#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:38:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179670 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/23/4512343.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_4512343
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                92.224(15)
_cell_angle_beta                 99.586(18)
_cell_angle_gamma                90.53(2)
_cell_formula_units_Z            2
_cell_length_a                   8.000(6)
_cell_length_b                   8.152(7)
_cell_length_c                   14.090(11)
_cell_measurement_reflns_used    2427
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.6373
_cell_measurement_theta_min      2.5007
_cell_volume                     905.3(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      193(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  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0717
_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            9738
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 180
_diffrn_standards_interval_time  9
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.339
_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    1.565
_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         0.398
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0447
_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)+(0.0636P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                2900
_reflns_number_total             4139
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5014895_si_003.cif
_cod_data_source_block           8-193K
_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               4512343
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 0.8224(4) 0.2220(3) 0.6519(2) 0.0352(7) Uani 1 1 d .
H1A H 0.7851 0.2662 0.5924 0.042 Uiso 1 1 calc R
C2 C 0.7911(4) 0.2999(3) 0.7345(2) 0.0381(7) Uani 1 1 d .
H2A H 0.7289 0.3959 0.7316 0.046 Uiso 1 1 calc R
C3 C 0.8516(4) 0.2363(4) 0.8214(2) 0.0416(8) Uani 1 1 d .
H3A H 0.8315 0.2894 0.8779 0.050 Uiso 1 1 calc R
C4 C 0.9429(4) 0.0930(4) 0.8255(2) 0.0420(7) Uani 1 1 d .
H4A H 0.9865 0.0501 0.8846 0.050 Uiso 1 1 calc R
C5 C 0.9680(4) 0.0154(3) 0.7417(2) 0.0384(7) Uani 1 1 d .
H5A H 1.0268 -0.0826 0.7430 0.046 Uiso 1 1 calc R
C6 C 0.5964(3) 0.8722(3) 0.90928(17) 0.0218(5) Uani 1 1 d .
C7 C 0.5340(3) 0.9466(3) 0.82557(17) 0.0259(6) Uani 1 1 d .
H7A H 0.5629 0.9074 0.7677 0.031 Uiso 1 1 calc R
C8 C 0.4261(3) 1.0825(3) 0.82643(18) 0.0283(6) Uani 1 1 d .
H8A H 0.3841 1.1319 0.7691 0.034 Uiso 1 1 calc R
C9 C 0.6171(3) 0.8579(3) 1.08865(18) 0.0250(5) Uani 1 1 d .
H9A H 0.6882 0.7682 1.0891 0.030 Uiso 1 1 calc R
C10 C 0.5549(3) 0.9310(3) 1.00005(17) 0.0216(5) Uani 1 1 d .
C11 C 0.6142(3) 0.7996(3) 0.52012(16) 0.0200(5) Uani 1 1 d .
C12 C 0.5129(3) 0.7201(3) 0.57410(18) 0.0250(5) Uani 1 1 d .
H12A H 0.5398 0.6151 0.5947 0.030 Uiso 1 1 calc R
C13 C 0.3677(3) 0.7982(3) 0.59816(18) 0.0271(6) Uani 1 1 d .
H13A H 0.2979 0.7426 0.6331 0.033 Uiso 1 1 calc R
C14 C 0.6716(3) 1.0476(3) 0.42876(17) 0.0230(5) Uani 1 1 d .
H14A H 0.7647 0.9971 0.4093 0.028 Uiso 1 1 calc R
C15 C 0.5727(3) 0.9608(3) 0.48648(16) 0.0187(5) Uani 1 1 d .
C16 C 0.2005(3) 0.5695(3) 0.80777(17) 0.0223(5) Uani 1 1 d .
N1 N 0.9076(3) 0.0809(3) 0.65773(17) 0.0361(6) Uani 1 1 d .
H1B H 0.9240 0.0307 0.6053 0.043 Uiso 1 1 calc R
N2 N 0.3392(3) 0.4985(2) 0.78587(15) 0.0269(5) Uani 1 1 d .
H2B H 0.3430 0.4669 0.7273 0.032 Uiso 1 1 calc R
H2C H 0.4250 0.4843 0.8303 0.032 Uiso 1 1 calc R
N3 N 0.0684(3) 0.5914(3) 0.73946(15) 0.0286(5) Uani 1 1 d .
H3B H 0.0721 0.5598 0.6809 0.034 Uiso 1 1 calc R
H3C H -0.0212 0.6373 0.7537 0.034 Uiso 1 1 calc R
N4 N 0.1973(3) 0.6225(3) 0.89805(15) 0.0321(5) Uani 1 1 d .
H4B H 0.1092 0.6711 0.9122 0.038 Uiso 1 1 calc R
H4C H 0.2833 0.6080 0.9422 0.038 Uiso 1 1 calc R
O1 O 0.7504(2) 0.6820(2) 0.80151(12) 0.0292(4) Uani 1 1 d .
O2 O 0.6392(2) 0.5595(2) 0.93290(12) 0.0277(4) Uani 1 1 d .
O3 O 0.8902(2) 0.7377(2) 0.96618(13) 0.0306(4) Uani 1 1 d .
O4 O 0.7788(2) 0.6676(2) 0.39207(12) 0.0325(5) Uani 1 1 d .
O5 O 0.8148(2) 0.5512(2) 0.55104(13) 0.0325(4) Uani 1 1 d .
O6 O 0.9414(2) 0.8175(2) 0.52939(13) 0.0275(4) Uani 1 1 d .
S1 S 0.73073(8) 0.70003(7) 0.90226(4) 0.02276(17) Uani 1 1 d .
S2 S 0.80216(8) 0.69853(7) 0.49656(4) 0.02198(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
N1 C1 C2 119.1(3) . .
N1 C1 H1A 120.4 . .
C2 C1 H1A 120.4 . .
C3 C2 C1 119.7(3) . .
C3 C2 H2A 120.2 . .
C1 C2 H2A 120.2 . .
C2 C3 C4 120.0(3) . .
C2 C3 H3A 120.0 . .
C4 C3 H3A 120.0 . .
C5 C4 C3 119.0(3) . .
C5 C4 H4A 120.5 . .
C3 C4 H4A 120.5 . .
N1 C5 C4 119.6(3) . .
N1 C5 H5A 120.2 . .
C4 C5 H5A 120.2 . .
C7 C6 C10 121.0(2) . .
C7 C6 S1 117.90(19) . .
C10 C6 S1 121.12(18) . .
C6 C7 C8 120.5(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 121.0(2) 2_677 .
C8 C9 H9A 119.5 2_677 .
C10 C9 H9A 119.5 . .
C9 C10 C10 119.1(3) . 2_677
C9 C10 C6 122.9(2) . .
C10 C10 C6 118.0(3) 2_677 .
C12 C11 C15 120.7(2) . .
C12 C11 S2 117.88(19) . .
C15 C11 S2 121.41(18) . .
C11 C12 C13 119.8(2) . .
C11 C12 H12A 120.1 . .
C13 C12 H12A 120.1 . .
C14 C13 C12 121.2(2) 2_676 .
C14 C13 H13A 119.4 2_676 .
C12 C13 H13A 119.4 . .
C13 C14 C15 121.2(2) 2_676 .
C13 C14 H14A 119.4 2_676 .
C15 C14 H14A 119.4 . .
C14 C15 C15 118.4(3) . 2_676
C14 C15 C11 123.0(2) . .
C15 C15 C11 118.6(3) 2_676 .
N3 C16 N2 120.1(2) . .
N3 C16 N4 120.2(2) . .
N2 C16 N4 119.7(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 . .
O3 S1 O1 112.79(12) . .
O3 S1 O2 112.74(12) . .
O1 S1 O2 112.06(11) . .
O3 S1 C6 107.34(11) . .
O1 S1 C6 105.58(11) . .
O2 S1 C6 105.69(12) . .
O5 S2 O4 113.99(12) . .
O5 S2 O6 113.33(12) . .
O4 S2 O6 111.25(11) . .
O5 S2 C11 106.29(12) . .
O4 S2 C11 106.02(11) . .
O6 S2 C11 105.15(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.341(4) .
C1 C2 1.365(4) .
C1 H1A 0.9300 .
C2 C3 1.363(4) .
C2 H2A 0.9300 .
C3 C4 1.381(4) .
C3 H3A 0.9300 .
C4 C5 1.363(4) .
C4 H4A 0.9300 .
C5 N1 1.335(4) .
C5 H5A 0.9300 .
C6 C7 1.369(3) .
C6 C10 1.440(3) .
C6 S1 1.785(3) .
C7 C8 1.411(3) .
C7 H7A 0.9300 .
C8 C9 1.372(3) 2_677
C8 H8A 0.9300 .
C9 C8 1.372(3) 2_677
C9 C10 1.420(3) .
C9 H9A 0.9300 .
C10 C10 1.434(5) 2_677
C11 C12 1.375(3) .
C11 C15 1.437(3) .
C11 S2 1.794(3) .
C12 C13 1.414(4) .
C12 H12A 0.9300 .
C13 C14 1.351(4) 2_676
C13 H13A 0.9300 .
C14 C13 1.351(4) 2_676
C14 C15 1.427(3) .
C14 H14A 0.9300 .
C15 C15 1.432(5) 2_676
C16 N3 1.324(3) .
C16 N2 1.331(3) .
C16 N4 1.332(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 1.456(2) .
O2 S1 1.470(2) .
O3 S1 1.456(2) .
O4 S2 1.465(2) .
O5 S2 1.446(2) .
O6 S2 1.4729(19) .
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
N2 H2C O2 0.86 2.12 2.922(3) 155.3 .
N2 H2C S1 0.86 3.01 3.631(3) 130.8 .
N1 H1B O6 0.86 2.02 2.798(3) 149.3 1_545
N2 H2B O4 0.86 2.07 2.817(3) 145.3 2_666
N3 H3B O4 0.86 2.49 3.145(3) 133.1 2_666
N3 H3B O5 0.86 2.51 3.065(3) 122.7 1_455
N3 H3C O1 0.86 2.08 2.916(3) 163.7 1_455
N4 H4B O3 0.86 2.09 2.932(3) 165.8 1_455
N4 H4B S1 0.86 3.02 3.801(4) 152.2 1_455
N4 H4C O2 0.86 2.28 2.976(3) 138.5 2_667
