#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:38:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179670 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/23/4512369.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_4512369
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, C3 H10 N'
_chemical_formula_sum            'C14 H17 N5 O6 S2'
_chemical_formula_weight         415.45
_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                87.42(3)
_cell_angle_beta                 80.55(3)
_cell_angle_gamma                84.57(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1391(16)
_cell_length_b                   8.4780(17)
_cell_length_c                   12.896(3)
_cell_measurement_reflns_used    3638
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     873.5(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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0616
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9009
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.20
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_interval_time  9
_exptl_absorpt_coefficient_mu    0.350
_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    1.580
_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         0.271
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0422P)²+0.4893P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1208
_reflns_number_gt                2958
_reflns_number_total             3971
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5014895_si_002.cif
_cod_data_source_block           8PZ
_cod_depositor_comments
'Adding full bibliography for 4512336--4512373.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4512369
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
S1 S 0.13765(8) 0.75170(7) 0.53335(5) 0.02528(17) Uani 1 1 d .
O2 O 0.0987(2) 0.7365(2) 0.42749(14) 0.0364(5) Uani 1 1 d .
O3 O 0.1238(2) 0.9161(2) 0.56460(16) 0.0365(5) Uani 1 1 d .
C3 C 0.4132(3) 0.5232(3) 0.50151(18) 0.0201(5) Uani 1 1 d .
O1 O 0.0439(2) 0.6508(2) 0.61085(14) 0.0327(4) Uani 1 1 d .
C4 C 0.3541(3) 0.6849(3) 0.52591(19) 0.0219(5) Uani 1 1 d .
C5 C 0.4622(3) 0.7903(3) 0.5450(2) 0.0283(6) Uani 1 1 d .
H5A H 0.4222 0.8944 0.5605 0.034 Uiso 1 1 calc R
C2 C 0.3052(3) 0.4092(3) 0.4802(2) 0.0268(5) Uani 1 1 d .
H2B H 0.1921 0.4393 0.4809 0.032 Uiso 1 1 calc R
C6 C 0.6336(3) 0.7427(3) 0.5412(2) 0.0309(6) Uani 1 1 d .
H6A H 0.7058 0.8161 0.5535 0.037 Uiso 1 1 calc R
N4 N 0.8529(3) 0.8898(4) 0.7596(2) 0.0565(8) Uani 1 1 d .
H4A H 0.9481 0.8358 0.7443 0.068 Uiso 1 1 calc R
C13 C 0.7393(5) 0.8608(4) 0.8394(3) 0.0570(9) Uani 1 1 d .
H13A H 0.7465 0.7785 0.8890 0.068 Uiso 1 1 calc R
N5 N 0.8012(4) 1.0120(4) 0.7067(2) 0.0674(9) Uani 1 1 d .
H5B H 0.8562 1.0522 0.6506 0.081 Uiso 1 1 calc R
C14 C 0.6098(4) 0.9706(5) 0.8376(3) 0.0676(11) Uani 1 1 d .
H14A H 0.5107 0.9804 0.8854 0.081 Uiso 1 1 calc R
C15 C 0.6538(6) 1.0642(4) 0.7516(4) 0.0749(13) Uani 1 1 d .
H15A H 0.5890 1.1510 0.7288 0.090 Uiso 1 1 calc R
S2 S 0.20411(8) 0.74962(8) 0.89521(5) 0.02965(18) Uani 1 1 d .
O4 O 0.2077(3) 0.8756(2) 0.96720(16) 0.0399(5) Uani 1 1 d .
O5 O 0.2157(3) 0.8064(2) 0.78639(15) 0.0418(5) Uani 1 1 d .
O6 O 0.0620(2) 0.6539(2) 0.92656(16) 0.0397(5) Uani 1 1 d .
C8 C 0.4262(3) 0.5534(3) 1.00036(19) 0.0273(6) Uani 1 1 d .
C9 C 0.3860(3) 0.6157(3) 0.9016(2) 0.0293(6) Uani 1 1 d .
C10 C 0.4861(4) 0.5756(3) 0.8089(2) 0.0354(6) Uani 1 1 d .
H10A H 0.4570 0.6167 0.7456 0.042 Uiso 1 1 calc R
C7 C 0.3252(3) 0.5902(3) 1.0987(2) 0.0354(6) Uani 1 1 d .
H7A H 0.2285 0.6584 1.1001 0.042 Uiso 1 1 calc R
C11 C 0.6322(4) 0.4731(4) 0.8083(2) 0.0403(7) Uani 1 1 d .
H11A H 0.7003 0.4479 0.7449 0.048 Uiso 1 1 calc R
C1 C 0.1417(3) 0.2522(3) 0.7910(2) 0.0317(6) Uani 1 1 d .
N2 N 0.1799(3) 0.1473(3) 0.7163(2) 0.0464(7) Uani 1 1 d .
H2C H 0.1724 0.1754 0.6522 0.056 Uiso 1 1 calc R
H2D H 0.2123 0.0508 0.7317 0.056 Uiso 1 1 calc R
N3 N 0.1559(3) 0.2088(3) 0.88959(19) 0.0428(6) Uani 1 1 d .
H3B H 0.1326 0.2772 0.9383 0.051 Uiso 1 1 calc R
H3C H 0.1883 0.1122 0.9047 0.051 Uiso 1 1 calc R
N1 N 0.0920(3) 0.4002(3) 0.7682(2) 0.0447(6) Uani 1 1 d .
H1B H 0.0842 0.4290 0.7043 0.054 Uiso 1 1 calc R
H1C H 0.0673 0.4680 0.8173 0.054 Uiso 1 1 calc R
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
O1 S1 O3 112.70(12) . .
