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In the title compound, C8H11N2S+·C6H4NO5S, the asymmetric unit is composed of two crystallographically independent S-benzyl­thio­uronium cations and two independent nitro­benzene­sulfonate anions. An intra­molecular hydrogen bond generates an S(5)S(5) ring motif. The crystal packing is stabilized by intra­molecular C—H...O and inter­molecular C—H...O, N—H...O and N—H...S hydrogen bonds which, along with short S...O [3.034 (2) Å] and N...O [2.796 (3) Å] contacts, form a two-dimensional network parallel to the ab plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808016115/su2055sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536808016115/su2055Isup2.hkl
Contains datablock I

CCDC reference: 696481

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.044
  • wR factor = 0.113
  • Data-to-parameter ratio = 20.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O10 .. N1 .. 2.85 Ang.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_4_C Check Cell Rounding: # of Values Ending with 0 = 6 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Labels .......... 8
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 30.08 From the CIF: _reflns_number_total 8874 Count of symmetry unique reflns 4772 Completeness (_total/calc) 185.96% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 4102 Fraction of Friedel pairs measured 0.860 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: The authors FHK, SRJ and IAR were involved in the data collection, structure solution and preparation of publication material. The authors PSP, SMD and EDDS were involved in the synthesis of the compound in different phases.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Comment top

In continuation of our research on nonlinear optical (NLO) materials (Chantrapromma et al., 2005, 2006; Fun et al., 2006; Patil, Dharmaprakash et al. (2007); Patil, Fun et al. (2007), the crystal structure determination of the title compound, (I), was undertaken in order to obtain detailed information on its three-dimensional structure and crystal packing. Since the title compound crystallizes in a non-centrosymmetric space group, it should exhibit second-order nonlinear optical properties.

In the asymmetric unit of (I) there are two crystallographically independent s-benzylthiuronium cations and two independent m-nitrobenzene sulfonate anions (Fig. 1). Bond lengths and angles are found to have normal values (Allen et al., 1987). The dihedral angle formed by the mean plane of ring (C13–C18) with the mean planes through rings (C21–C26), (C1–C6) and (C7–C12) are 57.6 (2)°, 49.9 (2)° and 46.98 (1)°, respectively. The dihedral angle formed by the mean planes of rings (C1–C6) and (C7–C12) are 3.07 (1)°, indicating that they are almost coplanar.

An intramolecular hydrogen bond generates a S(5)S(5) ring motif (Bernstein et al., 1995). The crystal packing (Fig. 2) is stabilized by intramolecular C—H···O, intermolecular C—H···O, N—H···O and N—H···S hydrogen bonds which together with short S···O and N···O contacts, in the range 2.796 (3)–3.282 (3) Å [symmetry code: x, 1+y, z; 1+x, 1+y, z], form a two-dimensional network parrallel to the ab plane.

Related literature top

For related literature on nonlinear optical materials, see: Chantrapromma et al. (2005, 2006); Fun et al. (2006); Patil, Dharmaprakash et al. (2007); Patil, Fun et al. (2007). For bond-length data, see: Allen et al. (1987). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental top

Compound (I) was synthesized by mixing solutions of the sodium salt of m-nitrobenzene sulfonic acid (0.5 g) in 5 ml of distilled water with 5 drops of 0.1 N HCl and S-benzylthiuronium chloride (1 g) in 5 ml of distilled water. The mixing immediately yielded a precipitate when the reaction container was placed in ice cold water. The resulting precipitate was filtered and dried. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of an ethanol solution at room temperature.

Refinement top

H atoms were positioned geometrically [C—H = 0.93 Å; N—H = 0.86 Å and CH2 = 0.97 Å] and refined using a riding model with Uiso(H) = 1.2Ueq(C, N).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.
[Figure 2] Fig. 2. The crystal packing of compound (I) viewed down the c axis, showing the two-dimensional network. Short intra and intermolecular contacts and hydrogen bonds are shown as dashed lines.
