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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1195–o1196.
Published online 2008 June 7. doi:  10.1107/S1600536808016115
PMCID: PMC2961859

S-Benzyl­thio­uronium 3-nitro­benzene­sulfonate

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-o1195-scheme1.jpg

Experimental

Crystal data

  • C8H11N2S+·C6H4NO5S
  • M r = 369.41
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1195-efi1.jpg
  • a = 6.0397 (1) Å
  • b = 7.7856 (1) Å
  • c = 17.4680 (2) Å
  • α = 81.366 (1)°
  • β = 89.322 (1)°
  • γ = 87.057 (1)°
  • V = 811.01 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.36 mm−1
  • T = 100.0 (1) K
  • 0.32 × 0.19 × 0.04 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.894, T max = 0.986
  • 19026 measured reflections
  • 8874 independent reflections
  • 7378 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.112
  • S = 1.03
  • 8874 reflections
  • 433 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.32 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 4108 Friedel pairs
  • Flack parameter: −0.03 (5)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016115/su2055sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016115/su2055Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. HKF and IAR also thank the Malaysian Government and Universiti Sains Malaysia for FRGS grant No. 203/PFIZIK/671064. SRJ thanks the Universiti Sains Malaysia for a post-doctoral research fellowship. This work was supported by the Department of Science and Technology (DST) and the Government of India (grant No. SR/S2/LOP-17/2006).

supplementary crystallographic information

Comment

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.

Experimental

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

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).

Figures

Fig. 1.
The molecular structure of compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.
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.

Crystal data

C8H11N2S+·C6H4NO5SZ = 2
Mr = 369.41F000 = 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 = 2.8–34.6º
c = 17.4680 (2) ŵ = 0.36 mm1
α = 81.366 (1)ºT = 100.0 (1) K
β = 89.322 (1)ºPlate, colourless
γ = 87.057 (1)º0.32 × 0.19 × 0.04 mm
V = 811.006 (19) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer8874 independent reflections
Radiation source: fine-focus sealed tube7378 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.043
T = 100.0(1) Kθmax = 30.1º
[var phi] and ω scansθmin = 1.2º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −7→8
Tmin = 0.894, Tmax = 0.986k = −10→10
19026 measured reflectionsl = −24→24

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044  w = 1/[σ2(Fo2) + (0.0534P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.112(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.38 e Å3
8874 reflectionsΔρmin = −0.32 e Å3
433 parametersExtinction correction: none
3 restraintsAbsolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.03 (5)
Secondary atom site location: difference Fourier map

Special details

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)

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)
H8A0.2493−0.05020.56770.022*
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)
H22A0.65950.3609−0.01180.029*
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)

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, °)

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—C2−90.1 (2)N2—C9—C10—C11−178.6 (3)
O5—S1—C1—C6−153.3 (2)C9—C10—C11—C12−0.2 (4)
O4—S1—C1—C6−32.0 (2)C8—C7—C12—C110.1 (4)
O3—S1—C1—C685.8 (2)S2—C7—C12—C11179.0 (2)
C6—C1—C2—C3−1.3 (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—C17−0.2 (5)
C3—C4—C5—C6−0.8 (4)C15—C16—C17—C180.3 (5)
C3—C4—C5—N1179.1 (2)C16—C17—C18—C13−0.2 (4)
O2—N1—C5—C65.8 (4)C16—C17—C18—C19−173.9 (3)
O1—N1—C5—C6−174.1 (2)C14—C13—C18—C170.1 (4)
O2—N1—C5—C4−174.1 (3)C14—C13—C18—C19173.6 (3)
O1—N1—C5—C46.0 (4)C17—C18—C19—S3−135.9 (2)
C4—C5—C6—C10.0 (4)C13—C18—C19—S350.5 (4)
N1—C5—C6—C1−179.8 (2)C20—S3—C19—C1867.8 (2)
C2—C1—C6—C51.0 (4)C19—S3—C20—N417.4 (3)
S1—C1—C6—C5−174.9 (2)C19—S3—C20—N3−163.9 (2)
O9—S2—C7—C1228.0 (3)C26—C21—C22—C230.2 (5)
O8—S2—C7—C12−92.5 (2)C21—C22—C23—C240.1 (5)
O10—S2—C7—C12148.9 (2)C22—C23—C24—C25−0.7 (5)
O9—S2—C7—C8−153.1 (2)C23—C24—C25—C261.0 (5)
O8—S2—C7—C886.4 (2)C22—C21—C26—C250.1 (4)
O10—S2—C7—C8−32.2 (3)C22—C21—C26—C27−178.5 (3)
C12—C7—C8—C9−0.2 (4)C24—C25—C26—C21−0.7 (4)
S2—C7—C8—C9−179.1 (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—S4−70.4 (3)
O6—N2—C9—C8177.2 (3)C28—S4—C27—C26−159.2 (2)
O7—N2—C9—C8−3.3 (4)C27—S4—C28—N5160.8 (2)
O6—N2—C9—C10−4.0 (4)C27—S4—C28—N6−18.8 (3)

Hydrogen-bond geometry (Å, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2055).

References

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