#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2011175.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_2011175 loop_ _publ_author_name 'Thinapong, Pongchan' 'Rangsiman, Orapin' 'Tuchinda, Patoomratana' 'Munyoo, Bamroong' 'Pohmakotr, Manat' 'Reutrakul, Vichai' _publ_section_title ; 9,10-Dimethoxy-4-methyl-1,2-dihydro-1-azaanthracen-2-one (kalasinamide), a new azaanthracene alkaloid ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e309 _journal_page_last e310 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C16 H15 N O3' _chemical_formula_sum 'C16 H15 N O3' _chemical_formula_weight 269.300 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90.0(2) _cell_angle_beta 105.8(2) _cell_angle_gamma 90.0(2) _cell_formula_units_Z 4 _cell_length_a 10.005(5) _cell_length_b 16.449(5) _cell_length_c 8.186(5) _cell_measurement_reflns_used 9 _cell_measurement_temperature 298 _cell_measurement_theta_max 11.7400 _cell_measurement_theta_min 8.8300 _cell_volume 1296.3(17) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'maXus (Mackay et al., 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_measured_fraction_theta_full .961 _diffrn_measured_fraction_theta_max .961 _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w-2\q _diffrn_radiation_source 'rotating anode generator' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .70930 _diffrn_reflns_av_R_equivalents .066 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 9602 _diffrn_reflns_theta_full 24.97 _diffrn_reflns_theta_max 24.93 _diffrn_standards_decay_% .813 _diffrn_standards_interval_time 2608 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .096 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_size_max .250 _exptl_crystal_size_mid .040 _exptl_crystal_size_min .025 _refine_diff_density_max .24 _refine_diff_density_min -.29 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 184 _refine_ls_number_reflns 2272 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all .068 _refine_ls_R_factor_gt .053 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.0824P)^2^+0.7373P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_ref .163 _reflns_number_gt 1785 _reflns_number_total 2272 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file qb0205.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 1297.0(10) _cod_database_code 2011175 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z '-X,+Y+ 1/2,-Z+ 1/2' '+X,-Y+ 1/2,+Z+ 1/2' 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 .19412(15) .53442(9) .14924(18) .0430(4) Uani d . 1 O O2 .66117(17) .52286(12) .4852(2) .0579(5) Uani d . 1 O O3 .48398(17) .70615(9) -.22291(19) .0487(4) Uani d . 1 O N1 .47139(18) .55055(11) .2710(2) .0407(5) Uani d . 1 N H1 .4206 .5260 .3250 .049 Uiso calc R 1 H C2 .6097(2) .55317(14) .3438(3) .0450(5) Uani d . 1 C C3 .6901(2) .59236(15) .2461(3) .0496(6) Uani d . 