Crystals of hypoxanthinium (6-oxo-1H,7H-purin-9-ium) nitrate hydrates were investigated by means of X-ray diffraction at different temperatures. The data for hypoxanthinium nitrate monohydrate (C5H5N4O+·NO3−·H2O, Hx1) were collected at 20, 105 and 285 K. The room-temperature phase was reported previously [Schmalle et al. (1990). Acta Cryst. C46, 340–342] and the low-temperature phase has not been investigated yet. The structure underwent a phase transition, which resulted in a change of space group from Pmnb to P21/n at lower temperature and subsequently in nonmerohedral twinning. The structure of hypoxanthinium dinitrate trihydrate (H3O+·C5H5N4O+·2NO3−·2H2O, Hx2) was determined at 20 and 100 K, and also has not been reported previously. The Hx2 structure consists of two types of layers: the `hypoxanthinium nitrate monohydrate' layers (HX) observed in Hx1 and layers of Zundel complex H3O+·H2O interacting with nitrate anions (OX). The crystal can be considered as a solid solution of two salts, i.e. hypoxanthinium nitrate monohydrate, C5H5N4O+·NO3−·H2O, and oxonium nitrate monohydrate, H3O+(H2O)·NO3−.
Supporting information
CCDC references: 1901717; 1901719; 1901718; 1901720; 1901716
Data collection: CrysAlis PRO (Rigaku OD, 2015) for hx1_20k, hx1_105k, hx2_100k; CrysAlis PRO 1.171.38.43c (Rigaku OD, 2015) for hx2_20k. Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for hx1_20k, hx1_105k, hx2_100k; CrysAlis PRO 1.171.38.43c (Rigaku OD, 2015) for hx2_20k. Data reduction: CrysAlis PRO (Rigaku OD, 2015) for hx1_20k, hx1_105k, hx2_100k; CrysAlis PRO 1.171.38.43c (Rigaku OD, 2015) for hx2_20k. For all structures, program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
6-Oxo-1
H,7
H-purin-9-ium nitrate monohydrate (hx1_20k)
top
Crystal data top
C5H5N4O+·NO3−·H2O | F(000) = 448 |
Mr = 217.16 | Dx = 1.720 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.1156 (18) Å | Cell parameters from 1835 reflections |
b = 13.754 (2) Å | θ = 2.9–27.5° |
c = 10.0367 (19) Å | µ = 0.15 mm−1 |
β = 96.52 (2)° | T = 20 K |
V = 838.8 (3) Å3 | Block, clear light colourless |
Z = 4 | 0.19 × 0.11 × 0.09 mm |
Data collection top
Agilent Technologies SuperNova four-circle diffractometer equipped with a
micro-focus sealed tube and an Eos CCD detector | 2207 reflections with I > 2σ(I) |
Detector resolution: 8.0013 pixels mm-1 | Rint = 0.252 |
ω scans | θmax = 28.3°, θmin = 2.5° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −8→8 |
Tmin = 0.646, Tmax = 1.000 | k = −17→17 |
9106 measured reflections | l = −13→12 |
3467 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.292 | w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3467 reflections | Δρmax = 0.76 e Å−3 |
157 parameters | Δρmin = −0.72 e Å−3 |
0 restraints | |
Special details top
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. Refined as a 2-component twin. All crystal structures were determined using an Agilent
Technologies SuperNova four-circle diffractometer equipped with a micro-focus
sealed tube and an Eos CCD detector. The temperature was controlled with an
Oxford Cryosystems low-temperature nitrogen gas-flow device. For helium
measurements, a CRYOCOOL-LHe gas stream cooler was used. Unit-cell
determination, data reduction, and absorption correction were performed using
CrysAlis PRO Version 1.171.38.46 (Agilent Technologies, 2014). All structures
were solved and refined using ShelXT (Sheldrick, 2015b) with intrinsic phasing
and refined with ShelXL (Sheldrick, 2015a) with least-squares within
OLEX2
graphical environment (Dolomanov et al., 2009). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O6 | 0.2467 (6) | 0.7924 (2) | 0.7755 (3) | 0.0121 (9) | |
N1 | 0.2466 (7) | 0.6260 (3) | 0.7530 (4) | 0.0099 (9) | |
H1 | 0.243461 | 0.619512 | 0.839971 | 0.012* | |
N3 | 0.2530 (7) | 0.5396 (3) | 0.5492 (4) | 0.0099 (9) | |
N7 | 0.2566 (7) | 0.7888 (3) | 0.4645 (4) | 0.0098 (9) | |
N9 | 0.2621 (7) | 0.6502 (3) | 0.3607 (4) | 0.0097 (9) | |
C2 | 0.2489 (8) | 0.5429 (4) | 0.6784 (5) | 0.0117 (11) | |
H2 | 0.247485 | 0.482661 | 0.724720 | 0.014* | |
C4 | 0.2563 (8) | 0.6294 (3) | 0.4937 (5) | 0.0095 (10) | |
C5 | 0.2529 (8) | 0.7169 (3) | 0.5597 (5) | 0.0107 (11) | |
C6 | 0.2488 (8) | 0.7207 (3) | 0.7015 (5) | 0.0081 (10) | |
C8 | 0.2626 (8) | 0.7470 (4) | 0.3453 (5) | 0.0104 (11) | |
N11 | 0.2564 (7) | 0.5331 (3) | 0.0680 (4) | 0.0100 (9) | |
O11 | 0.2573 (6) | 0.6237 (2) | 0.0541 (3) | 0.0133 (9) | |
O12 | 0.2451 (6) | 0.4791 (2) | −0.0342 (3) | 0.0126 (9) | |
O13 | 0.2668 (6) | 0.4961 (2) | 0.1831 (3) | 0.0114 (8) | |
O1 | 0.2437 (6) | 0.3444 (3) | 0.4349 (4) | 0.0122 (8) | |
H1A | 0.269 (11) | 0.412 (6) | 0.443 (6) | 0.04 (2)* | |
H8 | 0.261 (11) | 0.783 (5) | 0.261 (7) | 0.027 (17)* | |
H1B | 0.237 (9) | 0.320 (4) | 0.506 (6) | 0.007 (14)* | |
H7 | 0.263 (10) | 0.851 (5) | 0.484 (6) | 0.027 (17)* | |
H9 | 0.263 (11) | 0.605 (5) | 0.302 (7) | 0.026 (17)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O6 | 0.0139 (19) | 0.0088 (17) | 0.0130 (19) | 0.0020 (14) | −0.0012 (15) | −0.0019 (13) |
N1 | 0.013 (2) | 0.007 (2) | 0.0094 (18) | 0.0004 (16) | −0.0017 (16) | 0.0008 (16) |
N3 | 0.011 (2) | 0.0064 (18) | 0.012 (2) | −0.0001 (16) | 0.0000 (17) | −0.0004 (16) |
N7 | 0.010 (2) | 0.0055 (18) | 0.013 (2) | −0.0018 (16) | −0.0024 (17) | 0.0009 (15) |
N9 | 0.012 (2) | 0.0049 (19) | 0.012 (2) | −0.0003 (16) | −0.0032 (17) | −0.0006 (16) |
C2 | 0.009 (3) | 0.007 (2) | 0.018 (3) | 0.0002 (18) | −0.004 (2) | −0.0002 (19) |
C4 | 0.008 (3) | 0.010 (2) | 0.010 (2) | 0.0019 (19) | −0.003 (2) | −0.0022 (17) |
C5 | 0.009 (2) | 0.007 (2) | 0.015 (3) | 0.0009 (19) | −0.002 (2) | 0.0001 (18) |
C6 | 0.005 (2) | 0.010 (2) | 0.009 (2) | −0.0005 (17) | −0.0018 (19) | 0.0003 (17) |
C8 | 0.007 (3) | 0.010 (2) | 0.013 (2) | −0.0015 (18) | −0.0037 (19) | 0.0009 (19) |
