Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S002188980300092X/do0018sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S002188980300092X/do0018100sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S002188980300092X/do0018150sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S002188980300092X/do0018200sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S002188980300092X/do0018250sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S002188980300092X/do0018298sup6.hkl |
CCDC references: 200142; 200143; 200144; 200145; 200146
For all compounds, data collection: Bruker SMART; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: Bruker SHELXTL; program(s) used to refine structure: Bruker SHELXTL; molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.
C2H2N4O3 | F(000) = 264 |
Mr = 130.08 | Dx = 1.926 Mg m−3 |
Monoclinic, P21/c | Ag Kα radiation, λ = 0.56086 Å |
a = 9.3129 (4) Å | Cell parameters from 1406 reflections |
b = 5.4458 (2) Å | θ = 1.8–35.5° |
c = 9.0261 (3) Å | µ = 0.11 mm−1 |
β = 101.464 (1)° | T = 100 K |
V = 448.64 (3) Å3 | Plate-like, colorless |
Z = 4 | 0.24 × 0.08 × 0.02 mm |
Bruker platform diffractometer | 1036 independent reflections |
Radiation source: fine-focus sealed tube | 1036 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω scans | θmax = 35.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −18→13 |
Tmin = 0.919, Tmax = 1.000 | k = −10→7 |
2922 measured reflections | l = −18→18 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | Calculated w = 1/[σ2(Fo2) + (0.0576P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
1036 reflections | Δρmax = 0.56 e Å−3 |
90 parameters | Δρmin = −0.28 e Å−3 |
0 restraints |
C2H2N4O3 | V = 448.64 (3) Å3 |
Mr = 130.08 | Z = 4 |
Monoclinic, P21/c | Ag Kα radiation, λ = 0.56086 Å |
a = 9.3129 (4) Å | µ = 0.11 mm−1 |
b = 5.4458 (2) Å | T = 100 K |
c = 9.0261 (3) Å | 0.24 × 0.08 × 0.02 mm |
β = 101.464 (1)° |
Bruker platform diffractometer | 1036 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1036 reflections with I > 2σ(I) |
Tmin = 0.919, Tmax = 1.000 | Rint = 0.034 |
2922 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 90 parameters |
wR(F2) = 0.093 | 0 restraints |
S = 1.10 | Δρmax = 0.56 e Å−3 |
1036 reflections | Δρmin = −0.28 e Å−3 |
Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS |
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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. |
x | y | z | Uiso*/Ueq | ||
N2 | 0.6539 (2) | 0.7348 (3) | 0.2358 (2) | 0.0110 (3) | |
H2 | 0.583 (3) | 0.636 (5) | 0.199 (3) | 0.027 (7)* | |
O3 | 0.86326 (15) | 0.5898 (2) | 0.1599 (2) | 0.0126 (3) | |
