####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_6c _database_code_depnum_ccdc_archive 'CCDC 717028' _audit_creation_date 2008-09-05T08:48:14-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; O-(p-chlorobenzoyl)-2-oxo-2-seleno-5,5-dimethyl-1,3,2-dioxaphosphorinan ; _chemical_formula_moiety 'C12 H14 Cl1 O4 P1 Se1' _chemical_formula_sum 'C12 H14 Cl O4 P Se' _chemical_formula_weight 367.61 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.9640(2) _cell_length_b 15.2200(3) _cell_length_c 8.8822(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.581(2) _cell_angle_gamma 90.00 _cell_volume 1481.63(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8854 _cell_measurement_theta_min 2.2854 _cell_measurement_theta_max 32.3584 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.11 _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.828 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.3952 _exptl_absorpt_correction_T_max 0.73 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 8.1883 _diffrn_orient_matrix_ub_11 0.0653667595 _diffrn_orient_matrix_ub_12 -0.0092422559 _diffrn_orient_matrix_ub_13 -0.0334782714 _diffrn_orient_matrix_ub_21 0.0114914144 _diffrn_orient_matrix_ub_22 0.0456538953 _diffrn_orient_matrix_ub_23 -0.0089164059 _diffrn_orient_matrix_ub_31 0.0444787432 _diffrn_orient_matrix_ub_32 0.0017667937 _diffrn_orient_matrix_ub_33 0.0547036699 _diffrn_measurement_device '4-axis \k geometry diffractometer' _diffrn_measurement_device_type 'KM4CCD, Oxford Diffraction' _diffrn_measurement_method '\w scans, 0.75 deg width' _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_unetI/netI 0.0191 _diffrn_reflns_number 12763 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3578 _reflns_number_gt 2992 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3578 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0773 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.094 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.107 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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' Cl Cl 0.1484 0.1585 '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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.586058(19) 0.079194(13) 0.62007(2) 0.02642(8) Uani 1 1 d . . . P1 P 0.60718(4) 0.11150(3) 0.84296(5) 0.01779(11) Uani 1 1 d . . . Cl1 Cl -0.00927(5) 0.35502(4) 1.16822(7) 0.04388(16) Uani 1 1 d . . . O3 O 0.48943(11) 0.15817(8) 0.91886(14) 0.0202(3) Uani 1 1 d . . . O4 O 0.50095(12) 0.28428(9) 0.78551(15) 0.0252(3) Uani 1 1 d . . . O1 O 0.71744(11) 0.17395(8) 0.88213(14) 0.0199(3) Uani 1 1 d . . . O2 O 0.62165(11) 0.02994(8) 0.95106(14) 0.0201(3) Uani 1 1 d . . . C1 C 0.75110(17) 0.18797(12) 1.0421(2) 0.0206(4) Uani 1 1 d . . . H1A H 0.6852 0.2208 1.0913 0.025 Uiso 1 1 calc R . . H1B H 0.8264 0.2237 1.0497 0.025 Uiso 1 1 calc R . . C2 C 0.77189(17) 0.10086(12) 1.1233(2) 0.0197(4) Uani 1 1 d . . . C3 C 0.65529(17) 0.04682(12) 1.1098(2) 0.0205(4) Uani 1 1 d . . . H3A H 0.6672 -0.0098 1.1631 0.025 Uiso 1 1 calc R . . H3B H 0.5882 0.0788 1.1583 0.025 Uiso 1 1 calc R . . C4 C 0.87796(17) 0.05057(14) 1.0549(2) 0.0271(4) Uani 1 1 d . . . H4A H 0.9531 0.0851 1.0669 0.041 Uiso 1 1 calc R . . H4B H 0.8603 0.0404 0.9475 0.041 Uiso 1 1 calc R . . H4C H 0.8883 -0.0060 1.1063 0.041 Uiso 1 1 calc R . . C5 C 0.79916(19) 0.11991(14) 1.2893(2) 0.0276(4) Uani 1 1 d . . . H5A H 0.7315 0.1534 1.3309 0.041 Uiso 1 1 calc R . . H5B H 0.8746 0.1542 1.2996 0.041 Uiso 1 1 calc R . . H5C H 0.8089 0.0644 1.3443 0.041 Uiso 1 1 calc R . . C6 C 0.44790(17) 0.24015(12) 0.87461(19) 0.0194(4) Uani 1 1 d . . . C7 C 0.33378(16) 0.26496(12) 0.9486(2) 0.0211(4) Uani 1 1 d . . . C8 C 0.29168(18) 0.35050(13) 0.9269(2) 0.0270(4) Uani 1 1 d . . . H8 H 0.3361 0.3900 0.8663 0.032 Uiso 1 1 calc R . . C9 C 0.18586(18) 0.37839(14) 0.9929(3) 0.0318(5) Uani 1 1 d . . . H9 H 0.1569 0.4366 0.9779 0.038 Uiso 1 1 calc R . . C10 C 0.12271(18) 0.31980(15) 1.0813(2) 0.0304(5) Uani 1 1 d . . . C11 C 0.16258(18) 0.23460(14) 1.1034(2) 0.0292(4) Uani 1 1 d . . . H11 H 0.1174 0.1953 1.1635 0.035 Uiso 1 1 calc R . . C12 C 0.26902(17) 0.20686(13) 1.0373(2) 0.0243(4) Uani 1 1 d . . . H12 H 0.2976 0.1485 1.0524 0.029 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.03757(14) 0.02175(12) 0.02001(12) -0.00308(7) 0.00173(8) -0.00056(8) P1 0.0200(2) 0.0138(2) 0.0197(2) 0.00018(17) 0.00323(17) -0.00113(17) Cl1 0.0243(3) 0.0537(4) 0.0540(4) -0.0265(3) 0.0075(2) 0.0015(2) O3 0.0215(6) 0.0162(6) 0.0230(7) 0.0013(5) 0.0036(5) 0.0008(5) O4 0.0274(7) 0.0191(7) 0.0294(7) 0.0049(5) 0.0059(6) 0.0001(5) O1 0.0222(6) 0.0175(6) 0.0200(6) 0.0023(5) 0.0018(5) -0.0033(5) O2 0.0238(6) 0.0133(6) 0.0232(7) 0.0007(5) 0.0039(5) -0.0017(5) C1 0.0245(9) 0.0175(9) 0.0199(9) -0.0003(7) 0.0000(7) -0.0033(7) C2 0.0211(9) 0.0176(8) 0.0205(9) 0.0020(7) 0.0035(7) 0.0027(7) C3 0.0242(9) 0.0173(8) 0.0202(9) 0.0034(7) 0.0058(7) 0.0006(7) C4 0.0219(9) 0.0280(10) 0.0315(11) -0.0002(8) 0.0035(8) 0.0068(8) C5 0.0326(11) 0.0264(11) 0.0236(10) 0.0016(8) -0.0008(8) 0.0033(8) C6 0.0231(9) 0.0160(8) 0.0190(9) -0.0015(7) -0.0029(7) -0.0032(7) C7 0.0203(9) 0.0215(9) 0.0216(9) -0.0040(7) -0.0016(7) -0.0009(7) C8 0.0270(10) 0.0199(10) 0.0340(11) -0.0034(8) 0.0019(8) 0.0001(8) C9 0.0288(11) 0.0230(11) 0.0434(13) -0.0120(9) -0.0014(9) 0.0031(8) C10 0.0191(9) 0.0387(12) 0.0333(11) -0.0174(9) 0.0007(8) 0.0014(8) C11 0.0226(10) 0.0362(12) 0.0289(11) -0.0022(9) 0.0019(8) -0.0053(8) C12 0.0234(9) 0.0231(9) 0.0266(10) 0.0000(8) 0.0005(7) -0.0013(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 P1 2.0469(5) . ? P1 O1 1.5693(13) . ? P1 O2 1.5747(13) . ? P1 O3 1.6352(13) . ? Cl1 C10 1.743(2) . ? O3 C6 1.382(2) . ? O4 C6 1.200(2) . ? O1 C1 1.473(2) . ? O2 C3 1.470(2) . ? C1 C2 1.524(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.522(3) . ? C2 C5 1.525(3) . ? C2 C4 1.532(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.478(3) . ? C7 C12 1.392(3) . ? C7 C8 1.393(3) . ? C8 C9 1.381(3) . ? C8 H8 0.9500 . ? C9 C10 1.386(3) . ? C9 H9 0.9500 . ? C10 C11 1.381(3) . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O2 106.16(7) . . ? O1 P1 O3 104.93(7) . . ? O2 P1 O3 99.12(7) . . ? O1 P1 Se1 115.20(5) . . ? O2 P1 Se1 114.03(5) . . ? O3 P1 Se1 115.69(5) . . ? C6 O3 P1 122.19(11) . . ? C1 O1 P1 118.18(10) . . ? C3 O2 P1 117.74(10) . . ? O1 C1 C2 111.15(14) . . ? O1 C1 H1A 109.4 . . ? C2 C1 H1A 109.4 . . ? O1 C1 H1B 109.4 . . ? C2 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? C3 C2 C1 108.58(15) . . ? C3 C2 C5 108.70(15) . . ? C1 C2 C5 108.38(15) . . ? C3 C2 C4 110.12(16) . . ? C1 C2 C4 110.62(15) . . ? C5 C2 C4 110.37(16) . . ? O2 C3 C2 110.95(14) . . ? O2 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? O2 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O4 C6 O3 122.07(17) . . ? O4 C6 C7 125.56(17) . . ? O3 C6 C7 112.36(15) . . ? C12 C7 C8 119.99(18) . . ? C12 C7 C6 122.72(17) . . ? C8 C7 C6 117.29(17) . . ? C9 C8 C7 120.51(19) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 118.8(2) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 121.57(19) . . ? C11 C10 Cl1 119.30(17) . . ? C9 C10 Cl1 119.13(17) . . ? C10 C11 C12 119.50(19) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C7 119.65(18) . . ? C11 C12 H12 120.2 . . ? C7 C12 H12 120.2 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 P1 O3 C6 62.67(14) . . . . ? O2 P1 O3 C6 172.21(13) . . . . ? Se1 P1 O3 C6 -65.46(13) . . . . ? O2 P1 O1 C1 -42.56(14) . . . . ? O3 P1 O1 C1 61.79(13) . . . . ? Se1 P1 O1 C1 -169.79(10) . . . . ? O1 P1 O2 C3 43.25(13) . . . . ? O3 P1 O2 C3 -65.31(12) . . . . ? Se1 P1 O2 C3 171.17(10) . . . . ? P1 O1 C1 C2 53.56(18) . . . . ? O1 C1 C2 C3 -58.92(18) . . . . ? O1 C1 C2 C5 -176.84(14) . . . . ? O1 C1 C2 C4 62.03(19) . . . . ? P1 O2 C3 C2 -54.98(17) . . . . ? C1 C2 C3 O2 59.72(19) . . . . ? C5 C2 C3 O2 177.43(14) . . . . ? C4 C2 C3 O2 -61.54(19) . . . . ? P1 O3 C6 O4 -5.3(2) . . . . ? P1 O3 C6 C7 174.56(12) . . . . ? O4 C6 C7 C12 172.24(18) . . . . ? O3 C6 C7 C12 -7.6(2) . . . . ? O4 C6 C7 C8 -7.9(3) . . . . ? O3 C6 C7 C8 172.27(15) . . . . ? C12 C7 C8 C9 0.0(3) . . . . ? C6 C7 C8 C9 -179.83(18) . . . . ? C7 C8 C9 C10 0.2(3) . . . . ? C8 C9 C10 C11 -0.6(3) . . . . ? C8 C9 C10 Cl1 178.71(15) . . . . ? C9 C10 C11 C12 0.8(3) . . . . ? Cl1 C10 C11 C12 -178.56(15) . . . . ? C10 C11 C12 C7 -0.5(3) . . . . ? C8 C7 C12 C11 0.1(3) . . . . ? C6 C7 C12 C11 179.97(18) . . . . ? _chemical_name_common ;O-(p-chlorobenzoyl)-2-oxo-2-seleno-5,5-dimethyl-1,3,2- dioxaphosphorinan ; data_6d _database_code_depnum_ccdc_archive 'CCDC 717029' _audit_creation_date 2008-11-28T07:49:15-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; O-(p-metoxybenzoyl)-2-oxo-2-seleno-5,5-dimethyl-1,3,2-dioxaphosphorinan ; _chemical_formula_moiety 'C13 H17 O5 P1 Se1' _chemical_formula_sum 'C13 H17 O5 P Se' _chemical_formula_weight 363.2 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6686(3) _cell_length_b 14.9809(4) _cell_length_c 12.4583(4) _cell_angle_alpha 90 _cell_angle_beta 107.683(4) _cell_angle_gamma 90 _cell_volume 1541.44(9) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5216 _cell_measurement_theta_min 2.1846 _cell_measurement_theta_max 32.4194 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.395 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.045 _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.554 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.375 _exptl_absorpt_correction_T_max 0.9 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 8.1883 _diffrn_orient_matrix_ub_11 0.0190508572 _diffrn_orient_matrix_ub_12 -0.0188487965 _diffrn_orient_matrix_ub_13 0.0546704589 _diffrn_orient_matrix_ub_21 -0.0811895515 _diffrn_orient_matrix_ub_22 -0.0146122846 _diffrn_orient_matrix_ub_23 -0.0115951816 _diffrn_orient_matrix_ub_31 0.0202068575 _diffrn_orient_matrix_ub_32 -0.0408708954 _diffrn_orient_matrix_ub_33 -0.0210474021 _diffrn_measurement_device '4-axis \k geometry diffractometer' _diffrn_measurement_device_type 'KM4CCD, Oxford Diffraction' _diffrn_measurement_method '\w scans, 0.75 deg width' _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_unetI/netI 0.0327 _diffrn_reflns_number 13199 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3718 _reflns_number_gt 2324 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0631P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3718 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.666 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.148 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.46692(5) 0.14617(2) 0.24287(3) 0.06978(16) Uani 1 1 d . . . P1 P 0.51839(8) 0.18049(4) 0.09801(6) 0.04378(18) Uani 1 1 d . . . O2 O 0.4798(2) 0.10473(11) 0.00774(15) 0.0437(4) Uani 1 1 d . . . O1 O 0.6984(2) 0.20889(12) 0.11585(15) 0.0504(5) Uani 1 1 d . . . O3 O 0.4269(2) 0.26938(11) 0.03429(15) 0.0479(4) Uani 1 1 d . . . O4 O 0.1782(2) 0.20820(13) -0.0203(2) 0.0660(6) Uani 1 1 d . . . O5 O 0.0252(3) 0.61607(13) -0.14765(19) 0.0641(6) Uani 1 1 d . . . C1 C 0.7622(3) 0.21075(19) 0.0191(2) 0.0495(7) Uani 1 1 d . . . H1A H 0.8779 0.2218 0.0455 0.059 Uiso 1 1 calc R . . H1B H 0.7116 0.2591 -0.0311 0.059 Uiso 1 1 calc R . . C2 C 0.7296(3) 0.12292(16) -0.0448(2) 0.0412(6) Uani 1 1 d . . . C3 C 0.5480(3) 0.10804(16) -0.0861(2) 0.0418(6) Uani 1 1 d . . . H3A H 0.4971 0.1560 -0.1368 0.050 Uiso 1 1 calc R . . H3B H 0.5249 0.0524 -0.1278 0.050 Uiso 1 1 calc R . . C4 C 0.8145(3) 0.04642(19) 0.0296(2) 0.0559(7) Uani 1 1 d . . . H4A H 0.9283 0.0589 0.0583 0.084 Uiso 1 1 calc R . . H4B H 0.7981 -0.0077 -0.0137 0.084 Uiso 1 1 calc R . . H4C H 0.7709 0.0397 0.0914 0.084 Uiso 1 1 calc R . . C5 C 0.7890(4) 0.1304(2) -0.1480(3) 0.0616(8) Uani 1 1 d . . . H5A H 0.7326 0.1781 -0.1953 0.092 Uiso 1 1 calc R . . H5B H 0.7687 0.0753 -0.1892 0.092 Uiso 1 1 calc R . . H5C H 0.9032 0.1426 -0.1242 0.092 Uiso 1 1 calc R . . C6 C 0.2601(3) 0.27316(18) -0.0140(2) 0.0470(6) Uani 1 1 d . . . C7 C 0.2031(3) 0.36336(17) -0.0527(2) 0.0429(6) Uani 1 1 d . . . C8 C 0.2986(3) 0.43847(18) -0.0244(2) 0.0519(7) Uani 1 1 d . . . H8 H 0.4070 0.4328 0.0175 0.062 Uiso 1 1 calc R . . C9 C 0.2352(4) 0.52137(19) -0.0574(3) 0.0595(8) Uani 1 1 d . . . H9 H 0.3005 0.5716 -0.0365 0.071 Uiso 1 1 calc R . . C10 C 0.0754(3) 0.53116(18) -0.1212(2) 0.0480(6) Uani 1 1 d . . . C11 C -0.0212(3) 0.45661(19) -0.1512(2) 0.0522(7) Uani 1 1 d . . . H11 H -0.1291 0.4624 -0.1943 0.063 Uiso 1 1 calc R . . C12 C 0.0428(4) 0.37365(18) -0.1171(2) 0.0516(7) Uani 1 1 d . . . H12 H -0.0228 0.3235 -0.1376 0.062 Uiso 1 1 calc R . . C13 C -0.1356(4) 0.6314(2) -0.2169(3) 0.0687(9) Uani 1 1 d . . . H13A H -0.1505 0.6054 -0.2897 0.103 Uiso 1 1 calc R . . H13B H -0.1552 0.6945 -0.2249 0.103 Uiso 1 1 calc R . . H13C H -0.2101 0.6048 -0.1829 0.103 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.0922(3) 0.0721(3) 0.0535(2) -0.00309(15) 0.03485(18) -0.00166(18) P1 0.0455(4) 0.0403(4) 0.0468(4) -0.0080(3) 0.0158(3) -0.0024(3) O2 0.0433(10) 0.0389(9) 0.0537(11) -0.0091(8) 0.0217(8) -0.0078(8) O1 0.0442(11) 0.0519(11) 0.0527(11) -0.0168(9) 0.0109(9) -0.0074(9) O3 0.0436(11) 0.0400(10) 0.0608(11) -0.0040(8) 0.0170(9) -0.0008(8) O4 0.0522(12) 0.0472(11) 0.0934(16) -0.0006(11) 0.0142(11) -0.0117(10) O5 0.0684(14) 0.0502(12) 0.0725(14) 0.0030(10) 0.0193(12) 0.0069(10) C1 0.0404(15) 0.0485(15) 0.0610(17) -0.0052(13) 0.0175(13) -0.0077(12) C2 0.0392(14) 0.0412(13) 0.0452(15) -0.0015(11) 0.0157(12) -0.0026(11) C3 0.0437(14) 0.0384(13) 0.0432(14) -0.0036(11) 0.0132(11) -0.0034(11) C4 0.0465(17) 