##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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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#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
[1-(1-Adamantylamino)ethylidene]oxonium methanesulfonate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H20 N O +, C H3 O3 S -'
_chemical_formula_sum     'C13 H23 N O4 S'
_chemical_formula_iupac     'C12 H20 N O +, C H3 S O3 -'
_chemical_formula_weight     289.38
_chemical_melting_point     445
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     12.9848(7)
_cell_length_b     11.2625(6)
_cell_length_c     19.0037(10)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2779.1(3)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     2454
_cell_measurement_theta_min     3.14
_cell_measurement_theta_max     25.00
_cell_measurement_temperature     120(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.35
_exptl_crystal_density_diffrn     1.383
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1248
_exptl_absorpt_coefficient_mu     0.243
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(Xcalibur; Oxford Diffraction, 2006)'
_exptl_absorpt_correction_T_min     0.824
_exptl_absorpt_correction_T_max     0.914
_exptl_special_details
;
;
_diffrn_ambient_temperature     120(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     'Kuma KM-4 CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     0.06
_diffrn_reflns_number     19453
_diffrn_reflns_av_R_equivalents     0.0166
_diffrn_reflns_av_sigmaI/netI     0.0113
_diffrn_reflns_theta_min     3.14
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_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 >
2σ(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     2454
_reflns_number_gt     2000
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0454
_refine_ls_R_factor_gt     0.0337
_refine_ls_wR_factor_gt     0.0913
_refine_ls_wR_factor_ref     0.1017
_refine_ls_goodness_of_fit_ref     1.093
_refine_ls_restrained_S_all     1.093
_refine_ls_number_reflns     2454
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
           'calc w=1/[σ²(Fo²)+(0.054P)²+1.529P] 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     0.303
_refine_diff_density_min     -0.470
_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     'Xcalibur (Oxford Diffraction, 2006)'
_computing_cell_refinement     'Xcalibur (Oxford Diffraction, 2006)'
_computing_data_reduction     'Xcalibur (Oxford Diffraction, 2006)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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
    C C1 -0.09044(13) 0.28700(14) 0.34406(9) 0.0181(4) Uani d . 1 . .
    C C2 -0.00380(13) 0.22857(15) 0.30176(9) 0.0195(4) Uani d . 1 . .
    H H2A 0.0621 0.2698 0.3111 0.023 Uiso calc R 1 . .
    H H2B 0.0038 0.1445 0.3162 0.023 Uiso calc R 1 . .
    C C3 -0.10319(14) 0.41701(15) 0.32215(9) 0.0201(4) Uani d . 1 . .
    H H3A -0.1594 0.4541 0.3496 0.024 Uiso calc R 1 . .
    H H3B -0.0388 0.4613 0.3317 0.024 Uiso calc R 1 . .
    C C4 -0.19133(14) 0.22087(16) 0.33012(9) 0.0229(4) Uani d . 1 . .
    H H4A -0.1846 0.1370 0.3451 0.027 Uiso calc R 1 . .
    H H4B -0.2477 0.2576 0.3576 0.027 Uiso calc R 1 . .
    C C5 -0.21663(15) 0.22635(17) 0.25177(10) 0.0251(4) Uani d . 1 . .
    H H5 -0.2824 0.1828 0.2427 0.030 Uiso calc R 1 . .
    C C6 -0.13002(15) 0.16913(16) 0.20928(10) 0.0262(4) Uani d . 1 . .
    H H6A -0.1467 0.1724 0.1585 0.031 Uiso calc R 1 . .
    H H6B -0.1225 0.0847 0.2230 0.031 Uiso calc R 1 . .
    C C7 -0.02922(14) 0.23530(16) 0.22322(10) 0.0225(4) Uani d . 1 . .
    H H7 0.0276 0.1979 0.1954 0.027 Uiso calc R 1 . .
    C C8 -0.04113(14) 0.36523(15) 0.20149(9) 0.0224(4) Uani d . 1 . .
