#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/22/2202223.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_2202223 loop_ _publ_author_name 'Sheng-Lou Deng' 'Ru-Yu Chen' 'Xue-Bing Leng' 'Lin-Hong Weng' _publ_section_title 5-Ethyl-6-oxo-4-thioxo-1,3,2-oxazaphospholidino[3,2-a][1,3,2]benzodiazaphosphorine _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o285 _journal_page_last o287 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C11 H13 N2 O2 P S' _chemical_formula_moiety 'C11 H13 N2 O2 P S' _chemical_formula_sum 'C11 H13 N2 O2 P S' _chemical_formula_weight 268.26 _chemical_melting_point 384 _chemical_name_systematic ; 5-Ethyl-6-oxo-4-thioxo-1,3,2- oxazaphospholidino[3,2-a][1,3,2]benzodiazaphosphorine ; _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 61.633(2) _cell_angle_beta 78.828(2) _cell_angle_gamma 83.139(2) _cell_formula_units_Z 2 _cell_length_a 6.9347(7) _cell_length_b 9.9827(10) _cell_length_c 10.4868(11) _cell_measurement_reflns_used 231 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 22.80 _cell_measurement_theta_min 2.80 _cell_volume 626.38(11) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction 'SHELXTL (Bruker, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-7 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker 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 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 2621 _diffrn_reflns_theta_full 25.02 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 2.23 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.377 _exptl_absorpt_correction_T_max 0.927 _exptl_absorpt_correction_T_min 0.564 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 280 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.441 _refine_diff_density_min -0.286 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 2208 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0414 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0718P)^2^+0.2182P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1127 _refine_ls_wR_factor_ref 0.1184 _reflns_number_gt 1940 _reflns_number_total 2208 _reflns_threshold_expression I>2\s(1) _[local]_cod_data_source_file ww6058.cif _[local]_cod_data_source_block 2 _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 2202223 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 P1 0.06801(8) 0.80308(6) 0.79721(6) 0.0400(2) Uani d . 1 . . P S1 0.26105(11) 0.69681(8) 0.71926(8) 0.0618(2) Uani d . 1 . . S N1 0.0079(2) 0.98408(19) 0.6938(2) 0.0389(4) Uani d . 1 . . N N2 0.1231(3) 0.80694(19) 0.94467(19) 0.0370(4) Uani d . 1 . . N O1 -0.1457(3) 0.73971(18) 0.8365(2) 0.0553(5) Uani d . 1 . . O O2 0.2619(2) 0.92484(17) 1.04101(17) 0.0478(4) Uani d . 1 . . O C1 0.1140(3) 1.1021(2) 0.6810(2) 0.0366(5) Uani d . 1 . . C C2 0.1124(4) 1.2465(3) 0.5611(3) 0.0487(6) Uani d . 1 . . C H2A 0.0372 1.2669 0.4891 0.058 Uiso calc R 1 . . H C3 0.2226(4) 1.3591(3) 0.5493(3) 0.0561(6) Uani d . 1 . . C H3A 0.2189 1.4560 0.4701 0.067 Uiso calc R 1 . . H C4 0.3392(4) 1.3299(3) 0.6543(3) 0.0530(6) Uani d . 1 . . C H4A 0.4175 1.4052 0.6433 0.064 Uiso calc R 1 . . H C5 0.3374(3) 1.1884(3) 0.7744(3) 0.0430(5) Uani d . 1 . . C H5A 0.4141 1.1690 0.8453 0.052 Uiso calc R 1 . . H C6 0.2228(3) 1.0737(2) 0.7917(2) 0.0347(4) Uani d . 1 . . C C7 0.2058(3) 0.9315(2) 0.9349(2) 0.0347(4) Uani d . 1 . . C C8 -0.1996(3) 1.0010(3) 0.6726(3) 0.0468(6) Uani d . 1 . . C H8A -0.2102 1.0033 0.5807 0.056 Uiso calc R 1 . . H H8B -0.2600 1.0937 0.6728 0.056 Uiso calc R 1 . . H C9 -0.2951(3) 0.8625(3) 0.8012(3) 0.0539(6) Uani d . 