#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/35/2203503.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_2203503 loop_ _publ_author_name 'Baranac, Marija' 'Markovi\'c, Rade' 'Steel, Peter J.' _publ_section_title ; Ethyl (E)-2-(4-oxo-1,3-thiazinan-2-ylidene)ethanoate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o484 _journal_page_last o485 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C8 H11 N O3 S' _chemical_formula_moiety 'C8 H11 N O3 S' _chemical_formula_sum 'C8 H11 N O3 S' _chemical_formula_weight 201.24 _chemical_name_common (1) _chemical_name_systematic ; Ethyl (E)-2-(4-oxo-1,3-thiazinan-2-ylidene)ethanoate ; _space_group_IT_number 13 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yac' _symmetry_space_group_name_H-M 'P 1 2/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90 _cell_angle_beta 102.7030(10) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 14.0313(8) _cell_length_b 9.1124(5) _cell_length_c 15.0553(9) _cell_measurement_reflns_used 9581 _cell_measurement_temperature 163(2) _cell_measurement_theta_max 26.4 _cell_measurement_theta_min 2.2 _cell_volume 1877.84(19) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 163(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _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 0.71073 _diffrn_reflns_av_R_equivalents 0.020 _diffrn_reflns_av_sigmaI/netI 0.015 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 21284 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 1.8 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.319 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_correction_T_min 0.817 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2002)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 848 _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.55 _refine_diff_density_min -0.20 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 241 _refine_ls_number_reflns 3298 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.04 _refine_ls_R_factor_all 0.048 _refine_ls_R_factor_gt 0.035 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0536P)^2^+0.688P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.093 _refine_ls_wR_factor_ref 0.099 _reflns_number_gt 2573 _reflns_number_total 3298 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file tk6154.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 2/n' _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_enum 1527 2010-12-29 10:47:43Z saulius 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_database_code 2203503 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, 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 S1 0.60870(4) 0.30099(5) 0.20123(3) 0.03225(15) Uani d . 