N-(6-Amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl) derivatives of glycine, valine, serine, threonine and methionine: interplay of molecular, molecular–electronic and supramolecular structures

In each of N-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)valine, C₁₀H₁₅N₅O₄ (3) (orthorhombic, P2₁2₁2₁), N-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxo­pyrimidin-2-yl)serine monohydrate, C₈H₁₁N₅O₅·H₂O (4) (orthorhombic, P2₁2₁2₁), and N-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)threonine, C₉H₁₃N₅O₅(5) (monoclinic, P2₁), the C-nitroso fragments exhibit almost equal C—N and N—O bond lengths: the C—N range is 1.315 (3)–1.329 (3) Å and the N—O range is 1.293 (3)–1.326 (3) Å. In each compound there are also very short intermolecular O—H...O hydrogen bonds, in which carboxyl groups act as hydrogen-bond donors to the nitrosyl O atoms: the O...O distances range from 2.440 (2) to 2.504 (4) Å and the O—H...O angles lie between 161 and 163°. An interpretation of the relationship between the unusual intramolecular bond lengths and the very short intermolecular hydrogen bonds has been developed based on database analysis and computational modelling. In each of (3)–(5) there is an extensive network of intermolecular hydrogen bonds, generating three-dimensional frameworks in (3) and (5), and two-dimensional sheets in (4).

S1. Comment

In full text version

S2. Experimental

In full text version

S3. Refinement

In full text version

Computing details

Data collection: CAD4 (Enraf-Nonius, 1992) for 9878, 9881; Kappa-CCD server software (Nonius, 1997) for 283. Cell refinement: SET4 & CELDIM (Enraf-Nonius, 1992) for 9878, 9881; DENZO (Otwinowski & Minor, 1997) for 283. Data reduction: DATRD2 in NRCVAX96 (Gabe et al., 1989) for 9878, 9881; DENZO (Otwinowski & Minor, 1997) for 283. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: PLATON (Spek, 1999). Software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998) for 9878, 9881; SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999) for 283.

Figures

(9878) N-(6-Amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl) Valine

Crystal data

C10H15N5O4	? #Insert any comments here.
Mr = 269.27	Dx = 1.366 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.7093 Å
a = 8.9136 (6) Å	Cell parameters from 25 reflections
b = 11.2501 (6) Å	θ = 9.3–18.9°
c = 13.0585 (12) Å	µ = 0.11 mm^−1
V = 1309.49 (16) Å^3	T = 294 K
Z = 4	Needle, orange
F(000) = 568	0.42 × 0.29 × 0.28 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.019
Radiation source: X-ray tube	θmax = 27.4°, θmin = 2.4°
Graphite monochromator	h = −11→11
θ/2θ scans	k = −14→14
3011 measured reflections	l = −16→16
1738 independent reflections	3 standard reflections every 120 min
1375 reflections with I > 2σ(I)	intensity decay: 0.7%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0782P)^2 + 0.2134P] where P = (Fo^2 + 2Fc^2)/3
1738 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.28 e Å^−3
7 restraints	Δρmin = −0.25 e Å^−3

