#------------------------------------------------------------------------------ #$Date: 2008-04-03 11:11:48 +0100 (Thu, 03 Apr 2008) $ #$Revision: 326 $ #$URL: svn://www.crystallography.net/cod/cif/2/2206852.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_2206852 loop_ _publ_author_name 'Jiang, Kai' 'Chang, Jiu-Li' 'Wang, Li-Ya' 'Ma, Lu-Fang' 'Wang, Yu-Fang' _publ_section_title ; 4,4,5,5-Tetramethyl-2-thiazol-2-ylimidazolidine-1,3-diol ; _journal_coeditor_code BH6030 _journal_issue 10 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o3430 _journal_page_last o3432 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C10 H17 N3 O2 S' _chemical_formula_moiety 'C10 H17 N3 O2 S' _chemical_formula_sum 'C10 H17 N3 O2 S' _chemical_formula_weight 243.33 _chemical_name_systematic ; 4,4,5,5-Tetramethyl-2-thiazol-2-ylimidazolidine-1,3-diol ; _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 107.3670(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.9785(5) _cell_length_b 18.7982(13) _cell_length_c 10.0764(7) _cell_measurement_reflns_used 4327 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 27.64 _cell_measurement_theta_min 3.03 _cell_volume 1261.59(15) _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_collection 'SMART (Bruker, 2002)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Bruker, 2002)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0148 _diffrn_reflns_av_sigmaI/netI 0.0136 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 10799 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 3.03 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.248 _exptl_absorpt_correction_T_max 0.9336 _exptl_absorpt_correction_T_min 0.9093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.28 _refine_diff_density_max 0.489 _refine_diff_density_min -0.331 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 151 _refine_ls_number_reflns 2886 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0525 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0644P)^2^+0.6505P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1387 _refine_ls_wR_factor_ref 0.1483 _reflns_number_gt 2326 _reflns_number_total 2886 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bh6030.cif 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' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol S1 0.08575(9) 0.63584(5) 0.48980(7) 0.0742(3) Uani d . 1 S O1 0.5623(2) 0.74143(7) 0.72796(16) 0.0547(4) Uani d . 1 O H1 0.4925 0.7654 0.7635 0.082 Uiso calc R 1 H O2 0.7023(2) 0.54614(9) 0.55417(17) 0.0579(4) Uani d . 1 O H2 0.6727 0.5109 0.5043 0.087 Uiso calc R 1 H N1 0.3076(3) 0.68503(10) 0.35203(18) 0.0564(5) Uani d . 1 N N2 0.4980(3) 0.66873(8) 0.71949(15) 0.0416(4) Uani d . 1 N N3 0.5373(2) 0.56442(8) 0.60613(15) 0.0395(4) Uani d . 1 N C1 -0.0274(4) 0.66449(16) 0.3255(3) 0.0759(8) Uani d . 1 C H1A -0.1650 0.6634 0.2812 0.091 Uiso calc R 1 H C2 0.1094(5) 0.68864(15) 0.2694(3) 0.0754(8) Uani d . 1 C H2A 0.0744 0.7070 0.1797 0.091 Uiso calc R 1 H C3 0.3157(3) 0.65796(10) 0.47212(19) 0.0418(4) Uani d . 1 C C4 0.5066(3) 0.64225(9) 0.58516(17) 0.0377(4) Uani d . 1 C H4 0.6211 0.6635 0.5622 0.045 Uiso calc R 1 H C5 0.5835(4) 0.55112(11) 0.7620(2) 0.0547(6) Uani d . 1 C C6 0.6467(4) 0.62476(11) 0.8261(2) 0.0537(5) Uani d . 1 C C7 0.3797(5) 0.52849(15) 0.7822(3) 0.0742(8) Uani d . 1 C H7A 0.3266 0.4885 0.7236 0.111 Uiso calc R 1 H H7B 0.2867 0.5674 0.7580 0.111 Uiso calc R 1 H H7C 0.4000 0.5156 0.8777 0.111 Uiso calc R 1 H C8 0.7338(5) 0.49203(13) 0.8116(3) 0.0736(8) Uani d . 1 C H8A 0.6788 0.4484 0.7668 0.110 Uiso calc R 1 H H8B 0.7635 0.4868 0.9105 0.110 Uiso calc R 1 H H8C 0.8547 0.5032 0.7892 0.110 Uiso calc R 1 H C9 0.6168(5) 0.63854(13) 0.9663(2) 0.0689(7) Uani d . 1 C H9A 0.6683 0.6848 0.9990 0.103 Uiso calc R 1 H H9B 0.6869 0.6030 1.0312 0.103 Uiso calc R 1 H H9C 0.4762 0.6366 0.9579 0.103 Uiso calc R 1 H C10 0.8690(4) 0.64071(15) 0.8348(3) 0.0728(7) Uani d . 1 C H10A 0.8951 0.6241 0.7517 0.109 Uiso calc R 1 H H10B 0.9567 0.6169 0.9140 0.109 Uiso calc R 1 H H10C 0.8924 0.6911 0.8438 0.109 Uiso calc R 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0440(3) 0.1121(6) 0.0640(4) 0.0035(3) 0.0121(3) 0.0014(4) O1 0.0654(10) 0.0340(7) 0.0605(9) -0.0081(6) 0.0124(7) -0.0061(6) O2 0.0459(8) 0.0671(10) 0.0639(10) 0.0002(7) 0.0214(7) -0.0231(8) N1 0.0729(12) 0.0464(9) 0.0412(9) 0.0012(9) 0.0035(8) 0.0095(7) N2 0.0585(10) 0.0317(7) 0.0327(8) -0.0056(7) 0.0106(7) -0.0034(6) N3 0.0445(8) 0.0435(8) 0.0301(7) 0.0045(6) 0.0108(6) -0.0031(6) C1 0.0584(15) 0.0778(17) 0.0724(17) 0.0214(13) -0.0097(13) -0.0113(14) C2 0.0865(19) 0.0641(15) 0.0529(14) 0.0170(14) -0.0139(13) 0.0081(12) C3 0.0475(10) 0.0381(9) 0.0367(9) 0.0025(7) 0.0080(8) -0.0011(7) C4 0.0412(9) 0.0409(9) 0.0306(8) -0.0042(7) 0.0102(7) 0.0004(7) C5 0.0834(16) 0.0424(10) 0.0327(9) 0.0050(10) 0.0088(9) -0.0002(8) C6 0.0786(15) 0.0433(10) 0.0328(10) 0.0035(10) 0.0070(9) -0.0006(8) C7 0.105(2) 0.0705(16) 0.0530(14) -0.0303(15) 0.0326(14) 0.0048(12) C8 0.110(2) 0.0477(12) 0.0493(13) 0.0195(13) 0.0031(13) 0.0029(10) C9 0.111(2) 0.0579(14) 0.0324(11) 0.0008(13) 0.0131(12) -0.0047(9) C10 0.0594(14) 0.0714(16) 0.0691(16) -0.0052(12) -0.0089(12) 0.0058(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C1 1.696(3) yes S1 C3 1.718(2) yes O1 N2 1.4330(19) yes O1 H1 0.8200 ? O2 N3 1.4415(19) yes O2 H2 0.8200 ? N1 C3 1.298(3) yes N1 C2 1.387(3) yes N2 C4 1.460(2) yes N2 C6 1.500(3) yes N3 C4 1.484(2) yes N3 C5 