Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768103010231/av0064sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768103010231/av0064Isup2.hkl | |
Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768103010231/av0064IIsup3.rtv |
CCDC references: 219303; 219304
Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
C9H15N5O2 | Dx = 1.270 Mg m−3 |
Mr = 225.26 | Melting point = 142–144 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.844 (1) Å | Cell parameters from 25 reflections |
b = 16.436 (1) Å | θ = 12–16° |
c = 8.926 (1) Å | µ = 0.09 mm−1 |
β = 114.81 (2)° | T = 313 K |
V = 1177.7 (2) Å3 | Cubic, colourless |
Z = 4 | 0.10 × 0.10 × 0.10 mm |
F(000) = 480 |
CAD4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 26.0°, θmin = 2.5° |
Graphite monochromator | h = −10→9 |
ω scans | k = 0→20 |
2298 measured reflections | l = 0→10 |
2298 independent reflections | 2 standard reflections every 60 min |
1343 reflections with I > 2σ(I) | intensity decay: 1% |
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)] = 0.054 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.150 | All H-atom parameters refined |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0715P)2 + 0.1131P] where P = (Fo2 + 2Fc2)/3 |
2298 reflections | (Δ/σ)max = 0.022 |
206 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C9H15N5O2 | V = 1177.7 (2) Å3 |
Mr = 225.26 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.844 (1) Å | µ = 0.09 mm−1 |
b = 16.436 (1) Å | T = 313 K |
c = 8.926 (1) Å | 0.10 × 0.10 × 0.10 mm |
β = 114.81 (2)° |
CAD4 diffractometer | Rint = 0.000 |
2298 measured reflections | 2 standard reflections every 60 min |
2298 independent reflections | intensity decay: 1% |
1343 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.150 | All H-atom parameters refined |
S = 0.99 | Δρmax = 0.16 e Å−3 |
2298 reflections | Δρmin = −0.16 e Å−3 |
206 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.1792 (2) | 0.16347 (14) | 0.5037 (2) | 0.0681 (7) | |
O2 | −0.0277 (2) | 0.11884 (15) | 0.3822 (2) | 0.0719 (7) | |
N1 | 0.1858 (2) | 0.12887 (14) | 0.9515 (3) | 0.0478 (6) | |
N2 | −0.0509 (3) | 0.12912 (15) | 0.5091 (3) | 0.0514 (6) | |
N3 | −0.0870 (2) | 0.08831 (14) | 0.8245 (3) | 0.0488 (6) | |
N4 | 0.4494 (2) | 0.17705 (13) | 1.0663 (3) | 0.0485 (6) | |
N5 | 0.3571 (3) | 0.07410 (17) | 0.6699 (3) | 0.0697 (8) | |
C1 | 0.0528 (3) | 0.10993 (16) | 0.8120 (3) | 0.0421 (6) | |
C2 | 0.0697 (3) | 0.10408 (16) | 0.6588 (3) | 0.0433 (6) | |
C3 | 0.2946 (3) | 0.18506 (16) | 0.9553 (3) | 0.0430 (6) | |
C4 | 0.2484 (5) | 0.2597 (2) | 0.8497 (4) | 0.0596 (8) | |
C5 | 0.2263 (3) | 0.08616 (16) | 0.6618 (3) | 0.0475 (7) | |
C6 | 0.5042 (5) | 0.1018 (2) | 1.1601 (5) | 0.0672 (10) | |
C7 | 0.5768 (4) | 0.2398 (2) | 1.0974 (5) | 0.0679 (9) | |
C8 | −0.1105 (5) | 0.1087 (3) | 0.9728 (5) | 0.0690 (10) | |
C9 | −0.2153 (4) | 0.0377 (2) | 0.7027 (5) | 0.0630 (9) | |
H4 | 0.272 (5) | 0.308 (3) | 0.923 (5) | 0.118 (14)* | |
H41 | 0.136 (5) | 0.260 (2) | 0.782 (5) | 0.093 (12)* | |
H42 | 0.309 (5) | 0.258 (2) | 0.781 (5) | 0.102 (13)* | |
H6 | 0.469 (5) | 0.101 (3) | 1.253 (6) | 0.128 (16)* | |
H61 | 0.616 (5) | 0.097 (2) | 1.213 (5) | 0.118 (15)* | |
H62 | 0.441 (5) | 0.059 (3) | 1.104 (5) | 0.116 (15)* | |
H7 | 0.598 (4) | 0.250 (2) | 0.998 (5) | 0.104 (13)* | |
H71 | 0.671 (5) | 0.226 (2) | 1.185 (5) | 0.107 (14)* | |
H72 | 0.538 (5) | 0.295 (3) | 1.122 (5) | 0.141 (17)* | |
H8 | −0.042 (7) | 0.153 (3) | 1.033 (7) | 0.17 (2)* | |
H81 | −0.081 (6) | 0.070 (3) | 1.042 (6) | 0.16 (2)* | |
H82 | −0.220 (7) | 0.115 (3) | 0.942 (6) | 0.15 (2)* | |
H9 | −0.173 (4) | 0.010 (2) | 0.629 (4) | 0.081 (10)* | |
H91 | −0.239 (4) | −0.005 (2) | 0.768 (4) | 0.100 (13)* | |
H92 | −0.308 (5) | 0.068 (2) | 0.633 (5) | 0.103 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0453 (11) | 0.0925 (17) | 0.0588 (13) | 0.0210 (11) | 0.0141 (10) | 0.0061 (11) |
O2 | 0.0649 (13) | 0.1105 (19) | 0.0402 (11) | 0.0029 (12) | 0.0219 (10) | −0.0009 (11) |
N1 | 0.0423 (12) | 0.0592 (15) | 0.0407 (12) | −0.0060 (10) | 0.0161 (10) | 0.0010 (10) |
N2 | 0.0422 (13) | 0.0637 (16) | 0.0439 (13) | 0.0020 (11) | 0.0139 (11) | −0.0017 (11) |
N3 | 0.0401 (11) | 0.0596 (15) | 0.0498 (13) | −0.0052 (10) | 0.0218 (10) | −0.0056 (11) |
N4 | 0.0413 (12) | 0.0518 (14) | 0.0475 (13) | −0.0075 (10) | 0.0139 (10) | −0.0002 (11) |
N5 | 0.0524 (15) | 0.086 (2) | 0.0782 (19) | 0.0140 (14) | 0.0345 (14) | 0.0050 (14) |
C1 | 0.0361 (13) | 0.0450 (15) | 0.0421 (14) | 0.0039 (11) | 0.0135 (11) | 0.0026 (12) |
C2 | 0.0338 (12) | 0.0524 (16) | 0.0394 (14) | 0.0020 (11) | 0.0110 (11) | −0.0022 (12) |
C3 | 0.0429 (14) | 0.0525 (17) | 0.0356 (13) | −0.0016 (12) | 0.0183 (11) | −0.0032 (12) |
