# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c:\frames\643\work\643s
_database_code_depnum_ccdc_archive 'CCDC 1404793'
_audit_update_record             
;
2015-06-03 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        "N,N'-bis(2-pyridyl)guanidinium chloride"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 Cl N5'
_chemical_formula_weight         249.71

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.0796(13)
_cell_length_b                   10.6907(10)
_cell_length_c                   16.9593(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.751(2)
_cell_angle_gamma                90.00
_cell_volume                     2402.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8884
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14374
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         28.33
_reflns_number_total             5925
_reflns_number_gt                3506
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0641P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5925
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1315
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.13238(4) 0.42127(5) 0.06391(4) 0.03988(16) Uani 1 1 d . . .
N1 N -0.36832(14) 0.0411(2) -0.10268(13) 0.0492(5) Uani 1 1 d . . .
C1 C -0.34454(16) 0.1496(2) -0.06258(13) 0.0362(5) Uani 1 1 d . . .
Cl2 Cl 1.07047(5) -0.12134(6) 0.41207(4) 0.05115(19) Uani 1 1 d . . .
N2 N -0.24477(13) 0.19183(17) -0.04199(12) 0.0371(4) Uani 1 1 d . . .
H2 H -0.2298 0.2606 -0.0118 0.044 Uiso 1 1 calc R . .
C2 C -0.41310(17) 0.2218(2) -0.03907(14) 0.0400(5) Uani 1 1 d . . .
H2A H -0.3931 0.2989 -0.0104 0.048 Uiso 1 1 calc R . .
N3 N -0.18099(14) 0.04060(17) -0.10928(11) 0.0385(4) Uani 1 1 d . . .
H3A H -0.1299 0.0101 -0.1219 0.046 Uiso 1 1 calc R . .
H3B H -0.2403 0.0038 -0.1281 0.046 Uiso 1 1 calc R . .
C3 C -0.50982(18) 0.1789(2) -0.05838(15) 0.0475(6) Uani 1 1 d . . .
H3 H -0.5579 0.2250 -0.0423 0.057 Uiso 1 1 calc R . .
N4 N -0.08024(13) 0.20048(16) -0.03224(12) 0.0362(4) Uani 1 1 d . . .
H4 H -0.0797 0.2665 -0.0011 0.043 Uiso 1 1 calc R . .
C4 C -0.5365(2) 0.0684(3) -0.10123(18) 0.0603(8) Uani 1 1 d . . .
H4A H -0.6038 0.0384 -0.1171 0.072 Uiso 1 1 calc R . .
N5 N 0.01806(14) 0.06943(17) -0.08551(11) 0.0369(4) Uani 1 1 d . . .
C5 C -0.4636(2) 0.0016(3) -0.12085(19) 0.0636(8) Uani 1 1 d . . .
H5 H -0.4819 -0.0764 -0.1487 0.076 Uiso 1 1 calc R . .
N6 N 0.82449(13) 0.21401(18) 0.21000(12) 0.0393(5) Uani 1 1 d . . .
C6 C -0.16880(16) 0.14048(19) -0.06262(13) 0.0331(5) Uani 1 1 d . . .
N7 N 0.95742(13) 0.09366(17) 0.29565(11) 0.0373(4) Uani 1 1 d . . .
H7 H 0.9737 0.0285 0.3293 0.045 Uiso 1 1 calc R . .
C7 C 0.01157(16) 0.1722(2) -0.04341(14) 0.0347(5) Uani 1 1 d . . .
N8 N 1.01689(14) 0.23174(18) 0.21654(12) 0.0425(5) Uani 1 1 d . . .
H8A H 1.0672 0.2587 0.2013 0.051 Uiso 1 1 calc R . .
H8B H 0.9568 0.2662 0.1953 0.051 Uiso 1 1 calc R . .
C8 C 0.09107(18) 0.2556(2) -0.01034(15) 0.0434(6) Uani 1 1 d . . .
H8 H 0.0827 0.3287 0.0184 0.052 Uiso 1 1 calc R . .
N9 N 1.12159(13) 0.08485(17) 0.30496(12) 0.0383(4) Uani 1 1 d . . .
H9 H 1.1235 0.0229 0.3397 0.046 Uiso 1 1 calc R . .
C9 C 0.18165(19) 0.2297(2) -0.02024(16) 0.0488(6) Uani 1 1 d . . .
H9A H 0.2376 0.2844 0.0019 0.059 Uiso 1 1 calc R . .
N10 N 1.21364(14) 0.19946(18) 0.23671(12) 0.0408(5) Uani 1 1 d . . .
C10 C 0.19009(19) 0.1228(2) -0.06295(16) 0.0476(6) Uani 1 1 d . . .
H10 H 0.2521 0.1025 -0.0705 0.057 Uiso 1 1 calc R . .
C11 C 0.10753(18) 0.0462(2) -0.09435(14) 0.0419(6) Uani 1 1 d . . .
H11 H 0.1142 -0.0270 -0.1238 0.050 Uiso 1 1 calc R . .
C12 C 0.85749(16) 0.1363(2) 0.27437(14) 0.0341(5) Uani 1 1 d . . .
C13 C 0.79911(18) 0.0949(2) 0.32074(15) 0.0409(6) Uani 1 1 d . . .
H13 H 0.8260 0.0395 0.3667 0.049 Uiso 1 1 calc R . .
C14 C 0.70120(18) 0.1365(2) 0.29803(16) 0.0459(6) Uani 1 1 d . . .
H14 H 0.6587 0.1090 0.3277 0.055 Uiso 1 1 calc R . .
C15 C 0.66496(17) 0.2188(2) 0.23144(15) 0.0434(6) Uani 1 1 d . . .
H15 H 0.5978 0.2496 0.2150 0.052 Uiso 1 1 calc R . .
C16 C 0.72929(17) 0.2547(2) 0.18990(15) 0.0415(5) Uani 1 1 d . . .
H16 H 0.7048 0.3115 0.1444 0.050 Uiso 1 1 calc R . .
C17 C 1.03137(16) 0.1408(2) 0.27053(14) 0.0351(5) Uani 1 1 d . . .
C18 C 1.21310(16) 0.1125(2) 0.29269(14) 0.0341(5) Uani 1 1 d . . .
C19 C 1.29890(17) 0.0466(2) 0.34031(14) 0.0409(5) Uani 1 1 d . . .
H19 H 1.2953 -0.0153 0.3794 0.049 Uiso 1 1 calc R . .
C20 C 1.38858(18) 0.0739(2) 0.32895(16) 0.0472(6) Uani 1 1 d . . .
H20 H 1.4485 0.0309 0.3603 0.057 Uiso 1 1 calc R . .
C21 C 1.39105(18) 0.1643(2) 0.27169(16) 0.0473(6) Uani 1 1 d . . .
H21 H 1.4526 0.1851 0.2633 0.057 Uiso 1 1 calc R . .
C22 C 1.30308(18) 0.2233(2) 0.22716(16) 0.0461(6) Uani 1 1 d . . .
H22 H 1.3052 0.2847 0.1872 0.055 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.329(3) . ?
N1 C5 1.339(3) . ?
C1 C2 1.395(3) . ?
C1 N2 1.403(3) . ?
N2 C6 1.349(3) . ?
C2 C3 1.368(3) . ?
N3 C6 1.305(3) . ?
C3 C4 1.371(3) . ?
N4 C6 1.341(3) . ?
N4 C7 1.401(3) . ?
C4 C5 1.380(4) . ?
N5 C7 1.330(3) . ?
N5 C11 1.341(3) . ?
N6 C12 1.325(3) . ?
N6 C16 1.339(3) . ?
N7 C17 1.349(3) . ?
N7 C12 1.405(3) . ?
C7 C8 1.392(3) . ?
N8 C17 1.303(3) . ?
C8 C9 1.370(3) . ?
N9 C17 1.346(3) . ?
N9 C18 1.404(3) . ?
C9 C10 1.380(4) . ?
N10 C18 1.331(3) . ?
N10 C22 1.347(3) . ?
C10 C11 1.374(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.374(3) . ?
C14 C15 1.386(3) . ?
C15 C16 1.377(3) . ?
C18 C19 1.396(3) . ?
C19 C20 1.372(3) . ?
C20 C21 1.378(4) . ?
C21 C22 1.368(3) . ?

