#Electronic Supplementary Material for CrystEngComm
#This Journal is (c) The Royal Society of Chemistry 2007

data_General
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_audit_creation_date             2007-01-24
_audit_creation_method           'by CrystalStructure 3.6.0'

# SUBMISSION DETAILS

_publ_contact_author_name        'Dr. Peddy Vishweshwar'

_publ_contact_author_address     
;
Department of Analytical Research
Discovery Research
Dr. Reddy's Laboratories Ltd.
Miyapur
Hyderabad 500049
Andhrapradesh
INDIA
;

_publ_contact_author_email       vishweshwarp@drreddys.com
_publ_contact_author_fax         91-040-23045440
_publ_contact_author_phone       91-9866827284

#==============================================================================

# TITLE AND AUTHOR LIST

_publ_section_title              
;
Solid-State Structural Studies of Saccharin Salts with Some Heterocyclic Bases
;
_publ_section_title_footnote     
;
DRL Publication number:-635
;
loop_
_publ_author_name
_publ_author_address
P.Sudhakar
;
Department of Analytical Research
Discovery Research
Dr.Reddy's Laboratories Ltd.
Miyapur
Hyderabad 500049
Andhrapradesh
INDIA
;
'Vijay Kumar'
;
Department of Analytical Research
Discovery Research
Dr.Reddy's Laboratories Ltd.
Miyapur
Hyderabad 500049
Andhrapradesh
INDIA
;
P.Vishweshwar
;
Department of Analytical Research
Discovery Research
Dr.Reddy's Laboratories Ltd.
Miyapur
Hyderabad 500049
Andhrapradesh
INDIA
;
'J.Moses Babu'
;
Department of Analytical Research
Discovery Research
Dr.Reddy's Laboratories Ltd.
Miyapur
Hyderabad 500049
Andhrapradesh
INDIA
;
K.Vyas
;
Department of Analytical Research
Discovery Research
Dr.Reddy's Laboratories Ltd.
Miyapur
Hyderabad 500049
Andhrapradesh
INDIA
;

#==============================================================================

data_salt_1
_database_code_depnum_ccdc_archive 'CCDC 666292'

#==============================================================================

# CHEMICAL DATA

_chemical_name_common            
;
1,2-bis(4-pyridinium)ethane saccharinate (1:2)
;
_exptl_crystal_preparation       Methanol
_chemical_formula_sum            'C26 H22 N4 O6 S2'
_chemical_formula_moiety         'C12 H14 N2, 2(C7 H4 N O3 S)'
_chemical_formula_weight         550.60
_chemical_melting_point          494

#==============================================================================

# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z

#------------------------------------------------------------------------------

_cell_length_a                   7.5770(8)
_cell_length_b                   11.0722(13)
_cell_length_c                   15.260(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.809(11)
_cell_angle_gamma                90
_cell_volume                     1280.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6067
_cell_measurement_theta_min      1.3
_cell_measurement_theta_max      24.9
_cell_measurement_temperature    298

#------------------------------------------------------------------------------

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.33
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             572.00
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min  0.832
_exptl_absorpt_correction_T_max  0.918

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            11932
_diffrn_reflns_av_R_equivalents  0.074
_diffrn_reflns_theta_max         24.93
_diffrn_measured_fraction_theta_max 0.9886
_diffrn_reflns_theta_full        24.93
_diffrn_measured_fraction_theta_full 0.9886
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
Refinement using reflections with F² > 0.5 sigma(F²).
The weighted R-factor (wR) and goodness of fit (S) are based on F².
R-factor (gt) are based on F. The threshold expression of
F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2200
_reflns_number_gt                982
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1400
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1870
_refine_ls_number_parameters     186
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
115921.0000 163195.0000 49653.9000
;
_refine_ls_shift/su_max          0.0050
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.125 0.123
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#===============================================================================

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_solution    SIR92
_computing_structure_refinement  CRYSTALS
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_molecular_graphics    'X-seed 2.0'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
N2 N Uani 0.9265(3) 0.7824(3) 0.7811(2) 1.000 0.0427(10) . .
C8 C Uani 0.9275(4) 0.6655(3) 0.7614(2) 1.000 0.0444(12) . .
C9 C Uani 0.9190(4) 0.5789(3) 0.8269(2) 1.000 0.0423(12) . .
C10 C Uani 0.9127(4) 0.6146(3) 0.9141(2) 1.000 0.0384(10) . .
C11 C Uani 0.9101(5) 0.7364(3) 0.9322(2) 1.000 0.0527(12) . .
C12 C Uani 0.9160(5) 0.8202(3) 0.8647(2) 1.000 0.0530(14) . .
C13 C Uani 0.9069(4) 0.5211(3) 0.9863(2) 1.000 0.0433(12) . .
S1 S Uani 0.42984(9) 0.70517(7) 0.69652(5) 1.000 0.0383(3) . .
O1 O Uani 0.2639(3) 0.7066(3) 0.6492(2) 1.000 0.0581(8) . .
O2 O Uani 0.5721(3) 0.7675(2) 0.6532(2) 1.000 0.0520(10) . .
O3 O Uani 0.5301(3) 0.4553(2) 0.84690(10) 1.000 0.0481(9) . .
N1 N Uani 0.4862(4) 0.5692(2) 0.7233(2) 1.000 0.0430(10) . .
C1 C Uani 0.4930(4) 0.5535(3) 0.8105(2) 1.000 0.0350(12) . .
C2 C Uani 0.4500(3) 0.6660(3) 0.8615(2) 1.000 0.0327(8) . .
C3 C Uani 0.4489(4) 0.6834(3) 0.9523(2) 1.000 0.0423(12) . .
C4 C Uani 0.4071(5) 0.7974(4) 0.9834(2) 1.000 0.0577(16) . .
C5 C Uani 0.3620(5) 0.8918(4) 0.9262(3) 1.000 0.0583(12) . .
C6 C Uani 0.3616(4) 0.8748(3) 0.8356(2) 1.000 0.0460(12) . .
C7 C Uani 0.4074(4) 0.7613(3) 0.8053(2) 1.000 0.0334(10) . .
H8 H Uiso 0.93110 0.64120 0.70170 1.000 0.0530 calc R
H9 H Uiso 0.92170 0.49530 0.81280 1.000 0.0510 calc R
H11 H Uiso 0.90340 0.76290 0.99120 1.000 0.0630 calc R
H12 H Uiso 0.91450 0.90420 0.87730 1.000 0.0640 calc R
H21 H Uiso 0.925(5) 0.851(4) 0.731(3) 1.000 0.076(13) d .
H131 H Uiso 0.85070 0.55490 1.03590 1.000 0.0520 calc R
H132 H Uiso 0.84190 0.45280 0.96640 1.000 0.0520 calc R
H3 H Uiso 0.48040 0.61930 0.99090 1.000 0.0510 calc R
H4 H Uiso 0.40510 0.81090 1.04490 1.000 0.0690 calc R
H5 H Uiso 0.33270 0.96880 0.94920 1.000 0.0700 calc R
H6 H Uiso 0.33080 0.93790 0.79600 1.000 0.0550 calc R


