#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:38:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179670 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/23/4512340.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_4512340
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, C5 H6 N, C H6 N3 '
_chemical_formula_sum            'C16 H18 N4 O6 S2'
_chemical_formula_weight         426.46
_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                92.179(9)
_cell_angle_beta                 99.398(16)
_cell_angle_gamma                90.530(13)
_cell_formula_units_Z            2
_cell_length_a                   7.982(6)
_cell_length_b                   8.142(6)
_cell_length_c                   14.067(12)
_cell_measurement_reflns_used    4132
_cell_measurement_temperature    178(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.50
_cell_volume                     901.2(12)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      178(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0725
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9677
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 180
_diffrn_standards_interval_time  9
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0461
_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)+(0.0529P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                2898
_reflns_number_total             4132
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5014895_si_003.cif
_cod_data_source_block           5-178K
_cod_depositor_comments
'Adding full bibliography for 4512336--4512373.cif.'
_cod_database_code               4512340
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
C1 C 0.1778(3) 0.7810(3) 0.34856(19) 0.0318(6) Uani 1 1 d .
H1B H 0.2155 0.7382 0.4085 0.038 Uiso 1 1 calc R
C2 C 0.2081(3) 0.7007(3) 0.2658(2) 0.0341(6) Uani 1 1 d .
H2C H 0.2702 0.6044 0.2692 0.041 Uiso 1 1 calc R
C3 C 0.1467(4) 0.7627(3) 0.17843(19) 0.0365(7) Uani 1 1 d .
H3C H 0.1659 0.7082 0.1220 0.044 Uiso 1 1 calc R
C4 C 0.0559(4) 0.9065(3) 0.1738(2) 0.0374(7) Uani 1 1 d .
H4D H 0.0118 0.9486 0.1145 0.045 Uiso 1 1 calc R
C5 C 0.0317(3) 0.9860(3) 0.2574(2) 0.0342(6) Uani 1 1 d .
H5B H -0.0271 1.0842 0.2557 0.041 Uiso 1 1 calc R
C6 C 0.4029(3) 0.1275(3) 0.09086(16) 0.0200(5) Uani 1 1 d .
C7 C 0.4651(3) 0.0528(3) 0.17457(16) 0.0239(5) Uani 1 1 d .
H7A H 0.4359 0.0918 0.2326 0.029 Uiso 1 1 calc R
C8 C 0.5730(3) -0.0829(3) 0.17351(17) 0.0266(5) Uani 1 1 d .
H8A H 0.6147 -0.1326 0.2309 0.032 Uiso 1 1 calc R
C9 C 0.3828(3) 0.1423(3) -0.08871(17) 0.0236(5) Uani 1 1 d .
H9A H 0.3112 0.2318 -0.0892 0.028 Uiso 1 1 calc R
C10 C 0.4450(3) 0.0690(3) -0.00016(16) 0.0202(5) Uani 1 1 d .
C11 C 0.6139(3) 0.7990(3) 0.52024(15) 0.0194(5) Uani 1 1 d .
C12 C 0.5124(3) 0.7205(3) 0.57468(17) 0.0234(5) Uani 1 1 d .
H12A H 0.5394 0.6156 0.5957 0.028 Uiso 1 1 calc R
C13 C 0.6328(3) 1.2014(3) 0.40106(17) 0.0254(5) Uani 1 1 d .
H13A H 0.7028 1.2570 0.3659 0.030 Uiso 1 1 calc R
C14 C 0.6721(3) 1.0468(3) 0.42817(16) 0.0211(5) Uani 1 1 d .
H14A H 0.7653 0.9960 0.4085 0.025 Uiso 1 1 calc R
C15 C 0.5730(3) 0.9604(3) 0.48630(15) 0.0172(5) Uani 1 1 d .
C16 C 0.7984(3) 0.4316(3) 0.19269(16) 0.0205(5) Uani 1 1 d .
N1 N 0.0929(3) 0.9222(3) 0.34147(16) 0.0329(5) Uani 1 1 d .
H1A H 0.0772 0.9740 0.3936 0.040 Uiso 1 1 calc R
N2 N 0.9306(2) 0.4100(2) 0.26071(14) 0.0260(5) Uani 1 1 d .
H2A H 0.9268 0.4417 0.3193 0.031 Uiso 1 1 calc R
H2B H 1.0204 0.3643 0.2463 0.031 Uiso 1 1 calc R
N3 N 0.8018(3) 0.3779(3) 0.10228(14) 0.0300(5) Uani 1 1 d .
H3A H 0.8902 0.3291 0.0882 0.036 Uiso 1 1 calc R
H3B H 0.7157 0.3920 0.0581 0.036 Uiso 1 1 calc R
N4 N 0.6593(2) 0.5021(2) 0.21438(14) 0.0251(5) Uani 1 1 d .
H4A H 0.6549 0.5340 0.2729 0.030 Uiso 1 1 calc R
H4B H 0.5735 0.5159 0.1699 0.030 Uiso 1 1 calc R
O1 O 0.7796(2) 0.6674(2) 0.39225(11) 0.0299(4) Uani 1 1 d .
O2 O 0.9414(2) 0.81722(19) 0.52972(12) 0.0250(4) Uani 1 1 d .
O3 O 0.8150(2) 0.5511(2) 0.55141(12) 0.0296(4) Uani 1 1 d .
O4 O 0.3605(2) 0.44059(19) 0.06712(12) 0.0254(4) Uani 1 1 d .
O5 O 0.1090(2) 0.2627(2) 0.03399(12) 0.0291(4) Uani 1 1 d .
O6 O 0.2483(2) 0.3183(2) 0.19878(11) 0.0270(4) Uani 1 1 d .
S1 S 0.26878(7) 0.30025(7) 0.09784(4) 0.02120(16) Uani 1 1 d .
S2 S 0.80243(7) 0.69832(7) 0.49686(4) 0.02046(15) Uani 1 1 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
N1 C1 C2 118.8(2) . .
N1 C1 H1B 120.6 . .
C2 C1 H1B 120.6 . .
C3 C2 C1 119.7(3) . .
C3 C2 H2C 120.2 . .
C1 C2 H2C 120.2 . .
C2 C3 C4 119.9(2) . .
C2 C3 H3C 120.0 . .
C4 C3 H3C 120.0 . .
C5 C4 C3 119.1(3) . .
C5 C4 H4D 120.5 . .
C3 C4 H4D 120.5 . .
N1 C5 C4 119.5(3) . .
N1 C5 H5B 120.2 . .
C4 C5 H5B 120.2 . .
C7 C6 C10 121.0(2) . .
C7 C6 S1 118.01(17) . .
C10 C6 S1 120.97(17) . .
C6 C7 C8 120.5(2) . .
C6 C7 H7A 119.8 . .
C8 C7 H7A 119.8 . .
C9 C8 C7 120.6(2) 2_655 .
C9 C8 H8A 119.7 2_655 .
C7 C8 H8A 119.7 . .
C8 C9 C10 120.8(2) 2_655 .
C8 C9 H9A 119.6 2_655 .
C10 C9 H9A 119.6 . .
C9 C10 C10 119.4(3) . 2_655
C9 C10 C6 122.9(2) . .
C10 C10 C6 117.7(3) 2_655 .
C12 C11 C15 120.7(2) . .
C12 C11 S2 118.17(18) . .
C15 C11 S2 121.12(17) . .
C11 C12 C13 120.1(2) . 2_676
C11 C12 H12A 119.9 . .
C13 C12 H12A 119.9 2_676 .
C14 C13 C12 121.1(2) . 2_676
C14 C13 H13A 119.4 . .
C12 C13 H13A 119.4 2_676 .
C13 C14 C15 121.2(2) . .
C13 C14 H14A 119.4 . .
