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The molecular structure of the title compound, C9H12N6O5, shows extensive electronic delocalization involving the pyrimidine ring and the attached N atom of the glycyl­glycinate, the amino and the nitro­so groups. A unique O—H...N(nitro­so) hydrogen bond of 2.748 (2) Å is found in the structure. The supramolecular structure is a three-dimensional network, derived from two sets of antiparallel chains, which link chains of alternating dimers which are formed by the action of two different crystallographic centres of symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802013405/bt6170sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802013405/bt6170Isup2.hkl
Contains datablock I

CCDC reference: 193784

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.044
  • wR factor = 0.122
  • Data-to-parameter ratio = 12.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

N-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)glycylglycinate top
Crystal data top
C9H12N6O5Z = 2
Mr = 284.25F(000) = 296
Triclinic, P1Dx = 1.654 Mg m3
a = 7.4727 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.2356 (4) ÅCell parameters from 2321 reflections
c = 9.6678 (8) Åθ = 2.8–26.4°
α = 81.208 (5)°µ = 0.14 mm1
β = 88.722 (3)°T = 150 K
γ = 76.169 (4)°Lath, pink
V = 570.87 (7) Å30.30 × 0.10 × 0.05 mm
Data collection top
Nonius KappaCCD
diffractometer
1775 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.055
Graphite monochromatorθmax = 26.4°, θmin = 2.8°
φ scans, and ω scans with κ offsetsh = 99
9202 measured reflectionsk = 1010
2321 independent reflectionsl = 1212
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0708P)2 + 0.0612P]
where P = (Fo2 + 2Fc2)/3
2321 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.29 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.05280 (18)0.18922 (17)0.89256 (15)0.0192 (3)
C20.0767 (2)0.14057 (19)0.82871 (17)0.0173 (4)
N210.03039 (19)0.06320 (17)0.71766 (15)0.0209 (3)
O210.19347 (18)0.13079 (15)0.42403 (13)0.0279 (3)
C210.1581 (2)0.0233 (2)0.66617 (19)0.0228 (4)
C220.1881 (2)0.1563 (2)0.54673 (18)0.0199 (4)
C230.2292 (2)0.4355 (2)0.46741 (18)0.0216 (4)
N220.20505 (19)0.30442 (17)0.57857 (15)0.0207 (3)
C240.4118 (2)0.3857 (2)0.39476 (18)0.0212 (4)
O220.40469 (17)0.46401 (16)0.26383 (13)0.0285 (3)
O230.54798 (17)0.29061 (15)0.45079 (13)0.0285 (3)
N30.25716 (18)0.16244 (16)0.87142 (14)0.0186 (3)
C30.3936 (2)0.1091 (2)0.79169 (19)0.0247 (4)
C40.3177 (2)0.2441 (2)0.98567 (18)0.0193 (4)
O40.47819 (17)0.26204 (16)1.02333 (14)0.0295 (3)
C50.1799 (2)0.3025 (2)1.05510 (17)0.0190 (4)
N50.24506 (19)0.38923 (17)1.15932 (15)0.0209 (3)
O50.13407 (17)0.44616 (16)1.22710 (13)0.0276 (3)
C60.0068 (2)0.26640 (19)1.00554 (18)0.0182 (4)
N60.13781 (19)0.30838 (18)1.07150 (15)0.0225 (3)
H210.11700.03470.67320.025*
H21A0.18380.08820.63370.027*
H21B0.24550.01570.74370.027*
H23A0.22360.54090.50650.026*
H23B0.12730.45840.39810.026*
H22A0.20150.32170.66630.025*
H22B0.53410.42050.22090.034*
H3A0.39880.16550.69440.037*
H3B0.51520.14030.83370.037*
H3C0.35740.01380.79400.037*
H6A0.25170.28571.04120.027*
H6B0.11130.35901.14580.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0161 (7)0.0220 (7)0.0209 (8)0.0060 (5)0.0037 (6)0.0056 (6)
C20.0189 (9)0.0156 (8)0.0168 (9)0.0052 (6)0.0016 (7)0.0008 (6)
N210.0195 (8)0.0256 (7)0.0209 (8)0.0094 (6)0.0043 (6)0.0080 (6)
O210.0375 (8)0.0314 (7)0.0213 (7)0.0165 (6)0.0068 (6)0.0117 (5)
C210.0215 (9)0.0236 (9)0.0245 (10)0.0059 (7)0.0074 (7)0.0072 (7)
C220.0145 (9)0.0252 (9)0.0213 (9)0.0050 (6)0.0034 (7)0.0074 (7)
C230.0207 (9)0.0228 (9)0.0225 (10)0.0069 (7)0.0042 (7)0.0056 (7)
N220.0229 (8)0.0248 (7)0.0171 (8)0.0082 (6)0.0048 (6)0.0080 (6)
C240.0216 (10)0.0208 (8)0.0232 (10)0.0076 (7)0.0017 (7)0.0059 (7)
O220.0263 (7)0.0352 (7)0.0196 (7)0.0015 (5)0.0070 (5)0.0003 (5)
O230.0201 (7)0.0331 (7)0.0291 (8)0.0030 (5)0.0027 (6)0.0004 (6)
N30.0168 (8)0.0220 (7)0.0186 (8)0.0069 (5)0.0013 (6)0.0048 (6)
C30.0182 (9)0.0343 (10)0.0249 (10)0.0095 (7)0.0021 (7)0.0092 (8)
C40.0165 (9)0.0213 (8)0.0198 (9)0.0048 (6)0.0024 (7)0.0023 (7)
O40.0173 (7)0.0443 (8)0.0307 (8)0.0102 (5)0.0058 (5)0.0136 (6)
C50.0184 (9)0.0214 (8)0.0175 (9)0.0052 (6)0.0023 (7)0.0031 (7)
N50.0212 (8)0.0249 (7)0.0180 (8)0.0085 (6)0.0025 (6)0.0031 (6)
O50.0268 (7)0.0359 (7)0.0251 (7)0.0116 (5)0.0015 (5)0.0135 (6)
C60.0178 (9)0.0193 (8)0.0176 (9)0.0064 (6)0.0011 (7)0.0007 (6)
N60.0156 (8)0.0322 (8)0.0226 (8)0.0076 (6)0.0030 (6)0.0101 (6)
Geometric parameters (Å, º) top
N1—C21.329 (2)C24—O231.207 (2)
N1—C61.344 (2)C24—O221.326 (2)
C2—N211.329 (2)O22—H22B1.0477
C2—N31.380 (2)N3—C41.392 (2)
N21—C211.462 (2)N3—C31.476 (2)
N21—H210.88C3—H3A0.98
O21—C221.234 (2)C3—H3B0.98
C21—C221.517 (2)C3—H3C0.98
C21—H21A0.99C4—O41.227 (2)
C21—H21B0.99C4—C51.452 (2)
C22—N221.338 (2)C5—N51.340 (2)
C23—N221.443 (2)C5—C61.442 (2)
C23—C241.517 (2)N5—O51.2811 (18)
C23—H23A0.99C6—N61.320 (2)
C23—H23B0.99N6—H6A0.88
N22—H22A0.88N6—H6B0.88
C2—N1—C6118.63 (14)O23—C24—C23124.05 (16)
N21—C2—N1118.47 (15)O22—C24—C23111.58 (14)
N21—C2—N3117.23 (14)C24—O22—H22B106.7
N1—C2—N3124.29 (15)C2—N3—C4120.91 (13)
C2—N21—C21122.88 (14)C2—N3—C3120.71 (13)
C2—N21—H21118.6C4—N3—C3118.27 (13)
C21—N21—H21118.6N3—C3—H3A109.5
N21—C21—C22111.63 (14)N3—C3—H3B109.5
N21—C21—H21A109.3H3A—C3—H3B109.5
C22—C21—H21A109.3N3—C3—H3C109.5
N21—C21—H21B109.3H3A—C3—H3C109.5
C22—C21—H21B109.3H3B—C3—H3C109.5
H21A—C21—H21B108.0O4—C4—N3120.40 (15)
O21—C22—N22120.79 (16)O4—C4—C5123.73 (15)
O21—C22—C21121.54 (15)N3—C4—C5115.87 (14)
N22—C22—C21117.66 (15)N5—C5—C6127.04 (15)
N22—C23—C24111.66 (14)N5—C5—C4114.32 (14)
N22—C23—H23A109.3C6—C5—C4118.63 (14)
C24—C23—H23A109.3O5—N5—C5119.06 (14)
N22—C23—H23B109.3N6—C6—N1118.20 (15)
C24—C23—H23B109.3N6—C6—C5120.24 (15)
H23A—C23—H23B107.9N1—C6—C5121.56 (14)
C22—N22—C23119.25 (14)C6—N6—H6A120.0
C22—N22—H22A120.4C6—N6—H6B120.0
C23—N22—H22A120.4H6A—N6—H6B120.0
O23—C24—O22124.34 (16)
C6—N1—C2—N21179.51 (14)C2—N3—C4—O4179.56 (15)
C6—N1—C2—N30.7 (2)C3—N3—C4—O44.2 (2)
N1—C2—N21—C212.5 (2)C2—N3—C4—C50.3 (2)
N3—C2—N21—C21176.41 (14)C3—N3—C4—C5176.52 (14)
C2—N21—C21—C2296.96 (18)O4—C4—C5—N54.5 (2)
N21—C21—C22—O21103.45 (18)N3—C4—C5—N5176.26 (14)
N21—C21—C22—N2275.27 (19)O4—C4—C5—C6176.84 (15)
O21—C22—N22—C230.2 (2)N3—C4—C5—C62.4 (2)
C21—C22—N22—C23178.48 (14)C6—C5—N5—O51.4 (3)
C24—C23—N22—C2266.09 (19)C4—C5—N5—O5179.98 (13)
N22—C23—C24—O2328.4 (2)C2—N1—C6—N6177.42 (14)
N22—C23—C24—O22153.69 (14)C2—N1—C6—C52.3 (2)
N21—C2—N3—C4179.17 (14)N5—C5—C6—N65.6 (3)
N1—C2—N3—C42.0 (2)C4—C5—C6—N6175.85 (14)
N21—C2—N3—C33.0 (2)N5—C5—C6—N1174.68 (16)
N1—C2—N3—C3178.13 (15)C4—C5—C6—N13.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O22—H22B···N5i1.051.722.748 (2)168
N21—H21···O21ii0.881.962.755 (2)149
N22—H22A···N10.882.643.300 (2)133
N22—H22A···O5iii0.882.262.940 (2)135
N6—H6A···O4iv0.881.992.840 (2)163
N6—H6B···O50.881.992.638 (2)129
Symmetry codes: (i) x+1, y, z1; (ii) x, y, z+1; (iii) x, y+1, z+2; (iv) x+1, y, z.
 

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