#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/16/2221679.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_2221679
loop_
_publ_author_name
'Feng, Lingling'
'Hou, Yubang'
'Yong, Xuejian'
'Bao, Feng'
_publ_section_title
;
 Bis(3-nitroanilinium) sulfate
;
_journal_coeditor_code           HB2912
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1086
_journal_paper_doi               10.1107/S1600536809013762
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '2C6 H7 N2 O2 +, S1 O4 2-'
_chemical_formula_moiety         '2(C6 H7 N2 O2 +), O4 S 2-'
_chemical_formula_sum            'C12 H14 N4 O8 S'
_chemical_formula_weight         374.33
_chemical_name_systematic
;
Bis(3-nitroanilinium) sulfate
;
_space_group_IT_number           57
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_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                   7.9177(16)
_cell_length_b                   30.843(6)
_cell_length_c                   6.3924(13)
_cell_measurement_reflns_used    6890
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.57
_cell_volume                     1561.1(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART 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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12364
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.442
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0614
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0402P)²+2.0956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1441
_reflns_number_gt                1735
_reflns_number_total             1845
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2912.cif
_cod_data_source_block           I
_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 1527 2010-12-29 10:47:43Z saulius 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2221679
_cod_database_fobs_code          2221679
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, 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 0.6618(4) 0.09205(10) 0.2500 0.0299(7) Uani d S 1 . .
C C2 0.5199(4) 0.11814(12) 0.2500 0.0356(8) Uani d S 1 . .
H H2 0.4126 0.1059 0.2500 0.043 Uiso calc SR 1 . .
C C3 0.5394(5) 0.16246(12) 0.2500 0.0448(10) Uani d S 1 . .
H H3 0.4444 0.1802 0.2500 0.054 Uiso calc SR 1 . .
C C4 0.6984(5) 0.18093(11) 0.2500 0.0434(9) Uani d S 1 . .
H H4 0.7120 0.2109 0.2500 0.052 Uiso calc SR 1 . .
C C5 0.8355(4) 0.15378(11) 0.2500 0.0344(8) Uani d S 1 . .
C C6 0.8229(4) 0.10938(11) 0.2500 0.0321(7) Uani d S 1 . .
H H6 0.9182 0.0918 0.2500 0.039 Uiso calc SR 1 . .
N N1 0.6439(4) 0.04502(9) 0.2500 0.0467(9) Uani d S 1 . .
H H1A 0.7456 0.0327 0.2500 0.056 Uiso d SR 1 . .
H H1B 0.5874 0.0368 0.1363 0.056 Uiso d R 1 . .
N N2 1.0069(4) 0.17275(11) 0.2500 0.0446(8) Uani d S 1 . .
O O1 1.1266(3) 0.14857(10) 0.2500 0.0581(9) Uani d S 1 . .
O O2 1.0177(4) 0.21214(10) 0.2500 0.0713(11) Uani d S 1 . .
C C7 0.1526(4) 0.10811(11) 0.7500 0.0313(7) Uani d S 1 . .
C C8 0.0172(5) 0.13591(12) 0.7500 0.0376(8) Uani d S 1 . .
H H8 -0.0922 0.1250 0.7500 0.045 Uiso calc SR 1 . .
C C9 0.0437(5) 0.18007(13) 0.7500 0.0470(10) Uani d S 1 . .
H H9 -0.0482 0.1989 0.7500 0.056 Uiso calc SR 1 . .
C C10 0.2057(5) 0.19658(12) 0.7500 0.0472(10) Uani d S 1 . .
H H10 0.2246 0.2263 0.7500 0.057 Uiso calc SR 1 . .
C C11 0.3388(4) 0.16774(12) 0.7500 0.0392(9) Uani d S 1 . .
C C12 0.3170(4) 0.12348(11) 0.7500 0.0346(8) Uani d S 1 . .
H H12 0.4088 0.1047 0.7500 0.042 Uiso calc SR 1 . .
N N3 0.1249(4) 0.06160(9) 0.7500 0.0367(7) Uani d S 1 . .
H H3A 0.0142 0.0558 0.7500 0.044 Uiso d SR 1 . .
H H3B 0.1712 0.0502 0.6268 0.044 Uiso d R 1 . .
N N4 0.5129(5) 0.18455(13) 0.7500 0.0555(10) Uani d S 1 . .
O O3 0.6279(4) 0.15917(12) 0.7500 0.0699(10) Uani d S 1 . .
O O4 0.5318(5) 0.22352(11) 0.7500 0.0996(16) Uani d S 1 . .
S S1 0.21460(11) 0.00780(3) 0.2500 0.0338(3) Uani d S 1 . .
O O5 0.3083(3) 0.02283(8) 0.0650(4) 0.0644(7) Uani d . 1 . .
O O6 0.0436(4) 0.02484(9) 0.2500 0.0573(9) Uani d S 1 . .
O O7 0.2120(4) -0.03918(9) 0.2500 0.0680(11) Uani d S 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
C2 C1 C6 . . 121.6(3) ?
C2 C1 N1 . . 120.0(3) ?
C6 C1 N1 . . 118.3(3) ?
C3 C2 C1 . . 119.2(3) ?
C3 C2 H2 . . 120.4 ?
C1 C2 H2 . . 120.4 ?
C2 C3 C4 . . 120.8(3) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
C5 C4 C3 . . 118.0(3) ?
C5 C4 H4 . . 121.0 ?
C3 C4 H4 . . 121.0 ?
C4 C5 C6 . . 123.5(3) ?