1 . . C H9A -0.3404 0.8821 0.8845 0.065 Uiso calc R 1 . . H H9B -0.4068 0.8356 0.7759 0.065 Uiso calc R 1 . . H C10 0.1155(3) 0.6633(2) 1.0859(3) 0.0458(5) Uani d . 1 . . C H10A 0.0252 0.5955 1.0870 0.055 Uiso calc R 1 . . H H10B 0.0641 0.6869 1.1661 0.055 Uiso calc R 1 . . H C11 0.3120(4) 0.5822(3) 1.1112(3) 0.0571(6) Uani d . 1 . . C H11A 0.2974 0.4910 1.2034 0.086 Uiso calc R 1 . . H H11B 0.4015 0.6475 1.1128 0.086 Uiso calc R 1 . . H H11C 0.3626 0.5561 1.0336 0.086 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 P1 0.0423(3) 0.0377(3) 0.05(6) 0.0003(2) -0.0154(2) -0.0236(3) S1 0.0722(5) 0.0643(4) 0.0704(5) 0.0241(3) -0.0284(4) -0.0482(4) N1 0.0352(9) 0.0402(10) 0.0464(10) 0.0015(7) -0.0149(7) -0.0217(8) N2 0.0393(9) 0.0336(9) 0.0401(9) -0.0027(7) -0.0090(7) -0.0173(8) O1 0.0529(10) 0.0480(9) 0.0706(12) -0.0096(8) -0.0199(8) -0.0266(9) O2 0.0617(10) 0.0467(9) 0.0433(9) -0.0040(7) -0.0186(7) -0.0232(7) C1 0.0341(10) 0.0385(11) 0.0391(11) 0.0002(8) -0.0050(8) -0.0201(9) C2 0.0542(14) 0.0473(13) 0.0404(12) -0.0027(11) -0.0120(10) -0.0150(10) C3 0.0648(16) 0.0425(13) 0.0475(13) -0.0075(12) -0.0064(11) -0.0098(11) C4 0.0525(14) 0.0456(13) 0.0576(15) -0.0166(11) -0.0006(11) -0.0208(11) C5 0.0385(11) 0.0441(12) 0.0487(13) -0.0067(9) -0.0055(9) -0.0228(10) C6 0.0308(10) 0.0369(11) 0.0378(11) 0.0000(8) -0.0039(8) -0.0193(9) C7 0.0292(10) 0.0373(10) 0.0401(11) 0.0002(8) -0.0059(8) -0.0201(9) C8 0.0357(11) 0.0575(14) 0.0539(13) 0.0035(10) -0.0168(10) -0.0287(12) C9 0.0410(13) 0.0673(16) 0.0661(16) -0.0062(11) -0.0113(11) -0.0391(14) C10 0.0522(13) 0.0377(11) 0.0439(12) -0.0063(10) -0.0063(10) -0.0154(10) C11 0.0637(16) 0.0437(13) 0.0572(15) 0.0071(11) -0.0180(12) -0.0170(11) 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 P1 O1 . 1.5827(17) ? P1 N1 . 1.6577(18) ? P1 N2 . 1.6815(18) ? P1 S1 . 1.9095(9) ? N1 C1 . 1.402(3) ? N1 C8 . 1.476(3) ? N2 C7 . 1.383(3) ? N2 C10 . 1.491(3) ? O1 C9 . 1.459(3) ? O2 C7 . 1.218(3) ? C1 C2 . 1.393(3) ? C1 C6 . 1.404(3) ? C2 C3 . 1.378(4) ? C2 H2A . 0.9300 ? C3 C4 . 1.390(4) ? C3 H3A . 0.9300 ? C4 C5 . 1.374(3) ? C4 H4A . 0.9300 ? C5 C6 . 1.393(3) ? C5 H5A . 0.9300 ? C6 C7 . 1.493(3) ? C8 C9 . 1.506(4) ? C8 H8A . 0.9700 ? C8 H8B . 0.9700 ? C9 H9A . 0.9700 ? C9 H9B . 0.9700 ? C10 C11 . 1.502(3) ? C10 H10A . 0.9700 ? C10 H10B . 0.9700 ? C11 H11A . 0.9600 ? C11 H11B . 0.9600 ? C11 H11C . 0.9600 ? 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' P P 0.1023 0.0942 '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 O1 P1 N1 96.62(9) O1 P1 N2 108.83(10) N1 P1 N2 102.08(9) O1 P1 S1 113.05(7) N1 P1 S1 120.73(8) N2 P1 S1 113.68(7) C1 N1 C8 123.70(17) C1 N1 P1 121.12(14) C8 N1 P1 110.81(14) C7 N2 C10 117.76(17) C7 N2 P1 122.34(14) C10 N2 P1 119.04(14) C9 O1 P1 111.43(14) C2 C1 N1 121.13(19) C2 C1 C6 119.7(2) N1 C1 C6 119.21(18) C3 C2 C1 119.9(2) C3 C2 H2A 120.1 C1 C2 H2A 120.1 C2 C3 C4 120.9(2) C2 C3 H3A 119.6 C4 C3 H3A 119.6 C5 C4 C3 119.3(2) C5 C4 H4A 120.4 C3 C4 H4A 120.4 C4 C5 C6 121.1(2) C4 C5 H5A 119.4 C6 C5 H5A 119.4 C5 C6 C1 119.04(19) C5 C6 C7 117.71(18) C1 C6 C7 122.95(18) O2 C7 N2 120.52(19) O2 C7 C6 121.29(18) N2 C7 C6 118.18(18) N1 C8 C9 104.33(18) N1 C8 H8A 110.9 C9 C8 H8A 110.9 N1 C8 H8B 110.9 C9 C8 H8B 110.9 H8A C8 H8B 108.9 O1 C9 C8 106.62(19) O1 C9 H9A 110.4 C8 C9 H9A 110.4 O1 C9 H9B 110.4 C8 C9 H9B 110.4 H9A C9 H9B 108.6 N2 C10 C11 113.49(19) N2 C10 H10A 108.9 C11 C10 H10A 108.9 N2 C10 H10B 108.9 C11 C10 H10B 108.9 H10A C10 H10B 107.7 C10 C11 H11A 109.5 C10 C11 H11B 109.5 H11A C11 H11B 109.5 C10 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 _cod_database_fobs_code 2202223