Download citation
Download citation
link to html
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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619008702/qp3027sup1.cif
Contains datablocks global, hx1_105k, hx1_285k, hx2_20k, hx2_100k, hx1_20k

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619008702/qp3027hx1_20ksup2.hkl
Contains datablock hx1_20k

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619008702/qp3027hx1_105ksup3.hkl
Contains datablock hx1_105k

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619008702/qp3027hx1_285ksup4.hkl
Contains datablock hx1_285k

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619008702/qp3027hx2_20ksup5.hkl
Contains datablock hx2_20k

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619008702/qp3027hx2_100ksup6.hkl
Contains datablock hx2_100k

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619008702/qp3027hx1sup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619008702/qp3027hx2sup8.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619008702/qp3027sup9.pdf
Addition figures: cell images and fingerprint plots

CCDC references: 1901717; 1901719; 1901718; 1901720; 1901716

Computing details top

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-1H,7H-purin-9-ium nitrate monohydrate (hx1_20k) top
Crystal data top
C5H5N4O+·NO3·H2OF(000) = 448
Mr = 217.16Dx = 1.720 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.1156 (18) ÅCell parameters from 1835 reflections
b = 13.754 (2) Åθ = 2.9–27.5°
c = 10.0367 (19) ŵ = 0.15 mm1
β = 96.52 (2)°T = 20 K
V = 838.8 (3) Å3Block, clear light colourless
Z = 40.19 × 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-1Rint = 0.252
ω scansθmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
h = 88
Tmin = 0.646, Tmax = 1.000k = 1717
9106 measured reflectionsl = 1312
3467 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.094H 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 reflectionsΔρmax = 0.76 e Å3
157 parametersΔρmin = 0.72 e Å3
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
xyzUiso*/Ueq
O60.2467 (6)0.7924 (2)0.7755 (3)0.0121 (9)
N10.2466 (7)0.6260 (3)0.7530 (4)0.0099 (9)
H10.2434610.6195120.8399710.012*
N30.2530 (7)0.5396 (3)0.5492 (4)0.0099 (9)
N70.2566 (7)0.7888 (3)0.4645 (4)0.0098 (9)
N90.2621 (7)0.6502 (3)0.3607 (4)0.0097 (9)
C20.2489 (8)0.5429 (4)0.6784 (5)0.0117 (11)
H20.2474850.4826610.7247200.014*
C40.2563 (8)0.6294 (3)0.4937 (5)0.0095 (10)
C50.2529 (8)0.7169 (3)0.5597 (5)0.0107 (11)
C60.2488 (8)0.7207 (3)0.7015 (5)0.0081 (10)
C80.2626 (8)0.7470 (4)0.3453 (5)0.0104 (11)
N110.2564 (7)0.5331 (3)0.0680 (4)0.0100 (9)
O110.2573 (6)0.6237 (2)0.0541 (3)0.0133 (9)
O120.2451 (6)0.4791 (2)0.0342 (3)0.0126 (9)
O130.2668 (6)0.4961 (2)0.1831 (3)0.0114 (8)
O10.2437 (6)0.3444 (3)0.4349 (4)0.0122 (8)
H1A0.269 (11)0.412 (6)0.443 (6)0.04 (2)*
H80.261 (11)0.783 (5)0.261 (7)0.027 (17)*
H1B0.237 (9)0.320 (4)0.506 (6)0.007 (14)*
H70.263 (10)0.851 (5)0.484 (6)0.027 (17)*
H90.263 (11)0.605 (5)0.302 (7)0.026 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O60.0139 (19)0.0088 (17)0.0130 (19)0.0020 (14)0.0012 (15)0.0019 (13)
N10.013 (2)0.007 (2)0.0094 (18)0.0004 (16)0.0017 (16)0.0008 (16)
N30.011 (2)0.0064 (18)0.012 (2)0.0001 (16)0.0000 (17)0.0004 (16)
N70.010 (2)0.0055 (18)0.013 (2)0.0018 (16)0.0024 (17)0.0009 (15)
N90.012 (2)0.0049 (19)0.012 (2)0.0003 (16)0.0032 (17)0.0006 (16)
C20.009 (3)0.007 (2)0.018 (3)0.0002 (18)0.004 (2)0.0002 (19)
C40.008 (3)0.010 (2)0.010 (2)0.0019 (19)0.003 (2)0.0022 (17)
C50.009 (2)0.007 (2)0.015 (3)0.0009 (19)0.002 (2)0.0001 (18)
C60.005 (2)0.010 (2)0.009 (2)0.0005 (17)0.0018 (19)0.0003 (17)
C80.007 (3)0.010 (2)0.013 (2)0.0015 (18)0.0037 (19)0.0009 (19)
N110.010 (2)0.0081 (19)0.011 (2)0.0003 (17)0.0027 (17)0.0014 (15)
O110.021 (2)0.0043 (16)0.0146 (18)0.0005 (15)0.0004 (15)0.0024 (13)
O120.019 (2)0.0091 (16)0.0093 (18)0.0024 (16)0.0014 (16)0.0021 (13)
O130.0194 (19)0.0092 (17)0.0056 (18)0.0016 (14)0.0009 (14)0.0020 (13)
O10.016 (2)0.0094 (18)0.0106 (18)0.0009 (15)0.0013 (15)0.0024 (14)
Geometric parameters (Å, º) top
O6—C61.235 (6)N9—H90.85 (7)
N1—H10.8800C2—H20.9500
N1—C21.367 (6)C4—C51.375 (6)
N1—C61.403 (6)C5—C61.427 (7)
N3—C21.301 (6)C8—H80.98 (6)
N3—C41.355 (6)N11—O111.254 (5)
N7—C51.377 (6)N11—O121.262 (5)
N7—C81.332 (7)N11—O131.257 (5)
N7—H70.88 (6)O1—H1A0.95 (8)
N9—C41.370 (6)O1—H1B0.79 (6)
N9—C81.340 (6)
C2—N1—H1117.5N9—C4—C5106.8 (4)
C2—N1—C6125.0 (4)N7—C5—C6131.9 (4)
C6—N1—H1117.5C4—C5—N7107.0 (4)
C2—N3—C4112.4 (4)C4—C5—C6121.0 (4)
C5—N7—H7124 (4)O6—C6—N1121.3 (4)
C8—N7—C5108.5 (4)O6—C6—C5129.2 (4)
C8—N7—H7128 (4)N1—C6—C5109.6 (4)
C4—N9—H9122 (4)N7—C8—N9109.0 (4)
C8—N9—C4108.7 (4)N7—C8—H8124 (4)
C8—N9—H9130 (4)N9—C8—H8127 (4)
N1—C2—H2117.4O11—N11—O12119.6 (4)
N3—C2—N1125.2 (5)O11—N11—O13120.3 (4)
N3—C2—H2117.4O13—N11—O12120.1 (4)
N3—C4—N9126.5 (4)H1A—O1—H1B111 (5)
N3—C4—C5126.7 (5)
N3—C4—C5—N7179.5 (5)C4—N3—C2—N10.4 (7)
N3—C4—C5—C61.1 (8)C4—N9—C8—N70.2 (6)
N7—C5—C6—O60.3 (10)C4—C5—C6—O6179.5 (5)
N7—C5—C6—N1179.9 (5)C4—C5—C6—N10.7 (7)
N9—C4—C5—N70.0 (6)C5—N7—C8—N90.2 (6)
N9—C4—C5—C6179.4 (5)C6—N1—C2—N30.2 (8)
C2—N1—C6—O6179.9 (5)C8—N7—C5—C40.1 (6)
C2—N1—C6—C50.3 (7)C8—N7—C5—C6179.1 (5)
C2—N3—C4—N9179.6 (5)C8—N9—C4—N3179.7 (5)
C2—N3—C4—C50.9 (8)C8—N9—C4—C50.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O12_$1i0.882.312.941 (5)129
N1—H1···O11_$1i0.882.143.015 (5)172
O1—H1A···N30.95 (8)2.06 (7)2.918 (5)150 (6)
N7—H7···O13_$2ii0.88 (6)2.60 (7)3.209 (5)128 (5)
N7—H7···O12_$2ii0.88 (6)1.84 (6)2.710 (5)174 (6)
C2—H2···O12_$1i0.952.423.017 (6)121
C2—H2···O6_$3iii0.952.623.476 (6)151
N9—H9···O110.85 (7)2.50 (6)3.096 (5)128 (5)
N9—H9···O130.85 (7)1.92 (7)2.772 (5)175 (6)
C8—H8···O1_$2ii0.98 (6)2.14 (7)3.112 (6)173 (5)
O1—H1B···O6_$3iii0.79 (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, y1/2, z+3/2.
6-Oxo-1H,7H-purin-9-ium nitrate monohydrate (hx1_105k) top
Crystal data top
C5H5N4O+·NO3·H2OF(000) = 448
Mr = 217.16Dx = 1.712 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.1381 (4) ÅCell parameters from 3258 reflections
b = 13.7467 (8) Åθ = 3.6–31.7°
c = 10.0349 (5) ŵ = 0.15 mm1
β = 95.813 (5)°T = 105 K
V = 842.38 (9) Å3Block, clear light colourless
Z = 40.19 × 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-1Rint = 0.041
ω scansθmax = 32.5°, θmin = 2.5°
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2015)
h = 89
Tmin = 0.978, Tmax = 0.989k = 2020
25288 measured reflectionsl = 1514
5823 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Only 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 reflectionsΔρmax = 0.40 e Å3
163 parametersΔρmin = 0.33 e Å3
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
xyzUiso*/Ueq
O60.24738 (14)0.79173 (6)0.77511 (8)0.0188 (2)
N10.24700 (17)0.62535 (7)0.75254 (10)0.0161 (2)
H10.246 (2)0.6176 (10)0.8496 (15)0.019*
N30.25332 (17)0.53913 (7)0.54892 (10)0.0154 (2)
N70.25577 (17)0.78846 (7)0.46481 (10)0.0152 (2)
H70.255 (2)0.8550 (12)0.4829 (17)0.036 (5)*
N90.26142 (17)0.64979 (8)0.36095 (10)0.0155 (2)
H90.264 (3)0.6062 (12)0.2995 (18)0.035 (5)*
C20.2488 (2)0.54234 (9)0.67932 (12)0.0165 (3)
H20.249 (2)0.4836 (10)0.7283 (14)0.020*