0.0552(17) 0.0650(19) 0.0030(14) 0.0156(14) 0.0086(14) C5 0.0599(19) 0.071(2) 0.0635(19) -0.0034(15) 0.0325(16) -0.0114(15) C6 0.0473(17) 0.0479(16) 0.0481(15) -0.0065(12) 0.0180(13) -0.0046(13) C7 0.0438(15) 0.0464(15) 0.0419(14) -0.0044(11) 0.0181(12) -0.0030(12) C8 0.0359(15) 0.0495(16) 0.0696(19) -0.0035(13) 0.0152(13) -0.0017(12) C9 0.0473(18) 0.0423(15) 0.090(2) -0.0067(15) 0.0223(16) -0.0065(13) C10 0.0546(17) 0.0472(16) 0.0466(15) -0.0003(12) 0.0218(13) 0.0042(13) C11 0.0480(16) 0.0599(18) 0.0436(15) 0.0006(13) 0.0063(12) -0.0011(14) C12 0.0519(17) 0.0507(17) 0.0494(16) -0.0035(12) 0.0110(13) -0.0091(13) C13 0.077(2) 0.068(2) 0.059(2) 0.0080(15) 0.0163(17) 0.0226(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 P1 2.0517(7) . ? P1 O2 1.5608(18) . ? P1 O1 1.5671(19) . ? P1 O3 1.6280(19) . ? O2 C3 1.462(3) . ? O1 C1 1.471(3) . ? O3 C6 1.388(3) . ? O4 C6 1.194(3) . ? O5 C10 1.352(3) . ? O5 C13 1.418(4) . ? C1 C2 1.519(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C4 1.516(4) . ? C2 C3 1.517(3) . ? C2 C5 1.527(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.469(4) . ? C7 C8 1.378(4) . ? C7 C12 1.386(4) . ? C8 C9 1.370(4) . ? C8 H8 0.9300 . ? C9 C10 1.380(4) . ? C9 H9 0.9300 . ? C10 C11 1.378(4) . ? C11 C12 1.375(4) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 P1 O1 106.59(10) . . ? O2 P1 O3 106.11(10) . . ? O1 P1 O3 99.42(10) . . ? O2 P1 Se1 113.30(7) . . ? O1 P1 Se1 114.62(8) . . ? O3 P1 Se1 115.47(7) . . ? C3 O2 P1 120.09(14) . . ? C1 O1 P1 119.67(15) . . ? C6 O3 P1 122.26(16) . . ? C10 O5 C13 119.0(2) . . ? O1 C1 C2 110.9(2) . . ? O1 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 108.0 . . ? C4 C2 C3 110.9(2) . . ? C4 C2 C1 110.9(2) . . ? C3 C2 C1 108.3(2) . . ? C4 C2 C5 110.2(2) . . ? C3 C2 C5 107.8(2) . . ? C1 C2 C5 108.7(2) . . ? O2 C3 C2 111.3(2) . . ? O2 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? O2 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O4 C6 O3 121.1(2) . . ? O4 C6 C7 126.5(3) . . ? O3 C6 C7 112.5(2) . . ? C8 C7 C12 118.4(2) . . ? C8 C7 C6 123.4(2) . . ? C12 C7 C6 118.1(2) . . ? C9 C8 C7 120.5(3) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 120.7(3) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? O5 C10 C11 124.9(3) . . ? O5 C10 C9 115.7(3) . . ? C11 C10 C9 119.4(3) . . ? C12 C11 C10 119.6(3) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C7 121.3(3) . . ? C11 C12 H12 119.4 . . ? C7 C12 H12 119.4 . . ? O5 C13 H13A 109.5 . . ? O5 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O5 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 P1 O2 C3 -36.57(19) . . . . ? O3 P1 O2 C3 68.73(18) . . . . ? Se1 P1 O2 C3 -163.56(15) . . . . ? O2 P1 O1 C1 36.8(2) . . . . ? O3 P1 O1 C1 -73.23(19) . . . . ? Se1 P1 O1 C1 163.03(16) . . . . ? O2 P1 O3 C6 60.72(19) . . . . ? O1 P1 O3 C6 171.16(18) . . . . ? Se1 P1 O3 C6 -65.69(19) . . . . ? P1 O1 C1 C2 -51.6(3) . . . . ? O1 C1 C2 C4 -62.1(3) . . . . ? O1 C1 C2 C3 59.8(3) . . . . ? O1 C1 C2 C5 176.7(2) . . . . ? P1 O2 C3 C2 51.1(2) . . . . ? C4 C2 C3 O2 62.2(3) . . . . ? C1 C2 C3 O2 -59.6(3) . . . . ? C5 C2 C3 O2 -177.0(2) . . . . ? P1 O3 C6 O4 -7.4(3) . . . . ? P1 O3 C6 C7 172.13(16) . . . . ? O4 C6 C7 C8 167.3(3) . . . . ? O3 C6 C7 C8 -12.2(4) . . . . ? O4 C6 C7 C12 -9.8(4) . . . . ? O3 C6 C7 C12 170.7(2) . . . . ? C12 C7 C8 C9 1.3(4) . . . . ? C6 C7 C8 C9 -175.9(3) . . . . ? C7 C8 C9 C10 -1.1(4) . . . . ? C13 O5 C10 C11 -4.0(4) . . . . ? C13 O5 C10 C9 177.5(3) . . . . ? C8 C9 C10 O5 179.1(3) . . . . ? C8 C9 C10 C11 0.5(4) . . . . ? O5 C10 C11 C12 -178.4(3) . . . . ? C9 C10 C11 C12 0.0(4) . . . . ? C10 C11 C12 C7 0.1(4) . . . . ? C8 C7 C12 C11 -0.7(4) . . . . ? C6 C7 C12 C11 176.5(2) . . . . ? _chemical_name_common ;O-(p-metoxybenzoyl)-2-oxo-2-seleno-5,5-dimethyl-1,3,2- dioxaphosphorinan ; data_6e _database_code_depnum_ccdc_archive 'CCDC 717030' _audit_creation_date 2008-09-12T08:38:48-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; O-(p-nitrobenzoyl)-2-oxo-2-seleno-5,5-dimethyl-1,3,2-dioxaphosphorinan ; _chemical_formula_moiety 'C12 H14 N1 O6 P1 Se1' _chemical_formula_sum 'C12 H14 N O6 P Se' _chemical_formula_weight 378.17 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.4014(10) _cell_length_b 7.6161(3) _cell_length_c 12.2729(6) _cell_angle_alpha 90 _cell_angle_beta 103.358(6) _cell_angle_gamma 90 _cell_volume 1491.59(13) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5589 _cell_measurement_theta_min 2.3418 _cell_measurement_theta_max 32.4923 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.09 _exptl_crystal_density_diffrn 1.684 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.65 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.458 _exptl_absorpt_correction_T_max 0.786 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 8.1883 _diffrn_orient_matrix_ub_11 -0.0492747384 _diffrn_orient_matrix_ub_12 0.0514676856 _diffrn_orient_matrix_ub_13 -0.0119757795 _diffrn_orient_matrix_ub_21 0.0234072126 _diffrn_orient_matrix_ub_22 0.0639865559 _diffrn_orient_matrix_ub_23 0.0302946459 _diffrn_orient_matrix_ub_31 0.0235812212 _diffrn_orient_matrix_ub_32 0.0439680113 _diffrn_orient_matrix_ub_33 -0.030149557 _diffrn_measurement_device '4-axis \k geometry diffractometer' _diffrn_measurement_device_type 'KM4CCD, Oxford Diffraction' _diffrn_measurement_method '\w scans, 0.75 deg width' _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_unetI/netI 0.048 _diffrn_reflns_number 11320 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 27 _diffrn_reflns_theta_full 27 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 3245 _reflns_number_gt 2395 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0937P)^2^+0.2743P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3245 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1524 _refine_ls_wR_factor_gt 0.1438 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.269 _refine_diff_density_min -1.555 _refine_diff_density_rms 0.163 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.31710(3) 0.72120(6) 0.68414(4) 0.03223(19) Uani 1 1 d . . . P1 P 0.30600(7) 0.91750(13) 0.79328(9) 0.0209(3) Uani 1 1 d . . . O1 O 0.37538(18) 0.9228(4) 0.9043(2) 0.0249(7) Uani 1 1 d . . . O2 O 0.30130(18) 1.1068(3) 0.7423(2) 0.0222(6) Uani 1 1 d . . . O3 O 0.22296(18) 0.9020(4) 0.8472(2) 0.0223(6) Uani 1 1 d . . . O4 O 0.13193(19) 0.9790(4) 0.6864(2) 0.0264(7) Uani 1 1 d . . . O5 O -0.1154(2) 0.6668(5) 1.0614(3) 0.0382(8) Uani 1 1 d . . . O6 O -0.19414(19) 0.8382(4) 0.9416(3) 0.0305(7) Uani 1 1 d . . . N1 N -0.1267(2) 0.7678(4) 0.9815(3) 0.0240(8) Uani 1 1 d . . . C1 C 0.3801(3) 1.0768(5) 0.9783(3) 0.0252(9) Uani 1 1 d . . . H1A H 0.4316 1.0690 1.0391 0.030 Uiso 1 1 calc R . . H1B H 0.3313 1.0765 1.0130 0.030 Uiso 1 1 calc R . . C2 C 0.3812(3) 1.2479(5) 