#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:38:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179670 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/23/4512362.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_4512362
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_sum            'C12 H20 N4 O7 S2'
_chemical_formula_weight         396.44
_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                97.11(3)
_cell_angle_beta                 100.78(3)
_cell_angle_gamma                91.34(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7168(17)
_cell_length_b                   9.1266(18)
_cell_length_c                   11.880(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                     920.2(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9713
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.03
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_interval_time  9
_exptl_absorpt_coefficient_mu    0.330
_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    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0722P)²+0.1454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1587
_reflns_number_gt                2723
_reflns_number_total             4224
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5014895_si_002.cif
_cod_data_source_block           1MA
_cod_depositor_comments
'Adding full bibliography for 4512336--4512373.cif.'
_cod_database_code               4512362
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
H2W H 1.306(6) 0.640(6) -0.053(5) 0.12(2) Uiso 1 1 d .
H1W H 1.369(5) 0.711(5) 0.036(4) 0.073(14) Uiso 1 1 d .
O7 O 1.3867(3) 0.6423(3) -0.0048(3) 0.0637(7) Uani 1 1 d .
C20 C 0.5366(5) 0.5318(5) 0.7465(4) 0.0809(12) Uani 1 1 d .
H20A H 0.4394 0.5792 0.7288 0.121 Uiso 1 1 calc R
H20B H 0.5160 0.4285 0.7485 0.121 Uiso 1 1 calc R
H20C H 0.5972 0.5437 0.6883 0.121 Uiso 1 1 calc R
N4 N 0.6243(3) 0.5997(3) 0.8603(2) 0.0597(8) Uani 1 1 d .
H4A H 0.6657 0.6875 0.8536 0.090 Uiso 1 1 calc R
H4B H 0.7003 0.5415 0.8855 0.090 Uiso 1 1 calc R
H4C H 0.5599 0.6109 0.9103 0.090 Uiso 1 1 calc R
S1 S 0.58524(9) 0.97142(8) 0.79042(6) 0.0440(2) Uani 1 1 d .
S2 S 0.99339(9) 0.50796(8) 0.78996(7) 0.0462(2) Uani 1 1 d .
O6 O 0.7215(2) 0.9056(2) 0.85078(17) 0.0491(5) Uani 1 1 d .
C10 C 0.4928(3) 1.0141(3) 0.5589(2) 0.0332(6) Uani 1 1 d .
C9 C 0.6027(3) 0.9524(3) 0.6427(2) 0.0372(6) Uani 1 1 d .
O2 O 0.8955(3) 0.4142(2) 0.8407(2) 0.0579(6) Uani 1 1 d .
C5 C 1.0203(3) 0.5253(3) 0.5604(2) 0.0396(7) Uani 1 1 d .
O3 O 0.9561(3) 0.6616(2) 0.8076(2) 0.0571(6) Uani 1 1 d .
O4 O 0.5796(3) 1.1276(2) 0.82794(19) 0.0687(7) Uani 1 1 d .
C4 C 0.9506(3) 0.4511(3) 0.6388(3) 0.0417(7) Uani 1 1 d .
O1 O 1.1589(2) 0.4848(3) 0.82769(19) 0.0578(6) Uani 1 1 d .
O5 O 0.4401(3) 0.8896(3) 0.7917(2) 0.0652(7) Uani 1 1 d .
C8 C 0.7208(3) 0.8696(3) 0.6114(3) 0.0464(7) Uani 1 1 d .
H8 H 0.7919 0.8305 0.6671 0.056 Uiso 1 1 calc R
C2 C 0.8072(4) 0.2844(4) 0.4789(3) 0.0627(10) Uani 1 1 d .
H2 H 0.7365 0.2041 0.4524 0.075 Uiso 1 1 calc R
C11 C 0.3693(4) 1.1009(3) 0.5875(3) 0.0465(7) Uani 1 1 d .
H11 H 0.3589 1.1205 0.6644 0.056 Uiso 1 1 calc R
C3 C 0.8466(4) 0.3324(3) 0.5966(3) 0.0540(8) Uani 1 1 d .
H3 H 0.8021 0.2836 0.6478 0.065 Uiso 1 1 calc R
C7 C 0.7336(4) 0.8445(4) 0.4951(3) 0.0558(9) Uani 1 1 d .
H7 H 0.8144 0.7891 0.4741 0.067 Uiso 1 1 calc R
C6 C 1.1294(4) 0.6469(3) 0.5986(3) 0.0496(8) Uani 1 1 d .
H6 H 1.1581 0.6802 0.6771 0.060 Uiso 1 1 calc R
N2 N 0.7650(3) 0.8211(3) 0.1279(2) 0.0506(7) Uani 1 1 d .
H2A H 0.7848 0.7290 0.1235 0.061 Uiso 1 1 calc R
H2B H 0.6730 0.8484 0.1347 0.061 Uiso 1 1 calc R
C1 C 0.8763(4) 0.9214(3) 0.1243(2) 0.0429(7) Uani 1 1 d .