C40.25523 (18)0.62932 (9)0.49445 (11)0.0137 (2)
C50.25157 (19)0.71626 (8)0.55981 (12)0.0136 (2)
C60.24789 (19)0.72009 (8)0.70160 (12)0.0145 (2)
C80.2611 (2)0.74652 (9)0.34573 (13)0.0164 (2)
H80.262 (2)0.7835 (11)0.2575 (16)0.030 (4)*
N110.25550 (18)0.53325 (8)0.06857 (10)0.0168 (2)
O110.25554 (16)0.62316 (6)0.05431 (9)0.0229 (2)
O120.24570 (16)0.47903 (6)0.03341 (8)0.0209 (2)
O130.26426 (16)0.49552 (6)0.18263 (8)0.0217 (2)
O10.24421 (16)0.34388 (7)0.43422 (10)0.0190 (2)
H1A0.246 (3)0.3130 (13)0.510 (2)0.042 (5)*
H1B0.245 (3)0.4056 (15)0.4560 (17)0.044 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O60.0271 (5)0.0137 (4)0.0157 (4)0.0002 (4)0.0028 (3)0.0034 (3)
N10.0228 (5)0.0133 (5)0.0125 (4)0.0006 (4)0.0024 (4)0.0010 (4)
N30.0199 (5)0.0110 (4)0.0154 (5)0.0000 (4)0.0018 (4)0.0001 (4)
N70.0194 (5)0.0118 (4)0.0146 (5)0.0006 (4)0.0023 (4)0.0007 (4)
N90.0194 (5)0.0146 (5)0.0127 (5)0.0002 (4)0.0025 (4)0.0016 (4)
C20.0209 (7)0.0114 (5)0.0172 (6)0.0002 (5)0.0015 (5)0.0001 (5)
C40.0140 (6)0.0146 (5)0.0124 (5)0.0001 (5)0.0015 (4)0.0006 (4)
C50.0147 (5)0.0123 (5)0.0139 (5)0.0003 (5)0.0020 (4)0.0007 (4)
C60.0154 (6)0.0130 (5)0.0150 (5)0.0005 (5)0.0017 (4)0.0003 (5)
C80.0176 (6)0.0166 (6)0.0153 (6)0.0003 (5)0.0030 (4)0.0005 (5)
N110.0237 (5)0.0139 (5)0.0128 (5)0.0012 (4)0.0019 (4)0.0004 (4)
O110.0399 (5)0.0096 (4)0.0192 (5)0.0005 (4)0.0032 (4)0.0010 (4)
O120.0361 (5)0.0150 (4)0.0119 (4)0.0003 (4)0.0034 (4)0.0021 (3)
O130.0376 (5)0.0169 (4)0.0106 (4)0.0016 (4)0.0027 (4)0.0025 (4)
O10.0263 (5)0.0137 (4)0.0173 (4)0.0007 (4)0.0030 (4)0.0011 (4)
Geometric parameters (Å, º) top
O6—C61.2307 (14)N9—C81.3384 (16)
N1—H10.981 (14)C2—H20.946 (14)
N1—C21.3579 (16)C4—C51.3646 (16)
N1—C61.3993 (15)C5—C61.4263 (17)
N3—C21.3124 (16)C8—H81.022 (16)
N3—C41.3554 (14)N11—O111.2443 (13)
N7—H70.932 (16)N11—O121.2625 (12)
N7—C51.3782 (15)N11—O131.2527 (12)
N7—C81.3301 (16)O1—H1A0.866 (19)
N9—H90.861 (18)O1—H1B0.88 (2)
N9—C41.3732 (15)
C2—N1—H1116.6 (9)C5—C4—N9107.02 (11)
C2—N1—C6125.73 (11)N7—C5—C6131.82 (11)
C6—N1—H1117.7 (9)C4—C5—N7107.21 (10)
C2—N3—C4111.92 (10)C4—C5—C6120.96 (11)
C5—N7—H7124.8 (10)O6—C6—N1121.70 (11)
C8—N7—H7127.0 (10)O6—C6—C5128.96 (11)
C8—N7—C5108.25 (10)N1—C6—C5109.34 (10)
C4—N9—H9124.1 (11)N7—C8—N9109.14 (11)
C8—N9—H9127.5 (11)N7—C8—H8124.5 (9)
C8—N9—C4108.37 (10)N9—C8—H8126.3 (9)
N1—C2—H2115.9 (8)O11—N11—O12119.58 (10)
N3—C2—N1124.74 (11)O11—N11—O13121.06 (10)
N3—C2—H2119.4 (8)O13—N11—O12119.36 (10)
N3—C4—N9125.67 (11)H1A—O1—H1B105.0 (15)
N3—C4—C5127.30 (11)
N3—C4—C5—N7179.93 (12)C4—N3—C2—N10.20 (17)
N3—C4—C5—C60.8 (2)C4—N9—C8—N70.22 (14)
N7—C5—C6—O60.1 (2)C4—C5—C6—O6178.90 (13)
N7—C5—C6—N1179.29 (13)C4—C5—C6—N10.47 (16)
N9—C4—C5—N70.05 (13)C5—N7—C8—N90.25 (15)
N9—C4—C5—C6179.13 (11)C6—N1—C2—N30.5 (2)
C2—N1—C6—O6179.56 (12)C8—N7—C5—C40.18 (14)
C2—N1—C6—C50.13 (16)C8—N7—C5—C6179.12 (13)
C2—N3—C4—N9179.50 (11)C8—N9—C4—N3179.92 (12)
C2—N3—C4—C50.47 (18)C8—N9—C4—C50.10 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O12_$1i0.98 (1)2.24 (1)2.9433 (13)128 (1)
N1—H1···O11_$1i0.98 (1)2.05 (2)3.0235 (14)171 (1)
N7—H7···O12_$2ii0.932 (16)1.780 (16)2.7090 (14)174.7 (16)
N7—H7···O13_$2ii0.932 (16)2.543 (16)3.2046 (13)128.2 (13)
N9—H9···O110.861 (18)2.467 (18)3.0954 (13)130.5 (14)
N9—H9···O130.861 (18)1.921 (18)2.7761 (14)171.7 (16)
C2—H2···O6_$3iii0.95 (1)2.64 (1)3.4750 (15)148 (1)
C2—H2···O12_$1i0.95 (1)2.39 (1)3.0131 (15)123 (1)
C8—H8···O1_$2ii1.022 (16)2.092 (16)3.1090 (16)173.4 (13)
O1—H1A···O6_$3iii0.866 (19)2.18 (2)2.9990 (13)158.3 (16)
O1—H1B···N30.88 (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, y1/2, z+3/2.
6-Oxo-1H,7H-purin-9-ium nitrate monohydrate (hx1_285k) top
Crystal data top
C5H5N4O+·NO3·H2ODx = 1.668 Mg m3
Mr = 217.16Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PmnbCell parameters from 4619 reflections
a = 6.241 (4) Åθ = 2.5–31.7°
b = 13.726 (3) ŵ = 0.15 mm1
c = 10.095 (5) ÅT = 285 K
V = 864.8 (7) Å3Block, clear light colourless
Z = 40.18 × 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-1Rint = 0.036
ω scansθmax = 32.4°, θmin = 2.5°
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2015)
h = 99
Tmin = 0.796, Tmax = 1.000k = 2020
16933 measured reflectionsl = 1515
1636 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042All 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 reflectionsΔρmax = 0.23 e Å3
112 parametersΔρmin = 0.24 e Å3
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
xyzUiso*/Ueq
O60.2500000.21060 (10)0.22449 (14)0.0522 (4)
N10.2500000.37669 (11)0.24813 (16)0.0434 (4)
H10.2500000.386 (2)0.156 (3)0.074 (8)*
N30.2500000.46225 (11)0.45096 (15)0.0425 (4)
N70.2500000.21261 (11)0.53303 (15)0.0400 (3)
H70.2500000.145 (2)0.514 (3)0.069 (8)*
N90.2500000.35077 (13)0.63774 (15)0.0428 (4)
H90.2500000.391 (2)0.707 (3)0.071 (8)*
C20.2500000.45935 (14)0.32126 (19)0.0450 (4)
H20.2500000.5191 (17)0.270 (2)0.048 (6)*
C40.2500000.37185 (12)0.50481 (17)0.0355 (3)
C50.2500000.28503 (12)0.43899 (16)0.0355 (3)
C60.2500000.28188 (13)0.29782 (17)0.0384 (4)
C80.2500000.25417 (15)0.6517 (2)0.0449 (4)
H80.2500000.2187 (18)0.738 (3)0.057 (7)*
N110.2500000.46700 (11)0.93010 (14)0.0453 (4)
O120.2500000.51997 (10)1.03138 (13)0.0564 (4)
O110.2500000.37762 (10)0.94277 (15)0.0646 (5)
O130.2500000.50589 (10)0.81851 (13)0.0588 (4)
O10.2500000.65786 (11)0.56856 (16)0.0500 (4)
H1A0.2500000.686 (2)0.503 (4)0.081 (10)*
H1B0.2500000.595 (2)0.547 (3)0.064 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O60.0829 (10)0.0376 (7)0.0360 (7)0.0000.0000.0079 (5)
N10.0636 (9)0.0355 (8)0.0313 (7)0.0000.0000.0021 (6)
N30.0584 (9)0.0295 (7)0.0397 (7)0.0000.0000.0019 (6)
N70.0526 (9)0.0313 (7)0.0362 (7)0.0000.0000.0039 (6)
N90.0557 (9)0.0421 (8)0.0306 (7)0.0000.0000.0037 (6)
C20.0623 (11)0.0315 (8)0.0412 (9)0.0000.0000.0027 (7)
C40.0431 (8)0.0329 (8)0.0305 (7)0.0000.0000.0030 (6)
C50.0434 (8)0.0303 (7)0.0327 (8)0.0000.0000.0009 (6)
C60.0504 (9)0.0318 (7)0.0329 (8)0.0000.0000.0007 (6)
C80.0547 (10)0.0465 (10)0.0336 (8)0.0000.0000.0033 (8)
N110.0728 (11)0.0318 (7)0.0312 (7)0.0000.0000.0014 (6)
O120.1010 (12)0.0373 (7)0.0309 (6)0.0000.0000.0033 (5)
O110.1153 (15)0.0292 (7)0.0494 (8)0.0000.0000.0021 (6)
O130.1059 (12)0.0421 (8)0.0285 (6)0.0000.0000.0029 (5)
O10.0705 (10)0.0348 (7)0.0448 (8)0.0000.0000.0036 (6)
Geometric parameters (Å, º) top
O6—C61.227 (2)N9—C81.333 (3)
N1—H10.94 (3)C2—H20.97 (2)
N1—C21.354 (2)C4—C51.364 (2)
N1—C61.395 (2)C5—C61.426 (3)
N3—C21.310 (2)C8—H81.00 (3)
N3—C41.355 (2)N11—O121.2546 (19)
N7—H70.95 (3)N11—O111.233 (2)
N7—C51.375 (2)N11—O131.247 (2)
N7—C81.327 (3)O1—H1A0.77 (4)
N9—H90.90 (3)O1—H1B0.89 (3)
N9—C41.373 (2)
C2—N1—H1115.0 (18)C5—C4—N9106.98 (15)
C2—N1—C6125.87 (17)N7—C5—C6131.95 (16)
C6—N1—H1119.1 (18)C4—C5—N7107.17 (15)
C2—N3—C4111.92 (15)C4—C5—C6120.88 (16)
C5—N7—H7124.6 (18)O6—C6—N1121.81 (17)
C8—N7—H7127.2 (18)O6—C6—C5128.85 (17)
C8—N7—C5108.23 (16)N1—C6—C5109.34 (15)
C4—N9—H9129.4 (18)N7—C8—N9109.39 (17)
C8—N9—H9122.4 (18)N7—C8—H8125.3 (15)
C8—N9—C4108.23 (15)N9—C8—H8125.4 (15)
N1—C2—H2114.7 (13)O11—N11—O12119.46 (15)
N3—C2—N1124.79 (17)O11—N11—O13121.30 (16)
N3—C2—H2120.5 (13)O13—N11—O12119.23 (16)
N3—C4—N9125.82 (15)H1A—O1—H1B106 (3)
N3—C4—C5127.19 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O12_$1i0.94 (3)2.22 (3)2.942 (2)132 (2)
N1—H1···O11_$1i0.94 (3)2.15 (3)3.083 (3)169 (3)
N7—H7···O13_$2ii0.95 (3)2.55 (3)3.209 (2)127 (2)
N7—H7···O12_$2ii0.95 (3)1.77 (3)2.723 (2)177 (3)
N9—H9···O110.90 (3)2.38 (3)3.101 (3)137 (2)
N9—H9···O130.90 (3)1.93 (3)2.804 (2)164 (3)
C2—H2···O6_$3iii0.97 (2)2.63 (2)3.480 (2)147 (2)
C2—H2···O6_$3iii0.97 (2)2.63 (2)3.480 (2)147 (2)
C8—H8···O1_$2ii1.00 (3)2.13 (3)3.118 (3)174 (2)
O1—H1B···N30.89 (3)2.06 (3)2.936 (2)166 (2)
Symmetry codes: (i) x, y, z1; (ii) x+1/2, y1/2, z+3/2; (iii) x+1/2, y+1/2, z+1/2.
