#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/25/2012594.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_2012594 loop_ _publ_author_name 'Zolotoy, Alexander B.' 'Botoshansky, Mark' 'Kaftory, Menahem' _publ_section_title ; 1-Methyl-5,6,7,8-tetrahydroquinoxalin-2(1H)-one ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o148 _journal_page_last o150 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C9 H12 N2 O' _chemical_formula_moiety 'C9 H12 N2 O' _chemical_formula_sum 'C9 H12 N2 O' _chemical_formula_weight 164.21 _chemical_name_common monlow _chemical_name_systematic ; ? ; _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 93.75(3) _cell_angle_beta 97.13(3) _cell_angle_gamma 102.56(2) _cell_formula_units_Z 4 _cell_length_a 6.7910(10) _cell_length_b 11.170(2) _cell_length_c 11.246(2) _cell_measurement_reflns_used 3833 _cell_measurement_temperature 140 _cell_measurement_theta_max 26.4 _cell_measurement_theta_min 1.7 _cell_volume 822.4(3) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293 _diffrn_measured_fraction_theta_full .961 _diffrn_measured_fraction_theta_max .961 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f and \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 .055 _diffrn_reflns_av_sigmaI/netI .1017 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 8459 _diffrn_reflns_theta_full 27.83 _diffrn_reflns_theta_max 27.83 _diffrn_reflns_theta_min 1.83 _diffrn_standards_number no _exptl_absorpt_coefficient_mu .089 _exptl_absorpt_correction_T_max .9824 _exptl_absorpt_correction_T_min .9738 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 352 _exptl_crystal_size_max .20 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .08 _refine_diff_density_max .266 _refine_diff_density_min -.247 _refine_ls_extinction_coef .060(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref .905 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 314 _refine_ls_number_reflns 3751 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .905 _refine_ls_R_factor_all .1277 _refine_ls_R_factor_gt .0546 _refine_ls_shift/su_max .002 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .1288 _refine_ls_wR_factor_ref .1692 _reflns_number_gt 2056 _reflns_number_total 3751 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file oa1127.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: '_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_database_code 2012594 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 O1A .2239(3) -.17856(15) 1.11151(15) .0375(5) Uani d . 1 . . O N1A .2699(3) .02797(17) 1.08888(15) .0252(5) Uani d . 1 . . N N2A .2279(3) -.02539(18) .84358(17) .0309(5) Uani d . 1 . . N C1A .2356(3) -.0945(2) 1.0443(2) .0270(5) Uani d . 1 . . C C2A .2766(3) .12215(19) 1.01429(19) .0240(5) Uani d . 1 . . C C3A .2582(3) .0945(2) .89320(19) .0268(5) Uani d . 