(5-Methylpyrazine-2-carboxylato)diphenyltin(IV) top
Crystal data top
C8H11N2S+·C6H4NO5SZ = 2
Mr = 369.41F(000) = 384
Triclinic, P1Dx = 1.513 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.0397 (1) ÅCell parameters from 4354 reflections
b = 7.7856 (1) Åθ = 2.8–34.6°
c = 17.4680 (2) ŵ = 0.36 mm1
α = 81.366 (1)°T = 100 K
β = 89.322 (1)°Plate, colourless
γ = 87.057 (1)°0.32 × 0.19 × 0.04 mm
V = 811.01 (2) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
8874 independent reflections
Radiation source: fine-focus sealed tube7378 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ϕ and ω scansθmax = 30.1°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 78
Tmin = 0.894, Tmax = 0.986k = 1010
19026 measured reflectionsl = 2424
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0534P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
8874 reflectionsΔρmax = 0.38 e Å3
433 parametersΔρmin = 0.32 e Å3
3 restraintsAbsolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (5)
Crystal data top
C8H11N2S+·C6H4NO5Sγ = 87.057 (1)°
Mr = 369.41V = 811.01 (2) Å3
Triclinic, P1Z = 2
a = 6.0397 (1) ÅMo Kα radiation
b = 7.7856 (1) ŵ = 0.36 mm1
c = 17.4680 (2) ÅT = 100 K
α = 81.366 (1)°0.32 × 0.19 × 0.04 mm
β = 89.322 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
8874 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
7378 reflections with I > 2σ(I)
Tmin = 0.894, Tmax = 0.986Rint = 0.043
19026 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.112Δρmax = 0.38 e Å3
S = 1.03Δρmin = 0.32 e Å3
8874 reflectionsAbsolute structure: Flack (1983), with how many Friedel pairs?
433 parametersAbsolute structure parameter: 0.03 (5)
3 restraints
Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.37546 (10)0.53723 (8)0.82205 (4)0.01444 (14)
O10.4811 (4)0.4607 (3)0.47221 (12)0.0252 (5)
O20.1931 (4)0.4114 (3)0.54531 (12)0.0241 (5)
O30.4577 (3)0.3635 (3)0.85663 (11)0.0180 (4)
O40.1377 (3)0.5430 (3)0.80849 (11)0.0184 (4)
O50.4448 (3)0.6737 (3)0.86311 (12)0.0206 (4)
N10.3820 (4)0.4617 (3)0.53419 (14)0.0193 (5)
C10.4988 (4)0.5723 (3)0.72854 (15)0.0147 (5)
C20.7020 (4)0.6478 (4)0.71677 (16)0.0167 (5)
H2A0.77100.69030.75690.020*
C30.8017 (5)0.6590 (4)0.64337 (18)0.0207 (6)
H3A0.93840.70850.63510.025*
C40.7004 (5)0.5977 (4)0.58323 (17)0.0184 (6)
H4A0.76730.60440.53470.022*
C50.4953 (5)0.5255 (4)0.59719 (16)0.0163 (5)
C60.3912 (5)0.5112 (3)0.66886 (15)0.0154 (5)
H6A0.25390.46230.67670.018*
S20.31950 (11)0.08507 (8)0.41082 (4)0.01834 (15)