1 C H3 .7860 .5936 .2908 .060 Uiso calc R 1 H C4 .6361(2) .62745(14) .0946(3) .0445(5) Uani d . 1 C C5 .1947(3) .69683(14) -.3442(3) .0494(6) Uani d . 1 C H5 .2425 .7285 -.4038 .059 Uiso calc R 1 H C6 .0547(3) .68918(16) -.4028(3) .0576(7) Uani d . 1 C H6 .0077 .7157 -.5020 .069 Uiso calc R 1 H C7 -.0195(3) .64184(18) -.3157(3) .0589(7) Uani d . 1 C H7 -.1149 .6357 -.3596 .071 Uiso calc R 1 H C8 .0469(2) .60464(15) -.1668(3) .0489(6) Uani d . 1 C H8 -.0036 .5742 -.1086 .059 Uiso calc R 1 H C9 .2642(2) .57739(12) .0551(3) .0374(5) Uani d . 1 C C10 .4140(2) .66153(12) -.1314(3) .0393(5) Uani d . 1 C C11 .7350(3) .6661(2) .0077(4) .0697(8) Uani d . 1 C H11A .8264 .6677 .0847 .104 Uiso calc R 1 H H11B .7047 .7204 -.0263 .104 Uiso calc R 1 H H11C .7368 .6347 -.0905 .104 Uiso calc R 1 H C12 .1369(3) .58426(17) .2573(3) .0548(6) Uani d . 1 C H12A .2072 .6205 .3209 .082 Uiso calc R 1 H H12B .1046 .5503 .3340 .082 Uiso calc R 1 H H12C .0607 .6153 .1893 .082 Uiso calc R 1 H C13 .5062(4) .66468(17) -.3667(4) .0671(8) Uani d . 1 C H13A .5741 .6227 -.3289 .101 Uiso calc R 1 H H13B .5388 .7026 -.4362 .101 Uiso calc R 1 H H13C .4205 .6410 -.4314 .101 Uiso calc R 1 H C41 .4869(2) .62533(12) .0213(3) .0377(5) Uani d . 1 C C81 .1926(2) .61220(13) -.1007(3) .0396(5) Uani d . 1 C C91 .4058(2) .58486(12) .1147(2) .0360(5) Uani d . 1 C C101 .2686(2) .65706(12) -.1931(3) .0404(5) Uani d . 1 C 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 .0419(8) .0495(8) .0414(8) -.0065(6) .0178(7) .0028(6) O2 .0444(9) .0837(13) .0440(9) .0057(8) .0092(7) .0177(9) O3 .0615(10) .0490(9) .0432(9) -.0067(7) .0274(8) .0038(7) N1 .0371(10) .0512(10) .0361(9) .0001(8) .0136(8) .0078(8) C2 .0392(12) .0562(13) .0405(12) .0033(10) .0121(10) .0025(10) C3 .0339(11) .0658(15) .0498(13) -.0012(10) .0125(10) .0021(11) C4 .0405(12) .0513(12) .0465(13) -.0001(10) .0202(10) .0024(10) C5 .0629(15) .0504(13) .0355(11) .0038(11) .0146(11) .0018(10) C6 .0631(16) .0673(16) .0375(12) .0133(13) .0052(11) .0063(11) C7 .0458(13) .0809(17) .0437(13) .0043(12) .0013(11) -.0008(12) C8 .0435(12) .0611(14) .0417(12) -.0025(11) .0105(10) -.0038(10) C9 .0390(11) .0413(10) .0345(10) -.0031(9) .0145(9) .0001(8) C10 .0484(12) .0397(11) .0347(11) -.0018(9) .0198(9) -.0005(8) C11 .0439(14) .096(2) .0766(19) -.0019(14) .0284(13) .0244(16) C12 .0500(14) .0719(16) .0491(14) .0083(12) .0249(11) .0060(12) C13 .095(2) .0667(16) .0551(16) -.0054(15) .0461(15) .0016(13) C41 .0406(11) .0396(11) .0370(11) -.0009(9) .0173(9) -.0032(8) C81 .0417(11) .0445(11) .0331(11) -.0014(9) .0110(9) -.0052(9) C91 .0405(11) .0387(10) .0301(10) .0012(9) .0120(8) -.0015(8) C101 .0501(13) .0405(11) .0319(11) .0007(9) .0130(9) -.0021(8) 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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 0 1 -4 -2 -6 2 4 2 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C9 O1 C12 113.78(18) C10 O3 C13 114.35(19) C2 N1 C91 124.3(2) C2 N1 H1 117.8 C91 N1 H1 117.8 O2 C2 N1 121.1(3) O2 C2 C3 123.4(2) N1 C2 C3 115.6(2) C4 C3 C2 124.3(2) C4 C3 H3 117.8 C2 C3 H3 117.8 C3 C4 C41 118.8(3) C3 C4 C11 117.8(2) C41 C4 C11 123.3(2) C6 C5 C101 120.6(3) C6 C5 H5 119.7 C101 C5 H5 119.7 C5 C6 C7 120.8(2) C5 C6 H6 119.6 C7 C6 H6 119.6 C8 C7 C6 120.6(2) C8 C7 H7 119.7 C6 C7 H7 119.7 C7 C8 C81 120.2(3) C7 C8 H8 119.9 C81 C8 H8 119.9 O1 C9 C91 118.9(2) O1 C9 C81 120.6(2) C91 C9 C81 120.6(2) O3 C10 C41 119.8(2) O3 C10 C101 117.7(2) C41 C10 C101 122.4(2) C4 C11 H11A 109.5 C4 C11 H11B 109.5 H11A C11 H11B 109.5 C4 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 O1 C12 H12A 109.5 O1 C12 H12B 109.5 H12A C12 H12B 109.5 O1 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 O3 C13 H13A 109.5 O3 C13 H13B 109.5 H13A C13 H13B 109.5 O3 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C10 C41 C91 116.4(2) C10 C41 C4 126.0(2) C91 C41 C4 117.5(2) C9 C81 C8 122.0(3) C9 C81 C101 118.8(2) C8 C81 C101 119.2(2) C9 C91 N1 118.3(2) C9 C91 C41 122.3(2) N1 C91 C41 119.3(2) C10 C101 C5 122.2(3) C10 C101 C81 119.2(2) C5 C101 C81 118.6(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C9 1.371(3) O1 C12 1.435(3) O2 C2 1.237(3) O3 C10 1.371(3) O3 C13 1.429(3) N1 C2 1.351(4) N1 C91 1.389(3) N1 H1 .8600 C2 C3 1.433(4) C3 C4 1.342(4) C3 H3 .9300 C4 C41 1.451(4) C4 C11 1.508(4) C5 C6 1.357(4) C5 C101 1.417(4) C5 H5 .9300 C6 C7 1.398(4) C6 H6 .9300 C7 C8 1.365(4) C7 H7 .9300 C8 C81 1.416(4) C8 H8 .9300 C9 C91 1.374(3) C9 C81 1.404(4) C10 C41 1.398(4) C10 C101 1.406(4) C11 H11A .9600 C11 H11B .9600 C11 H11C .9600 C12 H12A .9600 C12 H12B .9600 C12 H12C .9600 C13 H13A .9600 C13 H13B .9600 C13 H13C .9600 C41 C91 1.423(3) C81 C101 1.417(3) 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 N1 H1 O2 2_666 .86 2.10 2.941(4) 164.3 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 C91 N1 C2 O2 178.4(2) C91 N1 C2 C3 -2.0(3) O2 C2 C3 C4 -178.2(2) N1 C2 C3 C4 2.2(4) C2 C3 C4 C41 -.9(4) C2 C3 C4 C11 -179.9(2) C101 C5 C6 C7 -.1(4) C5 C6 C7 C8 2.2(4) C6 C7 C8 C81 -1.4(4) C12 O1 C9 C91 95.8(2) C12 O1 C9 C81 -85.0(2) C13 O3 C10 C41 102.3(3) C13 O3 C10 C101 -80.4(3) O3 C10 C41 C91 175.73(17) C101 C10 C41 C91 -1.5(3) O3 C10 C41 C4 -2.3(3) C101 C10 C41 C4 -179.5(2) C3 C4 C41 C10 177.3(2) C11 C4 C41 C10 -3.7(4) C3 C4 C41 C91 -.7(3) C11 C4 C41 C91 178.2(2) O1 C9 C81 C8 .0(3) C91 C9 C81 C8 179.1(2) O1 C9 C81 C101 179.19(18) C91 C9 C81 C101 -1.7(3) C7 C8 C81 C9 177.6(2) C7 C8 C81 C101 -1.6(3) O1 C9 C91 N1 -2.0(3) C81 C9 C91 N1 178.85(18) O1 C9 C91 C41 177.16(17) C81 C9 C91 C41 -2.0(3) C2 N1 C91 C9 179.7(2) C2 N1 C91 C41 .5(3) C10 C41 C91 C9 3.5(3) C4 C41 C91 C9 -178.24(19) C10 C41 C91 N1 -177.30(17) C4 C41 C91 N1 .9(3) O3 C10 C101 C5 -.1(3) C41 C10 C101 C5 177.21(19) O3 C10 C101 C81 -179.29(17) C41 C10 C101 C81 -2.0(3) C6 C5 C101 C10 178.0(2) C6 C5 C101 C81 -2.8(3) C9 C81 C101 C10 3.6(3) C8 C81 C101 C10 -177.1(2) C9 C81 C101 C5 -175.63(19) C8 C81 C101 C5 3.6(3)