#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/45/2234550.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_2234550
loop_
_publ_author_name
'Neis, Christian'
'Merten, Günter J.'
'Hegetschweiler, Kaspar'
_publ_section_title
;
 1,3-Diammonio-1,2,3-trideoxy-cis-inositol sulfate
;
_journal_coeditor_code           BX2402
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1425
_journal_page_last               o1426
_journal_paper_doi               10.1107/S1600536812016029
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C6 H16 N2 O3 2+, S O4 2-'
_chemical_formula_moiety         'C6 H16 N2 O3, O4 S'
_chemical_formula_sum            'C6 H16 N2 O7 S'
_chemical_formula_weight         260.27
_chemical_name_systematic
;
1,3-Diammonio-1,2,3-trideoxy-cis-inositol sulfate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 101.46(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2151(18)
_cell_length_b                   6.6673(13)
_cell_length_c                   17.267(4)
_cell_measurement_reflns_used    3837
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.55
_cell_volume                     1039.7(4)
_computing_cell_refinement       'IPDS Software (Stoe & Cie, 1997)'
_computing_data_collection       'IPDS Software (Stoe & Cie, 1997)'
_computing_data_reduction        'IPDS Software (Stoe & Cie, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2011)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Stoe IPDS image plate'
_diffrn_measurement_method       'phi scans'
_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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6961
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1779
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0255
_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)+(0.0259P)²+0.7072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0642
_refine_ls_wR_factor_ref         0.0656
_reflns_number_gt                1685
_reflns_number_total             1779
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bx2402.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2234550
_cod_database_fobs_code          2234550
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'
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
C C5 0.44604(15) -0.0876(2) 0.10574(8) 0.0129(3) Uani d . 1
H H5 0.4373 -0.1399 0.0507 0.015 Uiso calc R 1
C C6 0.35712(15) -0.2238(2) 0.15088(8) 0.0149(3) Uani d . 1
H H6A 0.3961 -0.3624 0.1521 0.018 Uiso calc R 1
H H6B 0.3684 -0.1762 0.2061 0.018 Uiso calc R 1
C C2 0.12716(15) -0.0111(2) 0.10691(8) 0.0139(3) Uani d . 1
H H2 0.0241 -0.0171 0.0749 0.017 Uiso calc R 1
C C1 0.19415(15) -0.2228(2) 0.11143(8) 0.0136(3) Uani d . 1
H H1 0.1839 -0.2768 0.0566 0.016 Uiso calc R 1
C C3 0.22081(16) 0.1251(2) 0.06417(8) 0.0137(3) Uani d . 1
H H3 0.2117 0.0722 0.0092 0.016 Uiso calc R 1
C C4 0.38668(15) 0.1297(2) 0.10194(8) 0.0126(3) Uani d . 1
H H4 0.4396 0.2105 0.0674 0.015 Uiso calc R 1
N N1 0.11358(15) -0.3591(2) 0.15750(8) 0.0171(3) Uani d D 1
H H1A 0.124(2) -0.325(3) 0.2070(9) 0.026 Uiso d D 1
H H1B 0.142(2) -0.481(2) 0.1514(10) 0.026 Uiso d D 1
H H1C 0.0204(17) -0.360(3) 0.1393(10) 0.026 Uiso d D 1
N N5 0.60555(14) -0.09248(19) 0.14663(8) 0.0151(3) Uani d D 1
H H5A 0.6514(19) 0.006(3) 0.1269(10) 0.023 Uiso d D 1
H H5B 0.612(2) -0.084(3) 0.1971(9) 0.023 Uiso d D 1
H H5C 0.642(2) -0.208(2) 0.1385(10) 0.023 Uiso d D 1