#===============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.441(3) . . no
S1 O2 1.448(3) . . no
S1 N1 1.616(3) . . no
S1 C7 1.783(4) . . no
O3 C1 1.251(4) . . no
N2 C8 1.329(5) . . no
N2 C12 1.346(5) . . no
N2 H21 1.08(5) . . no
N1 C1 1.342(5) . . no
C8 C9 1.387(5) . . no
C9 C10 1.390(5) . . no
C10 C13 1.513(5) . . no
C10 C11 1.377(5) . . no
C11 C12 1.388(5) . . no
C13 C13 1.539(5) . 3_767 no
C8 H8 0.9500 . . no
C9 H9 0.9500 . . no
C11 H11 0.9500 . . no
C12 H12 0.9500 . . no
C13 H132 0.9500 . . no
C13 H131 0.9500 . . no
C1 C2 1.507(5) . . no
C2 C3 1.399(5) . . no
C2 C7 1.395(5) . . no
C3 C4 1.387(6) . . no
C4 C5 1.401(6) . . no
C5 C6 1.395(6) . . no
C6 C7 1.385(5) . . no
C3 H3 0.9500 . . no
C4 H4 0.9500 . . no
C5 H5 0.9500 . . no
C6 H6 0.9500 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 C7 96.76(15) . . . no
O1 S1 C7 111.64(16) . . . no
O1 S1 O2 114.58(17) . . . no
O1 S1 N1 111.26(17) . . . no
O2 S1 N1 111.34(15) . . . no
O2 S1 C7 109.90(16) . . . no
C8 N2 C12 121.2(3) . . . no
C8 N2 H21 122(2) . . . no
C12 N2 H21 117(2) . . . no
S1 N1 C1 112.2(2) . . . no
N2 C8 C9 120.7(3) . . . no
C8 C9 C10 119.7(3) . . . no
C11 C10 C13 121.6(3) . . . no
C9 C10 C11 118.1(3) . . . no
C9 C10 C13 120.3(3) . . . no
C10 C11 C12 120.4(3) . . . no
N2 C12 C11 119.9(3) . . . no
C10 C13 C13 111.7(3) . . 3_767 no
N2 C8 H8 120.00 . . . no
C9 C8 H8 120.00 . . . no
C10 C9 H9 120.00 . . . no
C8 C9 H9 121.00 . . . no
C12 C11 H11 120.00 . . . no
C10 C11 H11 120.00 . . . no
N2 C12 H12 120.00 . . . no
C11 C12 H12 120.00 . . . no
C10 C13 H131 109.00 . . . no
C10 C13 H132 109.00 . . . no
H131 C13 H132 109.00 . . . no
C13 C13 H131 109.00 3_767 . . no
C13 C13 H132 108.00 3_767 . . no
O3 C1 N1 123.9(3) . . . no
O3 C1 C2 122.5(3) . . . no
N1 C1 C2 113.5(3) . . . no
C1 C2 C3 129.0(3) . . . no
C1 C2 C7 111.0(3) . . . no
C3 C2 C7 120.0(3) . . . no
C2 C3 C4 118.0(3) . . . no
C3 C4 C5 121.4(3) . . . no
C4 C5 C6 120.9(4) . . . no
C5 C6 C7 117.1(3) . . . no
S1 C7 C2 106.5(2) . . . no
S1 C7 C6 130.9(2) . . . no
C2 C7 C6 122.6(3) . . . no
C2 C3 H3 120.00 . . . no
C4 C3 H3 122.00 . . . no
C3 C4 H4 119.00 . . . no
C5 C4 H4 119.00 . . . no
C4 C5 H5 120.00 . . . no
C6 C5 H5 119.00 . . . no
C5 C6 H6 122.00 . . . no
C7 C6 H6 121.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 C7 C6 -64.3(4) . . . . no
O2 S1 C7 C2 -114.7(2) . . . . no
O2 S1 C7 C6 64.0(3) . . . . no
N1 S1 C7 C2 0.9(2) . . . . no
N1 S1 C7 C6 179.7(3) . . . . no
O2 S1 N1 C1 114.6(3) . . . . no
C7 S1 N1 C1 0.1(3) . . . . no
O1 S1 C7 C2 117.0(2) . . . . no
O1 S1 N1 C1 -116.3(3) . . . . no
C8 N2 C12 C11 1.5(5) . . . . no
C12 N2 C8 C9 -0.5(4) . . . . no
S1 N1 C1 C2 -1.0(3) . . . . no
S1 N1 C1 O3 178.5(3) . . . . no
N2 C8 C9 C10 -1.2(5) . . . . no
C8 C9 C10 C11 1.8(5) . . . . no
C8 C9 C10 C13 -178.8(3) . . . . no
C9 C10 C13 C13 86.0(4) . . . 3_767 no
C9 C10 C11 C12 -0.8(5) . . . . no
C11 C10 C13 C13 -94.7(4) . . . 3_767 no
C13 C10 C11 C12 179.8(3) . . . . no
C10 C11 C12 N2 -0.8(5) . . . . no
C10 C13 C13 C10 -180.0(3) . . 3_767 3_767 no
O3 C1 C2 C3 2.3(5) . . . . no
O3 C1 C2 C7 -177.8(3) . . . . no
N1 C1 C2 C3 -178.1(3) . . . . no
N1 C1 C2 C7 1.7(4) . . . . no
C1 C2 C3 C4 178.9(3) . . . . no
C7 C2 C3 C4 -0.9(4) . . . . no
C1 C2 C7 S1 -1.5(3) . . . . no
C1 C2 C7 C6 179.6(3) . . . . no
C3 C2 C7 S1 178.4(2) . . . . no
C3 C2 C7 C6 -0.5(4) . . . . no
C2 C3 C4 C5 1.9(5) . . . . no
C3 C4 C5 C6 -1.5(6) . . . . no
C4 C5 C6 C7 0.0(5) . . . . no
C5 C6 C7 S1 -177.6(3) . . . . no
C5 C6 C7 C2 1.0(5) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 H11 3.1600 . 4_464 no
O1 C8 3.124(6) . 1_455 no
O2 C8 3.336(6) . . no
O3 N2 2.758(5) . 2_646 no
O3 C9 3.267(6) . . no
O1 H8 2.7500 . 1_455 no
O1 H11 2.6700 . 4_464 no
O2 H9 2.5800 . 2_656 no
O2 H132 2.8300 . 2_656 no
O2 H11 2.7900 . 4_464 no
O3 H21 1.70(4) . 2_646 no
O3 H3 2.6100 . 3_667 no
O3 H3 2.8800 . . no
N1 C12 3.159(6) . 2_646 no
N1 N2 3.245(6) . 2_646 no
N2 N1 3.245(6) . 2_656 no
N2 O3 2.758(5) . 2_656 no
N2 C1 3.370(6) . 2_656 no
N1 H6 2.8200 . 2_546 no
N1 H12 2.5100 . 2_646 no
N1 H21 2.60(4) . 2_646 no
C1 N2 3.370(6) . 2_646 no
C1 C9 3.246(6) . . no
C1 C10 3.596(6) . . no
C3 C11 3.561(7) . . no
C5 C12 3.583(7) . 1_455 no
C6 C12 3.465(7) . 1_455 no
C8 O2 3.336(6) . . no
C8 O1 3.124(6) . 1_655 no
C9 C1 3.246(6) . . no
C9 O3 3.267(6) . . no
C10 C1 3.596(6) . . no
C11 C3 3.561(7) . . no
C12 N1 3.159(6) . 2_656 no
C12 C6 3.465(7) . 1_655 no
C12 C5 3.583(7) . 1_655 no
C1 H21 2.41(4) . 2_646 no
C3 H132 2.9600 . 3_667 no
C9 H131 3.0900 . 3_767 no
H3 O3 2.8800 . . no
H3 O3 2.6100 . 3_667 no
H4 H8 2.4600 . 4_465 no
H6 N1 2.8200 . 2_556 no
H8 O1 2.7500 . 1_655 no
H8 H4 2.4600 . 4_564 no
H9 O2 2.5800 . 2_646 no
H9 H132 2.4700 . . no
H11 O2 2.7900 . 4_565 no
H11 H131 2.4400 . . no
H11 S1 3.1600 . 4_565 no
H11 O1 2.6700 . 4_565 no
H12 N1 2.5100 . 2_656 no
H21 N1 2.60(4) . 2_656 no
H21 O3 1.70(4) . 2_656 no
H21 C1 2.41(4) . 2_656 no
H131 C9 3.0900 . 3_767 no
H131 H11 2.4400 . . no
H132 C3 2.9600 . 3_667 no
H132 H9 2.4700 . . no
H132 O2 2.8300 . 2_646 no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N2 H21 O3 1.08(5) 1.70(4) 2.758(5) 168(3) 2_656 yes
C3 H3 O3 0.9500 2.6100 3.429(6) 144.00 3_667 yes
C9 H9 O2 0.9500 2.5800 3.462(6) 155.00 2_646 yes
C11 H11 O1 0.9500 2.6700 3.563(6) 157.00 4_565 yes
C12 H12 N1 0.9500 2.5100 3.159(6) 126.00 2_656 yes

#===END

# Attachment 'Salt_2.cif'

#==============================================================================

data_salt_2
_database_code_depnum_ccdc_archive 'CCDC 666293'

#==============================================================================

# CHEMICAL DATA
_chemical_name_common            
;
1,2-bis(4-pyridinium)ethylene saccharinate (1:2)
;
_exptl_crystal_preparation       Methanol
_chemical_formula_sum            'C26 H20 N4 O6 S2 '
_chemical_formula_moiety         'C12 H12 N2, 2(C7 H4 N O3 S)'
_chemical_formula_weight         548.59
_chemical_melting_point          507

#==============================================================================

# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

#------------------------------------------------------------------------------

_cell_length_a                   13.161(2)
_cell_length_b                   5.251(2)
_cell_length_c                   18.590(12)
_cell_angle_alpha                90
_cell_angle_beta                 106.828(3)
_cell_angle_gamma                90
_cell_volume                     1229.7(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4870
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      29.0
_cell_measurement_temperature    298

#------------------------------------------------------------------------------

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568.00
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.948

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            14736
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_theta_max         29.50
_diffrn_measured_fraction_theta_max 0.8825
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
Refinement using reflections with F² > 1.2 sigma(F²).
The weighted R-factor (wR) and goodness of fit (S) are based on F².
R-factor (gt) are based on F. The threshold expression of
F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3039
_reflns_number_gt                1454
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.0930
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_reflns         1842
_refine_ls_number_parameters     182
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
5342.9800 7406.6400 2203.0300
;
_refine_ls_shift/su_max          0.0000
_refine_diff_density_max         0.68
_refine_diff_density_min         -0.66
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.125 0.123
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#===============================================================================

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_solution    SIR92
_computing_structure_refinement  CRYSTALS
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_molecular_graphics    'X-seed 2.0'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
N2 N Uani 0.4787(2) -0.1564(6) 0.1621(2) 1.000 0.0451(12) . .
C8 C Uani 0.5765(3) -0.0692(8) 0.1729(2) 1.000 0.0499(14) . .
C9 C Uani 0.5961(3) 0.1276(8) 0.1301(2) 1.000 0.0465(14) . .
C10 C Uani 0.5145(3) 0.2367(8) 0.0740(2) 1.000 0.0369(12) . .
C11 C Uani 0.4125(3) 0.1338(8) 0.0638(2) 1.000 0.0467(14) . .
C12 C Uani 0.3977(3) -0.0587(8) 0.1082(2) 1.000 0.0499(14) . .
C13 C Uani 0.5356(3) 0.4455(8) 0.0285(2) 1.000 0.0417(12) . .
S1 S Uani 0.64686(7) 0.2311(2) 0.37025(6) 1.000 0.0489(3) . .
O1 O Uani 0.7212(2) 0.0730(7) 0.3466(2) 1.000 0.0707(14) . .
O2 O Uani 0.6918(2) 0.3710(6) 0.4391(2) 1.000 0.0636(12) . .
O3 O Uani 0.4132(2) 0.4825(6) 0.23130(10) 1.000 0.0503(12) . .
N1 N Uani 0.5838(2) 0.4191(7) 0.3023(2) 1.000 0.0448(12) . .
C1 C Uani 0.4807(3) 0.3684(8) 0.2832(2) 1.000 0.0410(12) . .
C2 C Uani 0.4485(3) 0.1601(7) 0.3263(2) 1.000 0.0371(12) . .
C3 C Uani 0.3478(3) 0.0698(8) 0.3209(2) 1.000 0.0466(14) . .
C4 C Uani 0.3382(3) -0.1285(9) 0.3678(2) 1.000 0.0540(16) . .
C5 C Uani 0.4273(3) -0.2321(9) 0.4179(2) 1.000 0.0562(16) . .
C6 C Uani 0.5278(3) -0.1426(8) 0.4235(2) 1.000 0.0485(12) . .
C7 C Uani 0.5360(3) 0.0556(8) 0.3779(2) 1.000 0.0396(12) . .
H2 H Uiso 0.46590 -0.28870 0.19330 1.000 0.0550 calc R
H8 H Uiso 0.63370 -0.14370 0.21030 1.000 0.0580 calc R
H9 H Uiso 0.66640 0.19010 0.13920 1.000 0.0540 calc R
H11 H Uiso 0.35370 0.20010 0.02590 1.000 0.0560 calc R
H12 H Uiso 0.32840 -0.12640 0.10040 1.000 0.0600 calc R
H13 H Uiso 0.60580 0.51100 0.04050 1.000 0.0490 calc R
H3 H Uiso 0.28690 0.14220 0.28630 1.000 0.0550 calc R
H4 H Uiso 0.26990 -0.19360 0.36540 1.000 0.0650 calc R
H5 H Uiso 0.41900 -0.36860 0.44930 1.000 0.0690 calc R
H6 H Uiso 0.58880 -0.21580 0.45780 1.000 0.0560 calc R


#===============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.446(4) . . no
S1 N1 1.629(4) . . no
S1 C7 1.766(5) . . no
S1 O1 1.445(4) . . no
O3 C1 1.258(5) . . no
N2 C8 1.326(5) . . no
N2 C12 1.336(5) . . no
N2 H2 0.9500 . . no
N1 C1 1.326(5) . . no
C8 C9 1.373(6) . . no
C9 C10 1.386(6) . . no
C10 C13 1.460(6) . . no
C10 C11 1.408(6) . . no
C11 C12 1.354(6) . . no
C13 C13 1.324(6) . 3_665 no
C8 H8 0.9500 . . no
C9 H9 0.9500 . . no
C11 H11 0.9500 . . no
C12 H12 0.9500 . . no
C13 H13 0.9500 . . no
C1 C2 1.488(6) . . no
C2 C3 1.384(6) . . no
C2 C7 1.381(6) . . no
C3 C4 1.387(6) . . no
C4 C5 1.381(6) . . no
C5 C6 1.379(6) . . no
C6 C7 1.366(6) . . no
C3 H3 0.9500 . . no
C4 H4 0.9500 . . no
C5 H5 0.9500 . . no
C6 H6 0.9500 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 110.49(19) . . . no
O1 S1 C7 111.9(2) . . . no
O2 S1 N1 111.39(19) . . . no
O2 S1 C7 109.25(18) . . . no
N1 S1 C7 97.55(17) . . . no
O1 S1 O2 114.95(19) . . . no
C8 N2 C12 120.7(3) . . . no
C12 N2 H2 120.00 . . . no
C8 N2 H2 120.00 . . . no
S1 N1 C1 109.8(3) . . . no
N2 C8 C9 120.6(4) . . . no
C8 C9 C10 120.8(4) . . . no
C11 C10 C13 123.0(3) . . . no
C9 C10 C11 116.3(4) . . . no
C9 C10 C13 120.7(4) . . . no
C10 C11 C12 120.3(4) . . . no
N2 C12 C11 121.3(4) . . . no
C10 C13 C13 125.4(4) . . 3_665 no
C9 C8 H8 120.00 . . . no
N2 C8 H8 120.00 . . . no
C8 C9 H9 120.00 . . . no
C10 C9 H9 120.00 . . . no
C10 C11 H11 120.00 . . . no
C12 C11 H11 120.00 . . . no
N2 C12 H12 120.00 . . . no
C11 C12 H12 119.00 . . . no
C10 C13 H13 118.00 . . . no
C13 C13 H13 117.00 3_665 . . no
O3 C1 N1 123.4(4) . . . no
O3 C1 C2 121.0(4) . . . no
N1 C1 C2 115.6(3) . . . no
C1 C2 C3 129.0(4) . . . no
C1 C2 C7 110.9(4) . . . no
C3 C2 C7 120.2(4) . . . no
C2 C3 C4 118.1(4) . . . no
C3 C4 C5 120.4(4) . . . no
C4 C5 C6 121.7(4) . . . no
C5 C6 C7 117.3(4) . . . no
S1 C7 C2 106.2(3) . . . no
S1 C7 C6 131.5(3) . . . no
C2 C7 C6 122.3(4) . . . no
C2 C3 H3 121.00 . . . no
C4 C3 H3 121.00 . . . no
C3 C4 H4 120.00 . . . no
C5 C4 H4 120.00 . . . no
C4 C5 H5 119.00 . . . no
C6 C5 H5 119.00 . . . no
C5 C6 H6 121.00 . . . no
C7 C6 H6 121.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 C7 C6 63.1(4) . . . . no
O2 S1 C7 C2 113.8(3) . . . . no
O2 S1 C7 C6 -65.3(4) . . . . no
N1 S1 C7 C2 -2.0(3) . . . . no
N1 S1 C7 C6 178.9(4) . . . . no
O2 S1 N1 C1 -112.9(3) . . . . no
C7 S1 N1 C1 1.3(3) . . . . no
O1 S1 C7 C2 -117.7(3) . . . . no
O1 S1 N1 C1 118.1(3) . . . . no
C8 N2 C12 C11 -0.9(6) . . . . no
C12 N2 C8 C9 1.6(6) . . . . no
S1 N1 C1 C2 -0.2(4) . . . . no
S1 N1 C1 O3 -178.8(3) . . . . no
N2 C8 C9 C10 -1.0(6) . . . . no
C8 C9 C10 C11 -0.3(6) . . . . no
C8 C9 C10 C13 -179.9(4) . . . . no
C9 C10 C13 C13 176.7(4) . . . 3_665 no
C9 C10 C11 C12 1.0(6) . . . . no
C11 C10 C13 C13 -2.9(6) . . . 3_665 no
C13 C10 C11 C12 -179.5(4) . . . . no
C10 C11 C12 N2 -0.4(6) . . . . no
C10 C13 C13 C10 -180.0(4) . . 3_665 3_665 no
O3 C1 C2 C3 -3.4(6) . . . . no
O3 C1 C2 C7 177.3(4) . . . . no
N1 C1 C2 C3 177.9(4) . . . . no
N1 C1 C2 C7 -1.4(5) . . . . no
C1 C2 C3 C4 -180.0(4) . . . . no
C7 C2 C3 C4 -0.8(6) . . . . no
C1 C2 C7 S1 2.1(4) . . . . no
C1 C2 C7 C6 -178.7(4) . . . . no
C3 C2 C7 S1 -177.3(3) . . . . no
C3 C2 C7 C6 2.0(6) . . . . no
C2 C3 C4 C5 -0.4(6) . . . . no
C3 C4 C5 C6 0.4(6) . . . . no
C4 C5 C6 C7 0.7(6) . . . . no
C5 C6 C7 S1 177.1(3) . . . . no
C5 C6 C7 C2 -1.9(6) . . . . no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N2 H2 O3 0.9500 1.6500 2.576(6) 165.00 1_545 yes
N2 H2 N1 0.9500 2.6500 3.404(7) 136.00 1_545 yes
C9 H9 O1 0.9500 2.4600 3.292(7) 146.00 2_655 yes
C11 H11 O2 0.9500 2.3000 3.148(7) 148.00 4_454 yes
C13 H13 O1 0.9500 2.6300 3.432(7) 142.00 2_655 yes
#==============================================================================

data_salt_3
_database_code_depnum_ccdc_archive 'CCDC 666294'

