#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:38:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179670 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/23/4512354.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_4512354
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         426.48
_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                92.269(5)
_cell_angle_beta                 101.891(8)
_cell_angle_gamma                90.195(7)
_cell_formula_units_Z            2
_cell_length_a                   8.057(4)
_cell_length_b                   8.203(4)
_cell_length_c                   14.119(7)
_cell_measurement_reflns_used    2327
_cell_measurement_temperature    248(2)
_cell_measurement_theta_max      27.4971
_cell_measurement_theta_min      2.4852
_cell_volume                     912.3(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      248(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0413
_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            9954
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_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    1.553
_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         0.393
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0419
_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)+(0.0806P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1358
_reflns_number_gt                3144
_reflns_number_total             4162
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5014895_si_003.cif
_cod_data_source_block           19-248K
_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               4512354
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 0.7839(4) 0.3094(4) 0.7375(2) 0.0623(9) Uani 1 1 d .
H1A H 0.7183 0.4027 0.7367 0.075 Uiso 1 1 calc R
C2 C 0.8321(4) 0.2314(4) 0.8194(2) 0.0662(9) Uani 1 1 d .
H2A H 0.8021 0.2708 0.8762 0.079 Uiso 1 1 calc R
C3 C 0.9266(4) 0.0920(4) 0.8193(2) 0.0659(9) Uani 1 1 d .
H3A H 0.9630 0.0372 0.8762 0.079 Uiso 1 1 calc R
C4 C 0.9664(4) 0.0351(3) 0.7341(2) 0.0563(8) Uani 1 1 d .
H4A H 1.0271 -0.0607 0.7319 0.068 Uiso 1 1 calc R
C5 C 0.9168(3) 0.1192(3) 0.65447(17) 0.0420(6) Uani 1 1 d .
H5A H 0.9444 0.0818 0.5967 0.050 Uiso 1 1 calc R
C6 C 0.6108(3) 0.7982(3) 0.51987(14) 0.0260(4) Uani 1 1 d .
C7 C 0.5084(3) 0.7196(3) 0.57033(16) 0.0337(5) Uani 1 1 d .
H7A H 0.5339 0.6143 0.5904 0.040 Uiso 1 1 calc R
C8 C 0.6353(3) 1.2018(3) 0.40818(17) 0.0366(5) Uani 1 1 d .
H8A H 0.7053 1.2570 0.3751 0.044 Uiso 1 1 calc R
C9 C 0.6736(3) 1.0470(3) 0.43486(15) 0.0301(5) Uani 1 1 d .
H9A H 0.7675 0.9967 0.4182 0.036 Uiso 1 1 calc R
C10 C 0.5721(2) 0.9604(2) 0.48795(14) 0.0241(4) Uani 1 1 d .
C11 C 0.5907(3) 0.8733(2) 0.90974(15) 0.0272(4) Uani 1 1 d .
C12 C 0.5237(3) 0.9476(3) 0.82563(16) 0.0336(5) Uani 1 1 d .
H12A H 0.5496 0.9089 0.7676 0.040 Uiso 1 1 calc R
C13 C 0.4158(3) 1.0825(3) 0.82600(16) 0.0357(5) Uani 1 1 d .
H13A H 0.3700 1.1314 0.7683 0.043 Uiso 1 1 calc R
C14 C 0.6217(3) 0.8586(3) 1.08934(16) 0.0325(5) Uani 1 1 d .
H14A H 0.6924 0.7691 1.0900 0.039 Uiso 1 1 calc R
C15 C 0.5549(3) 0.9315(2) 1.00044(15) 0.0260(4) Uani 1 1 d .
C16 C 0.8110(3) 0.4219(3) 0.18932(15) 0.0290(5) Uani 1 1 d .
N1 N 0.8298(3) 0.2535(3) 0.65621(18) 0.0559(6) Uani 1 1 d .
H1B H 0.8017 0.3070 0.6042 0.067 Uiso 1 1 calc R
N2 N 0.6768(2) 0.4919(2) 0.21154(14) 0.0364(5) Uani 1 1 d .
H2B H 0.6757 0.5189 0.2709 0.044 Uiso 1 1 calc R
H2C H 0.5899 0.5107 0.1667 0.044 Uiso 1 1 calc R
N3 N 0.8113(3) 0.3755(3) 0.09803(13) 0.0401(5) Uani 1 1 d .
H3B H 0.7235 0.3913 0.0533 0.048 Uiso 1 1 calc R
H3C H 0.8993 0.3298 0.0837 0.048 Uiso 1 1 calc R
N4 N 0.9448(3) 0.3928(3) 0.25820(14) 0.0407(5) Uani 1 1 d .
H4B H 0.9439 0.4198 0.3176 0.049 Uiso 1 1 calc R
H4C H 1.0325 0.3470 0.2436 0.049 Uiso 1 1 calc R
O1 O 0.7622(2) 0.6650(2) 0.39132(12) 0.0474(5) Uani 1 1 d .
O2 O 0.9371(2) 0.8008(2) 0.53160(13) 0.0473(5) Uani 1 1 d .
O3 O 0.8012(2) 0.5445(2) 0.54853(14) 0.0501(5) Uani 1 1 d .
O4 O 0.7389(2) 0.68478(19) 0.80181(11) 0.0389(4) Uani 1 1 d .