1 . . C C4A .2171(4) -.1128(2) .9151(2) .0293(6) Uani d . 1 . . C C5A .3014(5) .0536(3) 1.2208(2) .0382(7) Uani d . 1 . . C C6A .2737(4) .1916(2) .8069(2) .0369(6) Uani d . 1 . . C C7A .3755(5) .3187(2) .8697(3) .0424(7) Uani d . 1 . . C C8A .2731(4) .3420(2) .9791(3) .0405(7) Uani d . 1 . . C C9A .3055(4) .2518(2) 1.0712(2) .0334(6) Uani d . 1 . . C O1B .2489(3) .63679(14) .74832(15) .0386(5) Uani d . 1 . . O N1B .0070(3) .45958(16) .68387(15) .0251(5) Uani d . 1 . . N N2B .2531(3) .39788(17) .52403(16) .0291(5) Uani d . 1 . . N C1B .1914(3) .5396(2) .6813(2) .0275(5) Uani d . 1 . . C C2B -.0592(3) .35216(19) .60677(19) .0253(5) Uani d . 1 . . C C3B .0674(3) .3220(2) .53033(19) .0265(5) Uani d . 1 . . C C4B .3102(4) .5000(2) .5948(2) .0301(6) Uani d . 1 . . C C5B -.1193(4) .4905(3) .7740(3) .0371(6) Uani d . 1 . . C C6B .0132(4) .2033(2) .4490(2) .0323(6) Uani d . 1 . . C C7B -.1658(4) .1123(2) .4837(2) .0359(6) Uani d . 1 . . C C8B -.3362(4) .1764(2) .5046(2) .0344(6) Uani d . 1 . . C C9B -.2681(4) .2749(2) .6111(2) .0295(6) Uani d . 1 . . C H4A1 .204(4) -.197(2) .882(2) .041(7) Uiso d . 1 . . H H5A1 .164(5) .055(3) 1.252(3) .074(10) Uiso d . 1 . . H H5A2 .346(4) -.015(2) 1.255(2) .045(8) Uiso d . 1 . . H H5A3 .395(5) .132(3) 1.245(3) .062(9) Uiso d . 1 . . H H6A1 .134(4) .189(2) .768(2) .050(8) Uiso d . 1 . . H H6A2 .351(4) .171(2) .742(2) .045(7) Uiso d . 1 . . H H7A1 .525(5) .319(2) .902(3) .059(9) Uiso d . 1 . . H H7A2 .367(5) .384(3) .814(3) .062(9) Uiso d . 1 . . H H8A1 .117(5) .329(2) .955(2) .048(8) Uiso d . 1 . . H H8A2 .325(4) .427(3) 1.016(2) .051(8) Uiso d . 1 . . H H9A1 .212(4) .251(2) 1.137(2) .046(7) Uiso d . 1 . . H H9A2 .439(4) .273(2) 1.117(2) .040(7) Uiso d . 1 . . H H4B1 .447(5) .558(3) .590(2) .058(9) Uiso d . 1 . . H H5B1 -.020(5) .553(3) .831(3) .058(9) Uiso d . 1 . . H H5B2 -.229(5) .524(3) .733(3) .062(9) Uiso d . 1 . . H H5B3 -.173(5) .416(3) .812(3) .069(10) Uiso d . 1 . . H H6B1 .145(4) .170(2) .4508(19) .027(6) Uiso d . 1 . . H H6B2 -.014(4) .226(2) .368(2) .042(7) Uiso d . 1 . . H H7B1 -.212(4) .042(2) .418(2) .042(7) Uiso d . 1 . . H H7B2 -.123(4) .071(2) .561(2) .039(7) Uiso d . 1 . . H H8B1 -.372(4) .215(2) .431(2) .043(7) Uiso d . 1 . . H H8B2 -.463(4) .119(2) .522(2) .046(7) Uiso d . 1 . . H H9B1 -.363(4) .331(2) .611(2) .034(7) Uiso d . 1 . . H H9B2 -.259(3) .241(2) .689(2) .028(6) 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 O1A .0346(10) .0372(10) .0454(10) .0118(8) .0099(8) .0178(8) N1A .0229(10) .0304(10) .0220(9) .0047(8) .0054(7) .0017(8) N2A .0277(12) .0358(11) .0291(10) .0083(9) .0045(8) -.0022(9) C1A .0171(12) .0301(12) .0346(13) .0068(10) .0039(9) .0045(10) C2A .0184(12) .0262(12) .0269(11) .0048(9) .0020(9) .0017(9) C3A .0219(12) .0314(13) .0281(12) .0080(10) .0029(9) .0040(10) C4A .0242(13) .0308(13) .0337(13) .0094(10) .0046(10) -.0023(11) C5A .0438(17) .0495(17) .0202(12) .0106(14) .0011(11) .0024(12) C6A .0377(16) .0421(15) .0337(14) .0120(13) .0063(12) .0127(11) C7A .0408(18) .0367(15) .0552(17) .0127(13) .0114(13) .0218(13) C8A .0334(16) .0296(14) .0600(18) .0070(12) .0119(13) .0067(13) C9A .0294(15) .0309(13) .0387(14) .0057(11) .0060(12) -.0029(11) O1B .0393(11) .0296(9) .0413(10) .0023(8) -.0005(8) -.0063(8) N1B .0266(11) .0237(10) .0253(10) .0064(8) .0050(8) .0005(8) N2B .0282(11) .0296(10) .0302(10) .0056(9) .0083(8) .0026(8) C1B .0244(13) .0262(12) .0307(12) .0059(10) -.0006(9) .0014(10) C2B .0267(13) .0245(11) .0247(11) .0062(10) .0028(9) .0037(9) C3B .0283(13) .0254(12) .0269(12) .0063(10) .0063(9) .0049(9) C4B .0261(14) .0295(13) .0351(13) .0058(11) .0057(10) .0054(11) C5B .0367(16) .0384(15) .0372(14) .0101(13) .0114(12) -.0062(13) C6B .0423(16) .0300(13) .0257(13) .0095(11) .0076(11) .0005(10) C7B .0469(17) .0256(13) .0323(13) .0046(12) .0046(11) -.0031(11) C8B .0321(15) .0300(13) .0363(14) -.0011(11) .0023(11) .0005(11) C9B .0288(14) .0301(13) .0298(13) .0058(11) .0043(10) .0068(10) 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 O1A C1A . 1.239(3) ? N1A C2A . 1.384(3) ? N1A C1A . 1.386(3) ? N1A C5A . 1.472(3) ? N2A C4A . 1.301(3) ? N2A C3A . 1.379(3) ? C1A C4A . 1.440(3) ? C2A C3A . 1.361(3) ? C2A C9A . 1.507(3) ? C3A C6A . 1.497(3) ? C4A H4A1 . .97(2) ? C5A H5A1 . 1.04(4) ? C5A H5A2 . .97(3) ? C5A H5A3 . .96(3) ? C6A C7A . 1.520(4) ? C6A H6A1 . .99(3) ? C6A H6A2 . 1.00(3) ? C7A C8A . 1.522(4) ? C7A H7A1 . 1.03(3) ? C7A H7A2 . 1.00(3) ? C8A C9A . 1.520(4) ? C8A H8A1 . 1.04(3) ? C8A H8A2 . .98(3) ? C9A H9A1 . 1.04(3) ? C9A H9A2 . .96(3) ? O1B C1B . 1.239(2) ? N1B C1B . 1.376(3) ? N1B C2B . 1.388(3) ? N1B C5B . 1.477(3) ? N2B C4B . 1.303(3) ? N2B C3B . 1.371(3) ? C1B C4B . 1.444(3) ? C2B C3B . 1.365(3) ? C2B C9B . 1.500(3) ? C3B C6B . 1.508(3) ? C4B H4B1 . 1.02(3) ? C5B H5B1 . .99(3) ? C5B H5B2 . .98(3) ? C5B H5B3 . .99(3) ? C6B C7B . 1.515(4) ? C6B H6B1 . 1.04(2) ? C6B H6B2 . .97(3) ? C7B C8B . 1.521(4) ? C7B H7B1 . 1.01(3) ? C7B H7B2 . 1.05(3) ? C8B C9B . 1.526(3) ? C8B H8B1 . .99(3) ? C8B H8B2 . 1.01(3) ? C9B H9B1 . 1.00(3) ? C9B H9B2 . .98(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 C2A N1A C1A 122.27(17) C2A N1A C5A 121.24(19) C1A N1A C5A 116.5(2) C4A N2A C3A 118.63(19) O1A C1A N1A 121.9(2) O1A C1A C4A 124.4(2) N1A C1A C4A 113.7(2) C3A C2A N1A 119.07(19) C3A C2A C9A 122.6(2) N1A C2A C9A 118.29(19) C2A C3A N2A 121.3(2) C2A C3A C6A 122.3(2) N2A C3A C6A 116.35(19) N2A C4A C1A 124.9(2) N2A C4A H4A1 119.5(15) C1A C4A H4A1 115.4(15) N1A C5A H5A1 110.8(17) N1A C5A H5A2 107.9(15) H5A1 C5A H5A2 105(2) N1A C5A H5A3 110.2(19) H5A1 C5A H5A3 109(2) H5A2 C5A H5A3 114(2) C3A C6A C7A 111.8(2) C3A C6A H6A1 107.3(16) C7A