##############################################################################
# #
# 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
;