#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008445.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_2008445
loop_
_publ_author_name
'Moers, O.'
'Wijaya, K.'
'Jones, P. G.'
'Blaschette, A.'
_publ_section_title
;
 Polysulfonylamines. CIX. 1,2,4-Triazolium di(methanesulfonyl)amidate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              754
_journal_page_last               756
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C2 H4 N3 +, C2 H6 N O4 S2 -'
_chemical_formula_sum            'C4 H10 N4 O4 S2'
_chemical_formula_weight         242.28
_chemical_name_systematic
;
 1,2,4-Triazolium Di(methanesulfonyl)amidate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3239(14)
_cell_length_b                   9.8199(14)
_cell_length_c                   13.738(3)
_cell_measurement_reflns_used    54
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      10
_cell_volume                     988.0(3)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe, 1992a)'
_computing_data_reduction        'REDU4 (Stoe 1992b)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Stoe STADI4'
_diffrn_measurement_method       \w/\q-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  0.0118
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3800
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         3.47
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.190
_refine_ls_abs_structure_details 'Flack  (1983)'
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_extinction_coef       0.0107(11)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2248
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0199
_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/[\s^2^(Fo^2^)+(0.0375P)^2^+0.0744P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0549
_reflns_number_gt                2209
_reflns_number_total             2248
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bm1307.cif
_[local]_cod_data_source_block   gatas
_cod_database_code               2008445
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'
loop_
_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_type_symbol
N1 0.48965(18) 0.51212(13) 0.68077(9) 0.0197(3) Uani d . 1 N
S1 0.70079(5) 0.48966(4) 0.70798(3) 0.01864(9) Uani d . 1 S
O1 0.70152(18) 0.44923(13) 0.80899(9) 0.0305(3) Uani d . 1 O
O2 0.79162(16) 0.39867(13) 0.64136(10) 0.0318(3) Uani d . 1 O
C1 0.8083(2) 0.64929(15) 0.70074(13) 0.0277(3) Uani d . 1 C
H1A 0.7883 0.6883 0.6359 0.033 Uiso calc R 1 H
H1B 0.9395 0.6384 0.7121 0.033 Uiso calc R 1 H
H1C 0.7568 0.7102 0.7501 0.033 Uiso calc R 1 H
S2 0.42393(4) 0.53396(3) 0.57093(3) 0.01726(9) Uani d . 1 S
O3 0.23331(14) 0.57005(12) 0.57682(10) 0.0281(3) Uani d . 1 O
O4 0.54007(15) 0.62912(11) 0.51883(8) 0.0230(2) Uani d . 1 O
C2 0.4382(2) 0.37634(16) 0.51052(12) 0.0243(3) Uani d . 1 C
H2A 0.3888 0.3855 0.4446 0.029 Uiso calc R 1 H
H2B 0.3677 0.3080 0.5464 0.029 Uiso calc R 1 H
H2C 0.5662 0.3477 0.5069 0.029 Uiso calc R 1 H
N2 0.2311(2) 0.46935(15) 0.82344(11) 0.0235(3) Uani d . 1 N
