#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/19/8101979.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8101979
loop_
_publ_author_name
'Yang, L.'
'Yu, W.'
'Wu, T.'
'Zhang, T.-L.'
'Zhang, J.-G.'
'Guo, J.-Y.'
'Wu, R.-F.'
'Ren, F.-J.'
_publ_section_title
;
Crystal structure of carbohydrazidium(1+) p-toluene-sulfonate, 
(NH₂NHCONHNH₃)[CH₃C₆H₄SO₃]
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              281
_journal_page_last               282
_journal_volume                  221
_journal_year                    2006
_chemical_formula_structural     (NH2NHCONHNH3)[CH3C6H4SO3]
_chemical_formula_sum            'C16 H28 N8 O8 S2'
_chemical_formula_weight         524.58
_chemical_name_systematic
; 
 carbohydrazide p-toluenesulfonate 
;
_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            4
_cell_length_a                   10.646(1)
_cell_length_b                   8.185(1)
_cell_length_c                   26.402(4)
_cell_measurement_reflns_used    27
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.30
_cell_measurement_theta_min      2.47
_cell_volume                     2300.6(5)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            2625
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.54
_diffrn_standards_decay_%        5.21
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.9781
_exptl_absorpt_correction_T_min  0.9168
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flake
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0048(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2137
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0378
_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)+(0.0426P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                1491
_reflns_number_total             2137
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1788.cff
_cod_data_source_block           y1944
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        2300.7(4)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               8101979
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.56435(6) 0.22828(7) 0.63592(2) 0.02742(19) Uani 1 8 c d . . .
O1 O 0.08444(14) 0.14537(19) 0.73263(6) 0.0292(4) Uani 1 8 c d . . .
O2 O 0.43482(15) 0.1733(2) 0.64012(7) 0.0406(5) Uani 1 8 c d . . .
O3 O 0.65117(15) 0.0931(2) 0.64663(6) 0.0319(4) Uani 1 8 c d . . .
O4 O 0.5939(2) 0.3708(2) 0.66540(6) 0.0465(5) Uani 1 8 c d . . .
N1 N 0.26436(19) 0.3641(3) 0.70536(8) 0.0324(5) Uani 1 8 c d D . .
N2 N 0.13489(19) 0.3906(3) 0.69677(8) 0.0347(5) Uani 1 8 c d D . .
N3 N -0.06391(19) 0.2890(3) 0.69016(8) 0.0331(5) Uani 1 8 c d D . .
N4 N -0.15432(18) 0.1802(2) 0.71041(7) 0.0301(5) Uani 1 8 c d . . .
H4A H -0.1170 0.0873 0.7193 0.036 Uiso 1 8 c calc R . .
H4B H -0.2128 0.1598 0.6872 0.036 Uiso 1 8 c calc R . .
H4C H -0.1901 0.2253 0.7375 0.036 Uiso 1 8 c calc R . .
C1 C 0.0560(2) 0.2682(3) 0.70899(8) 0.0244(5) Uani 1 8 c d . . .
C2 C 0.6465(3) 0.4036(4) 0.41504(9) 0.0574(9) Uani 1 8 c d . . .
H2A H 0.7135 0.4818 0.4127 0.069 Uiso 0.50 8 c calc PR . .
H2B H 0.5712 0.4500 0.4012 0.069 Uiso 0.50 8 c calc PR . .
H2C H 0.6686 0.3072 0.3964 0.069 Uiso 0.50 8 c calc PR . .
H2D H 0.5887 0.3442 0.3941 0.069 Uiso 0.50 8 c calc PR . .
H2E H 0.7310 0.3760 0.4057 0.069 Uiso 0.50 8 c calc PR . .
H2F H 0.6336 0.5188 0.4105 0.069 Uiso 0.50 8 c calc PR . .
C3 C 0.6248(2) 0.3594(3) 0.47003(9) 0.0377(7) Uani 1 8 c d . . .
C4 C 0.6954(3) 0.4315(3) 0.50794(10) 0.0413(7) Uani 1 8 c d . . .
H4 H 0.7562 0.5082 0.4993 0.050 Uiso 1 8 c calc R . .
C5 C 0.6775(2) 0.3922(3) 0.55842(9) 0.0370(7) Uani 1 8 c d . . .
H5 H 0.7264 0.4414 0.5833 0.044 Uiso 1 8 c calc R . .
C6 C 0.5871(2) 0.2797(3) 0.57163(8) 0.0272(5) Uani 1 8 c d . . .
C7 C 0.5146(2) 0.2097(3) 0.53429(10) 0.0381(7) Uani 1 8 c d . . .
H7 H 0.4523 0.1351 0.5430 0.046 Uiso 1 8 c calc R . .
C8 C 0.5339(3) 0.2495(3) 0.48409(10) 0.0423(7) Uani 1 8 c d . . .
H8 H 0.4843 0.2009 0.4593 0.051 Uiso 1 8 c calc R . .