O60.5275 (5)0.1046 (3)0.73759 (13)0.0379 (6)
O70.2256 (5)0.0097 (4)0.69863 (14)0.0493 (8)
O80.1789 (4)0.0611 (3)0.37490 (12)0.0231 (5)
O90.4738 (4)0.1484 (3)0.35681 (13)0.0301 (5)
O100.1907 (4)0.2203 (3)0.45482 (13)0.0282 (5)
N20.4156 (5)0.0558 (4)0.68796 (15)0.0285 (6)
C70.4798 (5)0.0078 (4)0.48202 (16)0.0168 (5)
C80.3892 (5)0.0087 (4)0.55576 (17)0.0185 (6)
H8A0.24930.05020.56770.022*
C90.5124 (5)0.0534 (4)0.61044 (17)0.0215 (6)
C100.7218 (5)0.1167 (4)0.59464 (18)0.0227 (6)
H10A0.80170.15780.63270.027*
C110.8082 (5)0.1169 (4)0.52112 (19)0.0239 (6)
H11A0.94790.15900.50940.029*
C120.6880 (5)0.0546 (4)0.46421 (17)0.0195 (6)
H12A0.74710.05490.41480.023*
S30.77990 (11)0.92863 (9)0.89784 (5)0.02185 (17)
N30.9177 (4)1.2377 (3)0.85658 (14)0.0211 (5)
H1N31.01121.31730.84480.025*
H2N30.77781.26430.85440.025*
N41.1997 (4)1.0283 (3)0.88215 (14)0.0199 (5)
H1N41.29731.10480.87080.024*
H2N41.24080.92090.89630.024*
C130.8638 (5)0.8126 (4)1.08658 (18)0.0229 (6)
H13A0.72310.86111.07300.027*
C140.9388 (6)0.8053 (4)1.16156 (19)0.0292 (7)
H14A0.84790.84901.19820.035*
C151.1470 (6)0.7337 (4)1.18259 (18)0.0294 (7)
H15A1.19610.72901.23320.035*
C161.2827 (6)0.6688 (4)1.12789 (19)0.0274 (7)
H16A1.42340.62081.14170.033*
C171.2086 (5)0.6754 (4)1.05282 (17)0.0217 (6)
H17A1.30000.63121.01640.026*
C180.9993 (5)0.7473 (4)1.03121 (17)0.0178 (6)
C190.9156 (5)0.7358 (4)0.95108 (18)0.0216 (6)
H19A0.81270.64320.95560.026*
H19B1.04060.70150.92040.026*
C200.9890 (5)1.0752 (4)0.87791 (15)0.0165 (5)
S40.70823 (11)0.42238 (9)0.29521 (4)0.02029 (15)
N50.8675 (4)0.6477 (3)0.37270 (14)0.0205 (5)
H1N50.96470.69320.39800.025*
H2N50.73790.69800.36500.025*
N61.1136 (4)0.4218 (3)0.35682 (14)0.0209 (5)
H1N61.21320.46500.38190.025*
H2N61.14250.32620.33880.025*
C210.7614 (5)0.3251 (4)0.09917 (17)0.0211 (6)
H21A0.89050.38520.09000.025*
C220.6228 (5)0.3107 (4)0.03818 (17)0.0241 (6)
H22A0.65950.36090.01180.029*
C230.4305 (5)0.2224 (4)0.05098 (18)0.0258 (7)
H23A0.33780.21280.00990.031*
C240.3766 (5)0.1484 (4)0.12517 (19)0.0266 (7)
H24A0.24630.08970.13410.032*
C250.5157 (5)0.1608 (4)0.18650 (17)0.0228 (6)
H25A0.47940.10910.23620.027*
C260.7088 (5)0.2503 (4)0.17390 (16)0.0180 (6)
C270.8588 (5)0.2713 (4)0.23962 (17)0.0242 (6)
H27A0.99760.31820.22000.029*
H27B0.89050.16010.27180.029*
C280.9169 (5)0.5019 (4)0.34598 (16)0.0175 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0132 (3)0.0156 (3)0.0147 (3)0.0010 (2)0.0006 (2)0.0028 (2)
O10.0274 (12)0.0322 (12)0.0163 (10)0.0034 (9)0.0009 (9)0.0061 (9)