O5 O 0.6378(2) 0.56324(19) 0.93342(11) 0.0366(4) Uani 1 1 d .
O6 O 0.8861(2) 0.7410(2) 0.96729(12) 0.0403(4) Uani 1 1 d .
S1 S 0.79257(7) 0.69262(7) 0.49592(4) 0.03158(17) Uani 1 1 d .
S2 S 0.72469(7) 0.70275(7) 0.90277(4) 0.02998(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 120.0(3) . .
C2 C1 H1A 120.0 . .
N1 C1 H1A 120.0 . .
C1 C2 C3 119.4(3) . .
C1 C2 H2A 120.3 . .
C3 C2 H2A 120.3 . .
C4 C3 C2 119.0(3) . .
C4 C3 H3A 120.5 . .
C2 C3 H3A 120.5 . .
C5 C4 C3 119.1(3) . .
C5 C4 H4A 120.5 . .
C3 C4 H4A 120.5 . .
N1 C5 C4 121.2(2) . .
N1 C5 H5A 119.4 . .
C4 C5 H5A 119.4 . .
C7 C6 C10 120.51(19) . .
C7 C6 S1 117.89(17) . .
C10 C6 S1 121.60(16) . .
C6 C7 C8 120.0(2) . 2_676
C6 C7 H7A 120.0 . .
C8 C7 H7A 120.0 2_676 .
C9 C8 C7 121.2(2) . 2_676
C9 C8 H8A 119.4 . .
C7 C8 H8A 119.4 2_676 .
C8 C9 C10 121.0(2) . .
C8 C9 H9A 119.5 . .
C10 C9 H9A 119.5 . .
C9 C10 C10 118.5(2) . 2_676
C9 C10 C6 122.75(19) . .
C10 C10 C6 118.7(2) 2_676 .
C12 C11 C15 121.00(19) . .
C12 C11 S2 117.73(16) . .
C15 C11 S2 121.27(16) . .
C11 C12 C13 120.6(2) . .
C11 C12 H12A 119.7 . .
C13 C12 H12A 119.7 . .
C14 C13 C12 120.2(2) 2_677 .
C14 C13 H13A 119.9 2_677 .
C12 C13 H13A 119.9 . .
C13 C14 C15 121.1(2) 2_677 .
C13 C14 H14A 119.4 2_677 .
C15 C14 H14A 119.4 . .
C14 C15 C15 119.3(2) . 2_677
C14 C15 C11 122.96(19) . .
C15 C15 C11 117.7(2) 2_677 .
N2 C16 N4 120.1(2) . .
N2 C16 N3 120.2(2) . .
N4 C16 N3 119.6(2) . .
C5 N1 C1 121.3(3) . .
C5 N1 H1B 119.4 . .
C1 N1 H1B 119.4 . .
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 O2 112.58(12) . .
O3 S1 O1 113.74(11) . .
O2 S1 O1 111.99(11) . .
O3 S1 C6 105.70(11) . .
O2 S1 C6 106.17(10) . .
O1 S1 C6 105.91(10) . .
O6 S2 O4 112.61(11) . .
O6 S2 O5 112.63(10) . .
O4 S2 O5 112.23(10) . .
O6 S2 C11 107.01(10) . .
O4 S2 C11 105.92(10) . .
O5 S2 C11 105.83(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.331(4) .
C1 N1 1.342(4) .
C1 H1A 0.9300 .
C2 C3 1.376(5) .
C2 H2A 0.9300 .
C3 C4 1.372(4) .
C3 H3A 0.9300 .
C4 C5 1.333(4) .
C4 H4A 0.9300 .
C5 N1 1.310(3) .
C5 H5A 0.9300 .
C6 C7 1.370(3) .
C6 C10 1.436(3) .
C6 S1 1.789(2) .
C7 C8 1.408(3) 2_676
C7 H7A 0.9300 .
C8 C9 1.357(3) .
C8 C7 1.408(3) 2_676
C8 H8A 0.9300 .
C9 C10 1.423(3) .
C9 H9A 0.9300 .
C10 C10 1.428(4) 2_676
C11 C12 1.367(3) .
C11 C15 1.434(3) .
C11 S2 1.782(2) .
C12 C13 1.410(3) .
C12 H12A 0.9300 .
C13 C14 1.363(3) 2_677
C13 H13A 0.9300 .
C14 C13 1.363(3) 2_677
C14 C15 1.416(3) .
C14 H14A 0.9300 .
C15 C15 1.431(4) 2_677
C16 N2 1.314(3) .
C16 N4 1.324(3) .
C16 N3 1.330(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 1.4548(18) .
O2 S1 1.4534(18) .
O3 S1 1.4437(19) .
O4 S2 1.4552(17) .
O5 S2 1.4648(17) .
O6 S2 1.4511(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 H1B O3 0.86 2.13 2.864(3) 143.2 .
N2 H2B O1 0.86 2.04 2.814(3) 149.6 .
N2 H2C O5 0.86 2.14 2.932(3) 152.5 2_666
N3 H3B O5 0.86 2.25 2.947(3) 138.7 1_554
N3 H3C O6 0.86 2.08 2.929(3) 168.7 2_766
N3 H3C S2 0.86 3.01 3.797(3) 153.4 2_766
N4 H4B O3 0.86 2.50 3.079(3) 125.8 2_766
N4 H4C O4 0.86 2.08 2.911(3) 161.0 2_766