C4 C5 N2 . . 119.0(3) ?
C6 C5 N2 . . 117.5(3) ?
C5 C6 C1 . . 116.9(3) ?
C5 C6 H6 . . 121.5 ?
C1 C6 H6 . . 121.5 ?
C1 N1 H1A . . 109.6 ?
C1 N1 H1B . . 109.4 ?
H1A N1 H1B . . 109.5 ?
O1 N2 O2 . . 124.2(3) ?
O1 N2 C5 . . 118.5(3) ?
O2 N2 C5 . . 117.4(3) ?
C8 C7 C12 . . 121.3(3) ?
C8 C7 N3 . . 120.0(3) ?
C12 C7 N3 . . 118.7(3) ?
C7 C8 C9 . . 119.9(3) ?
C7 C8 H8 . . 120.0 ?
C9 C8 H8 . . 120.0 ?
C8 C9 C10 . . 120.4(3) ?
C8 C9 H9 . . 119.8 ?
C10 C9 H9 . . 119.8 ?
C11 C10 C9 . . 118.2(3) ?
C11 C10 H10 . . 120.9 ?
C9 C10 H10 . . 120.9 ?
C12 C11 C10 . . 123.0(3) ?
C12 C11 N4 . . 117.8(3) ?
C10 C11 N4 . . 119.2(3) ?
C11 C12 C7 . . 117.2(3) ?
C11 C12 H12 . . 121.4 ?
C7 C12 H12 . . 121.4 ?
C7 N3 H3A . . 110.2 ?
C7 N3 H3B . . 108.1 ?
H3A N3 H3B . . 108.0 ?
O3 N4 O4 . . 123.6(4) ?
O3 N4 C11 . . 118.7(4) ?
O4 N4 C11 . . 117.7(4) ?
O7 S1 O6 . . 110.40(17) ?
O7 S1 O5 . 6_556 108.80(12) ?
O6 S1 O5 . 6_556 110.87(11) ?
O7 S1 O5 . . 108.80(12) ?
O6 S1 O5 . . 110.87(11) ?
O5 S1 O5 6_556 . 107.01(19) ?
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 C2 . 1.381(5) ?
C1 C6 . 1.383(4) ?
C1 N1 . 1.458(4) ?
C2 C3 . 1.376(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.382(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.371(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.373(5) ?
C5 N2 . 1.478(4) ?
C6 H6 . 0.9300 ?
N1 H1A . 0.8900 ?
N1 H1B . 0.8900 ?
N2 O1 . 1.206(4) ?
N2 O2 . 1.218(4) ?
C7 C8 . 1.373(5) ?
C7 C12 . 1.386(5) ?
C7 N3 . 1.451(4) ?
C8 C9 . 1.378(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.380(6) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.379(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.376(5) ?
C11 N4 . 1.472(5) ?
C12 H12 . 0.9300 ?
N3 H3A . 0.8942 ?
N3 H3B . 0.9368 ?
N4 O3 . 1.201(5) ?
N4 O4 . 1.211(5) ?
S1 O7 . 1.449(3) ?
S1 O6 . 1.452(3) ?
S1 O5 6_556 1.471(2) ?
S1 O5 . 1.471(2) ?
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 O6 1_655 0.89 2.37 3.226(4) 161
N1 H1B O5 . 0.89 2.30 2.987(4) 134
N1 H1B O5 5_655 0.89 2.39 2.928(3) 119
N3 H3A O7 5_556 0.89 1.86 2.755(4) 176
N3 H3B O5 6_556 0.94 1.84 2.756(3) 164
C4 H4 O4 4_556 0.93 2.48 3.229(5) 138
C6 H6 O6 1_655 0.93 2.29 3.139(4) 151
C8 H8 O3 1_455 0.93 2.45 3.165(5) 133
C10 H10 O2 4_456 0.93 2.51 3.184(5) 130
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.0 ?
N1 C1 C2 C3 . . . . 180.0 ?
C1 C2 C3 C4 . . . . 0.0 ?
C2 C3 C4 C5 . . . . 0.0 ?
C3 C4 C5 C6 . . . . 0.0 ?
C3 C4 C5 N2 . . . . 180.0 ?
C4 C5 C6 C1 . . . . 0.0 ?
N2 C5 C6 C1 . . . . 180.0 ?
C2 C1 C6 C5 . . . . 0.0 ?
N1 C1 C6 C5 . . . . 180.0 ?
C4 C5 N2 O1 . . . . 180.0 ?
C6 C5 N2 O1 . . . . 0.0 ?
C4 C5 N2 O2 . . . . 0.0 ?
C6 C5 N2 O2 . . . . 180.0 ?
C12 C7 C8 C9 . . . . 0.0 ?
N3 C7 C8 C9 . . . . 180.0 ?
C7 C8 C9 C10 . . . . 0.0 ?
C8 C9 C10 C11 . . . . 0.0 ?
C9 C10 C11 C12 . . . . 0.0 ?
C9 C10 C11 N4 . . . . 180.0 ?
C10 C11 C12 C7 . . . . 0.0 ?
N4 C11 C12 C7 . . . . 180.0 ?
C8 C7 C12 C11 . . . . 0.0 ?
N3 C7 C12 C11 . . . . 180.0 ?
C12 C11 N4 O3 . . . . 0.0 ?
C10 C11 N4 O3 . . . . 180.0 ?
C12 C11 N4 O4 . . . . 180.0 ?
C10 C11 N4 O4 . . . . 0.0 ?