#==============================================================================

# CHEMICAL DATA

_exptl_crystal_preparation       'Methanol and water'
_chemical_formula_sum            'C18 H20 N4 O6 S2 '
_chemical_formula_moiety         'C4 H12 N2, 2(C7 H4 N O3 S)'
_chemical_formula_weight         452.50
_chemical_melting_point          524

#==============================================================================

# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z

#------------------------------------------------------------------------------

_cell_length_a                   11.1261(10)
_cell_length_b                   9.3971(8)
_cell_length_c                   9.6281(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.489(4)
_cell_angle_gamma                90.0000
_cell_volume                     992.88(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5600
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      27.4
_cell_measurement_temperature    298

#------------------------------------------------------------------------------

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472.00
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_T_max  0.939

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            10969
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_theta_max         27.44
_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
Refinement was performed using reflections with F² > 0.1 sigma(F²).
The weighted R-factor (wR) and goodness of fit (S) are based on F².
R-factor (gt) are based on F. The threshold expression of
F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2228
_reflns_number_gt                1893
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0530
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2200
_refine_ls_number_parameters     153
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
9708.1600 13375.9000 3748.9300
;
_refine_ls_shift/su_max          0.0000
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_extinction_coef       554(18)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.125 0.123
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
N2 N Uani 1.04605(13) 0.36466(16) 0.46595(15) 1.000 0.0320(4) . .
C8 C Uani 1.04626(15) 0.40662(18) 0.61493(17) 1.000 0.0326(5) . .
C9 C Uani 1.05586(14) 0.56587(17) 0.63026(17) 1.000 0.0335(5) . .
S1 S Uani 0.81544(3) 0.48204(4) 0.95433(4) 1.000 0.0298(1) . .
O1 O Uani 0.89426(11) 0.36368(13) 0.99923(14) 1.000 0.0438(4) . .
O2 O Uani 0.82229(10) 0.59550(13) 1.05569(13) 1.000 0.0394(3) . .
O3 O Uani 0.72450(10) 0.55155(14) 0.58052(12) 1.000 0.0431(4) . .
N1 N Uani 0.83296(11) 0.54026(16) 0.80265(14) 1.000 0.0376(4) . .
C1 C Uani 0.73163(13) 0.52143(18) 0.70731(16) 1.000 0.0324(4) . .
C2 C Uani 0.62841(13) 0.45596(17) 0.76733(17) 1.000 0.0308(4) . .
C3 C Uani 0.51090(14) 0.4264(2) 0.70150(18) 1.000 0.0395(5) . .
C4 C Uani 0.43382(15) 0.3574(2) 0.7795(2) 1.000 0.0442(6) . .
C5 C Uani 0.47215(15) 0.3199(2) 0.9171(2) 1.000 0.0432(5) . .
C6 C Uani 0.58933(15) 0.35121(18) 0.98521(18) 1.000 0.0375(5) . .
C7 C Uani 0.66405(13) 0.42121(17) 0.90659(17) 1.000 0.0302(4) . .
H21 H Uiso 1.1237(17) 0.394(2) 0.4436(19) 1.000 0.050(5) d .
H22 H Uiso 1.0364(17) 0.273(2) 0.459(2) 1.000 0.052(6) d .
H81 H Uiso 1.11290 0.36260 0.67360 1.000 0.0390 calc R
H82 H Uiso 0.97210 0.37610 0.64220 1.000 0.0390 calc R
H91 H Uiso 1.05270 0.59230 0.72480 1.000 0.0400 calc R
H92 H Uiso 1.13120 0.59600 0.60580 1.000 0.0400 calc R
H3 H Uiso 0.48420 0.45280 0.60620 1.000 0.0470 calc R
H4 H Uiso 0.35280 0.33610 0.73620 1.000 0.0530 calc R
H5 H Uiso 0.41800 0.27040 0.96680 1.000 0.0530 calc R
H6 H Uiso 0.61660 0.32680 1.08100 1.000 0.0460 calc R


#===============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4389(13) . . yes
S1 N1 1.6012(14) . . yes
S1 O1 1.4381(13) . . yes
S1 C7 1.7663(15) . . yes
O3 C1 1.2429(19) . . yes
N2 C9 1.491(2) . 3_766 yes
N2 C8 1.487(2) . . yes
N2 H21 0.964(19) . . no
N2 H22 0.869(19) . . no
N1 C1 1.343(2) . . yes
C8 C9 1.506(2) . . no
C8 H81 0.9500 . . no
C8 H82 0.9500 . . no
C9 H92 0.9500 . . no
C9 H91 0.9500 . . no
C1 C2 1.500(2) . . no
C2 C3 1.384(2) . . no
C2 C7 1.373(2) . . no
C3 C4 1.390(2) . . no
C4 C5 1.369(3) . . no
C5 C6 1.391(2) . . no
C6 C7 1.380(2) . . no
C3 H3 0.9500 . . no
C4 H4 0.9500 . . no
C5 H5 0.9500 . . no
C6 H6 0.9500 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 C7 110.97(7) . . . yes
N1 S1 C7 97.32(7) . . . yes
O1 S1 C7 109.64(7) . . . yes
O1 S1 O2 114.06(7) . . . yes
O1 S1 N1 112.24(8) . . . yes
O2 S1 N1 111.38(8) . . . yes
C8 N2 C9 111.30(13) . . 3_766 yes
C9 N2 H22 108.3(13) 3_766 . . no
C8 N2 H21 106.3(11) . . . no
C8 N2 H22 108.5(13) . . . no
H21 N2 H22 111.7(17) . . . no
C9 N2 H21 110.7(11) 3_766 . . no
S1 N1 C1 111.33(11) . . . yes
N2 C8 C9 110.29(13) . . . yes
N2 C9 C8 109.87(13) 3_766 . . yes
C9 C8 H81 110.00 . . . no
N2 C8 H81 110.00 . . . no
N2 C8 H82 109.00 . . . no
C9 C8 H82 109.00 . . . no
H81 C8 H82 109.00 . . . no
C8 C9 H91 110.00 . . . no
C8 C9 H92 109.00 . . . no
H91 C9 H92 109.00 . . . no
N2 C9 H91 110.00 3_766 . . no
N2 C9 H92 109.00 3_766 . . no
O3 C1 N1 123.49(14) . . . yes
O3 C1 C2 122.88(14) . . . yes
N1 C1 C2 113.61(13) . . . yes
C1 C2 C3 129.15(15) . . . no
C1 C2 C7 110.94(13) . . . no
C3 C2 C7 119.89(15) . . . no
C2 C3 C4 117.82(16) . . . no
C3 C4 C5 121.42(16) . . . no
C4 C5 C6 121.33(16) . . . no
C5 C6 C7 116.41(16) . . . no
S1 C7 C2 106.65(11) . . . yes
S1 C7 C6 130.27(13) . . . yes
C2 C7 C6 123.08(15) . . . no
C2 C3 H3 121.00 . . . no
C4 C3 H3 121.00 . . . no
C3 C4 H4 119.00 . . . no
C5 C4 H4 119.00 . . . no
C4 C5 H5 119.00 . . . no
C6 C5 H5 119.00 . . . no
C5 C6 H6 122.00 . . . no
C7 C6 H6 122.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 C7 C6 60.11(18) . . . . no
O2 S1 C7 C2 113.58(12) . . . . no
O2 S1 C7 C6 -66.79(18) . . . . no
O1 S1 N1 C1 115.23(12) . . . . no
O2 S1 N1 C1 -115.49(12) . . . . no
C7 S1 N1 C1 0.48(13) . . . . no
O1 S1 C7 C2 -119.53(12) . . . . no
N1 S1 C7 C2 -2.71(13) . . . . no
N1 S1 C7 C6 176.92(16) . . . . no
C9 N2 C8 C9 -57.79(17) 3_766 . . . no
C8 N2 C9 C8 57.55(17) . . 3_766 3_766 no
S1 N1 C1 O3 -176.36(14) . . . . no
S1 N1 C1 C2 1.79(18) . . . . no
N2 C8 C9 N2 56.95(17) . . . 3_766 no
O3 C1 C2 C3 -4.3(3) . . . . no
O3 C1 C2 C7 174.24(16) . . . . no
N1 C1 C2 C3 177.51(17) . . . . no
N1 C1 C2 C7 -3.9(2) . . . . no
C1 C2 C3 C4 176.42(17) . . . . no
C7 C2 C3 C4 -2.1(3) . . . . no
C1 C2 C7 S1 3.89(16) . . . . no
C1 C2 C7 C6 -175.78(15) . . . . no
C3 C2 C7 S1 -177.38(13) . . . . no
C3 C2 C7 C6 3.0(3) . . . . no
C2 C3 C4 C5 0.2(3) . . . . no
C3 C4 C5 C6 1.0(3) . . . . no
C4 C5 C6 C7 -0.2(3) . . . . no
C5 C6 C7 S1 178.64(14) . . . . no
C5 C6 C7 C2 -1.8(2) . . . . no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N2 H21 O3 0.964(19) 1.816(19) 2.7774(19) 174.5(17) 3_766 yes
N2 H21 N1 0.964(19) 2.572(18) 3.232(2) 125.8(14) 3_766 yes
N2 H22 O2 0.869(19) 2.312(19) 2.9474(19) 130.0(16) 2_746 yes
N2 H22 O1 0.869(19) 2.122(19) 2.782(2) 132.2(17) 4_554 yes
C5 H5 O3 0.9500 2.5900 3.341(2) 136.00 2_646 yes