0.9141(4) 0.0237(9) Uani 1 1 d . . . C3 C 0.3035(3) 1.2557(5) 0.8191(3) 0.0222(9) Uani 1 1 d . . . H3A H 0.2529 1.2534 0.8501 0.027 Uiso 1 1 calc R . . H3B H 0.3032 1.3671 0.7774 0.027 Uiso 1 1 calc R . . C4 C 0.4602(3) 1.2612(6) 0.8669(4) 0.0301(10) Uani 1 1 d . . . H4A H 0.5100 1.2644 0.9288 0.045 Uiso 1 1 calc R . . H4B H 0.4576 1.3686 0.8223 0.045 Uiso 1 1 calc R . . H4C H 0.4632 1.1590 0.8195 0.045 Uiso 1 1 calc R . . C5 C 0.3772(3) 1.4000(6) 0.9954(4) 0.0343(11) Uani 1 1 d . . . H5A H 0.4272 1.3976 1.0571 0.051 Uiso 1 1 calc R . . H5B H 0.3270 1.3872 1.0253 0.051 Uiso 1 1 calc R . . H5C H 0.3747 1.5120 0.9554 0.051 Uiso 1 1 calc R . . C6 C 0.1446(3) 0.9279(5) 0.7805(4) 0.0221(9) Uani 1 1 d . . . C7 C 0.0766(3) 0.8869(5) 0.8398(3) 0.0217(8) Uani 1 1 d . . . C8 C 0.0900(3) 0.7863(5) 0.9369(3) 0.0217(9) Uani 1 1 d . . . H8 H 0.1448 0.7468 0.9718 0.026 Uiso 1 1 calc R . . C9 C 0.0230(3) 0.7450(5) 0.9817(3) 0.0219(9) Uani 1 1 d . . . H9 H 0.0307 0.6737 1.0468 0.026 Uiso 1 1 calc R . . C10 C -0.0554(3) 0.8074(5) 0.9316(3) 0.0214(9) Uani 1 1 d . . . C11 C -0.0707(3) 0.9088(5) 0.8359(3) 0.0234(9) Uani 1 1 d . . . H11 H -0.1254 0.9505 0.8030 0.028 Uiso 1 1 calc R . . C12 C -0.0029(3) 0.9479(5) 0.7892(4) 0.0240(9) Uani 1 1 d . . . H12 H -0.0112 1.0162 0.7228 0.029 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.0502(3) 0.0153(3) 0.0344(3) -0.00496(18) 0.0164(2) -0.00008(19) P1 0.0291(6) 0.0115(5) 0.0220(5) 0.0015(4) 0.0058(4) -0.0001(4) O1 0.0294(16) 0.0160(14) 0.0284(16) 0.0049(12) 0.0045(13) 0.0005(12) O2 0.0314(16) 0.0125(13) 0.0218(14) 0.0022(11) 0.0042(12) -0.0011(11) O3 0.0258(15) 0.0163(14) 0.0236(14) 0.0008(12) 0.0031(12) -0.0026(12) O4 0.0352(17) 0.0217(15) 0.0206(15) 0.0067(13) 0.0030(12) -0.0014(13) O5 0.041(2) 0.045(2) 0.0291(18) 0.0114(16) 0.0098(15) -0.0012(16) O6 0.0304(18) 0.0273(17) 0.0345(18) 0.0002(14) 0.0086(14) 0.0011(14) N1 0.030(2) 0.0196(17) 0.0228(18) -0.0058(15) 0.0059(15) -0.0033(15) C1 0.031(2) 0.022(2) 0.021(2) 0.0023(17) 0.0013(17) -0.0017(18) C2 0.033(2) 0.018(2) 0.020(2) -0.0009(16) 0.0058(17) -0.0057(17) C3 0.034(2) 0.0108(18) 0.022(2) 0.0000(16) 0.0070(18) -0.0023(16) C4 0.030(2) 0.025(2) 0.035(3) 0.0001(19) 0.008(2) -0.0075(18) C5 0.048(3) 0.024(2) 0.030(2) -0.009(2) 0.008(2) -0.009(2) C6 0.025(2) 0.0097(18) 0.029(2) -0.0016(16) 0.0024(17) -0.0029(16) C7 0.028(2) 0.0095(17) 0.025(2) -0.0015(16) 0.0009(17) -0.0040(16) C8 0.029(2) 0.0135(18) 0.020(2) -0.0015(16) 0.0000(17) -0.0013(17) C9 0.032(2) 0.014(2) 0.0173(19) 0.0016(15) 0.0009(16) -0.0027(16) C10 0.029(2) 0.016(2) 0.020(2) -0.0038(15) 0.0074(17) -0.0040(16) C11 0.029(2) 0.0171(19) 0.022(2) -0.0030(16) 0.0019(17) 0.0018(17) C12 0.033(2) 0.014(2) 0.023(2) 0.0024(16) 0.0023(18) -0.0017(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 P1 2.0433(11) . ? P1 O1 1.561(3) . ? P1 O2 1.566(3) . ? P1 O3 1.650(3) . ? O1 C1 1.475(5) . ? O2 C3 1.469(5) . ? O3 C6 1.369(5) . ? O4 C6 1.190(5) . ? O5 N1 1.226(5) . ? O6 N1 1.224(5) . ? N1 C10 1.472(5) . ? C1 C2 1.525(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.517(6) . ? C2 C4 1.540(6) . ? C2 C5 1.540(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.500(6) . ? C7 C12 1.389(6) . ? C7 C8 1.391(6) . ? C8 C9 1.375(6) . ? C8 H8 0.9500 . ? C9 C10 1.374(6) . ? C9 H9 0.9500 . ? C10 C11 1.379(6) . ? C11 C12 1.395(6) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O2 106.46(16) . . ? O1 P1 O3 98.92(15) . . ? O2 P1 O3 104.88(15) . . ? O1 P1 Se1 115.70(12) . . ? O2 P1 Se1 114.55(12) . . ? O3 P1 Se1 114.65(11) . . ? C1 O1 P1 118.8(2) . . ? C3 O2 P1 117.6(2) . . ? C6 O3 P1 119.8(3) . . ? O6 N1 O5 123.4(4) . . ? O6 N1 C10 118.4(3) . . ? O5 N1 C10 118.2(4) . . ? O1 C1 C2 111.5(3) . . ? O1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? O1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? C3 C2 C1 108.8(3) . . ? C3 C2 C4 109.8(4) . . ? C1 C2 C4 111.2(4) . . ? C3 C2 C5 108.3(4) . . ? C1 C2 C5 107.5(3) . . ? C4 C2 C5 111.1(4) . . ? O2 C3 C2 110.8(3) . . ? O2 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? O2 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O4 C6 O3 123.9(4) . . ? O4 C6 C7 123.8(4) . . ? O3 C6 C7 112.4(4) . . ? C12 C7 C8 121.0(4) . . ? C12 C7 C6 116.1(4) . . ? C8 C7 C6 122.8(4) . . ? C9 C8 C7 119.0(4) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C10 C9 C8 119.6(4) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 122.8(4) . . ? C9 C10 N1 119.6(4) . . ? C11 C10 N1 117.6(4) . . ? C10 C11 C12 117.6(4) . . ? C10 C11 H11 121.2 . . ? C12 C11 H11 121.2 . . ? C7 C12 C11 120.0(4) . . ? C7 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 O1 C1 41.2(3) . . . . ? O3 P1 O1 C1 -67.3(3) . . . . ? Se1 P1 O1 C1 169.7(2) . . . . ? O1 P1 O2 C3 -43.6(3) . . . . ? O3 P1 O2 C3 60.6(3) . . . . ? Se1 P1 O2 C3 -172.8(2) . . . . ? O1 P1 O3 C6 167.1(3) . . . . ? O2 P1 O3 C6 57.4(3) . . . . ? Se1 P1 O3 C6 -69.2(3) . . . . ? P1 O1 C1 C2 -51.0(4) . . . . ? O1 C1 C2 C3 57.2(4) . . . . ? O1 C1 C2 C4 -63.8(5) . . . . ? O1 C1 C2 C5 174.4(3) . . . . ? P1 O2 C3 C2 56.1(4) . . . . ? C1 C2 C3 O2 -59.8(4) . . . . ? C4 C2 C3 O2 62.1(4) . . . . ? C5 C2 C3 O2 -176.5(3) . . . . ? P1 O3 C6 O4 -7.8(5) . . . . ? P1 O3 C6 C7 172.9(3) . . . . ? O4 C6 C7 C12 -14.0(6) . . . . ? O3 C6 C7 C12 165.3(3) . . . . ? O4 C6 C7 C8 162.8(4) . . . . ? O3 C6 C7 C8 -17.9(5) . . . . ? C12 C7 C8 C9 1.1(6) . . . . ? C6 C7 C8 C9 -175.6(4) . . . . ? C7 C8 C9 C10 -1.7(6) . . . . ? C8 C9 C10 C11 1.1(6) . . . . ? C8 C9 C10 N1 -178.1(3) . . . . ? O6 N1 C10 C9 173.2(4) . . . . ? O5 N1 C10 C9 -6.2(6) . . . . ? O6 N1 C10 C11 -6.0(5) . . . . ? O5 N1 C10 C11 174.5(4) . . . . ? C9 C10 C11 C12 0.1(6) . . . . ? N1 C10 C11 C12 179.4(3) . . . . ? C8 C7 C12 C11 0.1(6) . . . . ? C6 C7 C12 C11 177.1(4) . . . . ? C10 C11 C12 C7 -0.8(6) . . . . ? _chemical_name_common ;O-(p-nitrobenzoyl)-2-oxo-2-seleno-5,5-dimethyl-1,3,2- dioxaphosphorinan ; data_8a _database_code_depnum_ccdc_archive 'CCDC 717031' _audit_creation_date 2008-11-03T09:02:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; N-(p-chlorobenzoyl)-2-amino-2-seleno-5,5-dimethyl-1,3,2-dioxaphosphorinan ; _chemical_formula_moiety 'C12 H15 Cl1 N1 O3 P1 Se1' _chemical_formula_sum 'C12 H15 Cl N O3 P Se' _chemical_formula_weight 366.63 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.9308(7) _cell_length_b 15.4868(9) _cell_length_c 8.2832(4) _cell_angle_alpha 90 _cell_angle_beta 91.617(5) _cell_angle_gamma 90 _cell_volume 1529.88(15) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3634 _cell_measurement_theta_min 2.1576 _cell_measurement_theta_max 32.4404 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.736 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.585 _exptl_absorpt_correction_T_max 0.870 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 