046(2) -.0138(19) .000(2) -.0052(18) C6 .049(2) .047(2) .044(2) -.0167(17) -.0023(19) -.0073(18) C7 .048(2) .0396(19) .031(2) -.0094(16) -.0061(17) -.0104(15) C8 .045(2) .044(2) .030(2) -.0149(17) -.0035(16) -.0123(15) C9 .049(2) .046(2) .026(2) -.0151(17) .0042(17) -.0089(16) C10 .0347(19) .042(2) .040(2) -.0082(16) -.0092(16) -.0146(16) C11 .0384(19) .040(2) .038(2) -.0170(16) -.0032(17) -.0099(16) C12 .067(3) .050(2) .038(2) -.029(2) .0031(19) -.0043(18) C13 .066(3) .041(2) .053(3) -.0220(19) .000(2) -.0044(19) C14 .055(2) .043(2) .066(3) -.0087(18) -.009(2) -.018(2) C15 .061(3) .047(2) .049(3) -.0110(19) -.003(2) -.0195(19) C16 .043(2) .038(2) .038(2) -.0111(16) -.0035(17) -.0119(16) C17 .040(2) .064(2) .036(2) -.0160(18) -.0041(18) -.0172(19) C18 .079(3) .070(3) .055(3) -.015(2) .005(2) -.032(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 _geom_angle_publ_flag C1 O1 C2 106.0(3) ? C9 O2 H2A 110(2) ? C17 N1 C10 125.8(3) ? C17 N1 C11 124.7(3) ? C10 N1 C11 109.3(3) ? C8 C1 O1 112.5(3) ? C8 C1 H1A 123.8 ? O1 C1 H1A 123.8 ? C3 C2 C7 123.9(3) ? C3 C2 O1 126.0(3) ? C7 C2 O1 110.1(3) ? C4 C3 C2 116.6(3) ? C4 C3 H3A 121.7 ? C2 C3 H3A 121.7 ? C3 C4 C5 121.3(3) ? C3 C4 H4A 119.4 ? C5 C4 H4A 119.4 ? C6 C5 C4 121.7(4) ? C6 C5 H5A 119.2 ? C4 C5 H5A 119.2 ? C5 C6 C7 117.6(3) ? C5 C6 H6A 121.2 ? C7 C6 H6A 121.2 ? C2 C7 C6 119.0(3) ? C2 C7 C8 106.0(3) ? C6 C7 C8 135.0(3) ? C1 C8 C7 105.4(3) ? C1 C8 C9 126.8(3) ? C7 C8 C9 127.7(3) ? O2 C9 C8 107.5(3) yes O2 C9 C16 115.0(3) ? C8 C9 C16 113.9(3) ? O2 C9 C10 110.4(3) ? C8 C9 C10 107.9(3) yes C16 C9 C10 102.0(3) ? O3 C10 N1 125.9(3) ? O3 C10 C9 126.3(3) ? N1 C10 C9 107.8(3) ? C12 C11 C16 120.7(3) ? C12 C11 N1 129.6(3) ? C16 C11 N1 109.7(3) ? C11 C12 C13 117.4(4) ? C11 C12 H12A 121.3 ? C13 C12 H12A 121.3 ? C14 C13 C12 122.1(3) ? C14 C13 H13A 119.0 ? C12 C13 H13A 119.0 ? C13 C14 C15 120.5(4) ? C13 C14 H14A 119.8 ? C15 C14 H14A 119.8 ? C16 C15 C14 118.9(4) ? C16 C15 H15A 120.6 ? C14 C15 H15A 120.6 ? C15 C16 C11 120.5(3) ? C15 C16 C9 128.9(3) ? C11 C16 C9 110.6(3) ? O4 C17 N1 118.8(3) ? O4 C17 C18 122.4(3) ? N1 C17 C18 118.8(3) ? C17 C18 H18A 109.5 ? C17 C18 H18B 109.5 ? H18A C18 H18B 109.5 ? C17 C18 H18C 109.5 ? H18A C18 H18C 109.5 ? H18B C18 H18C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.362(4) yes O1 C2 1.385(4) yes O2 C9 1.430(4) yes O2 H2A .97(3) ? O3 C10 1.202(4) ? O4 C17 1.224(4) ? N1 C17 1.411(5) yes N1 C10 1.420(4) yes N1 C11 1.434(4) ? C1 C8 1.360(5) yes C1 H1A .9300 ? C2 C3 1.379(5) ? C2 C7 1.385(4) ? C3 C4 1.371(5) ? C3 H3A .9300 ? C4 C5 1.398(5) ? C4 H4A .9300 ? C5 C6 1.381(5) ? C5 H5A .9300 ? C6 C7 1.403(5) ? C6 H6A .9300 ? C7 C8 1.450(4) yes C8 C9 1.494(5) yes C9 C16 1.502(4) yes C9 C10 1.556(5) yes C11 C12 1.386(4) ? C11 C16 1.391(5) ? C12 C13 1.391(5) ? C12 H12A .9300 ? C13 C14 1.359(6) ? C13 H13A .9300 ? C14 C15 1.381(5) ? C14 H14A .9300 ? C15 C16 1.379(5) ? C15 H15A .9300 ? C17 C18 1.484(5) ? C18 H18A .9600 ? C18 H18B .9600 ? C18 H18C .9600 ? 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 _geom_hbond_publ_flag C12 H12A O4 1_555 .93 2.30 2.841(5) 117 yes O2 H2A O4 2_666 .97(4) 1.98(4) 2.893(4) 155(3) yes 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 C2 O1 C1 C8 -.2(4) ? C1 O1 C2 C3 178.5(4) ? C1 O1 C2 C7 -.3(4) ? C7 C2 C3 C4 -.2(6) ? O1 C2 C3 C4 -178.8(4) ? C2 C3 C4 C5 -.6(6) ? C3 C4 C5 C6 .9(6) ? C4 C5 C6 C7 -.3(6) ? C3 C2 C7 C6 .7(6) ? O1 C2 C7 C6 179.5(3) ? C3 C2 C7 C8 -178.2(3) ? O1 C2 C7 C8 .6(4) ? C5 C6 C7 C2 -.4(6) ? C5 C6 C7 C8 178.1(4) ? O1 C1 C8 C7 .6(4) ? O1 C1 C8 C9 -176.5(3) ? C2 C7 C8 C1 -.7(4) ? C6 C7 C8 C1 -179.4(4) ? C2 C7 C8 C9 176.3(3) ? C6 C7 C8 C9 -2.3(7) ? C1 C8 C9 O2 -139.7(4) ? C7 C8 C9 O2 43.9(4) ? C1 C8 C9 C16 -11.1(5) ? C7 C8 C9 C16 172.4(3) ? C1 C8 C9 C10 101.3(4) ? C7 C8 C9 C10 -75.2(4) ? C17 N1 C10 O3 -3.9(5) ? C11 N1 C10 O3 172.0(3) ? C17 N1 C10 C9 177.3(3) ? C11 N1 C10 C9 -6.9(3) ? O2 C9 C10 O3 -49.0(4) ? C8 C9 C10 O3 68.1(4) ? C16 C9 C10 O3 -171.7(3) ? O2 C9 C10 N1 129.8(3) ? C8 C9 C10 N1 -113.0(3) ? C16 C9 C10 N1 7.2(3) ? C17 N1 C11 C12 .0(5) ? C10 N1 C11 C12 -175.9(3) ? C17 N1 C11 C16 179.6(3) ? C10 N1 C11 C16 3.7(4) ? C16 C11 C12 C13 -.9(5) ? N1 C11 C12 C13 178.7(3) ? C11 C12 C13 C14 .6(6) ? C12 C13 C14 C15 .9(6) ? C13 C14 C15 C16 -2.1(5) ? C14 C15 C16 C11 1.8(5) ? C14 C15 C16 C9 -179.6(3) ? C12 C11 C16 C15 -.3(5) ? N1 C11 C16 C15 180.0(3) ? C12 C11 C16 C9 -179.1(3) ? N1 C11 C16 C9 1.2(4) ? O2 C9 C16 C15 56.8(5) ? C8 C9 C16 C15 -67.8(5) ? C10 C9 C16 C15 176.3(3) ? O2 C9 C16 C11 -124.5(3) ? C8 C9 C16 C11 110.9(3) ? C10 C9 C16 C11 -5.1(3) ? C10 N1 C17 O4 168.1(3) ? C11 N1 C17 O4 -7.1(5) ? C10 N1 C17 C18 -12.1(5) yes C11 N1 C17 C18 172.6(3) yes