Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768105022792/sn5022sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105022792/sn5022sup2.fcf |
CCDC reference: 1243661
Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
C2H2N4O3 | Z = 8 |
Mr = 130.08 | F(000) = 528 |
Triclinic, P1 | Dx = 1.916 Mg m−3 |
a = 5.1233 (8) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 10.3140 (16) Å | Cell parameters from 3399 reflections |
c = 17.998 (3) Å | θ = 2.6–28.2° |
α = 106.610 (2)° | µ = 0.18 mm−1 |
β = 97.810 (2)° | T = 293 K |
γ = 90.130 (2)° | Parallelpiped, colorless |
V = 902.1 (2) Å3 | 0.34 × 0.26 × 0.20 mm |
Bruker platform with 1K CCD diffractometer | 8966 independent reflections |
Radiation source: normal-focus sealed tube | 8202 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.000 |
ω–scans | θmax = 28.7°, θmin = 2.1° |
Absorption correction: multi-scan SADABS;Sheldrick1996;Blessing,ActaC.1995,A51,33 | h = −6→6 |
Tmin = 0.851, Tmax = 1.000 | k = −13→13 |
8966 measured reflections | l = −24→23 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0554P)2 + 0.2255P] where P = (Fo2 + 2Fc2)/3 |
8966 reflections | (Δ/σ)max = 0.002 |
328 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
C2H2N4O3 | γ = 90.130 (2)° |
Mr = 130.08 | V = 902.1 (2) Å3 |
Triclinic, P1 | Z = 8 |
a = 5.1233 (8) Å | Mo Kα radiation |
b = 10.3140 (16) Å | µ = 0.18 mm−1 |
c = 17.998 (3) Å | T = 293 K |
α = 106.610 (2)° | 0.34 × 0.26 × 0.20 mm |
β = 97.810 (2)° |
Bruker platform with 1K CCD diffractometer | 8966 independent reflections |
Absorption correction: multi-scan SADABS;Sheldrick1996;Blessing,ActaC.1995,A51,33 | 8202 reflections with I > 2σ(I) |
Tmin = 0.851, Tmax = 1.000 | Rint = 0.000 |
8966 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.34 e Å−3 |
8966 reflections | Δρmin = −0.36 e Å−3 |
328 parameters |
Experimental. identical or equivalent reflections were not merged |
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. Using the twin laws above, the structural model was refined as a four-component twin using the procedure associated with the HKLF 5 format for merohedral twins. Fractional contributions k1, k2, k3, k4 of the twin components were refined constraining k1 = 1 - k2 - k3 - k4. An HKLF 5 format data file was created where each line contained h,k,l, Fo2, σ(Fo2), m where m is the twin component number. Thus, four lines of the data file correspond to each measured reflection: h, k, l, Fo2, σ(Fo2), −1 h, −k, −h-l, Fo2, σ(Fo2), −2 −h, k, −k-l, Fo2, σ(Fo2), −3 −h, −k, h+k+l, Fo2, σ(Fo2), 4 The volumes of the fourling domains refine to 55: 9: 20: 16. |
x | y | z | Uiso*/Ueq | ||
N11 | 0.3084 (4) | −0.06728 (18) | 0.89274 (10) | 0.0254 (4) | |