# End of CIF

#==============================================================================
# Attachment 'Salt_4.cif'

#==============================================================================

data_Salt_4
_database_code_depnum_ccdc_archive 'CCDC 666295'

#==============================================================================

# CHEMICAL DATA
_chemical_name_common            
;
1,4-Dimethylpiperazinium saccharinate (1:2)
;
_exptl_crystal_preparation       Methanol
_chemical_formula_sum            'C20 H24 N4 O6 S2 '
_chemical_formula_moiety         'C6 H16 N2, 2(C7 H4 N O3 S)'
_chemical_formula_weight         480.55
_chemical_melting_point          489

#==============================================================================

# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z

#------------------------------------------------------------------------------

_cell_length_a                   7.973(2)
_cell_length_b                   15.413(3)
_cell_length_c                   9.293(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.555(10)
_cell_angle_gamma                90
_cell_volume                     1105.4(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4805
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      29.1
_cell_measurement_temperature    298

#------------------------------------------------------------------------------

_exptl_crystal_description       chip
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504.00
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_type   none

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            13339
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_theta_max         29.53
_diffrn_measured_fraction_theta_max 0.8733
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.9912
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
Refinement using reflections with F² > 1.2 sigma(F²).
The weighted R-factor (wR) and goodness of fit (S) are based on F².
R-factor (gt) are based on F. The threshold expression of
F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2686
_reflns_number_gt                1122
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.1270
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1658
_refine_ls_number_parameters     161
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
3262.6700 4518.6500 1354.5000
;
_refine_ls_shift/su_max          0.0000
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.49
_refine_ls_extinction_method     
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_extinction_coef       50.9(50)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.125 0.123
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#===============================================================================

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_solution    SIR92
_computing_structure_refinement  CRYSTALS
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_molecular_graphics    'X-seed 2.0'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
N2 N Uani -0.0959(6) 0.4759(3) 0.1069(5) 1.000 0.0414(16) . .
C8 C Uani -0.2595(8) 0.4636(5) 0.1565(7) 1.000 0.065(3) . .
C9 C Uani -0.0771(7) 0.5683(4) 0.0662(6) 1.000 0.0453(19) . .
C10 C Uani 0.0899(7) 0.5815(4) 0.0203(6) 1.000 0.0452(17) . .
S1 S Uani 0.1332(2) 0.35366(10) 0.4641(2) 1.000 0.0444(4) . .
O1 O Uani 0.0563(5) 0.4018(3) 0.5641(4) 1.000 0.0598(17) . .
O2 O Uani 0.0430(6) 0.2757(3) 0.4043(5) 1.000 0.0725(17) . .
O3 O Uani 0.4005(5) 0.4624(3) 0.2498(4) 1.000 0.0553(16) . .
N1 N Uani 0.1688(6) 0.4135(3) 0.3320(5) 1.000 0.0453(17) . .
C1 C Uani 0.3413(7) 0.4221(4) 0.3401(6) 1.000 0.0406(17) . .
C2 C Uani 0.4523(6) 0.3755(3) 0.4722(5) 1.000 0.0367(17) . .
C3 C Uani 0.6308(7) 0.3707(4) 0.5167(6) 1.000 0.0430(17) . .
C4 C Uani 0.7042(7) 0.3190(4) 0.6402(6) 1.000 0.0486(19) . .
C5 C Uani 0.6027(8) 0.2776(4) 0.7181(7) 1.000 0.056(2) . .
C6 C Uani 0.4234(7) 0.2831(4) 0.6753(6) 1.000 0.052(2) . .
C7 C Uani 0.3532(6) 0.3328(3) 0.5506(5) 1.000 0.0382(17) . .
H2 H Uiso -0.007(8) 0.467(4) 0.190(7) 1.000 0.08(2) d .
H81 H Uiso -0.24500 0.41820 0.22780 1.000 0.0800 calc R
H82 H Uiso -0.35140 0.44930 0.07300 1.000 0.0800 calc R
H83 H Uiso -0.28620 0.51600 0.19980 1.000 0.0800 calc R
H91 H Uiso -0.07730 0.60440 0.14900 1.000 0.0540 calc R
H92 H Uiso -0.17190 0.58340 -0.01440 1.000 0.0540 calc R
H101 H Uiso 0.18500 0.56790 0.10170 1.000 0.0530 calc R
H102 H Uiso 0.09780 0.64030 -0.00760 1.000 0.0530 calc R
H3 H Uiso 0.70120 0.40120 0.46500 1.000 0.0510 calc R
H4 H Uiso 0.82670 0.31350 0.67090 1.000 0.0550 calc R
H5 H Uiso 0.65700 0.24330 0.80170 1.000 0.0650 calc R
H6 H Uiso 0.35140 0.25520 0.72850 1.000 0.0610 calc R


#===============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.766(5) . . no
S1 N1 1.617(5) . . no
S1 O1 1.441(4) . . no
S1 O2 1.438(5) . . no
O3 C1 1.230(7) . . no
N2 C10 1.487(7) . 3_565 no
N2 C9 1.491(8) . . no
N2 C8 1.501(8) . . no
N2 H2 0.92(7) . . no
N1 C1 1.365(8) . . no
C9 C10 1.511(8) . . no
C8 H83 0.9500 . . no
C8 H81 0.9500 . . no
C8 H82 0.9500 . . no
C9 H91 0.9500 . . no
C9 H92 0.9500 . . no
C10 H102 0.9500 . . no
C10 H101 0.9500 . . no
C1 C2 1.503(7) . . no
C2 C3 1.381(8) . . no
C2 C7 1.370(7) . . no
C3 C4 1.399(8) . . no
C4 C5 1.371(9) . . no
C5 C6 1.387(9) . . no
C6 C7 1.385(7) . . no
C3 H3 0.9500 . . no
C4 H4 0.9500 . . no
C5 H5 0.9500 . . no
C6 H6 0.9500 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 C7 96.1(2) . . . no
O1 S1 C7 109.6(2) . . . no
O1 S1 O2 115.3(3) . . . no
O1 S1 N1 112.4(3) . . . no
O2 S1 N1 110.5(3) . . . no
O2 S1 C7 111.5(3) . . . no
C8 N2 C10 111.9(5) . . 3_565 no
C8 N2 C9 110.4(5) . . . no
C9 N2 C10 110.0(4) . . 3_565 no
C10 N2 H2 114(4) 3_565 . . no
C9 N2 H2 105(4) . . . no
C8 N2 H2 106(4) . . . no
S1 N1 C1 112.4(4) . . . no
N2 C9 C10 110.6(5) . . . no
N2 C10 C9 110.6(5) 3_565 . . no
N2 C8 H81 110.00 . . . no
H81 C8 H82 109.00 . . . no
N2 C8 H82 109.00 . . . no
N2 C8 H83 109.00 . . . no
H81 C8 H83 109.00 . . . no
H82 C8 H83 110.00 . . . no
C10 C9 H91 109.00 . . . no
N2 C9 H91 109.00 . . . no
N2 C9 H92 109.00 . . . no
C10 C9 H92 109.00 . . . no
H91 C9 H92 109.00 . . . no
C9 C10 H101 109.00 . . . no
C9 C10 H102 109.00 . . . no
H101 C10 H102 109.00 . . . no
N2 C10 H101 109.00 3_565 . . no
N2 C10 H102 109.00 3_565 . . no
O3 C1 N1 124.5(5) . . . no
O3 C1 C2 123.4(5) . . . no
N1 C1 C2 112.1(5) . . . no
C1 C2 C3 128.4(5) . . . no
C1 C2 C7 111.3(4) . . . no
C3 C2 C7 120.3(5) . . . no
C2 C3 C4 117.6(5) . . . no
C3 C4 C5 121.2(5) . . . no
C4 C5 C6 121.5(6) . . . no
C5 C6 C7 116.4(5) . . . no
S1 C7 C2 108.1(3) . . . no
S1 C7 C6 128.9(4) . . . no
C2 C7 C6 123.0(5) . . . no
C2 C3 H3 121.00 . . . no
C4 C3 H3 121.00 . . . no
C3 C4 H4 119.00 . . . no
C5 C4 H4 120.00 . . . no
C4 C5 H5 119.00 . . . no
C6 C5 H5 120.00 . . . no
C5 C6 H6 123.00 . . . no
C7 C6 H6 121.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 S1 N1 C1 0.5(4) . . . . no
O1 S1 C7 C2 -115.6(4) . . . . no
O1 S1 C7 C6 64.3(5) . . . . no
O2 S1 C7 C2 115.5(4) . . . . no
O2 S1 C7 C6 -64.5(6) . . . . no
O1 S1 N1 C1 114.6(4) . . . . no
O2 S1 N1 C1 -115.2(4) . . . . no
N1 S1 C7 C6 -179.3(5) . . . . no
N1 S1 C7 C2 0.7(4) . . . . no
C10 N2 C9 C10 -57.6(6) 3_565 . . . no
C8 N2 C9 C10 178.4(4) . . . . no
C8 N2 C10 C9 -179.3(5) . . 3_565 3_565 no
C9 N2 C10 C9 57.6(6) . . 3_565 3_565 no
S1 N1 C1 O3 177.8(5) . . . . no
S1 N1 C1 C2 -1.5(6) . . . . no
N2 C9 C10 N2 58.0(6) . . . 3_565 no
O3 C1 C2 C3 1.4(9) . . . . no
O3 C1 C2 C7 -177.3(5) . . . . no
N1 C1 C2 C3 -179.2(5) . . . . no
N1 C1 C2 C7 2.1(6) . . . . no
C1 C2 C3 C4 -176.6(5) . . . . no
C7 C2 C3 C4 2.0(8) . . . . no
C1 C2 C7 S1 -1.6(5) . . . . no
C1 C2 C7 C6 178.4(5) . . . . no
C3 C2 C7 S1 179.6(4) . . . . no
C3 C2 C7 C6 -0.4(8) . . . . no
C2 C3 C4 C5 -2.8(9) . . . . no
C3 C4 C5 C6 2.0(9) . . . . no
C4 C5 C6 C7 -0.3(9) . . . . no
C5 C6 C7 S1 179.6(4) . . . . no
C5 C6 C7 C2 -0.5(8) . . . . no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N2 H2 N1 0.92(7) 1.86(6) 2.745(7) 162(6) . yes
C9 H92 O3 0.9500 2.5700 3.419(7) 149.00 3_565 yes
C10 H101 O3 0.9500 2.5100 3.376(7) 151.00 . yes
C4 H4 O1 0.9500 2.6600 3.318(7) 126.00 1_655 yes