8.1883 _diffrn_orient_matrix_ub_11 0.0053035889 _diffrn_orient_matrix_ub_12 -0.0240877486 _diffrn_orient_matrix_ub_13 -0.0505438802 _diffrn_orient_matrix_ub_21 0.0501359186 _diffrn_orient_matrix_ub_22 0.0325130951 _diffrn_orient_matrix_ub_23 -0.0225565473 _diffrn_orient_matrix_ub_31 0.0693517476 _diffrn_orient_matrix_ub_32 -0.0217984865 _diffrn_orient_matrix_ub_33 0.0222126975 _diffrn_measurement_device '4-axis \k geometry diffractometer' _diffrn_measurement_device_type 'KM4CCD, Oxford Diffraction' _diffrn_measurement_method '\w scans, 0.75 deg width' _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_unetI/netI 0.0639 _diffrn_reflns_number 13245 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 3689 _reflns_number_gt 1894 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0701P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3689 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0926 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 0.817 _refine_ls_restrained_S_all 0.817 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.774 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.087 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.90845(4) 0.06075(3) 0.15091(5) 0.07363(19) Uani 1 1 d . . . P1 P 0.88742(7) 0.10240(6) 0.38291(11) 0.0471(2) Uani 1 1 d . . . Cl1 Cl 1.49595(9) 0.33484(8) 0.68580(16) 0.0936(4) Uani 1 1 d . . . O1 O 0.78461(18) 0.16435(13) 0.4000(3) 0.0509(6) Uani 1 1 d . . . O2 O 0.86855(18) 0.02581(13) 0.5065(3) 0.0518(6) Uani 1 1 d . . . O3 O 0.9962(2) 0.27270(15) 0.3211(3) 0.0639(7) Uani 1 1 d . . . N1 N 0.9980(3) 0.1517(2) 0.4710(4) 0.0512(8) Uani 1 1 d . . . C1 C 0.7453(3) 0.1827(2) 0.5622(4) 0.0547(9) Uani 1 1 d . . . H1A H 0.6784 0.2183 0.5543 0.066 Uiso 1 1 calc R . . H1B H 0.8025 0.2147 0.6225 0.066 Uiso 1 1 calc R . . C2 C 0.7191(3) 0.0993(2) 0.6514(4) 0.0493(8) Uani 1 1 d . . . C3 C 0.8248(3) 0.0462(2) 0.6653(4) 0.0534(9) Uani 1 1 d . . . H3A H 0.8812 0.0779 0.7279 0.064 Uiso 1 1 calc R . . H3B H 0.8094 -0.007 0.7223 0.064 Uiso 1 1 calc R . . C4 C 0.6251(3) 0.0494(3) 0.5634(5) 0.0686(11) Uani 1 1 d . . . H4A H 0.646 0.0383 0.4543 0.103 Uiso 1 1 calc R . . H4B H 0.5575 0.0829 0.5629 0.103 Uiso 1 1 calc R . . H4C H 0.613 -0.0044 0.6178 0.103 Uiso 1 1 calc R . . C5 C 0.6824(4) 0.1241(3) 0.8217(5) 0.0728(11) Uani 1 1 d . . . H5A H 0.6667 0.0727 0.8817 0.109 Uiso 1 1 calc R . . H5B H 0.6161 0.1592 0.8137 0.109 Uiso 1 1 calc R . . H5C H 0.7414 0.1558 0.876 0.109 Uiso 1 1 calc R . . C6 C 1.0441(3) 0.2279(2) 0.4201(4) 0.0484(8) Uani 1 1 d . . . C7 C 1.1571(3) 0.2513(2) 0.4912(4) 0.0464(8) Uani 1 1 d . . . C8 C 1.1906(3) 0.3361(2) 0.4823(5) 0.0641(10) Uani 1 1 d . . . H8 H 1.1424 0.3768 0.4357 0.077 Uiso 1 1 calc R . . C9 C 1.2943(3) 0.3614(3) 0.5414(5) 0.0728(11) Uani 1 1 d . . . H9 H 1.3161 0.4189 0.5346 0.087 Uiso 1 1 calc R . . C10 C 1.3649(3) 0.3019(3) 0.6099(5) 0.0617(10) Uani 1 1 d . . . C11 C 1.3337(3) 0.2173(3) 0.6193(5) 0.0678(11) Uani 1 1 d . . . H11 H 1.3826 0.1768 0.6651 0.081 Uiso 1 1 calc R . . C12 C 1.2296(3) 0.1921(2) 0.5608(5) 0.0607(10) Uani 1 1 d . . . H12 H 1.2081 0.1346 0.5684 0.073 Uiso 1 1 calc R . . H1 H 1.036(3) 0.124(2) 0.524(4) 0.044(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.0799(3) 0.0812(3) 0.0595(3) -0.0180(2) -0.0045(2) 0.0063(2) P1 0.0460(5) 0.0422(5) 0.0527(5) 0.0002(4) -0.0067(4) 0.0043(4) Cl1 0.0537(6) 0.1104(9) 0.1166(9) -0.0319(8) -0.0011(6) -0.0133(6) O1 0.0544(14) 0.0480(13) 0.0500(13) 0.0055(10) -0.0046(11) 0.0090(11) O2 0.0503(14) 0.0388(12) 0.0662(16) 0.0041(11) -0.0023(11) 0.0057(11) O3 0.0686(17) 0.0524(14) 0.0699(16) 0.0140(13) -0.0144(13) 0.0018(13) N1 0.0456(17) 0.0521(19) 0.0553(18) 0.0098(15) -0.0101(14) 0.0012(15) C1 0.062(2) 0.0458(19) 0.056(2) 0.0013(16) 0.0005(17) 0.0103(17) C2 0.049(2) 0.0458(19) 0.053(2) 0.0018(16) -0.0047(16) -0.0002(16) C3 0.054(2) 0.049(2) 0.057(2) 0.0080(16) -0.0050(17) -0.0011(17) C4 0.048(2) 0.073(3) 0.084(3) -0.002(2) -0.005(2) -0.0070(19) C5 0.087(3) 0.065(3) 0.067(2) 0.007(2) 0.008(2) 0.007(2) C6 0.057(2) 0.0412(19) 0.0472(19) -0.0026(16) 0.0046(17) 0.0053(17) C7 0.0476(19) 0.0424(19) 0.0494(19) -0.0033(14) 0.0052(15) 0.0003(16) C8 0.061(2) 0.047(2) 0.084(3) 0.0007(19) -0.007(2) -0.0008(19) C9 0.070(3) 0.050(2) 0.099(3) -0.016(2) 0.011(2) -0.013(2) C10 0.046(2) 0.071(3) 0.068(2) -0.020(2) 0.0079(18) -0.004(2) C11 0.049(2) 0.066(3) 0.089(3) 0.004(2) -0.001(2) 0.0043(19) C12 0.050(2) 0.047(2) 0.086(3) 0.0050(19) -0.0011(19) -0.0036(17) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 P1 2.0492(10) . ? P1 O1 1.567(2) . ? P1 O2 1.587(2) . ? P1 N1 1.674(3) . ? Cl1 C10 1.745(4) . ? O1 C1 1.463(4) . ? O2 C3 1.463(4) . ? O3 C6 1.207(4) . ? N1 C6 1.373(4) . ? N1 H1 0.75(3) . ? C1 C2 1.526(5) . ? C1 H1A 0.97 . ? C1 H1B 0.97 . ? C2 C3 1.508(5) . ? C2 C4 1.529(5) . ? C2 C5 1.537(5) . ? C3 H3A 0.97 . ? C3 H3B 0.97 . ? C4 H4A 0.96 . ? C4 H4B 0.96 . ? C4 H4C 0.96 . ? C5 H5A 0.96 . ? C5 H5B 0.96 . ? C5 H5C 0.96 . ? C6 C7 1.500(5) . ? C7 C12 1.376(5) . ? C7 C8 1.376(5) . ? C8 C9 1.375(5) . ? C8 H8 0.93 . ? C9 C10 1.362(6) . ? C9 H9 0.93 . ? C10 C11 1.364(5) . ? C11 C12 1.377(5) . ? C11 H11 0.93 . ? C12 H12 0.93 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O2 105.89(12) . . ? O1 P1 N1 106.92(14) . . ? O2 P1 N1 100.60(14) . . ? O1 P1 Se1 113.21(9) . . ? O2 P1 Se1 113.15(9) . . ? N1 P1 Se1 115.88(11) . . ? C1 O1 P1 118.28(19) . . ? C3 O2 P1 118.63(19) . . ? C6 N1 P1 125.1(3) . . ? C6 N1 H1 116(3) . . ? P1 N1 H1 116(3) . . ? O1 C1 C2 110.8(3) . . ? O1 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? C3 C2 C1 108.4(3) . . ? C3 C2 C4 111.2(3) . . ? C1 C2 C4 110.8(3) . . ? C3 C2 C5 109.0(3) . . ? C1 C2 C5 107.5(3) . . ? C4 C2 C5 109.9(3) . . ? O2 C3 C2 111.6(3) . . ? O2 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? O2 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 108 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O3 C6 N1 121.1(3) . . ? O3 C6 C7 122.1(3) . . ? N1 C6 C7 116.8(3) . . ? C12 C7 C8 118.5(3) . . ? C12 C7 C6 123.5(3) . . ? C8 C7 C6 118.0(3) . . ? C9 C8 C7 120.9(3) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C10 C9 C8 119.7(4) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 120.5(4) . . ? C9 C10 Cl1 119.3(3) . . ? C11 C10 Cl1 120.2(3) . . ? C10 C11 C12 119.8(4) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C7 C12 C11 120.6(3) . . ? C7 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 O1 C1 41.8(2) . . . . ? N1 P1 O1 C1 -64.9(3) . . . . ? Se1 P1 O1 C1 166.32(19) . . . . ? O1 P1 O2 C3 -40.2(2) . . . . ? N1 P1 O2 C3 70.9(2) . . . . ? Se1 P1 O2 C3 -164.82(18) . . . . ? O1 P1 N1 C6 -63.9(3) . . . . ? O2 P1 N1 C6 -174.3(3) . . . . ? Se1 P1 N1 C6 63.4(3) . . . . ? P1 O1 C1 C2 -55.1(3) . . . . ? O1 C1 C2 C3 60.4(4) . . . . ? O1 C1 C2 C4 -61.8(4) . . . . ? O1 C1 C2 C5 178.1(3) . . . . ? P1 O2 C3 C2 52.3(3) . . . . ? C1 C2 C3 O2 -59.2(3) . . . . ? C4 C2 C3 O2 62.8(4) . . . . ? C5 C2 C3 O2 -175.9(3) . . . . ? P1 N1 C6 O3 12.2(5) . . . . ? P1 N1 C6 C7 -166.7(2) . . . . ? O3 C6 C7 C12 -158.1(3) . . . . ? N1 C6 C7 C12 20.8(5) . . . . ? O3 C6 C7 C8 20.2(5) . . . . ? N1 C6 C7 C8 -160.9(3) . . . . ? C12 C7 C8 C9 0.1(6) . . . . ? C6 C7 C8 C9 -178.3(3) . . . . ? C7 C8 C9 C10 -0.1(6) . . . . ? C8 C9 C10 C11 0.4(6) . . . . ? C8 C9 C10 Cl1 -179.6(3) . . . . ? C9 C10 C11 C12 -0.8(6) . . . . ? Cl1 C10 C11 C12 179.2(3) . . . . ? C8 C7 C12 C11 -0.4(6) . . . . ? C6 C7 C12 C11 177.9(3) . . . . ? C10 C11 C12 C7 0.8(6) . . . . ? _chemical_name_common ;N-(p-chlorobenzoyl)-2-amino-2-seleno-5,5-dimethyl-1,3,2- dioxaphosphorinan ; data_8b _database_code_depnum_ccdc_archive 'CCDC 717032' _audit_creation_date 2008-09-18T10:12:07-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; N-pivaloyl-2-amino-2-seleno-5,5-dimethyl-1,3,2-dioxaphosphorinan ; _chemical_formula_moiety 'C10 H20 N1 O3 P1 Se1' _chemical_formula_sum 'C10 H20 N O3 P Se' _chemical_formula_weight 312.2 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.9981(2) _cell_length_b 27.8966(5) _cell_length_c 10.6258(3) _cell_angle_alpha 90 _cell_angle_beta 109.816(3) _cell_angle_gamma 90 _cell_volume 2788.18(11) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 11947 _cell_measurement_theta_min 2.1849 _cell_measurement_theta_max 32.3789 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.802 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.375 _exptl_absorpt_correction_T_max 0.75 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 8.1883 _diffrn_orient_matrix_ub_11 0.0723178202 _diffrn_orient_matrix_ub_12 0.004691224 _diffrn_orient_matrix_ub_13 0.0085105699 _diffrn_orient_matrix_ub_21 -0.0206940681 _diffrn_orient_matrix_ub_22 0.0098513945 _diffrn_orient_matrix_ub_23 -0.0653698712 _diffrn_orient_matrix_ub_31 -0.0058595804 _diffrn_orient_matrix_ub_32 0.0229570559 _diffrn_orient_matrix_ub_33 0.0263865124 _diffrn_measurement_device '4-axis \k geometry diffractometer' _diffrn_measurement_device_type 'KM4CCD, Oxford Diffraction' _diffrn_measurement_method '\w scans, 0.75 deg width' _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_unetI/netI 0.027 _diffrn_reflns_number 20709 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 27 _diffrn_reflns_theta_full 27 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 6084 _reflns_number_gt 4892 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0642P)^2^+0.0843P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 6084 _refine_ls_number_parameters 307 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0982 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 1.36 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.122 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' Se Se -0.0929 2.2259 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.48045(3) 0.081584(9) 0.64166(3) 0.02930(10) Uani 1 1 d . . . P1 P 0.44577(7) 0.15469(2) 0.62876(6) 0.01811(14) Uani 1 1 d . . . O1 O 0.39226(18) 0.17682(6) 0.74108(17) 0.0203(4) Uani 1 1 d . . . O2 O 0.58197(17) 0.18606(6) 0.63956(16) 0.0185(4) Uani 1 1 d . . . N1 N 0.3231(2) 0.17185(8) 0.4881(2) 0.0204(5) Uani 1 1 d . . . O3 O 0.32995(19) 0.25183(6) 0.52769(18) 0.0225(4) Uani 1 1 d . . . C1 C 0.5003(3) 0.18014(10) 0.8742(2) 0.0227(6) Uani 1 1 d . . . H1A H 0.5346 0.1476 0.9064 0.027 Uiso 1 1 calc R . . H1B H 0.4574 0.1942 0.9372 0.027 Uiso 1 1 calc R . . C2 C 0.6256(3) 0.21090(9) 0.8726(2) 0.0210(5) Uani 1 1 d . . . C3 C 0.6882(3) 0.18930(9) 0.7727(3) 0.0221(5) Uani 1 1 d . . . H3A H 0.7685 0.2094 0.7692 0.026 Uiso 1 1 calc R . . H3B H 0.7256 0.1569 0.8032 0.026 Uiso 1 1 calc R . . C4 C 0.5795(3) 0.26294(9) 0.8351(3) 0.0246(6) Uani 1 1 d . . . H4A H 0.5401 0.2763 0.9004 0.037 Uiso 1 1 calc R . . H4B H 0.507 0.2638 0.7458 0.037 Uiso 1 1 calc R . . H4C H 0.662 0.282 0.8353 0.037 Uiso 1 1 calc R . . C5 C 0.7376(3) 0.20890(11) 1.0129(3) 0.0324(7) Uani 1 1 d . . . H5A H 0.6958 0.2203 1.0786 0.049 Uiso 1 1 calc R . . H5B H 0.8184 0.2293 1.016 0.049 Uiso 1 1 calc R . . H5C H 0.7704 0.1758 1.0339 0.049 Uiso 1 1 calc R . . C6 C 0.2693(3) 0.21828(9) 0.4592(2) 0.0194(5) Uani 1 1 d . . . C7 C 0.1310(3) 0.22356(9) 0.3409(3) 0.0215(5) Uani 1 1 d . . . C8 C 0.1505(3) 0.20586(12) 0.2129(3) 0.0335(7) Uani 1 1 d . . . H8A H 0.231 0.2226 0.1997 0.05 Uiso 1 1 calc R . . H8B H 0.0639 0.2123 0.1368 0.05 Uiso 1 1 calc R . . H8C H 0.1691 0.1713 0.2196 0.05 Uiso 1 1 calc R . . C9 C 0.0147(3) 0.19420(11) 0.3710(3) 0.0302(6) Uani 1 1 d . . . H9A H 0.0384 0.16 0.3744 0.045 Uiso 1 1 calc R . . H9B H -0.077 0.1997 0.3005 0.045 Uiso 1 1 calc R . . H9C H 0.0087 0.2042 0.4574 0.045 Uiso 1 1 calc R . . C10 C 0.0900(3) 0.27686(10) 0.3252(3) 0.0313(6) Uani 1 1 d . . . H10A H 0.0767 0.2884 0.4073 0.047 Uiso 1 1 calc R . . H10B H 0.0013 0.2809 0.2497 0.047 Uiso 1 1 calc R . . H10C H 0.1658 0.2953 0.3086 0.047 Uiso 1 1 calc R . . H1 H 0.291(3) 0.1518(11) 0.440(3) 0.029(9) Uiso 1 1 d . . . Se2 Se -0.14187(3) 0.065549(11) 0.10808(3) 0.03110(10) Uani 1 1 d . . . P2 P 0.02034(7) 0.01796(2) 0.19895(7) 0.02067(15) Uani 1 1 d . . . O11 O 0.0531(2) 0.01431(6) 0.35440(17) 0.0233(4) Uani 1 1 d . . . O12 O -0.01633(19) -0.03447(6) 0.14261(17) 0.0220(4) Uani 1 1 d . . . N2 N 0.1777(2) 0.02618(8) 0.1759(2) 0.0219(5) Uani 1 1 d . A . O13 O 0.2319(2) 0.09356(7) 0.2974(2) 0.0318(5) Uani 1 1 d . A . C11 C 0.1344(3) -0.02708(10) 0.4268(3) 0.0243(6) Uani 1 1 d . . . H11A H 0.1381 -0.0261 0.521 0.029 Uiso 1 1 calc R . . H11B H 0.233 -0.0253 0.4262 0.029 Uiso 1 1 calc R . . C12 C 0.0671(3) -0.07404(9) 0.3632(3) 0.0226(6) Uani 1 1 d . . . C13 C 0.0653(3) -0.07489(9) 0.2189(3) 0.0233(6) Uani 1 1 d . . . H13A H 0.1641 -0.0733 0.2184 0.028 Uiso 1 1 calc R . . H13B H 0.0227 -0.1053 0.1759 0.028 Uiso 1 1 calc R . . C14 C -0.0848(3) -0.07922(10) 0.3662(3) 0.0265(6) Uani 1 1 d . . . H14A H -0.1434 -0.0526 0.3168 0.04 Uiso 1 1 calc R . . H14B H -0.0825 -0.0787 0.4591 0.04 Uiso 1 1 calc R . . H14C H -0.1255 -0.1097 0.3245 0.04 Uiso 1 1 calc R . . C15 C 0.1618(3) -0.11474(10) 0.4401(3) 0.0315(7) Uani 1 1 d . . . H15A H 0.1696 -0.1131 0.5345 0.047 Uiso 1 1 calc R . . H15B H 0.2565 -0.1117 0.4327 0.047 Uiso 1 1 calc R . . H15C H 0.12 -0.1456 0.4025 0.047 Uiso 1 1 calc R . . C16 C 0.2617(3) 0.06618(9) 0.2216(3) 0.0233(6) Uani 1 1 d . . . C17 C 0.3850(6) 0.07408(17) 0.1708(5) 0.0233(16) Uiso 0.778(6) 1 d PD A 1 C18 C 0.4860(5) 0.03114(16) 0.2173(5) 0.0465(13) Uiso 0.778(6) 1 d PD A 1 H18A H 0.5159 0.0284 0.3149 0.07 Uiso 0.778(6) 1 calc PR A 1 H18B H 0.5697 0.0359 0.1905 0.07 Uiso 0.778(6) 1 calc PR A 1 H18C H 0.4368 0.0017 0.1761 0.07 Uiso 0.778(6) 1 calc PR A 1 C19 C 0.4707(5) 0.11804(15) 0.2404(5) 0.0376(11) Uiso 0.778(6) 1 d PD A 1 H19A H 0.5569 0.1207 0.2165 0.056 Uiso 0.778(6) 1 calc PR A 1 H19B H 0.4972 0.1145 0.3375 0.056 Uiso 0.778(6) 1 calc PR A 1 H19C H 0.4128 0.147 0.2115 0.056 Uiso 0.778(6) 1 calc PR A 1 C20 C 0.3357(5) 0.07841(17) 0.0215(5) 0.0480(13) Uiso 0.778(6) 1 d PD A 1 H20A H 0.4184 0.0805 -0.008 0.072 Uiso 0.778(6) 1 calc PR A 1 H20B H 0.2776 0.1073 -0.0062 0.072 Uiso 0.778(6) 1 calc PR A 1 H20C H 0.279 0.0502 -0.0189 0.072 Uiso 0.778(6) 1 calc PR A 1 C17A C 0.4027(19) 0.0693(5) 0.1874(16) 0.021(6) Uiso 0.222(6) 1 d PD A 2 C18A C 0.422(2) 0.0288(6) 0.0997(19) 0.061(6) Uiso 0.222(6) 1 d PD A 2 H18D H 0.5231 0.0258 0.1103 0.092 Uiso 0.222(6) 1 calc PR A 2 H18E H 0.3674 0.0357 0.0059 0.092 Uiso 0.222(6) 1 calc PR A 2 H18F H 0.3887 -0.0013 0.1262 0.092 Uiso 0.222(6) 1 calc PR A 2 C19A C 0.436(2) 0.1230(5) 0.181(2) 0.051(5) Uiso 0.222(6) 1 d PD A 2 H19D H 0.5272 0.1268 0.1673 0.077 Uiso 0.222(6) 1 calc PR A 2 H19E H 0.4401 0.1385 0.2653 0.077 Uiso 0.222(6) 1 calc PR A 2 H19F H 0.3605 0.138 0.1068 0.077 Uiso 0.222(6) 1 calc PR A 2 C20A C 0.533(2) 0.0536(8) 0.305(2) 0.071(6) Uiso 0.222(6) 1 d PD A 2 H20D H 0.5506 0.0768 0.3779 0.106 Uiso 0.222(6) 1 calc PR A 2 H20E H 0.6161 0.0522 0.2756 0.106 Uiso 0.222(6) 1 calc PR A 2 H20F H 0.5158 0.0219 0.3357 0.106 Uiso 0.222(6) 1 calc PR A 2 H2 H 0.185(3) 0.0111(11) 0.115(3) 0.031(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.02731(16) 0.01806(15) 0.04343(19) 0.00258(12) 0.01314(13) 0.00185(11) P1 0.0158(3) 0.0184(3) 0.0204(3) 0.0005(2) 0.0065(3) 0.0004(2) O1 0.0159(9) 0.0271(9) 0.0183(9) 0.0010(7) 0.0065(7) 0.0007(7) O2 0.0155(9) 0.0221(9) 0.0174(9) 0.0003(7) 0.0051(7) -0.0004(7) N1 0.0195(11) 0.0183(11) 0.0205(11) -0.0036(9) 0.0032(9) -0.0010(9) O3 0.0224(9) 0.0209(9) 0.0233(9) -0.0014(7) 0.0064(8) -0.0005(7) C1 0.0228(13) 0.0274(14) 0.0168(13) 0.0036(10) 0.0054(11) 0.0039(11) C2 0.0190(13) 0.0246(13) 0.0168(12) -0.0009(10) 0.0026(10) 0.0033(10) C3 0.0142(12) 0.0262(14) 0.0226(13) -0.0005(11) 0.0020(10) 0.0010(10) C4 0.0249(14) 0.0241(14) 0.0221(13) -0.0004(11) 0.0046(11) 0.0033(11) C5 0.0282(15) 0.0385(17) 0.0235(14) 0.0008(12) -0.0002(12) 0.0066(13) C6 0.0168(12) 0.0248(13) 0.0190(12) 0.0017(10) 0.0092(10) 0.0010(10) C7 0.0151(12) 0.0292(14) 0.0188(12) 0.0021(11) 0.0040(10) -0.0001(10) C8 0.0241(15) 0.057(2) 0.0176(13) 0.0031(13) 0.0043(11) 0.0064(14) C9 0.0181(14) 0.0425(17) 0.0291(15) 0.0050(13) 0.0068(12) -0.0025(12) C10 0.0217(14) 0.0377(17) 0.0320(16) 0.0080(13) 0.0059(12) 0.0051(12) Se2 0.02964(17) 0.03209(17) 0.03439(18) 0.00119(12) 0.01454(13) 0.00545(12) P2 0.0213(3) 0.0226(3) 0.0203(3) -0.0057(3) 0.0099(3) -0.0045(3) O11 0.0269(10) 0.0241(10) 0.0215(9) -0.0060(7) 0.0113(8) -0.0036(8) O12 0.0242(10) 0.0230(9) 0.0206(9) -0.0072(7) 0.0098(8) -0.0067(7) N2 0.0234(12) 0.0239(12) 0.0217(12) -0.0065(10) 0.0119(10) -0.0053(9) O13 0.0337(11) 0.0322(11) 0.0332(11) -0.0141(9) 0.0161(9) -0.0118(9) C11 0.0230(14) 0.0292(14) 0.0206(13) -0.0038(11) 0.0071(11) -0.0047(11) C12 0.0246(14) 0.0241(13) 0.0223(13) -0.0041(10) 0.0122(11) -0.0051(11) C13 0.0259(14) 0.0210(13) 0.0263(14) -0.0042(11) 0.0129(12) -0.0026(11) C14 0.0259(15) 0.0262(14) 0.0318(15) -0.0034(11) 0.0156(12) -0.0048(11) C15 0.0296(16) 0.0346(16) 0.0347(16) 0.0042(13) 0.0168(13) 0.0023(13) C16 0.0233(14) 0.0252(13) 0.0201(13) -0.0010(11) 0.0056(11) -0.0046(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 P1 2.0655(7) . ? P1 O1 1.5889(18) . ? P1 O2 1.5898(17) . ? P1 N1 1.650(2) . ? O1 C1 1.463(3) . ? O2 C3 1.456(3) . ? N1 C6 1.396(3) . ? N1 H1 0.75(3) . ? O3 C6 1.214(3) . ? C1 C2 1.523(4) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.527(3) . ? C2 C5 1.533(3) . ? C2 C4 1.534(3) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 C7 1.528(3) . ? C7 C8 1.520(4) . ? C7 C10 1.537(4) . ? C7 C9 1.543(4) . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? Se2 P2 2.0647(8) . ? P2 O11 1.5745(18) . ? P2 O12 1.5760(18) . ? P2 N2 1.688(2) . ? O11 C11 1.470(3) . ? O12 C13 1.465(3) . ? N2 C16 1.382(3) . ? N2 H2 0.80(3) . ? O13 C16 1.218(3) . ? C11 C12 1.522(4) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 C15 1.526(4) . ? C12 C13 1.528(4) . ? C12 C14 1.537(4) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 C17 1.520(6) . ? C16 C17A 1.574(19) . ? C17 C20 1.498(7) . ? C17 C19 1.535(6) . ? C17 C18 1.536(6) . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C19 H19C 0.98 . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? C17A C18A 1.518(13) . ? C17A C20A 1.530(14) . ? C17A C19A 1.542(13) . ? C18A H18D 0.98 . ? C18A H18E 0.98 . ? C18A H18F 0.98 . ? C19A H19D 0.98 . ? C19A H19E 0.98 . ? C19A H19F 0.98 . ? C20A H20D 0.98 . ? C20A H20E 0.98 . ? C20A H20F 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O2 103.31(9) . . ? O1 P1 N1 103.40(11) . . ? O2 P1 N1 105.13(10) . . ? O1 P1 Se1 115.18(7) . . ? O2 P1 Se1 114.72(7) . . ? N1 P1 Se1 113.76(9) . . ? C1 O1 P1 115.12(15) . . ? C3 O2 P1 115.42(15) . . ? C6 N1 P1 125.50(19) . . ? C6 N1 H1 120(2) . . ? P1 N1 H1 114(2) . . ? O1 C1 C2 111.40(19) . . ? O1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? O1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 108 . . ? C1 C2 C3 108.6(2) . . ? C1 C2 C5 107.5(2) . . ? C3 C2 C5 108.9(2) . . ? C1 C2 C4 111.1(2) . . ? C3 C2 C4 110.6(2) . . ? C5 C2 C4 110.0(2) . . ? O2 C3 C2 111.32(19) . . ? O2 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? O2 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O3 C6 N1 120.4(2) . . ? O3 C6 C7 123.2(2) . . ? N1 C6 C7 116.4(2) . . ? C8 C7 C6 110.5(2) . . ? C8 C7 C10 109.1(2) . . ? C6 C7 C10 108.4(2) . . ? C8 C7 C9 110.3(2) . . ? C6 C7 C9 108.3(2) . . ? C10 C7 C9 110.1(2) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O11 P2 O12 106.10(10) . . ? O11 P2 N2 106.76(11) . . ? O12 P2 N2 100.32(10) . . ? O11 P2 Se2 112.54(7) . . ? O12 P2 Se2 111.99(8) . . ? N2 P2 Se2 117.89(9) . . ? C11 O11 P2 118.77(15) . . ? C13 O12 P2 119.33(16) . . ? C16 N2 P2 122.95(19) . . ? C16 N2 H2 120(2) . . ? P2 N2 H2 113(2) . . ? O11 C11 C12 111.2(2) . . ? O11 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? O11 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108 . . ? C11 C12 C15 107.6(2) . . ? C11 C12 C13 108.2(2) . . ? C15 C12 C13 108.6(2) . . ? C11 C12 C14 111.3(2) . . ? C15 C12 C14 110.9(2) . . ? C13 C12 C14 110.1(2) . . ? O12 C13 C12 111.0(2) . . ? O12 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? O12 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 108 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O13 C16 N2 118.9(2) . . ? O13 C16 C17 123.6(3) . . ? N2 C16 C17 117.5(3) . . ? O13 C16 C17A 123.9(5) . . ? N2 C16 C17A 116.6(5) . . ? C17 C16 C17A 8.8(7) . . ? C20 C17 C16 111.9(4) . . ? C20 C17 C19 112.0(4) . . ? C16 C17 