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
_geom_angle_publ_flag
C1 N1 C5 116.9(2) . . ?
N1 C1 C2 123.4(2) . . ?
N1 C1 N2 117.77(19) . . ?
C2 C1 N2 118.9(2) . . ?
C6 N2 C1 128.28(19) . . ?
C3 C2 C1 118.4(2) . . ?
C2 C3 C4 119.2(2) . . ?
C6 N4 C7 128.72(18) . . ?
C3 C4 C5 118.7(2) . . ?
C7 N5 C11 116.8(2) . . ?
N1 C5 C4 123.4(3) . . ?
C12 N6 C16 117.10(19) . . ?
N3 C6 N4 122.6(2) . . ?
N3 C6 N2 122.5(2) . . ?
N4 C6 N2 114.92(18) . . ?
C17 N7 C12 127.60(18) . . ?
N5 C7 C8 123.6(2) . . ?
N5 C7 N4 118.98(19) . . ?
C8 C7 N4 117.4(2) . . ?
C9 C8 C7 118.5(2) . . ?
C17 N9 C18 128.39(19) . . ?
C8 C9 C10 118.7(2) . . ?
C18 N10 C22 116.7(2) . . ?
C11 C10 C9 119.1(2) . . ?
N5 C11 C10 123.4(2) . . ?
N6 C12 C13 123.8(2) . . ?
N6 C12 N7 117.20(18) . . ?
C13 C12 N7 119.0(2) . . ?
C14 C13 C12 117.9(2) . . ?
C13 C14 C15 119.5(2) . . ?
C16 C15 C14 118.0(2) . . ?
N6 C16 C15 123.7(2) . . ?
N8 C17 N9 122.5(2) . . ?
N8 C17 N7 123.1(2) . . ?
N9 C17 N7 114.37(19) . . ?
N10 C18 C19 123.6(2) . . ?
N10 C18 N9 118.6(2) . . ?
C19 C18 N9 117.8(2) . . ?
C20 C19 C18 118.0(2) . . ?
C19 C20 C21 119.5(2) . . ?
C22 C21 C20 118.6(2) . . ?
N10 C22 C21 123.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.061


_exptl_crystal_recrystallization_method 
'Slow diffusion of diethyl ether into methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c:\frames\644\work\cc
_database_code_depnum_ccdc_archive 'CCDC 1404794'
_audit_update_record             
;
2015-06-03 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        "N,N'-bis(2-pyridyl)guanidinium nitrate"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 N6 O3'
_chemical_formula_weight         276.27