N11 | 0.010 (2) | 0.0081 (19) | 0.011 (2) | −0.0003 (17) | −0.0027 (17) | −0.0014 (15) |
O11 | 0.021 (2) | 0.0043 (16) | 0.0146 (18) | −0.0005 (15) | 0.0004 (15) | 0.0024 (13) |
O12 | 0.019 (2) | 0.0091 (16) | 0.0093 (18) | −0.0024 (16) | −0.0014 (16) | −0.0021 (13) |
O13 | 0.0194 (19) | 0.0092 (17) | 0.0056 (18) | 0.0016 (14) | 0.0009 (14) | 0.0020 (13) |
O1 | 0.016 (2) | 0.0094 (18) | 0.0106 (18) | −0.0009 (15) | −0.0013 (15) | 0.0024 (14) |
Geometric parameters (Å, º) top
O6—C6 | 1.235 (6) | N9—H9 | 0.85 (7) |
N1—H1 | 0.8800 | C2—H2 | 0.9500 |
N1—C2 | 1.367 (6) | C4—C5 | 1.375 (6) |
N1—C6 | 1.403 (6) | C5—C6 | 1.427 (7) |
N3—C2 | 1.301 (6) | C8—H8 | 0.98 (6) |
N3—C4 | 1.355 (6) | N11—O11 | 1.254 (5) |
N7—C5 | 1.377 (6) | N11—O12 | 1.262 (5) |
N7—C8 | 1.332 (7) | N11—O13 | 1.257 (5) |
N7—H7 | 0.88 (6) | O1—H1A | 0.95 (8) |
N9—C4 | 1.370 (6) | O1—H1B | 0.79 (6) |
N9—C8 | 1.340 (6) | | |
| | | |
C2—N1—H1 | 117.5 | N9—C4—C5 | 106.8 (4) |
C2—N1—C6 | 125.0 (4) | N7—C5—C6 | 131.9 (4) |
C6—N1—H1 | 117.5 | C4—C5—N7 | 107.0 (4) |
C2—N3—C4 | 112.4 (4) | C4—C5—C6 | 121.0 (4) |
C5—N7—H7 | 124 (4) | O6—C6—N1 | 121.3 (4) |
C8—N7—C5 | 108.5 (4) | O6—C6—C5 | 129.2 (4) |
C8—N7—H7 | 128 (4) | N1—C6—C5 | 109.6 (4) |
C4—N9—H9 | 122 (4) | N7—C8—N9 | 109.0 (4) |
C8—N9—C4 | 108.7 (4) | N7—C8—H8 | 124 (4) |
C8—N9—H9 | 130 (4) | N9—C8—H8 | 127 (4) |
N1—C2—H2 | 117.4 | O11—N11—O12 | 119.6 (4) |
N3—C2—N1 | 125.2 (5) | O11—N11—O13 | 120.3 (4) |
N3—C2—H2 | 117.4 | O13—N11—O12 | 120.1 (4) |
N3—C4—N9 | 126.5 (4) | H1A—O1—H1B | 111 (5) |
N3—C4—C5 | 126.7 (5) | | |
| | | |
N3—C4—C5—N7 | −179.5 (5) | C4—N3—C2—N1 | 0.4 (7) |
N3—C4—C5—C6 | 1.1 (8) | C4—N9—C8—N7 | −0.2 (6) |
N7—C5—C6—O6 | 0.3 (10) | C4—C5—C6—O6 | 179.5 (5) |
N7—C5—C6—N1 | −179.9 (5) | C4—C5—C6—N1 | −0.7 (7) |
N9—C4—C5—N7 | 0.0 (6) | C5—N7—C8—N9 | 0.2 (6) |
N9—C4—C5—C6 | −179.4 (5) | C6—N1—C2—N3 | −0.2 (8) |
C2—N1—C6—O6 | −179.9 (5) | C8—N7—C5—C4 | −0.1 (6) |
C2—N1—C6—C5 | 0.3 (7) | C8—N7—C5—C6 | 179.1 (5) |
C2—N3—C4—N9 | 179.6 (5) | C8—N9—C4—N3 | 179.7 (5) |
C2—N3—C4—C5 | −0.9 (8) | C8—N9—C4—C5 | 0.1 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O12_$1i | 0.88 | 2.31 | 2.941 (5) | 129 |
N1—H1···O11_$1i | 0.88 | 2.14 | 3.015 (5) | 172 |
O1—H1A···N3 | 0.95 (8) | 2.06 (7) | 2.918 (5) | 150 (6) |
N7—H7···O13_$2ii | 0.88 (6) | 2.60 (7) | 3.209 (5) | 128 (5) |
N7—H7···O12_$2ii | 0.88 (6) | 1.84 (6) | 2.710 (5) | 174 (6) |
C2—H2···O12_$1i | 0.95 | 2.42 | 3.017 (6) | 121 |
C2—H2···O6_$3iii | 0.95 | 2.62 | 3.476 (6) | 151 |
N9—H9···O11 | 0.85 (7) | 2.50 (6) | 3.096 (5) | 128 (5) |
N9—H9···O13 | 0.85 (7) | 1.92 (7) | 2.772 (5) | 175 (6) |
C8—H8···O1_$2ii | 0.98 (6) | 2.14 (7) | 3.112 (6) | 173 (5) |
O1—H1B···O6_$3iii | 0.79 (6) | 2.22 (6) | 2.988 (5) | 164 (5) |
Symmetry codes: (i) x, y, z+1; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+3/2. |
6-Oxo-1
H,7
H-purin-9-ium nitrate monohydrate (hx1_105k)
top
Crystal data top
C5H5N4O+·NO3−·H2O | F(000) = 448 |
Mr = 217.16 | Dx = 1.712 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.1381 (4) Å | Cell parameters from 3258 reflections |
b = 13.7467 (8) Å | θ = 3.6–31.7° |
c = 10.0349 (5) Å | µ = 0.15 mm−1 |
β = 95.813 (5)° | T = 105 K |
V = 842.38 (9) Å3 | Block, clear light colourless |
Z = 4 | 0.19 × 0.1 × 0.08 mm |
Data collection top
Agilent Technologies SuperNova four-circle diffractometer equipped with a
micro-focus sealed tube and an Eos CCD detector | 3966 reflections with I > 2σ(I) |
Detector resolution: 8.0013 pixels mm-1 | Rint = 0.041 |
ω scans | θmax = 32.5°, θmin = 2.5° |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015) | h = −8→9 |
Tmin = 0.978, Tmax = 0.989 | k = −20→20 |
25288 measured reflections | l = −15→14 |
5823 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Only H-atom coordinates refined |
wR(F2) = 0.084 | w = 1/[σ2(Fo2) + (0.0422P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.93 | (Δ/σ)max < 0.001 |
5823 reflections | Δρmax = 0.40 e Å−3 |
163 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | |
Special details top
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. Refined as a 2-component twin. All crystal structures were determined using an Agilent
Technologies SuperNova four-circle diffractometer equipped with a micro-focus
sealed tube and an Eos CCD detector. The temperature was controlled with an
Oxford Cryosystems low-temperature nitrogen gas-flow device. For helium
measurements, a CRYOCOOL-LHe gas stream cooler was used. Unit-cell
determination, data reduction, and absorption correction were performed using
CrysAlis PRO Version 1.171.38.46 (Agilent Technologies, 2014). All structures
were solved and refined using ShelXT (Sheldrick, 2015b) with intrinsic phasing
and refined with ShelXL (Sheldrick, 2015a) with least-squares within
OLEX2
graphical environment (Dolomanov et al., 2009). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O6 | 0.24738 (14) | 0.79173 (6) | 0.77511 (8) | 0.0188 (2) | |
N1 | 0.24700 (17) | 0.62535 (7) | 0.75254 (10) | 0.0161 (2) | |
H1 | 0.246 (2) | 0.6176 (10) | 0.8496 (15) | 0.019* | |
N3 | 0.25332 (17) | 0.53913 (7) | 0.54892 (10) | 0.0154 (2) | |
N7 | 0.25577 (17) | 0.78846 (7) | 0.46481 (10) | 0.0152 (2) | |
H7 | 0.255 (2) | 0.8550 (12) | 0.4829 (17) | 0.036 (5)* | |
N9 | 0.26142 (17) | 0.64979 (8) | 0.36095 (10) | 0.0155 (2) | |
H9 | 0.264 (3) | 0.6062 (12) | 0.2995 (18) | 0.035 (5)* | |
C2 | 0.2488 (2) | 0.54234 (9) | 0.67932 (12) | 0.0165 (3) | |
H2 | 0.249 (2) | 0.4836 (10) | 0.7283 (14) | 0.020* | |
C4 | 0.25523 (18) | 0.62932 (9) | 0.49445 (11) | 0.0137 (2) | |
C5 | 0.25157 (19) | 0.71626 (8) | 0.55981 (12) | 0.0136 (2) | |
C6 | 0.24789 (19) | 0.72009 (8) | 0.70160 (12) | 0.0145 (2) | |
C8 | 0.2611 (2) | 0.74652 (9) | 0.34573 (13) | 0.0164 (2) | |
H8 | 0.262 (2) | 0.7835 (11) | 0.2575 (16) | 0.030 (4)* | |
N11 | 0.25550 (18) | 0.53325 (8) | 0.06857 (10) | 0.0168 (2) | |