    H H8A -0.0567 0.3702 0.1506 0.027 Uiso calc R 1 . .
    H H8B 0.0240 0.4084 0.2103 0.027 Uiso calc R 1 . .
    C C9 -0.12838(13) 0.42199(15) 0.24371(9) 0.0213(4) Uani d . 1 . .
    H H9 -0.1362 0.5068 0.2291 0.026 Uiso calc R 1 . .
    C C10 -0.22900(14) 0.35595(17) 0.22953(10) 0.0256(4) Uani d . 1 . .
    H H10A -0.2461 0.3603 0.1788 0.031 Uiso calc R 1 . .
    H H10B -0.2858 0.3932 0.2564 0.031 Uiso calc R 1 . .
    C C11 0.00322(13) 0.32640(15) 0.45588(9) 0.0211(4) Uani d . 1 . .
    C C12 0.01287(15) 0.30548(18) 0.53284(10) 0.0271(4) Uani d . 1 . .
    H H12A 0.0762 0.2609 0.5424 0.041 Uiso calc R 1 . .
    H H12B -0.0467 0.2599 0.5495 0.041 Uiso calc R 1 . .
    H H12C 0.0155 0.3819 0.5575 0.041 Uiso calc R 1 . .
    N N1 -0.06903(11) 0.27539(13) 0.42026(8) 0.0195(3) Uani d . 1 . .
    H H1 -0.1102(15) 0.2308(18) 0.4446(11) 0.023 Uiso d . 1 . .
    O O1 0.06855(10) 0.39456(12) 0.42407(6) 0.0268(3) Uani d . 1 . .
    H H2 0.1158(17) 0.436(2) 0.4560(12) 0.040 Uiso d . 1 . .
    S S1 0.29158(4) 0.49446(4) 0.50332(2) 0.02087(16) Uani d . 1 . .
    O O2 0.17962(12) 0.51334(12) 0.50208(7) 0.0302(3) Uani d . 1 . .
    O O3 0.31512(12) 0.37147(12) 0.48779(7) 0.0342(4) Uani d . 1 . .
    O O4 0.33796(11) 0.54034(13) 0.56618(7) 0.0357(4) Uani d . 1 . .
    C C13 0.33885(17) 0.57840(19) 0.43323(10) 0.0356(5) Uani d . 1 . .
    H H13A 0.3191 0.6617 0.4396 0.053 Uiso calc R 1 . .
    H H13B 0.3099 0.5485 0.3890 0.053 Uiso calc R 1 . .
    H H13C 0.4141 0.5721 0.4318 0.053 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
    C1 0.0179(9) 0.0183(8) 0.0179(9) 0.0002(7) 0.0006(7) 0.0014(7)
    C2 0.0182(9) 0.0204(9) 0.0201(9) 0.0034(7) -0.0005(7) -0.0017(7)
    C3 0.0235(9) 0.0163(8) 0.0206(9) 0.0009(7) 0.0028(7) -0.0011(7)
    C4 0.0213(9) 0.0212(9) 0.0261(10) -0.0034(7) -0.0001(7) 0.0048(7)
    C5 0.0213(9) 0.0250(10) 0.0289(10) -0.0074(8) -0.0056(7) 0.0029(8)
    C6 0.0341(11) 0.0185(9) 0.0259(10) -0.0019(8) -0.0061(8) -0.0019(7)
    C7 0.0250(9) 0.0230(9) 0.0195(9) 0.0043(8) -0.0002(7) -0.0037(7)
    C8 0.0238(9) 0.0260(9) 0.0176(9) -0.0027(8) -0.0004(7) 0.0002(7)
    C9 0.0254(9) 0.0150(8) 0.0236(9) 0.0005(7) -0.0008(7) 0.0027(7)
    C10 0.0209(9) 0.0281(10) 0.0277(10) 0.0022(8) -0.0044(8) 0.0042(8)
    C11 0.0207(9) 0.0209(9) 0.0216(9) 0.0041(7) 0.0029(7) -0.0015(7)
    C12 0.0311(11) 0.0299(10) 0.0202(10) 0.0010(8) -0.0021(8) 0.0001(8)
    N1 0.0214(8) 0.0187(7) 0.0183(8) -0.0001(6) 0.0022(6) 0.0015(6)
    O1 0.0257(7) 0.0330(7) 0.0216(7) -0.0080(6) -0.0009(5) -0.0008(6)
    S1 0.0221(3) 0.0229(3) 0.0175(3) -0.00163(17) -0.00125(16) 0.00108(17)
    O2 0.0240(7) 0.0328(8) 0.0337(8) -0.0003(6) 0.0006(5) -0.0114(6)
    O3 0.0433(9) 0.0270(8) 0.0323(8) 0.0092(6) -0.0058(6) 0.0028(6)
    O4 0.0406(8) 0.0440(8) 0.0226(7) -0.0109(7) -0.0093(6) 0.0014(6)
    C13 0.0489(13) 0.0353(11) 0.0227(10) -0.0117(10) 0.0030(9) 0.0021(8)
_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
    C1 N1 . 1.480(2) ?