Special details

Experimental. ? #Insert any special details here.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.2942 (3)	0.44881 (18)	0.0569 (2)	0.0395 (5)
C2	0.1879 (3)	0.4069 (2)	0.1164 (2)	0.0327 (5)
N3	0.0688 (3)	0.47182 (18)	0.15295 (18)	0.0354 (5)
C3	−0.0587 (4)	0.4131 (3)	0.2033 (3)	0.0518 (8)
C4	0.0651 (3)	0.5957 (2)	0.1402 (2)	0.0343 (6)
O4	−0.0350 (2)	0.65428 (18)	0.17899 (18)	0.0496 (6)
C5	0.1853 (3)	0.6450 (2)	0.0781 (2)	0.0342 (6)
N5	0.1884 (3)	0.76300 (19)	0.07436 (19)	0.0422 (6)
O5	0.2906 (3)	0.81031 (16)	0.01713 (18)	0.0518 (6)
C6	0.2927 (3)	0.5647 (2)	0.0315 (2)	0.0345 (6)
N6	0.3960 (3)	0.6015 (2)	−0.0315 (2)	0.0479 (6)
N2	0.1952 (3)	0.29198 (18)	0.14207 (18)	0.0387 (5)
C21	0.3180 (3)	0.2160 (2)	0.1076 (2)	0.0403 (6)
C211	0.2514 (3)	0.0959 (2)	0.0798 (2)	0.0382 (6)
O21	0.3511 (3)	0.02366 (18)	0.0431 (3)	0.0720 (8)
O22	0.1211 (2)	0.07316 (18)	0.0913 (2)	0.0535 (6)
C22	0.4438 (4)	0.2086 (4)	0.1868 (3)	0.0782 (12)
C23A	0.4071 (6)	0.1479 (7)	0.2819 (4)	0.085 (2)	0.701 (6)
C23B	0.4475 (17)	0.3014 (13)	0.2689 (11)	0.099 (6)*	0.299 (6)
C24A	0.5920 (6)	0.1769 (9)	0.1466 (6)	0.134 (4)	0.701 (6)
C24B	0.5334 (12)	0.3198 (7)	0.1977 (9)	0.057 (3)*	0.299 (6)
H3A	−0.1344	0.4710	0.2189	0.078*
H3B	−0.0252	0.3761	0.2655	0.078*
H3C	−0.0996	0.3538	0.1585	0.078*
H6A	0.4613	0.5523	−0.0550	0.057*
H6B	0.3989	0.6750	−0.0496	0.057*
H2	0.1257	0.2621	0.1799	0.046*
H21	0.3141	−0.0469	0.0400	0.108*
H21A	0.3598	0.2509	0.0451	0.048*
H22A	0.4560	0.2916	0.2081	0.094*	0.701 (6)
H22B	0.4933	0.1322	0.1993	0.094*	0.299 (6)
H23A	0.3264	0.1888	0.3154	0.127*	0.350 (3)
H23B	0.4935	0.1472	0.3258	0.127*	0.350 (3)
H23C	0.3773	0.0677	0.2672	0.127*	0.350 (3)
H23D	0.4717	0.0803	0.2902	0.127*	0.350 (3)
H23E	0.3046	0.1220	0.2799	0.127*	0.350 (3)
H23F	0.4208	0.2014	0.3384	0.127*	0.350 (3)
H23G	0.4858	0.3743	0.2411	0.148*	0.150 (3)
H23H	0.5113	0.2753	0.3237	0.148*	0.150 (3)
H23I	0.3479	0.3141	0.2945	0.148*	0.150 (3)
H23J	0.4108	0.2681	0.3318	0.148*	0.150 (3)
H23K	0.3854	0.3672	0.2492	0.148*	0.150 (3)
H23L	0.5488	0.3283	0.2783	0.148*	0.150 (3)
H24A	0.6195	0.2316	0.0934	0.202*	0.350 (3)
H24B	0.5889	0.0977	0.1193	0.202*	0.350 (3)
H24C	0.6647	0.1805	0.2008	0.202*	0.350 (3)
H24D	0.6292	0.1083	0.1822	0.202*	0.350 (3)
H24E	0.6598	0.2422	0.1563	0.202*	0.350 (3)
H24F	0.5840	0.1593	0.0749	0.202*	0.350 (3)
H24G	0.5387	0.3595	0.1327	0.086*	0.150 (3)
H24H	0.6328	0.3004	0.2204	0.086*	0.150 (3)
H24I	0.4863	0.3710	0.2469	0.086*	0.150 (3)
H24J	0.5665	0.3277	0.2673	0.086*	0.150 (3)
H24K	0.4724	0.3869	0.1796	0.086*	0.150 (3)
H24L	0.6189	0.3162	0.1531	0.086*	0.150 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0406 (12)	0.0186 (9)	0.0593 (13)	0.0038 (9)	0.0087 (12)	−0.0018 (9)
C2	0.0363 (12)	0.0196 (10)	0.0422 (12)	0.0000 (10)	−0.0019 (12)	−0.0026 (9)
N3	0.0389 (12)	0.0211 (9)	0.0462 (12)	0.0007 (9)	0.0056 (11)	−0.0011 (9)
C3	0.0519 (17)	0.0344 (15)	0.069 (2)	0.0009 (14)	0.0196 (17)	0.0018 (14)
C4	0.0374 (13)	0.0225 (11)	0.0429 (13)	0.0049 (11)	−0.0009 (12)	−0.0031 (10)
O4	0.0512 (12)	0.0324 (10)	0.0653 (14)	0.0093 (10)	0.0162 (11)	−0.0001 (10)
C5	0.0407 (14)	0.0201 (10)	0.0419 (13)	0.0033 (11)	0.0013 (13)	−0.0036 (10)
N5	0.0512 (14)	0.0220 (10)	0.0534 (13)	0.0044 (10)	0.0061 (13)	−0.0013 (9)
O5	0.0677 (14)	0.0195 (8)	0.0682 (13)	−0.0003 (9)	0.0204 (12)	−0.0007 (9)
C6	0.0368 (13)	0.0192 (10)	0.0476 (14)	0.0008 (10)	0.0044 (12)	−0.0035 (10)
N6	0.0520 (14)	0.0206 (10)	0.0710 (16)	0.0028 (10)	0.0218 (13)	−0.0004 (11)
N2	0.0423 (12)	0.0191 (9)	0.0548 (13)	0.0016 (10)	0.0082 (11)	−0.0002 (9)
C21	0.0382 (14)	0.0203 (11)	0.0624 (16)	0.0023 (11)	0.0012 (14)	−0.0043 (11)
C211	0.0473 (15)	0.0209 (11)	0.0463 (14)	−0.0013 (11)	0.0050 (13)	0.0001 (11)
O21	0.0687 (16)	0.0241 (10)	0.123 (2)	−0.0032 (10)	0.0363 (16)	−0.0137 (12)
O22	0.0484 (12)	0.0326 (11)	0.0794 (17)	−0.0066 (9)	0.0005 (12)	−0.0157 (11)
C22	0.061 (2)	0.070 (3)	0.104 (3)	0.007 (2)	−0.031 (2)	−0.016 (2)
C23A	0.053 (3)	0.128 (6)	0.074 (4)	−0.006 (4)	−0.007 (3)	0.037 (4)
C24A	0.064 (4)	0.198 (11)	0.140 (7)	0.047 (6)	−0.017 (5)	−0.042 (8)

Geometric parameters (Å, º)

N1—C2	1.313 (3)	C6—N6	1.303 (4)
N1—C6	1.345 (3)	N2—C21	1.460 (3)
C2—N2	1.337 (3)	C21—C211	1.519 (4)
C2—N3	1.374 (3)	C21—C22	1.528 (5)
N3—C4	1.404 (3)	C211—O22	1.199 (4)
N3—C3	1.470 (4)	C211—O21	1.296 (3)
C4—O4	1.219 (3)	C22—C23A	1.454 (4)
C4—C5	1.453 (4)	C22—C24A	1.466 (4)
C5—N5	1.329 (3)	C22—C24B	1.491 (5)
C5—C6	1.450 (3)	C22—C23B	1.496 (5)
N5—O5	1.293 (3)
C2—N1—C6	119.1 (2)	C2—N2—C21	121.7 (2)
N1—C2—N2	117.4 (2)	N2—C21—C211	107.5 (2)
N1—C2—N3	124.9 (2)	N2—C21—C22	111.9 (3)
N2—C2—N3	117.7 (2)	C211—C21—C22	113.6 (3)
C2—N3—C4	120.3 (2)	O22—C211—O21	125.2 (3)
C2—N3—C3	120.9 (2)	O22—C211—C21	122.6 (3)
C4—N3—C3	118.8 (2)	O21—C211—C21	112.2 (2)
O4—C4—N3	120.3 (3)	C23A—C22—C24A	113.2 (5)
O4—C4—C5	124.4 (2)	C23A—C22—C24B	115.7 (5)
N3—C4—C5	115.3 (2)	C24A—C22—C24B	75.9 (6)
N5—C5—C6	126.4 (3)	C23A—C22—C23B	73.8 (8)
N5—C5—C4	114.7 (2)	C24A—C22—C23B	114.0 (6)
C6—C5—C4	118.9 (2)	C24B—C22—C23B	48.3 (7)
O5—N5—C5	116.6 (2)	C23A—C22—C21	116.0 (4)
N6—C6—N1	117.2 (2)	C24A—C22—C21	115.6 (4)
N6—C6—C5	122.3 (2)	C24B—C22—C21	114.3 (5)
N1—C6—C5	120.5 (2)	C23B—C22—C21	117.6 (7)
C6—N1—C2—N2	−178.3 (3)	C4—C5—C6—N6	174.4 (3)
C6—N1—C2—N3	2.6 (4)	N5—C5—C6—N1	167.1 (3)
N1—C2—N3—C4	−9.4 (4)	C4—C5—C6—N1	−9.4 (4)
N2—C2—N3—C4	171.5 (3)	N1—C2—N2—C21	1.4 (4)
N1—C2—N3—C3	168.8 (3)	N3—C2—N2—C21	−179.5 (2)
N2—C2—N3—C3	−10.2 (4)	C2—N2—C21—C211	−140.1 (3)
C2—N3—C4—O4	−174.7 (2)	C2—N2—C21—C22	94.5 (3)
C3—N3—C4—O4	7.0 (4)	N2—C21—C211—O22	−3.3 (4)
C2—N3—C4—C5	6.0 (4)	C22—C21—C211—O22	121.1 (3)
C3—N3—C4—C5	−172.3 (2)	N2—C21—C211—O21	176.7 (3)
O4—C4—C5—N5	6.6 (4)	C22—C21—C211—O21	−58.9 (4)
N3—C4—C5—N5	−174.2 (3)	N2—C21—C22—C23A	67.4 (5)
O4—C4—C5—C6	−176.5 (3)	C211—C21—C22—C23A	−54.6 (5)
N3—C4—C5—C6	2.8 (4)	N2—C21—C22—C24A	−156.5 (5)
C6—C5—N5—O5	5.6 (5)	C211—C21—C22—C24A	81.4 (6)
C4—C5—N5—O5	−177.7 (2)	N2—C21—C22—C24B	−71.2 (6)
C2—N1—C6—N6	−176.8 (3)	C211—C21—C22—C24B	166.8 (6)
C2—N1—C6—C5	6.8 (4)	N2—C21—C22—C23B	−17.2 (9)
N5—C5—C6—N6	−9.0 (5)	C211—C21—C22—C23B	−139.2 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4^i	0.86	2.35	3.146 (3)	154
N6—H6A···O22^ii	0.86	2.06	2.915 (3)	172
N6—H6B···O5	0.86	2.00	2.609 (3)	127
O21—H21···O5^iii	0.86	1.65	2.483 (3)	163
O21—H21···N5^iii	0.86	2.46	3.297 (3)	166
C3—H3A···O4	0.96	2.31	2.743 (3)	107
C21—H21A···N1	0.98	2.31	2.708 (2)	104