N1 | 0.6154 (2) | 0.9264 (3) | 0.3183 (2) | 0.0111 (3) | |
N4 | 0.8523 (2) | 0.9462 (3) | 0.3060 (2) | 0.0092 (3) | |
H4 | 0.946 (3) | 0.998 (5) | 0.318 (3) | 0.025 (7)* | |
C3 | 0.7983 (2) | 0.7401 (3) | 0.2253 (2) | 0.0096 (3) | |
O5B | 0.8698 (2) | 1.3632 (2) | 0.4765 (2) | 0.0161 (3) | |
O5A | 0.6410 (2) | 1.3248 (2) | 0.4979 (2) | 0.0181 (3) | |
N5 | 0.7507 (2) | 1.2608 (3) | 0.4511 (2) | 0.0115 (3) | |
C5 | 0.7380 (2) | 1.0440 (3) | 0.3573 (2) | 0.0095 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.0077 (6) | 0.0097 (6) | 0.0154 (7) | −0.0006 (5) | 0.0018 (5) | −0.0029 (5) |
O3 | 0.0103 (6) | 0.0133 (5) | 0.0144 (6) | 0.0023 (5) | 0.0029 (5) | −0.0031 (5) |
N1 | 0.0098 (7) | 0.0101 (6) | 0.0134 (7) | 0.0016 (5) | 0.0026 (5) | −0.0007 (5) |
N4 | 0.0060 (6) | 0.0103 (6) | 0.0114 (7) | −0.0006 (5) | 0.0019 (5) | −0.0013 (5) |
C3 | 0.0078 (6) | 0.0109 (7) | 0.0098 (7) | −0.0010 (6) | 0.0005 (5) | 0.0006 (6) |
O5B | 0.0155 (7) | 0.0139 (6) | 0.0187 (7) | −0.0056 (5) | 0.0032 (5) | −0.0020 (5) |
O5A | 0.0153 (7) | 0.0198 (6) | 0.0199 (8) | 0.0042 (5) | 0.0051 (6) | −0.0061 (5) |
N5 | 0.0122 (7) | 0.0107 (6) | 0.0113 (7) | −0.0010 (6) | 0.0021 (5) | 0.0005 (5) |
C5 | 0.0100 (7) | 0.0088 (7) | 0.0097 (7) | 0.0002 (5) | 0.0022 (6) | −0.0002 (5) |
N2—C3 | 1.368 (2) | N4—C3 | 1.377 (2) |
N2—N1 | 1.370 (2) | O5B—N5 | 1.222 (2) |
O3—C3 | 1.235 (2) | O5A—N5 | 1.230 (2) |
N1—C5 | 1.295 (2) | N5—C5 | 1.444 (2) |
N4—C5 | 1.352 (2) | ||
C3—N2—N1 | 112.85 (14) | O5B—N5—O5A | 126.2 (2) |
C5—N1—N2 | 102.31 (14) | O5B—N5—C5 | 116.65 (15) |
C5—N4—C3 | 105.83 (14) | O5A—N5—C5 | 117.11 (15) |
O3—C3—N2 | 126.9 (2) | N1—C5—N4 | 115.1 (2) |
O3—C3—N4 | 129.1 (2) | N1—C5—N5 | 121.9 (2) |
N2—C3—N4 | 103.96 (14) | N4—C5—N5 | 123.01 (15) |
C2H2N4O3 | F(000) = 264 |
Mr = 130.08 | Dx = 1.914 Mg m−3 |
Monoclinic, P21/c | Ag Kα radiation, λ = 0.56086 Å |
a = 9.3185 (4) Å | Cell parameters from 1287 reflections |
b = 5.4615 (2) Å | θ = 1.8–33.4° |
c = 9.0475 (3) Å | µ = 0.10 mm−1 |
β = 101.332 (1)° | T = 150 K |
V = 451.48 (3) Å3 | Plate-like, colorless |
Z = 4 | 0.24 × 0.08 × 0.02 mm |
Bruker platform diffractometer | 894 independent reflections |
Radiation source: fine-focus sealed tube | 894 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω–scan | θmax = 33.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→13 |
Tmin = 0.912, Tmax = 1.000 | k = −10→7 |
2578 measured reflections | l = −16→15 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | Calculated w = 1/[σ2(Fo2) + (0.0607P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
894 reflections | Δρmax = 0.53 e Å−3 |
90 parameters | Δρmin = −0.24 e Å−3 |
