############################################################################## # # # This CIF contains the data in a paper accepted for publication in # # Acta Crystallographica Section E. It conforms to the requirements of # # Notes for Authors for Acta Crystallographica Section E, and has been # # peer reviewed under the auspices of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. # # # # Software is freely available for graphical display of the structure(s) # # in this CIF. For information consult the CIF software page # # http://www.iucr.org/resources/cif/software. # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-{[Ethane-1,2-diylbis(oxy)]bis(ethane-2,1-diyl)}bis(4- methylbenzenesulfonamide) ; _chemical_name_common ? _chemical_formula_moiety 'C20 H28 N2 O6 S2' _chemical_formula_sum 'C20 H28 N2 O6 S2' _chemical_formula_iupac 'C20 H28 N2 O6 S2' _chemical_formula_weight 456.56 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.135(7) _cell_length_b 9.220(6) _cell_length_c 21.452(15) _cell_angle_alpha 90.00 _cell_angle_beta 93.680(12) _cell_angle_gamma 90.00 _cell_volume 2198(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1589 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 25.65 _cell_measurement_temperature 296(2) _exptl_crystal_description Plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.281 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9381 _exptl_absorpt_correction_T_max 0.9888 _exptl_special_details ? _diffrn_ambient_temperature 296(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5135 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0666 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 25.25 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 25 _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^ > \s(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. ; _reflns_number_total 1983 _reflns_number_gt 1558 _reflns_threshold_expression I>2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_gt 0.1390 _refine_ls_wR_factor_ref 0.1504 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.034 _refine_ls_number_reflns 1983 _refine_ls_number_parameters 140 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0846P)^2^+0.5056P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.321 _refine_diff_density_min -0.357 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)' loop_ _atom_site_type_symbol _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_symmetry_multiplicity _atom_site_disorder_assembly _atom_site_disorder_group S S1 0.51163(5) 0.03617(7) 0.64470(3) 0.0440(3) Uani d . 1 1 . . O O1 0.48265(19) -0.0655(2) 0.59612(9) 0.0590(6) Uani d . 1 1 . . O O2 0.41953(16) 0.0823(2) 0.68398(9) 0.0561(5) Uani d . 1 1 . . O O3 0.87638(18) 0.0318(2) 0.72055(10) 0.0567(6) Uani d . 1 1 . . N N1 0.6163(2) -0.0329(2) 0.69058(11) 0.0464(6) Uani d D 1 1 . . H H1 0.614(3) 0.002(3) 0.7255(9) 0.056 Uiso d D 1 1 . . C C1 0.7115(3) 0.5726(4) 0.52722(19) 0.0769(10) Uani d . 