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The title compound, C12H16N3O2, has axial twofold symmetry and features a twist of 23.31 (8)° between the five- and six-membered rings. The N-O bond distance is 1.2777 (13) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015952/lh6088sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015952/lh6088Isup2.hkl
Contains datablock I

CCDC reference: 221720

Key indicators

  • Single-crystal X-ray study
  • T = 223 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.054
  • wR factor = 0.152
  • Data-to-parameter ratio = 22.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SHELXTL (Bruker, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHEXLTL (Bruker, 2000).

(I) top
Crystal data top
C12H16N3O2F(000) = 500
Mr = 234.28Dx = 1.303 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2ycCell parameters from 1882 reflections
a = 11.0922 (5) Åθ = 2.8–30.0°
b = 10.3891 (5) ŵ = 0.09 mm1
c = 10.8714 (6) ÅT = 223 K
β = 107.632 (2)°Block, brown
V = 1193.94 (10) Å30.31 × 0.26 × 0.26 mm
Z = 4
Data collection top
Bruker AXS SMART CCD
diffractometer
1476 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 30.0°, θmin = 2.8°
ω scansh = 1515
4911 measured reflectionsk = 1411
1753 independent reflectionsl = 1315
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0854P)2 + 0.5851P]
where P = (Fo2 + 2Fc2)/3
1753 reflections(Δ/σ)max < 0.001
79 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.34 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
O10.68596 (11)0.08767 (10)0.41872 (12)0.0525 (4)
N10.50000.53627 (15)0.25000.0373 (4)
N20.58806 (10)0.04970 (10)0.32986 (10)0.0288 (3)
C10.43936 (13)0.46832 (12)0.14522 (13)0.0343 (3)
H10.39680.51400.06990.041*
C20.43498 (11)0.33534 (11)0.13996 (11)0.0282 (3)
H20.38920.29260.06390.034*
C30.50000.26593 (15)0.25000.0231 (3)
C40.50000.12507 (15)0.25000.0227 (3)
C50.56689 (11)0.09124 (10)0.30036 (11)0.0259 (3)
C60.67366 (14)0.13565 (18)0.24908 (16)0.0470 (4)
H6A0.66750.09120.16890.070*
H6B0.66690.22770.23370.070*
H6C0.75450.11630.31200.070*
C70.57626 (15)0.16063 (13)0.42616 (13)0.0389 (3)
H7A0.50830.13220.45860.058*
H7B0.65700.14120.48920.058*
H7C0.56940.25270.41090.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0434 (6)0.0311 (5)0.0567 (7)0.0012 (4)0.0243 (5)0.0001 (4)
N10.0385 (8)0.0239 (7)0.0431 (9)0.0000.0025 (7)0.000
N20.0279 (5)0.0225 (5)0.0290 (5)0.0012 (4)0.0017 (4)0.0025 (4)
C10.0364 (7)0.0252 (6)0.0359 (7)0.0032 (5)0.0031 (5)0.0051 (5)
C20.0296 (6)0.0255 (5)0.0262 (6)0.0020 (4)0.0033 (4)0.0001 (4)
C30.0226 (7)0.0218 (7)0.0241 (7)0.0000.0056 (6)0.000
C40.0232 (7)0.0222 (7)0.0205 (7)0.0000.0032 (5)0.000
C50.0294 (6)0.0212 (5)0.0258 (5)0.0021 (4)0.0063 (4)0.0000 (4)
C60.0342 (7)0.0594 (10)0.0476 (8)0.0091 (7)0.0128 (6)0.0105 (7)
C70.0509 (8)0.0301 (6)0.0313 (6)0.0017 (6)0.0058 (6)0.0087 (5)
Geometric parameters (Å, º) top
O1—N21.2777 (13)C5—C71.5215 (17)
N1—C11.3358 (16)C5—C61.5252 (18)
N2—C41.3444 (13)C5—C5i1.555 (2)
N2—C51.5021 (14)C6—H6A0.9700
C1—C21.3829 (17)C6—H6B0.9700
C1—H10.9400C6—H6C0.9700
C2—C31.3959 (14)C7—H7A0.9700
C2—H20.9400C7—H7B0.9700
C3—C41.463 (2)C7—H7C0.9700
C1—N1—C1i116.19 (15)C7—C5—C6109.63 (12)
O1—N2—C4126.39 (11)N2—C5—C5i101.80 (6)
O1—N2—C5120.30 (10)C7—C5—C5i115.08 (12)
C4—N2—C5113.20 (10)C5—C6—H6A109.5
N1—C1—C2124.43 (12)C5—C6—H6B109.5
N1—C1—H1117.8H6A—C6—H6B109.5
C2—C1—H1117.8C5—C6—H6C109.5
C1—C2—C3118.56 (12)H6A—C6—H6C109.5
C1—C2—H2120.7H6B—C6—H6C109.5
C3—C2—H2120.7C5—C7—H7A109.5
C2i—C3—C2117.79 (15)C5—C7—H7B109.5
C2—C3—C4121.11 (7)H7A—C7—H7B109.5
N2i—C4—N2108.75 (14)C5—C7—H7C109.5
N2—C4—C3125.63 (7)H7A—C7—H7C109.5
N2—C5—C7107.83 (10)H7B—C7—H7C109.5
N2—C5—C6106.52 (11)
Symmetry code: (i) x+1, y, z+1/2.
 

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