O20.0218 (11)0.0285 (12)0.0236 (11)0.0070 (9)0.0016 (9)0.0066 (9)
O30.0197 (10)0.0164 (10)0.0169 (9)0.0018 (8)0.0002 (8)0.0000 (8)
O40.0138 (10)0.0201 (10)0.0209 (10)0.0010 (8)0.0001 (8)0.0019 (8)
O50.0202 (10)0.0223 (10)0.0222 (10)0.0061 (8)0.0008 (8)0.0111 (8)
N10.0229 (14)0.0157 (12)0.0188 (12)0.0024 (10)0.0025 (10)0.0019 (9)
C10.0144 (13)0.0126 (13)0.0167 (13)0.0009 (10)0.0022 (10)0.0018 (10)
C20.0130 (13)0.0167 (13)0.0199 (13)0.0007 (10)0.0032 (10)0.0012 (11)
C30.0128 (13)0.0199 (14)0.0273 (15)0.0018 (10)0.0006 (11)0.0034 (12)
C40.0167 (14)0.0195 (14)0.0182 (13)0.0018 (11)0.0020 (11)0.0008 (11)
C50.0176 (13)0.0149 (13)0.0166 (12)0.0015 (10)0.0048 (10)0.0031 (10)
C60.0141 (13)0.0144 (13)0.0170 (13)0.0010 (10)0.0017 (10)0.0002 (10)
S20.0198 (4)0.0174 (3)0.0176 (3)0.0013 (3)0.0044 (3)0.0023 (3)
O60.0591 (18)0.0348 (14)0.0216 (12)0.0018 (12)0.0106 (11)0.0094 (10)
O70.0337 (15)0.092 (2)0.0243 (13)0.0050 (15)0.0061 (11)0.0138 (14)
O80.0235 (11)0.0209 (11)0.0232 (10)0.0045 (8)0.0055 (9)0.0004 (9)
O90.0310 (13)0.0378 (13)0.0224 (11)0.0120 (10)0.0038 (9)0.0118 (10)
O100.0330 (13)0.0221 (11)0.0284 (11)0.0104 (9)0.0110 (10)0.0035 (9)
N20.0390 (18)0.0263 (14)0.0199 (13)0.0067 (12)0.0021 (12)0.0052 (11)
C70.0169 (14)0.0150 (13)0.0175 (13)0.0034 (10)0.0031 (10)0.0003 (10)
C80.0172 (14)0.0171 (13)0.0205 (13)0.0024 (11)0.0019 (11)0.0019 (11)
C90.0232 (16)0.0201 (15)0.0206 (14)0.0059 (11)0.0056 (11)0.0036 (11)
C100.0206 (15)0.0202 (15)0.0276 (15)0.0037 (11)0.0091 (12)0.0055 (12)
C110.0149 (14)0.0199 (15)0.0363 (17)0.0018 (11)0.0032 (12)0.0021 (13)
C120.0178 (14)0.0164 (14)0.0235 (14)0.0011 (11)0.0009 (11)0.0013 (11)
S30.0150 (4)0.0199 (4)0.0292 (4)0.0045 (3)0.0034 (3)0.0025 (3)
N30.0147 (12)0.0189 (12)0.0294 (13)0.0045 (9)0.0001 (10)0.0012 (10)
N40.0142 (12)0.0211 (13)0.0241 (12)0.0025 (9)0.0002 (10)0.0016 (10)
C130.0206 (15)0.0208 (15)0.0268 (15)0.0007 (11)0.0053 (12)0.0024 (12)
C140.0363 (19)0.0219 (16)0.0287 (16)0.0027 (13)0.0097 (14)0.0010 (13)
C150.038 (2)0.0278 (18)0.0200 (15)0.0090 (14)0.0013 (13)0.0053 (13)
C160.0228 (16)0.0265 (17)0.0298 (17)0.0019 (12)0.0054 (13)0.0067 (13)
C170.0192 (15)0.0220 (15)0.0224 (14)0.0022 (11)0.0039 (12)0.0002 (12)
C180.0176 (14)0.0130 (13)0.0224 (14)0.0041 (10)0.0024 (11)0.0004 (11)
C190.0195 (15)0.0150 (14)0.0298 (16)0.0016 (11)0.0014 (12)0.0017 (12)
C200.0156 (13)0.0207 (14)0.0136 (12)0.0031 (10)0.0007 (10)0.0027 (10)
S40.0170 (4)0.0252 (4)0.0202 (3)0.0003 (3)0.0022 (3)0.0082 (3)
N50.0177 (12)0.0222 (13)0.0228 (12)0.0013 (9)0.0009 (10)0.0067 (10)
N60.0187 (13)0.0233 (13)0.0212 (12)0.0006 (10)0.0056 (10)0.0050 (10)
C210.0222 (15)0.0188 (14)0.0224 (14)0.0025 (11)0.0019 (12)0.0027 (12)
C220.0329 (18)0.0236 (16)0.0157 (13)0.0003 (13)0.0014 (12)0.0027 (12)
C230.0283 (17)0.0249 (16)0.0265 (16)0.0023 (13)0.0125 (13)0.0116 (13)
C240.0242 (16)0.0241 (16)0.0335 (17)0.0064 (12)0.0009 (13)0.0087 (13)
C250.0269 (16)0.0221 (15)0.0185 (14)0.0005 (12)0.0036 (12)0.0001 (12)
C260.0215 (15)0.0182 (14)0.0149 (12)0.0013 (11)0.0023 (11)0.0047 (11)
C270.0256 (16)0.0286 (16)0.0197 (14)0.0069 (12)0.0035 (12)0.0103 (12)
C280.0163 (14)0.0215 (15)0.0144 (12)0.0026 (11)0.0008 (11)0.0011 (11)
Geometric parameters (Å, º) top
S1—O51.449 (2)N4—C201.306 (4)
S1—O41.456 (2)N4—H1N40.8600
S1—O31.461 (2)N4—H2N40.8600
S1—C11.776 (3)C13—C141.383 (5)
O1—N11.232 (3)C13—C181.396 (4)
O2—N11.229 (3)C13—H13A0.9300
N1—C51.464 (4)C14—C151.380 (5)
C1—C21.388 (4)C14—H14A0.9300
C1—C61.390 (4)C15—C161.387 (5)
C2—C31.403 (4)C15—H15A0.9300
C2—H2A0.9300C16—C171.383 (4)
C3—C41.379 (4)C16—H16A0.9300
C3—H3A0.9300C17—C181.389 (4)
C4—C51.390 (4)C17—H17A0.9300
C4—H4A0.9300C18—C191.510 (4)
C5—C61.386 (4)C19—H19A0.9700
C6—H6A0.9300C19—H19B0.9700
S2—O91.440 (2)S4—C281.740 (3)
S2—O81.452 (2)S4—C271.835 (3)
S2—O101.460 (2)N5—C281.310 (4)
S2—C71.778 (3)N5—H1N50.8600
O6—N21.222 (4)N5—H2N50.8600
O7—N21.224 (4)N6—C281.315 (4)
N2—C91.471 (4)N6—H1N60.8600
C7—C121.386 (4)N6—H2N60.8600
C7—C81.393 (4)C21—C221.384 (4)
C8—C91.376 (4)C21—C261.387 (4)
C8—H8A0.9300C21—H21A0.9300
C9—C101.390 (4)C22—C231.379 (5)
C10—C111.380 (5)C22—H22A0.9300
C10—H10A0.9300C23—C241.379 (4)
C11—C121.396 (4)C23—H23A0.9300
C11—H11A0.9300C24—C251.387 (4)
C12—H12A0.9300C24—H24A0.9300
S3—C201.742 (3)C25—C261.388 (4)
S3—C191.806 (3)C25—H25A0.9300
N3—C201.316 (4)C26—C271.504 (4)
N3—H1N30.8600C27—H27A0.9700
N3—H2N30.8600C27—H27B0.9700
O5—S1—O4113.68 (12)C14—C13—C18120.0 (3)
O5—S1—O3113.38 (12)C14—C13—H13A120.0
O4—S1—O3111.39 (12)C18—C13—H13A120.0
O5—S1—C1107.07 (12)C15—C14—C13120.7 (3)
O4—S1—C1105.35 (12)C15—C14—H14A119.6
O3—S1—C1105.17 (12)C13—C14—H14A119.6
O2—N1—O1122.9 (2)C14—C15—C16119.6 (3)
O2—N1—C5118.8 (2)C14—C15—H15A120.2
O1—N1—C5118.3 (2)C16—C15—H15A120.2
C2—C1—C6121.3 (3)C17—C16—C15120.0 (3)
C2—C1—S1121.1 (2)C17—C16—H16A120.0
C6—C1—S1117.5 (2)C15—C16—H16A120.0
C1—C2—C3118.9 (3)C16—C17—C18120.7 (3)
C1—C2—H2A120.5C16—C17—H17A119.6
C3—C2—H2A120.5C18—C17—H17A119.6
C4—C3—C2121.1 (3)C17—C18—C13119.0 (3)
