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The title compound, C8H15N3O3S, shows bond lengths and angles that are typical and are in accordance with expected values. The structure comprises a substituted thia­zolium ring that is connected to a nitrate ion via N—H...O hydrogen-bonding interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803003027/bt6236sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803003027/bt6236Isup2.hkl
Contains datablock I

CCDC reference: 206770

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.047
  • wR factor = 0.131
  • Data-to-parameter ratio = 18.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED; data reduction: CrysAlis RED (Oxford Diffraction, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

(I) top
Crystal data top
C8H15N3O3SZ = 2
Mr = 233.29F(000) = 248
Triclinic, P1Dx = 1.338 Mg m3
Dm = 1.319 Mg m3
Dm measured by flotation
a = 7.486 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.918 (2) ÅCell parameters from 4395 reflections
c = 9.240 (2) Åθ = 3.6–28.0°
α = 76.26 (3)°µ = 0.27 mm1
β = 87.15 (3)°T = 293 K
γ = 75.08 (3)°Irregular, colourless
V = 579.0 (2) Å30.2 × 0.15 × 0.1 mm
Data collection top
Xcalibur
diffractometer
2016 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.056
Graphite monochromatorθmax = 28.0°, θmin = 3.6°
Detector resolution: 1024 × 1024 with blocks 2 × 2 pixels mm-1h = 108
ω scansk = 1211
4395 measured reflectionsl = 1211
2712 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 0.98 w = 1/[σ2(Fo2) + (0.0762P)2]
where P = (Fo2 + 2Fc2)/3
2712 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.43 e Å3
Special details top

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
S10.21746 (7)0.40896 (6)0.22923 (6)0.02014 (17)
C50.0041 (3)0.5388 (2)0.2564 (2)0.0177 (4)
C40.1368 (3)0.4953 (2)0.2082 (2)0.0186 (4)
N30.0763 (2)0.3590 (2)0.15014 (19)0.0175 (4)
H3A0.162 (3)0.316 (3)0.116 (3)0.021*
C20.1065 (3)0.2972 (2)0.1535 (2)0.0173 (4)
N60.1918 (3)0.1695 (2)0.1041 (2)0.0206 (4)
H6A0.303 (4)0.133 (3)0.113 (3)0.025*
H6B0.123 (3)0.115 (3)0.071 (3)0.025*
C70.3394 (3)0.5703 (2)0.2126 (3)0.0217 (4)
H7A0.35880.66160.25480.033*
H7B0.39950.49440.27250.033*
H7C0.38990.60310.11320.033*
C80.0073 (3)0.6769 (2)0.3275 (3)0.0218 (4)
H8A0.07380.65920.42020.026*
H8B0.07930.77340.26230.026*
C90.1783 (3)0.7043 (2)0.3600 (2)0.0210 (4)
H9A0.25350.60760.42270.025*
H9B0.24320.72880.26740.025*
C100.1509 (3)0.8412 (3)0.4381 (2)0.0242 (5)
H10A0.07690.93750.37400.029*
H10B0.08240.81720.52880.029*
C110.3315 (4)0.8729 (3)0.4772 (3)0.0339 (6)
H11A0.30460.96000.52580.051*
H11B0.39890.89950.38780.051*
H11C0.40440.77910.54270.051*
N120.6761 (2)0.1062 (2)0.1077 (2)0.0201 (4)
O130.5809 (2)0.00502 (18)0.14171 (19)0.0284 (4)
O140.8421 (2)0.06598 (19)0.0696 (2)0.0321 (4)
O150.6067 (2)0.25091 (18)0.11105 (19)0.0277 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0147 (3)0.0195 (3)0.0288 (3)0.00064 (19)0.00108 (19)0.0143 (2)
C50.0149 (9)0.0163 (9)0.0215 (10)0.0001 (7)0.0018 (7)0.0079 (8)
C40.0182 (9)0.0156 (9)0.0214 (10)0.0003 (8)0.0020 (8)0.0083 (8)
N30.0171 (8)0.0154 (8)0.0224 (9)0.0027 (7)0.0005 (7)0.0107 (7)
C20.0173 (9)0.0143 (9)0.0199 (10)0.0014 (7)0.0007 (7)0.0060 (8)
N60.0153 (8)0.0190 (9)0.0308 (10)0.0020 (7)0.0009 (7)0.0146 (8)
C70.0156 (10)0.0188 (10)0.0299 (12)0.0004 (8)0.0003 (8)0.0092 (9)
C80.0190 (10)0.0186 (10)0.0302 (12)0.0010 (8)0.0006 (8)0.0143 (9)
C90.0209 (10)0.0199 (10)0.0247 (11)0.0039 (8)0.0009 (8)0.0113 (8)
C100.0306 (12)0.0204 (10)0.0235 (11)0.0060 (9)0.0029 (9)0.0098 (9)
C110.0415 (14)0.0310 (13)0.0358 (14)0.0151 (11)0.0049 (11)0.0128 (11)
N120.0180 (8)0.0179 (8)0.0263 (10)0.0008 (7)0.0010 (7)0.0127 (7)
O130.0196 (8)0.0222 (8)0.0473 (10)0.0080 (6)0.0045 (7)0.0136 (7)
O140.0166 (7)0.0332 (9)0.0554 (11)0.0067 (7)0.0100 (7)0.0288 (8)
O150.0241 (8)0.0177 (7)0.0429 (10)0.0023 (6)0.0045 (7)0.0174 (7)
Geometric parameters (Å, º) top
S1—C21.729 (2)C8—H8A0.9700
S1—C51.761 (2)C8—H8B0.9700
C5—C41.342 (3)C9—C101.526 (3)
C5—C81.509 (3)C9—H9A0.9700
C4—N31.404 (2)C9—H9B0.9700
C4—C71.494 (3)C10—C111.527 (3)
N3—C21.336 (3)C10—H10A0.9700
N3—H3A0.93 (2)C10—H10B0.9700
C2—N61.325 (2)C11—H11A0.9600
N6—H6A0.81 (3)C11—H11B0.9600
N6—H6B0.90 (3)C11—H11C0.9600
C7—H7A0.9600N12—O141.258 (2)
C7—H7B0.9600N12—O131.263 (2)
C7—H7C0.9600N12—O151.268 (2)
C8—C91.527 (3)
C2—S1—C590.9 (1)C5—C8—H8B108.5
C4—C5—C8127.3 (2)C9—C8—H8B108.5
C4—C5—S1110.94 (14)H8A—C8—H8B107.5
C8—C5—S1121.7 (1)C10—C9—C8110.87 (17)
C5—C4—N3112.26 (17)C10—C9—H9A109.5
C5—C4—C7128.51 (18)C8—C9—H9A109.5
N3—C4—C7119.2 (2)C10—C9—H9B109.5
C2—N3—C4115.45 (17)C8—C9—H9B109.5
C2—N3—H3A124.5 (15)H9A—C9—H9B108.1
C4—N3—H3A120.0 (15)C11—C10—C9113.70 (19)
N6—C2—N3125.07 (18)C11—C10—H10A108.8
N6—C2—S1124.49 (16)C9—C10—H10A108.8
N3—C2—S1110.43 (14)C11—C10—H10B108.8
C2—N6—H6A121.5 (18)C9—C10—H10B108.8
C2—N6—H6B118.6 (15)H10A—C10—H10B107.7
H6A—N6—H6B119 (2)C10—C11—H11A109.5
C4—C7—H7A109.5C10—C11—H11B109.5
C4—C7—H7B109.5H11A—C11—H11B109.5
H7A—C7—H7B109.5C10—C11—H11C109.5
C4—C7—H7C109.5H11A—C11—H11C109.5
H7A—C7—H7C109.5H11B—C11—H11C109.5
H7B—C7—H7C109.5O14—N12—O13120.81 (17)
C5—C8—C9115.28 (17)O14—N12—O15118.39 (18)
C5—C8—H8A108.5O13—N12—O15120.80 (17)
C9—C8—H8A108.5
C2—S1—C5—C40.44 (17)C4—N3—C2—N6179.80 (19)
C2—S1—C5—C8178.71 (18)C4—N3—C2—S10.7 (2)
C8—C5—C4—N3178.94 (19)C5—S1—C2—N6179.74 (19)
S1—C5—C4—N30.1 (2)C5—S1—C2—N30.63 (16)
C8—C5—C4—C70.2 (4)C4—C5—C8—C9175.5 (2)
S1—C5—C4—C7178.85 (18)S1—C5—C8—C95.5 (3)
C5—C4—N3—C20.4 (3)C5—C8—C9—C10177.37 (18)
C7—C4—N3—C2178.48 (19)C8—C9—C10—C11178.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H6A···O130.81 (3)2.10 (3)2.901 (3)171 (2)
N3—H3A···O14i0.92 (3)2.36 (3)3.090 (3)135 (2)
N3—H3A···O15i0.92 (3)1.97 (3)2.849 (3)157 (2)
N6—H6B···O14i0.90 (3)2.25 (3)3.045 (3)146 (2)
N6—H6B···O14ii0.90 (3)2.25 (3)2.994 (3)138 (2)
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.
 

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