C15 C14 H14A 119.4 . .
C14 C15 C15 118.5(3) . 2_676
C14 C15 C11 123.1(2) . .
C15 C15 C11 118.4(2) 2_676 .
N2 C16 N4 120.3(2) . .
N2 C16 N3 120.1(2) . .
N4 C16 N3 119.5(2) . .
C5 N1 C1 123.0(2) . .
C5 N1 H1A 118.5 . .
C1 N1 H1A 118.5 . .
C16 N2 H2A 120.0 . .
C16 N2 H2B 120.0 . .
H2A N2 H2B 120.0 . .
C16 N3 H3A 120.0 . .
C16 N3 H3B 120.0 . .
H3A N3 H3B 120.0 . .
C16 N4 H4A 120.0 . .
C16 N4 H4B 120.0 . .
H4A N4 H4B 120.0 . .
O5 S1 O6 112.64(11) . .
O5 S1 O4 112.79(11) . .
O6 S1 O4 112.10(10) . .
O5 S1 C6 107.27(11) . .
O6 S1 C6 105.59(10) . .
O4 S1 C6 105.83(11) . .
O3 S2 O1 114.01(11) . .
O3 S2 O2 113.24(11) . .
O1 S2 O2 111.33(10) . .
O3 S2 C11 106.27(11) . .
O1 S2 C11 105.94(10) . .
O2 S2 C11 105.23(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.339(3) .
C1 C2 1.370(4) .
C1 H1B 0.9300 .
C2 C3 1.365(4) .
C2 H2C 0.9300 .
C3 C4 1.381(4) .
C3 H3C 0.9300 .
C4 C5 1.363(4) .
C4 H4D 0.9300 .
C5 N1 1.330(4) .
C5 H5B 0.9300 .
C6 C7 1.368(3) .
C6 C10 1.441(3) .
C6 S1 1.785(2) .
C7 C8 1.408(3) .
C7 H7A 0.9300 .
C8 C9 1.370(3) 2_655
C8 H8A 0.9300 .
C9 C8 1.370(3) 2_655
C9 C10 1.419(3) .
C9 H9A 0.9300 .
C10 C10 1.432(4) 2_655
C11 C12 1.372(3) .
C11 C15 1.438(3) .
C11 S2 1.791(3) .
C12 C13 1.411(3) 2_676
C12 H12A 0.9300 .
C13 C14 1.354(3) .
C13 C12 1.411(3) 2_676
C13 H13A 0.9300 .
C14 C15 1.426(3) .
C14 H14A 0.9300 .
C15 C15 1.436(4) 2_676
C16 N2 1.322(3) .
C16 N4 1.329(3) .
C16 N3 1.334(3) .
N1 H1A 0.8600 .
N2 H2A 0.8600 .
N2 H2B 0.8600 .
N3 H3A 0.8600 .
N3 H3B 0.8600 .
N4 H4A 0.8600 .
N4 H4B 0.8600 .
O1 S2 1.465(2) .
O2 S2 1.4698(18) .
O3 S2 1.4432(19) .
O4 S1 1.4676(19) .
O5 S1 1.4576(19) .
O6 S1 1.458(2) .
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 H1A O2 0.86 2.00 2.782(3) 151.1 2_676
N3 H3B O4 0.86 2.28 2.973(3) 138.2 2_665
N3 H3A S1 0.86 3.01 3.796(4) 152.2 1_655
N3 H3A O5 0.86 2.08 2.925(3) 165.7 1_655
N2 H2B O6 0.86 2.07 2.908(3) 164.1 1_655
N2 H2A O3 0.86 2.51 3.063(3) 122.4 2_766
N4 H4B S1 0.86 3.00 3.624(3) 131.0 .
N4 H4B O4 0.86 2.11 2.918(3) 155.5 .
N4 H4A O1 0.86 2.07 2.816(3) 144.7 .
N2 H2A O1 0.86 2.47 3.122(3) 133.2 .