N21 | 0.4387 (4) | −0.1449 (2) | 0.93397 (11) | 0.0264 (4) | |
H21 | 0.3621 | −0.1907 | 0.9586 | 0.037* | |
C31 | 0.7044 (5) | −0.1426 (3) | 0.93212 (13) | 0.0264 (5) | |
O31 | 0.8741 (3) | −0.20130 (18) | 0.96269 (9) | 0.0356 (4) | |
N41 | 0.7383 (4) | −0.0578 (2) | 0.88705 (10) | 0.0260 (4) | |
H41 | 0.8842 | −0.0346 | 0.8747 | 0.037* | |
C51 | 0.4949 (5) | −0.0188 (2) | 0.86632 (11) | 0.0236 (5) | |
N51 | 0.4449 (4) | 0.0715 (2) | 0.81750 (10) | 0.0272 (5) | |
O51 | 0.6354 (4) | 0.1093 (2) | 0.79429 (11) | 0.0372 (5) | |
O61 | 0.2172 (4) | 0.1003 (2) | 0.80308 (11) | 0.0409 (5) | |
N12 | 1.0939 (4) | 0.43300 (19) | 0.89177 (10) | 0.0272 (4) | |
N22 | 1.0000 (4) | 0.3554 (2) | 0.93374 (10) | 0.0285 (5) | |
H22 | 1.1004 | 0.3106 | 0.9588 | 0.037* | |
C32 | 0.7344 (5) | 0.3559 (2) | 0.93208 (13) | 0.0247 (5) | |
O32 | 0.5925 (4) | 0.29716 (17) | 0.96306 (9) | 0.0349 (4) | |
N42 | 0.6593 (4) | 0.4398 (2) | 0.88654 (10) | 0.0256 (4) | |
H42 | 0.5014 | 0.4622 | 0.8741 | 0.037* | |
C52 | 0.8799 (5) | 0.4801 (2) | 0.86520 (11) | 0.0228 (5) | |
N52 | 0.8821 (4) | 0.5705 (2) | 0.81713 (11) | 0.0266 (4) | |
O52 | 0.6643 (4) | 0.6049 (2) | 0.79464 (11) | 0.0383 (5) | |
O62 | 1.0904 (4) | 0.6061 (2) | 0.80328 (12) | 0.0443 (5) | |
N13 | −0.0965 (4) | 0.04197 (19) | 0.60938 (10) | 0.0262 (4) | |
N23 | −0.0007 (4) | −0.07541 (19) | 0.56712 (11) | 0.0263 (4) | |
H23 | −0.0993 | −0.1459 | 0.5415 | 0.037* | |
C33 | 0.2647 (5) | −0.0701 (2) | 0.56948 (13) | 0.0251 (5) | |
O33 | 0.4089 (4) | −0.15743 (16) | 0.53844 (9) | 0.0365 (4) | |
N43 | 0.3376 (4) | 0.0603 (2) | 0.61626 (11) | 0.0258 (4) | |
H43 | 0.4944 | 0.0968 | 0.6293 | 0.037* | |
C53 | 0.1129 (4) | 0.1182 (2) | 0.63718 (12) | 0.0211 (4) | |
N53 | 0.1048 (4) | 0.2559 (2) | 0.68601 (11) | 0.0266 (4) | |
O53 | 0.3155 (4) | 0.31856 (19) | 0.70961 (11) | 0.0388 (5) | |
O63 | −0.1129 (4) | 0.2971 (2) | 0.69924 (11) | 0.0422 (5) | |
N14 | 0.7013 (4) | 0.53429 (19) | 0.60426 (10) | 0.0274 (4) | |
N24 | 0.5640 (4) | 0.41422 (19) | 0.56377 (11) | 0.0259 (4) | |
H24 | 0.6379 | 0.3433 | 0.5389 | 0.037* | |
C34 | 0.3013 (5) | 0.4189 (2) | 0.56700 (13) | 0.0269 (5) | |
O34 | 0.1287 (4) | 0.33027 (16) | 0.53764 (9) | 0.0374 (4) | |
N44 | 0.2754 (4) | 0.5511 (2) | 0.61176 (11) | 0.0262 (4) | |
H44 | 0.1314 | 0.5879 | 0.6246 | 0.037* | |
C54 | 0.5181 (5) | 0.6103 (2) | 0.63109 (12) | 0.0248 (5) | |
N54 | 0.5689 (4) | 0.7486 (2) | 0.67853 (11) | 0.0271 (4) | |
O54 | 0.3796 (4) | 0.80735 (19) | 0.70440 (11) | 0.0392 (5) | |
O64 | 0.7956 (4) | 0.7932 (2) | 0.68975 (11) | 0.0423 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0224 (11) | 0.0280 (9) | 0.0272 (9) | 0.0030 (9) | 0.0016 (8) | 0.0113 (7) |