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Cc

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   11.5823(17)
_cell_length_b                   13.2072(17)
_cell_length_c                   8.6438(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.838(4)
_cell_angle_gamma                90.00
_cell_volume                     1235.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9562
_exptl_absorpt_correction_T_max  0.9745
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7687
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         28.31
_reflns_number_total             3053
_reflns_number_gt                2908
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0574P)²+0.2195P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(8)
_refine_ls_number_reflns         3053
_refine_ls_number_parameters     182
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0954
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.11709(12) 0.21467(9) 0.16195(17) 0.0497(3) Uani 1 1 d . . .
N1 N 0.20959(13) -0.14351(10) 0.25119(17) 0.0365(3) Uani 1 1 d . . .
C1 C 0.21309(14) -0.04253(11) 0.24441(19) 0.0302(3) Uani 1 1 d . . .
O2 O -0.03200(14) 0.23739(9) -0.07467(17) 0.0505(3) Uani 1 1 d . . .
N2 N 0.12547(12) 0.00716(9) 0.11031(16) 0.0304(2) Uani 1 1 d . . .
H2 H 0.1245 0.0737 0.1152 0.036 Uiso 1 1 calc R . .
C2 C 0.29826(14) 0.01683(12) 0.36668(18) 0.0345(3) Uani 1 1 d . . .
H2A H 0.2993 0.0884 0.3570 0.041 Uiso 1 1 calc R . .
O3 O -0.03480(13) 0.31403(10) 0.14514(19) 0.0546(4) Uani 1 1 d . . .
N3 N 0.03573(13) -0.13470(10) -0.04635(17) 0.0374(3) Uani 1 1 d . . .
H3A H -0.0192 -0.1613 -0.1356 0.045 Uiso 1 1 calc R . .
H3B H 0.0866 -0.1742 0.0295 0.045 Uiso 1 1 calc R . .
C3 C 0.38027(15) -0.03233(13) 0.5012(2) 0.0386(3) Uani 1 1 d . . .
H3 H 0.4393 0.0053 0.5868 0.046 Uiso 1 1 calc R . .
N4 N -0.03352(11) 0.02819(10) -0.13819(14) 0.0319(3) Uani 1 1 d . . .
H4 H -0.0182 0.0932 -0.1193 0.038 Uiso 1 1 calc R . .
C4 C 0.37674(17) -0.13710(14) 0.5118(2) 0.0415(4) Uani 1 1 d . . .
H4A H 0.4319 -0.1720 0.6049 0.050 Uiso 1 1 calc R . .
N5 N -0.14794(12) -0.09358(10) -0.32907(16) 0.0360(3) Uani 1 1 d . . .
C5 C 0.29164(16) -0.18874(13) 0.3846(2) 0.0411(4) Uani 1 1 d . . .
H5A H 0.2905 -0.2605 0.3908 0.049 Uiso 1 1 calc R . .
N6 N 0.01768(11) 0.25672(8) 0.07450(15) 0.0294(2) Uani 1 1 d . . .
C6 C 0.04179(14) -0.03627(11) -0.02649(18) 0.0301(3) Uani 1 1 d . . .
C7 C -0.13394(14) 0.00264(11) -0.28180(18) 0.0316(3) Uani 1 1 d . . .
C8 C -0.21340(15) 0.08045(12) -0.36652(19) 0.0371(3) Uani 1 1 d . . .
H8 H -0.1990 0.1488 -0.3303 0.044 Uiso 1 1 calc R . .
C9 C -0.31339(17) 0.05416(14) -0.5045(2) 0.0422(4) Uani 1 1 d . . .
H9 H -0.3701 0.1046 -0.5647 0.051 Uiso 1 1 calc R . .
C10 C -0.33097(16) -0.04650(14) -0.5552(2) 0.0412(4) Uani 1 1 d . . .
H10 H -0.3995 -0.0659 -0.6498 0.049 Uiso 1 1 calc R . .
C11 C -0.24648(15) -0.11713(14) -0.4648(2) 0.0398(4) Uani 1 1 d . . .
H11 H -0.2581 -0.1858 -0.4996 0.048 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N6 1.2595(17) . ?
N1 C1 1.3362(19) . ?
N1 C5 1.345(2) . ?
C1 C2 1.401(2) . ?
C1 N2 1.403(2) . ?
O2 N6 1.2374(18) . ?
N2 C6 1.361(2) . ?
C2 C3 1.375(2) . ?
O3 N6 1.2567(18) . ?
N3 C6 1.3099(19) . ?
C3 C4 1.388(2) . ?
N4 C6 1.3485(19) . ?
N4 C7 1.4072(19) . ?
C4 C5 1.369(3) . ?
N5 C7 1.3270(19) . ?
N5 C11 1.350(2) . ?
C7 C8 1.400(2) . ?
C8 C9 1.379(2) . ?
C9 C10 1.392(3) . ?
C10 C11 1.376(3) . ?

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
_geom_angle_publ_flag
C1 N1 C5 117.23(14) . . ?
N1 C1 C2 123.34(14) . . ?
N1 C1 N2 118.62(13) . . ?
C2 C1 N2 118.02(13) . . ?
C6 N2 C1 127.11(12) . . ?
C3 C2 C1 117.58(15) . . ?
C2 C3 C4 119.92(15) . . ?
C6 N4 C7 126.97(13) . . ?
C5 C4 C3 118.23(16) . . ?
C7 N5 C11 117.46(14) . . ?
N1 C5 C4 123.67(16) . . ?
O2 N6 O3 120.30(14) . . ?
O2 N6 O1 121.43(14) . . ?
O3 N6 O1 118.10(14) . . ?
N3 C6 N4 122.81(14) . . ?
N3 C6 N2 121.37(14) . . ?
N4 C6 N2 115.82(13) . . ?
N5 C7 C8 123.80(14) . . ?
N5 C7 N4 118.25(13) . . ?
C8 C7 N4 117.95(13) . . ?
C9 C8 C7 117.47(15) . . ?
C8 C9 C10 119.78(16) . . ?
C11 C10 C9 118.27(16) . . ?
N5 C11 C10 123.20(16) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.049



_exptl_crystal_recrystallization_method 
'Slow diffusion of diethyl ether into methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c:\frames\636\work\636s
_database_code_depnum_ccdc_archive 'CCDC 1404795'
_audit_update_record             
;
2015-06-03 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        "N,N'-bis(2-pyridyl)guanidinium hemisulfate"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 N10 O10 S'
_chemical_formula_weight         644.60

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.585(4)
_cell_length_b                   16.445(4)
_cell_length_c                   11.369(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.610(5)
_cell_angle_gamma                90.00
_cell_volume                     3115.9(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9517
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7960
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2747
_reflns_number_gt                2110
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.

Slight disorder observed for the water and methanol molecules included in
the crystal. Hydrogen atoms for these solvent molecules were not included
in the model. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1914P)²+7.2401P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2747
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0959
_refine_ls_wR_factor_ref         0.3015
_refine_ls_wR_factor_gt          0.2831
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.0000 0.24565(9) 0.7500 0.0417(5) Uani 1 2 d S . .
O1 O -0.0477(3) 0.2977(2) 0.8030(5) 0.0798(14) Uani 1 1 d . . .
N1 N 0.0000 -0.0962(3) 0.7500 0.0436(13) Uani 1 2 d S . .
H1A H 0.0266 -0.1230 0.8177 0.052 Uiso 0.50 1 calc PR . .
H1B H -0.0266 -0.1230 0.6823 0.052 Uiso 0.50 1 calc PR . .
C1 C 0.0000 -0.0168(3) 0.7500 0.0317(12) Uani 1 2 d S . .
O2 O -0.0526(3) 0.1935(2) 0.6556(4) 0.0784(14) Uani 1 1 d . . .
N2 N -0.03987(18) 0.0264(2) 0.6485(3) 0.0329(8) Uani 1 1 d . . .
H2 H -0.0368 0.0796 0.6564 0.039 Uiso 1 1 calc R . .
C2 C -0.0858(2) -0.0031(3) 0.5316(3) 0.0348(10) Uani 1 1 d . . .
O3 O 0.2204(3) 0.2563(4) 0.8722(7) 0.130(3) Uani 1 1 d . . .
N3 N -0.0902(2) -0.0830(2) 0.5134(3) 0.0422(9) Uani 1 1 d . . .
C3 C -0.1236(2) 0.0536(3) 0.4407(4) 0.0421(11) Uani 1 1 d . . .
H3 H -0.1187 0.1103 0.4574 0.051 Uiso 1 1 calc R . .
O4 O 0.0054(3) 0.2522(3) 1.0841(5) 0.0919(16) Uani 1 1 d . . .
N4 N 0.0000 0.5881(3) 0.7500 0.0426(13) Uani 1 2 d S . .
H4A H -0.0269 0.6148 0.7910 0.051 Uiso 0.50 1 calc PR . .
H4B H 0.0269 0.6148 0.7090 0.051 Uiso 0.50 1 calc PR . .
C4 C -0.1688(3) 0.0244(4) 0.3245(4) 0.0496(13) Uani 1 1 d . . .
H4 H -0.1960 0.0610 0.2602 0.060 Uiso 1 1 calc R . .
C13 C 0.1767(7) 0.2545(5) 0.3395(8) 0.127(4) Uani 1 1 d . . .
N5 N 0.04009(18) 0.4645(2) 0.6888(3) 0.0338(8) Uani 1 1 d . . .
H5 H 0.0363 0.4113 0.6929 0.041 Uiso 1 1 calc R . .
C5 C -0.1737(3) -0.0582(4) 0.3040(4) 0.0516(13) Uani 1 1 d . . .
H5A H -0.2041 -0.0795 0.2254 0.062 Uiso 1 1 calc R . .
N6 N 0.0886(2) 0.5746(2) 0.5996(3) 0.0428(10) Uani 1 1 d . . .
C6 C -0.1337(3) -0.1093(3) 0.3991(4) 0.0501(12) Uani 1 1 d . . .
H6 H -0.1368 -0.1661 0.3837 0.060 Uiso 1 1 calc R . .
C7 C 0.0000 0.5090(4) 0.7500 0.0328(13) Uani 1 2 d S . .
C8 C 0.0876(2) 0.4951(3) 0.6188(3) 0.0362(10) Uani 1 1 d . . .
C9 C 0.1304(2) 0.4384(3) 0.5725(4) 0.0442(11) Uani 1 1 d . . .
H9 H 0.1286 0.3818 0.5888 0.053 Uiso 1 1 calc R . .
C10 C 0.1754(3) 0.4687(4) 0.5017(4) 0.0532(13) Uani 1 1 d . . .
H10 H 0.2056 0.4327 0.4685 0.064 Uiso 1 1 calc R . .
C11 C 0.1761(3) 0.5517(4) 0.4796(4) 0.0513(13) Uani 1 1 d . . .
H11 H 0.2065 0.5733 0.4312 0.062 Uiso 1 1 calc R . .
C12 C 0.1319(3) 0.6016(3) 0.5294(4) 0.0488(12) Uani 1 1 d . . .
H12 H 0.1319 0.6583 0.5133 0.059 Uiso 1 1 calc R . .
O5 O 0.1624(5) 0.2231(6) 0.2276(9) 0.171(3) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.452(4) . ?
S1 O2 1.452(4) 2_556 ?
S1 O1 1.457(4) 2_556 ?
S1 O1 1.457(4) . ?
N1 C1 1.307(8) . ?
C1 N2 1.345(4) 2_556 ?
C1 N2 1.345(4) . ?
N2 C2 1.403(5) . ?
C2 N3 1.329(6) . ?
C2 C3 1.394(6) . ?
N3 C6 1.351(6) . ?
C3 C4 1.392(6) . ?
N4 C7 1.301(8) . ?
C4 C5 1.375(8) . ?
C13 O5 1.320(12) . ?
N5 C7 1.352(5) . ?
N5 C8 1.417(5) . ?
C5 C6 1.372(7) . ?
N6 C8 1.327(6) . ?
N6 C12 1.342(6) . ?
C7 N5 1.352(5) 2_556 ?
C8 C9 1.402(6) . ?
C9 C10 1.389(6) . ?
C10 C11 1.389(8) . ?
C11 C12 1.371(7) . ?

