#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:38:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179670 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/23/4512349.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_4512349
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                92.283(6)
_cell_angle_beta                 101.589(9)
_cell_angle_gamma                90.378(8)
_cell_formula_units_Z            2
_cell_length_a                   8.042(4)
_cell_length_b                   8.179(4)
_cell_length_c                   14.106(8)
_cell_measurement_reflns_used    2365
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.5010
_cell_measurement_theta_min      2.4925
_cell_volume                     908.1(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      223(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  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0695
_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            9929
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 180
_diffrn_standards_interval_time  9
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  0.910
_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    1.560
_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         0.339
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.915
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0548P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1080
_reflns_number_gt                2844
_reflns_number_total             4162
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5014895_si_003.cif
_cod_data_source_block           14-223K
_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_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4512349
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 0.7843(4) 0.3069(3) 0.7384(2) 0.0550(8) Uani 1 1 d .
H1A H 0.7183 0.3999 0.7378 0.066 Uiso 1 1 calc R
C2 C 0.8352(4) 0.2300(4) 0.8204(2) 0.0589(8) Uani 1 1 d .
H2A H 0.8069 0.2704 0.8776 0.071 Uiso 1 1 calc R
C3 C 0.9296(4) 0.0908(4) 0.8201(2) 0.0585(8) Uani 1 1 d .
H3A H 0.9679 0.0367 0.8770 0.070 Uiso 1 1 calc R
C4 C 0.9663(3) 0.0331(3) 0.7340(2) 0.0520(7) Uani 1 1 d .
H4A H 1.0272 -0.0628 0.7318 0.062 Uiso 1 1 calc R
C5 C 0.9153(3) 0.1139(3) 0.65446(17) 0.0361(6) Uani 1 1 d .
H5A H 0.9408 0.0742 0.5964 0.043 Uiso 1 1 calc R
C6 C 0.6120(3) 0.7984(2) 0.51986(14) 0.0246(5) Uani 1 1 d .
C7 C 0.5096(3) 0.7196(3) 0.57068(16) 0.0303(5) Uani 1 1 d .
H7A H 0.5355 0.6142 0.5907 0.036 Uiso 1 1 calc R
C8 C 0.6343(3) 1.2033(3) 0.40712(16) 0.0339(5) Uani 1 1 d .
H8A H 0.7039 1.2592 0.3737 0.041 Uiso 1 1 calc R
C9 C 0.6731(3) 1.0483(3) 0.43386(15) 0.0281(5) Uani 1 1 d .
H9A H 0.7671 0.9985 0.4167 0.034 Uiso 1 1 calc R
C10 C 0.5731(2) 0.9609(2) 0.48743(14) 0.0225(4) Uani 1 1 d .
C11 C 0.5917(3) 0.8735(2) 0.90963(15) 0.0249(5) Uani 1 1 d .
C12 C 0.5259(3) 0.9476(3) 0.82580(16) 0.0307(5) Uani 1 1 d .
H12A H 0.5526 0.9091 0.7679 0.037 Uiso 1 1 calc R
C13 C 0.4173(3) 1.0824(3) 0.82618(16) 0.0325(5) Uani 1 1 d .
H13A H 0.3720 1.1314 0.7685 0.039 Uiso 1 1 calc R
C14 C 0.6212(3) 0.8593(3) 1.08929(16) 0.0292(5) Uani 1 1 d .
H14A H 0.6926 0.7702 1.0900 0.035 Uiso 1 1 calc R
C15 C 0.5549(2) 0.9312(2) 1.00027(15) 0.0238(5) Uani 1 1 d .
C16 C 0.1905(3) 0.5770(2) 0.81036(15) 0.0264(5) Uani 1 1 d .
N1 N 0.8289(3) 0.2494(3) 0.65593(18) 0.0574(6) Uani 1 1 d .
H1B H 0.8004 0.3023 0.6038 0.069 Uiso 1 1 calc R
N2 N 0.1893(2) 0.6243(2) 0.90166(13) 0.0371(5) Uani 1 1 d .
H2B H 0.2768 0.6090 0.9465 0.045 Uiso 1 1 calc R
H2C H 0.1010 0.6702 0.9158 0.045 Uiso 1 1 calc R
N3 N 0.3255(2) 0.5067(2) 0.78836(13) 0.0329(4) Uani 1 1 d .
H3B H 0.3272 0.4791 0.7291 0.039 Uiso 1 1 calc R
H3C H 0.4120 0.4884 0.8333 0.039 Uiso 1 1 calc R
N4 N 0.0571(2) 0.6055(2) 0.74165(13) 0.0374(5) Uani 1 1 d .
H4B H 0.0582 0.5781 0.6823 0.045 Uiso 1 1 calc R
H4C H -0.0308 0.6514 0.7563 0.045 Uiso 1 1 calc R
O1 O 0.7648(2) 0.6659(2) 0.39112(11) 0.0425(4) Uani 1 1 d .
O2 O 0.93890(19) 0.8049(2) 0.53076(12) 0.0430(4) Uani 1 1 d .
O3 O 0.8047(2) 0.54628(19) 0.54877(12) 0.0449(5) Uani 1 1 d .
