#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/19/2011995.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_2011995 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 O3' _chemical_formula_sum 'C13 H15 N O3' _chemical_formula_weight 233.27 _chemical_melting_point 437.5(5) _chemical_name_systematic ; 6-benzyl-3,3-dimethylmorpholine-2,5-dione ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL-97 _cell_angle_alpha 67.51(2) _cell_angle_beta 80.38(3) _cell_angle_gamma 80.35(3) _cell_formula_units_Z 2 _cell_length_a 5.699(2) _cell_length_b 10.347(3) _cell_length_c 11.327(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 173.0(10) _cell_measurement_theta_max 20.0 _cell_measurement_theta_min 19.0 _cell_volume 604.5(4) _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 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 173.0(10) _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _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 .0249 _diffrn_reflns_av_sigmaI/netI .0454 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 2927 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 3.39 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .0912 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 248 _exptl_crystal_size_max .50 _exptl_crystal_size_mid .38 _exptl_crystal_size_min .12 _refine_diff_density_max .266 _refine_diff_density_min -.230 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 160 _refine_ls_number_reflns 2773 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.018 _refine_ls_R_factor_all .0913 _refine_ls_R_factor_gt .0469 _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^)+(0.0530P)^2^+0.1854P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1302 _reflns_number_gt 1859 _reflns_number_total 2773 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file sk1460.cif _[local]_cod_data_source_block IV _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '437-438' was changed to '437.5(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 '437-438' was changed to '437.5(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_database_code 2011995 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 .4371(2) .10417(12) .63704(12) .0321(3) Uani d . 1 . . O O2 .7608(2) .11627(14) .50074(14) .0411(4) Uani d . 1 . . O O5 -.0837(3) .34956(14) .63550(14) .0520(5) Uani d . 1 . . O N4 .2406(3) .36142(15) .48846(14) .0283(3) Uani d . 1 . . N H4 .194(4) .451(2) .447(2) .043(6) Uiso d . 1 . . H C2 .5594(3) .16503(17) .52203(17) .0273(4) Uani d . 1 . . C C3 .4341(3) .29250(17) .42359(16) .0244(4) Uani d . 1 . . C C5 .1008(3) .29338(18) .59202(17) .0331(4) Uani d . 1 . . C C6 .1783(3) .13724(18) .65703(17) .0307(4) Uani d . 1 . . C H6 .0985 .0827 .6221 .037 Uiso calc R 1 . . H C7 .3359(3) .24227(19) .33272(17) .0322(4) Uani d . 1 . . C H71 .2569 .3232 .2676 .048 Uiso calc R 1 . . H H72 .2199 .1755 .3820 .048 Uiso calc R 1 . . H H73 .4680 .1959 .2904 .048 Uiso calc R 1 . . H C8 .6138(3) .39764(19) .34989(19) .0357(4) Uani d . 1 . . C H81 .7442 .3541 .3042 .054 Uiso calc R 1 . . H H82 .6793 .4253 .4103 .054 Uiso calc R 1 . . H H83 .5335 .4811 .2878 .054 Uiso calc R 1 . . H C9 .1099(4) .0907(2) .80091(18) .0471(6) Uani d . 1 . . C H91 .1972 .1411 .8354 .057 Uiso calc R 1 . . H H92 -.0636 .1186 .8177 .057 Uiso calc R 1 . . H C10 .1624(3) -.06485(18) .87193(16) .0308(4) Uani d . 1 . . C C11 .3570(4) -.1186(2) .94168(18) .0372(5) Uani d . 1 . . C H11 .4629 -.0565 .9410 .045 Uiso calc R 1 . . H C12 .4007(4) -.2604(2) 1.01209(19) .0421(5) Uani d . 1 . . C H12 .5341 -.2951 1.0603 .050 Uiso calc R 1 . . H C13 .2510(4) -.3511(2) 1.01230(19) .0422(5) Uani d . 1 . . C H13 .2787 -.4488 1.0614 .051 Uiso calc R 1 . . H C14 .0603(4) -.2996(2) .9409(2) .0468(5) Uani d . 1 . . C H14 -.0417 -.3626 .9393 .056 Uiso calc R 1 . . H C15 .0158(4) -.1580(2) .87165(19) .0399(5) Uani d . 1 . . C H15 -.1173 -.1240 .8232 .048 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 O1 .0329(7) .0264(6) .0288(6) .0042(5) -.0046(5) -.0038(5) O2 .0263(7) .0353(7) .0512(9) .0046(6) -.0026(6) -.0083(7) O5 .0594(10) .0288(7) .0400(8) .0160(7) .0195(7) -.0009(6) N4 .0347(8) .0184(7) .0246(7) .0050(6) .0020(6) -.0055(6) C2 .0266(9) .0239(8) .0309(9) .0000(7) -.0052(7) -.0098(7) C3 .0246(8) .0210(8) .0249(8) .0010(6) .0002(6) -.0080(6) C5 .0395(10) .0242(9) .0271(9) .0068(8) .0030(8) -.0070(7) C6 .0341(9) .0236(8) .0272(9) .0050(7) .0033(7) -.0077(7) C7 .0367(10) .0311(9) .0288(9) -.0010(8) -.0038(7) -.0119(8) C8 .0339(10) .0283(9) .0399(10) -.0055(8) .0006(8) -.0081(8) C9 .0725(15) .0259(10) .0300(10) .0051(10) .0101(10) -.0068(8) C10 .0408(10) .0243(8) .0212(8) .0009(7) .0062(7) -.0075(7) C11 .0461(11) .0377(10) .0317(10) -.0124(9) -.0005(8) -.0153(9) C12 .0435(11) .0463(12) .0305(10) .0010(9) -.0109(8) -.0074(9) C13 .0525(13) .0257(9) .0352(10) -.0007(9) .0001(9) -.0003(8) C14 .0499(13) .0371(11) .0535(13) -.0173(10) -.0045(10) -.0120(10) C15 .0341(10) .0427(11) .0376(10) -.0007(8) -.0090(8) -.0081(9) 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 O1 C2 . 1.340(2) yes O1 C6 . 1.457(2) yes O2 C2 . 1.199(2) yes O5 C5 . 1.236(2) yes N4 C5 . 1.323(2) yes N4 C3 . 1.460(2) yes N4 H4 . .88(2) ? C2 C3 . 1.522(2) ? C3 C8 . 1.524(2) ? C3 C7 . 1.530(3) ? C5 C6 . 1.519(2) ? C6 C9 . 1.513(3) ? C6 H6 . 1.0000 ? C7 H71 . .9800 ? C7 H72 . .9800 ? C7 H73 . .9800 ? C8 H81 . .9800 ? C8 H82 . .9800 ? C8 H83 . .9800 ? C9 C10 . 1.502(3) ? C9 H91 . .9900 ? C9 H92 . .9900 ? C10 C15 . 1.378(3) ? C10 C11 . 1.383(3) ? C11 C12 . 1.378(3) ? C11 H11 . .9500 ? C12 C13 . 1.369(3) ? C12 H12 . .9500 ? C13 C14 . 1.374(3) ? C13 H13 . .9500 ? C14 C15 . 1.375(3) ? 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 ; loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 1 -2 -1 -2 -3 -1 -3 -2 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 120.53(13) yes C5 N4 C3 124.06(14) yes C5 N4 H4 117.3(14) ? C3 N4 H4 117.2(14) ? O2 C2 O1 118.81(16) ? O2 C2 C3 122.98(16) ? O1 C2 C3 118.20(14) ? N4 C3 C2 110.10(13) ? N4 C3 C8 108.03(14) ? C2 C3 C8 108.97(14) ? N4 C3 C7 110.62(14) ? C2 C3 C7 108.25(14) ? C8 C3 C7 110.87(15) ? O5 C5 N4 123.78(16) ? O5 C5 C6 120.30(16) ? N4 C5 C6 115.92(15) ? O1 C6 C9 106.64(16) ? O1 C6 C5 111.79(15) ? C9 C6 C5 110.50(15) ? O1 C6 H6 109.3 ? C9 C6 H6 109.3 ? C5 C6 H6 109.3 ? C3 C7 H71 109.5 ? C3 C7 H72 109.5 ? H71 C7 H72 109.5 ? C3 C7 H73 109.5 ? H71 C7 H73 109.5 ? H72 C7 H73 109.5 ? C3 C8 H81 109.5 ? C3 C8 H82 109.5 ? H81 C8 H82 109.5 ? C3 C8 H83 109.5 ? H81 C8 H83 109.5 ? H82 C8 H83 109.5 ? C10 C9 C6 114.08(16) ? C10 C9 H91 108.7 ? C6 C9 H91 108.7 ? C10 C9 H92 108.7 ? C6 C9 H92 108.7 ? H91 C9 H92 107.6 ? C15 C10 C11 118.01(17) ? C15 C10 C9 121.09(19) ? C11 C10 C9 120.89(19) ? C12 C11 C10 121.43(19) ? C12 C11 H11 119.3 ? C10 C11 H11 119.3 ? C13 C12 C11 119.72(19) ? C13 C12 H12 120.1 ? C11 C12 H12 120.1 ? C12 C13 C14 119.49(19) ? C12 C13 H13 120.3 ? C14 C13 H13 120.3 ? C13 C14 C15 120.7(2) ? C13 C14 H14 119.7 ? C15 C14 H14 119.7 ? C14 C15 C10 120.63(19) ? C14 C15 H15 119.7 ? C10 C15 H15 119.7 ? 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 O5 2_566 .88(2) 1.95(2) 2.833(2) 176(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 -165.28(16) C6 O1 C2 C3 14.0(2) C5 N4 C3 C2 -37.3(2) C5 N4 C3 C8 -156.18(18) C5 N4 C3 C7 82.3(2) O2 C2 C3 N4 -156.84(17) O1 C2 C3 N4 23.9(2) O2 C2 C3 C8 -38.5(2) O1 C2 C3 C8 142.19(16) O2 C2 C3 C7 82.1(2) O1 C2 C3 C7 -97.14(18) C3 N4 C5 O5 -168.91(19) C3 N4 C5 C6 10.6(3) C2 O1 C6 C9 -162.18(16) C2 O1 C6 C5 -41.3(2) O5 C5 C6 O1 -151.95(18) N4 C5 C6 O1 28.5(2) O5 C5 C6 C9 -33.3(3) N4 C5 C6 C9 147.15(19) O1 C6 C9 C10 -62.9(2) C5 C6 C9 C10 175.40(18) C6 C9 C10 C15 -77.5(3) C6 C9 C10 C11 103.7(2) C15 C10 C11 C12 -1.8(3) C9 C10 C11 C12 176.93(18) C10 C11 C12 C13 .9(3) C11 C12 C13 C14 .8(3) C12 C13 C14 C15 -1.4(3) C13 C14 C15 C10 .4(3) C11 C10 C15 C14 1.2(3) C9 C10 C15 C14 -177.55(19)