1 S C2 0.62315(13) 0.4885(2) 0.18357(12) 0.0260(4) Uani d . 1 C N3 0.63322(11) 0.53770(18) 0.09900(10) 0.0294(4) Uani d . 1 N H3 0.6414(15) 0.629(2) 0.0908(14) 0.035 Uiso d . 1 H C4 0.62288(14) 0.4626(2) 0.01829(13) 0.0311(4) Uani d . 1 C O4 0.62529(12) 0.53068(15) -0.05094(9) 0.0433(4) Uani d . 1 O C5 0.60761(16) 0.2997(2) 0.01885(13) 0.0355(5) Uani d . 1 C H5A 0.6335 0.2553 -0.0310 0.043 Uiso calc R 1 H H5B 0.5366 0.2793 0.0066 0.043 Uiso calc R 1 H C6 0.65659(15) 0.2274(2) 0.10823(13) 0.0330(4) Uani d . 1 C H6A 0.7280 0.2445 0.1201 0.040 Uiso calc R 1 H H6B 0.6451 0.1202 0.1039 0.040 Uiso calc R 1 H C7 0.62163(13) 0.5825(2) 0.25266(13) 0.0276(4) Uani d . 1 C H7A 0.6173 0.5428 0.3100 0.033 Uiso calc R 1 H C8 0.62620(13) 0.7406(2) 0.24384(13) 0.0294(4) Uani d . 1 C O8 0.63644(10) 0.80890(14) 0.17631(9) 0.0353(3) Uani d . 1 O O9 0.61747(10) 0.80803(14) 0.32122(9) 0.0326(3) Uani d . 1 O C9 0.62474(16) 0.9667(2) 0.32183(15) 0.0381(5) Uani d . 1 C H9A 0.5787 1.0085 0.2684 0.046 Uiso calc R 1 H H9B 0.6918 0.9972 0.3194 0.046 Uiso calc R 1 H C10 0.59991(18) 1.0199(2) 0.40825(16) 0.0475(6) Uani d . 1 C H10A 0.6042 1.1272 0.4109 0.071 Uiso calc R 1 H H10B 0.6460 0.9779 0.4606 0.071 Uiso calc R 1 H H10C 0.5333 0.9893 0.4098 0.071 Uiso calc R 1 H S1A 0.60498(4) 0.62341(6) -0.30573(4) 0.03881(17) Uani d . 1 S C2A 0.62593(13) 0.4363(2) -0.31933(12) 0.0274(4) Uani d . 1 C N3A 0.64413(12) 0.38579(19) -0.40124(11) 0.0315(4) Uani d . 1 N H3A 0.6502(16) 0.300(3) -0.4106(15) 0.038 Uiso d . 1 H C4A 0.64723(14) 0.4616(2) -0.47922(13) 0.0336(5) Uani d . 1 C O4A 0.65902(12) 0.39316(16) -0.54559(10) 0.0451(4) Uani d . 1 O C5A 0.63412(19) 0.6243(2) -0.48033(15) 0.0483(6) Uani d . 1 C H5AA 0.6718 0.6673 -0.5223 0.058 Uiso calc R 1 H H5AB 0.5643 0.6467 -0.5051 0.058 Uiso calc R 1 H C6A 0.66513(18) 0.6969(2) -0.38999(15) 0.0475(6) Uani d . 1 C H6AA 0.6510 0.8032 -0.3970 0.057 Uiso calc R 1 H H6AB 0.7366 0.6852 -0.3683 0.057 Uiso calc R 1 H C7A 0.62013(13) 0.3442(2) -0.25037(13) 0.0295(4) Uani d . 1 C H7AA 0.6099 0.3850 -0.1951 0.035 Uiso calc R 1 H C8A 0.62874(13) 0.1860(2) -0.25664(13) 0.0289(4) Uani d . 1 C O8A 0.64304(10) 0.11637(15) -0.32198(9) 0.0355(3) Uani d . 1 O O9A 0.61916(10) 0.12133(14) -0.17883(9) 0.0340(3) Uani d . 1 O C9A 0.63124(15) -0.0371(2) -0.17390(14) 0.0369(5) Uani d . 1 C H9AA 0.6973 -0.0648 -0.1813 0.044 Uiso calc R 1 H H9AB 0.5822 -0.0853 -0.2225 0.044 Uiso calc R 1 H C10A 0.61728(17) -0.0830(2) -0.08178(15) 0.0454(6) Uani d . 