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The crystal structures of three similar guaninium salts, guaninium monohydrogenphosphite monohydrate, C5H6N5O+·H2O3P-·H2O, guaninium monohydrogenphosphite dihydrate, C5H6N5O+·H2O3P-·2H2O, and guaninium dihydrogenmonophosphate monohydrate, C5H6N5O+·H2O4P-·H2O, are described and compared. The crystal structures have been determined from accurate single-crystal X-ray data sets collected at 100 (2) K. The two phosphite salts are monoclinic, space group P21/c, with different packing and the monophosphate salt is also monoclinic, space group P21/n. An investigation of the hydrogen-bond network in these guaninium salts reveals the existence of two ketoamine tautomers, the N9H form and an N7H form.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768107005332/lb5008sup1.cif
Contains datablocks GPO3m, GPO3b, GPO4

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107005332/lb5008GPO3msup2.fcf
Contains datablock GPO3m

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107005332/lb5008GPO3bsup3.fcf
Contains datablock GPO3b

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107005332/lb5008GPO4sup4.fcf
Contains datablock GPO4

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768107005332/lb5008sup5.pdf
Variation of imidazolyl and pyrimidine ring geometries

CCDC references: 650649; 650650; 650651

Computing details top

For all compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED (Oxford Diffraction, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
(GPO3m) top
Crystal data top
(C5H6N5O1)+·(H2PO3)·H2OZ = 4
Mr = 251.15F(000) = 520
Monoclinic, P21/cDx = 1.751 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 4.9700 (2) Åθ = 3.2–30.0°
b = 12.7506 (7) ŵ = 0.31 mm1
c = 15.0499 (8) ÅT = 100 K
β = 92.293 (4)°Needle, white
V = 952.96 (8) Å30.40 × 0.15 × 0.10 mm
Data collection top
Xcalibur-Saphire2
diffractometer
2749 independent reflections
Radiation source: fine-focus sealed tube2727 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ϕ scansθmax = 30.0°, θmin = 3.2°
Absorption correction: integration
Absorb, (DeTitta, 1985)
h = 66
Tmin = 0.93, Tmax = 0.98k = 017
13648 measured reflectionsl = 021
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.043 w = 1/[σ2(Fo2) + (0.0523P)2 + 0.7658P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.105(Δ/σ)max = 0.001
S = 1.15Δρmax = 0.62 e Å3
2749 reflectionsΔρmin = 0.28 e Å3
185 parameters
Crystal data top
(C5H6N5O1)+·(H2PO3)·H2OV = 952.96 (8) Å3
Mr = 251.15Z = 4
Monoclinic, P21/cMo Kα radiation
a = 4.9700 (2) ŵ = 0.31 mm1
b = 12.7506 (7) ÅT = 100 K
c = 15.0499 (8) Å0.40 × 0.15 × 0.10 mm
β = 92.293 (4)°
Data collection top
Xcalibur-Saphire2
diffractometer