C4—C3—H3A119.4C17—C18—C19119.0 (3)
C2—C3—H3A119.4C13—C18—C19121.7 (3)
C3—C4—C5118.1 (3)C18—C19—S3117.6 (2)
C3—C4—H4A121.0C18—C19—H19A107.9
C5—C4—H4A121.0S3—C19—H19A107.9
C6—C5—C4122.7 (3)C18—C19—H19B107.9
C6—C5—N1117.9 (2)S3—C19—H19B107.9
C4—C5—N1119.4 (2)H19A—C19—H19B107.2
C5—C6—C1117.8 (3)N4—C20—N3122.3 (3)
C5—C6—H6A121.1N4—C20—S3123.1 (2)
C1—C6—H6A121.1N3—C20—S3114.6 (2)
O9—S2—O8112.40 (13)C28—S4—C27103.46 (14)
O9—S2—O10113.93 (15)C28—N5—H1N5120.0
O8—S2—O10111.89 (14)C28—N5—H2N5120.0
O9—S2—C7106.75 (14)H1N5—N5—H2N5120.0
O8—S2—C7106.93 (13)C28—N6—H1N6120.0
O10—S2—C7104.21 (13)C28—N6—H2N6120.0
O6—N2—O7123.8 (3)H1N6—N6—H2N6120.0
O6—N2—C9118.6 (3)C22—C21—C26120.4 (3)
O7—N2—C9117.6 (3)C22—C21—H21A119.8
C12—C7—C8120.9 (3)C26—C21—H21A119.8
C12—C7—S2120.8 (2)C23—C22—C21120.4 (3)
C8—C7—S2118.3 (2)C23—C22—H22A119.8
C9—C8—C7118.1 (3)C21—C22—H22A119.8
C9—C8—H8A120.9C22—C23—C24119.6 (3)
C7—C8—H8A120.9C22—C23—H23A120.2
C8—C9—C10122.5 (3)C24—C23—H23A120.2
C8—C9—N2118.3 (3)C23—C24—C25120.4 (3)
C10—C9—N2119.2 (3)C23—C24—H24A119.8
C11—C10—C9118.4 (3)C25—C24—H24A119.8
C11—C10—H10A120.8C24—C25—C26120.2 (3)
C9—C10—H10A120.8C24—C25—H25A119.9
C10—C11—C12120.6 (3)C26—C25—H25A119.9
C10—C11—H11A119.7C21—C26—C25119.0 (3)
C12—C11—H11A119.7C21—C26—C27119.5 (3)
C7—C12—C11119.4 (3)C25—C26—C27121.4 (3)
C7—C12—H12A120.3C26—C27—S4105.9 (2)
C11—C12—H12A120.3C26—C27—H27A110.6
C20—S3—C19104.77 (14)S4—C27—H27A110.6
C20—N3—H1N3120.0C26—C27—H27B110.6
C20—N3—H2N3120.0S4—C27—H27B110.6
H1N3—N3—H2N3120.0H27A—C27—H27B108.7
C20—N4—H1N4120.0N5—C28—N6121.5 (3)
C20—N4—H2N4120.0N5—C28—S4116.1 (2)
H1N4—N4—H2N4120.0N6—C28—S4122.4 (2)
O5—S1—C1—C230.8 (3)O7—N2—C9—C10175.5 (3)
O4—S1—C1—C2152.1 (2)C8—C9—C10—C110.1 (4)
O3—S1—C1—C290.1 (2)N2—C9—C10—C11178.6 (3)
O5—S1—C1—C6153.3 (2)C9—C10—C11—C120.2 (4)
O4—S1—C1—C632.0 (2)C8—C7—C12—C110.1 (4)
O3—S1—C1—C685.8 (2)S2—C7—C12—C11179.0 (2)
C6—C1—C2—C31.3 (4)C10—C11—C12—C70.1 (4)
S1—C1—C2—C3174.5 (2)C18—C13—C14—C150.0 (5)
C1—C2—C3—C40.5 (4)C13—C14—C15—C160.1 (5)
C2—C3—C4—C50.5 (4)C14—C15—C16—C170.2 (5)
C3—C4—C5—C60.8 (4)C15—C16—C17—C180.3 (5)
C3—C4—C5—N1179.1 (2)C16—C17—C18—C130.2 (4)
O2—N1—C5—C65.8 (4)C16—C17—C18—C19173.9 (3)
O1—N1—C5—C6174.1 (2)C14—C13—C18—C170.1 (4)
O2—N1—C5—C4174.1 (3)C14—C13—C18—C19173.6 (3)
O1—N1—C5—C46.0 (4)C17—C18—C19—S3135.9 (2)
C4—C5—C6—C10.0 (4)C13—C18—C19—S350.5 (4)
N1—C5—C6—C1179.8 (2)C20—S3—C19—C1867.8 (2)
C2—C1—C6—C51.0 (4)C19—S3—C20—N417.4 (3)
S1—C1—C6—C5174.9 (2)C19—S3—C20—N3163.9 (2)
O9—S2—C7—C1228.0 (3)C26—C21—C22—C230.2 (5)
