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The title compound, C12H23N3, was prepared and its crystal structure was determined. The five-membered N—C=C—C=N fragment is planar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803002605/ww6060sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803002605/ww6060Isup2.hkl
Contains datablock I

CCDC reference: 206773

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.065
  • wR factor = 0.144
  • Data-to-parameter ratio = 15.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N(3) - H(1) ? PLAT_420 Alert C D-H Without Acceptor N(2) - H(3) ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C12H23N3F(000) = 464
Mr = 209.33Dx = 1.113 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1558 reflections
a = 10.409 (2) Åθ = 2.3–27.4°
b = 6.133 (2) ŵ = 0.07 mm1
c = 19.665 (4) ÅT = 153 K
β = 95.386 (3)°Block, colorless
V = 1249.7 (4) Å30.20 × 0.20 × 0.10 mm
Z = 4
Data collection top
Siemens CCD area-detector
diffractometer
2317 independent reflections
Radiation source: fine-focus sealed tube1807 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.987, Tmax = 0.993k = 73
5024 measured reflectionsl = 2323
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0538P)2 + 0.7086P]
where P = (Fo2 + 2Fc2)/3
2317 reflections(Δ/σ)max < 0.001
151 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.17 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
N10.07866 (16)0.7472 (3)0.14258 (9)0.0263 (5)
N20.2245 (2)0.3046 (4)0.21482 (10)0.0311 (5)
N30.0106 (2)0.4759 (4)0.22529 (10)0.0357 (5)
C20.1179 (2)0.5456 (4)0.13388 (11)0.0254 (5)
H20.12060.61550.09210.030*
C30.0072 (2)0.5878 (4)0.17113 (11)0.0261 (5)
C40.2012 (2)0.7748 (4)0.17193 (11)0.0310 (6)
H4A0.18720.85550.21440.037*
H4B0.23610.63300.18200.037*
C50.2969 (2)0.8965 (4)0.12273 (12)0.0325 (6)
H5A0.31790.80770.08240.039*
H5B0.37590.92060.14420.039*
C10.2188 (2)0.4120 (4)0.15476 (11)0.0235 (5)
C90.3336 (2)0.3795 (4)0.11313 (11)0.0260 (5)
C80.0237 (2)0.9584 (4)0.12413 (12)0.0301 (6)
H8A0.05720.93360.10460.036*
H8B0.00581.04600.16500.036*
C100.3492 (2)0.1359 (4)0.09740 (13)0.0344 (6)
H10A0.36450.05630.13940.052*
H10B0.42100.11650.07070.052*
H10C0.27200.08280.07230.052*
C60.2441 (2)1.1139 (5)0.10165 (13)0.0381 (7)
H6A0.23391.21070.14080.046*
H6B0.30431.18080.06720.046*
C70.1147 (2)1.0812 (4)0.07337 (12)0.0372 (6)
H7A0.12681.00010.03090.045*
H7B0.07771.22190.06380.045*
C110.4562 (2)0.4619 (4)0.15537 (13)0.0399 (7)
H11A0.44630.61350.16590.060*
H11B0.52930.44360.12950.060*
H11C0.46950.37990.19700.060*
C120.3195 (2)0.5043 (4)0.04579 (12)0.0359 (6)
H12A0.24330.45580.01870.054*
H12B0.39370.47820.02140.054*
H12C0.31260.65750.05480.054*
H40.153 (2)0.304 (4)0.2371 (11)0.028 (7)*
H10.078 (2)0.523 (4)0.2436 (12)0.039 (7)*
H30.286 (3)0.209 (5)0.2245 (12)0.040 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0204 (10)0.0273 (11)0.0319 (10)0.0019 (8)0.0067 (8)0.0020 (9)
N20.0290 (12)0.0303 (13)0.0338 (11)0.0063 (10)0.0023 (10)0.0065 (10)
N30.0351 (12)0.0397 (14)0.0342 (12)0.0072 (11)0.0138 (10)0.0053 (10)
C20.0275 (12)0.0247 (13)0.0243 (11)0.0003 (10)0.0037 (9)0.0047 (10)
C30.0272 (12)0.0256 (13)0.0253 (11)0.0011 (10)0.0009 (9)0.0000 (10)
C40.0284 (12)0.0342 (15)0.0311 (12)0.0007 (11)0.0069 (10)0.0002 (11)
C50.0214 (11)0.0439 (16)0.0325 (12)0.0025 (11)0.0039 (9)0.0046 (12)
C10.0245 (12)0.0196 (12)0.0256 (11)0.0034 (10)0.0024 (9)0.0020 (10)
C90.0228 (11)0.0227 (13)0.0322 (12)0.0006 (10)0.0012 (9)0.0022 (10)
C80.0232 (12)0.0265 (14)0.0407 (13)0.0006 (10)0.0037 (10)0.0009 (11)
C100.0316 (13)0.0294 (15)0.0417 (14)0.0049 (11)0.0015 (11)0.0055 (12)
C60.0309 (13)0.0418 (17)0.0412 (14)0.0110 (12)0.0025 (11)0.0056 (13)
C70.0317 (14)0.0371 (16)0.0431 (14)0.0003 (12)0.0039 (11)0.0105 (13)
C110.0276 (13)0.0389 (16)0.0530 (16)0.0055 (12)0.0030 (11)0.0102 (13)
C120.0345 (14)0.0352 (15)0.0404 (14)0.0072 (12)0.0157 (11)0.0011 (12)
Geometric parameters (Å, º) top
N1—C31.405 (3)C9—C101.538 (3)
N1—C41.458 (3)C9—C111.542 (3)
N1—C81.475 (3)C8—C71.511 (3)
N2—C11.349 (3)C8—H8A0.9700
N2—H40.90 (2)C8—H8B0.9700
N2—H30.88 (3)C10—H10A0.9600
N3—C31.295 (3)C10—H10B0.9600
N3—H10.87 (3)C10—H10C0.9600
C2—C11.364 (3)C6—C71.518 (3)
C2—C31.446 (3)C6—H6A0.9700
C2—H20.9300C6—H6B0.9700
C4—C51.518 (3)C7—H7A0.9700
C4—H4A0.9700C7—H7B0.9700
C4—H4B0.9700C11—H11A0.9600
C5—C61.515 (4)C11—H11B0.9600
C5—H5A0.9700C11—H11C0.9600
C5—H5B0.9700C12—H12A0.9600
C1—C91.524 (3)C12—H12B0.9600
C9—C121.524 (3)C12—H12C0.9600
C3—N1—C4118.01 (18)N1—C8—H8A109.3
C3—N1—C8117.53 (17)C7—C8—H8A109.3
C4—N1—C8111.65 (18)N1—C8—H8B109.3
C1—N2—H4117.2 (15)C7—C8—H8B109.3
C1—N2—H3119.1 (17)H8A—C8—H8B108.0
H4—N2—H3121 (2)C9—C10—H10A109.5
C3—N3—H1110.3 (17)C9—C10—H10B109.5
C1—C2—C3125.7 (2)H10A—C10—H10B109.5
C1—C2—H2117.2C9—C10—H10C109.5
C3—C2—H2117.2H10A—C10—H10C109.5
N3—C3—N1124.2 (2)H10B—C10—H10C109.5
N3—C3—C2120.3 (2)C5—C6—C7110.0 (2)
N1—C3—C2115.43 (19)C5—C6—H6A109.7
N1—C4—C5110.56 (18)C7—C6—H6A109.7
N1—C4—H4A109.5C5—C6—H6B109.7
C5—C4—H4A109.5C7—C6—H6B109.7
N1—C4—H4B109.5H6A—C6—H6B108.2
C5—C4—H4B109.5C8—C7—C6110.3 (2)
H4A—C4—H4B108.1C8—C7—H7A109.6
C6—C5—C4111.94 (19)C6—C7—H7A109.6
C6—C5—H5A109.2C8—C7—H7B109.6
C4—C5—H5A109.2C6—C7—H7B109.6
C6—C5—H5B109.2H7A—C7—H7B108.1
C4—C5—H5B109.2C9—C11—H11A109.5
H5A—C5—H5B107.9C9—C11—H11B109.5
N2—C1—C2121.8 (2)H11A—C11—H11B109.5
N2—C1—C9115.7 (2)C9—C11—H11C109.5
C2—C1—C9122.49 (19)H11A—C11—H11C109.5
C1—C9—C12112.63 (18)H11B—C11—H11C109.5
C1—C9—C10109.79 (19)C9—C12—H12A109.5
C12—C9—C10108.44 (19)C9—C12—H12B109.5
C1—C9—C11108.62 (18)H12A—C12—H12B109.5
C12—C9—C11108.1 (2)C9—C12—H12C109.5
C10—C9—C11109.19 (19)H12A—C12—H12C109.5
N1—C8—C7111.51 (19)H12B—C12—H12C109.5
 

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