Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618016923/yf3153sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618016923/yf3153Isup2.hkl |
CCDC reference: 1881877
Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b) and ShelXle (Hübschle et al., 2011); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).
C5H5N5O·H2O | F(000) = 704 |
Mr = 169.16 | Dx = 1.663 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.357 (13) Å | Cell parameters from 9591 reflections |
b = 3.712 (3) Å | θ = 2.6–26.3° |
c = 22.723 (19) Å | µ = 0.13 mm−1 |
β = 101.72 (3)° | T = 100 K |
V = 1350.9 (19) Å3 | Very thin needle, colourless |
Z = 8 | 0.40 × 0.10 × 0.10 mm |
Bruker D8 VENTURE diffractometer | 1086 reflections with I > 2σ(I) |
Multilayer mirror monochromator | Rint = 0.089 |
φ and ω scans | θmax = 26.4°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | h = −20→20 |
k = −4→4 | |
33557 measured reflections | l = −28→28 |
1397 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.166 | w = 1/[σ2(Fo2) + (0.0742P)2 + 4.2384P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max < 0.001 |
1397 reflections | Δρmax = 0.27 e Å−3 |
112 parameters | Δρmin = −0.56 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The structure was solved and refined using the Bruker SHELXTL software package (Bruker, 2014; Hübschle et al., 2011; Sheldrick, 2015b), in the space group C2/c, with Z = 8 for the formula unit, C5H7N5O2. The final anisotropic full-matrix least-squares refinement on F2 with 116 variables converged at R1 = 7.14%, for the observed data and wR2 = 19.41% for all data. The goodness-of-fit was 1.089. The largest peak in the final difference electron density was 0.269 e Å-3 and the largest hole was -0.562 e Å-3 with an r.m.s. deviation of 0.086 e Å-3. On the basis of the final model, the calculated density was 1.663 Mg m-3 and F(000) = 704 e. All H atoms bound to C atoms were positioned geometrically ( C—H = 0.93/1.00 Å) and allowed to ride with Uiso(H)= 1.2/1.5Ueq(C). |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O2 | 0.6958 (3) | 0.6401 (14) | 0.23204 (16) | 0.0541 (13) | 0.75 |
H2Y | 0.730670 | 0.854966 | 0.242044 | 0.081* | 0.75 |
H2X | 0.667110 | 0.607746 | 0.265584 | 0.081* | 0.75 |
O2' | 0.7846 (9) | 0.953 (4) | 0.2572 (6) | 0.0541 (13) | 0.25 |
H2W | 0.774086 | 1.213329 | 0.255700 | 0.081* | 0.25 |
H2Z | 0.752094 | 0.765008 | 0.232740 | 0.081* | 0.25 |
O1 | 0.61373 (11) | 0.3616 (5) | 0.51107 (8) | 0.0169 (5) | |
N1 | 0.64639 (13) | 0.5857 (6) | 0.34214 (9) | 0.0136 (5) | |
N2 | 0.77095 (14) | 0.8537 (6) | 0.38555 (10) | 0.0156 (6) | |
H2A | 0.780006 | 0.902557 | 0.349521 | 0.019* | |
H2B | 0.807740 | 0.918339 | 0.417693 | 0.019* | |
C9 | 0.57886 (16) | 0.4099 (7) | 0.35240 (11) | 0.0123 (6) | |
N8 | 0.51426 (13) | 0.2871 (6) | 0.31270 (10) | 0.0152 (5) | |
H8 | 0.506724 | 0.304919 | 0.273345 | 0.018* | 0.5 |
C7 | 0.46028 (17) | 0.1238 (8) | 0.34504 (12) | 0.0164 (6) | |
H7 | 0.408713 | 0.013066 | 0.327525 | 0.020* | |
C6 | 0.49153 (16) | 0.1454 (8) | 0.40446 (12) | 0.0156 (6) | |
H6 | 0.467115 | 0.056609 | 0.436123 | 0.019* | |
N3 | 0.69230 (13) | 0.6152 (6) | 0.44912 (9) | 0.0140 (5) | |
H3 | 0.730825 | 0.692018 | 0.479352 | 0.017* | 0.5 |
C4 | 0.62514 (16) | 0.4336 (7) | 0.46086 (12) | 0.0132 (6) | |
N5 | 0.56777 (13) | 0.3267 (6) | 0.40962 (9) | 0.0127 (5) | |
C2 | 0.70163 (16) | 0.6820 (7) | 0.39144 (11) | 0.0124 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.050 (2) | 0.087 (4) | 0.0280 (18) | 0.019 (2) | 0.0143 (17) | 0.0103 (19) |
O2' | 0.050 (2) | 0.087 (4) | 0.0280 (18) | 0.019 (2) | 0.0143 (17) | 0.0103 (19) |
O1 | 0.0200 (10) | 0.0225 (11) | 0.0088 (9) | −0.0018 (8) | 0.0047 (7) | 0.0009 (8) |
N1 | 0.0149 (11) | 0.0170 (12) | 0.0082 (11) | 0.0019 (9) | 0.0007 (9) | 0.0000 (9) |
N2 | 0.0163 (12) | 0.0230 (13) | 0.0076 (11) | −0.0035 (10) | 0.0025 (9) | 0.0007 (9) |
C9 | 0.0143 (13) | 0.0118 (13) | 0.0107 (13) | 0.0045 (10) | 0.0021 (10) | −0.0002 (10) |
N8 | 0.0129 (11) | 0.0185 (12) | 0.0135 (11) | 0.0021 (9) | 0.0006 (9) | −0.0022 (9) |
C7 | 0.0143 (13) | 0.0166 (14) | 0.0178 (14) | 0.0019 (11) | 0.0020 (11) | −0.0023 (11) |
C6 | 0.0148 (13) | 0.0163 (14) | 0.0170 (14) | 0.0008 (11) | 0.0063 (11) | −0.0001 (11) |
N3 | 0.0136 (11) | 0.0183 (12) | 0.0096 (11) | 0.0010 (9) | 0.0014 (9) | 0.0005 (9) |
C4 | 0.0146 (13) | 0.0137 (13) | 0.0108 (13) | 0.0046 (11) | 0.0015 (10) | −0.0019 (10) |
N5 | 0.0129 (11) | 0.0153 (12) | 0.0096 (11) | 0.0024 (9) | 0.0016 (9) | 0.0009 (9) |
C2 | 0.0144 (13) | 0.0126 (13) | 0.0104 (13) | 0.0046 (11) | 0.0029 (10) | 0.0012 (10) |
O2—H2Y | 0.9800 | C9—N5 | 1.384 (3) |
O2—H2X | 0.9802 | N8—C7 | 1.397 (4) |
O2'—H2W | 0.9800 | N8—H8 | 0.8800 |
O2'—H2Z | 0.9800 | C7—C6 | 1.345 (4) |
O1—C4 | 1.223 (3) | C7—H7 | 0.9500 |
N1—C2 | 1.337 (3) | C6—N5 | 1.401 (4) |
N1—C9 | 1.343 (4) | C6—H6 | 0.9500 |
N2—C2 | 1.331 (4) | N3—C4 | 1.361 (4) |
N2—H2A | 0.8800 | N3—C2 | 1.373 (3) |
N2—H2B | 0.8800 | N3—H3 | 0.8800 |
C9—N8 | 1.323 (4) | C4—N5 | 1.396 (3) |
H2Y—O2—H2X | 105.5 | C7—C6—N5 | 105.2 (2) |
H2W—O2'—H2Z | 127.7 | C7—C6—H6 | 127.4 |
C2—N1—C9 | 115.1 (2) | N5—C6—H6 | 127.4 |
C2—N2—H2A | 120.0 | C4—N3—C2 | 121.8 (2) |
C2—N2—H2B | 120.0 | C4—N3—H3 | 119.1 |
H2A—N2—H2B | 120.0 | C2—N3—H3 | 119.1 |
N8—C9—N1 | 128.3 (2) | O1—C4—N3 | 125.0 (2) |
N8—C9—N5 | 108.9 (2) | O1—C4—N5 | 120.8 (2) |
N1—C9—N5 | 122.7 (2) | N3—C4—N5 | 114.2 (2) |
C9—N8—C7 | 107.1 (2) | C9—N5—C4 | 121.7 (2) |
C9—N8—H8 | 126.5 | C9—N5—C6 | 108.2 (2) |
C7—N8—H8 | 126.5 | C4—N5—C6 | 130.0 (2) |
C6—C7—N8 | 110.5 (2) | N2—C2—N1 | 119.2 (2) |
C6—C7—H7 | 124.7 | N2—C2—N3 | 116.4 (2) |
N8—C7—H7 | 124.7 | N1—C2—N3 | 124.4 (2) |
C2—N1—C9—N8 | 179.2 (3) | N1—C9—N5—C6 | 179.9 (2) |
C2—N1—C9—N5 | −1.4 (4) | O1—C4—N5—C9 | 179.0 (2) |
N1—C9—N8—C7 | 179.9 (3) | N3—C4—N5—C9 | −1.5 (4) |
N5—C9—N8—C7 | 0.4 (3) | O1—C4—N5—C6 | 2.3 (4) |
C9—N8—C7—C6 | −0.1 (3) | N3—C4—N5—C6 | −178.2 (2) |
N8—C7—C6—N5 | −0.2 (3) | C7—C6—N5—C9 | 0.5 (3) |
C2—N3—C4—O1 | 179.0 (2) | C7—C6—N5—C4 | 177.5 (3) |
C2—N3—C4—N5 | −0.4 (4) | C9—N1—C2—N2 | 179.2 (2) |
N8—C9—N5—C4 | −177.9 (2) | C9—N1—C2—N3 | −0.6 (4) |
N1—C9—N5—C4 | 2.5 (4) | C4—N3—C2—N2 | −178.3 (2) |
N8—C9—N5—C6 | −0.6 (3) | C4—N3—C2—N1 | 1.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2Y···O2i | 0.98 | 1.62 | 2.582 (6) | 166 |
O2—H2X···N1 | 0.98 | 1.84 | 2.788 (5) | 162 |
O2′—H2W···O2′i | 0.98 | 1.30 | 2.164 (15) | 143 |
O2′—H2Z···O2′ii | 0.98 | 1.34 | 2.164 (15) | 137 |
N3—H3···N3iii | 0.88 | 1.98 | 2.853 (5) | 174 |
N2—H2A···O2i | 0.88 | 2.16 | 3.026 (5) | 168 |
N2—H2A···O2′ | 0.88 | 2.12 | 2.993 (12) | 170 |
N2—H2B···O1iii | 0.88 | 2.02 | 2.897 (3) | 172 |
N8—H8···N8iv | 0.88 | 1.92 | 2.792 (5) | 173 |
C7—H7···O2v | 0.95 | 2.39 | 3.315 (5) | 163 |
C6—H6···O1vi | 0.95 | 2.50 | 3.396 (4) | 158 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+3/2, −y+3/2, −z+1; (iv) −x+1, y, −z+1/2; (v) −x+1, y−1, −z+1/2; (vi) −x+1, −y, −z+1. |