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The mol­ecular structure of the title radical compound, C12H16N3O2, has crystallographic C2 symmetry. The dihedral angle between the pyridine and imidazole rings is 25.66 (15)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048161/xu2158sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048161/xu2158Isup2.hkl
Contains datablock I

CCDC reference: 630520

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.079
  • wR factor = 0.206
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.18 Ratio
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1999); 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, 1997); software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
C12H16N3O2F(000) = 500
Mr = 234.28Dx = 1.267 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 664 reflections
a = 11.205 (7) Åθ = 2.7–23.6°
b = 10.452 (7) ŵ = 0.09 mm1
c = 11.031 (8) ÅT = 293 K
β = 108.051 (11)°Block, blue
V = 1228.3 (14) Å30.24 × 0.20 × 0.16 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector detector
diffractometer
655 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.088
Graphite monochromatorθmax = 26.5°, θmin = 2.7°
φ and ω scansh = 1414
3365 measured reflectionsk = 813
1258 independent reflectionsl = 1113
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)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.09P)2]
where P = (Fo2 + 2Fc2)/3
1258 reflections(Δ/σ)max = 0.002
81 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.26 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
O10.1847 (2)0.0863 (2)0.4167 (3)0.0898 (12)
N10.00000.5342 (3)0.25000.0603 (12)
N20.0872 (2)0.0490 (2)0.3291 (3)0.0496 (8)
C10.0601 (3)0.4654 (3)0.3534 (3)0.0567 (10)
H10.10150.50990.42750.068*
C20.0652 (3)0.3338 (3)0.3582 (3)0.0468 (9)
H20.11130.29200.43240.056*
C30.00000.2642 (4)0.25000.0382 (10)
C40.00000.1231 (4)0.25000.0390 (10)
C50.0664 (3)0.0921 (3)0.3004 (3)0.0446 (9)
C60.1721 (3)0.1362 (4)0.2510 (4)0.0769 (12)
H6A0.16840.08980.17490.115*
H6B0.16320.22610.23240.115*
H6C0.25130.12060.31470.115*
C70.0752 (3)0.1602 (3)0.4247 (3)0.0655 (11)
H7A0.15810.14970.48340.098*
H7B0.05820.24970.40840.098*
H7C0.01490.12430.46070.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0813 (18)0.0494 (15)0.093 (2)0.0023 (12)0.0389 (17)0.0021 (13)
N10.074 (3)0.038 (2)0.061 (3)0.0000.009 (2)0.000
N20.0532 (16)0.0382 (15)0.0435 (17)0.0023 (11)0.0051 (13)0.0032 (11)
C10.069 (2)0.042 (2)0.050 (2)0.0043 (15)0.0039 (18)0.0085 (15)
C20.057 (2)0.0359 (18)0.040 (2)0.0044 (13)0.0043 (16)0.0016 (13)
C30.041 (2)0.035 (2)0.036 (3)0.0000.009 (2)0.000
C40.043 (2)0.037 (2)0.031 (2)0.0000.004 (2)0.000
C50.0574 (19)0.0297 (15)0.045 (2)0.0031 (13)0.0129 (15)0.0019 (13)
C60.065 (2)0.090 (3)0.074 (3)0.012 (2)0.020 (2)0.015 (2)
C70.090 (3)0.045 (2)0.052 (2)0.0020 (17)0.008 (2)0.0111 (16)
Geometric parameters (Å, º) top
O1—N21.274 (3)C4—N2i1.337 (3)
N1—C1i1.340 (4)C5—C61.519 (5)
N1—C11.340 (4)C5—C71.521 (4)
N2—C41.337 (3)C5—C5i1.558 (6)
N2—C51.512 (4)C6—H6A0.9600
C1—C21.376 (4)C6—H6B0.9600
C1—H10.9300C6—H6C0.9600
C2—C31.395 (3)C7—H7A0.9600
C2—H20.9300C7—H7B0.9600
C3—C2i1.395 (3)C7—H7C0.9600
C3—C41.475 (6)
C1i—N1—C1115.1 (4)N2—C5—C7107.7 (3)
O1—N2—C4126.8 (3)C6—C5—C7109.9 (3)
O1—N2—C5119.8 (2)N2—C5—C5i101.58 (14)
C4—N2—C5113.2 (2)C6—C5—C5i115.0 (3)
N1—C1—C2125.0 (3)C7—C5—C5i115.1 (3)
N1—C1—H1117.5C5—C6—H6A109.5
C2—C1—H1117.5C5—C6—H6B109.5
C1—C2—C3118.9 (3)H6A—C6—H6B109.5
C1—C2—H2120.6C5—C6—H6C109.5
C3—C2—H2120.6H6A—C6—H6C109.5
C2—C3—C2i117.2 (4)H6B—C6—H6C109.5
C2—C3—C4121.41 (19)C5—C7—H7A109.5
C2i—C3—C4121.41 (19)C5—C7—H7B109.5
N2i—C4—N2109.3 (4)H7A—C7—H7B109.5
N2i—C4—C3125.36 (18)C5—C7—H7C109.5
N2—C4—C3125.36 (18)H7A—C7—H7C109.5
N2—C5—C6106.5 (3)H7B—C7—H7C109.5
C1i—N1—C1—C21.2 (2)C2i—C3—C4—N2i22.8 (2)
N1—C1—C2—C32.4 (5)C2—C3—C4—N222.8 (2)
C1—C2—C3—C2i1.1 (2)C2i—C3—C4—N2157.2 (2)
C1—C2—C3—C4178.9 (2)O1—N2—C5—C664.5 (4)
O1—N2—C4—N2i179.5 (4)C4—N2—C5—C6111.5 (3)
C5—N2—C4—N2i3.84 (16)O1—N2—C5—C753.4 (4)
O1—N2—C4—C30.5 (4)C4—N2—C5—C7130.6 (3)
C5—N2—C4—C3176.16 (16)O1—N2—C5—C5i174.7 (3)
C2—C3—C4—N2i157.2 (2)C4—N2—C5—C5i9.3 (4)
Symmetry code: (i) x, y, z+1/2.
 

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