#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/19/2011996.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2011996 loop_ _publ_author_name 'Linden, Anthony' 'Ghorbani-Salman Pour, Fatemeh' 'Breitenmoser, Roland A.' 'Heimgartner, Heinz' _publ_section_title ; (+-)-6-Benzyl-3,3-dimethylmorpholine-2,5-dione and its 5-monothio and 2,5-dithio derivatives ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 634 _journal_page_last 637 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C13 H15 N O2 S' _chemical_formula_sum 'C13 H15 N O2 S' _chemical_formula_weight 249.33 _chemical_melting_point 448.5(5) _chemical_name_systematic ; 6-benzyl-3,3-dimethyl-5-thioxomorpholin-2-one ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 112.70(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.901(4) _cell_length_b 5.843(6) _cell_length_c 16.559(5) _cell_measurement_reflns_used 24 _cell_measurement_temperature 173.0(10) _cell_measurement_theta_max 20.0 _cell_measurement_theta_min 18.0 _cell_volume 1240.8(14) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1999)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2001)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 173.0(10) _diffrn_measured_fraction_theta_full .998 _diffrn_measured_fraction_theta_max .998 _diffrn_measurement_device_type 'Rigaku AFC-5R diffractometer' _diffrn_measurement_method '\w--2\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode generator' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71069 _diffrn_reflns_av_R_equivalents .0340 _diffrn_reflns_av_sigmaI/netI .0610 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 3261 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.67 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .250 _exptl_absorpt_correction_T_max .963 _exptl_absorpt_correction_T_min .696 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 528 _exptl_crystal_size_max .50 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .15 _refine_diff_density_max .526 _refine_diff_density_min -.357 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 160 _refine_ls_number_reflns 2854 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all .0988 _refine_ls_R_factor_gt .0524 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0820P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1510 _reflns_number_gt 1926 _reflns_number_total 2854 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file sk1460.cif _[local]_cod_data_source_block V _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '448-449' was changed to '448.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '448-449' was changed to '448.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1240.7(13) _cod_database_code 2011996 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S5 .62224(5) -.06702(12) .63839(4) .0320(2) Uani d . 1 . . S O1 .81373(12) .4508(3) .64124(10) .0253(4) Uani d . 1 . . O O2 .98048(14) .4688(3) .66856(13) .0366(5) Uani d . 1 . . O N4 .81735(15) -.0209(3) .65326(13) .0234(4) Uani d . 1 . . N H4 .8240(18) -.173(5) .6609(15) .022(6) Uiso d . 1 . . H C2 .90599(18) .3483(4) .65683(15) .0250(5) Uani d . 1 . . C C3 .91534(17) .0890(4) .66001(15) .0230(5) Uani d . 1 . . C C5 .72653(17) .0749(4) .63857(14) .0233(5) Uani d . 1 . . C C6 .71576(17) .3293(4) .62064(15) .0237(5) Uani d . 1 . . C H6 .6811 .3960 .6581 .028 Uiso calc R 1 . . H C7 1.00011(18) .0211(4) .74852(15) .0267(5) Uani d . 1 . . C H81 1.0087 -.1455 .7510 .040 Uiso calc R 1 . . H H82 .9795 .0716 .7960 .040 Uiso calc R 1 . . H H83 1.0662 .0940 .7550 .040 Uiso calc R 1 . . H C8 .94441(19) .0124(4) .58386(16) .0276(5) Uani d . 1 . . C H71 1.0094 .0875 .5884 .041 Uiso calc R 1 . . H H72 .8885 .0548 .5283 .041 Uiso calc R 1 . . H H73 .9540 -.1540 .5861 .041 Uiso calc R 1 . . H C9 .64598(18) .3850(4) .52460(15) .0278(5) Uani d . 1 . . C H91 .5773 .3104 .5099 .033 Uiso calc R 1 . . H H92 .6343 .5524 .5187 .033 Uiso calc R 1 . . H C10 .69169(18) .3079(4) .45982(15) .0255(5) Uani d . 1 . . C C11 .66486(18) .0969(4) .41769(15) .0269(5) Uani d . 1 . . C H11 .6179 -.0010 .4303 .032 Uiso calc R 1 . . H C12 .7063(2) .0288(5) .35738(15) .0328(6) Uani d . 1 . . C H12 .6869 -.1146 .3286 .039 Uiso calc R 1 . . H C13 .7756(2) .1693(5) .33920(16) .0369(7) Uani d . 1 . . C H13 .8040 .1217 .2982 .044 Uiso calc R 1 . . H C14 .8036(2) .3788(5) .38066(17) .0367(6) Uani d . 1 . . C H14 .8516 .4748 .3685 .044 Uiso calc R 1 . . H C15 .7611(2) .4480(5) .44020(16) .0300(6) Uani d . 1 . . C H15 .7796 .5929 .4679 .036 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S5 .0266(3) .0407(4) .0339(4) -.0049(3) .0176(3) .0004(3) O1 .0260(8) .0238(8) .0272(8) .0013(7) .0115(7) -.0012(7) O2 .0316(10) .0290(10) .0511(11) -.0073(8) .0181(9) .0009(8) N4 .0254(10) .0197(10) .0273(10) -.0001(8) .0127(8) -.0007(8) C2 .0287(12) .0260(12) .0223(11) .0009(10) .0121(9) .0002(9) C3 .0212(11) .0253(12) .0253(11) -.0023(9) .0121(9) -.0020(9) C5 .0250(11) .0327(13) .0147(10) -.0003(10) .0105(9) -.0017(9) C6 .0227(11) .0300(12) .0221(11) .0000(10) .0125(9) -.0021(9) C7 .0267(12) .0306(13) .0233(11) .0011(10) .0101(10) -.0003(9) C8 .0276(12) .0330(13) .0258(12) .0027(10) .0141(10) .0010(10) C9 .0240(11) .0343(14) .0263(12) .0069(10) .0110(10) .0015(10) C10 .0235(11) .0318(13) .0203(11) .0055(10) .0074(9) .0071(9) C11 .0254(11) .0323(14) .0220(11) .0002(10) .0081(9) .0036(10) C12 .0345(14) .0387(15) .0202(12) .0067(11) .0049(10) -.0033(10) C13 .0347(14) .0563(18) .0218(12) .0131(13) .0132(11) .0028(12) C14 .0293(13) .0540(18) .0301(13) .0018(13) .0152(11) .0131(13) C15 .0320(13) .0327(13) .0236(12) -.0006(11) .0088(10) .0035(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S5 C5 . 1.669(2) yes O1 C2 . 1.347(3) yes O1 C6 . 1.455(3) yes O2 C2 . 1.204(3) yes N4 C3 . 1.470(3) yes N4 C5 . 1.315(3) yes N4 H4 . .90(3) ? C2 C3 . 1.520(4) ? C3 C7 . 1.536(3) ? C3 C8 . 1.532(3) ? C5 C6 . 1.512(4) ? C6 C9 . 1.544(3) ? C6 H6 . 1.0000 ? C7 H81 . .9800 ? C7 H82 . .9800 ? C7 H83 . .9800 ? C8 H71 . .9800 ? C8 H72 . .9800 ? C8 H73 . .9800 ? C9 C10 . 1.511(3) ? C9 H91 . .9900 ? C9 H92 . .9900 ? C10 C11 . 1.394(4) ? C10 C15 . 1.396(4) ? C11 C12 . 1.389(4) ? C11 H11 . .9500 ? C12 C13 . 1.385(4) ? C12 H12 . .9500 ? C13 C14 . 1.384(4) ? C13 H13 . .9500 ? C14 C15 . 1.391(4) ? C14 H14 . .9500 ? C15 H15 . .9500 ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H .0000 .0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N .0061 .0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O .0106 .0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; S S .1246 .1234 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 0 4 -1 0 5 1 0 5 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 O1 C6 124.30(19) yes C5 N4 C3 128.6(2) yes C5 N4 H4 119.2(16) ? C3 N4 H4 112.3(16) ? O2 C2 O1 117.8(2) ? O2 C2 C3 121.4(2) ? O1 C2 C3 120.8(2) ? N4 C3 C2 111.61(19) ? N4 C3 C8 109.92(19) ? C2 C3 C8 107.99(19) ? N4 C3 C7 107.86(18) ? C2 C3 C7 108.32(19) ? C8 C3 C7 111.15(19) ? N4 C5 C6 118.0(2) ? N4 C5 S5 124.1(2) ? C6 C5 S5 117.90(17) ? O1 C6 C5 114.91(19) ? O1 C6 C9 107.32(18) ? C5 C6 C9 112.62(19) ? O1 C6 H6 107.2 ? C5 C6 H6 107.2 ? C9 C6 H6 107.2 ? C3 C7 H81 109.5 ? C3 C7 H82 109.5 ? H81 C7 H82 109.5 ? C3 C7 H83 109.5 ? H81 C7 H83 109.5 ? H82 C7 H83 109.5 ? C3 C8 H71 109.5 ? C3 C8 H72 109.5 ? H71 C8 H72 109.5 ? C3 C8 H73 109.5 ? H71 C8 H73 109.5 ? H72 C8 H73 109.5 ? C10 C9 C6 113.52(19) ? C10 C9 H91 108.9 ? C6 C9 H91 108.9 ? C10 C9 H92 108.9 ? C6 C9 H92 108.9 ? H91 C9 H92 107.7 ? C11 C10 C15 118.5(2) ? C11 C10 C9 120.9(2) ? C15 C10 C9 120.5(2) ? C12 C11 C10 120.5(2) ? C12 C11 H11 119.7 ? C10 C11 H11 119.7 ? C13 C12 C11 120.2(2) ? C13 C12 H12 119.9 ? C11 C12 H12 119.9 ? C14 C13 C12 120.2(2) ? C14 C13 H13 119.9 ? C12 C13 H13 119.9 ? C13 C14 C15 119.6(3) ? C13 C14 H14 120.2 ? C15 C14 H14 120.2 ? C14 C15 C10 121.0(3) ? C14 C15 H15 119.5 ? C10 C15 H15 119.5 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N4 H4 O1 1_545 .90(3) 2.22(3) 3.092(4) 164(2) yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C6 O1 C2 O2 176.1(2) C6 O1 C2 C3 -4.3(3) C5 N4 C3 C2 5.8(3) C5 N4 C3 C8 -114.0(2) C5 N4 C3 C7 124.7(2) O2 C2 C3 N4 173.9(2) O1 C2 C3 N4 -5.7(3) O2 C2 C3 C8 -65.2(3) O1 C2 C3 C8 115.2(2) O2 C2 C3 C7 55.3(3) O1 C2 C3 C7 -124.3(2) C3 N4 C5 C6 4.0(3) C3 N4 C5 S5 -176.09(17) C2 O1 C6 C5 14.0(3) C2 O1 C6 C9 -112.1(2) N4 C5 C6 O1 -13.5(3) S5 C5 C6 O1 166.56(14) N4 C5 C6 C9 109.8(2) S5 C5 C6 C9 -70.1(2) O1 C6 C9 C10 61.4(3) C5 C6 C9 C10 -66.0(3) C6 C9 C10 C11 94.7(3) C6 C9 C10 C15 -86.0(3) C15 C10 C11 C12 -.2(3) C9 C10 C11 C12 179.2(2) C10 C11 C12 C13 .7(4) C11 C12 C13 C14 -.3(4) C12 C13 C14 C15 -.5(4) C13 C14 C15 C10 .9(4) C11 C10 C15 C14 -.6(3) C9 C10 C15 C14 -180.0(2)