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In the title mol­ecule, C7H7N5O3S, all of the atoms in the fused ring system, except for the O atom, are essentially in the same plane. The O atom forms the flap of the envelope conformation of the sultone ring. In the absence of any hydrogen-bond or π–π stacking inter­actions, the structure appears to be stabilized only by normal van der Waals inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805021781/lh6452sup1.cif
Contains datablocks global, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805021781/lh64523sup2.hkl
Contains datablock 3

CCDC reference: 282530

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.030
  • wR factor = 0.087
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for N3 - N4 .. 6.23 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: APEXII (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

5-Azido-3,3-dimethyl-2-oxo-1-thia-4,6-diazaindan 1,1-dioxide top
Crystal data top
C7H7N5O3SF(000) = 992
Mr = 241.24Dx = 1.582 Mg m3
Monoclinic, C2/cMelting point: 161 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 14.4162 (16) ÅCell parameters from 3013 reflections
b = 8.5691 (10) Åθ = 2.5–27.8°
c = 17.0016 (19) ŵ = 0.32 mm1
β = 105.365 (1)°T = 293 K
V = 2025.2 (4) Å3Block, colourless
Z = 80.22 × 0.16 × 0.10 mm
Data collection top
Bruker APEX-II CCD
diffractometer
1784 independent reflections
Radiation source: fine-focus sealed tube1587 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
φ and ω scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1717
Tmin = 0.933, Tmax = 0.969k = 710
5286 measured reflectionsl = 1720
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)] = 0.030H-atom parameters constrained
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0468P)2 + 1.3512P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1784 reflectionsΔρmax = 0.29 e Å3
148 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0045 (5)
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
S10.17681 (3)0.18013 (5)0.19388 (2)0.03951 (18)
O10.17061 (10)0.05324 (17)0.13946 (8)0.0585 (4)
O20.15377 (10)0.33066 (16)0.15990 (8)0.0576 (4)
O30.11307 (9)0.13929 (18)0.25320 (7)0.0536 (4)
N10.44807 (10)0.19697 (16)0.33826 (8)0.0389 (3)
N20.33040 (10)0.18719 (16)0.41569 (8)0.0385 (3)
N30.49018 (11)0.1923 (2)0.48175 (9)0.0519 (4)
N40.57431 (11)0.18141 (18)0.47431 (9)0.0467 (4)
N50.65144 (12)0.1704 (2)0.47631 (11)0.0633 (5)
C10.13207 (14)0.0420 (2)0.38901 (13)0.0555 (5)
H1A0.06340.03260.37720.083*
H1B0.15830.06110.44620.083*
H1C0.15850.05290.37420.083*
C20.12069 (13)0.3315 (2)0.36141 (13)0.0517 (5)
H2A0.13510.41050.32640.078*
H2B0.15130.35720.41720.078*
H2C0.05240.32590.35370.078*
C30.15726 (12)0.1760 (2)0.34090 (10)0.0394 (4)
C40.26360 (11)0.18306 (18)0.34584 (10)0.0343 (4)
C50.42007 (11)0.19209 (19)0.40737 (10)0.0373 (4)
C60.37854 (12)0.19444 (19)0.26910 (10)0.0384 (4)
H60.39390.19860.21940.046*
C70.28357 (11)0.18562 (18)0.27084 (9)0.0351 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0348 (3)0.0491 (3)0.0326 (3)0.00002 (17)0.00519 (17)0.00238 (17)
O10.0574 (8)0.0642 (9)0.0500 (7)0.0023 (7)0.0072 (6)0.0183 (7)
O20.0561 (8)0.0560 (9)0.0517 (8)0.0054 (6)0.0016 (6)0.0094 (6)
O30.0336 (6)0.0850 (10)0.0410 (7)0.0097 (6)0.0078 (5)0.0049 (7)
N10.0323 (7)0.0502 (8)0.0352 (7)0.0008 (6)0.0108 (6)0.0015 (6)
N20.0341 (7)0.0498 (8)0.0327 (7)0.0000 (6)0.0109 (6)0.0019 (6)
N30.0337 (8)0.0850 (12)0.0357 (8)0.0001 (7)0.0067 (6)0.0012 (7)
N40.0387 (9)0.0620 (10)0.0360 (8)0.0034 (7)0.0036 (6)0.0017 (7)
N50.0356 (9)0.0890 (14)0.0616 (11)0.0023 (8)0.0061 (8)0.0008 (9)
C10.0488 (10)0.0583 (12)0.0636 (12)0.0085 (9)0.0222 (9)0.0086 (10)
C20.0430 (10)0.0572 (12)0.0599 (12)0.0065 (8)0.0221 (9)0.0017 (9)
C30.0319 (8)0.0520 (10)0.0350 (8)0.0029 (7)0.0100 (7)0.0004 (7)
C40.0332 (8)0.0368 (8)0.0344 (8)0.0007 (6)0.0115 (6)0.0011 (6)
C50.0341 (8)0.0445 (9)0.0330 (8)0.0004 (7)0.0082 (7)0.0018 (7)
C60.0368 (8)0.0478 (10)0.0332 (8)0.0002 (7)0.0136 (7)0.0014 (7)
C70.0340 (8)0.0405 (9)0.0305 (8)0.0001 (6)0.0080 (6)0.0008 (6)
Geometric parameters (Å, º) top
S1—O11.4151 (14)C1—C31.509 (2)
S1—O21.4165 (14)C1—H1A0.9600
S1—O31.5732 (13)C1—H1B0.9600
S1—C71.7366 (16)C1—H1C0.9600
O3—C31.492 (2)C2—C31.508 (2)
N1—C61.328 (2)C2—H2A0.9600
N1—C51.340 (2)C2—H2B0.9600
N2—C41.316 (2)C2—H2C0.9600
N2—C51.338 (2)C3—C41.514 (2)
N3—N41.256 (2)C4—C71.380 (2)
N3—C51.394 (2)C6—C71.379 (2)
N4—N51.107 (2)C6—H60.9300
O1—S1—O2117.75 (9)H2A—C2—H2C109.5
O1—S1—O3107.57 (8)H2B—C2—H2C109.5
O2—S1—O3110.51 (9)O3—C3—C2109.56 (14)
O1—S1—C7113.78 (8)O3—C3—C1106.31 (14)
O2—S1—C7110.36 (8)C2—C3—C1113.46 (15)
O3—S1—C794.28 (7)O3—C3—C4102.82 (12)
C3—O3—S1115.25 (10)C2—C3—C4111.28 (14)
C6—N1—C5116.35 (14)C1—C3—C4112.70 (14)
C4—N2—C5113.70 (13)N2—C4—C7123.46 (15)
N4—N3—C5113.33 (14)N2—C4—C3122.62 (14)
N5—N4—N3172.71 (19)C7—C4—C3113.92 (14)
C3—C1—H1A109.5N2—C5—N1128.13 (15)
C3—C1—H1B109.5N2—C5—N3113.13 (14)
H1A—C1—H1B109.5N1—C5—N3118.74 (14)
C3—C1—H1C109.5N1—C6—C7120.17 (15)
H1A—C1—H1C109.5N1—C6—H6119.9
H1B—C1—H1C109.5C7—C6—H6119.9
C3—C2—H2A109.5C6—C7—C4118.17 (15)
C3—C2—H2B109.5C6—C7—S1132.21 (13)
H2A—C2—H2B109.5C4—C7—S1109.61 (12)
C3—C2—H2C109.5
O1—S1—O3—C3136.28 (12)C6—N1—C5—N3179.13 (15)
O2—S1—O3—C393.93 (13)N4—N3—C5—N2173.41 (15)
C7—S1—O3—C319.68 (13)N4—N3—C5—N16.7 (2)
S1—O3—C3—C297.30 (15)C5—N1—C6—C70.6 (2)
S1—O3—C3—C1139.72 (13)N1—C6—C7—C41.4 (2)
S1—O3—C3—C421.11 (16)N1—C6—C7—S1179.99 (13)
C5—N2—C4—C70.8 (2)N2—C4—C7—C60.6 (2)
C5—N2—C4—C3179.56 (14)C3—C4—C7—C6179.02 (14)
O3—C3—C4—N2168.40 (14)N2—C4—C7—S1179.52 (13)
C2—C3—C4—N274.4 (2)C3—C4—C7—S10.12 (17)
C1—C3—C4—N254.4 (2)O1—S1—C7—C658.73 (19)
O3—C3—C4—C711.96 (18)O2—S1—C7—C676.20 (18)
C2—C3—C4—C7105.24 (17)O3—S1—C7—C6170.06 (17)
C1—C3—C4—C7126.00 (16)O1—S1—C7—C4122.58 (12)
C4—N2—C5—N11.8 (2)O2—S1—C7—C4102.48 (13)
C4—N2—C5—N3178.41 (14)O3—S1—C7—C411.25 (13)
C6—N1—C5—N21.1 (3)
 

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