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
_geom_angle_publ_flag
O2 S1 O2 107.7(3) . 2_556 ?
O2 S1 O1 110.9(3) . 2_556 ?
O2 S1 O1 109.7(3) 2_556 2_556 ?
O2 S1 O1 109.7(3) . . ?
O2 S1 O1 110.9(3) 2_556 . ?
O1 S1 O1 108.0(3) 2_556 . ?
N1 C1 N2 121.8(2) . 2_556 ?
N1 C1 N2 121.8(2) . . ?
N2 C1 N2 116.3(5) 2_556 . ?
C1 N2 C2 127.9(4) . . ?
N3 C2 C3 123.8(4) . . ?
N3 C2 N2 118.5(4) . . ?
C3 C2 N2 117.7(4) . . ?
C2 N3 C6 116.9(4) . . ?
C4 C3 C2 117.7(5) . . ?
C5 C4 C3 119.2(5) . . ?
C7 N5 C8 126.5(4) . . ?
C6 C5 C4 118.8(4) . . ?
C8 N6 C12 117.7(4) . . ?
N3 C6 C5 123.6(5) . . ?
N4 C7 N5 122.7(3) . 2_556 ?
N4 C7 N5 122.7(3) . . ?
N5 C7 N5 114.5(5) 2_556 . ?
N6 C8 C9 123.8(4) . . ?
N6 C8 N5 119.0(4) . . ?
C9 C8 N5 117.2(4) . . ?
C10 C9 C8 116.8(5) . . ?
C11 C10 C9 119.9(5) . . ?
C12 C11 C10 118.4(4) . . ?
N6 C12 C11 123.4(5) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.312
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.117



_exptl_crystal_recrystallization_method 
'Slow diffusion of diethyl ether into methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c:\frames\684\work\pbcn
_database_code_depnum_ccdc_archive 'CCDC 1404796'
_audit_update_record             
;
2015-06-03 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        "N,N'-bis(2-pyridyl)guanidinium hemisulfate"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H19 N5 O5.50 S0.50'
_chemical_formula_weight         325.34

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbcn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   16.941(4)
_cell_length_b                   8.827(2)
_cell_length_c                   20.578(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3077.2(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9167
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17227
_diffrn_reflns_av_R_equivalents  0.1532
_diffrn_reflns_av_sigmaI/netI    0.1005
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2719
_reflns_number_gt                1471
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.

Some disorder was observed in the water solvent molecules included in the
crystal 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0875P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2719
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.1840
_refine_ls_wR_factor_gt          0.1558
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.0000 0.93413(16) 0.2500 0.0456(4) Uani 1 2 d S . .
O5 O -0.0092(3) 1.2890(6) 0.3491(2) 0.0734(11) Uani 1 1 d . . .
O2 O 0.05446(18) 1.0255(4) 0.2864(2) 0.1047(15) Uani 1 1 d . . .
O1 O 0.04586(19) 0.8415(6) 0.2079(3) 0.150(2) Uani 1 1 d . . .
N1 N 0.20438(17) 0.8015(3) 0.20416(14) 0.0405(8) Uani 1 1 d . . .
H1 H 0.1536 0.8151 0.2108 0.049 Uiso 1 1 calc R . .
N3 N 0.32890(17) 0.8668(4) 0.24114(15) 0.0466(8) Uani 1 1 d . . .
H3A H 0.3509 0.8046 0.2130 0.056 Uiso 1 1 calc R . .
H3B H 0.3586 0.9201 0.2677 0.056 Uiso 1 1 calc R . .
N2 N 0.21688(16) 0.9749(3) 0.28573(14) 0.0393(8) Uani 1 1 d . . .
H2 H 0.1651 0.9796 0.2830 0.047 Uiso 1 1 calc R . .
N5 N 0.33018(17) 1.0681(4) 0.33735(15) 0.0459(9) Uani 1 1 d . . .
N4 N 0.30161(18) 0.6751(3) 0.14343(15) 0.0448(8) Uani 1 1 d . . .
C6 C 0.2526(2) 1.0656(4) 0.33296(17) 0.0382(9) Uani 1 1 d . . .
C11 C 0.2542(2) 0.8795(4) 0.24335(16) 0.0345(8) Uani 1 1 d . . .
C7 C 0.2031(2) 1.1523(4) 0.37324(18) 0.0435(10) Uani 1 1 d . . .
H7 H 0.1474 1.1489 0.3687 0.052 Uiso 1 1 calc R . .
C9 C 0.3195(2) 1.2442(5) 0.4248(2) 0.0517(11) Uani 1 1 d . . .
H9 H 0.3448 1.3048 0.4568 0.062 Uiso 1 1 calc R . .
C1 C 0.2253(2) 0.7014(4) 0.15417(17) 0.0398(9) Uani 1 1 d . . .
C8 C 0.2383(2) 1.2420(4) 0.41926(18) 0.0467(10) Uani 1 1 d . . .
H8 H 0.2069 1.3025 0.4473 0.056 Uiso 1 1 calc R . .
C10 C 0.3624(2) 1.1565(5) 0.3830(2) 0.0518(11) Uani 1 1 d . . .
H10 H 0.4183 1.1585 0.3866 0.062 Uiso 1 1 calc R . .
C2 C 0.1647(2) 0.6322(4) 0.11847(19) 0.0464(10) Uani 1 1 d . . .
H2A H 0.1107 0.6530 0.1274 0.056 Uiso 1 1 calc R . .
C4 C 0.2649(3) 0.5061(5) 0.0581(2) 0.0585(12) Uani 1 1 d . . .
H4 H 0.2804 0.4383 0.0246 0.070 Uiso 1 1 calc R . .
C5 C 0.3193(3) 0.5777(5) 0.0950(2) 0.0550(11) Uani 1 1 d . . .
H5 H 0.3735 0.5582 0.0863 0.066 Uiso 1 1 calc R . .
C3 C 0.1860(3) 0.5340(4) 0.07039(19) 0.0542(11) Uani 1 1 d . . .
H3 H 0.1466 0.4847 0.0453 0.065 Uiso 1 1 calc R . .
O4 O 0.0000 0.5050(6) 0.2500 0.0674(14) Uani 1 2 d S . .
O3 O 0.0031(3) 0.9044(7) 0.0558(3) 0.1185(19) Uani 1 1 d . . .
O6 O 0.0206(5) 1.3571(9) 0.4810(3) 0.133(2) Uani 1 1 d . . .
H6 H 0.021(4) 1.342(7) 0.447(3) 0.09(3) Uiso 1 1 d . . .
H13 H 0.005(3) 1.329(7) 0.324(3) 0.08(3) Uiso 1 1 d . . .
H14 H 0.007(3) 1.207(8) 0.334(3) 0.10(2) Uiso 1 1 d . . .
H16 H -0.008(5) 1.287(11) 0.483(5) 0.17(5) Uiso 1 1 d . . .
H12 H -0.025(9) 0.99(2) 0.059(9) 0.45(13) Uiso 1 1 d . . .
H17 H 0.007(3) 0.910(6) 0.092(2) 0.053(17) Uiso 1 1 d . . .
H15 H -0.013(6) 0.582(5) 0.251(6) 0.12(3) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.422(3) . ?
S1 O1 1.422(3) 4 ?
S1 O2 1.436(3) . ?
S1 O2 1.436(3) 4 ?
N1 C11 1.356(4) . ?
N1 C1 1.402(4) . ?
N3 C11 1.271(4) . ?
N2 C11 1.367(4) . ?
N2 C6 1.397(4) . ?
N5 C6 1.318(4) . ?
N5 C10 1.338(5) . ?
N4 C1 1.332(5) . ?
N4 C5 1.350(5) . ?
C6 C7 1.405(5) . ?
C7 C8 1.371(5) . ?
C9 C10 1.366(5) . ?
C9 C8 1.379(5) . ?
C1 C2 1.402(5) . ?
C2 C3 1.364(5) . ?
C4 C5 1.352(6) . ?
C4 C3 1.381(6) . ?