0 restraints |
C2H2N4O3 | V = 451.48 (3) Å3 |
Mr = 130.08 | Z = 4 |
Monoclinic, P21/c | Ag Kα radiation, λ = 0.56086 Å |
a = 9.3185 (4) Å | µ = 0.10 mm−1 |
b = 5.4615 (2) Å | T = 150 K |
c = 9.0475 (3) Å | 0.24 × 0.08 × 0.02 mm |
β = 101.332 (1)° |
Bruker platform diffractometer | 894 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 894 reflections with I > 2σ(I) |
Tmin = 0.912, Tmax = 1.000 | Rint = 0.030 |
2578 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 90 parameters |
wR(F2) = 0.092 | 0 restraints |
S = 1.08 | Δρmax = 0.53 e Å−3 |
894 reflections | Δρmin = −0.24 e Å−3 |
Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS |
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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. |
x | y | z | Uiso*/Ueq | ||
N2 | 0.6538 (2) | 0.7362 (3) | 0.2357 (2) | 0.0149 (3) | |
H2 | 0.585 (3) | 0.640 (5) | 0.198 (3) | 0.027 (7)* | |
O3 | 0.8630 (2) | 0.5905 (2) | 0.1601 (2) | 0.0176 (3) | |
N1 | 0.6155 (2) | 0.9272 (3) | 0.3179 (2) | 0.0147 (3) | |
N4 | 0.8522 (2) | 0.9456 (3) | 0.3060 (2) | 0.0124 (3) | |
H4 | 0.945 (4) | 0.995 (6) | 0.318 (4) | 0.046 (9)* | |
C3 | 0.7987 (2) | 0.7406 (3) | 0.2251 (2) | 0.0127 (3) | |
O5B | 0.8699 (2) | 1.3613 (3) | 0.4764 (2) | 0.0222 (3) | |
O5A | 0.6413 (2) | 1.3242 (3) | 0.4975 (2) | 0.0258 (4) | |
N5 | 0.7507 (2) | 1.2599 (3) | 0.4508 (2) | 0.0164 (3) | |
C5 | 0.7378 (2) | 1.0433 (3) | 0.3572 (2) | 0.0131 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.0089 (7) | 0.0142 (7) | 0.0214 (8) | −0.0019 (6) | 0.0024 (6) | −0.0039 (6) |
O3 | 0.0132 (7) | 0.0199 (7) | 0.0195 (7) | 0.0028 (5) | 0.0027 (6) | −0.0045 (6) |
N1 | 0.0107 (7) | 0.0151 (7) | 0.0180 (8) | 0.0009 (6) | 0.0023 (6) | −0.0012 (6) |
N4 | 0.0083 (7) | 0.0139 (7) | 0.0150 (8) | −0.0012 (6) | 0.0021 (6) | −0.0016 (6) |
C3 | 0.0090 (7) | 0.0152 (8) | 0.0131 (8) | −0.0002 (7) | 0.0001 (6) | 0.0015 (7) |
O5B | 0.0212 (8) | 0.0196 (7) | 0.0255 (8) | −0.0081 (6) | 0.0042 (7) | −0.0037 (6) |
O5A | 0.0209 (8) | 0.0282 (8) | 0.0289 (10) | 0.0066 (6) | 0.0064 (7) | −0.0088 (6) |
N5 | 0.0179 (8) | 0.0152 (7) | 0.0159 (8) | 0.0005 (7) | 0.0028 (7) | 0.0006 (6) |
C5 | 0.0125 (8) | 0.0123 (8) | 0.0145 (9) | 0.0007 (6) | 0.0025 (7) | −0.0005 (6) |
N2—N1 | 1.369 (2) | N4—C3 | 1.377 (2) |
N2—C3 | 1.372 (2) | O5B—N5 | 1.222 (2) |
O3—C3 | 1.231 (2) | O5A—N5 | 1.228 (2) |
N1—C5 | 1.291 (2) | N5—C5 | 1.447 (3) |
N4—C5 | 1.353 (2) | ||
N1—N2—C3 | 112.9 (2) | O5B—N5—O5A | 126.2 (2) |
C5—N1—N2 | 102.34 (15) | O5B—N5—C5 | 116.7 (2) |
C5—N4—C3 | 106.0 (2) | O5A—N5—C5 | 117.1 (2) |
O3—C3—N2 | 126.9 (2) | N1—C5—N4 | 115.1 (2) |
O3—C3—N4 | 129.5 (2) | N1—C5—N5 | 122.0 (2) |
N2—C3—N4 | 103.6 (2) | N4—C5—N5 | 122.9 (2) |
C2H2N4O3 | F(000) = 264 |
Mr = 130.08 | Dx = 1.901 Mg m−3 |
Monoclinic, P21/c | Ag Kα radiation, λ = 0.56086 Å |
a = 9.3220 (4) Å | Cell parameters from 1193 reflections |
b = 5.4791 (2) Å | θ = 1.8–31.1° |
c = 9.0685 (3) Å | µ = 0.10 mm−1 |
β = 101.182 (1)° | T = 200 K |
V = 454.39 (3) Å3 | Plate-like, colorless |
Z = 4 | 0.24 × 0.08 × 0.02 mm |
Bruker platform diffractometer | 758 independent reflections |
Radiation source: fine-focus sealed tube | 757 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω–scan | θmax = 31.1°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→13 |
Tmin = 0.806, Tmax = 1.000 | k = −10→7 |
2264 measured reflections | l = −14→14 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | Calculated w = 1/[σ2(Fo2) + (0.0611P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = −0.033 |
758 reflections | Δρmax = 0.40 e Å−3 |
90 parameters | Δρmin = −0.25 e Å−3 |
0 restraints |
C2H2N4O3 | V = 454.39 (3) Å3 |
Mr = 130.08 | Z = 4 |
Monoclinic, P21/c | Ag Kα radiation, λ = 0.56086 Å |
a = 9.3220 (4) Å | µ = 0.10 mm−1 |
b = 5.4791 (2) Å | T = 200 K |
c = 9.0685 (3) Å | 0.24 × 0.08 × 0.02 mm |
β = 101.182 (1)° |
Bruker platform diffractometer | 758 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 757 reflections with I > 2σ(I) |
Tmin = 0.806, Tmax = 1.000 | Rint = 0.029 |
2264 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 90 parameters |
wR(F2) = 0.091 | 0 restraints |
S = 1.09 | Δρmax = 0.40 e Å−3 |
758 reflections | Δρmin = −0.25 e Å−3 |
Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS |
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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. |
x | y | z | Uiso*/Ueq | ||
N2 | 0.6540 (2) | 0.7379 (3) | 0.2356 (2) | 0.0191 (4) | |
H2 | 0.582 (4) | 0.645 (6) | 0.199 (4) | 0.044 (9)* | |
O3 | 0.8629 (2) | 0.5915 (3) | 0.1605 (2) | 0.0229 (4) | |
N1 | 0.6157 (2) | 0.9281 (3) | 0.3179 (2) | 0.0198 (4) | |
N4 | 0.8522 (2) | 0.9453 (3) | 0.3059 (2) | 0.0163 (4) | |
H4 | 0.945 (4) | 0.996 (6) | 0.319 (4) | 0.046 (9)* | |
C3 | 0.7985 (2) | 0.7417 (4) | 0.2251 (2) | 0.0167 (4) | |
O5B | 0.8701 (2) | 1.3592 (3) | 0.4764 (2) | 0.0292 (4) | |
O5A | 0.6416 (2) | 1.3237 (3) | 0.4967 (2) | 0.0340 (5) | |
N5 | 0.7510 (2) | 1.2590 (4) | 0.4503 (2) | 0.0211 (4) | |
C5 | 0.7380 (2) | 1.0430 (4) | 0.3573 (3) | 0.0163 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.0117 (8) | 0.0179 (8) | 0.0277 (10) | −0.0014 (7) | 0.0036 (7) | −0.0045 (8) |
O3 | 0.0168 (8) | 0.0254 (8) | 0.0263 (9) | 0.0037 (6) | 0.0039 (7) | −0.0061 (7) |
N1 | 0.0156 (9) | 0.0193 (8) | 0.0246 (10) | 0.0023 (7) | 0.0041 (8) | −0.0007 (7) |
N4 | 0.0120 (8) | 0.0180 (8) | 0.0190 (9) | −0.0015 (7) | 0.0035 (7) | −0.0016 (7) |
C3 | 0.0134 (8) | 0.0182 (9) | 0.0181 (10) | −0.0003 (8) | 0.0021 (7) | 0.0022 (8) |
O5B | 0.0297 (10) | 0.0264 (8) | 0.0321 (10) | −0.0111 (7) | 0.0070 (8) | −0.0054 (7) |
O5A | 0.0282 (10) | 0.0358 (10) | 0.0390 (12) | 0.0089 (8) | 0.0088 (9) | −0.0127 (8) |
N5 | 0.0245 (10) | 0.0192 (8) | 0.0196 (10) | 0.0010 (8) | 0.0045 (8) | 0.0010 (8) |
C5 | 0.0143 (9) | 0.0171 (9) | 0.0181 (10) | 0.0005 (7) | 0.0042 (8) | 0.0017 (8) |
N2—C3 | 1.368 (3) | N4—C3 | 1.375 (3) |
N2—N1 | 1.369 (3) | O5B—N5 | 1.220 (2) |
O3—C3 | 1.232 (3) | O5A—N5 | 1.228 (2) |
N1—C5 | 1.291 (3) | N5—C5 | 1.445 (3) |
N4—C5 | 1.353 (3) | ||
C3—N2—N1 | 113.0 (2) | O5B—N5—O5A | 126.1 (2) |
C5—N1—N2 | 102.2 (2) | O5B—N5—C5 | 116.9 (2) |
C5—N4—C3 | 105.9 (2) | O5A—N5—C5 | 117.1 (2) |
O3—C3—N2 | 126.9 (2) | N1—C5—N4 | 115.1 (2) |
O3—C3—N4 | 129.4 (2) | N1—C5—N5 | 122.0 (2) |
N2—C3—N4 | 103.7 (2) | N4—C5—N5 | 122.9 (2) |
C2H2N4O3 | F(000) = 264 |
Mr = 130.08 | Dx = 1.889 Mg m−3 |
Monoclinic, P21/c | Ag Kα radiation, λ = 0.56086 Å |
a = 9.3233 (4) Å | Cell parameters from 1204 reflections |
b = 5.4977 (2) Å | θ = 1.8–30.7° |
c = 9.0885 (3) Å | µ = 0.10 mm−1 |
β = 101.019 (1)° | T = 250 K |
V = 457.26 (3) Å3 | Plate-like, colorless |
Z = 4 | 0.24 × 0.08 × 0.02 mm |
Radiation source: fine-focus sealed tube | 656 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 30.7°, θmin = 1.8° |
Tmin = 0.839, Tmax = 1.000 | h = −15→12 |
2007 measured reflections | k = −8→7 |
657 independent reflections | l = −12→14 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | Calculated w = 1/[σ2(Fo2) + (0.0649P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = −0.025 |
657 reflections | Δρmax = 0.34 e Å−3 |
90 parameters | Δρmin = −0.21 e Å−3 |
0 restraints |
C2H2N4O3 | V = 457.26 (3) Å3 |
Mr = 130.08 | Z = 4 |
Monoclinic, P21/c | Ag Kα radiation, λ = 0.56086 Å |
a = 9.3233 (4) Å | µ = 0.10 mm−1 |
b = 5.4977 (2) Å | T = 250 K |
c = 9.0885 (3) Å | 0.24 × 0.08 × 0.02 mm |
β = 101.019 (1)° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 657 independent reflections |
Tmin = 0.839, Tmax = 1.000 | 656 reflections with I > 2σ(I) |
2007 measured reflections | Rint = 0.031 |
R[F2 > 2σ(F2)] = 0.036 | 90 parameters |
wR(F2) = 0.090 | 0 restraints |
S = 1.06 | Δρmax = 0.34 e Å−3 |
657 reflections | Δρmin = −0.21 e Å−3 |
Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS |
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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. |
x | y | z | Uiso*/Ueq | ||
N2 | 0.6541 (2) | 0.7397 (4) | 0.2353 (3) | 0.0246 (5) | |
H2 | 0.584 (4) | 0.647 (6) | 0.201 (4) | 0.043 (9)* | |
O3 | 0.8626 (2) | 0.5925 (3) | 0.1607 (2) | 0.0285 (4) | |
N1 | 0.6159 (2) | 0.9300 (3) | 0.3175 (2) | 0.0237 (4) | |
N4 | 0.8523 (2) | 0.9446 (3) | 0.3061 (2) | 0.0204 (4) | |
H4 | 0.943 (3) | 0.996 (6) | 0.317 (4) | 0.037 (8)* | |
C3 | 0.7985 (3) | 0.7421 (4) | 0.2252 (3) | 0.0200 (4) | |
O5B | 0.8706 (2) | 1.3569 (3) | 0.4763 (2) | 0.0372 (5) | |
O5A | 0.6421 (2) | 1.3235 (4) | 0.4960 (3) | 0.0436 (6) | |
N5 | 0.7511 (2) | 1.2584 (4) | 0.4498 (2) | 0.0263 (5) | |
C5 | 0.7385 (2) | 1.0434 (4) | 0.3570 (3) | 0.0202 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.0142 (9) | 0.0228 (10) | 0.0363 (13) | −0.0018 (8) | 0.0038 (9) | −0.0052 (9) |
O3 | 0.0191 (9) | 0.0319 (9) | 0.0335 (10) | 0.0040 (7) | 0.0028 (8) | −0.0082 (8) |
N1 | 0.0164 (10) | 0.0251 (10) | 0.0291 (12) | 0.0030 (8) | 0.0036 (9) | −0.0010 (9) |
N4 | 0.0143 (9) | 0.0212 (10) | 0.0256 (12) | −0.0024 (8) | 0.0037 (8) | −0.0015 (8) |
C3 | 0.0148 (10) | 0.0211 (10) | 0.0231 (11) | 0.0002 (9) | 0.0011 (8) | 0.0037 (10) |
O5B | 0.0364 (12) | 0.0324 (10) | 0.0429 (12) | −0.0131 (8) | 0.0078 (10) | −0.0064 (9) |
O5A | 0.0351 (12) | 0.0460 (12) | 0.0507 (15) | 0.0101 (9) | 0.0107 (11) | −0.0168 (10) |
N5 | 0.0307 (12) | 0.0235 (10) | 0.0246 (11) | 0.0007 (10) | 0.0047 (9) | −0.0006 (9) |
C5 | 0.0185 (11) | 0.0194 (11) | 0.0227 (12) | 0.0008 (8) | 0.0042 (9) | 0.0021 (9) |
N2—C3 | 1.367 (3) | N4—C3 | 1.375 (3) |
N2—N1 | 1.371 (3) | O5B—N5 | 1.221 (3) |
O3—C3 | 1.229 (3) | O5A—N5 | 1.225 (3) |
N1—C5 | 1.291 (3) | N5—C5 | 1.444 (3) |
N4—C5 | 1.350 (3) | ||
C3—N2—N1 | 113.0 (2) | O5B—N5—O5A | 126.1 (2) |
C5—N1—N2 | 102.2 (2) | O5B—N5—C5 | 116.6 (2) |
C5—N4—C3 | 106.2 (2) | O5A—N5—C5 | 117.3 (2) |
O3—C3—N2 | 126.9 (2) | N1—C5—N4 | 115.0 (2) |
O3—C3—N4 | 129.5 (2) | N1—C5—N5 | 121.8 (2) |
N2—C3—N4 | 103.6 (2) | N4—C5—N5 | 123.2 (2) |
C2H2N4O3 | F(000) = 264 |
Mr = 130.08 | Dx = 1.876 Mg m−3 |
Monoclinic, P21/c | Ag Kα radiation, λ = 0.56086 Å |
a = 9.3207 (4) Å | Cell parameters from 165 reflections |
b = 5.5215 (2) Å | θ = 1.8–28.3° |
c = 9.1102 (3) Å | µ = 0.10 mm−1 |
β = 100.870 (1)° | T = 298 K |
V = 460.44 (3) Å3 | Plate-like, colorless |
Z = 4 | 0.24 × 0.08 × 0.02 mm |
Bruker Platform diffractometer | 578 independent reflections |
Radiation source: fine-focus sealed tube | 578 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
ω–scan | θmax = 28.3°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→9 |
Tmin = 0.560, Tmax = 1.000 | k = −8→7 |
1691 measured reflections | l = −12→12 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | Calculated w = 1/[σ2(Fo2) + (0.0767P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.002 |
578 reflections | Δρmax = 0.35 e Å−3 |
90 parameters | Δρmin = −0.27 e Å−3 |
0 restraints |
C2H2N4O3 | V = 460.44 (3) Å3 |
Mr = 130.08 | Z = 4 |
Monoclinic, P21/c | Ag Kα radiation, λ = 0.56086 Å |
a = 9.3207 (4) Å | µ = 0.10 mm−1 |
b = 5.5215 (2) Å | T = 298 K |
c = 9.1102 (3) Å | 0.24 × 0.08 × 0.02 mm |
β = 100.870 (1)° |
Bruker Platform diffractometer | 578 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 578 reflections with I > 2σ(I) |
Tmin = 0.560, Tmax = 1.000 | Rint = 0.050 |
1691 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 90 parameters |
wR(F2) = 0.108 | 0 restraints |
S = 1.11 | Δρmax = 0.35 e Å−3 |
578 reflections | Δρmin = −0.27 e Å−3 |
Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS |
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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. |
x | y | z | Uiso*/Ueq | ||
N2 | 0.6540 (3) | 0.7414 (6) | 0.2357 (3) | 0.0301 (7) | |
H2 | 0.586 (4) | 0.641 (7) | 0.201 (4) | 0.037 (10)* | |
O3 | 0.8626 (2) | 0.5938 (4) | 0.1612 (2) | 0.0334 (6) | |
N1 | 0.6163 (2) | 0.9308 (5) | 0.3172 (3) | 0.0278 (6) | |
N4 | 0.8523 (3) | 0.9441 (5) | 0.3060 (3) | 0.0240 (6) | |
H4 | 0.940 (4) | 0.990 (8) | 0.316 (4) | 0.044 (11)* | |
C3 | 0.7986 (3) | 0.7430 (7) | 0.2253 (3) | 0.0262 (7) | |
O5B | 0.8705 (3) | 1.3544 (5) | 0.4762 (3) | 0.0442 (7) | |
O5A | 0.6424 (3) | 1.3238 (6) | 0.4944 (3) | 0.0528 (9) | |
N5 | 0.7519 (3) | 1.2566 (6) | 0.4496 (3) | 0.0318 (7) | |
C5 | 0.7385 (3) | 1.0437 (6) | 0.3568 (3) | 0.0240 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.0187 (11) | 0.031 (2) | 0.0399 (15) | −0.0029 (13) | 0.0040 (10) | −0.0060 (15) |
O3 | 0.0236 (10) | 0.039 (2) | 0.0363 (12) | 0.0065 (10) | 0.0028 (9) | −0.0095 (11) |
N1 | 0.0239 (13) | 0.025 (2) | 0.0349 (15) | 0.0036 (11) | 0.0059 (11) | −0.0004 (13) |
N4 | 0.0171 (11) | 0.025 (2) | 0.0294 (14) | −0.0038 (11) | 0.0027 (10) | −0.0020 (12) |
C3 | 0.0178 (11) | 0.035 (2) | 0.0248 (14) | −0.0019 (15) | 0.0009 (10) | 0.0057 (15) |
O5B | 0.0472 (15) | 0.039 (2) | 0.047 (2) | −0.0164 (13) | 0.0095 (11) | −0.0089 (13) |
O5A | 0.0436 (14) | 0.060 (2) | 0.056 (2) | 0.0145 (13) | 0.0104 (12) | −0.0222 (14) |
N5 | 0.0374 (14) | 0.028 (2) | 0.0287 (14) | 0.0016 (14) | 0.0037 (11) | −0.0006 (14) |
C5 | 0.0241 (13) | 0.023 (2) | 0.0241 (13) | 0.0001 (12) | 0.0029 (10) | −0.0005 (14) |
N2—N1 | 1.366 (4) | N4—C3 | 1.373 (4) |
N2—C3 | 1.369 (4) | O5B—N5 | 1.212 (3) |
O3—C3 | 1.228 (4) | O5A—N5 | 1.226 (3) |
N1—C5 | 1.290 (4) | N5—C5 | 1.440 (4) |
N4—C5 | 1.352 (4) | ||