Oxidanium 6-Oxo-1H,7H-purin-9-ium dinitrate dihydrate (hx2_20k) top
Crystal data top
H3O+·C5H5N4O+·2NO3·2H2OF(000) = 656
Mr = 316.21Dx = 1.745 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.8485 (8) ÅCell parameters from 1478 reflections
b = 10.1717 (6) Åθ = 2.7–27.5°
c = 11.2851 (11) ŵ = 0.17 mm1
β = 104.812 (9)°T = 20 K
V = 1203.91 (17) Å3Block, clear light colourless
Z = 40.18 × 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-1Rint = 0.041
ω scansθmax = 28.2°, θmin = 2.3°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
h = 1014
Tmin = 0.683, Tmax = 1.000k = 1013
4511 measured reflectionsl = 1412
2640 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050All 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 reflectionsΔρmax = 0.35 e Å3
238 parametersΔρmin = 0.33 e Å3
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
xyzUiso*/Ueq
O60.29687 (15)0.22634 (16)0.13091 (16)0.0116 (4)
N10.46780 (19)0.2440 (2)0.30005 (19)0.0106 (5)
H10.476 (3)0.148 (3)0.303 (3)0.032 (9)*
N30.55907 (19)0.44304 (19)0.3903 (2)0.0108 (5)
N70.30425 (19)0.5334 (2)0.1377 (2)0.0101 (4)
H70.231 (4)0.525 (4)0.066 (4)0.051 (11)*
N90.44720 (19)0.6333 (2)0.2815 (2)0.0098 (4)
H90.489 (3)0.698 (3)0.328 (3)0.019 (8)*
C20.5546 (2)0.3149 (2)0.3847 (2)0.0106 (5)
H20.614 (3)0.264 (3)0.444 (3)0.015 (7)*
C40.4667 (2)0.5003 (2)0.3000 (2)0.0095 (5)
C50.3770 (2)0.4369 (2)0.2101 (2)0.0100 (5)
C60.3720 (2)0.2974 (2)0.2042 (2)0.0100 (5)
C80.3490 (2)0.6495 (2)0.1828 (2)0.0100 (5)
H80.316 (2)0.734 (3)0.150 (2)0.007 (6)*
N110.55299 (19)0.92711 (19)0.3917 (2)0.0107 (5)
O120.61072 (16)1.02817 (16)0.44319 (16)0.0120 (4)
O110.46190 (16)0.93936 (17)0.29922 (16)0.0136 (4)
O130.58955 (16)0.81559 (16)0.43504 (16)0.0122 (4)
O10.78417 (18)0.54153 (19)0.55631 (18)0.0142 (4)
H1A0.721 (4)0.529 (4)0.492 (4)0.067 (14)*
H1B0.807 (3)0.464 (4)0.593 (3)0.035 (10)*
O20.96465 (18)0.64482 (19)0.47990 (18)0.0124 (4)
H2A0.905 (4)0.596 (3)0.504 (3)0.040 (10)*
H2B0.927 (4)0.705 (4)0.442 (4)0.056 (13)*
H2C1.041 (4)0.646 (3)0.545 (4)0.047 (11)*
O30.86372 (19)0.84115 (19)0.36947 (19)0.0152 (4)
H3A0.876 (3)0.912 (3)0.388 (3)0.005 (7)*
H3B0.795 (4)0.841 (4)0.303 (4)0.066 (14)*
N210.66662 (19)0.6611 (2)0.1634 (2)0.0112 (5)
O210.73986 (16)0.60242 (17)0.24839 (16)0.0143 (4)
O220.59503 (16)0.60095 (17)0.07416 (16)0.0136 (4)
O230.66012 (16)0.78801 (16)0.16425 (16)0.0129 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O60.0087 (8)0.0096 (8)0.0154 (9)0.0024 (7)0.0008 (7)0.0030 (7)
N10.0076 (10)0.0099 (10)0.0141 (11)0.0000 (8)0.0023 (8)0.0015 (8)
N30.0079 (10)0.0107 (10)0.0145 (11)0.0003 (8)0.0040 (9)0.0002 (8)
N70.0063 (10)0.0105 (10)0.0128 (11)0.0006 (8)0.0012 (8)0.0009 (8)
N90.0097 (10)0.0068 (10)0.0130 (11)0.0008 (8)0.0033 (9)0.0013 (8)
C20.0054 (11)0.0135 (12)0.0135 (13)0.0003 (10)0.0036 (10)0.0010 (10)
C40.0084 (11)0.0077 (11)0.0137 (12)0.0014 (9)0.0051 (9)0.0010 (9)
C50.0077 (12)0.0093 (12)0.0135 (12)0.0009 (9)0.0037 (10)0.0007 (10)
C60.0062 (11)0.0133 (12)0.0114 (12)0.0015 (10)0.0042 (9)0.0011 (10)
C80.0059 (11)0.0120 (12)0.0126 (13)0.0013 (10)0.0031 (10)0.0008 (10)
N110.0073 (10)0.0105 (10)0.0149 (11)0.0008 (8)0.0040 (9)0.0004 (8)
O120.0098 (8)0.0093 (8)0.0160 (9)0.0036 (7)0.0013 (7)0.0026 (7)
O110.0095 (9)0.0155 (9)0.0132 (9)0.0008 (7)0.0019 (7)0.0008 (7)
O130.0123 (9)0.0084 (8)0.0148 (9)0.0019 (7)0.0011 (7)0.0018 (7)
O10.0109 (9)0.0137 (9)0.0157 (10)0.0006 (8)0.0010 (8)0.0028 (8)
O20.0090 (9)0.0111 (9)0.0161 (10)0.0010 (8)0.0013 (8)0.0027 (8)
O30.0148 (10)0.0079 (10)0.0197 (11)0.0017 (8)0.0016 (8)0.0012 (8)
N210.0081 (10)0.0095 (10)0.0167 (11)0.0024 (8)0.0044 (9)0.0008 (9)
O210.0104 (9)0.0133 (9)0.0159 (10)0.0006 (7)0.0028 (7)0.0033 (8)
O220.0114 (9)0.0125 (9)0.0148 (10)0.0021 (7)0.0007 (7)0.0034 (7)
O230.0103 (9)0.0092 (9)0.0175 (9)0.0015 (7)0.0007 (7)0.0012 (7)
