# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_new _database_code_depnum_ccdc_archive 'CCDC 856377' #TrackingRef 'archive.cif' _audit_creation_date 2010-04-20T08:45:16-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C15 H24 O9 S3' _chemical_formula_sum 'C15 H24 O9 S3' _chemical_formula_weight 444.52 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' _symmetry_Int_Tables_number 62 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 18.9143(7) _cell_length_b 21.0884(9) _cell_length_c 5.2773(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2104.97(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5393 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.394 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.9078 _exptl_absorpt_correction_T_max 0.9691 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.71045E-1 _diffrn_orient_matrix_ub_12 -0.323119E-1 _diffrn_orient_matrix_ub_13 -0.120158E-1 _diffrn_orient_matrix_ub_21 -0.42557E-2 _diffrn_orient_matrix_ub_22 0.226888E-1 _diffrn_orient_matrix_ub_23 -0.42778E-1 _diffrn_orient_matrix_ub_31 0.625395E-1 _diffrn_orient_matrix_ub_32 -0.351625E-1 _diffrn_orient_matrix_ub_33 -0.16561E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.074 _diffrn_reflns_av_unetI/netI 0.0446 _diffrn_reflns_number 37229 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 25.49 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.982 _reflns_number_total 1983 _reflns_number_gt 1099 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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. Both DMSO molecules are disordered, with all atoms in one molecule, except for the sulfur, which sits on a mirror plane, occupying semi-populated sites. In the other DMSO, one of the methyl groups occupies two semi-populated sites, thereby avoiding a clash with its symmetry generated neighbour. The mirror also bisects the trimesic acid but in this case only one carboxylate hydrogen atom is disordered. ; _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^)+(0.0400P)^2^+12.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1983 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1439 _refine_ls_R_factor_gt 0.088 _refine_ls_wR_factor_ref 0.2067 _refine_ls_wR_factor_gt 0.176 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.611 _refine_diff_density_min -0.698 _refine_diff_density_rms 0.097 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 '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' H H 0 0 '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 C1 C 0.5400(3) 0.6930(2) 0.5086(10) 0.0415(12) Uani 1 1 d . . . C2 C 0.4927(3) 0.6932(3) 0.7110(11) 0.0507(14) Uani 1 1 d . . . H2 H 0.4766 0.6542 0.7805 0.061 Uiso 1 1 calc R . . C3 C 0.4690(4) 0.75 0.8109(14) 0.0476(19) Uani 1 2 d S . . C4 C 0.5635(4) 0.75 0.4080(15) 0.0438(18) Uani 1 2 d S . . H4 H 0.5957 0.75 0.2699 0.053 Uiso 1 2 calc SR . . C5 C 0.5650(3) 0.6310(3) 0.4090(11) 0.0539(15) Uani 1 1 d . . . C6 C 0.4196(4) 0.75 1.0285(16) 0.067(3) Uani 1 2 d S . . C7 C 0.6422(4) 0.4586(3) -0.2994(12) 0.081(2) Uani 1 1 d . . . H7A H 0.6032 0.482 -0.3784 0.121 Uiso 1 1 calc R . . H7B H 0.6366 0.4132 -0.3334 0.121 Uiso 1 1 calc R . . H7C H 0.6872 0.4733 -0.3698 0.121 Uiso 1 1 calc R . . C8A C 0.5401(6) 0.4798(5) -0.006(2) 0.061(3) Uani 0.5 1 d P . . H8A1 H 0.5193 0.4887 0.1599 0.092 Uiso 0.5 1 calc PR . . H8A2 H 0.5204 0.4401 -0.073 0.092 Uiso 0.5 1 calc PR . . H8A3 H 0.5292 0.5146 -0.123 0.092 Uiso 0.5 1 calc PR . . C8B C 0.7202(5) 0.4198(5) 0.064(2) 0.051(3) Uani 0.5 1 d P . . H8B1 H 0.7338 0.418 0.2432 0.077 Uiso 0.5 1 calc PR . . H8B2 H 0.7595 0.4371 -0.0355 0.077 Uiso 0.5 1 calc PR . . H8B3 H 0.7091 0.377 0.004 0.077 Uiso 0.5 1 calc PR . . C9 C 0.1907(5) 0.7318(5) 1.665(2) 0.054(3) Uiso 0.5 1 d P . . H9A H 0.1502 0.7593 1.6295 0.081 Uiso 0.5 1 calc PR . . H9B H 0.2061 0.7382 1.8407 0.081 Uiso 0.5 1 calc PR . . H9C H 0.177 0.6874 1.6409 0.081 Uiso 0.5 1 calc PR . . C10 C 0.2811(7) 0.6731(6) 1.633(3) 0.070(4) Uani 0.5 1 d P . . H10A H 0.2386 0.6553 1.712 0.105 Uiso 0.5 1 calc PR . . H10B H 0.3167 0.6814 1.764 0.105 Uiso 0.5 1 calc PR . . H10C H 0.3001 0.6427 1.51 0.105 Uiso 0.5 1 calc PR . . O1 O 0.6128(2) 0.63722(18) 0.2248(9) 0.0654(12) Uani 1 1 d . . . H1 H 0.6271 0.6012 0.1803 0.098 Uiso 1 1 calc R . . O2 O 0.5433(3) 0.58059(19) 0.4833(8) 0.0736(14) Uani 1 1 d . . . O3 O 0.3994(2) 0.8032(2) 1.1173(8) 0.0638(12) Uani 1 1 d . . . H3 H 0.38 0.7975 1.2588 0.096 Uiso 0.5 1 calc PR . . O4 O 0.6736(2) 0.53680(18) 0.0618(9) 0.0717(13) Uani 1 1 d . . . O5 O 0.3194(4) 0.7881(4) 1.5059(15) 0.058(2) Uani 0.5 1 d P . . S1 S 0.64126(10) 0.47158(7) 0.0269(3) 0.0653(5) Uani 1 1 d . . . S2 S 0.25793(12) 0.75 1.4655(5) 0.0688(7) Uani 1 2 d S . . 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 C1 0.045(3) 0.038(3) 0.041(3) -0.002(2) -0.002(2) -0.001(2) C2 0.048(3) 0.058(3) 0.046(3) 0.003(3) -0.005(3) -0.010(3) C3 0.039(4) 0.065(5) 0.039(4) 0 -0.008(3) 0 C4 0.042(4) 0.046(4) 0.044(5) 0 0.000(3) 0 C5 0.069(4) 0.046(3) 0.047(4) -0.002(3) -0.004(3) -0.006(3) C6 0.044(5) 0.123(9) 0.034(5) 0 -0.008(4) 0 C7 0.113(6) 0.077(5) 0.052(4) 0.001(3) 0.014(4) -0.005(4) C8A 0.075(8) 0.056(7) 0.054(8) -0.003(6) -0.005(7) -0.024(6) C8B 0.042(6) 0.037(6) 0.075(8) -0.004(5) -0.002(6) 0.003(5) C10 0.086(9) 0.060(8) 0.064(9) 0.005(7) -0.007(7) -0.013(7) O1 0.077(3) 0.042(2) 0.077(3) -0.008(2) 0.020(2) 0.000(2) O2 0.122(4) 0.044(2) 0.055(3) -0.002(2) 0.006(3) -0.024(2) O3 0.054(2) 0.090(3) 0.047(3) -0.005(2) 0.004(2) -0.002(2) O4 0.090(3) 0.047(2) 0.078(3) -0.012(2) -0.009(3) 0.017(2) O5 0.058(5) 0.061(5) 0.055(5) -0.006(4) 0.004(4) -0.010(4) S1 0.0930(13) 0.0487(9) 0.0542(10) 0.0005(7) 0.0065(9) 0.0167(8) S2 0.0531(13) 0.107(2) 0.0467(13) 0 0.0014(10) 0 #----------------------------------------------------------------------------# # 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 C1 C4 1.387(6) . ? C1 C2 1.394(7) . ? C1 C5 1.485(7) . ? C2 C3 1.383(7) . ? C3 C2 1.383(7) 8_575 ? C3 C6 1.480(11) . ? C4 C1 1.387(6) 8_575 ? C5 O2 1.205(6) . ? C5 O1 1.334(7) . ? C6 O3 1.274(5) 8_575 ? C6 O3 1.274(5) . ? C7 S1 1.743(7) . ? C8A S1 1.930(11) . ? C8B S1 1.861(10) . ? C9 S2 1.695(10) . ? C10 S2 1.900(13) . ? O4 S1 1.517(4) . ? O5 C10 1.284(14) 8_575 ? O5 S2 1.429(8) . ? O5 O5 1.606(15) 8_575 ? S2 O5 1.429(8) 8_575 ? S2 C9 1.695(10) 8_575 ? S2 C10 1.900(13) 8_575 ? 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 C4 C1 C2 119.7(5) . . ? C4 C1 C5 121.7(5) . . ? C2 C1 C5 118.6(5) . . ? C3 C2 C1 120.2(5) . . ? C2 C3 C2 120.0(7) . 8_575 ? C2 C3 C6 120.0(4) . . ? C2 C3 C6 120.0(4) 8_575 . ? C1 C4 C1 120.2(7) . 8_575 ? O2 C5 O1 123.6(5) . . ? O2 C5 C1 123.6(6) . . ? O1 C5 C1 112.8(5) . . ? O3 C6 O3 123.3(8) 8_575 . ? O3 C6 C3 118.4(4) 8_575 . ? O3 C6 C3 118.4(4) . . ? C10 O5 S2 88.7(8) 8_575 . ? C10 O5 O5 129.7(7) 8_575 8_575 ? S2 O5 O5 55.8(3) . 8_575 ? O4 S1 C7 105.0(3) . . ? O4 S1 C8B 101.3(4) . . ? C7 S1 C8B 90.2(5) . . ? O4 S1 C8A 109.3(4) . . ? C7 S1 C8A 86.2(5) . . ? C8B S1 C8A 149.1(5) . . ? O5 S2 O5 68.4(7) . 8_575 ? O5 S2 C9 130.2(5) . . ? O5 S2 C9 113.0(5) 8_575 . ? O5 S2 C9 113.0(5) . 8_575 ? O5 S2 C9 130.2(5) 8_575 8_575 ? C9 S2 C9 26.2(7) . 8_575 ? O5 S2 C10 102.9(5) . . ? O5 S2 C10 42.5(5) 8_575 . ? C9 S2 C10 71.9(6) . . ? C9 S2 C10 94.4(6) 8_575 . ? O5 S2 C10 42.5(5) . 8_575 ? O5 S2 C10 102.9(5) 8_575 8_575 ? C9 S2 C10 94.4(6) . 8_575 ? C9 S2 C10 71.9(6) 8_575 8_575 ? C10 S2 C10 117.3(8) . 8_575 ? # END of CIF