2749 independent reflections
Absorption correction: integration
Absorb, (DeTitta, 1985)
2727 reflections with I > 2σ(I)
Tmin = 0.93, Tmax = 0.98Rint = 0.041
13648 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.15Δρmax = 0.62 e Å3
2749 reflectionsΔρmin = 0.28 e Å3
185 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
H80.817 (3)0.7970 (14)0.1667 (12)0.020 (4)*
H210.013 (5)0.4854 (18)0.0861 (16)0.025 (6)*
H120.272 (5)0.601 (2)0.2884 (18)0.039 (7)*
H110.080 (6)0.682 (2)0.274 (2)0.046 (8)*
H70.969 (5)0.820 (2)0.0242 (17)0.032 (6)*
H220.096 (5)0.5126 (19)0.1762 (17)0.024 (6)*
H90.423 (5)0.686 (2)0.1652 (18)0.037 (7)*
H10.423 (5)0.6202 (18)0.1928 (16)0.023 (5)*
H50.644 (6)0.459 (2)0.566 (2)0.050 (9)*
H0.142 (4)0.4446 (17)0.6094 (14)0.017 (5)*
P10.28890 (7)0.52526 (3)0.61383 (2)0.0101 (1)
O40.2423 (2)0.58748 (8)0.52824 (7)0.0128 (2)
O50.5858 (2)0.48095 (9)0.61714 (7)0.0151 (2)
O30.2386 (2)0.58280 (9)0.69771 (7)0.0153 (2)
N30.2822 (2)0.59992 (10)0.00498 (8)0.0122 (2)
N70.8254 (2)0.77802 (10)0.03761 (8)0.0123 (2)
N90.5280 (2)0.69991 (10)0.11841 (8)0.0121 (2)
N10.4481 (2)0.63437 (10)0.13880 (8)0.0120 (2)
C60.6555 (3)0.70254 (11)0.11321 (9)0.0120 (2)
O60.8005 (2)0.74284 (9)0.16856 (7)0.0155 (2)
C50.6651 (3)0.71671 (11)0.01918 (9)0.0113 (2)
C40.4780 (3)0.66731 (11)0.03219 (9)0.0114 (2)
C20.2764 (3)0.58490 (11)0.08280 (9)0.0114 (2)
N20.0989 (3)0.51805 (10)0.12047 (9)0.0148 (2)
C80.7379 (3)0.76659 (11)0.11922 (10)0.0128 (3)
O1W0.1947 (2)0.63945 (9)0.24633 (7)0.0157 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0103 (2)0.0119 (2)0.0079 (2)0.0005 (1)0.0000 (1)0.0003 (1)
O40.0135 (5)0.0155 (5)0.0092 (4)0.0030 (4)0.0001 (3)0.0011 (3)
O50.0124 (5)0.0224 (5)0.0107 (5)0.0063 (4)0.0003 (4)0.0012 (4)
O30.0170 (5)0.0197 (5)0.0092 (5)0.0018 (4)0.0012 (4)0.0029 (4)
N30.0132 (5)0.0136 (5)0.0098 (5)0.0004 (4)0.0011 (4)0.0004 (4)
N70.0120 (5)0.0123 (5)0.0127 (5)0.0009 (4)0.0002 (4)0.0010 (4)
N90.0127 (5)0.0129 (5)0.0108 (5)0.0006 (4)0.0009 (4)0.0005 (4)
N10.0137 (5)0.0144 (5)0.0081 (5)0.0013 (4)0.0015 (4)0.0009 (4)
C60.0125 (6)0.0117 (6)0.0118 (6)0.0005 (4)0.0021 (4)0.0008 (4)
O60.0168 (5)0.0174 (5)0.0127 (5)0.0035 (4)0.0057 (4)0.0007 (4)
C50.0116 (6)0.0119 (6)0.0106 (6)0.0009 (4)0.0012 (4)0.0010 (4)
C40.0117 (6)0.0116 (6)0.0110 (6)0.0014 (4)0.0018 (4)0.0005 (4)
C20.0114 (6)0.0110 (6)0.0120 (6)0.0010 (4)0.0010 (4)0.0014 (4)
N20.0158 (6)0.0172 (6)0.0113 (6)0.0039 (4)0.0006 (4)0.0010 (4)
C80.0130 (6)0.0122 (6)0.0131 (6)0.0008 (5)0.0005 (5)0.0004 (5)
O1W0.0163 (5)0.0187 (5)0.0122 (5)0.0039 (4)0.0021 (4)0.0028 (4)
Geometric parameters (Å, º) top
P1—O31.4899 (11)N1—C21.3760 (17)
P1—O41.5226 (10)N1—C61.3912 (18)
P1—O51.5791 (11)N1—H10.84 (2)
P1—H1.26 (2)C6—O61.2348 (17)
O5—H50.87 (3)C6—C51.4256 (19)