Geometric parameters (Å, º) top
O6—C61.235 (3)C8—H80.97 (3)
N1—H10.98 (3)N11—O121.265 (3)
N1—C21.364 (3)N11—O111.247 (3)
N1—C61.404 (3)N11—O131.259 (3)
N3—C21.305 (3)O1—H1A0.87 (5)
N3—C41.364 (3)O1—H1B0.89 (4)
N7—H70.98 (4)O2—H2A0.91 (4)
N7—C51.387 (3)O2—H2B0.80 (4)
N7—C81.329 (3)O2—H2C0.96 (4)
N9—H90.88 (3)O3—H3A0.75 (3)
N9—C41.377 (3)O3—H3B0.91 (5)
N9—C81.340 (3)N21—O211.232 (3)
C2—H20.95 (3)N21—O221.262 (3)
C4—C51.374 (3)N21—O231.293 (3)
C5—C61.421 (3)
C2—N1—H1117.6 (19)C4—C5—C6121.0 (2)
C2—N1—C6125.3 (2)O6—C6—N1121.4 (2)
C6—N1—H1117 (2)O6—C6—C5128.8 (2)
C2—N3—C4112.3 (2)N1—C6—C5109.8 (2)
C5—N7—H7130 (2)N7—C8—N9110.1 (2)
C8—N7—H7122 (2)N7—C8—H8125.6 (16)
C8—N7—C5107.8 (2)N9—C8—H8124.3 (16)
C4—N9—H9126.9 (19)O11—N11—O12119.8 (2)
C8—N9—H9125.2 (19)O11—N11—O13121.3 (2)
C8—N9—C4107.8 (2)O13—N11—O12119.0 (2)
N1—C2—H2115.0 (17)H1A—O1—H1B109 (4)
N3—C2—N1124.9 (2)H2A—O2—H2B106 (3)
N3—C2—H2120.0 (17)H2A—O2—H2C109 (3)
N3—C4—N9126.0 (2)H2B—O2—H2C129 (4)
N3—C4—C5126.7 (2)H3A—O3—H3B107 (3)
C5—C4—N9107.3 (2)O21—N21—O22122.0 (2)
N7—C5—C6132.1 (2)O21—N21—O23120.2 (2)
C4—C5—N7106.9 (2)O22—N21—O23117.8 (2)
N3—C4—C5—N7179.1 (2)C4—N3—C2—N10.6 (3)
N3—C4—C5—C60.7 (4)C4—N9—C8—N70.4 (3)
N7—C5—C6—O61.3 (5)C4—C5—C6—O6178.9 (2)
N7—C5—C6—N1180.0 (2)C4—C5—C6—N10.3 (3)
N9—C4—C5—N70.2 (3)C5—N7—C8—N90.3 (3)
N9—C4—C5—C6180.0 (2)C6—N1—C2—N31.6 (4)
C2—N1—C6—O6179.9 (2)C8—N7—C5—C40.0 (3)
C2—N1—C6—C51.3 (3)C8—N7—C5—C6179.8 (3)
C2—N3—C4—N9179.8 (2)C8—N9—C4—N3179.0 (2)
C2—N3—C4—C50.5 (4)C8—N9—C4—C50.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O12_$5i0.98 (3)2.23 (3)2.924 (3)127 (3)
N1—H1···O11_$5i0.98 (3)2.13 (3)3.099 (3)171 (3)
N7—H7···O13_$1ii0.98 (4)2.45 (4)3.208 (3)133 (3)
N7—H7···O12_$1ii0.98 (4)1.73 (4)2.695 (3)167 (3)
N9—H9···O110.88 (3)2.49 (3)3.121 (3)129 (2)
N9—H9···O130.88 (3)1.85 (3)2.731 (3)173 (3)
C2—H2···O6_$2iii0.95 (3)2.50 (3)3.327 (3)145 (2)
C2—H2···O12_$5i0.95 (3)2.40 (3)3.018 (3)122 (2)
C8—H8···O1_$1ii0.97 (3)2.50 (3)3.449 (3)166 (2)
O1—H1A···N30.87 (5)2.03 (5)2.853 (3)156 (4)
O1—H1B···O6_$2iii0.89 (4)2.00 (4)2.845 (3)158 (3)
O2—H2A···O10.91 (4)1.66 (4)2.558 (3)166 (3)
O2—H2B···O30.80 (4)1.67 (4)2.458 (3)173 (4)
O2—H2C···O23_$3iv0.96 (4)1.74 (4)2.653 (3)157 (3)
O3—H3A···O22_$4v0.75 (3)1.98 (3)2.728 (3)176 (3)
O3—H3A···O21_$4v0.75 (3)2.60 (3)3.055 (3)121 (3)
O3—H3B···O230.91 (5)1.93 (5)2.814 (3)164 (4)
Symmetry codes: (i) x, y1, z; (ii) x1/2, y+3/2, z1/2; (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-1H,7H-purin-9-ium dinitrate dihydrate (hx2_100k) top
Crystal data top
H3O+·C5H5N4O+·2NO3·2H2OF(000) = 656
Mr = 316.21Dx = 1.735 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
a = 10.9025 (4) ÅCell parameters from 4172 reflections
b = 10.1712 (3) Åθ = 5.0–76.4°
c = 11.3174 (4) ŵ = 1.50 mm1
β = 105.264 (4)°T = 100 K
V = 1210.73 (7) Å3Block, clear light colourless
Z = 40.18 × 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-1Rint = 0.040
ω scansθmax = 77.2°, θmin = 5.0°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
h = 1313
Tmin = 0.836, Tmax = 1.000k = 1212
10131 measured reflectionsl = 1314
2551 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041All 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 reflectionsΔρmax = 0.46 e Å3
238 parametersΔρmin = 0.28 e Å3
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
xyzUiso*/Ueq
O60.29752 (12)0.22636 (12)0.13188 (12)0.0202 (3)
N10.46833 (14)0.24435 (15)0.30056 (14)0.0185 (3)
H10.478 (2)0.159 (3)0.308 (2)0.028 (6)*
N30.55947 (14)0.44366 (15)0.39068 (13)0.0187 (3)
N70.30462 (14)0.53273 (15)0.13876 (14)0.0173 (3)
H70.243 (2)0.517 (2)0.076 (2)0.015 (5)*
N90.44728 (14)0.63345 (14)0.28188 (14)0.0185 (3)
H90.492 (2)0.696 (3)0.328 (2)0.021 (6)*
C20.55504 (17)0.31492 (18)0.38501 (16)0.0192 (3)
H20.615 (2)0.267 (2)0.4425 (18)0.009 (5)*
C40.46717 (16)0.50076 (17)0.30101 (16)0.0170 (3)
C50.37700 (16)0.43719 (17)0.21119 (15)0.0165 (3)
C60.37245 (16)0.29647 (17)0.20514 (15)0.0173 (3)
C80.34903 (17)0.64895 (17)0.18356 (16)0.0182 (3)
H80.314 (2)0.726 (3)0.149 (2)0.020 (5)*
N110.55332 (14)0.92716 (15)0.39158 (13)0.0179 (3)
O120.61073 (12)1.02793 (13)0.44347 (12)0.0217 (3)
O110.46243 (13)0.93913 (13)0.29982 (12)0.0240 (3)
O130.58970 (13)0.81555 (13)0.43578 (12)0.0221 (3)
O10.78466 (13)0.54213 (13)0.55666 (12)0.0233 (3)
H1A0.801 (3)0.467 (3)0.594 (3)0.045 (8)*
H1B0.716 (3)0.524 (3)0.494 (3)0.047 (9)*
O20.96449 (13)0.64578 (13)0.48016 (13)0.0225 (3)
H2A0.896 (5)0.601 (5)0.511 (5)0.116 (18)*
H2B0.918 (4)0.723 (5)0.437 (4)0.087 (14)*
H2C1.038 (4)0.659 (4)0.554 (3)0.064 (11)*
O30.86387 (14)0.84073 (13)0.36986 (14)0.0271 (3)
H3A0.877 (3)0.927 (3)0.398 (3)0.046 (8)*
H3B0.802 (3)0.837 (3)0.314 (3)0.036 (7)*
N210.66682 (14)0.66028 (15)0.16339 (14)0.0192 (3)
O210.74039 (14)0.60155 (14)0.24818 (13)0.0268 (3)
O220.59449 (13)0.60015 (13)0.07509 (12)0.0232 (3)
O230.66063 (13)0.78614 (13)0.16482 (12)0.0233 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O60.0197 (6)0.0152 (5)0.0225 (6)0.0020 (4)0.0001 (5)0.0021 (5)
N10.0193 (7)0.0140 (7)0.0197 (7)0.0005 (5)0.0010 (6)0.0016 (5)
N30.0181 (7)0.0176 (7)0.0183 (7)0.0005 (5)0.0012 (5)0.0003 (5)
N70.0162 (7)0.0150 (7)0.0185 (7)0.0012 (5)0.0003 (6)0.0004 (5)
N90.0188 (7)0.0144 (7)0.0208 (7)0.0004 (5)0.0025 (6)0.0017 (5)
C20.0187 (8)0.0181 (8)0.0188 (8)0.0005 (6)0.0015 (6)0.0008 (6)
C40.0174 (8)0.0153 (8)0.0179 (7)0.0000 (6)0.0039 (6)0.0013 (6)
C50.0155 (7)0.0151 (8)0.0178 (7)0.0001 (6)0.0023 (6)0.0001 (6)
C60.0168 (8)0.0170 (8)0.0173 (7)0.0005 (6)0.0030 (6)0.0008 (6)
C80.0177 (8)0.0150 (8)0.0210 (8)0.0025 (6)0.0036 (6)0.0009 (6)
N110.0177 (7)0.0160 (7)0.0183 (7)0.0009 (5)0.0015 (5)0.0003 (5)
O120.0212 (6)0.0146 (6)0.0249 (6)0.0023 (5)0.0016 (5)0.0009 (5)
O110.0225 (6)0.0222 (6)0.0215 (6)0.0020 (5)0.0044 (5)0.0009 (5)
O130.0250 (7)0.0136 (6)0.0241 (6)0.0016 (5)0.0002 (5)0.0010 (5)
O10.0216 (6)0.0194 (6)0.0231 (6)0.0033 (5)0.0042 (5)0.0040 (5)
O20.0209 (6)0.0173 (6)0.0258 (7)0.0004 (5)0.0002 (5)0.0009 (5)
O30.0269 (7)0.0172 (6)0.0283 (7)0.0014 (5)0.0083 (6)0.0008 (5)
N210.0172 (7)0.0171 (7)0.0213 (7)0.0010 (5)0.0017 (6)0.0012 (5)
O210.0269 (7)0.0214 (6)0.0249 (7)0.0009 (5)0.0064 (5)0.0028 (5)
O220.0234 (6)0.0185 (6)0.0226 (6)0.0021 (5)0.0029 (5)0.0027 (5)
O230.0244 (7)0.0145 (6)0.0268 (6)0.0003 (5)0.0005 (5)0.0008 (5)
Geometric parameters (Å, º) top
O6—C61.227 (2)C8—H80.91 (3)
N1—H10.87 (3)N11—O121.262 (2)
N1—C21.359 (2)N11—O111.238 (2)
N1—C61.395 (2)N11—O131.262 (2)
N3—C21.311 (2)O1—H1A0.87 (4)
N3—C41.357 (2)O1—H1B0.90 (3)
N7—H70.85 (3)O2—H2A1.01 (6)
N7—C51.378 (2)O2—H2B0.99 (5)
N7—C81.326 (2)O2—H2C1.00 (4)
N9—H90.88 (3)O3—H2B1.46 (5)
N9—C41.375 (2)O3—H3A0.93 (3)
N9—C81.335 (2)O3—H3B0.79 (3)
C2—H20.93 (2)N21—O211.231 (2)
C4—C51.375 (2)N21—O221.257 (2)
C5—C61.433 (2)N21—O231.282 (2)
C2—N1—H1114.1 (18)O6—C6—N1122.14 (16)
C2—N1—C6125.77 (16)O6—C6—C5128.39 (16)
C6—N1—H1120.1 (18)N1—C6—C5109.46 (15)
C2—N3—C4112.34 (15)N7—C8—N9110.20 (15)
C5—N7—H7124.6 (16)N7—C8—H8122.2 (15)
C8—N7—H7127.5 (16)N9—C8—H8127.6 (16)
C8—N7—C5107.87 (15)O11—N11—O12119.97 (15)
C4—N9—H9125.0 (17)O11—N11—O13121.31 (15)
C8—N9—H9127.2 (17)O13—N11—O12118.72 (14)
C8—N9—C4107.80 (15)H1A—O1—H1B103 (3)
N1—C2—H2116.3 (13)H2A—O2—H2B101 (4)
N3—C2—N1124.87 (16)H2A—O2—H2C106 (4)
N3—C2—H2118.8 (13)H2B—O2—H2C120 (3)
N3—C4—N9126.36 (16)H2B—O3—H3A126 (3)
N3—C4—C5126.61 (16)H2B—O3—H3B121 (3)
N9—C4—C5107.02 (15)H3A—O3—H3B110 (3)
N7—C5—C6131.97 (16)O21—N21—O22121.82 (16)
C4—C5—N7107.10 (15)O21—N21—O23120.01 (15)
C4—C5—C6120.92 (16)O22—N21—O23118.15 (15)
N3—C4—C5—N7178.82 (16)C4—N3—C2—N10.5 (3)