1 1 . . H H1A 0.7314 0.6430 0.5592 0.115 Uiso calc R 1 1 . . H H1B 0.6528 0.6126 0.4973 0.115 Uiso calc R 1 1 . . H H1C 0.7827 0.5473 0.5066 0.115 Uiso calc R 1 1 . . C C2 0.6609(2) 0.4389(3) 0.55625(15) 0.0518(7) Uani d . 1 1 . . C C3 0.6610(2) 0.4248(3) 0.62001(15) 0.0533(7) Uani d . 1 1 . . H H3 0.6933 0.4992 0.6452 0.064 Uiso calc R 1 1 . . C C4 0.6151(2) 0.3047(3) 0.64781(13) 0.0488(7) Uani d . 1 1 . . H H4 0.6153 0.2980 0.6911 0.059 Uiso calc R 1 1 . . C C5 0.5681(2) 0.1927(3) 0.60972(12) 0.0398(6) Uani d . 1 1 . . C C6 0.5678(2) 0.2038(3) 0.54560(13) 0.0512(7) Uani d . 1 1 . . H H6 0.5374 0.1288 0.5202 0.061 Uiso calc R 1 1 . . C C7 0.6131(3) 0.3270(3) 0.51958(14) 0.0594(8) Uani d . 1 1 . . H H7 0.6116 0.3352 0.4763 0.071 Uiso calc R 1 1 . . C C8 0.7215(3) -0.1019(3) 0.66646(15) 0.0578(8) Uani d . 1 1 . . H H8A 0.6986 -0.1426 0.6257 0.069 Uiso calc R 1 1 . . H H8B 0.7461 -0.1816 0.6939 0.069 Uiso calc R 1 1 . . C C9 0.8272(3) -0.0037(4) 0.66034(14) 0.0566(8) Uani d . 1 1 . . H H9A 0.8873 -0.0518 0.6369 0.068 Uiso calc R 1 1 . . H H9B 0.8019 0.0839 0.6381 0.068 Uiso calc R 1 1 . . C C10 0.9623(3) 0.1465(3) 0.72024(14) 0.0570(8) Uani d . 1 1 . . H H10A 0.9210 0.2387 0.7150 0.068 Uiso calc R 1 1 . . H H10B 1.0129 0.1338 0.6855 0.068 Uiso calc R 1 1 . . 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 0.0341(4) 0.0516(4) 0.0450(4) -0.0066(3) -0.0080(3) 0.0044(3) O1 0.0642(13) 0.0572(11) 0.0529(12) -0.0192(10) -0.0164(10) -0.0014(9) O2 0.0341(10) 0.0774(13) 0.0567(12) -0.0015(9) 0.0011(9) 0.0128(10) O3 0.0480(11) 0.0616(12) 0.0595(13) -0.0071(9) -0.0041(10) 0.0074(10) N1 0.0402(12) 0.0549(14) 0.0428(13) 0.0016(10) -0.0072(11) -0.0002(10) C1 0.067(2) 0.0605(18) 0.102(3) -0.0117(17) -0.004(2) 0.0204(19) C2 0.0369(14) 0.0502(15) 0.068(2) 0.0001(12) -0.0021(14) 0.0101(14) C3 0.0412(14) 0.0467(14) 0.071(2) -0.0039(12) -0.0036(14) -0.0096(14) C4 0.0417(14) 0.0558(15) 0.0478(16) -0.0024(12) -0.0043(12) -0.0049(13) C5 0.0296(12) 0.0452(13) 0.0440(14) 0.0015(10) -0.0033(11) 0.0013(11) C6 0.0518(16) 0.0545(15) 0.0463(16) -0.0087(13) -0.0055(13) -0.0009(13) C7 0.0644(19) 0.0631(18) 0.0499(17) -0.0079(15) -0.0023(15) 0.0103(14) C8 0.0500(16) 0.0562(16) 0.0658(19) 0.0092(13) -0.0086(15) -0.0111(15) C9 0.0423(15) 0.0745(19) 0.0526(18) 0.0121(14) -0.0004(14) -0.0021(15) C10 0.0504(16) 0.0494(15) 0.071(2) 0.0000(13) 0.0026(14) 0.0071(14) _geom_special_details ; All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. ; 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 S1 O1 . 1.423(2) ? S1 O2 . 1.433(2) ? S1 N1 . 1.608(2) ? S1 C5 . 1.761(3) ? O3 C9 . 1.409(3) ? O3 C10 . 1.426(3) ? N1 C8 . 1.457(4) ? N1 H1 . 0.816(17) ? C1 C2 . 1.507(4) ? C1 H1A . 0.9600 ? C1 H1B . 0.9600 ? C1 H1C . 0.9600 ? C2 C3 . 1.374(4) ? C2 C7 . 1.383(4) ? C3 C4 . 1.372(4) ? C3 H3 . 0.9300 ? C4 C5 . 1.398(4) ? C4 H4 . 0.9300 ? C5 C6 . 1.379(4) ? C6 C7 . 1.376(4) ? C6 H6 . 0.9300 ? C7 H7 . 0.9300 ? C8 C9 . 1.497(4) ? C8 H8A . 0.9700 ? C8 H8B . 0.9700 ? C9 H9A . 0.9700 ? C9 H9B . 0.9700 ? C10 C10 2_756 1.482(6) ? C10 H10A . 0.9700 ? C10 H10B . 0.9700 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 S1 O2 . . 119.26(13) ? O1 S1 N1 . . 108.00(13) ? O2 S1 N1 . . 106.01(13) ? O1 S1 C5 . . 107.33(13) ? O2 S1 C5 . . 107.22(13) ? N1 S1 C5 . . 108.68(12) ? C9 O3 C10 . . 112.9(2) ? C8 N1 S1 . . 121.6(2) ? C8 N1 H1 . . 124(2) ? S1 N1 H1 . . 110(2) ? C2 C1 H1A . . 109.5 ? C2 C1 H1B . . 109.5 ? H1A C1 H1B . . 109.5 ? C2 C1 H1C . . 109.5 ? H1A C1 H1C . . 109.5 ? H1B C1 H1C . . 109.5 ? C3 C2 C7 . . 118.2(3) ? C3 C2 C1 . . 120.8(3) ? C7 C2 C1 . . 121.0(3) ? C4 C3 C2 . . 122.2(3) ? C4 C3 H3 . . 118.9 ? C2 C3 H3 . . 118.9 ? C3 C4 C5 . . 118.6(3) ? C3 C4 H4 . . 120.7 ? C5 C4 H4 . . 120.7 ? C6 C5 C4 . . 120.3(2) ? C6 C5 S1 . . 120.5(2) ? C4 C5 S1 . . 119.1(2) ? C7 C6 C5 . . 119.2(3) ? C7 C6 H6 . . 120.4 ? C5 C6 H6 . . 120.4 ? C6 C7 C2 . . 121.5(3) ? C6 C7 H7 . . 119.2 ? C2 C7 H7 . . 119.2 ? N1 C8 C9 . . 114.9(2) ? N1 C8 H8A . . 108.5 ? C9 C8 H8A . . 108.5 ? N1 C8 H8B . . 108.5 ? C9 C8 H8B . . 108.5 ? H8A C8 H8B . . 107.5 ? O3 C9 C8 . . 108.8(2) ? O3 C9 H9A . . 109.9 ? C8 C9 H9A . . 109.9 ? O3 C9 H9B . . 109.9 ? C8 C9 H9B . . 109.9 ? H9A C9 H9B . . 108.3 ? O3 C10 C10 . 2_756 109.8(2) ? O3 C10 H10A . . 109.7 ? C10 C10 H10A 2_756 . 109.7 ? O3 C10 H10B . . 109.7 ? C10 C10 H10B 2_756 . 109.7 ? H10A C10 H10B . . 108.2 ? 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 N1 H1 O2 2_656 0.816(17) 2.135(18) 2.944(3) 171(3) C6 H6 O1 5_656 0.93 2.56 3.311(4) 138.2 _iucr_refine_instructions_details ; TITL sad in C2/c CELL 0.71073 11.1355 9.2196 21.4523 90.000 93.680 90.000 ZERR 4.00 0.0074 0.0062 0.0145 0.000 0.012 0.000 LATT 7 SYMM -X, Y, 0.5-Z SFAC C H N O S UNIT 80 112 8 24 8 SIZE 0.040 0.140 0.230 TEMP 23.000 L.S. 24 HTAB N1 O2_$1 HTAB C6 O1_$2 EQIV $1 -X+1, Y ,-Z+3/2 EQIV $2 -X+1, -Y, -Z+1 OMIT -2 50.5 OMIT 0 0 2 ACTA BOND $H DFIX 0.86 N1 H1 WGHT 0.084600 0.505600 FVAR 0.11522 S1 5 0.511632 0.036166 0.644703 11.00000 0.03408 0.05158 = 0.04501 0.00442 -0.00805 -0.00658 O1 4 0.482646 -0.065488 0.596120 11.00000 0.06419 0.05717 = 0.05294 -0.00145 -0.01640 -0.01916 O2 4 0.419531 0.082316 0.683977 11.00000 0.03406 0.07744 = 0.05670 0.01284 0.00106 -0.00149 O3 4 0.876385 0.031784 0.720548 11.00000 0.04802 0.06155 = 0.05953 0.00737 -0.00414 -0.00708 N1 3 0.616333 -0.032851 0.690580 11.00000 0.04024 0.05495 = 0.04280 -0.00015 -0.00716 0.00160 H1 2 0.614404 0.001692 0.725540 11.00000 -1.20000 C1 1 0.711531 0.572605 0.527225 11.00000 0.06727 0.06053 = 0.10160 0.02043 -0.00382 -0.01165 AFIX 137 H1A 2 0.731429 0.643023 0.559200 11.00000 -1.50000 H1B 2 0.652771 0.612642 0.497338 11.00000 -1.50000 H1C 2 0.782668 0.547332 0.506644 11.00000 -1.50000 AFIX 0 C2 1 0.660874 0.438908 0.556249 11.00000 0.03688 