O11 | 0.25554 (16) | 0.62316 (6) | 0.05431 (9) | 0.0229 (2) | |
O12 | 0.24570 (16) | 0.47903 (6) | −0.03341 (8) | 0.0209 (2) | |
O13 | 0.26426 (16) | 0.49552 (6) | 0.18263 (8) | 0.0217 (2) | |
O1 | 0.24421 (16) | 0.34388 (7) | 0.43422 (10) | 0.0190 (2) | |
H1A | 0.246 (3) | 0.3130 (13) | 0.510 (2) | 0.042 (5)* | |
H1B | 0.245 (3) | 0.4056 (15) | 0.4560 (17) | 0.044 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O6 | 0.0271 (5) | 0.0137 (4) | 0.0157 (4) | 0.0002 (4) | 0.0028 (3) | −0.0034 (3) |
N1 | 0.0228 (5) | 0.0133 (5) | 0.0125 (4) | 0.0006 (4) | 0.0024 (4) | 0.0010 (4) |
N3 | 0.0199 (5) | 0.0110 (4) | 0.0154 (5) | 0.0000 (4) | 0.0018 (4) | −0.0001 (4) |
N7 | 0.0194 (5) | 0.0118 (4) | 0.0146 (5) | −0.0006 (4) | 0.0023 (4) | 0.0007 (4) |
N9 | 0.0194 (5) | 0.0146 (5) | 0.0127 (5) | −0.0002 (4) | 0.0025 (4) | −0.0016 (4) |
C2 | 0.0209 (7) | 0.0114 (5) | 0.0172 (6) | −0.0002 (5) | 0.0015 (5) | −0.0001 (5) |
C4 | 0.0140 (6) | 0.0146 (5) | 0.0124 (5) | 0.0001 (5) | 0.0015 (4) | −0.0006 (4) |
C5 | 0.0147 (5) | 0.0123 (5) | 0.0139 (5) | −0.0003 (5) | 0.0020 (4) | 0.0007 (4) |
C6 | 0.0154 (6) | 0.0130 (5) | 0.0150 (5) | 0.0005 (5) | 0.0017 (4) | 0.0003 (5) |
C8 | 0.0176 (6) | 0.0166 (6) | 0.0153 (6) | −0.0003 (5) | 0.0030 (4) | 0.0005 (5) |
N11 | 0.0237 (5) | 0.0139 (5) | 0.0128 (5) | 0.0012 (4) | 0.0019 (4) | −0.0004 (4) |
O11 | 0.0399 (5) | 0.0096 (4) | 0.0192 (5) | 0.0005 (4) | 0.0032 (4) | 0.0010 (4) |
O12 | 0.0361 (5) | 0.0150 (4) | 0.0119 (4) | −0.0003 (4) | 0.0034 (4) | −0.0021 (3) |
O13 | 0.0376 (5) | 0.0169 (4) | 0.0106 (4) | 0.0016 (4) | 0.0027 (4) | 0.0025 (4) |
O1 | 0.0263 (5) | 0.0137 (4) | 0.0173 (4) | −0.0007 (4) | 0.0030 (4) | −0.0011 (4) |
Geometric parameters (Å, º) top
O6—C6 | 1.2307 (14) | N9—C8 | 1.3384 (16) |
N1—H1 | 0.981 (14) | C2—H2 | 0.946 (14) |
N1—C2 | 1.3579 (16) | C4—C5 | 1.3646 (16) |
N1—C6 | 1.3993 (15) | C5—C6 | 1.4263 (17) |
N3—C2 | 1.3124 (16) | C8—H8 | 1.022 (16) |
N3—C4 | 1.3554 (14) | N11—O11 | 1.2443 (13) |
N7—H7 | 0.932 (16) | N11—O12 | 1.2625 (12) |
N7—C5 | 1.3782 (15) | N11—O13 | 1.2527 (12) |
N7—C8 | 1.3301 (16) | O1—H1A | 0.866 (19) |
N9—H9 | 0.861 (18) | O1—H1B | 0.88 (2) |
N9—C4 | 1.3732 (15) | | |
| | | |
C2—N1—H1 | 116.6 (9) | C5—C4—N9 | 107.02 (11) |
C2—N1—C6 | 125.73 (11) | N7—C5—C6 | 131.82 (11) |
C6—N1—H1 | 117.7 (9) | C4—C5—N7 | 107.21 (10) |
C2—N3—C4 | 111.92 (10) | C4—C5—C6 | 120.96 (11) |
C5—N7—H7 | 124.8 (10) | O6—C6—N1 | 121.70 (11) |
C8—N7—H7 | 127.0 (10) | O6—C6—C5 | 128.96 (11) |
C8—N7—C5 | 108.25 (10) | N1—C6—C5 | 109.34 (10) |
C4—N9—H9 | 124.1 (11) | N7—C8—N9 | 109.14 (11) |
C8—N9—H9 | 127.5 (11) | N7—C8—H8 | 124.5 (9) |
C8—N9—C4 | 108.37 (10) | N9—C8—H8 | 126.3 (9) |
N1—C2—H2 | 115.9 (8) | O11—N11—O12 | 119.58 (10) |
N3—C2—N1 | 124.74 (11) | O11—N11—O13 | 121.06 (10) |
N3—C2—H2 | 119.4 (8) | O13—N11—O12 | 119.36 (10) |
N3—C4—N9 | 125.67 (11) | H1A—O1—H1B | 105.0 (15) |
N3—C4—C5 | 127.30 (11) | | |
| | | |
N3—C4—C5—N7 | 179.93 (12) | C4—N3—C2—N1 | −0.20 (17) |
N3—C4—C5—C6 | 0.8 (2) | C4—N9—C8—N7 | 0.22 (14) |
N7—C5—C6—O6 | 0.1 (2) | C4—C5—C6—O6 | 178.90 (13) |
N7—C5—C6—N1 | −179.29 (13) | C4—C5—C6—N1 | −0.47 (16) |
N9—C4—C5—N7 | −0.05 (13) | C5—N7—C8—N9 | −0.25 (15) |
N9—C4—C5—C6 | −179.13 (11) | C6—N1—C2—N3 | 0.5 (2) |
C2—N1—C6—O6 | −179.56 (12) | C8—N7—C5—C4 | 0.18 (14) |
C2—N1—C6—C5 | −0.13 (16) | C8—N7—C5—C6 | 179.12 (13) |
C2—N3—C4—N9 | 179.50 (11) | C8—N9—C4—N3 | 179.92 (12) |
C2—N3—C4—C5 | −0.47 (18) | C8—N9—C4—C5 | −0.10 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O12_$1i | 0.98 (1) | 2.24 (1) | 2.9433 (13) | 128 (1) |
N1—H1···O11_$1i | 0.98 (1) | 2.05 (2) | 3.0235 (14) | 171 (1) |
N7—H7···O12_$2ii | 0.932 (16) | 1.780 (16) | 2.7090 (14) | 174.7 (16) |
N7—H7···O13_$2ii | 0.932 (16) | 2.543 (16) | 3.2046 (13) | 128.2 (13) |
N9—H9···O11 | 0.861 (18) | 2.467 (18) | 3.0954 (13) | 130.5 (14) |
N9—H9···O13 | 0.861 (18) | 1.921 (18) | 2.7761 (14) | 171.7 (16) |
C2—H2···O6_$3iii | 0.95 (1) | 2.64 (1) | 3.4750 (15) | 148 (1) |
C2—H2···O12_$1i | 0.95 (1) | 2.39 (1) | 3.0131 (15) | 123 (1) |
C8—H8···O1_$2ii | 1.022 (16) | 2.092 (16) | 3.1090 (16) | 173.4 (13) |
O1—H1A···O6_$3iii | 0.866 (19) | 2.18 (2) | 2.9990 (13) | 158.3 (16) |
O1—H1B···N3 | 0.88 (2) | 2.06 (2) | 2.9187 (14) | 167.5 (16) |
Symmetry codes: (i) x, y, z+1; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+3/2. |
6-Oxo-1
H,7
H-purin-9-ium nitrate monohydrate (hx1_285k)
top
Crystal data top
C5H5N4O+·NO3−·H2O | Dx = 1.668 Mg m−3 |
Mr = 217.16 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pmnb | Cell parameters from 4619 reflections |
a = 6.241 (4) Å | θ = 2.5–31.7° |
b = 13.726 (3) Å | µ = 0.15 mm−1 |
c = 10.095 (5) Å | T = 285 K |
V = 864.8 (7) Å3 | Block, clear light colourless |
Z = 4 | 0.18 × 0.10 × 0.1 mm |
F(000) = 448 | |
Data collection top
Agilent Technologies SuperNova four-circle diffractometer equipped with a
micro-focus sealed tube and an Eos CCD detector | 1162 reflections with I > 2σ(I) |
Detector resolution: 8.0013 pixels mm-1 | Rint = 0.036 |
ω scans | θmax = 32.4°, θmin = 2.5° |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015) | h = −9→9 |
Tmin = 0.796, Tmax = 1.000 | k = −20→20 |
16933 measured reflections | l = −15→15 |
1636 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | All H-atom parameters refined |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0565P)2 + 0.1425P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.002 |
1636 reflections | Δρmax = 0.23 e Å−3 |
112 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | |
Special details top
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. All crystal structures were determined using an Agilent
Technologies SuperNova four-circle diffractometer equipped with a micro-focus
sealed tube and an Eos CCD detector. The temperature was controlled with an
Oxford Cryosystems low-temperature nitrogen gas-flow device. For helium