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
_geom_angle_publ_flag
O1 S1 O1 109.8(5) . 4 ?
O1 S1 O2 106.82(19) . . ?
O1 S1 O2 110.9(3) 4 . ?
O1 S1 O2 110.9(3) . 4 ?
O1 S1 O2 106.82(19) 4 4 ?
O2 S1 O2 111.7(3) . 4 ?
C11 N1 C1 126.8(3) . . ?
C11 N2 C6 126.6(3) . . ?
C6 N5 C10 117.7(3) . . ?
C1 N4 C5 116.7(3) . . ?
N5 C6 N2 119.3(3) . . ?
N5 C6 C7 123.1(3) . . ?
N2 C6 C7 117.7(3) . . ?
N3 C11 N1 123.6(3) . . ?
N3 C11 N2 122.6(3) . . ?
N1 C11 N2 113.8(3) . . ?
C8 C7 C6 117.6(3) . . ?
C10 C9 C8 118.0(4) . . ?
N4 C1 N1 118.5(3) . . ?
N4 C1 C2 123.2(3) . . ?
N1 C1 C2 118.3(3) . . ?
C7 C8 C9 119.9(4) . . ?
N5 C10 C9 123.8(4) . . ?
C3 C2 C1 117.5(4) . . ?
C5 C4 C3 118.3(4) . . ?
N4 C5 C4 124.1(4) . . ?
C2 C3 C4 120.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.060




_exptl_crystal_recrystallization_method 'Slow evaporation from water'