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x+1/2, −y+1/2, −z; (iii) x, y−1, z.

(9881) N-(6-Amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl) Serine Monohydrate

Crystal data

C8H11N5O5·H2O	? #Insert any comments here.
Mr = 275.23	Dx = 1.632 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.7107 Å
a = 6.5574 (7) Å	Cell parameters from 25 reflections
b = 7.686 (2) Å	θ = 10.0–12.5°
c = 22.222 (3) Å	µ = 0.14 mm^−1
V = 1119.9 (4) Å^3	T = 294 K
Z = 4	Block, orange
F(000) = 576	0.24 × 0.18 × 0.12 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.062
Radiation source: X-ray tube	θmax = 25.4°, θmin = 2.8°
Graphite monochromator	h = −7→7
θ/2θ scans	k = −9→9
2082 measured reflections	l = −26→26
1239 independent reflections	3 standard reflections every 180 min
791 reflections with I > 2σ(I)	intensity decay: no decay, variation 1.0%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0524P)^2] where P = (Fo^2 + 2Fc^2)/3
1239 reflections	(Δ/σ)max = 0.004
176 parameters	Δρmax = 0.20 e Å^−3
2 restraints	Δρmin = −0.20 e Å^−3

Special details

Experimental. ? #Insert any special details here.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.7715 (7)	0.1261 (4)	0.92512 (15)	0.0284 (10)
C2	0.7741 (8)	−0.0138 (6)	0.89140 (19)	0.0277 (11)
N2	0.7625 (6)	0.0059 (5)	0.83201 (14)	0.0303 (10)
C21	0.7557 (9)	0.1784 (6)	0.80524 (19)	0.0330 (14)
C22	0.9646 (10)	0.2648 (7)	0.8073 (2)	0.0480 (17)
O23	1.1045 (7)	0.1755 (5)	0.77039 (17)	0.0568 (12)
C211	0.6897 (10)	0.1723 (7)	0.7400 (2)	0.0419 (15)
O21	0.6704 (7)	0.0198 (4)	0.71797 (13)	0.0480 (11)
O22	0.6642 (10)	0.3051 (5)	0.71265 (14)	0.0821 (19)
N3	0.7888 (7)	−0.1823 (4)	0.91299 (15)	0.0265 (10)
C3	0.8012 (10)	−0.3311 (6)	0.87179 (18)	0.0414 (15)
C4	0.8014 (8)	−0.2135 (6)	0.97400 (18)	0.0284 (11)
O4	0.8107 (7)	−0.3621 (4)	0.99262 (13)	0.0431 (11)
C5	0.8063 (9)	−0.0602 (5)	1.01289 (18)	0.0272 (12)
N5	0.8244 (7)	−0.0953 (5)	1.07072 (15)	0.0347 (11)
O5	0.8318 (7)	0.0373 (4)	1.10705 (13)	0.0412 (10)
C6	0.7899 (8)	0.1093 (6)	0.98460 (17)	0.0263 (12)
N6	0.7943 (7)	0.2517 (5)	1.01643 (14)	0.0345 (11)
O1	0.7693 (7)	−0.4915 (5)	1.11193 (16)	0.0609 (13)
H2	0.7590	−0.0845	0.8092	0.036*
H21A	0.6587	0.2501	0.8278	0.040*
H22A	0.9530	0.3844	0.7938	0.058*
H22B	1.0143	0.2657	0.8484	0.058*
H23	1.1624	0.1001	0.7902	0.085*
H21	0.6757	0.0249	0.6811	0.072*
H3A	0.6789	−0.3371	0.8481	0.062*
H3B	0.8160	−0.4364	0.8946	0.062*
H3C	0.9167	−0.3171	0.8457	0.062*
H6A	0.7855	0.3513	0.9989	0.041*
H6B	0.8060	0.2462	1.0549	0.041*
H11	0.8230	−0.3996	1.1366	0.091*
H12	0.7719	−0.4194	1.0787	0.091*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.035 (3)	0.0276 (19)	0.0223 (18)	0.003 (2)	0.003 (2)	0.0001 (17)
C2	0.029 (3)	0.036 (3)	0.0182 (19)	−0.002 (3)	0.000 (2)	0.004 (2)
N2	0.046 (3)	0.0281 (19)	0.0167 (17)	0.000 (2)	−0.0009 (19)	−0.0007 (16)