1 C H10D 0.6247 -0.1896 -0.0754 0.068 Uiso calc R 1 H H10E 0.5517 -0.0547 -0.0754 0.068 Uiso calc R 1 H H10F 0.6663 -0.0345 -0.0344 0.068 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 S1 0.0442(3) 0.0238(3) 0.0315(3) 0.0021(2) 0.0144(2) 0.0034(2) C2 0.0230(9) 0.0287(10) 0.0261(10) 0.0026(7) 0.0052(7) 0.0047(8) N3 0.0363(9) 0.0243(8) 0.0286(9) 0.0025(7) 0.0095(7) 0.0030(7) C4 0.0365(11) 0.0315(10) 0.0254(10) 0.0093(9) 0.0066(8) 0.0034(8) O4 0.0688(10) 0.0339(8) 0.0281(8) 0.0087(7) 0.0123(7) 0.0068(6) C5 0.0512(12) 0.0277(10) 0.0279(11) 0.0037(9) 0.0092(9) -0.0012(8) C6 0.0423(11) 0.0265(10) 0.0318(11) 0.0072(9) 0.0116(9) 0.0015(8) C7 0.0299(10) 0.0272(10) 0.0261(10) -0.0005(8) 0.0069(8) 0.0020(8) C8 0.0245(10) 0.0334(11) 0.0294(10) -0.0020(8) 0.0041(8) -0.0021(9) O8 0.0427(8) 0.0281(8) 0.0361(8) 0.85(2)-0.0027(6) 0.0110(6) 0.0037(6) O9 0.0410(8) 0.0238(7) 0.0334(8) -0.0038(6) 0.0091(6) -0.0030(6) C9 0.0458(12) 0.0228(10) 0.0451(13) -0.0038(9) 0.0083(10) -0.0034(9) C10 0.0576(14) 0.0322(12) 0.0526(14) -0.0066(10) 0.0117(11) -0.0115(10) S1A 0.0500(3) 0.0282(3) 0.0433(3) 0.0023(2) 0.0213(3) -0.0018(2) C2A 0.0229(9) 0.0314(10) 0.0281(10) -0.0021(8) 0.0062(8) -0.0041(8) N3A 0.0367(9) 0.0298(9) 0.0284(9) -0.0022(8) 0.0080(7) -0.0005(7) C4A 0.0342(11) 0.0372(11) 0.0294(11) -0.0056(9) 0.0073(9) -0.0025(9) O4A 0.0633(10) 0.0426(9) 0.0313(8) -0.0073(7) 0.0146(7) -0.0050(7) C5A 0.0676(16) 0.0379(13) 0.0412(13) -0.0035(11) 0.0158(12) 0.0043(10) C6A 0.0654(15) 0.0345(13) 0.0446(13) -0.0071(11) 0.0164(11) -0.0004(10) C7A 0.0287(10) 0.0332(10) 0.0281(10) 0.0004(8) 0.0094(8) -0.0033(8) C8A 0.0246(10) 0.0332(11) 0.0289(10) 0.0013(8) 0.0058(8) -0.0003(9) O8A 0.0405(8) 0.0337(8) 0.0341(8) 0.0032(6) 0.0122(6) -0.0048(6) O9A 0.0433(8) 0.0271(7) 0.0346(8) 0.0023(6) 0.0148(6) 0.0017(6) C9A 0.0414(11) 0.0245(10) 0.0468(13) 0.0035(9) 0.0143(10) -0.0001(9) C10A 0.0567(14) 0.0303(11) 0.0531(14) 0.0008(10) 0.0203(11) 0.0060(10) 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' N N 0.0061 0.0033 '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' S S 0.1246 0.1234 '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 C2 S1 C6 99.75(9) C7 C2 N3 121.61(17) C7 C2 S1 118.71(14) N3 C2 S1 119.65(14) C4 N3 C2 129.71(17) C4 N3 H3 110.4(14) C2 N3 H3 119.5(14) O4 C4 N3 119.03(18) O4 C4 C5 122.60(17) N3 C4 C5 118.37(16) C4 C5 C6 113.38(16) C4 C5 H5A 108.9 C6 C5 H5A 108.9 C4 C5 H5B 108.9 C6 C5 H5B 108.9 H5A C5 H5B 107.7 C5 C6 S1 110.58(14) C5 C6 H6A 109.5 S1 C6 H6A 109.5 C5 C6 H6B 109.5 S1 C6 H6B 109.5 H6A C6 H6B 108.1 C2 C7 C8 123.43(17) C2 C7 H7A 118.3 C8 C7 H7A 118.3 O8 C8 O9 122.37(17) O8 C8 C7 126.54(18) O9 C8 C7 111.09(16) C8 O9 C9 116.16(15) O9 C9 C10 107.36(17) O9 C9 H9A 110.2 C10 C9 H9A 110.2 O9 C9 H9B 110.2 C10 C9 H9B 110.2 H9A C9 H9B 108.5 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 C2A S1A C6A 99.38(10) C7A C2A N3A 121.96(18) C7A C2A S1A 118.38(14) N3A C2A S1A 119.62(14) C4A N3A C2A 129.71(18) C4A N3A H3A 108.4(16) C2A N3A H3A 121.7(16) O4A C4A N3A 118.68(19) O4A C4A C5A 122.46(19) N3A C4A C5A 118.85(18) C6A C5A C4A 114.83(19) C6A C5A H5AA 108.6 C4A C5A H5AA 108.6 C6A C5A H5AB 108.6 C4A C5A H5AB 108.6 H5AA C5A H5AB 107.5 C5A C6A S1A 113.00(16) C5A C6A H6AA 109.0 S1A C6A H6AA 109.0 C5A C6A H6AB 109.0 S1A C6A H6AB 109.0 H6AA C6A H6AB 107.8 C2A C7A C8A 123.16(17) C2A C7A H7AA 118.4 C8A C7A H7AA 118.4 O8A C8A O9A 122.58(17) O8A C8A C7A 126.73(17) O9A C8A C7A 110.68(16) C8A O9A C9A 116.56(15) O9A C9A C10A 106.62(16) O9A C9A H9AA 110.4 C10A C9A H9AA 110.4 O9A C9A H9AB 110.4 C10A C9A H9AB 110.4 H9AA C9A H9AB 108.6 C9A C10A H10D 109.5 C9A C10A H10E 109.5 H10D C10A H10E 109.5 C9A C10A H10F 109.5 H10D C10A H10F 109.5 H10E C10A H10F 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C2 1.7478(19) S1 C6 1.8099(19) C2 C7 1.351(3) C2 N3 1.386(2) N3 C4 1.374(2) N3 H3 0.85(2) C4 O4 1.220(2) C4 C5 1.500(3) C5 C6 1.520(3) C5 H5A 0.9900 C5 H5B 0.9900 C6 H6A 0.9900 C6 H6B 0.9900 C7 C8 1.450(3) C7 H7A 0.9500 C8 O8 1.227(2) C8 O9 1.346(2) O9 C9 1.450(2) C9 C10 1.499(3) C9 H9A 0.9900 C9 H9B 0.9900 C10 H10A 0.9800 C10 H10B 0.9800 C10 H10C 0.9800 S1A C2A 1.7498(19) S1A C6A 1.800(2) C2A C7A 1.351(3) C2A N3A 1.392(2) N3A C4A 1.371(3) N3A H3A 0.80(2) C4A O4A 1.219(2) C4A C5A 1.494(3) C5A C6A 1.488(3) C5A H5AA 0.9900 C5A H5AB 0.9900 C6A H6AA 0.9900 C6A H6AB 0.9900 C7A C8A 1.451(3) C7A H7AA 0.9500 C8A O8A 1.224(2) C8A O9A 1.344(2) O9A C9A 1.454(2) C9A C10A 1.502(3) C9A H9AA 0.9900 C9A H9AB 0.9900 C10A H10D 0.9800 C10A H10E 0.9800 C10A H10F 0.9800 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 C6 S1 C2 C7 -161.67(15) C6 S1 C2 N3 20.04(16) C7 C2 N3 C4 -169.91(18) S1 C2 N3 C4 8.3(3) C2 N3 C4 O4 172.61(18) C2 N3 C4 C5 -6.5(3) O4 C4 C5 C6 150.20(19) N3 C4 C5 C6 -30.7(3) C4 C5 C6 S1 60.4(2) C2 S1 C6 C5 -51.59(16) N3 C2 C7 C8 2.6(3) S1 C2 C7 C8 -175.64(14) C2 C7 C8 O8 -3.6(3) C2 C7 C8 O9 176.27(17) O8 C8 O9 C9 -2.4(3) C7 C8 O9 C9 177.71(15) C8 O9 C9 C10 172.60(16) C6A S1A C2A C7A 159.23(16) C6A S1A C2A N3A -23.25(17) C7A C2A N3A C4A 176.15(19) S1A C2A N3A C4A -1.3(3) C2A N3A C4A O4A -175.74(18) C2A N3A C4A C5A 3.1(3) O4A C4A C5A C6A -153.5(2) N3A C4A C5A C6A 27.7(3) C4A C5A C6A S1A -56.1(3) C2A S1A C6A C5A 50.28(19) N3A C2A C7A C8A -2.3(3) S1A C2A C7A C8A 175.18(14) C2A C7A C8A O8A 0.9(3) C2A C7A C8A O9A -179.32(17) O8A C8A O9A C9A 2.8(3) C7A C8A O9A C9A -176.95(16) C8A O9A C9A C10A -179.95(16) _cod_database_fobs_code 2203503