N3—C21.3340 (18)C5—C41.3842 (18)
N3—C41.3495 (18)C2—N21.3364 (18)
N7—C81.3271 (18)N2—H210.88 (2)
N7—C51.3865 (17)N2—H220.84 (2)
N7—H70.92 (3)C8—H80.890 (18)
N9—C81.3454 (18)O1W—H120.88 (3)
N9—C41.3757 (18)O1W—H110.90 (3)
N9—H90.91 (3)
O3—P1—O4115.81 (6)O6—C6—C5128.31 (13)
O3—P1—O5109.73 (6)N1—C6—C5110.41 (12)
O4—P1—O5108.87 (6)C4—C5—N7107.13 (12)
O3—P1—H109.2 (10)C4—C5—C6120.03 (12)
O4—P1—H108.2 (10)N7—C5—C6132.75 (13)
O5—P1—H104.4 (10)N3—C4—N9125.42 (12)
P1—O5—H5115 (2)N3—C4—C5127.77 (13)
C2—N3—C4112.25 (12)N9—C4—C5106.81 (12)
C8—N7—C5107.88 (12)N3—C2—N2119.96 (13)
C8—N7—H7123.5 (16)N3—C2—N1123.46 (13)
C5—N7—H7128.6 (16)N2—C2—N1116.58 (13)
C8—N9—C4108.08 (12)C2—N2—H21118.4 (16)
C8—N9—H9125.8 (17)C2—N2—H22117.4 (16)
C4—N9—H9125.6 (17)H21—N2—H22124 (2)
C2—N1—C6126.00 (12)N7—C8—N9110.10 (13)
C2—N1—H1115.0 (16)N7—C8—H8123.0 (11)
C6—N1—H1119.0 (16)N9—C8—H8126.8 (11)
O6—C6—N1121.28 (13)H12—O1W—H11106 (2)
C2—N1—C6—O6179.59 (13)C8—N9—C4—C50.04 (15)
C2—N1—C6—C51.1 (2)N7—C5—C4—N3179.75 (13)
C8—N7—C5—C40.38 (16)C6—C5—C4—N33.2 (2)
C8—N7—C5—C6176.12 (15)N7—C5—C4—N90.25 (15)
O6—C6—C5—C4177.68 (14)C6—C5—C4—N9176.78 (12)
N1—C6—C5—C41.52 (19)C4—N3—C2—N2178.17 (13)
O6—C6—C5—N71.5 (3)C4—N3—C2—N11.14 (19)
N1—C6—C5—N7177.65 (14)C6—N1—C2—N32.7 (2)
C2—N3—C4—N9178.26 (13)C6—N1—C2—N2176.64 (13)
C2—N3—C4—C51.7 (2)C5—N7—C8—N90.36 (16)
C8—N9—C4—N3179.97 (13)C4—N9—C8—N70.20 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(5)···O(4)i0.88 (3)1.66 (3)2.535 (2)177 (3)
N(7)—H(7)···O(4)ii0.92 (2)1.80 (3)2.698 (2)165 (2)
N(9)—H(9)···O(1W)0.91 (3)1.80 (3)2.702 (2)170 (2)
N(1)—H(1)···O(3)iii0.84 (2)1.91 (2)2.714 (2)160 (2)
O(1W)—H(12)···O(5)i0.88 (3)1.88 (3)2.755 (2)176 (2)
O(1W)—H(11)···O(6)iv0.90 (3)1.92 (3)2.816 (2)172 (3)
N(2)—H(22)···O(3)iii0.84 (3)2.24 (3)2.967 (2)145 (2)
N(2)—H(21)···N(3)v0.88 (2)2.14 (2)3.022 (2)178 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+3/2, z1/2; (iii) x, y, z1; (iv) x1, y+3/2, z+1/2; (v) x, y+1, z.
(GPO3b) top
Crystal data top
C5H6N5O+·H2O3P·2(H2O)Z = 4
Mr = 269.17F(000) = 560
Monoclinic, P21/cDx = 1.692 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 4.6812 (4) Åθ = 3.3–30.0°
b = 24.0561 (15) ŵ = 0.29 mm1
c = 9.5186 (7 ÅT = 100 K
β = 99.773 (7)°Needle, white
V = 1056.35 (14) Å30.60 × 0.15 × 0.10 mm
Data collection top
Xcalibur-Saphire2
diffractometer
3086 independent reflections
Radiation source: fine-focus sealed tube2911 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ϕ scansθmax = 30.0°, θmin = 3.3°
Absorption correction: integration
Absorb, (DeTitta, 1985)
h = 56
Tmin = 0.845, Tmax = 0.972k = 3333
31247 measured reflectionsl = 1313
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.0432P)2 + 0.8027P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.098(Δ/σ)max < 0.001