H01 0.287(3) 0.478(2) 0.7791(19) 0.034(6) Uiso d . 1 H
C4 0.0605(2) 0.5163(2) 0.94079(15) 0.0284(4) Uani d . 1 C
H4 0.000(3) 0.560(2) 0.9929(18) 0.035(6) Uiso d . 1 H
N3 0.06427(18) 0.37961(17) 0.93148(11) 0.0278(3) Uani d . 1 N
H02 0.005(3) 0.324(2) 0.9740(18) 0.047(6) Uiso d . 1 H
C3 0.1736(2) 0.35276(18) 0.85749(14) 0.0293(3) Uani d . 1 C
H3 0.203(3) 0.278(2) 0.8375(18) 0.039(6) Uiso d . 1 H
N4 0.16105(19) 0.57510(14) 0.87568(11) 0.0256(3) Uani d . 1 N
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
N1 0.0193(6) 0.0239(6) 0.0158(6) -0.0013(5) 0.0009(4) -0.0007(5)
S1 0.02064(17) 0.01683(16) 0.01845(17) 0.00041(12) -0.00195(15) 0.00315(13)
O1 0.0397(7) 0.0301(6) 0.0216(6) -0.0041(5) -0.0071(5) 0.0076(5)
O2 0.0284(6) 0.0316(6) 0.0354(7) 0.0086(5) -0.0012(5) -0.0066(6)
C1 0.0273(7) 0.0221(7) 0.0337(9) -0.0070(5) -0.0069(7) 0.0061(7)
S2 0.01817(16) 0.01663(16) 0.01697(15) 0.00007(12) -0.00185(14) -0.00095(13)
O3 0.0204(5) 0.0322(6) 0.0317(6) 0.0034(5) -0.0041(5) -0.0074(6)
O4 0.0274(6) 0.0201(5) 0.0214(5) -0.0033(4) -0.0035(4) 0.0046(4)
C2 0.0311(8) 0.0180(7) 0.0238(7) -0.0018(6) -0.0007(6) -0.0046(6)
N2 0.0222(6) 0.0293(7) 0.0191(7) -0.0002(5) 0.0033(5) 0.0019(6)
C4 0.0211(8) 0.0403(10) 0.0238(8) -0.0014(7) 0.0025(6) -0.0012(7)
N3 0.0238(6) 0.0347(8) 0.0250(6) -0.0105(6) -0.0045(5) 0.0110(6)
C3 0.0305(8) 0.0220(8) 0.0354(9) 0.0002(6) -0.0100(7) -0.0005(7)
N4 0.0242(6) 0.0246(6) 0.0280(7) -0.0006(6) 0.0021(5) -0.0007(6)
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
_geom_angle_publ_flag
S2 N1 S1 121.87(8) ?
O2 S1 O1 115.98(8) ?
O2 S1 N1 112.44(7) ?
O1 S1 N1 105.37(7) ?
O2 S1 C1 108.08(8) ?
O1 S1 C1 107.35(8) ?
N1 S1 C1 107.20(7) ?
O3 S2 O4 115.87(7) ?
O3 S2 N1 105.75(8) ?
O4 S2 N1 112.04(7) ?
O3 S2 C2 107.47(7) ?
O4 S2 C2 107.38(7) ?
N1 S2 C2 108.02(7) ?
C3 N2 N4 110.99(15) y
N4 C4 N3 111.53(17) y
C3 N3 C4 106.50(15) y
N2 C3 N3 107.22(17) y
C4 N4 N2 103.76(14) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 S2 1.5984(14) ?
N1 S1 1.6061(14) ?
S1 O2 1.4416(13) ?
S1 O1 1.4434(13) ?
S1 C1 1.7568(15) ?
S2 O3 1.4426(11) ?
S2 O4 1.4522(11) ?
S2 C2 1.7594(16) ?
N2 C3 1.306(2) y
N2 N4 1.362(2) y
C4 N4 1.294(2) y
C4 N3 1.349(2) y
N3 C3 1.321(3) y
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
_geom_hbond_publ_flag
N2 H01 N1 . 0.74(3) 2.04(3) 2.7576(19) 166(3) y
N3 H02 O3 2_565 0.91(3) 2.47(2) 2.997(2) 117.2(18) y
N3 H02 O4 4_545 0.91(3) 2.04(3) 2.8415(19) 146(2) y
C3 H3 O1 3_455 0.81(2) 2.26(2) 3.046(2) 161(2) y
C4 H4 O3 2_565 0.95(2) 2.42(2) 2.974(2) 116.9(16) y
C4 H4 O2 2_665 0.95(2) 2.58(2) 3.076(2) 113.0(16) y
C1 H1C N4 3_565 0.98 2.81 3.777(2) 168.0 y
C2 H2C N4 2_664 0.98 2.80 3.503(2) 129.7 y
C1 H1A O3 3_565 0.98 2.54 3.286(2) 132.8 ?
C2 H2A O1 2_664 0.98 2.56 3.413(2) 145.8 ?
C2 H2B O2 3_455 0.98 2.48 3.417(2) 160.9 ?
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
S2 N1 S1 O2 -42.50(11)
S2 N1 S1 O1 -169.73(9)
S2 N1 S1 C1 76.14(11)
S1 N1 S2 O3 -171.86(8)
S1 N1 S2 O4 -44.75(11)
S1 N1 S2 C2 73.33(11)
N4 C4 N3 C3 0.5(2)
N4 N2 C3 N3 0.62(19)
C4 N3 C3 N2 -0.68(18)
N3 C4 N4 N2 -0.1(2)
C3 N2 N4 C4 -0.30(19)