N21 | 0.0257 (11) | 0.0273 (10) | 0.0315 (9) | 0.0035 (8) | 0.0042 (8) | 0.0169 (8) |
C31 | 0.0257 (13) | 0.0275 (12) | 0.0282 (11) | 0.0016 (10) | 0.0032 (9) | 0.0115 (10) |
O31 | 0.0268 (10) | 0.0470 (10) | 0.0422 (9) | 0.0105 (8) | 0.0023 (7) | 0.0286 (7) |
N41 | 0.0203 (10) | 0.0313 (10) | 0.0302 (9) | 0.0023 (8) | 0.0013 (8) | 0.0163 (8) |
C51 | 0.0238 (12) | 0.0222 (10) | 0.0251 (10) | 0.0014 (9) | 0.0007 (9) | 0.0085 (8) |
N51 | 0.0334 (12) | 0.0247 (10) | 0.0244 (9) | 0.0037 (9) | 0.0019 (8) | 0.0094 (7) |
O51 | 0.0393 (11) | 0.0392 (11) | 0.0410 (9) | −0.0009 (9) | 0.0078 (8) | 0.0229 (8) |
O61 | 0.0323 (12) | 0.0486 (12) | 0.0479 (10) | 0.0149 (9) | 0.0014 (8) | 0.0256 (9) |
N12 | 0.0242 (11) | 0.0303 (10) | 0.0282 (9) | 0.0033 (9) | 0.0033 (8) | 0.0103 (7) |
N22 | 0.0287 (12) | 0.0298 (11) | 0.0318 (10) | 0.0034 (9) | 0.0026 (8) | 0.0173 (8) |
C32 | 0.0211 (12) | 0.0242 (12) | 0.0298 (11) | 0.0024 (9) | 0.0004 (8) | 0.0112 (9) |
O32 | 0.0280 (10) | 0.0425 (10) | 0.0432 (9) | −0.0002 (8) | 0.0041 (8) | 0.0270 (7) |
N42 | 0.0223 (11) | 0.0282 (10) | 0.0309 (9) | 0.0026 (8) | 0.0029 (8) | 0.0160 (8) |
C52 | 0.0203 (11) | 0.0248 (11) | 0.0239 (10) | 0.0021 (9) | 0.0009 (8) | 0.0088 (8) |
N52 | 0.0280 (11) | 0.0269 (10) | 0.0266 (10) | −0.0005 (8) | 0.0048 (8) | 0.0100 (8) |
O52 | 0.0382 (11) | 0.0437 (12) | 0.0390 (9) | 0.0058 (9) | −0.0018 (8) | 0.0250 (9) |
O62 | 0.0413 (12) | 0.0430 (11) | 0.0581 (11) | 0.0001 (9) | 0.0166 (9) | 0.0256 (9) |
N13 | 0.0210 (11) | 0.0246 (9) | 0.0323 (10) | 0.0035 (8) | 0.0046 (8) | 0.0069 (7) |
N23 | 0.0261 (11) | 0.0170 (9) | 0.0325 (10) | −0.0018 (8) | 0.0014 (8) | 0.0034 (7) |
C33 | 0.0308 (14) | 0.0173 (11) | 0.0261 (11) | 0.0033 (9) | 0.0044 (9) | 0.0044 (9) |
O33 | 0.0342 (10) | 0.0237 (8) | 0.0447 (9) | 0.0066 (8) | 0.0063 (8) | −0.0015 (7) |
N43 | 0.0160 (10) | 0.0210 (9) | 0.0367 (10) | 0.0024 (8) | 0.0021 (8) | 0.0033 (8) |
C53 | 0.0169 (11) | 0.0190 (10) | 0.0274 (10) | 0.0044 (8) | 0.0034 (8) | 0.0067 (8) |
N53 | 0.0283 (11) | 0.0205 (10) | 0.0304 (10) | 0.0052 (8) | 0.0042 (8) | 0.0059 (8) |
O53 | 0.0334 (11) | 0.0272 (9) | 0.0503 (10) | −0.0039 (8) | 0.0012 (8) | 0.0049 (8) |
O63 | 0.0355 (11) | 0.0350 (10) | 0.0512 (10) | 0.0125 (9) | 0.0132 (8) | 0.0013 (8) |
N14 | 0.0259 (11) | 0.0227 (9) | 0.0336 (10) | 0.0023 (8) | 0.0046 (8) | 0.0079 (7) |
N24 | 0.0256 (11) | 0.0172 (9) | 0.0318 (9) | 0.0027 (8) | 0.0063 (7) | 0.0012 (7) |
C34 | 0.0315 (14) | 0.0221 (12) | 0.0248 (11) | 0.0033 (10) | 0.0061 (9) | 0.0023 (9) |
O34 | 0.0319 (10) | 0.0236 (8) | 0.0485 (10) | −0.0058 (8) | 0.0046 (8) | −0.0018 (7) |
