# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_vol89 _database_code_depnum_ccdc_archive 'CCDC 888091' #TrackingRef 'vol89dep.cif' _audit_creation_date 2011-07-20 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; 1,1-Dioxo-tetrahydro-1?6-thiopyran-3-one ; _chemical_formula_moiety 'C5 H8 O3 S' _chemical_formula_sum 'C5 H8 O3 S' _chemical_formula_weight 148.17 _chemical_melting_point ? 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' 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 5.6790(8) _cell_length_b 5.8215(8) _cell_length_c 10.7072(14) _cell_angle_alpha 103.502(12) _cell_angle_beta 93.207(11) _cell_angle_gamma 107.717(12) _cell_volume 324.78(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1172 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.8925 _cell_measurement_theta_min 3.7948 _exptl_absorpt_coefficient_mu 0.426 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.96353 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 156 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0145 _diffrn_reflns_av_unetI/netI 0.0336 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 2058 _diffrn_reflns_theta_full 28.96 _diffrn_reflns_theta_max 28.96 _diffrn_reflns_theta_min 3.80 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.1827 _diffrn_measured_fraction_theta_full 0.860 _diffrn_measured_fraction_theta_max 0.860 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -86.00 -59.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -20.7749 136.0000 98.0000 27 #__ type_ start__ end____ width___ exp.time_ 2 omega -2.00 91.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 22.1812 37.0000 -90.0000 93 #__ type_ start__ end____ width___ exp.time_ 3 omega 44.00 79.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 22.1812 179.0000 150.0000 35 #__ type_ start__ end____ width___ exp.time_ 4 omega 1.00 80.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 22.1812 -132.0000 31.0000 79 #__ type_ start__ end____ width___ exp.time_ 5 omega -45.00 52.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 22.1812 -37.0000 90.0000 97 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.1120456000 _diffrn_orient_matrix_UB_12 -0.0112619000 _diffrn_orient_matrix_UB_13 0.0278538000 _diffrn_orient_matrix_UB_21 0.0695155000 _diffrn_orient_matrix_UB_22 0.0435776000 _diffrn_orient_matrix_UB_23 0.0628846000 _diffrn_orient_matrix_UB_31 0.0115957000 _diffrn_orient_matrix_UB_32 0.1247154000 _diffrn_orient_matrix_UB_33 -0.0001990000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1217 _reflns_number_total 1473 _reflns_odcompleteness_completeness 99.62 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)' _refine_diff_density_max 0.277 _refine_diff_density_min -0.407 _refine_diff_density_rms 0.051 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 82 _refine_ls_number_reflns 1473 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0403 _refine_ls_restrained_S_all 1.055 _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^)+(0.0312P)^2^+0.1876P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0877 _refine_ls_wR_factor_ref 0.0987 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 S1 S 0.34010(9) 0.24735(9) 0.62860(5) 0.03887(18) Uani 1 1 d . . . O1 O 0.2843(3) 0.1557(3) 0.49013(15) 0.0532(4) Uani 1 1 d . . . O2 O 0.2159(3) 0.4112(3) 0.69267(19) 0.0596(5) Uani 1 1 d . . . O3 O 0.8354(4) 0.6752(4) 0.87553(19) 0.0744(6) Uani 1 1 d . . . C1 C 0.6627(4) 0.4027(4) 0.6701(2) 0.0396(5) Uani 1 1 d . . . H1A H 0.7524 0.2977 0.6256 0.048 Uiso 1 1 calc R . . H1B H 0.7078 0.5559 0.6426 0.048 Uiso 1 1 calc R . . C2 C 0.7356(4) 0.4625(4) 0.8133(2) 0.0473(5) Uani 1 1 d . . . C3 C 0.6752(5) 0.2441(5) 0.8697(3) 0.0655(8) Uani 1 1 d . . . H3A H 0.7255 0.3030 0.9627 0.079 Uiso 1 1 calc R . . H3B H 0.7706 0.1374 0.8343 0.079 Uiso 1 1 calc R . . C4 C 0.3997(5) 0.0913(5) 0.8425(2) 0.0592(7) Uani 1 1 d . . . H4A H 0.3744 -0.0514 0.8784 0.071 Uiso 1 1 calc R . . H4B H 0.3067 0.1927 0.8868 0.071 Uiso 1 1 calc R . . C5 C 0.2957(4) -0.0016(4) 0.7005(2) 0.0450(5) Uani 1 1 d . . . H5A H 0.1189 -0.0932 0.6909 0.054 Uiso 1 1 calc R . . H5B H 0.3776 -0.1151 0.6565 0.054 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 S1 0.0317(3) 0.0373(3) 0.0500(3) 0.0174(2) 0.0029(2) 0.0107(2) O1 0.0496(10) 0.0595(10) 0.0456(9) 0.0207(8) -0.0062(7) 0.0080(8) O2 0.0440(9) 0.0518(10) 0.0891(14) 0.0163(9) 0.0131(9) 0.0253(8) O3 0.0743(14) 0.0588(12) 0.0634(12) -0.0006(9) -0.0005(10) -0.0019(10) C1 0.0313(10) 0.0395(11) 0.0467(12) 0.0164(9) 0.0046(9) 0.0059(9) C2 0.0361(11) 0.0496(13) 0.0484(13) 0.0107(10) -0.0001(10) 0.0054(10) C3 0.0673(18) 0.0704(18) 0.0510(16) 0.0297(13) -0.0113(13) 0.0047(14) C4 0.0678(17) 0.0590(15) 0.0461(14) 0.0255(11) 0.0093(12) 0.0048(13) C5 0.0443(12) 0.0365(11) 0.0514(13) 0.0179(9) 0.0052(10) 0.0047(9) _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 S1 O1 1.4347(17) . ? S1 O2 1.4268(17) . ? S1 C1 1.756(2) . ? S1 C5 1.754(2) . ? O3 C2 1.202(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C1 C2 1.495(3) . ? C2 C3 1.488(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 C4 1.518(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4 C5 1.508(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? 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 S1 C1 108.75(11) . . ? O1 S1 C5 110.53(11) . . ? O2 S1 O1 117.82(11) . . ? O2 S1 C1 107.63(11) . . ? O2 S1 C5 108.97(12) . . ? C5 S1 C1 101.93(11) . . ? S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? C2 C1 S1 110.51(15) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? O3 C2 C1 120.4(2) . . ? O3 C2 C3 124.1(2) . . ? C3 C2 C1 115.5(2) . . ? C2 C3 H3A 109.0 . . ? C2 C3 H3B 109.0 . . ? C2 C3 C4 112.9(2) . . ? H3A C3 H3B 107.8 . . ? C4 C3 H3A 109.0 . . ? C4 C3 H3B 109.0 . . ? C3 C4 H4A 108.7 . . ? C3 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C5 C4 C3 114.1(2) . . ? C5 C4 H4A 108.7 . . ? C5 C4 H4B 108.7 . . ? S1 C5 H5A 109.4 . . ? S1 C5 H5B 109.4 . . ? C4 C5 S1 111.13(16) . . ? C4 C5 H5A 109.4 . . ? C4 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? 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 S1 C1 C2 O3 -121.2(2) . . . . ? S1 C1 C2 C3 58.7(3) . . . . ? O1 S1 C1 C2 -170.23(15) . . . . ? O1 S1 C5 C4 169.10(17) . . . . ? O2 S1 C1 C2 61.09(18) . . . . ? O2 S1 C5 C4 -59.9(2) . . . . ? O3 C2 C3 C4 122.7(3) . . . . ? C1 S1 C5 C4 53.6(2) . . . . ? C1 C2 C3 C4 -57.1(3) . . . . ? C2 C3 C4 C5 56.0(3) . . . . ? C3 C4 C5 S1 -57.5(3) . . . . ? C5 S1 C1 C2 -53.48(18) . . . . ?