measurements, a CRYOCOOL-LHe gas stream cooler was used. Unit-cell
determination, data reduction, and absorption correction were performed using
CrysAlis PRO Version 1.171.38.46 (Agilent Technologies, 2014). All structures
were solved and refined using ShelXT (Sheldrick, 2015b) with intrinsic phasing
and refined with ShelXL (Sheldrick, 2015a) with least-squares within
OLEX2
graphical environment (Dolomanov et al., 2009). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O6 | 0.250000 | 0.21060 (10) | 0.22449 (14) | 0.0522 (4) | |
N1 | 0.250000 | 0.37669 (11) | 0.24813 (16) | 0.0434 (4) | |
H1 | 0.250000 | 0.386 (2) | 0.156 (3) | 0.074 (8)* | |
N3 | 0.250000 | 0.46225 (11) | 0.45096 (15) | 0.0425 (4) | |
N7 | 0.250000 | 0.21261 (11) | 0.53303 (15) | 0.0400 (3) | |
H7 | 0.250000 | 0.145 (2) | 0.514 (3) | 0.069 (8)* | |
N9 | 0.250000 | 0.35077 (13) | 0.63774 (15) | 0.0428 (4) | |
H9 | 0.250000 | 0.391 (2) | 0.707 (3) | 0.071 (8)* | |
C2 | 0.250000 | 0.45935 (14) | 0.32126 (19) | 0.0450 (4) | |
H2 | 0.250000 | 0.5191 (17) | 0.270 (2) | 0.048 (6)* | |
C4 | 0.250000 | 0.37185 (12) | 0.50481 (17) | 0.0355 (3) | |
C5 | 0.250000 | 0.28503 (12) | 0.43899 (16) | 0.0355 (3) | |
C6 | 0.250000 | 0.28188 (13) | 0.29782 (17) | 0.0384 (4) | |
C8 | 0.250000 | 0.25417 (15) | 0.6517 (2) | 0.0449 (4) | |
H8 | 0.250000 | 0.2187 (18) | 0.738 (3) | 0.057 (7)* | |
N11 | 0.250000 | 0.46700 (11) | 0.93010 (14) | 0.0453 (4) | |
O12 | 0.250000 | 0.51997 (10) | 1.03138 (13) | 0.0564 (4) | |
O11 | 0.250000 | 0.37762 (10) | 0.94277 (15) | 0.0646 (5) | |
O13 | 0.250000 | 0.50589 (10) | 0.81851 (13) | 0.0588 (4) | |
O1 | 0.250000 | 0.65786 (11) | 0.56856 (16) | 0.0500 (4) | |
H1A | 0.250000 | 0.686 (2) | 0.503 (4) | 0.081 (10)* | |
H1B | 0.250000 | 0.595 (2) | 0.547 (3) | 0.064 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O6 | 0.0829 (10) | 0.0376 (7) | 0.0360 (7) | 0.000 | 0.000 | −0.0079 (5) |
N1 | 0.0636 (9) | 0.0355 (8) | 0.0313 (7) | 0.000 | 0.000 | 0.0021 (6) |
N3 | 0.0584 (9) | 0.0295 (7) | 0.0397 (7) | 0.000 | 0.000 | −0.0019 (6) |
N7 | 0.0526 (9) | 0.0313 (7) | 0.0362 (7) | 0.000 | 0.000 | 0.0039 (6) |
N9 | 0.0557 (9) | 0.0421 (8) | 0.0306 (7) | 0.000 | 0.000 | −0.0037 (6) |
C2 | 0.0623 (11) | 0.0315 (8) | 0.0412 (9) | 0.000 | 0.000 | 0.0027 (7) |
C4 | 0.0431 (8) | 0.0329 (8) | 0.0305 (7) | 0.000 | 0.000 | −0.0030 (6) |
C5 | 0.0434 (8) | 0.0303 (7) | 0.0327 (8) | 0.000 | 0.000 | 0.0009 (6) |
C6 | 0.0504 (9) | 0.0318 (7) | 0.0329 (8) | 0.000 | 0.000 | −0.0007 (6) |
C8 | 0.0547 (10) | 0.0465 (10) | 0.0336 (8) | 0.000 | 0.000 | 0.0033 (8) |
N11 | 0.0728 (11) | 0.0318 (7) | 0.0312 (7) | 0.000 | 0.000 | −0.0014 (6) |
O12 | 0.1010 (12) | 0.0373 (7) | 0.0309 (6) | 0.000 | 0.000 | −0.0033 (5) |
O11 | 0.1153 (15) | 0.0292 (7) | 0.0494 (8) | 0.000 | 0.000 | 0.0021 (6) |
O13 | 0.1059 (12) | 0.0421 (8) | 0.0285 (6) | 0.000 | 0.000 | 0.0029 (5) |
O1 | 0.0705 (10) | 0.0348 (7) | 0.0448 (8) | 0.000 | 0.000 | −0.0036 (6) |
Geometric parameters (Å, º) top
O6—C6 | 1.227 (2) | N9—C8 | 1.333 (3) |
N1—H1 | 0.94 (3) | C2—H2 | 0.97 (2) |
N1—C2 | 1.354 (2) | C4—C5 | 1.364 (2) |
N1—C6 | 1.395 (2) | C5—C6 | 1.426 (3) |
N3—C2 | 1.310 (2) | C8—H8 | 1.00 (3) |
N3—C4 | 1.355 (2) | N11—O12 | 1.2546 (19) |
N7—H7 | 0.95 (3) | N11—O11 | 1.233 (2) |
N7—C5 | 1.375 (2) | N11—O13 | 1.247 (2) |
N7—C8 | 1.327 (3) | O1—H1A | 0.77 (4) |
N9—H9 | 0.90 (3) | O1—H1B | 0.89 (3) |
N9—C4 | 1.373 (2) | | |
| | | |
C2—N1—H1 | 115.0 (18) | C5—C4—N9 | 106.98 (15) |
C2—N1—C6 | 125.87 (17) | N7—C5—C6 | 131.95 (16) |
C6—N1—H1 | 119.1 (18) | C4—C5—N7 | 107.17 (15) |
C2—N3—C4 | 111.92 (15) | C4—C5—C6 | 120.88 (16) |
C5—N7—H7 | 124.6 (18) | O6—C6—N1 | 121.81 (17) |
C8—N7—H7 | 127.2 (18) | O6—C6—C5 | 128.85 (17) |
C8—N7—C5 | 108.23 (16) | N1—C6—C5 | 109.34 (15) |
C4—N9—H9 | 129.4 (18) | N7—C8—N9 | 109.39 (17) |
C8—N9—H9 | 122.4 (18) | N7—C8—H8 | 125.3 (15) |
C8—N9—C4 | 108.23 (15) | N9—C8—H8 | 125.4 (15) |
N1—C2—H2 | 114.7 (13) | O11—N11—O12 | 119.46 (15) |
N3—C2—N1 | 124.79 (17) | O11—N11—O13 | 121.30 (16) |
N3—C2—H2 | 120.5 (13) | O13—N11—O12 | 119.23 (16) |
N3—C4—N9 | 125.82 (15) | H1A—O1—H1B | 106 (3) |
N3—C4—C5 | 127.19 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O12_$1i | 0.94 (3) | 2.22 (3) | 2.942 (2) | 132 (2) |
N1—H1···O11_$1i | 0.94 (3) | 2.15 (3) | 3.083 (3) | 169 (3) |
N7—H7···O13_$2ii | 0.95 (3) | 2.55 (3) | 3.209 (2) | 127 (2) |
N7—H7···O12_$2ii | 0.95 (3) | 1.77 (3) | 2.723 (2) | 177 (3) |
N9—H9···O11 | 0.90 (3) | 2.38 (3) | 3.101 (3) | 137 (2) |
N9—H9···O13 | 0.90 (3) | 1.93 (3) | 2.804 (2) | 164 (3) |
C2—H2···O6_$3iii | 0.97 (2) | 2.63 (2) | 3.480 (2) | 147 (2) |
C2—H2···O6_$3iii | 0.97 (2) | 2.63 (2) | 3.480 (2) | 147 (2) |
C8—H8···O1_$2ii | 1.00 (3) | 2.13 (3) | 3.118 (3) | 174 (2) |
O1—H1B···N3 | 0.89 (3) | 2.06 (3) | 2.936 (2) | 166 (2) |
Symmetry codes: (i) x, y, z−1; (ii) −x+1/2, y−1/2, −z+3/2; (iii) −x+1/2, y+1/2, −z+1/2. |
Oxidanium 6-Oxo-1
H,7
H-purin-9-ium dinitrate dihydrate (hx2_20k)
top
Crystal data top
H3O+·C5H5N4O+·2NO3−·2H2O | F(000) = 656 |
Mr = 316.21 | Dx = 1.745 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.8485 (8) Å | Cell parameters from 1478 reflections |
b = 10.1717 (6) Å | θ = 2.7–27.5° |
c = 11.2851 (11) Å | µ = 0.17 mm−1 |
β = 104.812 (9)° | T = 20 K |
V = 1203.91 (17) Å3 | Block, clear light colourless |
Z = 4 | 0.18 × 0.1 × 0.09 mm |
Data collection top
Agilent Technologies SuperNova four-circle diffractometer equipped with a
micro-focus sealed tube and an Eos CCD detector | 2002 reflections with I > 2σ(I) |
Detector resolution: 16.0026 pixels mm-1 | Rint = 0.041 |
ω scans | θmax = 28.2°, θmin = 2.3° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −10→14 |
Tmin = 0.683, Tmax = 1.000 | k = −10→13 |
4511 measured reflections | l = −14→12 |
