#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:38:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179670 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/23/4512372.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_4512372
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 H9 N2, C H6 N3, H2 O'
_chemical_formula_sum            'C16 H23 N5 O7 S2'
_chemical_formula_weight         461.51
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.712(4)
_cell_length_b                   13.224(3)
_cell_length_c                   8.1214(16)
_cell_measurement_reflns_used    3638
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     2009.6(7)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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    0.0260
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20352
_diffrn_reflns_theta_full        27.73
_diffrn_reflns_theta_max         27.73
_diffrn_reflns_theta_min         3.08
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_interval_time  9
_exptl_absorpt_coefficient_mu    0.316
_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    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0531
_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)+(0.0563P)²+1.3171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                2031
_reflns_number_total             2459
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5014895_si_002.cif
_cod_data_source_block           11EIM
_cod_depositor_comments
'Adding full bibliography for 4512336--4512373.cif.'
_cod_database_code               4512372
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, 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
N5 N -0.01463(14) 0.7500 0.3060(3) 0.0423(6) Uani 1 2 d S
H5C H -0.0583 0.7500 0.2599 0.051 Uiso 1 2 d SR
N6 N 0.09644(15) 0.7500 0.3335(5) 0.0525(8) Uani 1 2 d S
H6C H 0.1435 0.7500 0.3103 0.063 Uiso 1 2 d SR
C16 C 0.0683(2) 0.7500 0.4867(5) 0.0545(10) Uani 1 2 d S
H16A H 0.0936 0.7500 0.5853 0.065 Uiso 1 2 calc SR
C17 C -0.0014(2) 0.7500 0.4704(4) 0.0471(8) Uani 1 2 d S
H17A H -0.0351 0.7500 0.5547 0.057 Uiso 1 2 calc SR
C18 C 0.04541(18) 0.7500 0.2240(4) 0.0432(8) Uani 1 2 d S
C19 C 0.0561(3) 0.7500 0.0431(5) 0.0722(13) Uani 1 2 d S
H19A H 0.0835 0.6914 0.0140 0.087 Uiso 0.50 1 d PR
C20 C -0.0103(3) 0.7500 -0.0515(5) 0.0898(17) Uani 1 2 d S
H20A H 0.0002 0.7500 -0.1672 0.108 Uiso 1 2 d SR
H20B H -0.0372 0.6907 -0.0251 0.108 Uiso 0.50 1 d PR
N1 N 0.72073(11) 0.33560(16) 0.4136(3) 0.0488(5) Uani 1 1 d .
H1C H 0.7352 0.3943 0.3686 0.059 Uiso 1 1 d R
H1D H 0.6915 0.3360 0.5016 0.059 Uiso 1 1 d R
N2 N 0.78422(17) 0.2500 0.2224(4) 0.0529(8) Uani 1 2 d S
H2C H 0.7987 0.1911 0.1783 0.063 Uiso 0.50 1 d PR
C21 C 0.74193(15) 0.2500 0.3500(4) 0.0345(6) Uani 1 2 d S
H3B H 0.7990 0.1911 0.1777 0.041 Uiso 0.50 1 d PR
S1 S 0.84837(3) 0.52983(4) 0.27188(7) 0.0403(2) Uani 1 1 d .
O4 O 0.87017(10) 0.62153(14) 0.1913(2) 0.0614(6) Uani 1 1 d .
O5 O 0.77669(9) 0.53622(14) 0.3353(2) 0.0537(5) Uani 1 1 d .
O6 O 0.85912(10) 0.44204(16) 0.1717(2) 0.0583(5) Uani 1 1 d .
C1 C 1.08493(14) 0.4911(2) 0.2624(3) 0.0457(6) Uani 1 1 d .
H1A H 1.1067 0.4900 0.1594 0.055 Uiso 1 1 calc R
C2 C 1.01333(13) 0.50201(18) 0.2735(3) 0.0385(5) Uani 1 1 d .
H2A H 0.9862 0.5077 0.1779 0.046 Uiso 1 1 calc R
C3 C 0.97930(11) 0.50475(15) 0.4273(2) 0.0299(4) Uani 1 1 d .
C4 C 0.90460(11) 0.51698(15) 0.4459(3) 0.0326(4) Uani 1 1 d .
C5 C 0.87369(12) 0.51837(18) 0.5967(3) 0.0421(5) Uani 1 1 d .
H5B H 0.8244 0.5257 0.6058 0.051 Uiso 1 1 calc R
O8 O 0.27384(15) 0.2500 0.6924(5) 0.0835(10) Uani 1 2 d S
H8 H 0.2536 0.3035 0.6761 0.125 Uiso 1 1 d 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
C18 N5 C17 110.2(3) . .
C18 N5 H5C 124.7 . .
C17 N5 H5C 125.1 . .
C18 N6 C16 110.0(3) . .
C18 N6 H6C 125.0 . .
C16 N6 H6C 125.0 . .
C17 C16 N6 107.2(3) . .
C17 C16 H16A 126.4 . .
N6 C16 H16A 126.4 . .
C16 C17 N5 106.3(3) . .
C16 C17 H17A 126.9 . .
N5 C17 H17A 126.9 . .
N6 C18 N5 106.4(3) . .
N6 C18 C19 125.2(4) . .
N5 C18 C19 128.4(3) . .
C20 C19 C18 114.0(4) . .
C20 C19 H19A 109.0 . .
C18 C19 H19A 108.5 . .
C19 C20 H20A 109.9 . .
C19 C20 H20B 109.2 . .
H20A C20 H20B 109.2 . .
C21 N1 H1C 119.7 . .
C21 N1 H1D 120.3 . .
H1C N1 H1D 120.0 . .
C21 N2 H2C 120.0 . .
C21 N2 H3B 120.3 . .
H2C N2 H3B 0.4 . .
N1 C21 N1 120.2(3) 8_565 .
N1 C21 N2 119.91(14) 8_565 .
N1 C21 N2 119.91(14) . .
O6 S1 O4 112.67(13) . .
O6 S1 O5 112.45(11) . .
O4 S1 O5 112.21(12) . .
O6 S1 C4 106.99(11) . .
O4 S1 C4 106.02(10) . .
O5 S1 C4 105.90(11) . .
C2 C1 C5 120.5(2) . 5_766
C2 C1 H1A 119.7 . .
C5 C1 H1A 119.7 5_766 .
C1 C2 C3 120.8(2) . .
C1 C2 H2A 119.6 . .
C3 C2 H2A 119.6 . .
C2 C3 C4 123.11(19) . .
C2 C3 C3 119.4(2) . 5_766
C4 C3 C3 117.5(2) . 5_766
C5 C4 C3 121.31(19) . .
C5 C4 S1 117.82(17) . .
C3 C4 S1 120.86(16) . .
C4 C5 C1 120.4(2) . 5_766
C4 C5 H5B 119.8 . .
C1 C5 H5B 119.8 5_766 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N5 C18 1.306(4) .
N5 C17 1.358(4) .
N5 H5C 0.8993 .
N6 C18 1.304(5) .
N6 C16 1.352(5) .
N6 H6C 0.9001 .
C16 C17 1.310(5) .
C16 H16A 0.9300 .
C17 H17A 0.9300 .
C18 C19 1.483(5) .
C19 C20 1.461(7) .
C19 H19A 0.9589 .
C20 H20A 0.9598 .
C20 H20B 0.9563 .
N1 C21 1.306(2) .
N1 H1C 0.8999 .
N1 H1D 0.9003 .
N2 C21 1.304(4) .
N2 H2C 0.8991 .
N2 H3B 0.9024 .
C21 N1 1.306(2) 8_565
S1 O6 1.432(2) .
S1 O4 1.4372(17) .
S1 O5 1.4392(19) .
S1 C4 1.770(2) .
C1 C2 1.350(3) .
C1 C5 1.388(3) 5_766
C1 H1A 0.9300 .
C2 C3 1.403(3) .
C2 H2A 0.9300 .
C3 C4 1.415(3) .
C3 C3 1.418(4) 5_766
C4 C5 1.354(3) .
C5 C1 1.388(3) 5_766
C5 H5B 0.9300 .
O8 H8 0.8134 .
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
N5 H5C O4 0.90 2.23 2.899(3) 130.4 1_455
N5 H5C O4 0.90 2.23 2.899(3) 130.4 8_475
N6 H6C O8 0.90 1.82 2.684(4) 160.3 2_564
N1 H1C O5 0.90 2.05 2.922(3) 163.3 .
N1 H1D O4 0.90 2.00 2.881(3) 164.1 2_665
N2 H2C O6 0.90 2.09 2.930(3) 154.4 8_565
N2 H2C O6 0.90 2.09 2.930(3) 154.4 8_565
O8 H8 O5 0.81 2.20 2.989(2) 165.1 5_666
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_site_symmetry_1
_geom_torsion_site_symmetry_4
C18 N6 C16 C17 0.0 . .
N6 C16 C17 N5 0.0 . .
C18 N5 C17 C16 0.0 . .
C16 N6 C18 N5 0.0 . .
C16 N6 C18 C19 180.0 . .
C17 N5 C18 N6 0.0 . .
C17 N5 C18 C19 180.0 . .
N6 C18 C19 C20 180.0 . .
N5 C18 C19 C20 0.0 . .
C5 C1 C2 C3 0.5(4) 5_766 .
C1 C2 C3 C4 179.4(2) . .
C1 C2 C3 C3 -0.5(4) . 5_766
C2 C3 C4 C5 179.4(2) . .
C3 C3 C4 C5 -0.8(4) 5_766 .
C2 C3 C4 S1 0.0(3) . .
C3 C3 C4 S1 179.83(19) 5_766 .
O6 S1 C4 C5 -122.01(19) . .
O4 S1 C4 C5 117.5(2) . .
O5 S1 C4 C5 -1.9(2) . .
O6 S1 C4 C3 57.4(2) . .
O4 S1 C4 C3 -63.0(2) . .
O5 S1 C4 C3 177.58(17) . .
C3 C4 C5 C1 0.7(4) . 5_766
S1 C4 C5 C1 -179.8(2) . 5_766