O O4 0.41236(12) 0.21890(16) 0.17886(6) 0.0177(2) Uani d D 1
H H4O 0.4859(19) 0.294(3) 0.1786(11) 0.027 Uiso d D 1
O O2 0.12055(12) 0.05338(16) 0.18490(6) 0.0188(2) Uani d D 1
H H2O 0.0491(19) 0.137(3) 0.1815(11) 0.028 Uiso d D 1
O O3 0.15853(12) 0.32218(16) 0.05817(6) 0.0206(2) Uani d D 1
H H3O 0.171(2) 0.369(3) 0.0137(9) 0.031 Uiso d D 1
S S1 0.77047(4) 0.40360(5) 0.132375(19) 0.01264(13) Uani d . 1
O O7 0.80382(13) 0.58885(16) 0.09000(6) 0.0268(3) Uani d . 1
O O8 0.90424(11) 0.34825(16) 0.19086(6) 0.0201(2) Uani d . 1
O O5 0.72807(12) 0.23732(16) 0.07600(6) 0.0221(3) Uani d . 1
O O6 0.65015(12) 0.45266(18) 0.17466(7) 0.0294(3) Uani d . 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
N5 C5 C6 108.67(11)
N5 C5 C4 110.25(11)
C6 C5 C4 110.85(11)
N5 C5 H5 109.0
C6 C5 H5 109.0
C4 C5 H5 109.0
C1 C6 C5 110.43(11)
C1 C6 H6A 109.6
C5 C6 H6A 109.6
C1 C6 H6B 109.6
C5 C6 H6B 109.6
H6A C6 H6B 108.1
O2 C2 C1 108.74(11)
O2 C2 C3 114.09(11)
C1 C2 C3 107.97(11)
O2 C2 H2 108.6
C1 C2 H2 108.6
C3 C2 H2 108.6
N1 C1 C6 107.99(11)
N1 C1 C2 110.35(12)
C6 C1 C2 112.20(11)
N1 C1 H1 108.7
C6 C1 H1 108.7
C2 C1 H1 108.7
O3 C3 C4 111.27(11)
O3 C3 C2 108.78(11)
C4 C3 C2 114.41(11)
O3 C3 H3 107.4
C4 C3 H3 107.4
C2 C3 H3 107.4
O4 C4 C3 111.66(11)
O4 C4 C5 110.99(11)
C3 C4 C5 108.20(11)
O4 C4 H4 108.6
C3 C4 H4 108.6
C5 C4 H4 108.6
C1 N1 H1A 113.0(13)
C1 N1 H1B 108.2(12)
H1A N1 H1B 112.8(17)
C1 N1 H1C 112.2(13)
H1A N1 H1C 105.8(18)
H1B N1 H1C 104.5(18)
C5 N5 H5A 107.5(12)
C5 N5 H5B 109.5(12)
H5A N5 H5B 113.7(16)
C5 N5 H5C 108.8(12)
H5A N5 H5C 111.5(17)
H5B N5 H5C 105.7(17)
C4 O4 H4O 103.2(12)
C2 O2 H2O 107.9(12)
C3 O3 H3O 106.1(13)
O5 S1 O8 109.81(7)
O5 S1 O6 111.42(6)
O8 S1 O6 108.86(7)
O5 S1 O7 110.50(6)
O8 S1 O7 108.39(6)
O6 S1 O7 107.77(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C5 N5 1.4993(18)
C5 C6 1.5355(19)
C5 C4 1.5454(19)
C5 H5 1.0000
C6 C1 1.521(2)
C6 H6A 0.9900
C6 H6B 0.9900
C2 O2 1.4265(17)
C2 C1 1.536(2)
C2 C3 1.5386(19)
C2 H2 1.0000
C1 N1 1.4985(18)
C1 H1 1.0000
C3 O3 1.4297(17)
C3 C4 1.538(2)
C3 H3 1.0000
C4 O4 1.4312(17)
C4 H4 1.0000
N1 H1A 0.870(14)
N1 H1B 0.867(15)
N1 H1C 0.853(15)
N5 H5A 0.885(15)
N5 H5B 0.864(14)
N5 H5C 0.866(15)
O4 H4O 0.845(15)
O2 H2O 0.855(15)
O3 H3O 0.856(15)
S1 O5 1.4758(11)
S1 O8 1.4768(11)
S1 O6 1.4802(12)
S1 O7 1.4982(11)
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 H1A O4 2_545 0.870(14) 2.086(15) 2.9292(17) 163.0(17)
N1 H1B O3 1_545 0.867(15) 2.105(16) 2.8125(18) 138.4(16)
N1 H1C O7 1_445 0.853(15) 2.037(16) 2.882(2) 170.3(18)
N5 H5A O5 . 0.885(15) 1.974(15) 2.8538(17) 172.6(17)
N5 H5B O8 2_645 0.864(14) 2.019(15) 2.8530(18) 161.8(17)
N5 H5C O7 1_545 0.866(15) 2.290(16) 3.0852(18) 152.8(16)
N5 H5C O6 1_545 0.866(15) 2.342(16) 3.0856(19) 144.2(15)
O4 H4O O6 . 0.845(15) 1.857(15) 2.7017(16) 177.3(19)
O2 H2O O8 1_455 0.855(15) 1.970(15) 2.8161(15) 170.1(18)
O3 H3O O7 3_665 0.856(15) 1.873(15) 2.7149(16) 167.4(19)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N5 C5 C6 C1 179.85(11)
C4 C5 C6 C1 58.54(15)
C5 C6 C1 N1 179.52(11)
C5 C6 C1 C2 -58.64(15)
O2 C2 C1 N1 51.84(14)
C3 C2 C1 N1 176.11(10)
O2 C2 C1 C6 -68.64(14)
C3 C2 C1 C6 55.63(14)
O2 C2 C3 O3 -60.00(15)
C1 C2 C3 O3 179.00(10)
O2 C2 C3 C4 65.11(15)
C1 C2 C3 C4 -55.89(14)
O3 C3 C4 O4 58.04(15)
C2 C3 C4 O4 -65.75(15)
O3 C3 C4 C5 -179.54(11)
C2 C3 C4 C5 56.67(15)
N5 C5 C4 O4 -53.77(15)
C6 C5 C4 O4 66.61(14)
N5 C5 C4 C3 -176.61(11)
C6 C5 C4 C3 -56.23(15)
