#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/08/2200877.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_2200877 loop_ _publ_author_name 'Anwar Usman' 'Ibrahim Abdul Razak' 'Hoong-Kun Fun' 'Suchada Chantrapromma' 'Yan Zhang' 'Jian-Hua Xu' _publ_section_title 1-Acetyl-3-(2-chloro-2,3-dihydrobenzofuran-3-yl)-1,2-dihydro-3-hydroxy-2-oxo-3H-indole _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o37 _journal_page_last o39 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C18 H14 Cl N O4' _chemical_formula_moiety 'C18 H14 Cl N O4' _chemical_formula_sum 'C18 H14 Cl N O4' _chemical_formula_weight 343.75 _chemical_melting_point 406 _chemical_name_systematic ; 1-Acetyl-1,2-dihydro-2-oxo-3-hydroxy-3-(2-chloro-2,3- dihydrobenzofuran-3-yl)-(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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 109.5410(10) _cell_angle_beta 97.2270(10) _cell_angle_gamma 104.4270(10) _cell_formula_units_Z 2 _cell_length_a 7.86750(10) _cell_length_b 9.0796(2) _cell_length_c 12.4097(2) _cell_measurement_reflns_used 4019 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.32 _cell_measurement_theta_min 1.79 _cell_volume 787.54(3) _computing_cell_refinement 'SAINT (Siemens, 1996b)' _computing_data_collection 'SMART (Siemens, 1996a)' _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 .971 _diffrn_measured_fraction_theta_max .971 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method \w _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 .068 _diffrn_reflns_av_sigmaI/netI .1459 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 5179 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 1.79 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count none _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .265 _exptl_absorpt_correction_T_max .964 _exptl_absorpt_correction_T_min .883 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 356 _exptl_crystal_size_max .48 _exptl_crystal_size_mid .16 _exptl_crystal_size_min .14 _refine_diff_density_max .41 _refine_diff_density_min -.47 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .92 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 222 _refine_ls_number_reflns 3338 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .92 _refine_ls_R_factor_all .095 _refine_ls_R_factor_gt .072 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0688P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .174 _refine_ls_wR_factor_ref .194 _reflns_number_gt 2171 _reflns_number_total 3338 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6088.