#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:38:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179670 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/23/4512359.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_4512359
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                92.266(5)
_cell_angle_beta                 101.980(8)
_cell_angle_gamma                90.041(6)
_cell_formula_units_Z            2
_cell_length_a                   8.059(4)
_cell_length_b                   8.213(4)
_cell_length_c                   14.116(7)
_cell_measurement_reflns_used    2236
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.4932
_cell_measurement_theta_min      2.4820
_cell_volume                     913.2(8)
_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      273(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0384
_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            9993
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.58
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 180
_diffrn_standards_interval_time  9
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.336
_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    1.551
_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         0.319
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0452
_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)+(0.0799P)²+0.0337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                3199
_reflns_number_total             4187
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5014895_si_003.cif
_cod_data_source_block           24-273K
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4512336--4512373.cif.
;
_cod_database_code               4512359
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 0.2152(4) 0.6901(4) 0.2624(3) 0.0683(9) Uani 1 1 d .
H1 H 0.2798 0.5961 0.2632 0.082 Uiso 1 1 calc R
C2 C 0.1687(5) 0.7684(5) 0.1806(2) 0.0724(10) Uani 1 1 d .
H2 H 0.1998 0.7294 0.1241 0.087 Uiso 1 1 calc R
C3 C 0.0745(5) 0.9072(5) 0.1806(2) 0.0720(10) Uani 1 1 d .
H3 H 0.0381 0.9623 0.1238 0.086 Uiso 1 1 calc R
C4 C 0.0347(4) 0.9637(4) 0.2663(3) 0.0606(8) Uani 1 1 d .
H4 H -0.0257 1.0597 0.2686 0.073 Uiso 1 1 calc R
C5 C 0.0835(3) 0.8793(3) 0.34555(18) 0.0465(6) Uani 1 1 d .
H5 H 0.0558 0.9163 0.4034 0.056 Uiso 1 1 calc R
C6 C 0.3895(3) 0.2020(3) 0.48009(15) 0.0290(4) Uani 1 1 d .
C7 C 0.4923(3) 0.2801(3) 0.43008(16) 0.0353(5) Uani 1 1 d .
H7 H 0.4674 0.3855 0.4102 0.042 Uiso 1 1 calc R
C8 C 0.3642(3) -0.2010(3) 0.59118(17) 0.0391(5) Uani 1 1 d .
H8 H 0.2939 -0.2561 0.6239 0.047 Uiso 1 1 calc R
C9 C 0.3263(3) -0.0462(3) 0.56495(16) 0.0334(5) Uani 1 1 d .
H9 H 0.2326 0.0043 0.5817 0.040 Uiso 1 1 calc R
C10 C 0.4280(2) 0.0399(2) 0.51200(14) 0.0262(4) Uani 1 1 d .
C11 C 0.4094(3) 0.1267(2) 0.08999(15) 0.0292(5) Uani 1 1 d .
C12 C 0.4765(3) 0.0524(3) 0.17420(16) 0.0372(5) Uani 1 1 d .
H12 H 0.4508 0.0915 0.2321 0.045 Uiso 1 1 calc R
C13 C 0.5842(3) -0.0828(3) 0.17431(17) 0.0397(5) Uani 1 1 d .
H13 H 0.6295 -0.1321 0.2321 0.048 Uiso 1 1 calc R
C14 C 0.3781(3) 0.1412(3) -0.08961(16) 0.0354(5) Uani 1 1 d .
H14 H 0.3068 0.2303 -0.0903 0.042 Uiso 1 1 calc R
C15 C 0.4453(3) 0.0686(2) -0.00054(15) 0.0289(4) Uani 1 1 d .
C16 C 0.1884(3) 0.5782(3) 0.81080(16) 0.0327(5) Uani 1 1 d .
N1 N 0.1696(3) 0.7456(3) 0.34335(19) 0.0610(7) Uani 1 1 d .
H1A H 0.1977 0.6918 0.3952 0.073 Uiso 1 1 calc R
N2 N 0.0547(3) 0.6079(3) 0.74226(15) 0.0450(5) Uani 1 1 d .
H2A H 0.0555 0.5820 0.6827 0.054 Uiso 1 1 calc R
H2B H -0.0331 0.6531 0.7572 0.054 Uiso 1 1 calc R
N3 N 0.1885(3) 0.6240(3) 0.90180(14) 0.0447(5) Uani 1 1 d .
H3A H 0.2767 0.6086 0.9465 0.054 Uiso 1 1 calc R
H3B H 0.1002 0.6692 0.9162 0.054 Uiso 1 1 calc R
N4 N 0.3228(2) 0.5092(2) 0.78848(14) 0.0410(5) Uani 1 1 d .
H4A H 0.3240 0.4832 0.7290 0.049 Uiso 1 1 calc R
H4B H 0.4097 0.4900 0.8333 0.049 Uiso 1 1 calc R
O1 O 0.2388(3) 0.3354(2) 0.60860(12) 0.0528(5) Uani 1 1 d .
O2 O 0.0634(2) 0.2017(2) 0.46820(14) 0.0507(5) Uani 1 1 d .
O3 O 0.2004(3) 0.4560(2) 0.45190(14) 0.0535(5) Uani 1 1 d .
O4 O 0.1143(2) 0.2596(2) 0.03263(12) 0.0453(4) Uani 1 1 d .
