#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/65/2206556.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_2206556
loop_
_publ_author_name
'S. Athimoolam'
'R. K. Rajaram'
_publ_section_title
;
 Dinicotinium sulfate
;
_journal_coeditor_code           SJ6123
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2764
_journal_page_last               o2767
_journal_paper_doi               10.1107/S1600536805023871
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '2C5 H6 N O2 +, S O4 2-'
_chemical_formula_moiety         '2C5 H6 N O2 +, S O4 2-'
_chemical_formula_sum            'C12 H12 N2 O8 S'
_chemical_formula_weight         344.30
_chemical_name_common            'Dinicotinium sulfate'
_chemical_name_systematic
;
Dinicotinium sulfate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL/PC
_cell_angle_alpha                101.253(11)
_cell_angle_beta                 95.746(8)
_cell_angle_gamma                102.685(11)
_cell_formula_units_Z            2
_cell_length_a                   6.9663(7)
_cell_length_b                   8.3306(14)
_cell_length_c                   12.5098(12)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.25
_cell_measurement_theta_min      9.97
_cell_volume                     686.85(16)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL/PC and PLATON (Spek, 2003)'
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  SHELXTL/PC
_computing_structure_solution    'SHELXTL/PC (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius MACH3 four-circle'
_diffrn_measurement_method       ω-2θ
_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  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3062
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_meas      1.654
_exptl_crystal_density_method
'flotation using a mixture of CCl~4~ and CHBr~3~'
_exptl_crystal_description       Block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.587
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2409
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0615
_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)+(0.0826P)²+2.2093P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1802
_refine_ls_wR_factor_ref         0.2047
_reflns_number_gt                1650
_reflns_number_total             2414
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj6123.cif
_cod_data_source_block           I
_cod_original_cell_volume        686.85(15)
_cod_database_code               2206556
_cod_database_fobs_code          2206556
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N11 0.2066(7) 0.9219(6) -0.0206(4) 0.0355(11) Uani d . 1 N
H11 0.1538 0.9746 -0.0634 0.043 Uiso calc R 1 H
C12 0.1797(8) 0.7556(7) -0.0536(4) 0.0322(12) Uani d . 1 C
H12 0.1026 0.6984 -0.1209 0.039 Uiso calc R 1 H
C13 0.2665(8) 0.6683(7) 0.0124(4) 0.0319(12) Uani d . 1 C
C14 0.3770(8) 0.7564(7) 0.1119(5) 0.0375(13) Uani d . 1 C
H14 0.4368 0.6999 0.1575 0.045 Uiso calc R 1 H
C15 0.3997(9) 0.9278(8) 0.1445(5) 0.0394(14) Uani d . 1 C
H15 0.4737 0.9870 0.2123 0.047 Uiso calc R 1 H
C16 0.3125(9) 1.0108(8) 0.0766(5) 0.0394(14) Uani d . 1 C
H16 0.3266 1.1267 0.0975 0.047 Uiso calc R 1 H
C131 0.2393(8) 0.4808(7) -0.0222(5) 0.0355(13) Uani d . 1 C
O1A 0.2902(7) 0.3992(5) 0.0400(4) 0.0515(12) Uani d . 1 O
O1B 0.1521(7) 0.4182(5) -0.1244(3) 0.0488(11) Uani d . 1 O
H1B 0.1362 0.3154 -0.1387 0.073 Uiso calc R 1 H
N21 0.6370(7) 0.7967(6) 0.5124(4) 0.0344(11) Uani d . 1 N
H21 0.7086 0.8762 0.5649 0.041 Uiso calc R 1 H
C22 0.7216(8) 0.6820(7) 0.4584(4) 0.0317(12) Uani d . 1 C
H22 0.8568 0.6907 0.4765 0.038 Uiso calc R 1 H
C23 0.6081(7) 0.5512(6) 0.3762(4) 0.0282(11) Uani d . 1 C
C24 0.4074(8) 0.5456(7) 0.3463(5) 0.0359(13) Uani d . 1 C
H24 0.3288 0.4603 0.2894 0.043 Uiso calc R 1 H
C25 0.3272(8) 0.6704(7) 0.4034(5) 0.0390(14) Uani d . 1 C
H25 0.1948 0.6702 0.3840 0.047 Uiso calc R 1 H
C26 0.4430(8) 0.7910(7) 0.4867(5) 0.0359(13) Uani d . 1 C
H26 0.3883 0.8712 0.5270 0.043 Uiso calc R 1 H
C231 0.6902(8) 0.4115(7) 0.3203(4) 0.0307(12) Uani d . 1 C
O2A 0.5922(6) 0.2982(5) 0.2487(3) 0.0463(11) Uani d . 1 O
O2B 0.8761(6) 0.4250(5) 0.3616(3) 0.0412(10) Uani d . 1 O
H2B 0.9085 0.3378 0.3370 0.062 Uiso calc R 1 H
S1 0.9467(2) 0.00558(17) 0.28921(11) 0.0305(4) Uani d . 1 S
O1 0.9010(6) -0.0943(5) 0.1744(3) 0.0414(10) Uani d . 1 O
O2 1.0223(6) 0.1826(5) 0.2843(3) 0.0392(10) Uani d . 1 O
O3 1.1048(7) -0.0493(5) 0.3486(4) 0.0538(13) Uani d . 1 O
O4 0.7687(7) -0.0148(6) 0.3400(4) 0.0547(12) Uani d . 1 O
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'
Cl Cl 0.1484 0.1585 '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
C12 N11 C16 122.9(5) y
C12 N11 H11 118.5 ?