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 The following automatic conversions were performed: '_chemical_melting_point' value '406K' was changed to '406' - the value should be numeric and without a unit designator. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '406K' was changed to '406' - the value should be numeric and without a unit designator. '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 787.54(2) _cod_database_code 2200877 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl1 .15018(10) .45538(11) .18958(8) .0527(3) Uani d . 1 . . Cl O1 1.2326(3) .9055(4) .2714(2) .0627(7) Uani d . 1 . . O O2 .7094(3) .9129(3) .1841(2) .0551(7) Uani d . 1 . . O O3 .5619(3) .8896(3) .3883(2) .0443(6) Uani d . 1 . . O H3B .483(5) .885(4) .341(3) .040(10) Uiso d . 1 . . H O4 .4294(3) .4021(3) .29140(18) .0428(5) Uani d . 1 . . O N1 .9435(3) .8656(3) .2887(2) .0310(5) Uani d . 1 . . N C1 .7844(3) .7563(3) .4039(2) .0296(6) Uani d . 1 . . C C2 .7651(4) .7039(4) .4943(3) .0431(7) Uani d . 1 . . C H2A .6532 .6774 .5125 .052 Uiso calc R 1 . . H C3 .9147(5) .6907(4) .5588(3) .0526(9) Uani d . 1 . . C H3A .9022 .6508 .6182 .063 Uiso calc R 1 . . H C4 1.0811(4) .7368(4) .5342(3) .0480(8) Uani d . 1 . . C H4A 1.1800 .7275 .5780 .058 Uiso calc R 1 . . H C5 1.1059(4) .7965(3) .4468(2) .0368(7) Uani d . 1 . . C H5A 1.2197 .8309 .4328 .044 Uiso calc R 1 . . H C6 .9552(4) .8031(3) .3808(2) .0285(6) Uani d . 1 . . C C7 .7660(4) .8651(3) .2562(3) .0332(6) Uani d . 1 . . C C8 .6484(3) .7825(3) .3225(2) .0311(6) Uani d . 1 . . C C9 1.0879(4) .9188(4) .2399(3) .0377(7) Uani d . 1 . . C C10 1.0544(5) .9821(5) .1469(3) .0571(9) Uani d . 1 . . C H10A .9487 .9067 .0882 .086 Uiso calc R 1 . . H H10B 1.1562 .9935 .1116 .086 Uiso calc R 1 . . H H10C 1.0365 1.0874 .1804 .086 Uiso calc R 1 . . H C11 .5070(3) .6266(3) .2298(2) .0296(6) Uani d . 1 . . C H11A .4407 .6557 .1718 .036 Uiso calc R 1 . . H C12 .5808(4) .4907(3) .1676(2) .0317(6) Uani d . 1 . . C C13 .6819(4) .4727(4) .0829(2) .0372(7) Uani d . 1 . . C H13A .7168 .5546 .0536 .045 Uiso calc R 1 . . H C14 .7301(4) .3299(4) .0427(3) .0486(8) Uani d . 1 . . C H14A .7975 .3155 -.0143 .058 Uiso calc R 1 . . H C15 .6785(5) .2109(4) .0866(3) .0525(9) Uani d . 1 . . C H15A .7122 .1163 .0588 .063 Uiso calc R 1 . . H C16 .5778(5) .2260(4) .1712(3) .0501(9) Uani d . 1 . . C H16A .5433 .1444 .2008 .060 Uiso calc R 1 . . H C17 .5315(4) .3680(4) .2091(3) .0373(7) Uani d . 1 . . C C18 .3736(4) .5357(4) .2845(3) .0375(7) Uani d . 1 . . C H18A .3734 .6096 .3628 .045 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 Cl1 .0277(4) .0624(6) .0610(6) .0016(4) .0046(4) .0259(5) O1 .0295(12) .105(2) .0755(17) .0299(13) .0240(12) .0503(16) O2 .0368(12) .0653(15) .0806(17) .0159(11) .0058(12) .0521(15) O3 .0299(11) .0405(13) .0540(14) .0169(10) .0114(11) .0024(11) O4 .0430(12) .0450(13) .0483(13) .0125(10) .0163(10) .0262(11) N1 .0225(11) .0352(13) .0360(13) .0093(10) .0077(9) .0139(11) C1 .0281(13) .0256(13) .0304(14) .0078(11) .0078(11) .0051(12) C2 .0399(17) .0502(19) .0338(16) .0059(14) .0097(13) .0148(14) C3 .055(2) .063(2) .0377(17) .0094(18) .0054(16) .0242(17) C4 .0442(18) .062(2) .0392(17) .0217(16) .0001(14) .0207(16) C5 .0310(15) .0362(16) .0390(16) .0127(12) .0034(12) .0092(13) C6 .0285(13) .0239(13) .0293(13) .0085(10) .0076(11) .0047(11) C7 .0256(13) .0274(14) .0470(16) .0091(11) .0073(12) .0145(13) C8 .0232(13) .0352(15) .0356(15) .0124(11) .0098(11) .0109(13) C9 .0318(15) .0380(16) .0430(17) .0100(12) .0147(13) .0135(14) C10 .0465(19) .075(2) .067(2) .0172(18) .0263(18) .045(2) C11 .0246(13) .0301(14) .0337(14) .0069(11) .0069(11) .0127(12) C12 .0278(13) .0340(15) .0296(14) .0083(11) .0026(11) .0099(12) C13 .0341(15) .0400(17) .0334(15) .0112(13) .0075(12) .0093(13) C14 .0380(17) .067(2) .0384(17) .0259(16) .0082(14) .0100(16) C15 .052(2) .047(2) .056(2) .0268(16) .0036(17) .0104(17) C16 .056(2) .0327(17) .057(2) .0135(15) .0005(17) .0165(16) C17 .0299(14) .0415(17) .0375(16) .0080(13) .0022(12) .0158(14) C18 .0258(14) .0463(18) .0378(15) .0082(13) .0085(12) .0146(14) 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 Cl1 C18 . 1.810(3) yes O1 C9 . 1.204(4) ? O2 C7 . 1.201(3) ? O3 C8 . 1.419(3) yes O3 H3B . .78(3) ? O4 C17 . 1.380(4) yes O4 C18 . 1.413(3) yes N1 C7 . 1.403(4) ? N1 C9 . 1.409(3) ? N1 C6 . 1.438(3) ? C1 C2 . 1.369(4) ? C1 C6 . 1.401(4) ? C1 C8 . 1.495(4) yes C2 C3 . 1.391(5) ? C2 H2A . .93 ? C3 C4 . 1.377(5) ? C3 H3A . .93 ? C4 C5 . 1.379(4) ? C4 H4A . .93 ? C5 C6 . 1.380(4) ? C5 H5A . .93 ? C7 C8 . 1.534(4) yes C8 C11 . 1.540(4) yes C9 C10 . 1.475(4) ? C10 H10A . .96 ? C10 H10B . .96 ? C10 H10C . .96 ? C11 C12 . 1.513(4) yes C11 C18 . 1.538(4) yes C11 H11A . .98 ? C12 C17 . 1.370(4) ? C12 C13 . 1.387(4) ? C13 C14 . 1.391(4) ? C13 H13A . .93 ? C14 C15 . 1.364(5) ? C14 H14A . .93 ? C15 C16 . 1.384(5) ? C15 H15A . .93 ? C16 C17 . 1.373(4) ? C16 H16A . .93 ? C18 H18A . .98 ? 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' Cl Cl .1484 .1585 '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 C8 O3 H3B 104(3) ? C17 O4 C18 106.7(2) ? C7 N1 C9 126.0(2) ? C7 N1 C6 108.9(2) ? C9 N1 C6 125.2(2) ? C2 C1 C6 119.8(3) ? C2 C1 C8 130.1(3) ? C6 C1 C8 110.0(2) ? C1 C2 C3 119.3(3) ? C1 C2 H2A 120.3 ? C3 C2 H2A 120.3 ? C4 C3 C2 119.8(3) ? C4 C3 H3A 120.1 ? C2 C3 H3A 120.1 ? C3 C4 C5 122.1(3) ? C3 C4 H4A 118.9 ? C5 C4 H4A 118.9 ? C4 C5 C6 117.4(3) ? C4 C5 H5A 121.3 ? C6 C5 H5A 121.3 ? C5 C6 C1 121.5(2) ? C5 C6 N1 128.9(2) ? C1 