1.526(2) yes C1 C2 1.326(4) yes C1 H1A 0.9300 ? C2 H2A 0.9300 ? C3 C4 1.501(3) ? C4 H4 0.9800 ? C5 C8 1.507(3) ? C5 C6 1.536(3) yes C5 C7 1.555(4) ? C6 C9 1.511(3) ? C6 C10 1.557(4) ? C7 H7A 0.9600 ? C7 H7B 0.9600 ? C7 H7C 0.9600 ? C8 H8A 0.9600 ? C8 H8B 0.9600 ? C8 H8C 0.9600 ? C9 H9A 0.9600 ? C9 H9B 0.9600 ? C9 H9C 0.9600 ? C10 H10A 0.9600 ? C10 H10B 0.9600 ? C10 H10C 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_publ_flag C1 S1 C3 89.95(13) yes N2 O1 H1 109.5 ? N3 O2 H2 109.5 ? C3 N1 C2 109.7(2) yes O1 N2 C4 106.35(13) yes O1 N2 C6 110.21(15) yes C4 N2 C6 105.36(15) yes O2 N3 C4 106.26(14) yes O2 N3 C5 112.83(15) yes C4 N3 C5 106.57(13) yes C2 C1 S1 109.9(2) ? C2 C1 H1A 125.1 ? S1 C1 H1A 125.1 ? C1 C2 N1 116.3(2) ? C1 C2 H2A 121.8 ? N1 C2 H2A 121.8 ? N1 C3 C4 124.49(18) ? N1 C3 S1 114.17(16) ? C4 C3 S1 121.24(14) ? N2 C4 N3 104.37(13) ? N2 C4 C3 111.31(16) ? N3 C4 C3 111.07(14) ? N2 C4 H4 110.0 ? N3 C4 H4 110.0 ? C3 C4 H4 110.0 ? C8 C5 N3 112.03(18) ? C8 C5 C6 116.1(2) ? N3 C5 C6 103.36(15) ? C8 C5 C7 109.1(2) ? N3 C5 C7 105.03(18) ? C6 C5 C7 110.5(2) ? N2 C6 C9 108.42(19) ? N2 C6 C5 98.34(16) ? C9 C6 C5 116.5(2) ? N2 C6 C10 113.51(18) ? C9 C6 C10 109.2(2) ? C5 C6 C10 110.7(2) ? C5 C7 H7A 109.5 ? C5 C7 H7B 109.5 ? H7A C7 H7B 109.5 ? C5 C7 H7C 109.5 ? H7A C7 H7C 109.5 ? H7B C7 H7C 109.5 ? C5 C8 H8A 109.5 ? C5 C8 H8B 109.5 ? H8A C8 H8B 109.5 ? C5 C8 H8C 109.5 ? H8A C8 H8C 109.5 ? H8B C8 H8C 109.5 ? C6 C9 H9A 109.5 ? C6 C9 H9B 109.5 ? H9A C9 H9B 109.5 ? C6 C9 H9C 109.5 ? H9A C9 H9C 109.5 ? H9B C9 H9C 109.5 ? C6 C10 H10A 109.5 ? C6 C10 H10B 109.5 ? H10A C10 H10B 109.5 ? C6 C10 H10C 109.5 ? H10A C10 H10C 109.5 ? H10B C10 H10C 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 C3 S1 C1 C2 -0.5(2) S1 C1 C2 N1 0.6(3) C3 N1 C2 C1 -0.5(3) C2 N1 C3 C4 176.40(19) C2 N1 C3 S1 0.1(2) C1 S1 C3 N1 0.22(18) C1 S1 C3 C4 -176.23(17) O1 N2 C4 N3 153.55(14) C6 N2 C4 N3 36.55(18) O1 N2 C4 C3 -86.57(17) C6 N2 C4 C3 156.43(16) O2 N3 C4 N2 -130.74(14) C5 N3 C4 N2 -10.17(19) O2 N3 C4 C3 109.22(16) C5 N3 C4 C3 -130.22(17) N1 C3 C4 N2 132.84(19) S1 C3 C4 N2 -51.1(2) N1 C3 C4 N3 -111.3(2) S1 C3 C4 N3 64.75(19) O2 N3 C5 C8 -28.2(3) C4 N3 C5 C8 -144.5(2) O2 N3 C5 C6 97.55(19) C4 N3 C5 C6 -18.7(2) O2 N3 C5 C7 -146.56(17) C4 N3 C5 C7 97.19(19) O1 N2 C6 C9 77.0(2) C4 N2 C6 C9 -168.64(18) O1 N2 C6 C5 -161.42(16) C4 N2 C6 C5 -47.08(19) O1 N2 C6 C10 -44.5(2) C4 N2 C6 C10 69.9(2) C8 C5 C6 N2 162.0(2) N3 C5 C6 N2 38.9(2) C7 C5 C6 N2 -73.0(2) C8 C5 C6 C9 -82.6(3) N3 C5 C6 C9 154.3(2) C7 C5 C6 C9 42.4(3) C8 C5 C6 C10 42.9(3) N3 C5 C6 C10 -80.2(2) C7 C5 C6 C10 167.85(19) 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 O1 H1 N1 4_576 0.82 2.00 2.821(3) 174 yes O2 H2 N3 3_666 0.82 2.10 2.848(2) 151 yes