2640 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | All H-atom parameters refined |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0542P)2 + 0.5897P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
2640 reflections | Δρmax = 0.35 e Å−3 |
238 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | |
Special details top
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. All crystal structures were determined using an Agilent
Technologies SuperNova four-circle diffractometer equipped with a micro-focus
sealed tube and an Eos CCD detector. The temperature was controlled with an
Oxford Cryosystems low-temperature nitrogen gas-flow device. For helium
measurements, a CRYOCOOL-LHe gas stream cooler was used. Unit-cell
determination, data reduction, and absorption correction were performed using
CrysAlis PRO Version 1.171.38.46 (Agilent Technologies, 2014). All structures
were solved and refined using ShelXT (Sheldrick, 2015b) with intrinsic phasing
and refined with ShelXL (Sheldrick, 2015a) with least-squares within
OLEX2
graphical environment (Dolomanov et al., 2009). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O6 | 0.29687 (15) | 0.22634 (16) | 0.13091 (16) | 0.0116 (4) | |
N1 | 0.46780 (19) | 0.2440 (2) | 0.30005 (19) | 0.0106 (5) | |
H1 | 0.476 (3) | 0.148 (3) | 0.303 (3) | 0.032 (9)* | |
N3 | 0.55907 (19) | 0.44304 (19) | 0.3903 (2) | 0.0108 (5) | |
N7 | 0.30425 (19) | 0.5334 (2) | 0.1377 (2) | 0.0101 (4) | |
H7 | 0.231 (4) | 0.525 (4) | 0.066 (4) | 0.051 (11)* | |
N9 | 0.44720 (19) | 0.6333 (2) | 0.2815 (2) | 0.0098 (4) | |
H9 | 0.489 (3) | 0.698 (3) | 0.328 (3) | 0.019 (8)* | |
C2 | 0.5546 (2) | 0.3149 (2) | 0.3847 (2) | 0.0106 (5) | |
H2 | 0.614 (3) | 0.264 (3) | 0.444 (3) | 0.015 (7)* | |
C4 | 0.4667 (2) | 0.5003 (2) | 0.3000 (2) | 0.0095 (5) | |
C5 | 0.3770 (2) | 0.4369 (2) | 0.2101 (2) | 0.0100 (5) | |
C6 | 0.3720 (2) | 0.2974 (2) | 0.2042 (2) | 0.0100 (5) | |
C8 | 0.3490 (2) | 0.6495 (2) | 0.1828 (2) | 0.0100 (5) | |
H8 | 0.316 (2) | 0.734 (3) | 0.150 (2) | 0.007 (6)* | |
N11 | 0.55299 (19) | 0.92711 (19) | 0.3917 (2) | 0.0107 (5) | |
O12 | 0.61072 (16) | 1.02817 (16) | 0.44319 (16) | 0.0120 (4) | |
O11 | 0.46190 (16) | 0.93936 (17) | 0.29922 (16) | 0.0136 (4) | |
O13 | 0.58955 (16) | 0.81559 (16) | 0.43504 (16) | 0.0122 (4) | |
O1 | 0.78417 (18) | 0.54153 (19) | 0.55631 (18) | 0.0142 (4) | |
H1A | 0.721 (4) | 0.529 (4) | 0.492 (4) | 0.067 (14)* | |
H1B | 0.807 (3) | 0.464 (4) | 0.593 (3) | 0.035 (10)* | |
O2 | 0.96465 (18) | 0.64482 (19) | 0.47990 (18) | 0.0124 (4) | |
H2A | 0.905 (4) | 0.596 (3) | 0.504 (3) | 0.040 (10)* | |
H2B | 0.927 (4) | 0.705 (4) | 0.442 (4) | 0.056 (13)* | |
H2C | 1.041 (4) | 0.646 (3) | 0.545 (4) | 0.047 (11)* | |
O3 | 0.86372 (19) | 0.84115 (19) | 0.36947 (19) | 0.0152 (4) | |
H3A | 0.876 (3) | 0.912 (3) | 0.388 (3) | 0.005 (7)* | |
H3B | 0.795 (4) | 0.841 (4) | 0.303 (4) | 0.066 (14)* | |
N21 | 0.66662 (19) | 0.6611 (2) | 0.1634 (2) | 0.0112 (5) | |
O21 | 0.73986 (16) | 0.60242 (17) | 0.24839 (16) | 0.0143 (4) | |
O22 | 0.59503 (16) | 0.60095 (17) | 0.07416 (16) | 0.0136 (4) | |
O23 | 0.66012 (16) | 0.78801 (16) | 0.16425 (16) | 0.0129 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O6 | 0.0087 (8) | 0.0096 (8) | 0.0154 (9) | −0.0024 (7) | 0.0008 (7) | −0.0030 (7) |
N1 | 0.0076 (10) | 0.0099 (10) | 0.0141 (11) | 0.0000 (8) | 0.0023 (8) | 0.0015 (8) |
N3 | 0.0079 (10) | 0.0107 (10) | 0.0145 (11) | 0.0003 (8) | 0.0040 (9) | 0.0002 (8) |
N7 | 0.0063 (10) | 0.0105 (10) | 0.0128 (11) | 0.0006 (8) | 0.0012 (8) | 0.0009 (8) |
N9 | 0.0097 (10) | 0.0068 (10) | 0.0130 (11) | −0.0008 (8) | 0.0033 (9) | −0.0013 (8) |
C2 | 0.0054 (11) | 0.0135 (12) | 0.0135 (13) | −0.0003 (10) | 0.0036 (10) | 0.0010 (10) |
C4 | 0.0084 (11) | 0.0077 (11) | 0.0137 (12) | 0.0014 (9) | 0.0051 (9) | 0.0010 (9) |
C5 | 0.0077 (12) | 0.0093 (12) | 0.0135 (12) | 0.0009 (9) | 0.0037 (10) | −0.0007 (10) |
C6 | 0.0062 (11) | 0.0133 (12) | 0.0114 (12) | 0.0015 (10) | 0.0042 (9) | 0.0011 (10) |
C8 | 0.0059 (11) | 0.0120 (12) | 0.0126 (13) | 0.0013 (10) | 0.0031 (10) | 0.0008 (10) |
N11 | 0.0073 (10) | 0.0105 (10) | 0.0149 (11) | 0.0008 (8) | 0.0040 (9) | 0.0004 (8) |
O12 | 0.0098 (8) | 0.0093 (8) | 0.0160 (9) | −0.0036 (7) | 0.0013 (7) | −0.0026 (7) |
O11 | 0.0095 (9) | 0.0155 (9) | 0.0132 (9) | 0.0008 (7) | −0.0019 (7) | 0.0008 (7) |
O13 | 0.0123 (9) | 0.0084 (8) | 0.0148 (9) | 0.0019 (7) | 0.0011 (7) | 0.0018 (7) |
O1 | 0.0109 (9) | 0.0137 (9) | 0.0157 (10) | −0.0006 (8) | −0.0010 (8) | 0.0028 (8) |
O2 | 0.0090 (9) | 0.0111 (9) | 0.0161 (10) | 0.0010 (8) | 0.0013 (8) | 0.0027 (8) |
O3 | 0.0148 (10) | 0.0079 (10) | 0.0197 (11) | −0.0017 (8) | −0.0016 (8) | −0.0012 (8) |
N21 | 0.0081 (10) | 0.0095 (10) | 0.0167 (11) | −0.0024 (8) | 0.0044 (9) | −0.0008 (9) |
O21 | 0.0104 (9) | 0.0133 (9) | 0.0159 (10) | 0.0006 (7) | −0.0028 (7) | 0.0033 (8) |
O22 | 0.0114 (9) | 0.0125 (9) | 0.0148 (10) | −0.0021 (7) | −0.0007 (7) | −0.0034 (7) |
O23 | 0.0103 (9) | 0.0092 (9) | 0.0175 (9) | 0.0015 (7) | 0.0007 (7) | −0.0012 (7) |
Geometric parameters (Å, º) top
O6—C6 | 1.235 (3) | C8—H8 | 0.97 (3) |
N1—H1 | 0.98 (3) | N11—O12 | 1.265 (3) |
N1—C2 | 1.364 (3) | N11—O11 | 1.247 (3) |
N1—C6 | 1.404 (3) | N11—O13 | 1.259 (3) |
N3—C2 | 1.305 (3) | O1—H1A | 0.87 (5) |
N3—C4 | 1.364 (3) | O1—H1B | 0.89 (4) |
N7—H7 | 0.98 (4) | O2—H2A | 0.91 (4) |
N7—C5 | 1.387 (3) | O2—H2B | 0.80 (4) |
N7—C8 | 1.329 (3) | O2—H2C | 0.96 (4) |
N9—H9 | 0.88 (3) | O3—H3A | 0.75 (3) |
N9—C4 | 1.377 (3) | O3—H3B | 0.91 (5) |
N9—C8 | 1.340 (3) | N21—O21 | 1.232 (3) |
C2—H2 | 0.95 (3) | N21—O22 | 1.262 (3) |
C4—C5 | 1.374 (3) | N21—O23 | 1.293 (3) |
C5—C6 | 1.421 (3) | | |
| | | |
C2—N1—H1 | 117.6 (19) | C4—C5—C6 | 121.0 (2) |
C2—N1—C6 | 125.3 (2) | O6—C6—N1 | 121.4 (2) |
C6—N1—H1 | 117 (2) | O6—C6—C5 | 128.8 (2) |
C2—N3—C4 | 112.3 (2) | N1—C6—C5 | 109.8 (2) |
C5—N7—H7 | 130 (2) | N7—C8—N9 | 110.1 (2) |
