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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Tricyclo[3.3.1.0^3,7^]nonane-3,7-diyl bis(methanesulfonate)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H18 O6 S2'
_chemical_formula_sum     'C11 H18 O6 S2'
_chemical_formula_iupac     'C11 H18 O6 S2'
_chemical_formula_weight     310.37
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 1 21/n 1'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     8.8017(2)
_cell_length_b     10.3107(2)
_cell_length_c     14.4623(3)
_cell_angle_alpha     90.00
_cell_angle_beta     92.092(2)
_cell_angle_gamma     90.00
_cell_volume     1311.60(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4520
_cell_measurement_theta_min     3.0372
_cell_measurement_theta_max     30.1941
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.18
_exptl_crystal_size_mid     0.06
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.572
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     656
_exptl_absorpt_coefficient_mu     0.426
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(CrysAlis RED; Oxford Diffraction, 2008)'
_exptl_absorpt_correction_T_min     0.91918
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(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     'Oxford Diffraction Xcalibur-3'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     16.0288
_diffrn_reflns_number     8431
_diffrn_reflns_av_R_equivalents     0.0315
_diffrn_reflns_av_sigmaI/netI     0.0365
_diffrn_reflns_theta_min     3.04
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² 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     2308
_reflns_number_gt     1791
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0410
_refine_ls_R_factor_gt     0.0288
_refine_ls_wR_factor_gt     0.0703
_refine_ls_wR_factor_ref     0.0725
_refine_ls_goodness_of_fit_ref     1.002
_refine_ls_restrained_S_all     1.002
_refine_ls_number_reflns     2308
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0414P)²+0.0000P] where P=(Fo²+2Fc²)/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     0.308
_refine_diff_density_min     -0.336
_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'
    '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     'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_cell_refinement     'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'WinGX (Farrugia, 1999)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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_disorder_assembly
    _atom_site_disorder_group
    S S1 0.15096(6) 0.16605(5) -0.14000(3) 0.01491(14) Uani d . 1 . .
    S S2 0.58045(5) 0.26342(5) 0.01791(4) 0.01445(14) Uani d . 1 . .
    O O1 0.24294(14) 0.17383(12) -0.04474(9) 0.0127(3) Uani d . 1 . .
    O O2 -0.00837(15) 0.17596(14) -0.12494(10) 0.0203(4) Uani d . 1 . .
    O O3 0.20781(16) 0.05237(15) -0.18235(10) 0.0263(4) Uani d . 1 . .
    O O4 0.46545(14) 0.19451(13) 0.08427(9) 0.0147(3) Uani d . 1 . .
    O O5 0.50094(15) 0.33931(14) -0.05052(10) 0.0204(3) Uani d . 1 . .
    O O6 0.69589(15) 0.32558(14) 0.07372(10) 0.0213(4) Uani d . 1 . .
    C C1 0.1867(2) 0.23973(19) 0.03658(13) 0.0118(4) Uani d . 1 . .
    C C2 0.0669(2) 0.16160(19) 0.08527(13) 0.0141(5) Uani d . 1 . .
    H H2A 0.0827 0.0690 0.0784 0.017 Uiso calc R 1 . .
    H H2B -0.0351 0.1838 0.0629 0.017 Uiso calc R 1 . .
    C C3 0.0968(2) 0.2058(2) 0.18502(14) 0.0164(5) Uani d . 1 . .
    H H3 0.0386 0.1553 0.2289 0.020 Uiso calc R 1 . .
    C C4 0.0647(2) 0.3523(2) 0.19196(14) 0.0179(5) Uani d . 1 . .
    H H4A 0.0896 0.3818 0.2544 0.021 Uiso calc R 1 . .
    H H4B -0.0427 0.3681 0.1792 0.021 Uiso calc R 1 . .
    C C5 0.1586(2) 0.4297(2) 0.12291(14) 0.0157(5) Uani d . 1 . .
    H H5 0.1397 0.5231 0.1271 0.019 Uiso calc R 1 . .
    C C6 0.3291(2) 0.39729(18) 0.13632(15) 0.0154(5) Uani d . 1 . .
    H H6A 0.3908 0.4462 0.0944 0.018 Uiso calc R 1 . .
    H H6B 0.3657 0.4116 0.1996 0.018 Uiso calc R 1 . .
    C C7 0.3234(2) 0.25284(19) 0.11167(14) 0.0122(4) Uani d . 1 . .
    C C8 0.2677(2) 0.17855(19) 0.19476(14) 0.0150(4) Uani d . 1 . .
    H H8A 0.3113 0.2123 0.2524 0.018 Uiso calc R 1 . .
    H H8B 0.2896 0.0866 0.1904 0.018 Uiso calc R 1 . .