#===END

# Attachment 'Salt_5.cif'

#==============================================================================

data_salt_5
_database_code_depnum_ccdc_archive 'CCDC 666296'

#==============================================================================

# CHEMICAL DATA
_chemical_name_common            
;
2,2'-dipyridiniumamine saccharinate (1:1)
;
_exptl_crystal_preparation       Methanol
_chemical_formula_sum            'C17 H14 N4 O3 S '
_chemical_formula_moiety         'C10 H10 N3, C7 H4 N O3 S'
_chemical_formula_weight         354.38
_chemical_melting_point          487

#==============================================================================

# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z

#------------------------------------------------------------------------------

_cell_length_a                   9.635(2)
_cell_length_b                   13.385(4)
_cell_length_c                   14.149(3)
_cell_angle_alpha                105.658(3)
_cell_angle_beta                 91.773(2)
_cell_angle_gamma                110.444(2)
_cell_volume                     1630.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7273
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      27.5
_cell_measurement_temperature    298

#------------------------------------------------------------------------------

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736.00
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  0.911

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            18611
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_theta_max         27.51
_diffrn_measured_fraction_theta_max 0.9499
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.9788
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
Refinement using reflections with F² > 2.0 sigma(F²).
The weighted R-factor (wR) and goodness of fit (S) are based on F².
R-factor (gt) are based on F. The threshold expression of
F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             7134
_reflns_number_gt                5053
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.0520
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         5095
_refine_ls_number_parameters     492
_refine_ls_goodness_of_fit_ref   1.255
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
11927.4000 16505.4000 5060.7700
;
_refine_ls_shift/su_max          0.0080
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_extinction_coef       293.1(20)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.125 0.123
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#===============================================================================

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_solution    SIR92
_computing_structure_refinement  CRYSTALS
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_molecular_graphics    'X-seed 2.0'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
N3 N Uani 0.3314(2) 0.02698(13) 0.13219(12) 1.000 0.0618(6) . .
N4 N Uani 0.5339(2) -0.03000(10) 0.11371(12) 1.000 0.0602(6) . .
N5 N Uani 0.6101(2) 0.16230(10) 0.13407(11) 1.000 0.0563(6) . .
C15 C Uani 0.3842(2) -0.0536(2) 0.12523(13) 1.000 0.0547(7) . .
C16 C Uani 0.2961(3) -0.1592(2) 0.1299(2) 1.000 0.0683(9) . .
C17 C Uani 0.1495(3) -0.1799(2) 0.1415(2) 1.000 0.0793(10) . .
C18 C Uani 0.0937(3) -0.0966(2) 0.1480(2) 1.000 0.0784(12) . .
C19 C Uani 0.1875(3) 0.0045(2) 0.1433(2) 1.000 0.0695(8) . .
C20 C Uani 0.6432(2) 0.0707(2) 0.12273(13) 1.000 0.0551(7) . .
C21 C Uani 0.7926(3) 0.0816(2) 0.1196(2) 1.000 0.0718(10) . .
C22 C Uani 0.8991(3) 0.1835(2) 0.1302(2) 1.000 0.0823(10) . .
C23 C Uani 0.8612(3) 0.2764(2) 0.1433(2) 1.000 0.0753(10) . .
C24 C Uani 0.7159(2) 0.2633(2) 0.1444(2) 1.000 0.0656(7) . .
N6 N Uani 0.2839(2) -0.00135(12) 0.40164(11) 1.000 0.0498(5) . .
N7 N Uani 0.5321(2) 0.05703(13) 0.37305(11) 1.000 0.0515(5) . .
N8 N Uani 0.4436(2) -0.13035(13) 0.37179(11) 1.000 0.0506(5) . .
C25 C Uani 0.4013(2) 0.07780(10) 0.38628(12) 1.000 0.0455(6) . .
C26 C Uani 0.3987(2) 0.1802(2) 0.38200(10) 1.000 0.0593(7) . .
C27 C Uani 0.2697(3) 0.1999(2) 0.3960(2) 1.000 0.0676(10) . .
C28 C Uani 0.1472(2) 0.1185(2) 0.4132(2) 1.000 0.0650(7) . .
C29 C Uani 0.1583(2) 0.0200(2) 0.41400(10) 1.000 0.0575(7) . .
C30 C Uani 0.5529(2) -0.0403(2) 0.36253(11) 1.000 0.0455(6) . .
C31 C Uani 0.6907(2) -0.0484(2) 0.34035(13) 1.000 0.0575(7) . .
C32 C Uani 0.7075(2) -0.1478(2) 0.32870(10) 1.000 0.0652(9) . .
C33 C Uani 0.5911(3) -0.2397(2) 0.3377(2) 1.000 0.0708(10) . .
C34 C Uani 0.4614(2) -0.2284(2) 0.3598(2) 1.000 0.0648(6) . .
S1 S Uani -0.02353(6) 0.32286(4) 0.63703(3) 1.000 0.0534(2) . .
O1 O Uani -0.0693(2) 0.39474(13) 0.71423(10) 1.000 0.0764(6) . .
O2 O Uani 0.0420(2) 0.25472(12) 0.67043(11) 1.000 0.0733(6) . .
O3 O Uani -0.21220(10) 0.23193(11) 0.38369(10) 1.000 0.0608(4) . .
N1 N Uani -0.1582(2) 0.24860(12) 0.54756(11) 1.000 0.0537(5) . .
C1 C Uani 0.0239(2) 0.36485(13) 0.47464(12) 1.000 0.0401(5) . .
C2 C Uani 0.0934(2) 0.40880(10) 0.40300(10) 1.000 0.0525(7) . .
C3 C Uani 0.2372(2) 0.4855(2) 0.4284(2) 1.000 0.0662(9) . .
C4 C Uani 0.3111(2) 0.5188(2) 0.5235(2) 1.000 0.0741(9) . .
C5 C Uani 0.2424(2) 0.4767(2) 0.5964(2) 1.000 0.0650(7) . .
C6 C Uani 0.0983(2) 0.39980(13) 0.56965(13) 1.000 0.0456(6) . .
C7 C Uani -0.1270(2) 0.27656(13) 0.46423(13) 1.000 0.0438(5) . .
S2 S Uani 0.36424(6) 0.35837(5) 0.16057(4) 1.000 0.0623(2) . .
O4 O Uani 0.2460(2) 0.3082(2) 0.21217(11) 1.000 0.0940(8) . .
O5 O Uani 0.4986(2) 0.4373(2) 0.22226(12) 1.000 0.1006(6) . .
O6 O Uani 0.3710(2) 0.20290(10) -0.09253(11) 1.000 0.0953(8) . .
N2 N Uani 0.3967(2) 0.26430(10) 0.07705(13) 1.000 0.0656(7) . .
C8 C Uani 0.3044(2) 0.35810(10) -0.01357(13) 1.000 0.0493(6) . .
C9 C Uani 0.2552(3) 0.3829(2) -0.0944(2) 1.000 0.0684(9) . .
C10 C Uani 0.2012(3) 0.4681(2) -0.0768(2) 1.000 0.0734(10) . .
C11 C Uani 0.1965(3) 0.5266(2) 0.0187(2) 1.000 0.0774(10) . .
C12 C Uani 0.2453(2) 0.5033(2) 0.0994(2) 1.000 0.0703(6) . .
C13 C Uani 0.2994(2) 0.41760(10) 0.08040(13) 1.000 0.0495(6) . .
C14 C Uani 0.3599(2) 0.2669(2) -0.0134(2) 1.000 0.0599(6) . .
H16 H Uiso 0.33720 -0.21510 0.12480 1.000 0.0820 calc R
H17 H Uiso 0.08720 -0.25090 0.14590 1.000 0.0920 calc R
H18 H Uiso -0.00830 -0.11020 0.15550 1.000 0.0930 calc R
H19 H Uiso 0.14870 0.06160 0.14730 1.000 0.0860 calc R
H21 H Uiso 0.81920 0.01800 0.11100 1.000 0.0920 calc R
H22 H Uiso 1.00040 0.19030 0.12770 1.000 0.0990 calc R
H23 H Uiso 0.93630 0.34780 0.15150 1.000 0.0880 calc R
H24 H Uiso 0.68790 0.32610 0.15230 1.000 0.0770 calc R
H41 H Uiso 0.576(3) -0.092(2) 0.098(2) 1.000 0.094(7) d .
H51 H Uiso 0.507(2) 0.142(2) 0.1358(13) 1.000 0.059(6) d .
H26 H Uiso 0.48440 0.23460 0.36950 1.000 0.0700 calc R
H27 H Uiso 0.26430 0.26870 0.39350 1.000 0.0850 calc R
H28 H Uiso 0.05730 0.13120 0.42470 1.000 0.0810 calc R
H29 H Uiso 0.07260 -0.03700 0.42340 1.000 0.0700 calc R
H31 H Uiso 0.77050 0.01440 0.33370 1.000 0.0670 calc R
H32 H Uiso 0.80020 -0.15390 0.31380 1.000 0.0820 calc R
H33 H Uiso 0.60380 -0.30880 0.32900 1.000 0.0950 calc R
H34 H Uiso 0.38120 -0.29080 0.36680 1.000 0.0860 calc R
H71 H Uiso 0.618(2) 0.116(2) 0.3720(10) 1.000 0.075(7) d .
H81 H Uiso 0.367(2) -0.111(2) 0.392(2) 1.000 0.080(7) d .
H2 H Uiso 0.04270 0.38600 0.33770 1.000 0.0640 calc R
H3 H Uiso 0.28630 0.51660 0.37990 1.000 0.0780 calc R
H4 H Uiso 0.41120 0.57140 0.53910 1.000 0.0800 calc R
H5 H Uiso 0.29220 0.49950 0.66200 1.000 0.0710 calc R
H9 H Uiso 0.25850 0.34230 -0.16010 1.000 0.0850 calc R
H10 H Uiso 0.16640 0.48640 -0.13100 1.000 0.0900 calc R
H11 H Uiso 0.15910 0.58510 0.02870 1.000 0.0940 calc R
H12 H Uiso 0.24250 0.54410 0.16520 1.000 0.0820 calc R


