#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:38:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179670 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/23/4512342.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_4512342
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                92.211(10)
_cell_angle_beta                 99.516(16)
_cell_angle_gamma                90.523(14)
_cell_formula_units_Z            2
_cell_length_a                   7.981(6)
_cell_length_b                   8.136(7)
_cell_length_c                   14.060(12)
_cell_measurement_reflns_used    2353
_cell_measurement_temperature    188(2)
_cell_measurement_theta_max      27.5865
_cell_measurement_theta_min      2.5057
_cell_volume                     899.6(13)
_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      188(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  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0683
_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            9618
_diffrn_reflns_theta_full        27.39
_diffrn_reflns_theta_max         27.39
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 180
_diffrn_standards_interval_time  9
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.341
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.575
_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         0.391
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0469
_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)+(0.0596P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                2956
_reflns_number_total             4108
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5014895_si_003.cif
_cod_data_source_block           7-188K
_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               4512342
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 0.8227(3) 0.2209(3) 0.6520(2) 0.0343(6) Uani 1 1 d .
H1A H 0.7852 0.2645 0.5922 0.041 Uiso 1 1 calc R
C2 C 0.7915(4) 0.3001(3) 0.7341(2) 0.0365(7) Uani 1 1 d .
H2A H 0.7293 0.3964 0.7308 0.044 Uiso 1 1 calc R
C3 C 0.8524(4) 0.2368(4) 0.8215(2) 0.0401(7) Uani 1 1 d .
H3A H 0.8328 0.2907 0.8781 0.048 Uiso 1 1 calc R
C4 C 0.9432(4) 0.0929(4) 0.8257(2) 0.0407(7) Uani 1 1 d .
H4A H 0.9868 0.0498 0.8849 0.049 Uiso 1 1 calc R
C5 C 0.9676(3) 0.0152(3) 0.7417(2) 0.0371(7) Uani 1 1 d .
H5A H 1.0263 -0.0831 0.7430 0.045 Uiso 1 1 calc R
C6 C 0.5967(3) 0.8721(3) 0.90940(17) 0.0218(5) Uani 1 1 d .
C7 C 0.5343(3) 0.9469(3) 0.82559(17) 0.0255(5) Uani 1 1 d .
H7A H 0.5633 0.9076 0.7676 0.031 Uiso 1 1 calc R
C8 C 0.4268(3) 1.0827(3) 0.82645(17) 0.0274(6) Uani 1 1 d .
H8A H 0.3853 1.1326 0.7691 0.033 Uiso 1 1 calc R
C9 C 0.6170(3) 0.8582(3) 1.08876(17) 0.0251(5) Uani 1 1 d .
H9A H 0.6889 0.7688 1.0893 0.030 Uiso 1 1 calc R
C10 C 0.5549(3) 0.9307(3) 1.00019(16) 0.0214(5) Uani 1 1 d .
C11 C 0.6137(3) 0.7996(3) 0.52007(16) 0.0196(5) Uani 1 1 d .
C12 C 0.5126(3) 0.7205(3) 0.57416(17) 0.0249(5) Uani 1 1 d .
H12A H 0.5396 0.6153 0.5948 0.030 Uiso 1 1 calc R
C13 C 0.3676(3) 0.7983(3) 0.59857(17) 0.0262(5) Uani 1 1 d .
H13A H 0.2978 0.7425 0.6338 0.031 Uiso 1 1 calc R
C14 C 0.6716(3) 1.0471(3) 0.42840(16) 0.0225(5) Uani 1 1 d .
H14A H 0.7649 0.9964 0.4088 0.027 Uiso 1 1 calc R
C15 C 0.5728(3) 0.9607(3) 0.48629(15) 0.0186(5) Uani 1 1 d .
C16 C 1.2013(3) 0.5688(3) 0.80772(16) 0.0221(5) Uani 1 1 d .
N1 N 0.9075(3) 0.0800(3) 0.65803(16) 0.0362(6) Uani 1 1 d .
H1B H 0.9238 0.0294 0.6056 0.043 Uiso 1 1 calc R
N2 N 1.3396(3) 0.4983(2) 0.78575(14) 0.0260(5) Uani 1 1 d .
H2B H 1.3433 0.4666 0.7271 0.031 Uiso 1 1 calc R
H2C H 1.4256 0.4841 0.8301 0.031 Uiso 1 1 calc R
N3 N 1.1976(3) 0.6221(3) 0.89779(14) 0.0313(5) Uani 1 1 d .
H3B H 1.2849 0.6108 0.9418 0.038 Uiso 1 1 calc R
H3C H 1.1079 0.6680 0.9121 0.038 Uiso 1 1 calc R
N4 N 1.0689(3) 0.5907(3) 0.73950(14) 0.0278(5) Uani 1 1 d .
H4B H 1.0725 0.5591 0.6808 0.033 Uiso 1 1 calc R
H4C H 0.9791 0.6365 0.7538 0.033 Uiso 1 1 calc R
O1 O 0.6390(2) 0.5597(2) 0.93290(12) 0.0268(4) Uani 1 1 d .
O2 O 0.8905(2) 0.7374(2) 0.96610(12) 0.0312(4) Uani 1 1 d .
O3 O 0.7510(2) 0.6818(2) 0.80131(12) 0.0284(4) Uani 1 1 d .
O4 O 0.8149(2) 0.5514(2) 0.55117(13) 0.0317(4) Uani 1 1 d .
O5 O 0.9416(2) 0.8175(2) 0.52962(12) 0.0263(4) Uani 1 1 d .
O6 O 0.7790(2) 0.6676(2) 0.39218(12) 0.0318(4) Uani 1 1 d .
S1 S 0.73089(7) 0.69985(7) 0.90217(4) 0.02252(16) Uani 1 1 d .
S2 S 0.80223(7) 0.69849(7) 0.49664(4) 0.02167(16) 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 119.4(3) . .
N1 C1 H1A 120.3 . .
C2 C1 H1A 120.3 . .
C1 C2 C3 119.4(3) . .
C1 C2 H2A 120.3 . .
C3 C2 H2A 120.3 . .
C2 C3 C4 119.9(3) . .
C2 C3 H3A 120.0 . .
C4 C3 H3A 120.0 . .
C5 C4 C3 118.8(3) . .
C5 C4 H4A 120.6 . .
C3 C4 H4A 120.6 . .
N1 C5 C4 119.9(3) . .
N1 C5 H5A 120.1 . .
C4 C5 H5A 120.1 . .
C7 C6 C10 121.0(2) . .
C7 C6 S1 117.87(18) . .
C10 C6 S1 121.17(18) . .
C6 C7 C8 120.6(2) . .
C6 C7 H7A 119.7 . .
C8 C7 H7A 119.7 . .
C9 C8 C7 120.4(2) 2_677 .
C9 C8 H8A 119.8 2_677 .
C7 C8 H8A 119.8 . .
C8 C9 C10 121.2(2) 2_677 .
C8 C9 H9A 119.4 2_677 .
C10 C9 H9A 119.4 . .
C9 C10 C10 119.2(3) . 2_677
C9 C10 C6 123.1(2) . .
C10 C10 C6 117.8(3) 2_677 .
C12 C11 C15 120.8(2) . .
C12 C11 S2 117.94(18) . .
C15 C11 S2 121.22(17) . .
C11 C12 C13 120.1(2) . .
C11 C12 H12A 120.0 . .
C13 C12 H12A 120.0 . .
C14 C13 C12 121.0(2) 2_676 .
C14 C13 H13A 119.5 2_676 .
C12 C13 H13A 119.5 . .
C13 C14 C15 121.2(2) 2_676 .
C13 C14 H14A 119.4 2_676 .
C15 C14 H14A 119.4 . .
