Download citation
Download citation
link to html
The title compound, C12H8N4O, is of pharmacological interest. It contains an imidazo­[1,2-a]­pyrimidine heterocycle, carrying a nitro­so group in position 3 and a phenyl group in position 2. Both substituents are almost coplanar with the heterocycle.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011699/lh6216sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011699/lh6216Isup2.hkl
Contains datablock I

CCDC reference: 245274

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.054
  • wR factor = 0.140
  • Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PLATON.

3-Nitroso-2-phenylimidazo[1,2-a]pyrimidine top
Crystal data top
C12H8N4OF(000) = 464
Mr = 224.22Dx = 1.485 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3097 reflections
a = 7.0734 (16) Åθ = 3.5–25.4°
b = 9.2564 (16) ŵ = 0.10 mm1
c = 15.704 (4) ÅT = 173 K
β = 102.755 (18)°Block, green
V = 1002.8 (4) Å30.21 × 0.17 × 0.15 mm
Z = 4
Data collection top
Stoe IPDS-II two-circle
diffractometer
1051 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.080
Graphite monochromatorθmax = 25.5°, θmin = 3.7°
ω scansh = 58
4715 measured reflectionsk = 1111
1832 independent reflectionsl = 1818
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) = 0.140H-atom parameters constrained
S = 0.88 w = 1/[σ2(Fo2) + (0.0722P)2]
where P = (Fo2 + 2Fc2)/3
1832 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.24 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
O10.6379 (4)0.1527 (2)0.58614 (15)0.0509 (7)
N10.6869 (4)0.2853 (2)0.58655 (17)0.0409 (7)
C10.6946 (5)0.3410 (3)0.50862 (18)0.0333 (7)
C20.7380 (5)0.4856 (3)0.48993 (19)0.0310 (7)
N30.7325 (4)0.5029 (2)0.40418 (16)0.0359 (6)
C40.6889 (5)0.3721 (3)0.36644 (19)0.0342 (7)
N50.6631 (4)0.2698 (2)0.42729 (15)0.0316 (6)
C60.6199 (5)0.1294 (3)0.4029 (2)0.0368 (7)
H60.60090.05840.44390.044*
C70.6056 (5)0.0966 (3)0.3176 (2)0.0394 (7)
H70.57740.00050.29750.047*
C80.6324 (5)0.2047 (3)0.2594 (2)0.0426 (8)
H80.62250.17890.20000.051*
N90.6713 (4)0.3422 (3)0.28226 (16)0.0408 (7)
C110.7838 (4)0.6087 (3)0.55058 (19)0.0321 (7)
C120.7843 (5)0.5967 (3)0.63890 (19)0.0354 (7)
H120.75120.50740.66160.042*
C130.8330 (5)0.7151 (3)0.6942 (2)0.0416 (8)
H130.83320.70640.75450.050*
C140.8811 (5)0.8457 (3)0.6611 (2)0.0429 (8)
H140.91620.92620.69880.051*
C150.8778 (5)0.8581 (3)0.5733 (2)0.0413 (8)
H150.90930.94810.55090.050*
C160.8293 (5)0.7420 (3)0.5172 (2)0.0369 (7)
H160.82690.75230.45680.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.080 (2)0.0267 (10)0.0487 (13)0.0036 (10)0.0187 (13)0.0045 (10)
N10.0543 (19)0.0301 (12)0.0388 (14)0.0035 (11)0.0111 (13)0.0026 (11)
C10.0393 (19)0.0288 (13)0.0307 (14)0.0020 (12)0.0055 (12)0.0014 (12)
C20.0313 (17)0.0293 (13)0.0320 (16)0.0030 (11)0.0061 (13)0.0015 (11)
N30.0426 (18)0.0292 (11)0.0374 (15)0.0009 (11)0.0122 (12)0.0003 (10)
C40.040 (2)0.0316 (14)0.0316 (15)0.0014 (12)0.0101 (13)0.0023 (11)
N50.0355 (15)0.0285 (11)0.0308 (12)0.0013 (10)0.0070 (10)0.0019 (10)
C60.0356 (19)0.0298 (14)0.0441 (18)0.0002 (12)0.0069 (14)0.0040 (12)
C70.040 (2)0.0341 (14)0.0430 (18)0.0022 (13)0.0057 (14)0.0047 (13)
C80.049 (2)0.0440 (17)0.0362 (17)0.0042 (14)0.0117 (15)0.0087 (13)
N90.0470 (18)0.0410 (14)0.0366 (15)0.0004 (12)0.0141 (12)0.0021 (12)
C110.0300 (17)0.0280 (13)0.0385 (16)0.0022 (11)0.0077 (13)0.0005 (12)
C120.040 (2)0.0301 (14)0.0356 (16)0.0021 (12)0.0069 (14)0.0006 (12)
C130.048 (2)0.0405 (16)0.0347 (16)0.0065 (14)0.0062 (15)0.0019 (13)
C140.044 (2)0.0291 (14)0.053 (2)0.0027 (13)0.0043 (15)0.0078 (14)
C150.042 (2)0.0314 (14)0.0511 (19)0.0018 (13)0.0126 (15)0.0015 (13)
C160.041 (2)0.0298 (14)0.0415 (17)0.0012 (12)0.0115 (14)0.0016 (12)
Geometric parameters (Å, º) top
O1—N11.276 (3)C8—N91.334 (4)
N1—C11.340 (4)C8—H80.9500
C1—N51.411 (4)C11—C121.391 (4)
C1—C21.418 (4)C11—C161.405 (4)
C2—N31.348 (4)C12—C131.394 (4)
C2—C111.475 (4)C12—H120.9500
N3—C41.354 (4)C13—C141.387 (5)
C4—N91.329 (4)C13—H130.9500
C4—N51.386 (4)C14—C151.379 (5)
N5—C61.370 (4)C14—H140.9500
C6—C71.356 (4)C15—C161.383 (4)
C6—H60.9500C15—H150.9500
C7—C81.396 (4)C16—H160.9500
C7—H70.9500
O1—N1—C1115.6 (2)N9—C8—H8118.1
N1—C1—N5128.1 (2)C7—C8—H8118.1
N1—C1—C2127.3 (3)C4—N9—C8115.8 (3)
N5—C1—C2104.6 (2)C12—C11—C16119.5 (3)
N3—C2—C1111.0 (2)C12—C11—C2122.3 (2)
N3—C2—C11120.5 (2)C16—C11—C2118.3 (3)
C1—C2—C11128.5 (3)C11—C12—C13120.3 (3)
C2—N3—C4106.5 (2)C11—C12—H12119.8
N9—C4—N3125.7 (3)C13—C12—H12119.8
N9—C4—N5123.1 (2)C14—C13—C12119.9 (3)
N3—C4—N5111.2 (2)C14—C13—H13120.0
C6—N5—C4120.7 (2)C12—C13—H13120.0
C6—N5—C1132.6 (2)C15—C14—C13119.7 (3)
C4—N5—C1106.7 (2)C15—C14—H14120.1
C7—C6—N5116.9 (3)C13—C14—H14120.1
C7—C6—H6121.6C14—C15—C16121.3 (3)
N5—C6—H6121.6C14—C15—H15119.4
C6—C7—C8119.7 (3)C16—C15—H15119.4
C6—C7—H7120.2C15—C16—C11119.3 (3)
C8—C7—H7120.2C15—C16—H16120.3
N9—C8—C7123.8 (3)C11—C16—H16120.3
O1—N1—C1—N52.8 (5)C1—N5—C6—C7177.8 (3)
O1—N1—C1—C2177.7 (3)N5—C6—C7—C80.7 (5)
N1—C1—C2—N3180.0 (3)C6—C7—C8—N90.4 (6)
N5—C1—C2—N30.4 (3)N3—C4—N9—C8178.3 (3)
N1—C1—C2—C110.3 (5)N5—C4—N9—C82.0 (5)
N5—C1—C2—C11179.9 (3)C7—C8—N9—C41.7 (5)
C1—C2—N3—C40.8 (4)N3—C2—C11—C12177.7 (3)
C11—C2—N3—C4179.5 (3)C1—C2—C11—C122.0 (5)
C2—N3—C4—N9179.4 (3)N3—C2—C11—C162.6 (4)
C2—N3—C4—N50.9 (4)C1—C2—C11—C16177.7 (3)
N9—C4—N5—C60.9 (5)C16—C11—C12—C131.2 (5)
N3—C4—N5—C6179.3 (3)C2—C11—C12—C13178.5 (3)
N9—C4—N5—C1179.6 (3)C11—C12—C13—C140.1 (5)
N3—C4—N5—C10.6 (3)C12—C13—C14—C150.9 (5)
N1—C1—N5—C61.0 (6)C13—C14—C15—C160.8 (5)
C2—C1—N5—C6178.6 (3)C14—C15—C16—C110.4 (5)
N1—C1—N5—C4179.5 (3)C12—C11—C16—C151.4 (5)
C2—C1—N5—C40.1 (3)C2—C11—C16—C15178.3 (3)
C4—N5—C6—C70.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O10.952.362.860 (4)113
C6—H6···O1i0.952.563.211 (4)126
C12—H12···N10.952.363.034 (4)127
C13—H13···O1ii0.952.513.458 (4)172
C16—H16···N30.952.492.825 (4)101
Symmetry codes: (i) x+1, y, z+1; (ii) x+3/2, y+1/2, z+3/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds