#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/21/2222117.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222117
loop_
_publ_author_name
'Vícha, Robert'
'Nečas, Marek'
'Kozubková, Zuzana'
'Potáček, Milan'
_publ_section_title
;
 [1-(1-Adamantylamino)ethylidene]oxonium methanesulfonate
;
_journal_coeditor_code           PK2161
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1307
_journal_paper_doi               10.1107/S1600536809017632
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H20 N O +, C H3 S O3 -'
_chemical_formula_moiety         'C12 H20 N O +, C H3 O3 S -'
_chemical_formula_sum            'C13 H23 N O4 S'
_chemical_formula_weight         289.38
_chemical_melting_point          445
_chemical_name_systematic
;
[1-(1-Adamantylamino)ethylidene]oxonium methanesulfonate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.9848(7)
_cell_length_b                   11.2625(6)
_cell_length_c                   19.0037(10)
_cell_measurement_reflns_used    2454
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.14
_cell_volume                     2779.1(3)
_computing_cell_refinement       'Xcalibur (Oxford Diffraction, 2006)'
_computing_data_collection       'Xcalibur (Oxford Diffraction, 2006)'
_computing_data_reduction        'Xcalibur (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 0.06
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Kuma KM-4 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0113
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19453
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.14
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Xcalibur; Oxford Diffraction, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.470
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2454
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.054P)²+1.529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                2000
_reflns_number_total             2454
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2161.cif
_cod_data_source_block           I
_cod_database_code               2222117
_cod_database_fobs_code          2222117
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'
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_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'
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_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_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)