H3N H -0.092(2) 0.3817(18) 0.6797(9) 0.040(8) Uiso 1 8 c d D . .
H1A H 0.298(2) 0.4547(19) 0.7142(9) 0.045(9) Uiso 1 8 c d D . .
H2N H 0.111(2) 0.464(2) 0.6752(7) 0.035(7) Uiso 1 8 c d D . .
H1B H 0.295(3) 0.325(3) 0.6771(7) 0.064(10) Uiso 1 8 c d D . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S O2 114.68(12) . . ?
O4 S O3 111.66(11) . . ?
O2 S O3 110.40(10) . . ?
O4 S C6 107.28(11) . . ?
O2 S C6 106.08(11) . . ?
O3 S C6 106.18(10) . . ?
N2 N1 H1A 108.7(18) . . ?
N2 N1 H1B 106(2) . . ?
H1A N1 H1B 113(3) . . ?
C1 N2 N1 117.1(2) . . ?
C1 N2 H2N 119.6(17) . . ?
N1 N2 H2N 119.7(17) . . ?
C1 N3 N4 114.50(19) . . ?
C1 N3 H3N 123.1(18) . . ?
N4 N3 H3N 116.1(18) . . ?
N3 N4 H4A 109.5 . . ?
N3 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
N3 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
O1 C1 N2 125.5(2) . . ?
O1 C1 N3 121.0(2) . . ?
N2 C1 N3 113.5(2) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2D 109.5 . . ?
H2A C2 H2D 141.1 . . ?
H2B C2 H2D 56.3 . . ?
H2C C2 H2D 56.3 . . ?
C3 C2 H2E 109.5 . . ?
H2A C2 H2E 56.3 . . ?
H2B C2 H2E 141.1 . . ?
H2C C2 H2E 56.3 . . ?
H2D C2 H2E 109.5 . . ?
C3 C2 H2F 109.5 . . ?
H2A C2 H2F 56.3 . . ?
H2B C2 H2F 56.3 . . ?
H2C C2 H2F 141.1 . . ?
H2D C2 H2F 109.5 . . ?
H2E C2 H2F 109.5 . . ?
C8 C3 C4 117.8(2) . . ?
C8 C3 C2 121.6(3) . . ?
C4 C3 C2 120.6(3) . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 C6 C5 119.3(2) . . ?
C7 C6 S 120.82(19) . . ?
C5 C6 S 119.92(18) . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C3 C8 C7 121.3(2) . . ?
C3 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S O4 1.4372(18) . ?
S O2 1.4548(17) . ?
S O3 1.4692(16) . ?
S C6 1.765(2) . ?
O1 C1 1.221(3) . ?
N1 N2 1.414(3) . ?
N1 H1A 0.857(10) . ?
N1 H1B 0.873(10) . ?
N2 C1 1.347(3) . ?
N2 H2N 0.868(10) . ?
N3 C1 1.381(3) . ?
N3 N4 1.416(3) . ?
N3 H3N 0.861(10) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 H4C 0.8900 . ?
C2 C3 1.514(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 H2D 0.9600 . ?
C2 H2E 0.9600 . ?
C2 H2F 0.9600 . ?
C3 C8 1.373(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(3) . ?
C7 C8 1.380(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O2 0.873(10) 2.174(18) 2.950(3) 148(3) .
N1 H1A O1 0.857(10) 2.058(11) 2.900(3) 167(2) 8_665
N2 H2N O2 0.868(10) 2.005(12) 2.853(3) 165(2) 8_665
N3 H3N O3 0.861(10) 2.038(11) 2.894(3) 173(2) 8_665
N4 H4B O3 0.89 1.88 2.763(2) 170.1 1_455
N4 H4C N1 0.89 1.95 2.821(3) 165.8 6_557
N4 H4A O4 0.89 2.29 2.871(3) 123.1 8_655
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C1 O1 9.9(4) . . . . ?
N1 N2 C1 N3 -167.4(2) . . . . ?
N4 N3 C1 O1 14.3(3) . . . . ?
N4 N3 C1 N2 -168.2(2) . . . . ?
C8 C3 C4 C5 1.5(4) . . . . ?
C2 C3 C4 C5 -179.7(2) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 C7 -0.8(4) . . . . ?
C4 C5 C6 S 179.7(2) . . . . ?
O4 S C6 C7 -148.1(2) . . . . ?
O2 S C6 C7 -25.1(2) . . . . ?
O3 S C6 C7 92.4(2) . . . . ?
O4 S C6 C5 31.4(2) . . . . ?
O2 S C6 C5 154.4(2) . . . . ?
O3 S C6 C5 -88.1(2) . . . . ?
C5 C6 C7 C8 1.1(4) . . . . ?
S C6 C7 C8 -179.4(2) . . . . ?
C4 C3 C8 C7 -1.1(4) . . . . ?
C2 C3 C8 C7 180.0(3) . . . . ?
C6 C7 C8 C3 -0.1(4) . . . . ?