    C C9 0.1300(2) 0.37854(18) 0.02389(14) 0.0144(4) Uani d . 1 . .
    H H9A 0.0231 0.3814 0.0053 0.017 Uiso calc R 1 . .
    H H9B 0.1886 0.4258 -0.0206 0.017 Uiso calc R 1 . .
    C C10 0.2097(2) 0.3026(2) -0.20119(15) 0.0201(5) Uani d . 1 . .
    H H10A 0.1715 0.3795 -0.1728 0.030 Uiso calc R 1 . .
    H H10B 0.1711 0.2975 -0.2640 0.030 Uiso calc R 1 . .
    H H10C 0.3188 0.3057 -0.2003 0.030 Uiso calc R 1 . .
    C C11 0.6535(2) 0.1234(2) -0.03142(15) 0.0215(5) Uani d . 1 . .
    H H11A 0.7066 0.0734 0.0155 0.032 Uiso calc R 1 . .
    H H11B 0.7223 0.1469 -0.0786 0.032 Uiso calc R 1 . .
    H H11C 0.5716 0.0728 -0.0583 0.032 Uiso calc R 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 0.0177(3) 0.0144(3) 0.0126(3) -0.0015(2) 0.0004(2) -0.0005(2)
    S2 0.0119(2) 0.0140(3) 0.0175(3) -0.0014(2) 0.0012(2) 0.0022(2)
    O1 0.0132(7) 0.0129(7) 0.0119(7) 0.0017(6) 0.0005(6) -0.0006(6)
    O2 0.0142(7) 0.0285(9) 0.0179(8) -0.0048(6) -0.0022(6) 0.0026(7)
    O3 0.0400(9) 0.0201(9) 0.0186(9) 0.0031(7) 0.0002(7) -0.0068(7)
    O4 0.0105(7) 0.0148(8) 0.0189(8) 0.0027(5) 0.0025(6) 0.0048(6)
    O5 0.0169(7) 0.0199(8) 0.0242(8) -0.0022(6) -0.0016(6) 0.0095(7)
    O6 0.0167(7) 0.0224(8) 0.0247(9) -0.0059(6) -0.0014(6) -0.0005(7)
    C1 0.0141(9) 0.0114(10) 0.0098(10) 0.0018(8) -0.0004(8) -0.0024(8)
    C2 0.0112(10) 0.0135(11) 0.0177(11) -0.0001(8) 0.0015(8) -0.0008(9)
    C3 0.0149(10) 0.0177(11) 0.0167(11) -0.0009(9) 0.0035(9) 0.0029(9)
    C4 0.0187(10) 0.0205(12) 0.0144(11) 0.0037(9) 0.0013(9) -0.0051(9)
    C5 0.0182(10) 0.0114(11) 0.0173(11) 0.0027(9) -0.0025(9) -0.0015(9)
    C6 0.0174(10) 0.0136(11) 0.0151(11) -0.0028(8) -0.0019(8) -0.0010(9)
    C7 0.0086(9) 0.0127(11) 0.0154(11) 0.0027(8) 0.0006(8) 0.0000(8)
    C8 0.0182(10) 0.0144(11) 0.0125(11) -0.0003(9) 0.0004(8) 0.0016(9)
    C9 0.0157(10) 0.0107(10) 0.0165(11) 0.0028(8) -0.0022(8) 0.0010(9)
    C10 0.0234(11) 0.0223(12) 0.0146(11) -0.0026(9) 0.0015(9) 0.0054(9)
    C11 0.0222(11) 0.0187(11) 0.0242(12) -0.0004(9) 0.0068(10) 0.0008(10)
_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 O3 . 1.4219(15) ?
    S1 O2 . 1.4307(14) ?
    S1 O1 . 1.5742(14) ?
    S1 C10 . 1.751(2) ?
    S2 O5 . 1.4251(15) ?
    S2 O6 . 1.4264(14) ?
    S2 O4 . 1.5878(13) ?
    S2 C11 . 1.744(2) ?
    O1 C1 . 1.460(2) ?
    O4 C7 . 1.456(2) ?
    C1 C2 . 1.520(3) ?
    C1 C9 . 1.525(3) ?
    C1 C7 . 1.597(3) ?
    C2 C3 . 1.526(3) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C8 . 1.532(3) ?
    C3 C4 . 1.541(3) ?
    C3 H3 . 0.9800 ?
    C4 C5 . 1.542(3) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 C9 . 1.538(3) ?
    C5 C6 . 1.542(3) ?
    C5 H5 . 0.9800 ?
    C6 C7 . 1.532(3) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C8 . 1.521(3) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
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
    O3 S1 O2 . . 119.13(9) ?
    O3 S1 O1 . . 103.95(8) ?
    O2 S1 O1 . . 109.80(8) ?
    O3 S1 C10 . . 109.27(10) ?
    O2 S1 C10 . . 109.20(9) ?
    O1 S1 C10 . . 104.44(9) ?
    O5 S2 O6 . . 117.89(9) ?
    O5 S2 O4 . . 110.96(8) ?
    O6 S2 O4 . . 108.40(8) ?
    O5 S2 C11 . . 110.46(10) ?
    O6 S2 C11 . . 109.76(10) ?
    O4 S2 C11 . . 97.43(9) ?
    C1 O1 S1 . . 123.37(11) ?
    C7 O4 S2 . . 123.55(12) ?
    O1 C1 C2 . . 112.81(15) ?
    O1 C1 C9 . . 117.32(16) ?
    C2 C1 C9 . . 108.87(15) ?
    O1 C1 C7 . . 108.56(14) ?
    C2 C1 C7 . . 104.36(15) ?
    C9 C1 C7 . . 103.75(15) ?
    C1 C2 C3 . . 100.43(15) ?
    C1 C2 H2A . . 111.7 ?
    C3 C2 H2A . . 111.7 ?
    C1 C2 H2B . . 111.7 ?
    C3 C2 H2B . . 111.7 ?
    H2A C2 H2B . . 109.5 ?
    C2 C3 C8 . . 99.61(15) ?
    C2 C3 C4 . . 109.18(17) ?
    C8 C3 C4 . . 110.84(16) ?
    C2 C3 H3 . . 112.2 ?
    C8 C3 H3 . . 112.2 ?
    C4 C3 H3 . . 112.2 ?
    C3 C4 C5 . . 111.15(16) ?
    C3 C4 H4A . . 109.4 ?
    C5 C4 H4A . . 109.4 ?
    C3 C4 H4B . . 109.4 ?
    C5 C4 H4B . . 109.4 ?
    H4A C4 H4B . . 108.0 ?
    C9 C5 C4 . . 110.63(16) ?
    C9 C5 C6 . . 99.70(16) ?
    C4 C5 C6 . . 110.43(16) ?
    C9 C5 H5 . . 111.8 ?
    C4 C5 H5 . . 111.8 ?
    C6 C5 H5 . . 111.8 ?
    C7 C6 C5 . . 99.07(14) ?
    C7 C6 H6A . . 112.0 ?
    C5 C6 H6A . . 112.0 ?
    C7 C6 H6B . . 112.0 ?
    C5 C6 H6B . . 112.0 ?
    H6A C6 H6B . . 109.6 ?
    O4 C7 C8 . . 108.17(15) ?
    O4 C7 C6 . . 116.36(15) ?
    C8 C7 C6 . . 108.33(16) ?
    O4 C7 C1 . . 114.40(15) ?
    C8 C7 C1 . . 103.79(14) ?
    C6 C7 C1 . . 104.95(15) ?
    C7 C8 C3 . . 100.29(15) ?
    C7 C8 H8A . . 111.7 ?
    C3 C8 H8A . . 111.7 ?
    C7 C8 H8B . . 111.7 ?
    C3 C8 H8B . . 111.7 ?
    H8A C8 H8B . . 109.5 ?
    C1 C9 C5 . . 99.66(15) ?
    C1 C9 H9A . . 111.8 ?
    C5 C9 H9A . . 111.8 ?
    C1 C9 H9B . . 111.8 ?
    C5 C9 H9B . . 111.8 ?
    H9A C9 H9B . . 109.6 ?
    S1 C10 H10A . . 109.5 ?
    S1 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    S1 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    S2 C11 H11A . . 109.5 ?
    S2 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    S2 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
data_global
_journal_date_recd_electronic     2009-12-06
_journal_date_accepted     2010-01-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      2
_journal_page_first     o409
_journal_page_last     o409
_journal_paper_category     QO
_journal_coeditor_code     NC2172
_publ_contact_author_name
;
Manos, Manolis J.
Ioannou, Savvas
;
_publ_contact_author_address
;
Department of Chemistry
University of Cyprus
1678 Nicosia, Cyprus
;
_publ_contact_author_email
                           'emmanouil.manos@ucy.acy.cy,ioannou.savvas@ucy.ac.cy'
_publ_contact_author_fax     00357-2289-2801
_publ_contact_author_phone     00357-2289-2770
_publ_section_title
;
Tricyclo[3.3.1.0^3,7^]nonane-3,7-diyl bis(methanesulfonate)
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Ioannou, Savvas' .
;
Department of Chemistry
University of Cyprus
1678 Nicosia, Cyprus
;
    'Nicolaides, Athanassios V.' .
;
Department of Chemistry
University of Cyprus
1678 Nicosia, Cyprus
;
    'Manos, Manolis J.' .
;
Department of Chemistry
University of Cyprus
1678 Nicosia, Cyprus
;