0.05019 = 0.06750 0.01008 -0.00208 0.00010 C3 1 0.661036 0.424843 0.620008 11.00000 0.04124 0.04673 = 0.07098 -0.00963 -0.00361 -0.00392 AFIX 43 H3 2 0.693308 0.499181 0.645150 11.00000 -1.20000 AFIX 0 C4 1 0.615145 0.304720 0.647806 11.00000 0.04170 0.05581 = 0.04782 -0.00494 -0.00435 -0.00237 AFIX 43 H4 2 0.615314 0.297989 0.691067 11.00000 -1.20000 AFIX 0 C5 1 0.568126 0.192653 0.609716 11.00000 0.02965 0.04517 = 0.04400 0.00131 -0.00325 0.00148 C6 1 0.567819 0.203751 0.545604 11.00000 0.05182 0.05447 = 0.04629 -0.00091 -0.00554 -0.00875 AFIX 43 H6 2 0.537351 0.128796 0.520245 11.00000 -1.20000 AFIX 0 C7 1 0.613112 0.327007 0.519577 11.00000 0.06442 0.06313 = 0.04993 0.01032 -0.00232 -0.00789 AFIX 43 H7 2 0.611567 0.335245 0.476326 11.00000 -1.20000 AFIX 0 C8 1 0.721494 -0.101866 0.666464 11.00000 0.04997 0.05619 = 0.06578 -0.01113 -0.00865 0.00919 AFIX 23 H8A 2 0.698570 -0.142583 0.625734 11.00000 -1.20000 H8B 2 0.746131 -0.181567 0.693900 11.00000 -1.20000 AFIX 0 C9 1 0.827193 -0.003669 0.660345 11.00000 0.04230 0.07451 = 0.05264 -0.00215 -0.00041 0.01214 AFIX 23 H9A 2 0.887280 -0.051822 0.636901 11.00000 -1.20000 H9B 2 0.801883 0.083885 0.638130 11.00000 -1.20000 AFIX 0 C10 1 0.962320 0.146465 0.720239 11.00000 0.05036 0.04938 = 0.07102 0.00711 0.00265 0.00000 AFIX 23 H10A 2 0.921010 0.238720 0.715039 11.00000 -1.20000 H10B 2 1.012938 0.133761 0.685494 11.00000 -1.20000 HKLF 4 REM sad in C2/c REM R1 = 0.0533 for 1558 Fo > 4sig(Fo) and 0.0679 for all 1983 data REM 140 parameters refined using 1 restraints END WGHT 0.0830 0.5613 REM Highest difference peak 0.321, deepest hole -0.357, 1-sigma level 0.064 Q1 1 0.4429 0.0062 0.6766 11.00000 0.05 0.32 Q2 1 0.5699 0.0856 0.6083 11.00000 0.05 0.32 Q3 1 0.6041 0.1735 0.5788 11.00000 0.05 0.28 Q4 1 0.4663 0.0636 0.6769 11.00000 0.05 0.28 ; data_global _journal_date_recd_electronic 2012-05-23 _journal_date_accepted 2012-05-28 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2012 _journal_volume 68 _journal_issue 7 _journal_page_first o1983 _journal_page_last o1983 _journal_paper_category QO _journal_paper_doi 10.1107/S1600536812024324 _journal_coeditor_code PV2551 _publ_contact_author_name 'Hamid Khaledi' _publ_contact_author_address ; Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia ; _publ_contact_author_email 'hamid.khaledi@gmail.com' _publ_contact_author_fax '603-79674193' _publ_contact_author_phone '603-79674246' _publ_section_title ;\ N,N'-{[Ethane-1,2-diylbis(oxy)]bis(ethane-2,1-diyl)}bis(4-\ methylbenzenesulfonamide) ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Al-Mohammed, Nassir N.' . ; Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia ; 'Alias, Yatimah' . ; Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia ; 'Abdullah, Zanariah' . ; Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia ; 'Khaledi, Hamid' . ; Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia ;