#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:38:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179670 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/23/4512363.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_4512363
loop_
_publ_author_name
'Shi, Chao'
'Wei, Bin'
'Zhang, Wen'
_publ_section_title
;
 Toward Understanding the Origin of Structural Phase Transition in
 Guanidinium Pyridinium 1,5-Naphthalenedisulfonate
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              6570
_journal_paper_doi               10.1021/cg5014895
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C10 H6 O6 S2, C H6 N3, C2 H8 N, H2 O'
_chemical_formula_sum            'C13 H22 N4 O7 S2'
_chemical_formula_weight         410.47
_chemical_name_systematic
; 
 ? 
;
_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           SHELXL-97
_cell_angle_alpha                97.23(3)
_cell_angle_beta                 101.57(3)
_cell_angle_gamma                90.37(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7810(18)
_cell_length_b                   9.3448(19)
_cell_length_c                   11.695(2)
_cell_measurement_reflns_used    3638
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     932.2(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω 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  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9781
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_interval_time  9
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_T_max  0.525
_exptl_absorpt_correction_T_min  0.520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.933
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0647
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0621P)²+0.9509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1662
_reflns_number_gt                2763
_reflns_number_total             4258
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5014895_si_002.cif
_cod_data_source_block           2EA
_cod_depositor_comments
'Adding full bibliography for 4512336--4512373.cif.'
_cod_database_code               4512363
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_calc_flag
_atom_site_refinement_flags
C11 C 0.5191(7) 1.5608(6) 0.2948(6) 0.0989(19) Uani 1 1 d .
H11A H 0.6066 1.5547 0.2569 0.148 Uiso 1 1 calc R
H11B H 0.5542 1.5929 0.3773 0.148 Uiso 1 1 calc R
H11C H 0.4474 1.6283 0.2605 0.148 Uiso 1 1 calc R
C12 C 0.4465(6) 1.4277(6) 0.2803(6) 0.103(2) Uani 1 1 d .
H12A H 0.3644 1.4294 0.3249 0.123 Uiso 1 1 calc R
H12B H 0.5201 1.3557 0.3061 0.123 Uiso 1 1 calc R
C20 C 0.8779(4) 1.3541(4) 0.3981(3) 0.0458(9) Uani 1 1 d .
H20 H 0.8501 1.3227 0.3178 0.055 Uiso 1 1 calc R
N4 N 0.3787(4) 1.3945(4) 0.1472(3) 0.0573(9) Uani 1 1 d .
H4A H 0.3134 1.4628 0.1248 0.086 Uiso 1 1 calc R
H4B H 0.3281 1.3092 0.1323 0.086 Uiso 1 1 calc R
H4C H 0.4557 1.3922 0.1078 0.086 Uiso 1 1 calc R
S1 S 0.41725(11) 1.02630(10) 0.20327(7) 0.0421(2) Uani 1 1 d .
O6 O 0.2801(3) 1.0900(3) 0.1404(2) 0.0471(6) Uani 1 1 d .
C7 C 0.3960(4) 1.0433(3) 0.3529(3) 0.0341(7) Uani 1 1 d .
C8 C 0.5105(3) 0.9891(3) 0.4408(3) 0.0310(7) Uani 1 1 d .
O4 O 0.4270(4) 0.8738(3) 0.1650(2) 0.0692(9) Uani 1 1 d .
C6 C 0.2694(4) 1.1129(4) 0.3812(3) 0.0418(8) Uani 1 1 d .
H6 H 0.1963 1.1475 0.3228 0.050 Uiso 1 1 calc R
N1 N 0.7728(3) 0.8273(3) 0.1310(3) 0.0477(7) Uani 1 1 d .
H1A H 0.6818 0.8556 0.1383 0.057 Uiso 1 1 calc R
H1B H 0.7922 0.7369 0.1262 0.057 Uiso 1 1 calc R
O5 O 0.5599(3) 1.1063(3) 0.2040(2) 0.0614(8) Uani 1 1 d .
C9 C 0.6435(4) 0.9163(4) 0.4159(3) 0.0404(8) Uani 1 1 d .
H9 H 0.6582 0.9013 0.3387 0.048 Uiso 1 1 calc R
C10 C 0.8830(4) 0.9229(4) 0.1274(3) 0.0393(8) Uani 1 1 d .
N3 N 0.8539(4) 1.0607(3) 0.1348(3) 0.0504(8) Uani 1 1 d .
H3A H 0.7629 1.0892 0.1420 0.061 Uiso 1 1 calc R
H3B H 0.9256 1.1226 0.1324 0.061 Uiso 1 1 calc R
C5 C 0.2499(4) 1.1322(4) 0.4975(3) 0.0461(9) Uani 1 1 d .
H5 H 0.1630 1.1787 0.5160 0.055 Uiso 1 1 calc R
N2 N 1.0225(4) 0.8783(4) 0.1153(3) 0.0539(8) Uani 1 1 d .
H2A H 1.0943 0.9399 0.1122 0.065 Uiso 1 1 calc R
H2B H 1.0412 0.7878 0.1105 0.065 Uiso 1 1 calc R
S2 S 0.99020(10) 1.50402(10) 0.79488(9) 0.0450(3) Uani 1 1 d .
O1 O 0.8877(3) 1.4147(3) 0.8418(2) 0.0544(7) Uani 1 1 d .
O2 O 0.9565(3) 1.6557(3) 0.8121(2) 0.0567(7) Uani 1 1 d .
O3 O 1.1531(3) 1.4754(3) 0.8372(2) 0.0557(7) Uani 1 1 d .
C4 C 1.0185(4) 1.5245(3) 0.5612(3) 0.0391(8) Uani 1 1 d .
C3 C 0.9524(4) 1.4483(4) 0.6397(3) 0.0406(8) Uani 1 1 d .
C1 C 0.8193(4) 1.2837(4) 0.4746(4) 0.0544(10) Uani 1 1 d .
H1 H 0.7538 1.2030 0.4461 0.065 Uiso 1 1 calc R
C2 C 0.8551(4) 1.3296(4) 0.5961(4) 0.0488(9) Uani 1 1 d .
H2 H 0.8130 1.2798 0.6471 0.059 Uiso 1 1 calc R
O7 O 0.6125(3) 1.3591(4) 0.0100(3) 0.0762(10) Uani 1 1 d D
H2W H 0.618(5) 1.277(3) -0.032(4) 0.091 Uiso 1 1 d D
H1W H 0.698(4) 1.371(5) 0.060(3) 0.091 Uiso 1 1 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
C12 C11 H11A 109.5 . .
C12 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C12 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C11 C12 N4 105.2(5) . .
C11 C12 H12A 110.7 . .
N4 C12 H12A 110.7 . .
C11 C12 H12B 110.7 . .
N4 C12 H12B 110.7 . .
H12A C12 H12B 108.8 . .
C1 C20 C4 120.8(4) . 2_786
C1 C20 H20 119.6 . .
C4 C20 H20 119.6 2_786 .
C12 N4 H4A 109.5 . .
C12 N4 H4B 109.5 . .
H4A N4 H4B 109.5 . .
C12 N4 H4C 109.5 . .
H4A N4 H4C 109.5 . .
H4B N4 H4C 109.5 . .
O4 S1 O5 112.20(19) . .
O4 S1 O6 113.16(16) . .
O5 S1 O6 112.70(16) . .
O4 S1 C7 106.94(16) . .
O5 S1 C7 105.76(16) . .
O6 S1 C7 105.38(15) . .
C6 C7 C8 121.3(3) . .
C6 C7 S1 117.9(2) . .
C8 C7 S1 120.7(2) . .
C9 C8 C8 118.7(3) . 2_676
C9 C8 C7 123.4(3) . .
C8 C8 C7 117.9(3) 2_676 .
C7 C6 C5 120.0(3) . .
C7 C6 H6 120.0 . .
C5 C6 H6 120.0 . .
C10 N1 H1A 120.0 . .
C10 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
C5 C9 C8 121.3(3) 2_676 .
C5 C9 H9 119.4 2_676 .
C8 C9 H9 119.4 . .
N3 C10 N1 120.2(3) . .
N3 C10 N2 120.2(3) . .
N1 C10 N2 119.6(3) . .
C10 N3 H3A 120.0 . .
C10 N3 H3B 120.0 . .
H3A N3 H3B 120.0 . .
C9 C5 C6 120.8(3) 2_676 .
C9 C5 H5 119.6 2_676 .
C6 C5 H5 119.6 . .
C10 N2 H2A 120.0 . .
C10 N2 H2B 120.0 . .
H2A N2 H2B 120.0 . .
O2 S2 O1 112.62(16) . .
O2 S2 O3 113.09(17) . .
O1 S2 O3 111.76(17) . .
O2 S2 C3 107.10(16) . .
O1 S2 C3 105.91(16) . .
O3 S2 C3 105.73(16) . .
C4 C4 C20 118.7(4) 2_786 2_786
C4 C4 C3 118.9(4) 2_786 .
C20 C4 C3 122.3(3) 2_786 .
C2 C3 C4 120.1(3) . .
C2 C3 S2 117.9(3) . .
C4 C3 S2 122.0(2) . .
C20 C1 C2 121.5(3) . .
C20 C1 H1 119.3 . .
C2 C1 H1 119.3 . .
C3 C2 C1 120.0(3) . .
C3 C2 H2 120.0 . .
C1 C2 H2 120.0 . .
H2W O7 H1W 106(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C11 C12 1.370(7) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 N4 1.541(7) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C20 C1 1.352(5) .
C20 C4 1.421(4) 2_786
C20 H20 0.9300 .
N4 H4A 0.8900 .
N4 H4B 0.8900 .
N4 H4C 0.8900 .
S1 O4 1.447(3) .
S1 O5 1.452(3) .
S1 O6 1.452(2) .
S1 C7 1.784(3) .
C7 C6 1.368(5) .
C7 C8 1.431(4) .
C8 C9 1.417(4) .
C8 C8 1.424(6) 2_676
C6 C5 1.394(5) .
C6 H6 0.9300 .
N1 C10 1.323(4) .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
C9 C5 1.360(5) 2_676
C9 H9 0.9300 .
C10 N3 1.310(4) .
C10 N2 1.324(4) .
N3 H3A 0.8600 .
N3 H3B 0.8600 .
C5 C9 1.360(5) 2_676
C5 H5 0.9300 .
N2 H2A 0.8600 .
N2 H2B 0.8600 .
S2 O2 1.447(3) .
S2 O1 1.453(3) .
S2 O3 1.455(3) .
S2 C3 1.786(4) .
C4 C4 1.418(7) 2_786
C4 C20 1.421(4) 2_786
C4 C3 1.436(5) .
C3 C2 1.375(5) .
C1 C2 1.403(5) .
C1 H1 0.9300 .
C2 H2 0.9300 .
O7 H2W 0.860(19) .
O7 H1W 0.848(19) .