C8—N7—H7 | 122 (2) | N7—C8—H8 | 125.6 (16) |
C8—N7—C5 | 107.8 (2) | N9—C8—H8 | 124.3 (16) |
C4—N9—H9 | 126.9 (19) | O11—N11—O12 | 119.8 (2) |
C8—N9—H9 | 125.2 (19) | O11—N11—O13 | 121.3 (2) |
C8—N9—C4 | 107.8 (2) | O13—N11—O12 | 119.0 (2) |
N1—C2—H2 | 115.0 (17) | H1A—O1—H1B | 109 (4) |
N3—C2—N1 | 124.9 (2) | H2A—O2—H2B | 106 (3) |
N3—C2—H2 | 120.0 (17) | H2A—O2—H2C | 109 (3) |
N3—C4—N9 | 126.0 (2) | H2B—O2—H2C | 129 (4) |
N3—C4—C5 | 126.7 (2) | H3A—O3—H3B | 107 (3) |
C5—C4—N9 | 107.3 (2) | O21—N21—O22 | 122.0 (2) |
N7—C5—C6 | 132.1 (2) | O21—N21—O23 | 120.2 (2) |
C4—C5—N7 | 106.9 (2) | O22—N21—O23 | 117.8 (2) |
| | | |
N3—C4—C5—N7 | −179.1 (2) | C4—N3—C2—N1 | −0.6 (3) |
N3—C4—C5—C6 | 0.7 (4) | C4—N9—C8—N7 | 0.4 (3) |
N7—C5—C6—O6 | −1.3 (5) | C4—C5—C6—O6 | 178.9 (2) |
N7—C5—C6—N1 | 180.0 (2) | C4—C5—C6—N1 | 0.3 (3) |
N9—C4—C5—N7 | 0.2 (3) | C5—N7—C8—N9 | −0.3 (3) |
N9—C4—C5—C6 | −180.0 (2) | C6—N1—C2—N3 | 1.6 (4) |
C2—N1—C6—O6 | 179.9 (2) | C8—N7—C5—C4 | 0.0 (3) |
C2—N1—C6—C5 | −1.3 (3) | C8—N7—C5—C6 | −179.8 (3) |
C2—N3—C4—N9 | −179.8 (2) | C8—N9—C4—N3 | 179.0 (2) |
C2—N3—C4—C5 | −0.5 (4) | C8—N9—C4—C5 | −0.4 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O12_$5i | 0.98 (3) | 2.23 (3) | 2.924 (3) | 127 (3) |
N1—H1···O11_$5i | 0.98 (3) | 2.13 (3) | 3.099 (3) | 171 (3) |
N7—H7···O13_$1ii | 0.98 (4) | 2.45 (4) | 3.208 (3) | 133 (3) |
N7—H7···O12_$1ii | 0.98 (4) | 1.73 (4) | 2.695 (3) | 167 (3) |
N9—H9···O11 | 0.88 (3) | 2.49 (3) | 3.121 (3) | 129 (2) |
N9—H9···O13 | 0.88 (3) | 1.85 (3) | 2.731 (3) | 173 (3) |
C2—H2···O6_$2iii | 0.95 (3) | 2.50 (3) | 3.327 (3) | 145 (2) |
C2—H2···O12_$5i | 0.95 (3) | 2.40 (3) | 3.018 (3) | 122 (2) |
C8—H8···O1_$1ii | 0.97 (3) | 2.50 (3) | 3.449 (3) | 166 (2) |
O1—H1A···N3 | 0.87 (5) | 2.03 (5) | 2.853 (3) | 156 (4) |
O1—H1B···O6_$2iii | 0.89 (4) | 2.00 (4) | 2.845 (3) | 158 (3) |
O2—H2A···O1 | 0.91 (4) | 1.66 (4) | 2.558 (3) | 166 (3) |
O2—H2B···O3 | 0.80 (4) | 1.67 (4) | 2.458 (3) | 173 (4) |
O2—H2C···O23_$3iv | 0.96 (4) | 1.74 (4) | 2.653 (3) | 157 (3) |
O3—H3A···O22_$4v | 0.75 (3) | 1.98 (3) | 2.728 (3) | 176 (3) |
O3—H3A···O21_$4v | 0.75 (3) | 2.60 (3) | 3.055 (3) | 121 (3) |
O3—H3B···O23 | 0.91 (5) | 1.93 (5) | 2.814 (3) | 164 (4) |
Symmetry codes: (i) x, y−1, z; (ii) x−1/2, −y+3/2, z−1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) x+1/2, −y+3/2, z+1/2; (v) −x+3/2, y+1/2, −z+1/2. |
Oxidanium 6-Oxo-1
H,7
H-purin-9-ium dinitrate dihydrate (hx2_100k)
top
Crystal data top
H3O+·C5H5N4O+·2NO3−·2H2O | F(000) = 656 |
Mr = 316.21 | Dx = 1.735 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 10.9025 (4) Å | Cell parameters from 4172 reflections |
b = 10.1712 (3) Å | θ = 5.0–76.4° |
c = 11.3174 (4) Å | µ = 1.50 mm−1 |
β = 105.264 (4)° | T = 100 K |
V = 1210.73 (7) Å3 | Block, clear light colourless |
Z = 4 | 0.18 × 0.1 × 0.09 mm |
Data collection top
Agilent Technologies SuperNova four-circle diffractometer equipped with a
micro-focus sealed tube and an Eos CCD detector | 2185 reflections with I > 2σ(I) |
Detector resolution: 5.2195 pixels mm-1 | Rint = 0.040 |
ω scans | θmax = 77.2°, θmin = 5.0° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −13→13 |
Tmin = 0.836, Tmax = 1.000 | k = −12→12 |
10131 measured reflections | l = −13→14 |
2551 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | All H-atom parameters refined |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0594P)2 + 0.5449P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.031 |
2551 reflections | Δρmax = 0.46 e Å−3 |
238 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | |
Special details top
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. All crystal structures were determined using an Agilent
Technologies SuperNova four-circle diffractometer equipped with a micro-focus
sealed tube and an Eos CCD detector. The temperature was controlled with an
Oxford Cryosystems low-temperature nitrogen gas-flow device. For helium
measurements, a CRYOCOOL-LHe gas stream cooler was used. Unit-cell
determination, data reduction, and absorption correction were performed using
CrysAlis PRO Version 1.171.38.46 (Agilent Technologies, 2014). All structures
were solved and refined using ShelXT (Sheldrick, 2015b) with intrinsic phasing
and refined with ShelXL (Sheldrick, 2015a) with least-squares within
OLEX2
graphical environment (Dolomanov et al., 2009). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O6 | 0.29752 (12) | 0.22636 (12) | 0.13188 (12) | 0.0202 (3) | |
N1 | 0.46833 (14) | 0.24435 (15) | 0.30056 (14) | 0.0185 (3) | |
H1 | 0.478 (2) | 0.159 (3) | 0.308 (2) | 0.028 (6)* | |
N3 | 0.55947 (14) | 0.44366 (15) | 0.39068 (13) | 0.0187 (3) | |
N7 | 0.30462 (14) | 0.53273 (15) | 0.13876 (14) | 0.0173 (3) | |
H7 | 0.243 (2) | 0.517 (2) | 0.076 (2) | 0.015 (5)* | |
N9 | 0.44728 (14) | 0.63345 (14) | 0.28188 (14) | 0.0185 (3) | |
H9 | 0.492 (2) | 0.696 (3) | 0.328 (2) | 0.021 (6)* | |
C2 | 0.55504 (17) | 0.31492 (18) | 0.38501 (16) | 0.0192 (3) | |
H2 | 0.615 (2) | 0.267 (2) | 0.4425 (18) | 0.009 (5)* | |
C4 | 0.46717 (16) | 0.50076 (17) | 0.30101 (16) | 0.0170 (3) | |
C5 | 0.37700 (16) | 0.43719 (17) | 0.21119 (15) | 0.0165 (3) | |
C6 | 0.37245 (16) | 0.29647 (17) | 0.20514 (15) | 0.0173 (3) | |
C8 | 0.34903 (17) | 0.64895 (17) | 0.18356 (16) | 0.0182 (3) | |
H8 | 0.314 (2) | 0.726 (3) | 0.149 (2) | 0.020 (5)* | |
N11 | 0.55332 (14) | 0.92716 (15) | 0.39158 (13) | 0.0179 (3) | |
O12 | 0.61073 (12) | 1.02793 (13) | 0.44347 (12) | 0.0217 (3) | |
O11 | 0.46243 (13) | 0.93913 (13) | 0.29982 (12) | 0.0240 (3) | |
O13 | 0.58970 (13) | 0.81555 (13) | 0.43578 (12) | 0.0221 (3) | |
O1 | 0.78466 (13) | 0.54213 (13) | 0.55666 (12) | 0.0233 (3) | |
H1A | 0.801 (3) | 0.467 (3) | 0.594 (3) | 0.045 (8)* | |
H1B | 0.716 (3) | 0.524 (3) | 0.494 (3) | 0.047 (9)* | |
O2 | 0.96449 (13) | 0.64578 (13) | 0.48016 (13) | 0.0225 (3) | |
H2A | 0.896 (5) | 0.601 (5) | 0.511 (5) | 0.116 (18)* | |
H2B | 0.918 (4) | 0.723 (5) | 0.437 (4) | 0.087 (14)* | |
H2C | 1.038 (4) | 0.659 (4) | 0.554 (3) | 0.064 (11)* | |
O3 | 0.86387 (14) | 0.84073 (13) | 0.36986 (14) | 0.0271 (3) | |
H3A | 0.877 (3) | 0.927 (3) | 0.398 (3) | 0.046 (8)* | |
H3B | 0.802 (3) | 0.837 (3) | 0.314 (3) | 0.036 (7)* | |
N21 | 0.66682 (14) | 0.66028 (15) | 0.16339 (14) | 0.0192 (3) | |
O21 | 0.74039 (14) | 0.60155 (14) | 0.24818 (13) | 0.0268 (3) | |
O22 | 0.59449 (13) | 0.60015 (13) | 0.07509 (12) | 0.0232 (3) | |
O23 | 0.66063 (13) | 0.78614 (13) | 0.16482 (12) | 0.0233 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O6 | 0.0197 (6) | 0.0152 (5) | 0.0225 (6) | −0.0020 (4) | 0.0001 (5) | −0.0021 (5) |
N1 | 0.0193 (7) | 0.0140 (7) | 0.0197 (7) | 0.0005 (5) | 0.0010 (6) | 0.0016 (5) |
N3 | 0.0181 (7) | 0.0176 (7) | 0.0183 (7) | −0.0005 (5) | 0.0012 (5) | 0.0003 (5) |
N7 | 0.0162 (7) | 0.0150 (7) | 0.0185 (7) | 0.0012 (5) | 0.0003 (6) | 0.0004 (5) |
N9 | 0.0188 (7) | 0.0144 (7) | 0.0208 (7) | −0.0004 (5) | 0.0025 (6) | −0.0017 (5) |
C2 | 0.0187 (8) | 0.0181 (8) | 0.0188 (8) | 0.0005 (6) | 0.0015 (6) | 0.0008 (6) |
C4 | 0.0174 (8) | 0.0153 (8) | 0.0179 (7) | 0.0000 (6) | 0.0039 (6) | −0.0013 (6) |
C5 | 0.0155 (7) | 0.0151 (8) | 0.0178 (7) | −0.0001 (6) | 0.0023 (6) | −0.0001 (6) |
C6 | 0.0168 (8) | 0.0170 (8) | 0.0173 (7) | 0.0005 (6) | 0.0030 (6) | 0.0008 (6) |
C8 | 0.0177 (8) | 0.0150 (8) | 0.0210 (8) | 0.0025 (6) | 0.0036 (6) | 0.0009 (6) |
N11 | 0.0177 (7) | 0.0160 (7) | 0.0183 (7) | 0.0009 (5) | 0.0015 (5) | −0.0003 (5) |
O12 | 0.0212 (6) | 0.0146 (6) | 0.0249 (6) | −0.0023 (5) | −0.0016 (5) | −0.0009 (5) |
O11 | 0.0225 (6) | 0.0222 (6) | 0.0215 (6) | 0.0020 (5) | −0.0044 (5) | −0.0009 (5) |
O13 | 0.0250 (7) | 0.0136 (6) | 0.0241 (6) | 0.0016 (5) | −0.0002 (5) | 0.0010 (5) |
O1 | 0.0216 (6) | 0.0194 (6) | 0.0231 (6) | −0.0033 (5) | −0.0042 (5) | 0.0040 (5) |
O2 | 0.0209 (6) | 0.0173 (6) | 0.0258 (7) | −0.0004 (5) | −0.0002 (5) | 0.0009 (5) |
O3 | 0.0269 (7) | 0.0172 (6) | 0.0283 (7) | −0.0014 (5) | −0.0083 (6) | −0.0008 (5) |
N21 | 0.0172 (7) | 0.0171 (7) | 0.0213 (7) | −0.0010 (5) | 0.0017 (6) | −0.0012 (5) |
O21 | 0.0269 (7) | 0.0214 (6) | 0.0249 (7) | 0.0009 (5) | −0.0064 (5) | 0.0028 (5) |
O22 | 0.0234 (6) | 0.0185 (6) | 0.0226 (6) | −0.0021 (5) | −0.0029 (5) | −0.0027 (5) |
O23 | 0.0244 (7) | 0.0145 (6) | 0.0268 (6) | −0.0003 (5) | −0.0005 (5) | −0.0008 (5) |
Geometric parameters (Å, º) top
O6—C6 | 1.227 (2) | C8—H8 | 0.91 (3) |
N1—H1 | 0.87 (3) | N11—O12 | 1.262 (2) |
N1—C2 | 1.359 (2) | N11—O11 | 1.238 (2) |
N1—C6 | 1.395 (2) | N11—O13 | 1.262 (2) |
N3—C2 | 1.311 (2) | O1—H1A | 0.87 (4) |
N3—C4 | 1.357 (2) | O1—H1B | 0.90 (3) |
N7—H7 | 0.85 (3) | O2—H2A | 1.01 (6) |
N7—C5 | 1.378 (2) | O2—H2B | 0.99 (5) |
N7—C8 | 1.326 (2) | O2—H2C | 1.00 (4) |
N9—H9 | 0.88 (3) | O3—H2B | 1.46 (5) |
N9—C4 | 1.375 (2) | O3—H3A | 0.93 (3) |
N9—C8 | 1.335 (2) | O3—H3B | 0.79 (3) |
C2—H2 | 0.93 (2) | N21—O21 | 1.231 (2) |
C4—C5 | 1.375 (2) | N21—O22 | 1.257 (2) |
C5—C6 | 1.433 (2) | N21—O23 | 1.282 (2) |
| | | |
C2—N1—H1 | 114.1 (18) | O6—C6—N1 | 122.14 (16) |
C2—N1—C6 | 125.77 (16) | O6—C6—C5 | 128.39 (16) |
C6—N1—H1 | 120.1 (18) | N1—C6—C5 | 109.46 (15) |
C2—N3—C4 | 112.34 (15) | N7—C8—N9 | 110.20 (15) |
C5—N7—H7 | 124.6 (16) | N7—C8—H8 | 122.2 (15) |
C8—N7—H7 | 127.5 (16) | N9—C8—H8 | 127.6 (16) |
C8—N7—C5 | 107.87 (15) | O11—N11—O12 | 119.97 (15) |
C4—N9—H9 | 125.0 (17) | O11—N11—O13 | 121.31 (15) |
C8—N9—H9 | 127.2 (17) | O13—N11—O12 | 118.72 (14) |
C8—N9—C4 | 107.80 (15) | H1A—O1—H1B | 103 (3) |
N1—C2—H2 | 116.3 (13) | H2A—O2—H2B | 101 (4) |
N3—C2—N1 | 124.87 (16) | H2A—O2—H2C | 106 (4) |
N3—C2—H2 | 118.8 (13) | H2B—O2—H2C | 120 (3) |
N3—C4—N9 | 126.36 (16) | H2B—O3—H3A | 126 (3) |
N3—C4—C5 | 126.61 (16) | H2B—O3—H3B | 121 (3) |
N9—C4—C5 | 107.02 (15) | H3A—O3—H3B | 110 (3) |
N7—C5—C6 | 131.97 (16) | O21—N21—O22 | 121.82 (16) |
C4—C5—N7 | 107.10 (15) | O21—N21—O23 | 120.01 (15) |
C4—C5—C6 | 120.92 (16) | O22—N21—O23 | 118.15 (15) |
| | | |
N3—C4—C5—N7 | −178.82 (16) | C4—N3—C2—N1 | −0.5 (3) |
N3—C4—C5—C6 | 0.4 (3) | C4—N9—C8—N7 | 0.2 (2) |
N7—C5—C6—O6 | −1.8 (3) | C4—C5—C6—O6 | 179.17 (17) |
N7—C5—C6—N1 | 179.51 (17) | C4—C5—C6—N1 | 0.5 (2) |
N9—C4—C5—N7 | 0.39 (19) | C5—N7—C8—N9 | 0.1 (2) |
N9—C4—C5—C6 | 179.63 (15) | C6—N1—C2—N3 | 1.6 (3) |
C2—N1—C6—O6 | 179.79 (16) | C8—N7—C5—C4 | −0.30 (19) |
C2—N1—C6—C5 | −1.4 (2) | C8—N7—C5—C6 | −179.43 (18) |
C2—N3—C4—N9 | −179.51 (17) | C8—N9—C4—N3 | 178.87 (16) |
C2—N3—C4—C5 | −0.4 (3) | C8—N9—C4—C5 | −0.34 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O12_$5i | 0.87 (3) | 2.25 (3) | 2.924 (2) | 134 (2) |
N1—H1···O11_$5i | 0.87 (3) | 2.25 (3) | 3.105 (2) | 168 (2) |
N7—H7···O13_$1ii | 0.85 (3) | 2.61 (2) | 3.212 (2) | 129 (2) |
N7—H7···O12_$1ii | 0.85 (3) | 1.85 (3) | 2.697 (2) | 176 (2) |
N9—H9···O11 | 0.88 (3) | 2.51 (3) | 3.117 (2) | 127 (2) |
N9—H9···O13 | 0.88 (3) | 1.85 (3) | 2.730 (2) | 175 (2) |
C2—H2···O6_$2iii | 0.93 (2) | 2.51 (2) | 3.329 (2) | 146.6 (18) |
C2—H2···O12_$5i | 0.93 (2) | 2.43 (2) | 3.019 (2) | 121.3 (16) |
C8—H8···O1_$1ii | 0.91 (3) | 2.57 (3) | 3.449 (2) | 163 (2) |
O1—H1A···O6_$2iii | 0.87 (4) | 2.01 (4) | 2.8530 (18) | 161 (3) |
O1—H1B···N3 | 0.90 (3) | 1.98 (3) | 2.852 (2) | 163 (3) |
O2—H2A···O1 | 1.01 (6) | 1.56 (6) | 2.5687 (19) | 176 (5) |
O2—H2B···O3 | 0.99 (5) | 1.46 (5) | 2.4439 (19) | 173 (4) |
O2—H2C···O23_$3iv | 1.00 (4) | 1.67 (4) | 2.6584 (19) | 168 (4) |
O3—H3A···O22_$4v | 0.93 (3) | 1.80 (3) | 2.7217 (19) | 169 (3) |
O3—H3A···O21_$4v | 0.93 (3) | 2.53 (3) | 3.052 (2) | 116 (2) |
O3—H3B···O23 | 0.79 (3) | 2.03 (3) | 2.810 (2) | 167 (3) |
Symmetry codes: (i) x, y−1, z; (ii) x−1/2, −y+3/2, z−1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) x+1/2, −y+3/2, z+1/2; (v) −x+3/2, y+1/2, −z+1/2. |
Hydrogen bonds for Hx1.