C16 N11 H11 118.5 ?
N11 C12 C13 119.8(5) ?
N11 C12 H12 120.1 ?
C13 C12 H12 120.1 ?
C14 C13 C12 118.5(5) ?
C14 C13 C131 120.3(5) ?
C12 C13 C131 121.2(5) ?
C13 C14 C15 120.4(5) ?
C13 C14 H14 119.8 ?
C15 C14 H14 119.8 ?
C16 C15 C14 119.6(5) ?
C16 C15 H15 120.2 ?
C14 C15 H15 120.2 ?
N11 C16 C15 118.8(5) ?
N11 C16 H16 120.6 ?
C15 C16 H16 120.6 ?
O1A C131 O1B 124.9(5) y
O1A C131 C13 122.1(5) ?
O1B C131 C13 113.0(5) ?
C131 O1B H1B 109.5 ?
C22 N21 C26 121.9(5) y
C22 N21 H21 119.1 ?
C26 N21 H21 119.1 ?
N21 C22 C23 119.8(5) ?
N21 C22 H22 120.1 ?
C23 C22 H22 120.1 ?
C22 C23 C24 119.1(5) ?
C22 C23 C231 122.1(5) ?
C24 C23 C231 118.7(5) ?
C25 C24 C23 118.8(5) ?
C25 C24 H24 120.6 ?
C23 C24 H24 120.6 ?
C26 C25 C24 119.5(5) ?
C26 C25 H25 120.2 ?
C24 C25 H25 120.2 ?
N21 C26 C25 120.7(5) ?
N21 C26 H26 119.6 ?
C25 C26 H26 119.6 ?
O2A C231 O2B 125.0(5) y
O2A C231 C23 122.2(5) ?
O2B C231 C23 112.7(4) ?
C231 O2B H2B 109.5 ?
O4 S1 O2 110.7(3) ?
O4 S1 O3 112.0(3) ?
O2 S1 O3 108.8(2) ?
O4 S1 O1 109.7(3) ?
O2 S1 O1 106.9(2) ?
O3 S1 O1 108.6(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N11 C12 1.331(7) y
N11 C16 1.342(7) y
N11 H11 0.8600 ?
C12 C13 1.380(8) ?
C12 H12 0.9300 ?
C13 C14 1.372(8) ?
C13 C131 1.501(8) ?
C14 C15 1.375(8) ?
C14 H14 0.9300 ?
C15 C16 1.371(8) ?
C15 H15 0.9300 ?
C16 H16 0.9300 ?
C131 O1A 1.204(7) y
C131 O1B 1.311(7) y
O1B H1B 0.8200 ?
N21 C22 1.338(7) y
N21 C26 1.345(7) y
N21 H21 0.8600 ?
C22 C23 1.375(7) ?
C22 H22 0.9300 ?
C23 C24 1.399(7) ?
C23 C231 1.492(7) ?
C24 C25 1.395(8) ?
C24 H24 0.9300 ?
C25 C26 1.347(8) ?
C25 H25 0.9300 ?
C26 H26 0.9300 ?
C231 O2A 1.193(6) y
C231 O2B 1.318(6) y
O2B H2B 0.8200 ?
S1 O4 1.442(4) ?
S1 O2 1.469(4) ?
S1 O3 1.471(4) ?
S1 O1 1.478(4) ?
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
N11 H11 O1 2_665 0.86 1.91 2.755(6) 165
O1B H1B O1 2_655 0.82 1.76 2.582(6) 178
O2B H2B O2 . 0.82 1.72 2.528(5) 168
N21 H21 O3 2_766 0.86 1.80 2.641(6) 167
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_publ_flag
C16 N11 C12 C13 -1.5(8) ?
N11 C12 C13 C14 0.9(8) ?
N11 C12 C13 C131 -180.0(5) ?
C12 C13 C14 C15 0.1(8) ?
C131 C13 C14 C15 -179.1(5) ?
C13 C14 C15 C16 -0.5(9) ?
C12 N11 C16 C15 1.0(8) ?
C14 C15 C16 N11 0.0(8) ?
C14 C13 C131 O1A 9.6(8) y
C12 C13 C131 O1A -169.5(5) ?
C14 C13 C131 O1B -171.9(5) y
C12 C13 C131 O1B 9.0(7) ?
C26 N21 C22 C23 -1.8(8) ?
N21 C22 C23 C24 3.4(8) ?
N21 C22 C23 C231 -174.4(5) ?
C22 C23 C24 C25 -2.0(8) ?
C231 C23 C24 C25 176.0(5) ?
C23 C24 C25 C26 -1.1(9) ?
C22 N21 C26 C25 -1.5(8) ?
C24 C25 C26 N21 2.9(9) ?
C22 C23 C231 O2A -179.8(6) ?
C24 C23 C231 O2A 2.3(8) y
C22 C23 C231 O2B 2.8(8) ?
C24 C23 C231 O2B -175.1(5) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21129064