#===============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4389(19) . . no
S1 N1 1.6101(18) . . no
S1 O1 1.4395(18) . . no
S1 C6 1.7613(19) . . no
S2 C13 1.7587(19) . . no
S2 O4 1.437(2) . . no
S2 N2 1.6045(19) . . no
S2 O5 1.425(2) . . no
O3 C7 1.250(2) . . no
O6 C14 1.246(3) . . no
N3 C19 1.336(4) . . no
N3 C15 1.327(3) . . no
N4 C20 1.360(3) . . no
N4 C15 1.390(3) . . no
N5 C24 1.345(3) . . no
N5 C20 1.342(3) . . no
N4 H41 1.02(3) . . no
N5 H51 0.94(2) . . no
N6 C25 1.323(2) . . no
N6 C29 1.343(3) . . no
N7 C30 1.356(3) . . no
N7 C25 1.390(3) . . no
N8 C34 1.349(3) . . no
N8 C30 1.336(3) . . no
N7 H71 0.93(2) . . no
N8 H81 0.90(2) . . no
N1 C7 1.342(2) . . no
N2 C14 1.330(3) . . no
C15 C16 1.392(4) . . no
C16 C17 1.365(4) . . no
C17 C18 1.381(4) . . no
C18 C19 1.360(4) . . no
C20 C21 1.399(4) . . no
C21 C22 1.356(4) . . no
C22 C23 1.382(4) . . no
C23 C24 1.350(4) . . no
C16 H16 0.9500 . . no
C17 H17 0.9500 . . no
C18 H18 0.9500 . . no
C19 H19 0.9500 . . no
C21 H21 0.9500 . . no
C22 H22 0.9500 . . no
C23 H23 0.9500 . . no
C24 H24 0.9500 . . no
C25 C26 1.397(3) . . no
C26 C27 1.367(4) . . no
C27 C28 1.379(4) . . no
C28 C29 1.363(4) . . no
C30 C31 1.408(3) . . no
C31 C32 1.363(4) . . no
C32 C33 1.385(4) . . no
C33 C34 1.347(4) . . no
C26 H26 0.9500 . . no
C27 H27 0.9500 . . no
C28 H28 0.9500 . . no
C29 H29 0.9500 . . no
C31 H31 0.9500 . . no
C32 H32 0.9500 . . no
C33 H33 0.9500 . . no
C34 H34 0.9500 . . no
C1 C7 1.492(3) . . no
C1 C6 1.381(2) . . no
C1 C2 1.382(2) . . no
C2 C3 1.371(3) . . no
C3 C4 1.383(4) . . no
C4 C5 1.384(4) . . no
C5 C6 1.375(3) . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C4 H4 0.9500 . . no
C5 H5 0.9500 . . no
C8 C9 1.387(3) . . no
C8 C13 1.365(3) . . no
C8 C14 1.495(3) . . no
C9 C10 1.379(4) . . no
C10 C11 1.378(4) . . no
C11 C12 1.372(4) . . no
C12 C13 1.386(3) . . no
C9 H9 0.9500 . . no
C10 H10 0.9500 . . no
C11 H11 0.9500 . . no
C12 H12 0.9500 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 C6 109.99(10) . . . no
N1 S1 C6 97.33(9) . . . no
O1 S1 N1 111.13(11) . . . no
O1 S1 C6 111.10(9) . . . no
O1 S1 O2 114.57(9) . . . no
O2 S1 N1 111.43(9) . . . no
O4 S2 N2 110.73(11) . . . no
O4 S2 C13 110.08(11) . . . no
O4 S2 O5 115.19(11) . . . no
N2 S2 C13 97.31(9) . . . no
O5 S2 N2 111.30(11) . . . no
O5 S2 C13 110.81(12) . . . no
C15 N3 C19 118.1(2) . . . no
C15 N4 C20 128.52(19) . . . no
C20 N5 C24 122.1(2) . . . no
C15 N4 H41 120.8(16) . . . no
C20 N4 H41 110.7(16) . . . no
C24 N5 H51 129.7(16) . . . no
C20 N5 H51 108.2(16) . . . no
C25 N6 C29 117.35(18) . . . no
C25 N7 C30 128.20(18) . . . no
C30 N8 C34 121.9(2) . . . no
C25 N7 H71 117.9(14) . . . no
C30 N7 H71 113.9(14) . . . no
C34 N8 H81 129.1(17) . . . no
C30 N8 H81 108.7(17) . . . no
S1 N1 C7 111.17(14) . . . no
S2 N2 C14 111.25(15) . . . no
N3 C15 N4 118.0(2) . . . no
N3 C15 C16 122.6(2) . . . no
N4 C15 C16 119.4(2) . . . no
C15 C16 C17 118.1(2) . . . no
C16 C17 C18 119.5(3) . . . no
C17 C18 C19 118.7(3) . . . no
N3 C19 C18 123.0(3) . . . no
N4 C20 N5 120.70(19) . . . no
N4 C20 C21 121.1(2) . . . no
N5 C20 C21 118.2(2) . . . no
C20 C21 C22 119.6(3) . . . no
C21 C22 C23 120.6(3) . . . no
C22 C23 C24 118.6(3) . . . no
N5 C24 C23 120.9(2) . . . no
C15 C16 H16 121.00 . . . no
C17 C16 H16 121.00 . . . no
C18 C17 H17 121.00 . . . no
C16 C17 H17 120.00 . . . no
C17 C18 H18 120.00 . . . no
C19 C18 H18 121.00 . . . no
C18 C19 H19 119.00 . . . no
N3 C19 H19 118.00 . . . no
C20 C21 H21 120.00 . . . no
C22 C21 H21 120.00 . . . no
C23 C22 H22 120.00 . . . no
C21 C22 H22 119.00 . . . no
C24 C23 H23 121.00 . . . no
C22 C23 H23 120.00 . . . no
C23 C24 H24 120.00 . . . no
N5 C24 H24 120.00 . . . no
N6 C25 C26 122.90(19) . . . no
N7 C25 C26 118.96(16) . . . no
N6 C25 N7 118.14(15) . . . no
C25 C26 C27 118.3(2) . . . no
C26 C27 C28 119.2(2) . . . no
C27 C28 C29 118.6(2) . . . no
N6 C29 C28 123.5(2) . . . no
N7 C30 C31 120.2(2) . . . no
N7 C30 N8 121.1(2) . . . no
N8 C30 C31 118.7(2) . . . no
C30 C31 C32 118.8(2) . . . no
C31 C32 C33 120.8(2) . . . no
C32 C33 C34 118.6(2) . . . no
N8 C34 C33 121.1(2) . . . no
C27 C26 H26 121.00 . . . no
C25 C26 H26 121.00 . . . no
C26 C27 H27 120.00 . . . no
C28 C27 H27 120.00 . . . no
C29 C28 H28 121.00 . . . no
C27 C28 H28 121.00 . . . no
N6 C29 H29 118.00 . . . no
C28 C29 H29 118.00 . . . no
C32 C31 H31 121.00 . . . no
C30 C31 H31 120.00 . . . no
C31 C32 H32 119.00 . . . no
C33 C32 H32 120.00 . . . no
C32 C33 H33 120.00 . . . no
C34 C33 H33 121.00 . . . no
C33 C34 H34 119.00 . . . no
N8 C34 H34 120.00 . . . no
C2 C1 C6 120.02(17) . . . no
C2 C1 C7 128.62(15) . . . no
C6 C1 C7 111.31(15) . . . no
C1 C2 C3 118.44(17) . . . no