C6 N1 109.5(2) ? O2 C7 N1 126.7(3) ? O2 C7 C8 124.2(2) ? N1 C7 C8 109.0(2) ? O3 C8 C1 109.9(2) ? O3 C8 C7 110.7(2) yes C1 C8 C7 102.3(2) yes O3 C8 C11 110.1(2) yes C1 C8 C11 116.3(2) ? C7 C8 C11 107.0(2) ? O1 C9 N1 119.6(3) ? O1 C9 C10 121.7(3) ? N1 C9 C10 118.6(3) ? C9 C10 H10A 109.5 ? C9 C10 H10B 109.5 ? H10A C10 H10B 109.5 ? C9 C10 H10C 109.5 ? H10A C10 H10C 109.5 ? H10B C10 H10C 109.5 ? C12 C11 C18 100.0(2) ? C12 C11 C8 115.1(2) yes C18 C11 C8 112.4(2) yes C12 C11 H11A 109.7 ? C18 C11 H11A 109.7 ? C8 C11 H11A 109.7 ? C17 C12 C13 119.3(3) ? C17 C12 C11 108.1(2) ? C13 C12 C11 132.6(3) ? C12 C13 C14 118.7(3) ? C12 C13 H13A 120.6 ? C14 C13 H13A 120.6 ? C15 C14 C13 120.1(3) ? C15 C14 H14A 120.0 ? C13 C14 H14A 120.0 ? C14 C15 C16 122.3(3) ? C14 C15 H15A 118.9 ? C16 C15 H15A 118.9 ? C17 C16 C15 116.5(3) ? C17 C16 H16A 121.8 ? C15 C16 H16A 121.8 ? C12 C17 C16 123.1(3) ? C12 C17 O4 112.7(3) ? C16 C17 O4 124.2(3) ? O4 C18 C11 107.3(2) ? O4 C18 Cl1 108.53(19) yes C11 C18 Cl1 109.52(19) yes O4 C18 H18A 110.5 ? C11 C18 H18A 110.5 ? Cl1 C18 H18A 110.5 ? 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 C6 C1 C2 C3 -3.0(4) ? C8 C1 C2 C3 -179.4(3) ? C1 C2 C3 C4 2.7(5) ? C2 C3 C4 C5 -.1(5) ? C3 C4 C5 C6 -2.3(5) ? C4 C5 C6 C1 2.0(4) ? C4 C5 C6 N1 177.1(3) ? C2 C1 C6 C5 .6(4) ? C8 C1 C6 C5 177.7(2) ? C2 C1 C6 N1 -175.4(2) ? C8 C1 C6 N1 1.7(3) ? C7 N1 C6 C5 -173.1(3) ? C9 N1 C6 C5 6.8(4) ? C7 N1 C6 C1 2.4(3) ? C9 N1 C6 C1 -177.7(2) ? C9 N1 C7 O2 -1.8(5) ? C6 N1 C7 O2 178.0(3) ? C9 N1 C7 C8 174.6(2) ? C6 N1 C7 C8 -5.5(3) ? C2 C1 C8 O3 54.3(4) ? C6 C1 C8 O3 -122.4(2) ? C2 C1 C8 C7 172.0(3) ? C6 C1 C8 C7 -4.8(3) ? C2 C1 C8 C11 -71.8(4) ? C6 C1 C8 C11 111.5(3) ? O2 C7 C8 O3 -60.1(4) ? N1 C7 C8 O3 123.3(2) ? O2 C7 C8 C1 -177.2(3) ? N1 C7 C8 C1 6.2(3) ? O2 C7 C8 C11 60.0(4) ? N1 C7 C8 C11 -116.6(2) ? C7 N1 C9 O1 -176.3(3) yes C6 N1 C9 O1 3.8(4) yes C7 N1 C9 C10 .8(4) ? C6 N1 C9 C10 -179.1(3) ? O3 C8 C11 C12 -170.4(2) ? C1 C8 C11 C12 -44.5(3) ? C7 C8 C11 C12 69.1(3) ? O3 C8 C11 C18 -56.8(3) ? C1 C8 C11 C18 69.1(3) ? C7 C8 C11 C18 -177.3(2) ? C18 C11 C12 C17 -13.9(3) ? C8 C11 C12 C17 106.8(3) ? C18 C11 C12 C13 166.3(3) ? C8 C11 C12 C13 -73.1(4) ? C17 C12 C13 C14 .0(4) ? C11 C12 C13 C14 179.9(3) ? C12 C13 C14 C15 -.2(4) ? C13 C14 C15 C16 .1(5) ? C14 C15 C16 C17 .1(5) ? C13 C12 C17 C16 .2(4) ? C11 C12 C17 C16 -179.7(3) ? C13 C12 C17 O4 -179.1(2) ? C11 C12 C17 O4 1.1(3) ? C15 C16 C17 C12 -.3(5) ? C15 C16 C17 O4 178.9(3) ? C18 O4 C17 C12 13.8(3) ? C18 O4 C17 C16 -165.4(3) ? C17 O4 C18 C11 -22.6(3) ? C17 O4 C18 Cl1 95.7(2) ? C12 C11 C18 O4 22.0(3) ? C8 C11 C18 O4 -100.5(3) ? C12 C11 C18 Cl1 -95.6(2) ? C8 C11 C18 Cl1 141.9(2) ? _cod_database_fobs_code 2200877