N44 | 0.0200 (10) | 0.0206 (9) | 0.0352 (10) | 0.0036 (8) | 0.0068 (8) | 0.0021 (7) |
C54 | 0.0267 (13) | 0.0218 (11) | 0.0248 (10) | 0.0015 (10) | 0.0054 (9) | 0.0042 (8) |
N54 | 0.0310 (12) | 0.0185 (9) | 0.0309 (10) | −0.0006 (8) | 0.0013 (8) | 0.0072 (8) |
O54 | 0.0375 (11) | 0.0264 (10) | 0.0493 (10) | 0.0061 (8) | 0.0122 (8) | 0.0012 (8) |
O64 | 0.0322 (11) | 0.0337 (10) | 0.0574 (11) | −0.0140 (9) | 0.0002 (9) | 0.0106 (9) |
N11—C51 | 1.283 (3) | N13—C53 | 1.283 (3) |
N11—N21 | 1.358 (3) | N13—N23 | 1.365 (3) |
N21—C31 | 1.367 (3) | N23—C33 | 1.355 (3) |
N21—H21 | 0.8600 | N23—H23 | 0.8600 |
C31—O31 | 1.220 (3) | C33—O33 | 1.223 (3) |
C31—N41 | 1.377 (3) | C33—N43 | 1.386 (3) |
N41—H41 | 0.8600 | N43—C53 | 1.348 (3) |
N41—C51 | 1.348 (3) | N43—H43 | 0.8600 |
C51—N51 | 1.454 (3) | C53—N53 | 1.444 (3) |
N51—O51 | 1.217 (3) | N53—O53 | 1.216 (3) |
N51—O61 | 1.217 (3) | N53—O63 | 1.224 (3) |
N12—C52 | 1.288 (3) | N14—C54 | 1.280 (3) |
N12—N22 | 1.373 (3) | N14—N24 | 1.378 (3) |
N22—C32 | 1.357 (3) | N24—C34 | 1.356 (3) |
N22—H22 | 0.8600 | N24—H24 | 0.8600 |
C32—O32 | 1.228 (3) | C34—O34 | 1.220 (3) |
C32—N42 | 1.374 (3) | C34—N44 | 1.389 (3) |
N42—C52 | 1.343 (3) | N44—C54 | 1.341 (3) |
N42—H42 | 0.8600 | N44—H44 | 0.8600 |
C52—N52 | 1.443 (3) | C54—N54 | 1.440 (3) |
N52—O62 | 1.208 (3) | N54—O64 | 1.217 (3) |
N52—O52 | 1.223 (3) | N54—O54 | 1.220 (3) |
C51—N11—N21 | 102.69 (18) | C53—N13—N23 | 102.64 (19) |
N11—N21—C31 | 112.8 (2) | C33—N23—N13 | 113.47 (19) |
N11—N21—H21 | 123.6 | C33—N23—H23 | 123.3 |
C31—N21—H21 | 123.6 | N13—N23—H23 | 123.3 |
O31—C31—N21 | 128.8 (2) | O33—C33—N23 | 129.4 (2) |
O31—C31—N41 | 127.4 (2) | O33—C33—N43 | 127.5 (2) |
N21—C31—N41 | 103.7 (2) | N23—C33—N43 | 103.10 (19) |
C51—N41—C31 | 105.5 (2) | C53—N43—C33 | 106.10 (19) |
C51—N41—H41 | 127.2 | C53—N43—H43 | 127.0 |
C31—N41—H41 | 127.2 | C33—N43—H43 | 127.0 |
N11—C51—N41 | 115.2 (2) | N13—C53—N43 | 114.70 (19) |
N11—C51—N51 | 121.9 (2) | N13—C53—N53 | 122.04 (19) |
N41—C51—N51 | 122.8 (2) | N43—C53—N53 | 123.3 (2) |
O51—N51—O61 | 126.5 (2) | O53—N53—O63 | 126.9 (2) |
O51—N51—C51 | 116.5 (2) | O53—N53—C53 | 116.43 (19) |
O61—N51—C51 | 117.0 (2) | O63—N53—C53 | 116.7 (2) |
C52—N12—N22 | 101.7 (2) | C54—N14—N24 | 102.31 (19) |
C32—N22—N12 | 113.9 (2) | C34—N24—N14 | 113.47 (19) |
C32—N22—H22 | 123.0 | C34—N24—H24 | 123.3 |
N12—N22—H22 | 123.0 | N14—N24—H24 | 123.3 |
O32—C32—N22 | 129.6 (2) | O34—C34—N24 | 129.2 (2) |
O32—C32—N42 | 127.7 (2) | O34—C34—N44 | 128.2 (2) |
N22—C32—N42 | 102.7 (2) | N24—C34—N44 | 102.6 (2) |
C52—N42—C32 | 106.9 (2) | C54—N44—C34 | 106.8 (2) |
C52—N42—H42 | 126.6 | C54—N44—H44 | 126.6 |
C32—N42—H42 | 126.6 | C34—N44—H44 | 126.6 |
N12—C52—N42 | 114.8 (2) | N14—C54—N44 | 114.8 (2) |
N12—C52—N52 | 121.7 (2) | N14—C54—N54 | 122.6 (2) |
N42—C52—N52 | 123.5 (2) | N44—C54—N54 | 122.6 (2) |
O62—N52—O52 | 126.1 (2) | O64—N54—O54 | 127.2 (2) |
O62—N52—C52 | 119.2 (2) | O64—N54—C54 | 116.8 (2) |
O52—N52—C52 | 114.6 (2) | O54—N54—C54 | 116.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O32i | 0.86 | 2.01 | 2.769 (2) | 147 |
N21—H21···O31ii | 0.86 | 2.51 | 3.089 (3) | 125 |
N41—H41···N11iii | 0.86 | 2.20 | 2.912 (3) | 141 |
N22—H22···O31iv | 0.86 | 2.04 | 2.791 (3) | 146 |
N22—H22···O32iii | 0.86 | 2.52 | 3.100 (3) | 126 |
N42—H42···N12ii | 0.86 | 2.19 | 2.913 (3) | 142 |
N23—H23···O34v | 0.86 | 2.01 | 2.778 (2) | 147 |
N23—H23···O33ii | 0.86 | 2.51 | 3.073 (3) | 123 |
N43—H43···N13iii | 0.86 | 2.22 | 2.923 (3) | 139 |
N24—H24···O33vi | 0.86 | 2.01 | 2.776 (2) | 147 |
N24—H24···O34iii | 0.86 | 2.52 | 3.081 (3) | 124 |
N44—H44···N14ii | 0.86 | 2.23 | 2.928 (3) | 139 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x−1, y, z; (iii) x+1, y, z; (iv) −x+2, −y, −z+2; (v) −x, −y, −z+1; (vi) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C2H2N4O3 |
Mr | 130.08 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 5.1233 (8), 10.3140 (16), 17.998 (3) |
α, β, γ (°) | 106.610 (2), 97.810 (2), 90.130 (2) |
V (Å3) | 902.1 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.34 × 0.26 × 0.20 |
Data collection | |
Diffractometer | Bruker platform with 1K CCD diffractometer |
Absorption correction | Multi-scan SADABS;Sheldrick1996;Blessing,ActaC.1995,A51,33 |
Tmin, Tmax | 0.851, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8966, 8966, 8202 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.676 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.115, 1.12 |
No. of reflections | 8966 |
No. of parameters | 328 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.36 |
Computer programs: SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O32i | 0.86 | 2.01 | 2.769 (2) | 146.5 |
N21—H21···O31ii | 0.86 | 2.51 | 3.089 (3) | 125.0 |
N41—H41···N11iii | 0.86 | 2.20 | 2.912 (3) | 140.6 |
N22—H22···O31iv | 0.86 | 2.04 | 2.791 (3) | 146.1 |
N22—H22···O32iii | 0.86 | 2.52 | 3.100 (3) | 125.8 |
N42—H42···N12ii | 0.86 | 2.19 | 2.913 (3) | 141.9 |
N23—H23···O34v | 0.86 | 2.01 | 2.778 (2) | 147.4 |
N23—H23···O33ii | 0.86 | 2.51 | 3.073 (3) | 123.4 |
N43—H43···N13iii | 0.86 | 2.22 | 2.923 (3) | 138.7 |
N24—H24···O33vi | 0.86 | 2.01 | 2.776 (2) | 147.4 |
N24—H24···O34iii | 0.86 | 2.52 | 3.081 (3) | 123.5 |
N44—H44···N14ii | 0.86 | 2.23 | 2.928 (3) | 138.8 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x−1, y, z; (iii) x+1, y, z; (iv) −x+2, −y, −z+2; (v) −x, −y, −z+1; (vi) −x+1, −y, −z+1. |