C21	0.051 (4)	0.026 (2)	0.022 (2)	0.004 (3)	0.001 (2)	0.0027 (19)
C22	0.081 (5)	0.032 (3)	0.031 (3)	−0.005 (4)	0.008 (3)	−0.002 (2)
O23	0.064 (3)	0.046 (3)	0.060 (3)	−0.003 (2)	0.016 (2)	0.001 (2)
C211	0.062 (4)	0.041 (3)	0.023 (2)	0.017 (4)	0.001 (3)	0.000 (2)
O21	0.076 (3)	0.049 (2)	0.0191 (16)	0.001 (3)	−0.002 (2)	−0.0024 (16)
O22	0.164 (6)	0.053 (2)	0.029 (2)	0.040 (3)	−0.008 (3)	0.0102 (18)
N3	0.035 (3)	0.0239 (19)	0.0207 (17)	−0.005 (2)	0.0036 (19)	−0.0036 (15)
C3	0.068 (4)	0.032 (3)	0.025 (2)	0.001 (3)	0.006 (3)	−0.0030 (19)
C4	0.031 (3)	0.029 (2)	0.026 (2)	0.000 (3)	−0.003 (2)	0.002 (2)
O4	0.075 (3)	0.0264 (18)	0.0280 (17)	0.003 (2)	−0.002 (2)	0.0026 (15)
C5	0.034 (3)	0.028 (2)	0.020 (2)	−0.001 (3)	0.003 (3)	0.0019 (18)
N5	0.048 (3)	0.037 (2)	0.0188 (17)	0.000 (3)	0.002 (2)	0.0010 (18)
O5	0.068 (3)	0.0378 (18)	0.0175 (14)	0.003 (2)	−0.001 (2)	−0.0045 (14)
C6	0.027 (3)	0.031 (2)	0.020 (2)	−0.001 (3)	0.005 (2)	0.002 (2)
N6	0.057 (3)	0.0281 (19)	0.0187 (19)	0.003 (3)	0.000 (2)	−0.0025 (18)
O1	0.098 (4)	0.040 (2)	0.0444 (19)	−0.013 (3)	0.001 (3)	−0.0013 (19)

Geometric parameters (Å, º)

N1—C2	1.311 (6)	C211—O21	1.276 (6)
N1—C6	1.334 (5)	N3—C4	1.379 (5)
C2—N2	1.331 (5)	N3—C3	1.467 (5)
C2—N3	1.385 (5)	C4—O4	1.216 (5)
N2—C21	1.453 (5)	C4—C5	1.461 (6)
C21—C211	1.515 (6)	C5—N5	1.319 (5)
C21—C22	1.523 (7)	C5—C6	1.451 (6)
C22—O23	1.409 (6)	N5—O5	1.301 (5)
C211—O22	1.199 (6)	C6—N6	1.303 (5)
C2—N1—C6	119.1 (4)	C4—N3—C3	118.3 (4)
N1—C2—N2	118.2 (4)	C2—N3—C3	121.1 (3)
N1—C2—N3	124.8 (4)	O4—C4—N3	120.0 (4)
N2—C2—N3	117.0 (4)	O4—C4—C5	123.7 (4)
C2—N2—C21	120.8 (4)	N3—C4—C5	116.3 (4)
N2—C21—C211	111.9 (4)	N5—C5—C6	127.8 (4)
N2—C21—C22	111.0 (4)	N5—C5—C4	114.4 (4)
C211—C21—C22	107.4 (4)	C6—C5—C4	117.8 (4)
O23—C22—C21	110.8 (4)	O5—N5—C5	116.6 (4)
O22—C211—O21	125.0 (4)	N6—C6—N1	117.3 (4)
O22—C211—C21	119.9 (5)	N6—C6—C5	121.2 (4)
O21—C211—C21	115.0 (4)	N1—C6—C5	121.5 (4)
C4—N3—C2	120.5 (3)
C6—N1—C2—N2	−177.7 (5)	C2—N3—C4—O4	178.7 (5)
C6—N1—C2—N3	2.0 (8)	C3—N3—C4—O4	−4.1 (9)
N1—C2—N2—C21	2.5 (8)	C2—N3—C4—C5	−2.3 (8)
N3—C2—N2—C21	−177.3 (5)	C3—N3—C4—C5	174.8 (5)
C2—N2—C21—C211	−165.6 (4)	O4—C4—C5—N5	0.8 (9)
C2—N2—C21—C22	74.5 (6)	N3—C4—C5—N5	−178.1 (5)
N2—C21—C22—O23	66.1 (5)	O4—C4—C5—C6	−178.9 (6)
C211—C21—C22—O23	−56.5 (5)	N3—C4—C5—C6	2.2 (7)
N2—C21—C211—O22	175.3 (6)	C6—C5—N5—O5	−1.1 (9)
C22—C21—C211—O22	−62.7 (8)	C4—C5—N5—O5	179.2 (5)
N2—C21—C211—O21	−6.3 (8)	C2—N1—C6—N6	177.5 (5)
C22—C21—C211—O21	115.7 (6)	C2—N1—C6—C5	−2.0 (8)
N1—C2—N3—C4	0.3 (8)	N5—C5—C6—N6	0.8 (9)
N2—C2—N3—C4	−180.0 (5)	C4—C5—C6—N6	−179.6 (6)
N1—C2—N3—C3	−176.8 (6)	N5—C5—C6—N1	−179.8 (6)
N2—C2—N3—C3	2.9 (7)	C4—C5—C6—N1	−0.2 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21···O5^i	0.82	1.71	2.504 (4)	161
N6—H6A···O4^ii	0.86	2.21	3.017 (5)	155
N6—H6B···O5	0.86	1.99	2.614 (5)	129
O11—H11···O22^iii	0.96	1.84	2.693 (5)	146
O1—H12···O4	0.92	1.98	2.845 (5)	155

Symmetry codes: (i) −x+3/2, −y, z−1/2; (ii) x, y+1, z; (iii) −x+3/2, −y, z+1/2.

(283) N-(6-Amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl) Threonine

Crystal data

C9H13N5O5	F(000) = 284
Mr = 271.24	Dx = 1.548 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 8.3686 (3) Å	Cell parameters from 1434 reflections
b = 6.7077 (3) Å	θ = 2.0–27.4°
c = 11.1230 (4) Å	µ = 0.13 mm^−1
β = 111.265 (2)°	T = 150 K
V = 581.86 (4) Å^3	Block, orange
Z = 2	0.20 × 0.20 × 0.20 mm

Data collection

Kappa-CCD diffractometer	1434 independent reflections
Radiation source: fine-focus sealed X-ray tube	1271 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ϕ scans and ω scans with κ offsets	θmax = 27.4°, θmin = 2.0°
Absorption correction: multi-scan SORTAV (Blessing, 1995 & 1997)	h = −10→10
Tmin = 0.941, Tmax = 0.975	k = −7→8
5604 measured reflections	l = −12→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 0.1096P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.002
1434 reflections	Δρmax = 0.34 e Å^−3
177 parameters	Δρmin = −0.39 e Å^−3
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (7)

Special details

Experimental. Kappa CCD diffractometer using the following programs. Collect: Data collection software, Hooft, 1998, is a graphical user interface written by Enraf–Nonius which encompasses the following programs. DENZO (Otwinowski and Minor, 1997) and indexing and data collection software package and a scaling package, SCALEPACK both of which programs are produced by the company HKL. Absorption corrections are performed by the SORTAV package, Blessing, 1995 and Blessing, 1997. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. Low temperature data is collected using an Oxford Cryosystems cryostream, Cosier and Glazer, 1986.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.6322 (2)	0.2314 (3)	0.72246 (17)	0.0175 (5)
C2	0.7867 (3)	0.1730 (4)	0.7262 (2)	0.0150 (5)
N2	0.8231 (2)	0.2000 (3)	0.62015 (17)	0.0171 (4)
H2	0.9282	0.1597	0.6181	0.020*
C21	0.7064 (3)	0.3051 (4)	0.5075 (2)	0.0172 (5)
H21A	0.5953	0.3162	0.5179	0.021*
C211	0.6783 (3)	0.1891 (4)	0.3833 (2)	0.0188 (5)
O21	0.5715 (2)	0.2748 (3)	0.28340 (15)	0.0267 (5)
H21	0.5819	0.2290	0.2183	0.040*
O22	0.7525 (2)	0.0298 (3)	0.38294 (16)	0.0249 (4)
C22	0.7685 (3)	0.5177 (4)	0.4957 (2)	0.0199 (5)
H22	0.6764	0.5854	0.4267	0.024*
C23	0.8059 (3)	0.6389 (5)	0.6184 (2)	0.0263 (6)
H23A	0.9018	0.5817	0.6863	0.039*
H23B	0.7071	0.6379	0.6430	0.039*
H23C	0.8324	0.7737	0.6035	0.039*
O23	0.9138 (2)	0.5073 (3)	0.45745 (16)	0.0242 (4)
H23	1.0019	0.5163	0.5213	0.036*
N3	0.9085 (2)	0.0856 (3)	0.83134 (18)	0.0177 (5)
C31	1.0823 (3)	0.0517 (5)	0.8332 (2)	0.0292 (7)
H31A	1.0808	−0.0564	0.7762	0.044*
H31B	1.1569	0.0189	0.9193	0.044*
H31C	1.1229	0.1703	0.8053	0.044*
C4	0.8808 (3)	0.0550 (4)	0.9468 (2)	0.0192 (5)
O4	0.9893 (2)	−0.0234 (3)	1.03834 (15)	0.0290 (5)
C5	0.7138 (3)	0.1271 (4)	0.9468 (2)	0.0183 (5)
N5	0.6985 (3)	0.1210 (4)	1.06032 (19)	0.0224 (5)
O5	0.5530 (2)	0.1918 (3)	1.06517 (15)	0.0249 (4)
C6	0.5934 (3)	0.2126 (4)	0.8280 (2)	0.0174 (5)
N6	0.4427 (2)	0.2759 (4)	0.82242 (18)	0.0209 (5)
H6A	0.3727	0.3275	0.7523	0.025*
H6B	0.4138	0.2659	0.8889	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0186 (9)	0.0215 (12)	0.0129 (9)	0.0019 (8)	0.0063 (7)	0.0016 (8)
C2	0.0187 (10)	0.0135 (13)	0.0119 (10)	−0.0036 (9)	0.0046 (8)	−0.0009 (9)
N2	0.0168 (9)	0.0206 (10)	0.0147 (9)	0.0004 (8)	0.0067 (7)	0.0012 (9)
C21	0.0169 (10)	0.0232 (14)	0.0118 (11)	0.0001 (10)	0.0055 (8)	0.0014 (10)
C211	0.0178 (11)	0.0242 (14)	0.0172 (11)	−0.0035 (10)	0.0095 (9)	−0.0011 (10)
O21	0.0300 (9)	0.0388 (12)	0.0124 (8)	0.0062 (8)	0.0087 (7)	−0.0001 (8)
O22	0.0250 (9)	0.0276 (11)	0.0195 (8)	0.0003 (8)	0.0051 (7)	−0.0045 (8)
C22	0.0193 (11)	0.0251 (13)	0.0176 (11)	0.0012 (11)	0.0093 (9)	0.0032 (11)
C23	0.0346 (14)	0.0228 (14)	0.0236 (12)	−0.0024 (13)	0.0130 (11)	−0.0026 (12)
O23	0.0195 (8)	0.0346 (11)	0.0200 (8)	−0.0040 (8)	0.0092 (7)	0.0024 (9)
N3	0.0171 (9)	0.0208 (12)	0.0151 (9)	0.0015 (8)	0.0057 (8)	0.0008 (8)
C31	0.0209 (12)	0.0440 (19)	0.0225 (12)	0.0081 (12)	0.0076 (10)	0.0037 (13)
C4	0.0238 (12)	0.0194 (13)	0.0157 (11)	−0.0003 (10)	0.0085 (9)	0.0005 (10)
O4	0.0316 (10)	0.0370 (14)	0.0186 (9)	0.0118 (9)	0.0092 (8)	0.0099 (8)
C5	0.0215 (11)	0.0191 (12)	0.0143 (10)	−0.0006 (10)	0.0065 (9)	−0.0008 (10)
N5	0.0257 (11)	0.0245 (12)	0.0187 (10)	−0.0001 (9)	0.0098 (8)	0.0022 (9)
O5	0.0260 (9)	0.0348 (11)	0.0164 (8)	0.0023 (9)	0.0108 (7)	0.0006 (8)
C6	0.0203 (10)	0.0184 (13)	0.0149 (11)	−0.0015 (10)	0.0080 (9)	−0.0012 (10)
N6	0.0212 (10)	0.0303 (12)	0.0131 (9)	0.0041 (9)	0.0085 (8)	0.0016 (9)

Geometric parameters (Å, º)

N1—C2	1.337 (3)	C23—H23B	0.9600
N1—C6	1.333 (3)	C23—H23C	0.9600
C2—N2	1.333 (3)	O23—H23	0.8200
C2—N3	1.374 (3)	N3—C4	1.400 (3)
N2—C21	1.461 (3)	N3—C31	1.465 (3)
N2—H2	0.9283	C31—H31A	0.9600
C21—C211	1.528 (3)	C31—H31B	0.9600
C21—C22	1.539 (4)	C31—H31C	0.9600
C21—H21A	0.9800	C4—O4	1.211 (3)
C211—O22	1.237 (3)	C4—C5	1.479 (3)
C211—O21	1.282 (3)	C5—N5	1.315 (3)
O21—H21	0.8200	C5—C6	1.458 (3)
C22—O23	1.428 (3)	N5—O5	1.326 (3)
C22—C23	1.521 (4)	C6—N6	1.311 (3)
C22—H22	0.9800	N6—H6A	0.8600
C23—H23A	0.9600	N6—H6B	0.8600
C6—N1—C2	119.15 (19)	C22—C23—H23C	109.5
N2—C2—N1	117.5 (2)	H23A—C23—H23C	109.5
N2—C2—N3	118.3 (2)	H23B—C23—H23C	109.5
N1—C2—N3	124.2 (2)	C22—O23—H23	109.5
C2—N2—C21	121.84 (19)	C2—N3—C4	121.70 (19)
C2—N2—H2	120.4	C2—N3—C31	120.3 (2)
C21—N2—H2	117.7	C4—N3—C31	117.25 (19)
N2—C21—C211	111.4 (2)	N3—C31—H31A	109.5
N2—C21—C22	112.25 (18)	N3—C31—H31B	109.5
C211—C21—C22	109.91 (18)	H31A—C31—H31B	109.5
N2—C21—H21A	107.7	N3—C31—H31C	109.5
C211—C21—H21A	107.7	H31A—C31—H31C	109.5
C22—C21—H21A	107.7	H31B—C31—H31C	109.5
O22—C211—O21	125.3 (2)	O4—C4—N3	120.8 (2)
O22—C211—C21	122.0 (2)	O4—C4—C5	124.2 (2)
O21—C211—C21	112.7 (2)	N3—C4—C5	115.0 (2)
C211—O21—H21	109.5	N5—C5—C6	127.4 (2)
O23—C22—C23	111.9 (2)	N5—C5—C4	114.3 (2)
O23—C22—C21	109.3 (2)	C6—C5—C4	118.1 (2)
C23—C22—C21	112.6 (2)	C5—N5—O5	116.01 (19)
O23—C22—H22	107.6	N6—C6—N1	117.8 (2)
C23—C22—H22	107.6	N6—C6—C5	120.4 (2)
C21—C22—H22	107.6	N1—C6—C5	121.8 (2)
C22—C23—H23A	109.5	C6—N6—H6A	120.0
C22—C23—H23B	109.5	C6—N6—H6B	120.0
H23A—C23—H23B	109.5	H6A—N6—H6B	120.0
C6—N1—C2—N2	−177.9 (2)	N1—C2—N3—C31	−171.5 (3)
C6—N1—C2—N3	2.9 (4)	C2—N3—C4—O4	179.6 (2)
N1—C2—N2—C21	5.4 (3)	C31—N3—C4—O4	−10.3 (4)
N3—C2—N2—C21	−175.3 (2)	C2—N3—C4—C5	−1.2 (3)
C2—N2—C21—C211	−131.9 (2)	C31—N3—C4—C5	168.9 (2)
C2—N2—C21—C22	104.3 (2)	O4—C4—C5—N5	7.6 (4)
N2—C21—C211—O22	−2.2 (3)	N3—C4—C5—N5	−171.7 (2)
C22—C21—C211—O22	122.9 (2)	O4—C4—C5—C6	−178.0 (2)
N2—C21—C211—O21	177.68 (19)	N3—C4—C5—C6	2.8 (3)
C22—C21—C211—O21	−57.2 (2)	C6—C5—N5—O5	3.6 (4)
N2—C21—C22—O23	72.0 (2)	C4—C5—N5—O5	177.4 (2)
C211—C21—C22—O23	−52.6 (2)	C2—N1—C6—N6	178.2 (2)
N2—C21—C22—C23	−53.1 (3)	C2—N1—C6—C5	−1.0 (4)
C211—C21—C22—C23	−177.7 (2)	N5—C5—C6—N6	−7.4 (4)
N2—C2—N3—C4	179.0 (2)	C4—C5—C6—N6	179.0 (2)
N1—C2—N3—C4	−1.7 (4)	N5—C5—C6—N1	171.8 (3)
N2—C2—N3—C31	9.2 (3)	C4—C5—C6—N1	−1.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O23^i	0.93	2.08	2.940 (3)	154
N6—H6A···O22^ii	0.86	2.02	2.843 (3)	161
N6—H6B···O5	0.86	1.95	2.579 (2)	129
O21—H21···O5^iii	0.82	1.65	2.440 (2)	161
O23—H23···O22^iv	0.82	1.94	2.716 (2)	157

Symmetry codes: (i) −x+2, y−1/2, −z+1; (ii) −x+1, y+1/2, −z+1; (iii) x, y, z−1; (iv) −x+2, y+1/2, −z+1.