C4 | 0.066 (2) | 0.0498 (19) | 0.0568 (19) | 0.0018 (16) | 0.0196 (18) | 0.0004 (15) |
C5 | 0.0481 (15) | 0.0509 (17) | 0.0434 (15) | 0.0034 (13) | 0.0190 (12) | 0.0018 (12) |
C6 | 0.0489 (19) | 0.070 (2) | 0.065 (2) | −0.0056 (18) | 0.0065 (17) | 0.0147 (19) |
C7 | 0.0497 (19) | 0.071 (3) | 0.074 (2) | −0.0202 (17) | 0.0172 (18) | −0.003 (2) |
C8 | 0.064 (2) | 0.095 (3) | 0.062 (2) | −0.004 (2) | 0.0408 (19) | −0.006 (2) |
C9 | 0.0451 (17) | 0.070 (2) | 0.068 (2) | −0.0108 (16) | 0.0182 (16) | −0.0101 (19) |
O1—N2 | 1.250 (3) | C4—H4 | 0.99 (4) |
O2—N2 | 1.245 (3) | C4—H41 | 0.92 (4) |
N1—C3 | 1.324 (3) | C4—H42 | 0.97 (4) |
N1—C1 | 1.342 (3) | C6—H6 | 1.00 (5) |
N2—C2 | 1.377 (3) | C6—H61 | 0.90 (4) |
N3—C1 | 1.335 (3) | C6—H62 | 0.90 (4) |
N3—C9 | 1.458 (4) | C7—H7 | 0.99 (4) |
N3—C8 | 1.462 (4) | C7—H71 | 0.90 (4) |
N4—C3 | 1.317 (3) | C7—H72 | 1.03 (5) |
N4—C6 | 1.458 (4) | C8—H8 | 0.96 (6) |
N4—C7 | 1.466 (4) | C8—H81 | 0.85 (5) |
N5—C5 | 1.146 (3) | C8—H82 | 0.89 (5) |
C1—C2 | 1.441 (3) | C9—H9 | 1.00 (3) |
C2—C5 | 1.405 (3) | C9—H91 | 0.99 (4) |
C3—C4 | 1.496 (4) | C9—H92 | 0.93 (4) |
C3—N1—C1 | 122.1 (2) | N5—C5—C2 | 176.9 (3) |
O2—N2—O1 | 121.3 (2) | N4—C6—H6 | 110 (3) |
O2—N2—C2 | 119.1 (2) | N4—C6—H61 | 114 (3) |
O1—N2—C2 | 119.6 (2) | H6—C6—H61 | 102 (3) |
C1—N3—C9 | 123.2 (2) | N4—C6—H62 | 111 (3) |
C1—N3—C8 | 120.2 (2) | H6—C6—H62 | 97 (3) |
C9—N3—C8 | 116.3 (3) | H61—C6—H62 | 120 (4) |
C3—N4—C6 | 120.5 (2) | N4—C7—H7 | 111 (2) |
C3—N4—C7 | 123.1 (3) | N4—C7—H71 | 110 (3) |
C6—N4—C7 | 116.3 (3) | H7—C7—H71 | 111 (3) |
N3—C1—N1 | 117.8 (2) | N4—C7—H72 | 111 (3) |
N3—C1—C2 | 122.0 (2) | H7—C7—H72 | 105 (3) |
N1—C1—C2 | 119.7 (2) | H71—C7—H72 | 108 (4) |
N2—C2—C5 | 115.9 (2) | N3—C8—H8 | 112 (3) |
N2—C2—C1 | 123.7 (2) | N3—C8—H81 | 112 (4) |
C5—C2—C1 | 119.4 (2) | H8—C8—H81 | 103 (5) |
N4—C3—N1 | 117.7 (2) | N3—C8—H82 | 107 (3) |
N4—C3—C4 | 118.6 (3) | H8—C8—H82 | 116 (4) |
N1—C3—C4 | 123.5 (2) | H81—C8—H82 | 106 (4) |
C3—C4—H4 | 108 (2) | N3—C9—H9 | 111.3 (17) |
C3—C4—H41 | 110 (2) | N3—C9—H91 | 105.1 (19) |
H4—C4—H41 | 107 (3) | H9—C9—H91 | 107 (3) |
C3—C4—H42 | 107 (2) | N3—C9—H92 | 113 (2) |
H4—C4—H42 | 115 (3) | H9—C9—H92 | 106 (3) |
H41—C4—H42 | 109 (3) | H91—C9—H92 | 115 (3) |
C9—N3—C1—N1 | −155.5 (3) | N3—C1—C2—N2 | 44.7 (4) |
C8—N3—C1—N1 | 18.5 (4) | N1—C1—C2—N2 | −142.9 (3) |