O4 O 0.88720(18) 0.74121(19) 0.96735(11) 0.0365(4) Uani 1 1 d .
O5 O 0.7408(2) 0.68438(18) 0.80192(11) 0.0348(4) Uani 1 1 d .
O6 O 0.63816(19) 0.56239(17) 0.93348(11) 0.0324(4) Uani 1 1 d .
S1 S 0.79463(7) 0.69451(7) 0.49580(4) 0.02922(16) Uani 1 1 d .
S2 S 0.72586(7) 0.70251(7) 0.90278(4) 0.02760(15) 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 119.9(3) . .
C2 C1 H1A 120.1 . .
N1 C1 H1A 120.1 . .
C1 C2 C3 119.6(3) . .
C1 C2 H2A 120.2 . .
C3 C2 H2A 120.2 . .
C4 C3 C2 118.6(3) . .
C4 C3 H3A 120.7 . .
C2 C3 H3A 120.7 . .
C5 C4 C3 119.9(3) . .
C5 C4 H4A 120.0 . .
C3 C4 H4A 120.0 . .
N1 C5 C4 121.1(2) . .
N1 C5 H5A 119.5 . .
C4 C5 H5A 119.5 . .
C7 C6 C10 120.54(19) . .
C7 C6 S1 118.19(16) . .
C10 C6 S1 121.27(16) . .
C6 C7 C8 120.6(2) . 2_676
C6 C7 H7A 119.7 . .
C8 C7 H7A 119.7 2_676 .
C9 C8 C7 120.9(2) . 2_676
C9 C8 H8A 119.6 . .
C7 C8 H8A 119.6 2_676 .
C8 C9 C10 121.2(2) . .
C8 C9 H9A 119.4 . .
C10 C9 H9A 119.4 . .
C9 C10 C6 123.23(19) . .
C9 C10 C10 118.7(2) . 2_676
C6 C10 C10 118.1(2) . 2_676
C12 C11 C15 121.15(19) . .
C12 C11 S2 117.76(16) . .
C15 C11 S2 121.09(15) . .
C11 C12 C13 120.5(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 121.4(2) 2_677 .
C13 C14 H14A 119.3 2_677 .
C15 C14 H14A 119.3 . .
C14 C15 C11 123.27(19) . .
C14 C15 C15 119.0(2) . 2_677
C11 C15 C15 117.8(2) . 2_677
N3 C16 N4 120.3(2) . .
N3 C16 N2 120.2(2) . .
N4 C16 N2 119.5(2) . .
C5 N1 C1 120.8(2) . .
C5 N1 H1B 119.6 . .
C1 N1 H1B 119.6 . .
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 113.68(10) . .
O3 S1 O2 112.60(11) . .
O1 S1 O2 111.82(11) . .
O3 S1 C6 105.80(10) . .
O1 S1 C6 105.95(10) . .
O2 S1 C6 106.27(10) . .
O4 S2 O5 112.67(10) . .
O4 S2 O6 112.64(10) . .
O5 S2 O6 112.19(9) . .
O4 S2 C11 107.02(10) . .
O5 S2 C11 105.84(9) . .
O6 S2 C11 105.85(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 1.353(3) .
C1 H1A 0.9300 .
C2 C3 1.374(4) .
C2 H2A 0.9300 .
C3 C4 1.372(4) .
C3 H3A 0.9300 .
C4 C5 1.320(3) .
C4 H4A 0.9300 .
C5 N1 1.314(3) .
C5 H5A 0.9300 .
C6 C7 1.369(3) .
C6 C10 1.438(3) .
C6 S1 1.786(2) .
C7 C8 1.405(3) 2_676
C7 H7A 0.9300 .
C8 C9 1.358(3) .
C8 C7 1.405(3) 2_676
C8 H8A 0.9300 .
C9 C10 1.418(3) .
C9 H9A 0.9300 .
C10 C10 1.441(4) 2_676
C11 C12 1.362(3) .
C11 C15 1.432(3) .
C11 S2 1.783(2) .
C12 C13 1.411(3) .
C12 H12A 0.9300 .
C13 C14 1.360(3) 2_677
C13 H13A 0.9300 .
C14 C13 1.360(3) 2_677
C14 C15 1.415(3) .
C14 H14A 0.9300 .
C15 C15 1.434(4) 2_677
C16 N3 1.318(3) .
C16 N4 1.322(3) .
C16 N2 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 1.4568(17) .
O2 S1 1.4578(17) .
O3 S1 1.4435(17) .
O4 S2 1.4527(16) .
O5 S2 1.4535(17) .
O6 S2 1.4663(16) .
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 2.17 2.898(3) 141.9 .
N3 H3C O6 0.86 2.13 2.926(3) 152.8 .
N2 H2B O6 0.86 2.24 2.946(3) 138.8 2_667
N2 H2C O4 0.86 2.07 2.922(3) 168.5 1_455
N2 H2C S2 0.86 3.00 3.789(3) 153.5 1_455
N3 H3B O1 0.86 2.04 2.809(3) 148.9 2_666
N4 H4B O3 0.86 2.49 3.069(3) 125.7 1_455
N4 H4C O5 0.86 2.08 2.908(3) 161.3 1_455