C6A H6A1 111.2(15) C3A C6A H6A2 109.7(15) C7A C6A H6A2 110.0(15) H6A1 C6A H6A2 107(2) C6A C7A C8A 109.2(2) C6A C7A H7A1 108.1(15) C8A C7A H7A1 106.5(16) C6A C7A H7A2 110.9(16) C8A C7A H7A2 110.2(17) H7A1 C7A H7A2 112(3) C9A C8A C7A 110.6(2) C9A C8A H8A1 106.9(15) C7A C8A H8A1 110.7(14) C9A C8A H8A2 109.6(16) C7A C8A H8A2 111.2(17) H8A1 C8A H8A2 108(2) C2A C9A C8A 112.5(2) C2A C9A H9A1 108.9(14) C8A C9A H9A1 112.6(15) C2A C9A H9A2 106.3(15) C8A C9A H9A2 113.1(16) H9A1 C9A H9A2 103(2) C1B N1B C2B 122.10(19) C1B N1B C5B 117.58(19) C2B N1B C5B 120.3(2) C4B N2B C3B 118.6(2) O1B C1B N1B 122.2(2) O1B C1B C4B 123.5(2) N1B C1B C4B 114.28(19) C3B C2B N1B 118.8(2) C3B C2B C9B 123.1(2) N1B C2B C9B 118.1(2) C2B C3B N2B 121.7(2) C2B C3B C6B 122.3(2) N2B C3B C6B 116.0(2) N2B C4B C1B 124.5(2) N2B C4B H4B1 119.6(15) C1B C4B H4B1 115.9(15) N1B C5B H5B1 102.2(17) N1B C5B H5B2 108.5(18) H5B1 C5B H5B2 112(2) N1B C5B H5B3 108.7(17) H5B1 C5B H5B3 112(2) H5B2 C5B H5B3 112(3) C3B C6B C7B 112.1(2) C3B C6B H6B1 106.9(12) C7B C6B H6B1 113.6(13) C3B C6B H6B2 105.8(14) C7B C6B H6B2 112.3(15) H6B1 C6B H6B2 105(2) C6B C7B C8B 110.1(2) C6B C7B H7B1 108.6(15) C8B C7B H7B1 112.1(15) C6B C7B H7B2 111.4(14) C8B C7B H7B2 109.8(14) H7B1 C7B H7B2 104.7(19) C7B C8B C9B 110.8(2) C7B C8B H8B1 107.9(15) C9B C8B H8B1 109.5(14) C7B C8B H8B2 113.5(15) C9B C8B H8B2 107.0(14) H8B1 C8B H8B2 108(2) C2B C9B C8B 111.7(2) C2B C9B H9B1 107.6(14) C8B C9B H9B1 110.6(13) C2B C9B H9B2 105.0(14) C8B C9B H9B2 113.4(13) H9B1 C9B H9B2 108.3(19) 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 C2A N1A C1A O1A -177.8(2) C5A N1A C1A O1A 2.8(3) C2A N1A C1A C4A 2.6(3) C5A N1A C1A C4A -176.8(2) C1A N1A C2A C3A -3.1(3) C5A N1A C2A C3A 176.3(2) C1A N1A C2A C9A 177.3(2) C5A N1A C2A C9A -3.3(3) N1A C2A C3A N2A 1.7(3) C9A C2A C3A N2A -178.7(2) N1A C2A C3A C6A -177.1(2) C9A C2A C3A C6A 2.5(3) C4A N2A C3A C2A .0(3) C4A N2A C3A C6A 178.8(2) C3A N2A C4A C1A -.4(3) O1A C1A C4A N2A 179.6(2) N1A C1A C4A N2A -.9(3) C2A C3A C6A C7A 18.0(3) N2A C3A C6A C7A -160.8(2) C3A C6A C7A C8A -50.3(3) C6A C7A C8A C9A 64.2(3) C3A C2A C9A C8A 10.4(3) N1A C2A C9A C8A -170.0(2) C7A C8A C9A C2A -43.3(3) C2B N1B C1B O1B 178.5(2) C5B N1B C1B O1B -2.6(3) C2B N1B C1B C4B -1.7(3) C5B N1B C1B C4B 177.2(2) C1B N1B C2B C3B 3.4(3) C5B N1B C2B C3B -175.5(2) C1B N1B C2B C9B -176.2(2) C5B N1B C2B C9B 4.9(3) N1B C2B C3B N2B -3.1(3) C9B C2B C3B N2B 176.5(2) N1B C2B C3B C6B 176.2(2) C9B C2B C3B C6B -4.2(4) C4B N2B C3B C2B 1.2(3) C4B N2B C3B C6B -178.1(2) C3B N2B C4B C1B .5(3) O1B C1B C4B N2B 179.6(2) N1B C1B C4B N2B -.2(3) C2B C3B C6B C7B -13.7(3) N2B C3B C6B C7B 165.6(2) C3B C6B C7B C8B 46.6(3) C6B C7B C8B C9B -63.9(3) C3B C2B C9B C8B -11.8(3) N1B C2B C9B C8B 167.8(2) C7B C8B C9B C2B 45.0(3) _cod_database_fobs_code 2012594 _journal_paper_doi 10.1107/S0108270102001087