C19 109.4(4) . . ? C20 C17 C18 110.3(4) . . ? C16 C17 C18 107.3(4) . . ? C19 C17 C18 105.6(4) . . ? C18A C17A C20A 92.1(15) . . ? C18A C17A C19A 128.6(16) . . ? C20A C17A C19A 100.2(14) . . ? C18A C17A C16 114.4(12) . . ? C20A C17A C16 112.2(14) . . ? C19A C17A C16 106.5(12) . . ? C17A C18A H18D 109.5 . . ? C17A C18A H18E 109.5 . . ? H18D C18A H18E 109.5 . . ? C17A C18A H18F 109.5 . . ? H18D C18A H18F 109.5 . . ? H18E C18A H18F 109.5 . . ? C17A C19A H19D 109.5 . . ? C17A C19A H19E 109.4 . . ? H19D C19A H19E 109.5 . . ? C17A C19A H19F 109.5 . . ? H19D C19A H19F 109.5 . . ? H19E C19A H19F 109.5 . . ? C17A C20A H20D 109.5 . . ? C17A C20A H20E 109.5 . . ? H20D C20A H20E 109.5 . . ? C17A C20A H20F 109.5 . . ? H20D C20A H20F 109.5 . . ? H20E C20A H20F 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Se1 P1 N1 C6 173.37(18) . . . . ? Se2 P2 N2 C16 64.3(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O13 0.75(3) 2.16(3) 2.907(3) 171(3) . _chemical_name_common ;N-pivaloyl-2-amino-2-seleno-5,5-dimethyl-1,3,2- dioxaphosphorinan ; data_11a _database_code_depnum_ccdc_archive 'CCDC 717033' _audit_creation_date 2008-10-03T08:59:07-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2-amino-2-seleno-5,5-dimethyl-1,3,2-dioxaphosphorinan ; _chemical_formula_moiety 'C5 H12 N1 O2 P1 Se1' _chemical_formula_sum 'C5 H12 N O2 P Se' _chemical_formula_weight 228.09 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.7108(2) _cell_length_b 10.9466(3) _cell_length_c 10.9955(3) _cell_angle_alpha 90 _cell_angle_beta 103.130(3) _cell_angle_gamma 90 _cell_volume 903.83(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6344 _cell_measurement_theta_min 2.6549 _cell_measurement_theta_max 32.267 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.279 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.1887 _exptl_absorpt_correction_T_max 0.536 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 8.1883 _diffrn_measurement_device '4-axis \k geometry diffractometer' _diffrn_measurement_device_type 'KM4CCD, Oxford Diffraction' _diffrn_measurement_method '\w scans, 0.75 deg width' _diffrn_orient_matrix_ub_11 0.03395158 _diffrn_orient_matrix_ub_12 -0.031591151 _diffrn_orient_matrix_ub_13 0.0567201804 _diffrn_orient_matrix_ub_21 0.0185798306 _diffrn_orient_matrix_ub_22 0.0565247713 _diffrn_orient_matrix_ub_23 0.0317861578 _diffrn_orient_matrix_ub_31 -0.0862446883 _diffrn_orient_matrix_ub_32 -0.0002941651 _diffrn_orient_matrix_ub_33 0.0126342504 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_unetI/netI 0.0134 _diffrn_reflns_number 5956 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 1679 _reflns_number_gt 1538 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0431P)^2^+0.4379P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 1679 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0291 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_ref 0.0668 _refine_ls_wR_factor_gt 0.0648 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.741 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.108 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H1A H 0.193(4) 0.335(3) 0.708(3) 0.025(8) Uiso 1 1 d . . . H1B H 0.080(4) 0.397(3) 0.613(3) 0.028(7) Uiso 1 1 d . . . Se1 Se 0.20083(3) 0.66759(2) 0.591333(19) 0.02200(11) Uani 1 1 d . . . P1 P 0.30356(7) 0.50620(5) 0.68227(5) 0.01629(15) Uani 1 1 d . . . O1 O 0.4677(2) 0.45148(15) 0.63588(14) 0.0212(4) Uani 1 1 d . . . O2 O 0.37918(19) 0.52191(15) 0.82856(13) 0.0186(3) Uani 1 1 d . . . N1 N 0.1600(3) 0.3988(2) 0.6743(2) 0.0277(5) Uani 1 1 d . . . C1 C 0.6388(3) 0.5154(2) 0.6751(2) 0.0228(5) Uani 1 1 d . . . H1C H 0.6272 0.5995 0.641 0.027 Uiso 1 1 calc R . . H1D H 0.7306 0.4724 0.6413 0.027 Uiso 1 1 calc R . . C2 C 0.6966(3) 0.5204(2) 0.8182(2) 0.0186(5) Uani 1 1 d . . . C3 C 0.5506(3) 0.5849(2) 0.8668(2) 0.0176(5) Uani 1 1 d . . . H3A H 0.5853 0.5888 0.9591 0.021 Uiso 1 1 calc R . . H3B H 0.538 0.6697 0.8347 0.021 Uiso 1 1 calc R . . C4 C 0.7287(3) 0.3924(2) 0.8728(2) 0.0245(5) Uani 1 1 d . . . H4A H 0.6234 0.3417 0.8411 0.037 Uiso 1 1 calc R . . H4B H 0.7514 0.3969 0.9641 0.037 Uiso 1 1 calc R . . H4C H 0.8321 0.3563 0.8484 0.037 Uiso 1 1 calc R . . C5 C 0.8653(3) 0.5982(2) 0.8541(2) 0.0267(5) Uani 1 1 d . . . H5A H 0.9013 0.605 0.9452 0.04 Uiso 1 1 calc R . . H5B H 0.8416 0.6798 0.8174 0.04 Uiso 1 1 calc R . . H5C H 0.961 0.5595 0.8225 0.04 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.02689(17) 0.01779(17) 0.01697(16) 0.00102(8) -0.00411(10) 0.00225(9) P1 0.0176(3) 0.0175(3) 0.0117(3) 0.0000(2) -0.0011(2) 0.0003(2) O1 0.0212(8) 0.0259(9) 0.0144(7) -0.0056(7) -0.0005(6) 0.0022(7) O2 0.0163(7) 0.0267(9) 0.0116(7) 0.0001(6) 0.0007(6) -0.0002(6) N1 0.0256(11) 0.0248(12) 0.0254(12) 0.0067(9) -0.0097(9) -0.0060(9) C1 0.0190(11) 0.0335(14) 0.0154(11) -0.0030(10) 0.0023(8) -0.0013(10) C2 0.0170(10) 0.0225(12) 0.0150(11) -0.0033(9) 0.0012(8) 0.0009(9) C3 0.0168(10) 0.0212(12) 0.0124(10) -0.0013(9) -0.0020(8) -0.0011(9) C4 0.0220(11) 0.0239(12) 0.0238(12) -0.0005(10) -0.0027(9) 0.0054(10) C5 0.0212(11) 0.0319(14) 0.0255(12) -0.0004(11) 0.0021(9) -0.0023(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 P1 2.0948(6) . ? P1 O1 1.5855(16) . ? P1 O2 1.5909(15) . ? P1 N1 1.604(2) . ? O1 C1 1.469(3) . ? O2 C3 1.466(3) . ? N1 H1A 0.81(3) . ? N1 H1B 0.81(3) . ? C1 C2 1.536(3) . ? C1 H1C 0.99 . ? C1 H1D 0.99 . ? C2 C4 1.522(3) . ? C2 C3 1.525(3) . ? C2 C5 1.529(3) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O2 103.30(8) . . ? O1 P1 N1 107.27(11) . . ? O2 P1 N1 102.97(11) . . ? O1 P1 Se1 114.08(7) . . ? O2 P1 Se1 113.80(7) . . ? N1 P1 Se1 114.26(10) . . ? C1 O1 P1 117.06(14) . . ? C3 O2 P1 116.14(13) . . ? P1 N1 H1A 118(2) . . ? P1 N1 H1B 117(2) . . ? H1A N1 H1B 118(3) . . ? O1 C1 C2 110.47(18) . . ? O1 C1 H1C 109.6 . . ? C2 C1 H1C 109.6 . . ? O1 C1 H1D 109.6 . . ? C2 C1 H1D 109.6 . . ? H1C C1 H1D 108.1 . . ? C4 C2 C3 110.80(19) . . ? C4 C2 C5 110.96(19) . . ? C3 C2 C5 107.71(19) . . ? C4 C2 C1 110.78(19) . . ? C3 C2 C1 108.06(18) . . ? C5 C2 C1 108.41(19) . . ? O2 C3 C2 111.76(18) . . ? O2 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? O2 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 O1 C1 -50.51(17) . . . . ? N1 P1 O1 C1 -158.87(16) . . . . ? Se1 P1 O1 C1 73.53(15) . . . . ? O1 P1 O2 C3 49.71(16) . . . . ? N1 P1 O2 C3 161.26(16) . . . . ? Se1 P1 O2 C3 -74.52(15) . . . . ? P1 O1 C1 C2 58.6(2) . . . . ? O1 C1 C2 C4 63.4(2) . . . . ? O1 C1 C2 C3 -58.1(2) . . . . ? O1 C1 C2 C5 -174.62(19) . . . . ? P1 O2 C3 C2 -58.3(2) . . . . ? C4 C2 C3 O2 -62.8(2) . . . . ? C5 C2 C3 O2 175.63(17) . . . . ? C1 C2 C3 O2 58.7(2) . . . . ? Se1 P1 N1 H1A -180(2) . . . . ? Se1 P1 N1 H1B 31(2) . . . . ? #END _chemical_name_common 2-amino-2-seleno-5,5-dimethyl-1,3,2-dioxaphosphorinan