O1 S1 O2 112.43(12) . .
O3 S1 O2 112.53(12) . .
O1 S1 C4 107.45(11) . .
O3 S1 C4 105.28(12) . .
O2 S1 C4 105.80(11) . .
C3 C3 C2 119.4(3) 2_666 .
C3 C3 C4 117.9(3) 2_666 .
C2 C3 C4 122.7(2) . .
C5 C4 C3 120.7(2) . .
C5 C4 S1 118.57(18) . .
C3 C4 S1 120.73(18) . .
C4 C5 C6 120.6(2) . .
C4 C5 H5A 119.7 . .
C6 C5 H5A 119.7 . .
C6 C2 C3 120.6(2) 2_666 .
C6 C2 H2B 119.7 2_666 .
C3 C2 H2B 119.7 . .
C2 C6 C5 120.8(2) 2_666 .
C2 C6 H6A 119.6 2_666 .
C5 C6 H6A 119.6 . .
N5 N4 C13 109.6(3) . .
N5 N4 H4A 125.2 . .
C13 N4 H4A 125.2 . .
N4 C13 C14 107.9(3) . .
N4 C13 H13A 126.1 . .
C14 C13 H13A 126.1 . .
N4 N5 C15 109.0(3) . .
N4 N5 H5B 125.5 . .
C15 N5 H5B 125.5 . .
C13 C14 C15 105.4(3) . .
C13 C14 H14A 127.3 . .
C15 C14 H14A 127.3 . .
N5 C15 C14 108.2(3) . .
N5 C15 H15A 125.9 . .
C14 C15 H15A 125.9 . .
O4 S2 O5 112.71(12) . .
O4 S2 O6 113.03(12) . .
O5 S2 O6 111.86(13) . .
O4 S2 C9 107.10(12) . .
O5 S2 C9 106.30(12) . .
O6 S2 C9 105.20(12) . .
C7 C8 C9 123.2(2) . .
C7 C8 C8 118.6(3) . 2_667
C9 C8 C8 118.2(3) . 2_667
C10 C9 C8 121.1(2) . .
C10 C9 S2 117.7(2) . .
C8 C9 S2 121.15(19) . .
C9 C10 C11 120.7(2) . .
C9 C10 H10A 119.7 . .
C11 C10 H10A 119.7 . .
C11 C7 C8 121.4(2) 2_667 .
C11 C7 H7A 119.3 2_667 .
C8 C7 H7A 119.3 . .
C7 C11 C10 120.1(3) 2_667 .
C7 C11 H11A 120.0 2_667 .
C10 C11 H11A 120.0 . .
N1 C1 N2 120.4(3) . .
N1 C1 N3 119.8(3) . .
N2 C1 N3 119.8(3) . .
C1 N2 H2C 120.0 . .
C1 N2 H2D 120.0 . .
H2C N2 H2D 120.0 . .
C1 N3 H3B 120.0 . .
C1 N3 H3C 120.0 . .
H3B N3 H3C 120.0 . .
C1 N1 H1B 120.0 . .
C1 N1 H1C 120.0 . .
H1B N1 H1C 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.4522(19) .
S1 O3 1.4577(18) .
S1 O2 1.4650(19) .
S1 C4 1.787(2) .
C3 C3 1.425(4) 2_666
C3 C2 1.431(3) .
C3 C4 1.440(3) .
C4 C5 1.369(4) .
C5 C6 1.409(3) .
C5 H5A 0.9300 .
C2 C6 1.360(3) 2_666
C2 H2B 0.9300 .
C6 C2 1.360(3) 2_666
C6 H6A 0.9300 .
N4 N5 1.290(4) .
N4 C13 1.297(4) .
N4 H4A 0.8600 .
C13 C14 1.341(5) .
C13 H13A 0.9300 .
N5 C15 1.290(5) .
N5 H5B 0.8600 .
C14 C15 1.354(6) .
C14 H14A 0.9300 .
C15 H15A 0.9300 .
S2 O4 1.452(2) .
S2 O5 1.454(2) .
S2 O6 1.468(2) .
S2 C9 1.789(3) .
C8 C7 1.423(4) .
C8 C9 1.433(3) .
C8 C8 1.434(5) 2_667
C9 C10 1.368(4) .
C10 C11 1.405(4) .
C10 H10A 0.9300 .
C7 C11 1.374(4) 2_667
C7 H7A 0.9300 .
C11 C7 1.374(4) 2_667
C11 H11A 0.9300 .
C1 N1 1.317(3) .
C1 N2 1.321(3) .
C1 N3 1.327(3) .
N2 H2C 0.8600 .
N2 H2D 0.8600 .
N3 H3B 0.8600 .
N3 H3C 0.8600 .
N1 H1B 0.8600 .
N1 H1C 0.8600 .
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
N4 H4A O5 0.86 2.32 3.043(3) 142.0 1_655
N4 H4A O1 0.86 2.37 2.996(4) 130.4 1_655
N4 H4A O3 0.86 2.61 3.075(4) 114.8 1_655
N5 H5B O2 0.86 2.05 2.782(4) 142.6 2_676
N5 H5B O3 0.86 2.48 3.010(4) 120.6 1_655
N2 H2C O2 0.86 2.62 3.217(3) 127.8 2_566
N2 H2D O5 0.86 2.16 2.991(3) 163.1 1_545
N3 H3B O6 0.86 2.21 2.933(3) 141.1 2_567
N3 H3C O4 0.86 2.13 2.969(3) 165.3 1_545
N1 H1B O1 0.86 2.21 2.916(3) 138.6 .
N1 H1C O6 0.86 2.15 2.998(3) 166.8 .