O5 O 0.2619(2) 0.3153(2) 0.19799(11) 0.0430(4) Uani 1 1 d .
O6 O 0.3628(2) 0.43633(19) 0.06656(12) 0.0405(4) Uani 1 1 d .
S1 S 0.20839(7) 0.30820(7) 0.50409(4) 0.03436(18) Uani 1 1 d .
S2 S 0.27577(7) 0.29724(7) 0.09723(4) 0.03297(17) 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
C2 C1 N1 120.3(3) . .
C2 C1 H1 119.9 . .
N1 C1 H1 119.9 . .
C1 C2 C3 119.2(3) . .
C1 C2 H2 120.4 . .
C3 C2 H2 120.4 . .
C2 C3 C4 118.8(3) . .
C2 C3 H3 120.6 . .
C4 C3 H3 120.6 . .
C5 C4 C3 119.2(3) . .
C5 C4 H4 120.4 . .
C3 C4 H4 120.4 . .
N1 C5 C4 120.9(3) . .
N1 C5 H5 119.5 . .
C4 C5 H5 119.5 . .
C7 C6 C10 120.4(2) . .
C7 C6 S1 117.91(17) . .
C10 C6 S1 121.70(16) . .
C6 C7 C8 120.0(2) . 2_656
C6 C7 H7 120.0 . .
C8 C7 H7 120.0 2_656 .
C9 C8 C7 121.4(2) . 2_656
C9 C8 H8 119.3 . .
C7 C8 H8 119.3 2_656 .
C8 C9 C10 120.8(2) . .
C8 C9 H9 119.6 . .
C10 C9 H9 119.6 . .
C9 C10 C10 118.5(2) . 2_656
C9 C10 C6 122.66(19) . .
C10 C10 C6 118.9(2) 2_656 .
C12 C11 C15 120.9(2) . .
C12 C11 S2 117.57(16) . .
C15 C11 S2 121.48(16) . .
C11 C12 C13 120.8(2) . .
C11 C12 H12 119.6 . .
C13 C12 H12 119.6 . .
C14 C13 C12 119.9(2) 2_655 .
C14 C13 H13 120.1 2_655 .
C12 C13 H13 120.1 . .
C13 C14 C15 121.2(2) 2_655 .
C13 C14 H14 119.4 2_655 .
C15 C14 H14 119.4 . .
C14 C15 C15 119.4(2) . 2_655
C14 C15 C11 122.93(19) . .
C15 C15 C11 117.7(2) 2_655 .
N4 C16 N2 120.2(2) . .
N4 C16 N3 120.2(2) . .
N2 C16 N3 119.5(2) . .
C5 N1 C1 121.5(3) . .
C5 N1 H1A 119.2 . .
C1 N1 H1A 119.2 . .
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 . .
O3 S1 O2 112.49(12) . .
O3 S1 O1 113.64(11) . .
O2 S1 O1 112.00(12) . .
O3 S1 C6 105.70(11) . .
O2 S1 C6 106.32(10) . .
O1 S1 C6 105.96(11) . .
O4 S2 O5 112.68(11) . .
O4 S2 O6 112.63(11) . .
O5 S2 O6 112.19(10) . .
O4 S2 C11 106.90(10) . .
O5 S2 C11 106.06(10) . .
O6 S2 C11 105.76(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.329(5) .
C1 N1 1.335(4) .
C1 H1 0.9300 .
C2 C3 1.371(5) .
C2 H2 0.9300 .
C3 C4 1.377(5) .
C3 H3 0.9300 .
C4 C5 1.329(4) .
C4 H4 0.9300 .
C5 N1 1.302(4) .
C5 H5 0.9300 .
C6 C7 1.370(3) .
C6 C10 1.435(3) .
C6 S1 1.786(2) .
C7 C8 1.407(3) 2_656
C7 H7 0.9300 .
C8 C9 1.355(3) .
C8 C7 1.407(3) 2_656
C8 H8 0.9300 .
C9 C10 1.424(3) .
C9 H9 0.9300 .
C10 C10 1.427(4) 2_656
C11 C12 1.367(3) .
C11 C15 1.432(3) .
C11 S2 1.780(2) .
C12 C13 1.410(3) .
C12 H12 0.9300 .
C13 C14 1.363(3) 2_655
C13 H13 0.9300 .
C14 C13 1.363(3) 2_655
C14 C15 1.417(3) .
C14 H14 0.9300 .
C15 C15 1.429(4) 2_655
C16 N4 1.312(3) .
C16 N2 1.320(3) .
C16 N3 1.324(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 S1 1.4527(18) .
O2 S1 1.4510(19) .
O3 S1 1.4394(19) .
O4 S2 1.4508(18) .
O5 S2 1.4515(17) .
O6 S2 1.4658(17) .
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 O3 0.86 2.12 2.863(3) 143.9 .
N4 H4A O1 0.86 2.05 2.818(3) 149.0 .
N2 H2A O3 0.86 2.51 3.092(3) 126.0 2_566
N2 H2B O5 0.86 2.08 2.911(3) 161.4 2_566
N3 H3A O6 0.86 2.25 2.948(3) 138.3 1_556
N3 H3B O4 0.86 2.08 2.932(3) 169.1 2_566
N3 H3B S2 0.86 3.01 3.800(3) 153.7 2_566
N4 H4B O6 0.86 2.14 2.929(3) 152.3 2_666