C14 C15 C15 118.6(3) . 2_676
C14 C15 C11 123.1(2) . .
C15 C15 C11 118.3(3) 2_676 .
N2 C16 N4 120.1(2) . .
N2 C16 N3 119.9(2) . .
N4 C16 N3 120.0(2) . .
C5 N1 C1 122.6(2) . .
C5 N1 H1B 118.7 . .
C1 N1 H1B 118.7 . .
C16 N2 H2B 120.0 . .
C16 N2 H2C 120.0 . .
H2B N2 H2C 120.0 . .
C16 N3 H3B 120.0 . .
C16 N3 H3C 120.0 . .
H3B N3 H3C 120.0 . .
C16 N4 H4B 120.0 . .
C16 N4 H4C 120.0 . .
H4B N4 H4C 120.0 . .
O2 S1 O3 112.70(12) . .
O2 S1 O1 112.76(11) . .
O3 S1 O1 112.15(11) . .
O2 S1 C6 107.31(11) . .
O3 S1 C6 105.71(10) . .
O1 S1 C6 105.54(12) . .
O4 S2 O6 114.05(11) . .
O4 S2 O5 113.20(11) . .
O6 S2 O5 111.35(11) . .
O4 S2 C11 106.30(11) . .
O6 S2 C11 105.95(11) . .
O5 S2 C11 105.19(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.335(3) .
C1 C2 1.361(4) .
C1 H1A 0.9300 .
C2 C3 1.366(4) .
C2 H2A 0.9300 .
C3 C4 1.380(4) .
C3 H3A 0.9300 .
C4 C5 1.362(4) .
C4 H4A 0.9300 .
C5 N1 1.326(4) .
C5 H5A 0.9300 .
C6 C7 1.369(3) .
C6 C10 1.437(3) .
C6 S1 1.781(3) .
C7 C8 1.405(3) .
C7 H7A 0.9300 .
C8 C9 1.368(3) 2_677
C8 H8A 0.9300 .
C9 C8 1.368(3) 2_677
C9 C10 1.415(3) .
C9 H9A 0.9300 .
C10 C10 1.434(4) 2_677
C11 C12 1.369(3) .
C11 C15 1.433(3) .
C11 S2 1.793(3) .
C12 C13 1.409(3) .
C12 H12A 0.9300 .
C13 C14 1.352(3) 2_676
C13 H13A 0.9300 .
C14 C13 1.352(3) 2_676
C14 C15 1.423(3) .
C14 H14A 0.9300 .
C15 C15 1.432(4) 2_676
C16 N2 1.324(3) .
C16 N4 1.323(3) .
C16 N3 1.328(3) .
N1 H1B 0.8600 .
N2 H2B 0.8600 .
N2 H2C 0.8600 .
N3 H3B 0.8600 .
N3 H3C 0.8600 .
N4 H4B 0.8600 .
N4 H4C 0.8600 .
O1 S1 1.4667(19) .
O2 S1 1.4551(19) .
O3 S1 1.455(2) .
O4 S2 1.441(2) .
O5 S2 1.4712(19) .
O6 S2 1.461(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
N3 H3C O2 0.86 2.08 2.925(3) 167.8 .
N3 H3C S1 0.86 3.00 3.794(4) 153.9 .
N4 H4B O4 0.86 2.51 3.061(3) 122.6 .
N4 H4C O3 0.86 2.07 2.908(3) 163.9 .
N1 H1B O5 0.86 2.01 2.788(3) 149.7 1_545
N2 H2B O6 0.86 2.06 2.812(3) 145.2 2_766
N2 H2C O1 0.86 2.11 2.917(3) 155.2 1_655
N2 H2C S1 0.86 3.00 3.624(3) 130.9 1_655
N3 H3B O1 0.86 2.29 2.973(3) 136.3 2_767
N4 H4B O6 0.86 2.48 3.131(3) 133.1 2_766