C9—N3—C1—C2 | 17.0 (4) | N3—C1—C2—C5 | −147.4 (3) |
C8—N3—C1—C2 | −169.0 (3) | N1—C1—C2—C5 | 25.0 (4) |
C3—N1—C1—N3 | −146.4 (2) | C6—N4—C3—N1 | 10.9 (4) |
C3—N1—C1—C2 | 40.9 (4) | C7—N4—C3—N1 | −172.2 (3) |
O2—N2—C2—C5 | 14.4 (4) | C6—N4—C3—C4 | −173.7 (3) |
O1—N2—C2—C5 | −163.8 (2) | C7—N4—C3—C4 | 3.3 (4) |
O2—N2—C2—C1 | −177.3 (3) | C1—N1—C3—N4 | −151.2 (2) |
O1—N2—C2—C1 | 4.5 (4) | C1—N1—C3—C4 | 33.6 (4) |
Experimental details
Crystal data | |
Chemical formula | C9H15N5O2 |
Mr | 225.26 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 313 |
a, b, c (Å) | 8.844 (1), 16.436 (1), 8.926 (1) |
β (°) | 114.81 (2) |
V (Å3) | 1177.7 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.10 × 0.10 × 0.10 |
Data collection | |
Diffractometer | CAD4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2298, 2298, 1343 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.150, 0.99 |
No. of reflections | 2298 |
No. of parameters | 206 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.16, −0.16 |
Computer programs: SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997).
O1—N2 | 1.250 (3) | N4—C3 | 1.317 (3) |
O2—N2 | 1.245 (3) | N4—C6 | 1.458 (4) |
N1—C3 | 1.324 (3) | N4—C7 | 1.466 (4) |
N1—C1 | 1.342 (3) | N5—C5 | 1.146 (3) |
N2—C2 | 1.377 (3) | C1—C2 | 1.441 (3) |
N3—C1 | 1.335 (3) | C2—C5 | 1.405 (3) |
N3—C9 | 1.458 (4) | C3—C4 | 1.496 (4) |
N3—C8 | 1.462 (4) | ||
C3—N1—C1 | 122.1 (2) | N3—C1—N1 | 117.8 (2) |
O2—N2—O1 | 121.3 (2) | N3—C1—C2 | 122.0 (2) |
O2—N2—C2 | 119.1 (2) | N1—C1—C2 | 119.7 (2) |
O1—N2—C2 | 119.6 (2) | N2—C2—C5 | 115.9 (2) |
C1—N3—C9 | 123.2 (2) | N2—C2—C1 | 123.7 (2) |
C1—N3—C8 | 120.2 (2) | C5—C2—C1 | 119.4 (2) |
C9—N3—C8 | 116.3 (3) | N4—C3—N1 | 117.7 (2) |
C3—N4—C6 | 120.5 (2) | N4—C3—C4 | 118.6 (3) |
C3—N4—C7 | 123.1 (3) | N1—C3—C4 | 123.5 (2) |
C6—N4—C7 | 116.3 (3) | ||
C9—N3—C1—N1 | −155.5 (3) | N3—C1—C2—N2 | 44.7 (4) |
C8—N3—C1—N1 | 18.5 (4) | N1—C1—C2—N2 | −142.9 (3) |
C9—N3—C1—C2 | 17.0 (4) | N3—C1—C2—C5 | −147.4 (3) |
C8—N3—C1—C2 | −169.0 (3) | N1—C1—C2—C5 | 25.0 (4) |
C3—N1—C1—N3 | −146.4 (2) | C6—N4—C3—N1 | 10.9 (4) |
C3—N1—C1—C2 | 40.9 (4) | C7—N4—C3—N1 | −172.2 (3) |
O2—N2—C2—C5 | 14.4 (4) | C6—N4—C3—C4 | −173.7 (3) |
O1—N2—C2—C5 | −163.8 (2) | C7—N4—C3—C4 | 3.3 (4) |
O2—N2—C2—C1 | −177.3 (3) | C1—N1—C3—N4 | −151.2 (2) |
O1—N2—C2—C1 | 4.5 (4) | C1—N1—C3—C4 | 33.6 (4) |