N1—N2—C3 | 113.0 (3) | O5B—N5—O5A | 125.7 (3) |
C5—N1—N2 | 102.6 (2) | O5B—N5—C5 | 117.1 (3) |
C5—N4—C3 | 106.4 (2) | O5A—N5—C5 | 117.2 (3) |
O3—C3—N2 | 127.0 (3) | N1—C5—N4 | 114.6 (3) |
O3—C3—N4 | 129.5 (3) | N1—C5—N5 | 122.2 (3) |
N2—C3—N4 | 103.5 (3) | N4—C5—N5 | 123.1 (2) |
Experimental details
(100) | (150) | (200) | (250) | |
Crystal data | ||||
Chemical formula | C2H2N4O3 | C2H2N4O3 | C2H2N4O3 | C2H2N4O3 |
Mr | 130.08 | 130.08 | 130.08 | 130.08 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 100 | 150 | 200 | 250 |
a, b, c (Å) | 9.3129 (4), 5.4458 (2), 9.0261 (3) | 9.3185 (4), 5.4615 (2), 9.0475 (3) | 9.3220 (4), 5.4791 (2), 9.0685 (3) | 9.3233 (4), 5.4977 (2), 9.0885 (3) |
β (°) | 101.464 (1) | 101.332 (1) | 101.182 (1) | 101.019 (1) |
V (Å3) | 448.64 (3) | 451.48 (3) | 454.39 (3) | 457.26 (3) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Ag Kα, λ = 0.56086 Å | Ag Kα, λ = 0.56086 Å | Ag Kα, λ = 0.56086 Å | Ag Kα, λ = 0.56086 Å |
µ (mm−1) | 0.11 | 0.10 | 0.10 | 0.10 |
Crystal size (mm) | 0.24 × 0.08 × 0.02 | 0.24 × 0.08 × 0.02 | 0.24 × 0.08 × 0.02 | 0.24 × 0.08 × 0.02 |
Data collection | ||||
Diffractometer | Bruker platform diffractometer | Bruker platform diffractometer | Bruker platform diffractometer | ? |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.919, 1.000 | 0.912, 1.000 | 0.806, 1.000 | 0.839, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2922, 1036, 1036 | 2578, 894, 894 | 2264, 758, 757 | 2007, 657, 656 |
Rint | 0.034 | 0.030 | 0.029 | 0.031 |
(sin θ/λ)max (Å−1) | 1.036 | 0.982 | 0.921 | 0.909 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.093, 1.10 | 0.039, 0.092, 1.08 | 0.037, 0.091, 1.09 | 0.036, 0.090, 1.06 |
No. of reflections | 1036 | 894 | 758 | 657 |
No. of parameters | 90 | 90 | 90 | 90 |
Δρmax, Δρmin (e Å−3) | 0.56, −0.28 | 0.53, −0.24 | 0.40, −0.25 | 0.34, −0.21 |
(298) | |
Crystal data | |
Chemical formula | C2H2N4O3 |
Mr | 130.08 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 9.3207 (4), 5.5215 (2), 9.1102 (3) |
β (°) | 100.870 (1) |
V (Å3) | 460.44 (3) |
Z | 4 |
Radiation type | Ag Kα, λ = 0.56086 Å |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.24 × 0.08 × 0.02 |
Data collection | |
Diffractometer | Bruker Platform diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.560, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1691, 578, 578 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.844 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.108, 1.11 |
No. of reflections | 578 |
No. of parameters | 90 |
Δρmax, Δρmin (e Å−3) | 0.35, −0.27 |
Computer programs: Bruker SMART, Bruker SAINT, Bruker SHELXTL.