N1 N 0.8450(3) 1.0620(3) 0.1299(2) 0.0537(7) Uani 1 1 d .
H1A H 0.9165 1.1271 0.1267 0.064 Uiso 1 1 calc R
H1B H 0.7529 1.0890 0.1367 0.064 Uiso 1 1 calc R
N3 N 1.0161(3) 0.8789(3) 0.1140(2) 0.0576(7) Uani 1 1 d .
H3A H 1.0883 0.9432 0.1107 0.069 Uiso 1 1 calc R
H3B H 1.0357 0.7867 0.1104 0.069 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
H2W O7 H1W 97(5) . .
N4 C20 H20A 109.5 . .
N4 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
N4 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C20 N4 H4A 109.5 . .
C20 N4 H4B 109.5 . .
H4A N4 H4B 109.5 . .
C20 N4 H4C 109.5 . .
H4A N4 H4C 109.5 . .
H4B N4 H4C 109.5 . .
O4 S1 O6 113.05(14) . .
O4 S1 O5 112.62(16) . .
O6 S1 O5 112.40(14) . .
O4 S1 C9 107.05(14) . .
O6 S1 C9 106.01(13) . .
O5 S1 C9 104.99(13) . .
O3 S2 O2 112.03(14) . .
O3 S2 O1 112.97(14) . .
O2 S2 O1 111.73(14) . .
O3 S2 C4 106.87(14) . .
O2 S2 C4 106.56(14) . .
O1 S2 C4 106.18(14) . .
C11 C10 C10 118.6(3) . 2_676
C11 C10 C9 123.1(3) . .
C10 C10 C9 118.3(3) 2_676 .
C8 C9 C10 121.3(3) . .
C8 C9 S1 117.5(2) . .
C10 C9 S1 121.2(2) . .
C6 C5 C5 118.8(3) . 2_766
C6 C5 C4 122.2(3) . .
C5 C5 C4 119.0(3) 2_766 .
C3 C4 C5 119.6(3) . .
C3 C4 S2 118.5(2) . .
C5 C4 S2 121.9(2) . .
C9 C8 C7 119.5(3) . .
C9 C8 H8 120.2 . .
C7 C8 H8 120.2 . .
C6 C2 C3 121.1(3) 2_766 .
C6 C2 H2 119.5 2_766 .
C3 C2 H2 119.5 . .
C7 C11 C10 121.1(3) 2_676 .
C7 C11 H11 119.4 2_676 .
C10 C11 H11 119.4 . .
C4 C3 C2 120.9(3) . .
C4 C3 H3 119.5 . .
C2 C3 H3 119.5 . .
C11 C7 C8 121.2(3) 2_676 .
C11 C7 H7 119.4 2_676 .
C8 C7 H7 119.4 . .
C2 C6 C5 120.6(3) 2_766 .
C2 C6 H6 119.7 2_766 .
C5 C6 H6 119.7 . .
C1 N2 H2A 120.0 . .
C1 N2 H2B 120.0 . .
H2A N2 H2B 120.0 . .
N3 C1 N1 120.6(3) . .
N3 C1 N2 119.6(3) . .
N1 C1 N2 119.8(3) . .
C1 N1 H1A 120.0 . .
C1 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
C1 N3 H3A 120.0 . .
C1 N3 H3B 120.0 . .
H3A N3 H3B 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O7 H2W 0.82(5) .
O7 H1W 0.79(4) .
C20 N4 1.476(5) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
N4 H4A 0.8900 .
N4 H4B 0.8900 .
N4 H4C 0.8900 .
S1 O4 1.444(2) .
S1 O6 1.452(2) .
S1 O5 1.458(2) .
S1 C9 1.778(3) .
S2 O3 1.446(2) .
S2 O2 1.452(2) .
S2 O1 1.457(2) .
S2 C4 1.773(3) .
C10 C11 1.419(4) .
C10 C10 1.421(5) 2_676
C10 C9 1.426(4) .
C9 C8 1.371(4) .
C5 C6 1.417(4) .
C5 C5 1.426(6) 2_766
C5 C4 1.430(4) .
C4 C3 1.377(4) .
C8 C7 1.398(4) .
C8 H8 0.9300 .
C2 C6 1.364(4) 2_766
C2 C3 1.389(5) .
C2 H2 0.9300 .
C11 C7 1.353(4) 2_676
C11 H11 0.9300 .
C3 H3 0.9300 .
C7 C11 1.353(4) 2_676
C7 H7 0.9300 .
C6 C2 1.364(4) 2_766
C6 H6 0.9300 .
N2 C1 1.328(4) .
N2 H2A 0.8600 .
N2 H2B 0.8600 .
C1 N3 1.310(4) .
C1 N1 1.315(4) .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
N3 H3A 0.8600 .
N3 H3B 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 O6 0.89 2.04 2.920(4) 168.2 .
N4 H4B O2 0.89 2.19 2.967(4) 145.2 .
N4 H4C O7 0.89 1.97 2.852(4) 168.9 1_456