S = 1.17Δρmax = 0.54 e Å3
3086 reflectionsΔρmin = 0.28 e Å3
202 parameters
Crystal data top
C5H6N5O+·H2O3P·2(H2O)V = 1056.35 (14) Å3
Mr = 269.17Z = 4
Monoclinic, P21/cMo Kα radiation
a = 4.6812 (4) ŵ = 0.29 mm1
b = 24.0561 (15) ÅT = 100 K
c = 9.5186 (7 Å0.60 × 0.15 × 0.10 mm
β = 99.773 (7)°
Data collection top
Xcalibur-Saphire2
diffractometer
3086 independent reflections
Absorption correction: integration
Absorb, (DeTitta, 1985)
2911 reflections with I > 2σ(I)
Tmin = 0.845, Tmax = 0.972Rint = 0.040
31247 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.17Δρmax = 0.54 e Å3
3086 reflectionsΔρmin = 0.28 e Å3
202 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1W0.4597 (3)0.11400 (5)0.04084 (13)0.0172 (2)
O2W0.0514 (3)0.15155 (5)0.70458 (15)0.0247 (3)
H80.015 (4)0.1830 (8)0.816 (2)0.009 (4)*
H90.297 (5)0.1430 (10)0.653 (2)0.023 (5)*
H0.092 (4)0.2250 (8)0.478 (2)0.013 (5)*
H210.447 (5)0.0545 (10)0.520 (2)0.022 (5)*
H220.285 (5)0.0988 (10)0.597 (2)0.022 (5)*
H10.007 (5)0.0717 (11)0.742 (3)0.028 (6)*
H70.233 (6)0.1084 (11)0.913 (3)0.034 (6)*
H110.541 (6)0.0885 (12)0.068 (3)0.039 (7)*
H120.494 (6)0.1424 (12)0.080 (3)0.036 (7)*
H230.044 (6)0.1772 (13)0.748 (3)0.044 (8)*
H240.178 (6)0.1638 (11)0.642 (3)0.036 (7)*
H50.446 (7)0.2530 (14)0.689 (3)0.052 (9)*
P10.35874 (8)0.23491 (1)0.47407 (4)0.0101 (1)
O30.5117 (2)0.17989 (4)0.47468 (11)0.0144 (2)
O50.4664 (3)0.26881 (5)0.61424 (12)0.0171 (2)
O40.3767 (3)0.27326 (5)0.34979 (11)0.0160 (2)
N10.0298 (3)0.03777 (5)0.73717 (13)0.0109 (2)
O60.2770 (2)0.01821 (4)0.89542 (11)0.0131 (2)
N30.2906 (3)0.02995 (5)0.62583 (12)0.0104 (2)
C40.1618 (3)0.06640 (6)0.70325 (14)0.0098 (2)
N90.1937 (3)0.12349 (5)0.70317 (13)0.0112 (2)
C50.0268 (3)0.05458 (6)0.79630 (14)0.0101 (2)
C60.1076 (3)0.00147 (6)0.81858 (14)0.0102 (2)
N70.1074 (3)0.10451 (5)0.85059 (13)0.0114 (2)
C20.2201 (3)0.02272 (6)0.64848 (14)0.0103 (2)
C80.0293 (3)0.14476 (6)0.79372 (15)0.0122 (3)
N20.3372 (3)0.06406 (5)0.58277 (14)0.0131 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1W0.0234 (6)0.0104 (5)0.0206 (5)0.0024 (4)0.0118 (4)0.0021 (4)
O2W0.0275 (6)0.0099 (5)0.0311 (7)0.0020 (4)0.0111 (5)0.0000 (5)
P10.0133 (2)0.0085 (2)0.0090 (2)0.0008 (1)0.0031 (1)0.0004 (1)
O30.0204 (5)0.0096 (4)0.0137 (5)0.0042 (4)0.0043 (4)0.0001 (4)
O50.0318 (6)0.0109 (5)0.0094 (5)0.0046 (4)0.0056 (4)0.0017 (4)
O40.0261 (6)0.0122 (5)0.0102 (5)0.0033 (4)0.0047 (4)0.0017 (4)
N10.0126 (5)0.0080 (5)0.0124 (5)0.0015 (4)0.0029 (4)0.0003 (4)
O60.0140 (5)0.0136 (5)0.0123 (4)0.0030 (4)0.0040 (4)0.0010 (4)
N30.0115 (5)0.0089 (5)0.0109 (5)0.0004 (4)0.0026 (4)0.0005 (4)
C40.0099 (5)0.0092 (6)0.0102 (5)0.0005 (4)0.0010 (4)0.0017 (4)
N90.0126 (5)0.0090 (5)0.0125 (5)0.0005 (4)0.0037 (4)0.0014 (4)
C50.0113 (6)0.0089 (6)0.0107 (5)0.0002 (4)0.0031 (5)0.0001 (4)
C60.0105 (6)0.0101 (6)0.0094 (5)0.0005 (4)0.0002 (4)0.0008 (4)
N70.0120 (5)0.0108 (5)0.0119 (5)0.0003 (4)0.0033 (4)0.0006 (4)
C20.0105 (6)0.0099 (6)0.0098 (5)0.0000 (4)0.0003 (4)0.0005 (4)
C80.0129 (6)0.0098 (6)0.0136 (6)0.0000 (5)0.0021 (5)0.0002 (5)
N20.0153 (5)0.0094 (5)0.0154 (5)0.0003 (4)0.0054 (4)0.0003 (4)
Geometric parameters (Å, º) top
O1W—H110.79 (3)N3—C41.3516 (17)
O1W—H120.81 (3)C4—N91.3816 (17)
O2W—H230.83 (3)C4—C51.3820 (18)
O2W—H240.82 (3)N9—C81.3500 (18)
P1—O31.5043 (11)N9—H90.87 (2)
P1—O41.5137 (11)C5—N71.3851 (17)
P1—O51.5719 (11)C5—C61.4259 (18)
P1—H1.28 (2)N7—C81.3259 (18)
O5—H50.82 (3)N7—H70.91 (3)
N1—C21.3756 (18)C2—N21.3407 (18)
N1—C61.3950 (18)C8—H80.95 (2)
N1—H10.84 (3)N2—H210.88 (2)
O6—C61.2338 (17)N2—H220.89 (2)
N3—C21.3360 (17)
H11—O1W—H12111 (3)C4—C5—N7107.75 (12)
H23—O2W—H24111 (3)C4—C5—C6120.30 (12)
O3—P1—O4116.72 (6)N7—C5—C6131.94 (12)
O3—P1—O5111.68 (6)O6—C6—N1121.88 (13)
O4—P1—O5107.14 (6)O6—C6—C5127.62 (13)
O3—P1—H107.6 (9)N1—C6—C5110.49 (12)
O4—P1—H108.7 (9)C8—N7—C5107.45 (12)
O5—P1—H104.2 (9)C8—N7—H7127.0 (17)
P1—O5—H5115 (2)C5—N7—H7125.5 (17)
C2—N1—C6125.72 (12)N3—C2—N2119.74 (13)
C2—N1—H1116.7 (17)N3—C2—N1123.52 (12)
C6—N1—H1117.6 (17)N2—C2—N1116.74 (12)
C2—N3—C4112.44 (12)N7—C8—N9110.55 (12)
N3—C4—N9125.89 (12)N7—C8—H8124.0 (12)
N3—C4—C5127.49 (13)N9—C8—H8125.5 (12)
N9—C4—C5106.62 (12)C2—N2—H21116.9 (15)
C8—N9—C4107.63 (12)C2—N2—H22118.7 (15)
C8—N9—H9125.1 (15)H21—N2—H22124 (2)
C4—N9—H9127.3 (15)
C2—N3—C4—N9179.66 (13)N7—C5—C6—O60.1 (2)
C2—N3—C4—C50.8 (2)C4—C5—C6—N10.50 (18)
N3—C4—N9—C8179.74 (13)N7—C5—C6—N1179.01 (14)
C5—C4—N9—C80.11 (15)C4—C5—N7—C80.61 (15)
N3—C4—C5—N7179.32 (13)C6—C5—N7—C8179.25 (14)
N9—C4—C5—N70.30 (15)C4—N3—C2—N2177.98 (12)
N3—C4—C5—C60.5 (2)C4—N3—C2—N12.05 (19)
N9—C4—C5—C6179.13 (12)C6—N1—C2—N32.2 (2)
C2—N1—C6—O6179.72 (13)C6—N1—C2—N2177.81 (13)
C2—N1—C6—C50.75 (19)C5—N7—C8—N90.69 (16)
C4—C5—C6—O6178.39 (14)C4—N9—C8—N70.51 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(5)···O(4)i0.83 (3)1.74 (3)2.559 (2)173 (4)
N(7)—H(7)···O(1W)ii0.91 (3)1.75 (3)2.658 (2)177 (3)
N(9)—H(9)···O(3)iii0.87 (2)1.85 (2)2.721 (2)172 (2)
O(1W)—H(11)···O(6)iv0.79 (2)1.95 (2)2.730 (2)169 (2)
N(1)—H(1)···O(2W)0.84 (3)1.96 (3)2.773 (2)164 (3)
O(2W)—H(24)···O(3)v0.82 (3)2.00 (3)2.814 (2)170 (3)
O(2W)—H(23)···O(4)i0.83 (3)2.07 (3)2.874 (2)164 (3)
O(1W)—H(12)···O(4)vi0.81 (3)2.18 (3)2.907 (2)151 (3)
N(2)—H(21)···N(3)iii0.88 (2)2.09 (2)2.971 (2)178 (2)
N(2)—H(22)···O(3)0.89 (2)2.59 (2)3.126 (2)120 (2)
N(2)—H(22)···O(2W)0.89 (2)2.38 (2)3.130 (2)142 (2)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y, z+1; (iii) x+1, y, z+1; (iv) x1, y, z+1; (v) x1, y, z; (vi) x, y1/2, z+1/2.
(GPO4) top
Crystal data top
(C5H6N5O1)+·(H2PO4)·H2OZ = 4
Mr = 267.15F(000) = 552
Monoclinic, P21/nDx = 1.715 Mg m3
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 4.5414 (3) Åθ = 3.7–30.0°
b = 12.5774 (6) ŵ = 0.30 mm1
c = 18.1485 (9) ÅT = 100 K
β = 93.689 (5)°Needle, white
V = 1034.48 (10) Å30.42 × 0.10 × 0.07 mm
Data collection top
Xcalibur-Saphire2
diffractometer
3013 independent reflections
Radiation source: fine-focus sealed tube2971 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
ϕ scansθmax = 30.0°, θmin = 3.7°
Absorption correction: integration
Absorb, (DeTitta, 1985)
h = 65
Tmin = 0.87, Tmax = 0.98k = 1717
42941 measured reflectionsl = 2525
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.064P)2 + 0.5194P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.107(Δ/σ)max < 0.001
S = 1.11Δρmax = 0.54 e Å3
3013 reflectionsΔρmin = 0.38 e Å3
194 parameters
Crystal data top
(C5H6N5O1)+·(H2PO4)·H2OV = 1034.48 (10) Å3
Mr = 267.15Z = 4
Monoclinic, P21/nMo Kα radiation
a = 4.5414 (3) ŵ = 0.30 mm1
b = 12.5774 (6) ÅT = 100 K
c = 18.1485 (9) Å0.42 × 0.10 × 0.07 mm
β = 93.689 (5)°
Data collection top
Xcalibur-Saphire2
diffractometer
3013 independent reflections
Absorption correction: integration
Absorb, (DeTitta, 1985)
2971 reflections with I > 2σ(I)
Tmin = 0.87, Tmax = 0.98Rint = 0.063
42941 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.54 e Å3
3013 reflectionsΔρmin = 0.38 e Å3
194 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O60.7880 (2)0.47228 (8)0.26876 (6)0.0163 (2)
N70.5312 (2)0.70398 (9)0.27694 (6)0.0119 (2)
N90.2068 (2)0.73788 (9)0.35871 (6)0.0125 (2)
N20.1965 (3)0.38974 (10)0.45533 (7)0.0163 (2)
C40.2893 (3)0.63332 (10)0.36871 (7)0.0110 (2)
N10.4863 (2)0.43853 (9)0.36100 (6)0.0123 (2)
C80.3576 (3)0.77713 (10)0.30321 (7)0.0132 (2)
N30.1828 (2)0.56524 (9)0.41787 (6)0.0124 (2)
C60.6063 (3)0.50706 (10)0.31146 (7)0.0118 (2)
C20.2857 (3)0.46676 (10)0.41152 (7)0.0118 (2)
C50.4939 (3)0.61158 (10)0.31720 (7)0.0117 (2)
P10.53006 (7)0.13870 (2)0.38133 (2)0.00980 (10)
O30.7942 (2)0.07895 (8)0.42348 (6)0.0145 (2)
O10.3013 (2)0.16979 (8)0.43410 (5)0.01273 (19)
O20.6455 (2)0.23068 (8)0.33815 (5)0.0138 (2)
O40.3817 (2)0.05213 (8)0.32854 (6)0.0146 (2)
O1W0.7969 (2)0.85448 (8)0.41964 (6)0.0154 (2)
H80.341 (5)0.8484 (16)0.2869 (11)0.017 (5)*
H210.091 (5)0.4023 (18)0.4890 (13)0.024 (5)*
H10.539 (5)0.3695 (19)0.3581 (13)0.029 (6)*
H90.068 (5)0.775 (2)0.3853 (14)0.034 (6)*
H220.238 (5)0.3225 (19)0.4475 (12)0.024 (5)*
H70.637 (7)0.719 (2)0.2368 (17)0.054 (8)*
H120.740 (6)0.846 (2)0.4631 (16)0.040 (7)*
H110.820 (6)0.916 (3)0.4158 (16)0.047 (8)*
H40.500 (7)0.034 (2)0.2964 (17)0.051 (8)*
H30.972 (6)0.110 (2)0.4236 (13)0.033 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O60.0209 (5)0.0126 (4)0.0163 (5)0.0034 (3)0.0084 (4)0.0012 (3)
N70.0145 (5)0.0096 (5)0.0118 (5)0.0000 (4)0.0025 (4)0.0005 (4)
N90.0145 (5)0.0095 (5)0.0138 (5)0.0006 (4)0.0038 (4)0.0001 (4)
N20.0223 (6)0.0103 (5)0.0176 (5)0.0020 (4)0.0108 (4)0.0027 (4)
C40.0123 (5)0.0093 (5)0.0116 (5)0.0004 (4)0.0018 (4)0.0015 (4)
N10.0149 (5)0.0094 (5)0.0130 (5)0.0016 (4)0.0051 (4)0.0008 (4)
C80.0152 (5)0.0101 (5)0.0144 (6)0.0008 (4)0.0025 (4)0.0002 (4)
N30.0151 (5)0.0098 (5)0.0125 (5)0.0002 (4)0.0038 (4)0.0000 (4)
C60.0139 (5)0.0107 (5)0.0108 (5)0.0002 (4)0.0020 (4)0.0005 (4)
C20.0135 (5)0.0116 (5)0.0107 (5)0.0004 (4)0.0029 (4)0.0001 (4)
C50.0138 (5)0.0109 (5)0.0106 (5)0.0002 (4)0.0021 (4)0.0008 (4)
P10.0103 (2)0.0083 (2)0.0110 (2)0.0006 (1)0.0026 (1)0.0004 (1)
O30.0110 (4)0.0122 (4)0.0202 (5)0.0003 (3)0.0004 (3)0.0038 (3)
O10.0128 (4)0.0126 (4)0.0133 (4)0.0007 (3)0.0051 (3)0.0008 (3)
O20.0176 (4)0.0103 (4)0.0142 (4)0.0011 (3)0.0065 (3)0.0022 (3)
O40.0156 (4)0.0137 (4)0.0146 (5)0.0012 (3)0.0025 (3)0.0035 (3)
O1W0.0201 (5)0.0114 (4)0.0150 (5)0.0025 (3)0.0044 (4)0.0004 (3)
Geometric parameters (Å, º) top
O6—C61.2470 (16)N1—C21.3798 (16)
N7—C81.3205 (17)N1—C61.3825 (16)
N7—C51.3888 (16)N3—C21.3315 (16)
N9—C81.3475 (17)C6—C51.4165 (18)
N9—C41.3762 (16)P1—O11.5090 (9)
N2—C21.3328 (17)P1—O21.5100 (10)
C4—N31.3486 (16)P1—O31.5717 (10)
C4—C51.3870 (17)P1—O41.5729 (10)
C8—N7—C5107.29 (11)N3—C2—N1123.18 (12)
C8—N9—C4107.55 (11)N2—C2—N1116.65 (12)
N3—C4—N9126.00 (11)C4—C5—N7107.41 (11)
N3—C4—C5127.23 (12)C4—C5—C6119.52 (12)
N9—C4—C5106.74 (11)N7—C5—C6132.94 (12)
C2—N1—C6125.20 (11)O1—P1—O2114.01 (6)
N7—C8—N9111.01 (12)O1—P1—O3110.49 (6)
C2—N3—C4112.99 (11)O2—P1—O3109.84 (6)
O6—C6—N1119.32 (12)O1—P1—O4106.30 (6)
O6—C6—C5128.84 (12)O2—P1—O4111.32 (6)
N1—C6—C5111.83 (11)O3—P1—O4104.42 (6)
N3—C2—N2120.17 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O(3)—H(3)···O(1)i0.90 (3)1.67 (3)2.567 (1)174 (2)
O(4)—H(4)···O(6)ii0.85 (3)1.75 (3)2.592 (1)169 (3)
N(7)—H(7)···O(2)iii0.92 (3)1.74 (3)2.651 (2)173 (3)
N(9)—H(9)···O(1W)iv0.94 (2)1.73 (2)2.665 (2)170 (2)
O(1W)—H(12)···O(1)v0.85 (3)1.90 (3)2.737 (1)168 (3)
N(1)—H(1)···O(2)0.90 (2)1.85 (2)2.751 (2)172 (2)
O(1W)—H(11)···O(3)vi0.78 (4)2.06 (4)2.824 (1)165 (3)
N(2)—H(22)···O(1)0.88 (2)1.96 (2)2.838 (2)175 (2)
N(2)—H(21)···N(3)vii0.82 (2)2.20 (2)3.016 (2)178 (3)
Symmetry codes: (i) x+1, y, z; (ii) x+3/2, y1/2, z+1/2; (iii) x+3/2, y+1/2, z+1/2; (iv) x1, y, z; (v) x+1, y+1, z+1; (vi) x, y+1, z; (vii) x, y+1, z+1.

Experimental details

(GPO3m)(GPO3b)(GPO4)
Crystal data
Chemical formula(C5H6N5O1)+·(H2PO3)·H2OC5H6N5O+·H2O3P·2(H2O)(C5H6N5O1)+·(H2PO4)·H2O
Mr251.15269.17267.15
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/n
Temperature (K)100100100
a, b, c (Å)4.9700 (2), 12.7506 (7), 15.0499 (8)4.6812 (4), 24.0561 (15), 9.5186 (74.5414 (3), 12.5774 (6), 18.1485 (9)
β (°) 92.293 (4) 99.773 (7) 93.689 (5)
V3)952.96 (8)1056.35 (14)1034.48 (10)
Z444
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.310.290.30
Crystal size (mm)0.40 × 0.15 × 0.100.60 × 0.15 × 0.100.42 × 0.10 × 0.07
Data collection
DiffractometerXcalibur-Saphire2
diffractometer
Xcalibur-Saphire2
diffractometer
Xcalibur-Saphire2
diffractometer
Absorption correctionIntegration
Absorb, (DeTitta, 1985)
Integration
Absorb, (DeTitta, 1985)
Integration
Absorb, (DeTitta, 1985)
Tmin, Tmax0.93, 0.980.845, 0.9720.87, 0.98
No. of measured, independent and
observed [I > 2σ(I)] reflections
13648, 2749, 2727 31247, 3086, 2911 42941, 3013, 2971
Rint0.0410.0400.063
(sin θ/λ)max1)0.7020.7030.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.105, 1.15 0.040, 0.098, 1.17 0.042, 0.107, 1.11
No. of reflections274930863013
No. of parameters185202194
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.62, 0.280.54, 0.280.54, 0.38

Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Farrugia, 1997), WinGX publication routines (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) for (GPO3m) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(5)···O(4)i0.88 (3)1.66 (3)2.535 (2)177 (3)
N(7)—H(7)···O(4)ii0.92 (2)1.80 (3)2.698 (2)165 (2)
N(9)—H(9)···O(1W)0.91 (3)1.80 (3)2.702 (2)170 (2)
N(1)—H(1)···O(3)iii0.84 (2)1.91 (2)2.714 (2)160 (2)
O(1W)—H(12)···O(5)i0.88 (3)1.88 (3)2.755 (2)176 (2)
O(1W)—H(11)···O(6)iv0.90 (3)1.92 (3)2.816 (2)172 (3)
N(2)—H(22)···O(3)iii0.84 (3)2.24 (3)2.967 (2)145 (2)
N(2)—H(21)···N(3)v0.88 (2)2.14 (2)3.022 (2)178 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+3/2, z1/2; (iii) x, y, z1; (iv) x1, y+3/2, z+1/2; (v) x, y+1, z.
Hydrogen-bond geometry (Å, º) for (GPO3b) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(5)···O(4)i0.83 (3)1.74 (3)2.559 (2)173 (4)
N(7)—H(7)···O(1W)ii0.91 (3)1.75 (3)2.658 (2)177 (3)
N(9)—H(9)···O(3)iii0.87 (2)1.85 (2)2.721 (2)172 (2)
O(1W)—H(11)···O(6)iv0.79 (2)1.95 (2)2.730 (2)169 (2)
N(1)—H(1)···O(2W)0.84 (3)1.96 (3)2.773 (2)164 (3)
O(2W)—H(24)···O(3)v0.82 (3)2.00 (3)2.814 (2)170 (3)
O(2W)—H(23)···O(4)i0.83 (3)2.07 (3)2.874 (2)164 (3)
O(1W)—H(12)···O(4)vi0.81 (3)2.18 (3)2.907 (2)151 (3)
N(2)—H(21)···N(3)iii0.88 (2)2.09 (2)2.971 (2)178 (2)
N(2)—H(22)···O(3)0.89 (2)2.59 (2)3.126 (2)120 (2)
N(2)—H(22)···O(2W)0.89 (2)2.38 (2)3.130 (2)142 (2)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y, z+1; (iii) x+1, y, z+1; (iv) x1, y, z+1; (v) x1, y, z; (vi) x, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (GPO4) top
D—H···AD—HH···AD···AD—H···A
O(3)—H(3)···O(1)i0.90 (3)1.67 (3)2.567 (1)174 (2)
O(4)—H(4)···O(6)ii0.85 (3)1.75 (3)2.592 (1)169 (3)
N(7)—H(7)···O(2)iii0.92 (3)1.74 (3)2.651 (2)173 (3)
N(9)—H(9)···O(1W)iv0.94 (2)1.73 (2)2.665 (2)170 (2)
O(1W)—H(12)···O(1)v0.85 (3)1.90 (3)2.737 (1)168 (3)
N(1)—H(1)···O(2)0.90 (2)1.85 (2)2.751 (2)172 (2)
O(1W)—H(11)···O(3)vi0.78 (4)2.06 (4)2.824 (1)165 (3)
N(2)—H(22)···O(1)0.88 (2)1.96 (2)2.838 (2)175 (2)
N(2)—H(21)···N(3)vii0.82 (2)2.20 (2)3.016 (2)178 (3)
Symmetry codes: (i) x+1, y, z; (ii) x+3/2, y1/2, z+1/2; (iii) x+3/2, y+1/2, z+1/2; (iv) x1, y, z; (v) x+1, y+1, z+1; (vi) x, y+1, z; (vii) x, y+1, z+1.
 

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