    C1 C4 . 1.530(2) ?
    C1 C3 . 1.531(2) ?
    C1 C2 . 1.531(2) ?
    C2 C7 . 1.530(3) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 C9 . 1.527(2) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C5 . 1.526(3) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 C6 . 1.527(3) ?
    C5 C10 . 1.528(2) ?
    C5 H5 . 1.0000 ?
    C6 C7 . 1.529(3) ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 C8 . 1.528(2) ?
    C7 H7 . 1.0000 ?
    C8 C9 . 1.528(2) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 C10 . 1.527(2) ?
    C9 H9 . 1.0000 ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 N1 . 1.292(2) ?
    C11 O1 . 1.294(2) ?
    C11 C12 . 1.487(3) ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    N1 H1 . 0.87(2) ?
    O1 H2 . 0.98(2) ?
    S1 O4 . 1.4343(14) ?
    S1 O3 . 1.4489(14) ?
    S1 O2 . 1.4695(15) ?
    S1 C13 . 1.7448(19) ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
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
    N1 C1 C4 . . 106.69(13) ?
    N1 C1 C3 . . 111.76(14) ?
    C4 C1 C3 . . 109.01(14) ?
    N1 C1 C2 . . 109.73(14) ?
    C4 C1 C2 . . 109.20(14) ?
    C3 C1 C2 . . 110.34(14) ?
    C7 C2 C1 . . 109.40(14) ?
    C7 C2 H2A . . 109.8 ?
    C1 C2 H2A . . 109.8 ?
    C7 C2 H2B . . 109.8 ?
    C1 C2 H2B . . 109.8 ?
    H2A C2 H2B . . 108.2 ?
    C9 C3 C1 . . 108.89(14) ?
    C9 C3 H3A . . 109.9 ?
    C1 C3 H3A . . 109.9 ?
    C9 C3 H3B . . 109.9 ?
    C1 C3 H3B . . 109.9 ?
    H3A C3 H3B . . 108.3 ?
    C5 C4 C1 . . 109.48(14) ?
    C5 C4 H4A . . 109.8 ?
    C1 C4 H4A . . 109.8 ?
    C5 C4 H4B . . 109.8 ?
    C1 C4 H4B . . 109.8 ?
    H4A C4 H4B . . 108.2 ?
    C4 C5 C6 . . 109.89(15) ?
    C4 C5 C10 . . 109.34(15) ?
    C6 C5 C10 . . 109.53(15) ?
    C4 C5 H5 . . 109.4 ?
    C6 C5 H5 . . 109.4 ?
    C10 C5 H5 . . 109.4 ?
    C5 C6 C7 . . 109.45(14) ?
    C5 C6 H6A . . 109.8 ?
    C7 C6 H6A . . 109.8 ?
    C5 C6 H6B . . 109.8 ?
    C7 C6 H6B . . 109.8 ?
    H6A C6 H6B . . 108.2 ?
    C8 C7 C6 . . 109.47(15) ?
    C8 C7 C2 . . 109.44(14) ?
    C6 C7 C2 . . 109.23(15) ?
    C8 C7 H7 . . 109.6 ?
    C6 C7 H7 . . 109.6 ?
    C2 C7 H7 . . 109.6 ?
    C7 C8 C9 . . 109.49(14) ?
    C7 C8 H8A . . 109.8 ?
    C9 C8 H8A . . 109.8 ?
    C7 C8 H8B . . 109.8 ?
    C9 C8 H8B . . 109.8 ?
    H8A C8 H8B . . 108.2 ?
    C3 C9 C10 . . 109.73(14) ?
    C3 C9 C8 . . 109.77(14) ?
    C10 C9 C8 . . 109.74(14) ?
    C3 C9 H9 . . 109.2 ?
    C10 C9 H9 . . 109.2 ?
    C8 C9 H9 . . 109.2 ?
    C9 C10 C5 . . 109.05(14) ?
    C9 C10 H10A . . 109.9 ?
    C5 C10 H10A . . 109.9 ?
    C9 C10 H10B . . 109.9 ?
    C5 C10 H10B . . 109.9 ?
    H10A C10 H10B . . 108.3 ?
    N1 C11 O1 . . 119.67(16) ?
    N1 C11 C12 . . 120.42(16) ?
    O1 C11 C12 . . 119.90(16) ?
    C11 C12 H12A . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C11 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C11 N1 C1 . . 127.58(15) ?
    C11 N1 H1 . . 115.2(14) ?
    C1 N1 H1 . . 117.2(14) ?
    C11 O1 H2 . . 113.8(13) ?
    O4 S1 O3 . . 115.18(9) ?
    O4 S1 O2 . . 112.12(8) ?
    O3 S1 O2 . . 110.11(8) ?
    O4 S1 C13 . . 107.03(9) ?
    O3 S1 C13 . . 106.76(9) ?
    O2 S1 C13 . . 104.92(10) ?
    S1 C13 H13A . . 109.5 ?
    S1 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    S1 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
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 O3 4_456 0.87(2) 1.98(2) 2.838(2) 170.1(19)
    O1 H2 O2 . 0.98(2) 1.49(2) 2.4632(18) 173(2)
data_global
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-05-04
_journal_date_accepted     2009-05-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      6
_journal_page_first     o1307
_journal_page_last     o1307
_journal_paper_category     QO
_journal_coeditor_code     PK2161
_publ_contact_author_name     'Vícha Robert'
_publ_contact_author_address
;
 Department of Chemistry
 Faculty of Technology
 Tomas Bata University in Zlin
 Nam. T. G. Masaryka 275
 Zlin,762 72, Czech Republic.
;
_publ_contact_author_email     rvicha@ft.utb.cz
_publ_contact_author_fax     '+420 576 031 560'
_publ_contact_author_phone     '+420 576 031 103 '
_publ_section_title
;
[1-(1-Adamantylamino)ethylidene]oxonium methanesulfonate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Vícha, Robert' .
;
Department of Chemistry
Faculty of Technology
Tomas Bata University in Zlin
Nám. T. G. Masaryka 275
Zlín,762 72, Czech Republic
;
    'Nečas, Marek' .
;
Department of Chemistry
Faculty of Science
Masaryk University in Brno
Kamenice 5
Brno-Bohunice, 625 00, Czech Republic
;
    'Kozubková, Zuzana' .
;
Department of Chemistry
Faculty of Technology
Tomas Bata University in Zlin
Nám. T. G. Masaryka 275
Zlín,762 72, Czech Republic
;
    'Potáček, Milan' .
;
Department of Chemistry
Faculty of Science
Masaryk University in Brno
Kamenice 5
Brno-Bohunice, 625 00, Czech Republic
;