C2 C3 C4 121.0(2) . . . no
C3 C4 C5 121.3(2) . . . no
C4 C5 C6 117.0(2) . . . no
S1 C6 C5 131.19(17) . . . no
S1 C6 C1 106.46(14) . . . no
C1 C6 C5 122.28(19) . . . no
N1 C7 C1 113.69(16) . . . no
O3 C7 N1 124.45(18) . . . no
O3 C7 C1 121.83(16) . . . no
C1 C2 H2 121.00 . . . no
C3 C2 H2 121.00 . . . no
C2 C3 H3 119.00 . . . no
C4 C3 H3 120.00 . . . no
C3 C4 H4 119.00 . . . no
C5 C4 H4 119.00 . . . no
C4 C5 H5 122.00 . . . no
C6 C5 H5 121.00 . . . no
C9 C8 C13 120.16(18) . . . no
C9 C8 C14 128.3(2) . . . no
C13 C8 C14 111.52(17) . . . no
C8 C9 C10 118.2(2) . . . no
C9 C10 C11 120.6(3) . . . no
C10 C11 C12 121.9(3) . . . no
C11 C12 C13 116.8(2) . . . no
S2 C13 C8 106.36(12) . . . no
S2 C13 C12 131.21(16) . . . no
C8 C13 C12 122.38(18) . . . no
O6 C14 N2 125.6(2) . . . no
O6 C14 C8 120.9(2) . . . no
N2 C14 C8 113.5(2) . . . no
C8 C9 H9 121.00 . . . no
C10 C9 H9 121.00 . . . no
C9 C10 H10 120.00 . . . no
C11 C10 H10 120.00 . . . no
C10 C11 H11 119.00 . . . no
C12 C11 H11 119.00 . . . no
C11 C12 H12 122.00 . . . no
C13 C12 H12 122.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C6 C5 -59.4(2) . . . . no
N1 S1 C6 C1 1.54(15) . . . . no
N1 S1 C6 C5 -175.4(2) . . . . no
O2 S1 N1 C7 -116.95(15) . . . . no
C6 S1 N1 C7 -2.07(16) . . . . no
O1 S1 C6 C1 -114.52(14) . . . . no
O1 S1 C6 C5 68.5(2) . . . . no
O2 S1 C6 C1 117.56(14) . . . . no
O1 S1 N1 C7 113.96(15) . . . . no
O5 S2 C13 C8 116.70(14) . . . . no
O4 S2 N2 C14 113.12(17) . . . . no
O5 S2 N2 C14 -117.39(18) . . . . no
C13 S2 N2 C14 -1.64(17) . . . . no
O4 S2 C13 C8 -114.71(15) . . . . no
O4 S2 C13 C12 62.6(2) . . . . no
O5 S2 C13 C12 -66.0(2) . . . . no
N2 S2 C13 C8 0.56(14) . . . . no
N2 S2 C13 C12 177.8(2) . . . . no
C19 N3 C15 N4 -180.0(2) . . . . no
C19 N3 C15 C16 -0.6(3) . . . . no
C15 N3 C19 C18 0.2(4) . . . . no
C20 N4 C15 C16 -168.8(2) . . . . no
C15 N4 C20 N5 -7.8(3) . . . . no
C15 N4 C20 C21 172.7(2) . . . . no
C20 N4 C15 N3 10.6(3) . . . . no
C20 N5 C24 C23 0.3(4) . . . . no
C24 N5 C20 N4 179.17(19) . . . . no
C24 N5 C20 C21 -1.4(3) . . . . no
C29 N6 C25 C26 -0.4(2) . . . . no
C29 N6 C25 N7 -179.82(14) . . . . no
C25 N6 C29 C28 -1.2(3) . . . . no
C30 N7 C25 C26 -171.29(15) . . . . no
C25 N7 C30 N8 -5.3(3) . . . . no
C25 N7 C30 C31 173.95(16) . . . . no
C30 N7 C25 N6 8.2(3) . . . . no
C30 N8 C34 C33 -0.1(4) . . . . no
C34 N8 C30 N7 178.78(19) . . . . no
C34 N8 C30 C31 -0.5(3) . . . . no
S1 N1 C7 O3 179.92(15) . . . . no
S1 N1 C7 C1 2.0(2) . . . . no
S2 N2 C14 O6 -179.1(2) . . . . no
S2 N2 C14 C8 2.2(2) . . . . no
N4 C15 C16 C17 179.8(2) . . . . no
N3 C15 C16 C17 0.4(3) . . . . no
C15 C16 C17 C18 0.1(4) . . . . no
C16 C17 C18 C19 -0.5(4) . . . . no
C17 C18 C19 N3 0.3(4) . . . . no
N5 C20 C21 C22 1.5(3) . . . . no
N4 C20 C21 C22 -179.1(2) . . . . no
C20 C21 C22 C23 -0.5(4) . . . . no
C21 C22 C23 C24 -0.6(4) . . . . no
C22 C23 C24 N5 0.7(4) . . . . no
N7 C25 C26 C27 -179.44(18) . . . . no
N6 C25 C26 C27 1.1(3) . . . . no
C25 C26 C27 C28 -0.4(3) . . . . no
C26 C27 C28 C29 -1.1(4) . . . . no
C27 C28 C29 N6 1.9(3) . . . . no
N7 C30 C31 C32 -178.99(15) . . . . no
N8 C30 C31 C32 0.3(2) . . . . no
C30 C31 C32 C33 0.5(3) . . . . no
C31 C32 C33 C34 -1.0(3) . . . . no
C32 C33 C34 N8 0.8(4) . . . . no
C2 C1 C6 C5 -1.1(3) . . . . no
C7 C1 C6 S1 -0.62(19) . . . . no
C7 C1 C6 C5 176.70(19) . . . . no
C2 C1 C7 O3 -1.3(3) . . . . no
C6 C1 C2 C3 1.1(3) . . . . no
C7 C1 C2 C3 -176.2(2) . . . . no
C2 C1 C6 S1 -178.40(14) . . . . no
C6 C1 C7 N1 -0.8(2) . . . . no
C2 C1 C7 N1 176.72(19) . . . . no
C6 C1 C7 O3 -178.81(17) . . . . no
C1 C2 C3 C4 -0.4(3) . . . . no
C2 C3 C4 C5 -0.5(4) . . . . no
C3 C4 C5 C6 0.6(4) . . . . no
C4 C5 C6 S1 176.81(18) . . . . no
C4 C5 C6 C1 0.2(3) . . . . no
C13 C8 C9 C10 -0.3(4) . . . . no
C14 C8 C9 C10 176.6(2) . . . . no
C9 C8 C13 S2 177.99(18) . . . . no
C9 C8 C13 C12 0.4(3) . . . . no
C14 C8 C13 S2 0.56(19) . . . . no
C14 C8 C13 C12 -177.00(19) . . . . no
C9 C8 C14 O6 2.2(4) . . . . no
C9 C8 C14 N2 -179.0(2) . . . . no
C13 C8 C14 O6 179.4(2) . . . . no
C13 C8 C14 N2 -1.8(3) . . . . no
C8 C9 C10 C11 0.0(4) . . . . no
C9 C10 C11 C12 0.3(4) . . . . no
C10 C11 C12 C13 -0.2(4) . . . . no
C11 C12 C13 S2 -177.06(19) . . . . no
C11 C12 C13 C8 -0.2(3) . . . . no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N4 H41 O6 1.02(3) 1.72(3) 2.722(2) 168(2) 2_655 yes
N5 H51 N3 0.94(2) 1.84(2) 2.658(3) 145(2) . yes
N7 H71 O3 0.93(2) 1.78(2) 2.708(2) 173.9(13) 1_655 yes
N8 H81 N6 0.90(2) 1.88(2) 2.651(3) 143(2) . yes
C5 H5 O5 0.9500 2.3100 3.184(3) 153.00 2_666 yes
C22 H22 O4 0.9500 2.3900 3.181(4) 140.00 1_655 yes
C32 H32 O2 0.9500 2.4000 3.209(3) 143.00 2_656 yes

#===END