The lengths
are colour coded according to the classification of Jeffrey (1997),
i.e. blue = weak, yellow = moderate
and red = strong. topD—H···A | D—H | H···A | D···A | D—H···A | D—H | H···A | D···A | D—H···A | D—H | H···A | D···A | D—H···A |
| 20 K | | | | 105 K | | | | 285 K | | | |
C2—H2···O12i | 0.95 | 2.42 | 3.017 (6) | 120.5 | 0.946 (14) | 2.394 (14) | 3.0131 (15) | 122.8 (10) | 0.97 (2) | 2.41 (2) | 3.043 (2) | 122.6 (17) |
C2—H2···O6iii | 0.95 | 2.62 | 3.476 (6) | 150.5 | 0.946 (14) | 2.637 (14) | 3.4750 (15) | 147.9 (11) | 0.97 (2) | 2.63 (2) | 3.480 (2) | 146.5 (17) |
C8—H8···O1ii | 0.98 (7) | 2.14 (7) | 3.112 (6) | 173 (5) | 1.022 (16) | 2.092 (16) | 3.1090 (16) | 173.4 (13) | 1.00 (3) | 2.12 (3) | 3.118 (2) | 174 (2) |
N1—H1···O11i | 0.88 | 2.14 | 3.015 (5) | 171.9 | 0.981 (14) | 2.050 (15) | 3.0235 (14) | 171.3 (12) | 0.94 (3) | 2.15 (3) | 3.083 (2) | 169 (3) |
N1—H1···O12i | 0.88 | 2.31 | 2.941 (5) | 128.9 | 0.981 (14) | 2.237 (14) | 2.9433 (13) | 127.9 (11) | 0.94 (3) | 2.23 (3) | 2.942 (2) | 132 (2) |
N7—H7···O12ii | 0.88 (6) | 1.84 (6) | 2.710 (5) | 174 (6) | 0.932 (16) | 1.780 (16) | 2.7090 (14) | 174.7 (16) | 0.95 (3) | 1.77 (3) | 2.723 (2) | 177 (3) |
N7—H7···O13ii | 0.88 (6) | 2.60 (6) | 3.209 (5) | 128 (5) | 0.932 (16) | 2.543 (16) | 3.2046 (13) | 128.2 (13) | 0.95 (3) | 2.55 (3) | 3.209 (2) | 127 (2) |
N9—H9···O11 | 0.85 (7) | 2.50 (6) | 3.096 (5) | 128 (5) | 0.861 (18) | 2.467 (18) | 3.0954 (13) | 130.5 (14) | 0.90 (3) | 2.38 (3) | 3.101 (2) | 137 (2) |
N9—H9···O13 | 0.85 (7) | 1.92 (7) | 2.772 (5) | 175 (6) | 0.861 (18) | 1.921 (18) | 2.7761 (14) | 171.7 (16) | 0.90 (3) | 1.93 (3) | 2.804 (2) | 164 (3) |
O1—H1A···O6iii | 0.79 (6) | 2.22 (6) | 2.988 (5) | 164 (5) | 0.866 (19) | 2.18 (2) | 2.9990 (13) | 158.3 (16) | 0.77 (4) | 2.31 (4) | 3.046 (2) | 158 (3) |
O1—H1B···N3 | 0.95 (8) | 2.06 (7) | 2.918 (5) | 150 (5) | 0.88 (2) | 2.06 (2) | 2.9187 (14) | 167.5 (16) | 0.89 (3) | 2.06 (3) | 2.936 (2) | 166 (2) |
Symmetry codes:
(i) x, y, z+1;
(ii) x-1/2, y+1/2 , -z+1/2;
(iii) x-1/2, y-1/2, -z+3/2. |
Hydrogen bonds for Hx2
The interactions are separated into two groups for easier comparison –
in the first group, there are interactions analogous to these found in
Hx1, and in the second group, those unique to Hx2. The lengths
are colour coded according to the classification of Jeffrey (1997),
i.e. blue = weak, yellow = moderate
and red = strong. topD—H···A | D—H | H···A | D···A | D—H···A | D—H | H···A | D···A | D—H···A |
| 20 K | | | | 100 K | | | |
C2—H2···O12i | 0.95 (3) | 2.40 (3) | 3.018 (3) | 122 (2) | 0.93 (2) | 2.43 (2) | 3.019 (2) | 121.3 (16) |
C2—H2···O6iii | 0.95 (3) | 2.50 (3) | 3.327 (3) | 145 (2) | 0.93 (2) | 2.51 (2) | 3.329 (2) | 146.6 (18) |
C8—H8···O1ii | 0.97 (3) | 2.50 (3) | 3.449 (3) | 166 (2) | 0.91 (3) | 2.57 (3) | 3.449 (2) | 163 (2) |
N1—H1···O11i | 0.98 (3) | 2.13 (3) | 3.099 (3) | 171 (3) | 0.87 (3) | 2.25 (3) | 3.105 (2) | 168 (2) |
N1—H1···O12i | 0.98 (3) | 2.23 (3) | 2.924 (3) | 127 (3) | 0.87 (3) | 2.25 (3) | 2.924 (2) | 134 (2) |
N7—H7···O12ii | 0.98 (4) | 1.73 (4) | 2.695 (3) | 167 (3) | 0.85 (3) | 1.85 (3) | 2.697 (2) | 176 (2) |
N7—H7···O13ii | 0.98 (4) | 2.45 (4) | 3.208 (3) | 133 (3) | 0.85 (3) | 2.61 (2) | 3.212 (2) | 129 (2) |
N9—H9···O11 | 0.88 (3) | 2.49 (3) | 3.121 (3) | 129 (2) | 0.88 (3) | 2.51 (3) | 3.117 (2) | 127 (2) |
N9—H9···O13 | 0.88 (3) | 1.85 (3) | 2.731 (3) | 173 (3) | 0.88 (3) | 1.85 (3) | 2.730 (2) | 175 (2) |
O1—H1A···O6iii | 0.89 (4) | 2.00 (4) | 2.845 (3) | 158 (3) | 0.87 (4) | 2.01 (4) | 2.8530 (18) | 161 (3) |
O1—H1B···N3 | 0.87 (5) | 2.03 (5) | 2.853 (3) | 156 (4) | 0.90 (3) | 1.98 (3) | 2.852 (2) | 163 (3) |
O2—H2A···O1 | 0.91 (4) | 1.66 (4) | 2.558 (3) | 166 (3) | 1.01 (6) | 1.56 (6) | 2.5687 (19) | 176 (5) |
O2—H2B···O3 | 0.80 (4) | 1.67 (4) | 2.458 (3) | 173 (4) | 0.99 (5) | 1.46 (5) | 2.4439 (19) | 173 (4) |
O2—H2C···O23iv | 0.96 (4) | 1.74 (4) | 2.653 (3) | 157 (3) | 1.00 (4) | 1.67 (4) | 2.6584 (19) | 168 (4) |
O3—H3A···O21v | 0.75 (3) | 1.98 (3) | 2.728 (3) | 176 (3) | 0.93 (3) | 2.53 (3) | 3.052 (2) | 116 (2) |
O3—H3A···O22v | 0.75 (3) | 2.60 (3) | 3.055 (3) | 121 (3) | 0.93 (3) | 1.80 (3) | 2.7217 (19) | 169 (3) |
O3—H3B···O23 | 0.91 (5) | 1.93 (5) | 2.814 (3) | 164 (4) | 0.79 (3) | 2.03 (3) | 2.810 (2) | 167 (3) |
Symmetry codes: (i) x, y-1, z;
(ii) x-1/2, -y+3/2, z-1/2;
(iii) x+1/2, -y+3/2, z+1/2;
(iv) x+1/2, -y+3/2, z+1/2;
(v) -x+3/2, y+1/2, -z+1/2. |