O8—S2—C7—C1292.5 (2)C21—C22—C23—C240.1 (5)
O10—S2—C7—C12148.9 (2)C22—C23—C24—C250.7 (5)
O9—S2—C7—C8153.1 (2)C23—C24—C25—C261.0 (5)
O8—S2—C7—C886.4 (2)C22—C21—C26—C250.1 (4)
O10—S2—C7—C832.2 (3)C22—C21—C26—C27178.5 (3)
C12—C7—C8—C90.2 (4)C24—C25—C26—C210.7 (4)
S2—C7—C8—C9179.1 (2)C24—C25—C26—C27177.9 (3)
C7—C8—C9—C100.1 (4)C21—C26—C27—S4108.2 (3)
C7—C8—C9—N2178.8 (3)C25—C26—C27—S470.4 (3)
O6—N2—C9—C8177.2 (3)C28—S4—C27—C26159.2 (2)
O7—N2—C9—C83.3 (4)C27—S4—C28—N5160.8 (2)
O6—N2—C9—C104.0 (4)C27—S4—C28—N618.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1N3···O4i0.861.972.796 (3)162
N3—H1N3···S1i0.862.843.694 (3)170
N3—H2N3···O3ii0.862.052.898 (3)171
N4—H1N4···O3i0.862.263.080 (3)160
N4—H2N4···O5iii0.862.373.126 (3)146
N5—H1N5···O10i0.861.912.764 (3)176
N5—H1N5···S2i0.862.853.642 (3)154
N5—H2N5···O9ii0.861.942.783 (3)168
N6—H1N6···O1iii0.862.273.072 (3)156
N6—H2N6···O8iii0.862.072.787 (3)141
C6—H6A···O40.932.562.900 (3)102
C8—H8A···O100.932.572.896 (4)101
C19—H19B···O4iii0.972.513.331 (4)142
C27—H27B···O8iii0.972.533.259 (4)132
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC8H11N2S+·C6H4NO5S
Mr369.41
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)6.0397 (1), 7.7856 (1), 17.4680 (2)
α, β, γ (°)81.366 (1), 89.322 (1), 87.057 (1)
V3)811.01 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.36
Crystal size (mm)0.32 × 0.19 × 0.04
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.894, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
19026, 8874, 7378
Rint0.043
(sin θ/λ)max1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.112, 1.03
No. of reflections8874
No. of parameters433
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.32
Absolute structureFlack (1983), with how many Friedel pairs?
Absolute structure parameter0.03 (5)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1N3···O4i0.861.972.796 (3)161.8
N3—H1N3···S1i0.862.843.694 (3)169.6
N3—H2N3···O3ii0.862.052.898 (3)170.5
N4—H1N4···O3i0.862.263.080 (3)159.9
N4—H2N4···O5iii0.862.373.126 (3)146.3
N5—H1N5···O10i0.861.912.764 (3)176.3
N5—H1N5···S2i0.862.853.642 (3)153.7
N5—H2N5···O9ii0.861.942.783 (3)167.6
N6—H1N6···O1iii0.862.273.072 (3)155.8
N6—H2N6···O8iii0.862.072.787 (3)140.8
C6—H6A···O40.932.562.900 (3)102
C8—H8A···O100.932.572.896 (4)101
C19—H19B···O4iii0.972.513.331 (4)142
C27—H27B···O8iii0.972.533.259 (4)132
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z; (iii) x+1, y, z.
 

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