N3—C4—C5—C60.4 (3)C4—N9—C8—N70.2 (2)
N7—C5—C6—O61.8 (3)C4—C5—C6—O6179.17 (17)
N7—C5—C6—N1179.51 (17)C4—C5—C6—N10.5 (2)
N9—C4—C5—N70.39 (19)C5—N7—C8—N90.1 (2)
N9—C4—C5—C6179.63 (15)C6—N1—C2—N31.6 (3)
C2—N1—C6—O6179.79 (16)C8—N7—C5—C40.30 (19)
C2—N1—C6—C51.4 (2)C8—N7—C5—C6179.43 (18)
C2—N3—C4—N9179.51 (17)C8—N9—C4—N3178.87 (16)
C2—N3—C4—C50.4 (3)C8—N9—C4—C50.34 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O12_$5i0.87 (3)2.25 (3)2.924 (2)134 (2)
N1—H1···O11_$5i0.87 (3)2.25 (3)3.105 (2)168 (2)
N7—H7···O13_$1ii0.85 (3)2.61 (2)3.212 (2)129 (2)
N7—H7···O12_$1ii0.85 (3)1.85 (3)2.697 (2)176 (2)
N9—H9···O110.88 (3)2.51 (3)3.117 (2)127 (2)
N9—H9···O130.88 (3)1.85 (3)2.730 (2)175 (2)
C2—H2···O6_$2iii0.93 (2)2.51 (2)3.329 (2)146.6 (18)
C2—H2···O12_$5i0.93 (2)2.43 (2)3.019 (2)121.3 (16)
C8—H8···O1_$1ii0.91 (3)2.57 (3)3.449 (2)163 (2)
O1—H1A···O6_$2iii0.87 (4)2.01 (4)2.8530 (18)161 (3)
O1—H1B···N30.90 (3)1.98 (3)2.852 (2)163 (3)
O2—H2A···O11.01 (6)1.56 (6)2.5687 (19)176 (5)
O2—H2B···O30.99 (5)1.46 (5)2.4439 (19)173 (4)
O2—H2C···O23_$3iv1.00 (4)1.67 (4)2.6584 (19)168 (4)
O3—H3A···O22_$4v0.93 (3)1.80 (3)2.7217 (19)169 (3)
O3—H3A···O21_$4v0.93 (3)2.53 (3)3.052 (2)116 (2)
O3—H3B···O230.79 (3)2.03 (3)2.810 (2)167 (3)
Symmetry codes: (i) x, y1, z; (ii) x1/2, y+3/2, z1/2; (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.
top
D—H···AD—HH···AD···AD—H···AD—HH···AD···AD—H···AD—HH···AD···AD—H···A
20 K105 K285 K
C2—H2···O12i0.952.423.017 (6)120.50.946 (14)2.394 (14)3.0131 (15)122.8 (10)0.97 (2)2.41 (2)3.043 (2)122.6 (17)
C2—H2···O6iii0.952.623.476 (6)150.50.946 (14)2.637 (14)3.4750 (15)147.9 (11)0.97 (2)2.63 (2)3.480 (2)146.5 (17)
C8—H8···O1ii0.98 (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···O11i0.882.143.015 (5)171.90.981 (14)2.050 (15)3.0235 (14)171.3 (12)0.94 (3)2.15 (3)3.083 (2)169 (3)
N1—H1···O12i0.882.312.941 (5)128.90.981 (14)2.237 (14)2.9433 (13)127.9 (11)0.94 (3)2.23 (3)2.942 (2)132 (2)
N7—H7···O12ii0.88 (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···O13ii0.88 (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···O110.85 (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···O130.85 (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···O6iii0.79 (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···N30.95 (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.
top
D—H···AD—HH···AD···AD—H···AD—HH···AD···AD—H···A
20 K100 K
C2—H2···O12i0.95 (3)2.40 (3)3.018 (3)122 (2)0.93 (2)2.43 (2)3.019 (2)121.3 (16)
C2—H2···O6iii0.95 (3)2.50 (3)3.327 (3)145 (2)0.93 (2)2.51 (2)3.329 (2)146.6 (18)
C8—H8···O1ii0.97 (3)2.50 (3)3.449 (3)166 (2)0.91 (3)2.57 (3)3.449 (2)163 (2)
N1—H1···O11i0.98 (3)2.13 (3)3.099 (3)171 (3)0.87 (3)2.25 (3)3.105 (2)168 (2)
N1—H1···O12i0.98 (3)2.23 (3)2.924 (3)127 (3)0.87 (3)2.25 (3)2.924 (2)134 (2)
N7—H7···O12ii0.98 (4)1.73 (4)2.695 (3)167 (3)0.85 (3)1.85 (3)2.697 (2)176 (2)
N7—H7···O13ii0.98 (4)2.45 (4)3.208 (3)133 (3)0.85 (3)2.61 (2)3.212 (2)129 (2)
N9—H9···O110.88 (3)2.49 (3)3.121 (3)129 (2)0.88 (3)2.51 (3)3.117 (2)127 (2)
N9—H9···O130.88 (3)1.85 (3)2.731 (3)173 (3)0.88 (3)1.85 (3)2.730 (2)175 (2)
O1—H1A···O6iii0.89 (4)2.00 (4)2.845 (3)158 (3)0.87 (4)2.01 (4)2.8530 (18)161 (3)
O1—H1B···N30.87 (5)2.03 (5)2.853 (3)156 (4)0.90 (3)1.98 (3)2.852 (2)163 (3)
O2—H2A···O10.91 (4)1.66 (4)2.558 (3)166 (3)1.01 (6)1.56 (6)2.5687 (19)176 (5)
O2—H2B···O30.80 (4)1.67 (4)2.458 (3)173 (4)0.99 (5)1.46 (5)2.4439 (19)173 (4)
O2—H2C···O23iv0.96 (4)1.74 (4)2.653 (3)157 (3)1.00 (4)1.67 (4)2.6584 (19)168 (4)
O3—H3A···O21v0.75 (3)1.98 (3)2.728 (3)176 (3)0.93 (3)2.53 (3)3.052 (2)116 (2)
O3—H3A···O22v0.75 (3)2.60 (3)3.055 (3)121 (3)0.93 (3)1.80 (3)2.7217 (19)169 (3)
O3—H3B···O230.91 (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.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds