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
CCDC references: 650649; 650650; 650651
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).
Crystal data top
(C5H6N5O1)+·(H2PO3)−·H2O | Z = 4 |
Mr = 251.15 | F(000) = 520 |
Monoclinic, P21/c | Dx = 1.751 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 4.9700 (2) Å | θ = 3.2–30.0° |
b = 12.7506 (7) Å | µ = 0.31 mm−1 |
c = 15.0499 (8) Å | T = 100 K |
β = 92.293 (4)° | Needle, white |
V = 952.96 (8) Å3 | 0.40 × 0.15 × 0.10 mm |
Data collection top
Xcalibur-Saphire2 diffractometer | 2749 independent reflections |
Radiation source: fine-focus sealed tube | 2727 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
ϕ scans | θmax = 30.0°, θmin = 3.2° |
Absorption correction: integration Absorb, (DeTitta, 1985) | h = −6→6 |
Tmin = 0.93, Tmax = 0.98 | k = 0→17 |
13648 measured reflections | l = 0→21 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 1.15 | Δρmax = 0.62 e Å−3 |
2749 reflections | Δρmin = −0.28 e Å−3 |
185 parameters | |
Crystal data top
(C5H6N5O1)+·(H2PO3)−·H2O | V = 952.96 (8) Å3 |
Mr = 251.15 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 4.9700 (2) Å | µ = 0.31 mm−1 |
b = 12.7506 (7) Å | T = 100 K |
c = 15.0499 (8) Å | 0.40 × 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 = 0.98 | Rint = 0.041 |
13648 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.15 | Δρmax = 0.62 e Å−3 |
2749 reflections | Δρmin = −0.28 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
H8 | 0.817 (3) | 0.7970 (14) | 0.1667 (12) | 0.020 (4)* | |
H21 | −0.013 (5) | 0.4854 (18) | −0.0861 (16) | 0.025 (6)* | |
H12 | 0.272 (5) | 0.601 (2) | 0.2884 (18) | 0.039 (7)* | |
H11 | 0.080 (6) | 0.682 (2) | 0.274 (2) | 0.046 (8)* | |
H7 | 0.969 (5) | 0.820 (2) | 0.0242 (17) | 0.032 (6)* | |
H22 | 0.096 (5) | 0.5126 (19) | −0.1762 (17) | 0.024 (6)* | |
H9 | 0.423 (5) | 0.686 (2) | 0.1652 (18) | 0.037 (7)* | |
H1 | 0.423 (5) | 0.6202 (18) | −0.1928 (16) | 0.023 (5)* | |
H5 | 0.644 (6) | 0.459 (2) | 0.566 (2) | 0.050 (9)* | |
H | 0.142 (4) | 0.4446 (17) | 0.6094 (14) | 0.017 (5)* | |
P1 | 0.28890 (7) | 0.52526 (3) | 0.61383 (2) | 0.0101 (1) | |
O4 | 0.2423 (2) | 0.58748 (8) | 0.52824 (7) | 0.0128 (2) | |
O5 | 0.5858 (2) | 0.48095 (9) | 0.61714 (7) | 0.0151 (2) | |
O3 | 0.2386 (2) | 0.58280 (9) | 0.69771 (7) | 0.0153 (2) | |
N3 | 0.2822 (2) | 0.59992 (10) | 0.00498 (8) | 0.0122 (2) | |
N7 | 0.8254 (2) | 0.77802 (10) | 0.03761 (8) | 0.0123 (2) | |
N9 | 0.5280 (2) | 0.69991 (10) | 0.11841 (8) | 0.0121 (2) | |
N1 | 0.4481 (2) | 0.63437 (10) | −0.13880 (8) | 0.0120 (2) | |
C6 | 0.6555 (3) | 0.70254 (11) | −0.11321 (9) | 0.0120 (2) | |
O6 | 0.8005 (2) | 0.74284 (9) | −0.16856 (7) | 0.0155 (2) | |
C5 | 0.6651 (3) | 0.71671 (11) | −0.01918 (9) | 0.0113 (2) | |
C4 | 0.4780 (3) | 0.66731 (11) | 0.03219 (9) | 0.0114 (2) | |
C2 | 0.2764 (3) | 0.58490 (11) | −0.08280 (9) | 0.0114 (2) | |
N2 | 0.0989 (3) | 0.51805 (10) | −0.12047 (9) | 0.0148 (2) | |
C8 | 0.7379 (3) | 0.76659 (11) | 0.11922 (10) | 0.0128 (3) | |
O1W | 0.1947 (2) | 0.63945 (9) | 0.24633 (7) | 0.0157 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0103 (2) | 0.0119 (2) | 0.0079 (2) | 0.0005 (1) | −0.0000 (1) | −0.0003 (1) |
O4 | 0.0135 (5) | 0.0155 (5) | 0.0092 (4) | 0.0030 (4) | 0.0001 (3) | 0.0011 (3) |
O5 | 0.0124 (5) | 0.0224 (5) | 0.0107 (5) | 0.0063 (4) | 0.0003 (4) | 0.0012 (4) |
O3 | 0.0170 (5) | 0.0197 (5) | 0.0092 (5) | 0.0018 (4) | 0.0012 (4) | −0.0029 (4) |
N3 | 0.0132 (5) | 0.0136 (5) | 0.0098 (5) | −0.0004 (4) | 0.0011 (4) | −0.0004 (4) |
N7 | 0.0120 (5) | 0.0123 (5) | 0.0127 (5) | −0.0009 (4) | 0.0002 (4) | −0.0010 (4) |
N9 | 0.0127 (5) | 0.0129 (5) | 0.0108 (5) | −0.0006 (4) | 0.0009 (4) | 0.0005 (4) |
N1 | 0.0137 (5) | 0.0144 (5) | 0.0081 (5) | −0.0013 (4) | 0.0015 (4) | −0.0009 (4) |
C6 | 0.0125 (6) | 0.0117 (6) | 0.0118 (6) | 0.0005 (4) | 0.0021 (4) | 0.0008 (4) |
O6 | 0.0168 (5) | 0.0174 (5) | 0.0127 (5) | −0.0035 (4) | 0.0057 (4) | 0.0007 (4) |
C5 | 0.0116 (6) | 0.0119 (6) | 0.0106 (6) | −0.0009 (4) | 0.0012 (4) | −0.0010 (4) |
C4 | 0.0117 (6) | 0.0116 (6) | 0.0110 (6) | 0.0014 (4) | 0.0018 (4) | 0.0005 (4) |
C2 | 0.0114 (6) | 0.0110 (6) | 0.0120 (6) | 0.0010 (4) | 0.0010 (4) | 0.0014 (4) |
N2 | 0.0158 (6) | 0.0172 (6) | 0.0113 (6) | −0.0039 (4) | 0.0006 (4) | −0.0010 (4) |
C8 | 0.0130 (6) | 0.0122 (6) | 0.0131 (6) | 0.0008 (5) | 0.0005 (5) | −0.0004 (5) |
O1W | 0.0163 (5) | 0.0187 (5) | 0.0122 (5) | 0.0039 (4) | 0.0021 (4) | 0.0028 (4) |
Geometric parameters (Å, º) top
P1—O3 | 1.4899 (11) | N1—C2 | 1.3760 (17) |
P1—O4 | 1.5226 (10) | N1—C6 | 1.3912 (18) |
P1—O5 | 1.5791 (11) | N1—H1 | 0.84 (2) |
P1—H | 1.26 (2) | C6—O6 | 1.2348 (17) |
O5—H5 | 0.87 (3) | C6—C5 | 1.4256 (19) |
N3—C2 | 1.3340 (18) | C5—C4 | 1.3842 (18) |
N3—C4 | 1.3495 (18) | C2—N2 | 1.3364 (18) |
N7—C8 | 1.3271 (18) | N2—H21 | 0.88 (2) |
N7—C5 | 1.3865 (17) | N2—H22 | 0.84 (2) |
N7—H7 | 0.92 (3) | C8—H8 | 0.890 (18) |
N9—C8 | 1.3454 (18) | O1W—H12 | 0.88 (3) |
N9—C4 | 1.3757 (18) | O1W—H11 | 0.90 (3) |
N9—H9 | 0.91 (3) | | |
| | | |
O3—P1—O4 | 115.81 (6) | O6—C6—C5 | 128.31 (13) |
O3—P1—O5 | 109.73 (6) | N1—C6—C5 | 110.41 (12) |
O4—P1—O5 | 108.87 (6) | C4—C5—N7 | 107.13 (12) |
O3—P1—H | 109.2 (10) | C4—C5—C6 | 120.03 (12) |
O4—P1—H | 108.2 (10) | N7—C5—C6 | 132.75 (13) |
O5—P1—H | 104.4 (10) | N3—C4—N9 | 125.42 (12) |
P1—O5—H5 | 115 (2) | N3—C4—C5 | 127.77 (13) |
C2—N3—C4 | 112.25 (12) | N9—C4—C5 | 106.81 (12) |
C8—N7—C5 | 107.88 (12) | N3—C2—N2 | 119.96 (13) |
C8—N7—H7 | 123.5 (16) | N3—C2—N1 | 123.46 (13) |
C5—N7—H7 | 128.6 (16) | N2—C2—N1 | 116.58 (13) |
C8—N9—C4 | 108.08 (12) | C2—N2—H21 | 118.4 (16) |
C8—N9—H9 | 125.8 (17) | C2—N2—H22 | 117.4 (16) |
C4—N9—H9 | 125.6 (17) | H21—N2—H22 | 124 (2) |
C2—N1—C6 | 126.00 (12) | N7—C8—N9 | 110.10 (13) |
C2—N1—H1 | 115.0 (16) | N7—C8—H8 | 123.0 (11) |
C6—N1—H1 | 119.0 (16) | N9—C8—H8 | 126.8 (11) |
O6—C6—N1 | 121.28 (13) | H12—O1W—H11 | 106 (2) |
| | | |
C2—N1—C6—O6 | 179.59 (13) | C8—N9—C4—C5 | −0.04 (15) |
C2—N1—C6—C5 | −1.1 (2) | N7—C5—C4—N3 | −179.75 (13) |
C8—N7—C5—C4 | −0.38 (16) | C6—C5—C4—N3 | 3.2 (2) |
C8—N7—C5—C6 | 176.12 (15) | N7—C5—C4—N9 | 0.25 (15) |
O6—C6—C5—C4 | 177.68 (14) | C6—C5—C4—N9 | −176.78 (12) |
N1—C6—C5—C4 | −1.52 (19) | C4—N3—C2—N2 | 178.17 (13) |
O6—C6—C5—N7 | 1.5 (3) | C4—N3—C2—N1 | −1.14 (19) |
N1—C6—C5—N7 | −177.65 (14) | C6—N1—C2—N3 | 2.7 (2) |
C2—N3—C4—N9 | 178.26 (13) | C6—N1—C2—N2 | −176.64 (13) |
C2—N3—C4—C5 | −1.7 (2) | C5—N7—C8—N9 | 0.36 (16) |
C8—N9—C4—N3 | 179.97 (13) | C4—N9—C8—N7 | −0.20 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(5)···O(4)i | 0.88 (3) | 1.66 (3) | 2.535 (2) | 177 (3) |
N(7)—H(7)···O(4)ii | 0.92 (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)iii | 0.84 (2) | 1.91 (2) | 2.714 (2) | 160 (2) |
O(1W)—H(12)···O(5)i | 0.88 (3) | 1.88 (3) | 2.755 (2) | 176 (2) |
O(1W)—H(11)···O(6)iv | 0.90 (3) | 1.92 (3) | 2.816 (2) | 172 (3) |
N(2)—H(22)···O(3)iii | 0.84 (3) | 2.24 (3) | 2.967 (2) | 145 (2) |
N(2)—H(21)···N(3)v | 0.88 (2) | 2.14 (2) | 3.022 (2) | 178 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, −y+3/2, z−1/2; (iii) x, y, z−1; (iv) x−1, −y+3/2, z+1/2; (v) −x, −y+1, −z. |
Crystal data top
C5H6N5O+·H2O3P−·2(H2O) | Z = 4 |
Mr = 269.17 | F(000) = 560 |
Monoclinic, P21/c | Dx = 1.692 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 4.6812 (4) Å | θ = 3.3–30.0° |
b = 24.0561 (15) Å | µ = 0.29 mm−1 |
c = 9.5186 (7 Å | T = 100 K |
β = 99.773 (7)° | Needle, white |
V = 1056.35 (14) Å3 | 0.60 × 0.15 × 0.10 mm |
Data collection top
Xcalibur-Saphire2 diffractometer | 3086 independent reflections |
Radiation source: fine-focus sealed tube | 2911 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
ϕ scans | θmax = 30.0°, θmin = 3.3° |
Absorption correction: integration Absorb, (DeTitta, 1985) | h = −5→6 |
Tmin = 0.845, Tmax = 0.972 | k = −33→33 |
31247 measured reflections | l = −13→13 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 1.17 | Δρmax = 0.54 e Å−3 |
3086 reflections | Δρmin = −0.28 e Å−3 |
202 parameters | |
Crystal data top
C5H6N5O+·H2O3P−·2(H2O) | V = 1056.35 (14) Å3 |
Mr = 269.17 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 4.6812 (4) Å | µ = 0.29 mm−1 |
b = 24.0561 (15) Å | T = 100 K |
c = 9.5186 (7 Å | 0.60 × 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 = 0.972 | Rint = 0.040 |
31247 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | Δρmax = 0.54 e Å−3 |
3086 reflections | Δρmin = −0.28 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1W | −0.4597 (3) | −0.11400 (5) | 0.04084 (13) | 0.0172 (2) | |
O2W | −0.0514 (3) | 0.15155 (5) | 0.70458 (15) | 0.0247 (3) | |
H8 | 0.015 (4) | −0.1830 (8) | 0.816 (2) | 0.009 (4)* | |
H9 | 0.297 (5) | −0.1430 (10) | 0.653 (2) | 0.023 (5)* | |
H | 0.092 (4) | 0.2250 (8) | 0.478 (2) | 0.013 (5)* | |
H21 | 0.447 (5) | 0.0545 (10) | 0.520 (2) | 0.022 (5)* | |
H22 | 0.285 (5) | 0.0988 (10) | 0.597 (2) | 0.022 (5)* | |
H1 | −0.007 (5) | 0.0717 (11) | 0.742 (3) | 0.028 (6)* | |
H7 | −0.233 (6) | −0.1084 (11) | 0.913 (3) | 0.034 (6)* | |
H11 | −0.541 (6) | −0.0885 (12) | 0.068 (3) | 0.039 (7)* | |
H12 | −0.494 (6) | −0.1424 (12) | 0.080 (3) | 0.036 (7)* | |
H23 | 0.044 (6) | 0.1772 (13) | 0.748 (3) | 0.044 (8)* | |
H24 | −0.178 (6) | 0.1638 (11) | 0.642 (3) | 0.036 (7)* | |
H5 | 0.446 (7) | 0.2530 (14) | 0.689 (3) | 0.052 (9)* | |
P1 | 0.35874 (8) | 0.23491 (1) | 0.47407 (4) | 0.0101 (1) | |
O3 | 0.5117 (2) | 0.17989 (4) | 0.47468 (11) | 0.0144 (2) | |
O5 | 0.4664 (3) | 0.26881 (5) | 0.61424 (12) | 0.0171 (2) | |
O4 | 0.3767 (3) | 0.27326 (5) | 0.34979 (11) | 0.0160 (2) | |
N1 | 0.0298 (3) | 0.03777 (5) | 0.73717 (13) | 0.0109 (2) | |
O6 | −0.2770 (2) | 0.01821 (4) | 0.89542 (11) | 0.0131 (2) | |
N3 | 0.2906 (3) | −0.02995 (5) | 0.62583 (12) | 0.0104 (2) | |
C4 | 0.1618 (3) | −0.06640 (6) | 0.70325 (14) | 0.0098 (2) | |
N9 | 0.1937 (3) | −0.12349 (5) | 0.70317 (13) | 0.0112 (2) | |
C5 | −0.0268 (3) | −0.05458 (6) | 0.79630 (14) | 0.0101 (2) | |
C6 | −0.1076 (3) | 0.00147 (6) | 0.81858 (14) | 0.0102 (2) | |
N7 | −0.1074 (3) | −0.10451 (5) | 0.85059 (13) | 0.0114 (2) | |
C2 | 0.2201 (3) | 0.02272 (6) | 0.64848 (14) | 0.0103 (2) | |
C8 | 0.0293 (3) | −0.14476 (6) | 0.79372 (15) | 0.0122 (3) | |
N2 | 0.3372 (3) | 0.06406 (5) | 0.58277 (14) | 0.0131 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1W | 0.0234 (6) | 0.0104 (5) | 0.0206 (5) | 0.0024 (4) | 0.0118 (4) | 0.0021 (4) |
O2W | 0.0275 (6) | 0.0099 (5) | 0.0311 (7) | 0.0020 (4) | −0.0111 (5) | 0.0000 (5) |
P1 | 0.0133 (2) | 0.0085 (2) | 0.0090 (2) | 0.0008 (1) | 0.0031 (1) | −0.0004 (1) |
O3 | 0.0204 (5) | 0.0096 (4) | 0.0137 (5) | 0.0042 (4) | 0.0043 (4) | −0.0001 (4) |
O5 | 0.0318 (6) | 0.0109 (5) | 0.0094 (5) | −0.0046 (4) | 0.0056 (4) | −0.0017 (4) |
O4 | 0.0261 (6) | 0.0122 (5) | 0.0102 (5) | 0.0033 (4) | 0.0047 (4) | 0.0017 (4) |
N1 | 0.0126 (5) | 0.0080 (5) | 0.0124 (5) | 0.0015 (4) | 0.0029 (4) | −0.0003 (4) |
O6 | 0.0140 (5) | 0.0136 (5) | 0.0123 (4) | 0.0030 (4) | 0.0040 (4) | −0.0010 (4) |
N3 | 0.0115 (5) | 0.0089 (5) | 0.0109 (5) | 0.0004 (4) | 0.0026 (4) | −0.0005 (4) |
C4 | 0.0099 (5) | 0.0092 (6) | 0.0102 (5) | 0.0005 (4) | 0.0010 (4) | −0.0017 (4) |
N9 | 0.0126 (5) | 0.0090 (5) | 0.0125 (5) | 0.0005 (4) | 0.0037 (4) | −0.0014 (4) |
C5 | 0.0113 (6) | 0.0089 (6) | 0.0107 (5) | 0.0002 (4) | 0.0031 (5) | −0.0001 (4) |
C6 | 0.0105 (6) | 0.0101 (6) | 0.0094 (5) | 0.0005 (4) | −0.0002 (4) | −0.0008 (4) |
N7 | 0.0120 (5) | 0.0108 (5) | 0.0119 (5) | −0.0003 (4) | 0.0033 (4) | 0.0006 (4) |
C2 | 0.0105 (6) | 0.0099 (6) | 0.0098 (5) | 0.0000 (4) | −0.0003 (4) | −0.0005 (4) |
C8 | 0.0129 (6) | 0.0098 (6) | 0.0136 (6) | 0.0000 (5) | 0.0021 (5) | 0.0002 (5) |
N2 | 0.0153 (5) | 0.0094 (5) | 0.0154 (5) | 0.0003 (4) | 0.0054 (4) | 0.0003 (4) |
Geometric parameters (Å, º) top
O1W—H11 | 0.79 (3) | N3—C4 | 1.3516 (17) |
O1W—H12 | 0.81 (3) | C4—N9 | 1.3816 (17) |
O2W—H23 | 0.83 (3) | C4—C5 | 1.3820 (18) |
O2W—H24 | 0.82 (3) | N9—C8 | 1.3500 (18) |
P1—O3 | 1.5043 (11) | N9—H9 | 0.87 (2) |
P1—O4 | 1.5137 (11) | C5—N7 | 1.3851 (17) |
P1—O5 | 1.5719 (11) | C5—C6 | 1.4259 (18) |
P1—H | 1.28 (2) | N7—C8 | 1.3259 (18) |
O5—H5 | 0.82 (3) | N7—H7 | 0.91 (3) |
N1—C2 | 1.3756 (18) | C2—N2 | 1.3407 (18) |
N1—C6 | 1.3950 (18) | C8—H8 | 0.95 (2) |
N1—H1 | 0.84 (3) | N2—H21 | 0.88 (2) |
O6—C6 | 1.2338 (17) | N2—H22 | 0.89 (2) |
N3—C2 | 1.3360 (17) | | |
| | | |
H11—O1W—H12 | 111 (3) | C4—C5—N7 | 107.75 (12) |
H23—O2W—H24 | 111 (3) | C4—C5—C6 | 120.30 (12) |
O3—P1—O4 | 116.72 (6) | N7—C5—C6 | 131.94 (12) |
O3—P1—O5 | 111.68 (6) | O6—C6—N1 | 121.88 (13) |
O4—P1—O5 | 107.14 (6) | O6—C6—C5 | 127.62 (13) |
O3—P1—H | 107.6 (9) | N1—C6—C5 | 110.49 (12) |
O4—P1—H | 108.7 (9) | C8—N7—C5 | 107.45 (12) |
O5—P1—H | 104.2 (9) | C8—N7—H7 | 127.0 (17) |
P1—O5—H5 | 115 (2) | C5—N7—H7 | 125.5 (17) |
C2—N1—C6 | 125.72 (12) | N3—C2—N2 | 119.74 (13) |
C2—N1—H1 | 116.7 (17) | N3—C2—N1 | 123.52 (12) |
C6—N1—H1 | 117.6 (17) | N2—C2—N1 | 116.74 (12) |
C2—N3—C4 | 112.44 (12) | N7—C8—N9 | 110.55 (12) |
N3—C4—N9 | 125.89 (12) | N7—C8—H8 | 124.0 (12) |
N3—C4—C5 | 127.49 (13) | N9—C8—H8 | 125.5 (12) |
N9—C4—C5 | 106.62 (12) | C2—N2—H21 | 116.9 (15) |
C8—N9—C4 | 107.63 (12) | C2—N2—H22 | 118.7 (15) |
C8—N9—H9 | 125.1 (15) | H21—N2—H22 | 124 (2) |
C4—N9—H9 | 127.3 (15) | | |
| | | |
C2—N3—C4—N9 | −179.66 (13) | N7—C5—C6—O6 | −0.1 (2) |
C2—N3—C4—C5 | 0.8 (2) | C4—C5—C6—N1 | −0.50 (18) |
N3—C4—N9—C8 | −179.74 (13) | N7—C5—C6—N1 | −179.01 (14) |
C5—C4—N9—C8 | −0.11 (15) | C4—C5—N7—C8 | 0.61 (15) |
N3—C4—C5—N7 | 179.32 (13) | C6—C5—N7—C8 | 179.25 (14) |
N9—C4—C5—N7 | −0.30 (15) | C4—N3—C2—N2 | 177.98 (12) |
N3—C4—C5—C6 | 0.5 (2) | C4—N3—C2—N1 | −2.05 (19) |
N9—C4—C5—C6 | −179.13 (12) | C6—N1—C2—N3 | 2.2 (2) |
C2—N1—C6—O6 | −179.72 (13) | C6—N1—C2—N2 | −177.81 (13) |
C2—N1—C6—C5 | −0.75 (19) | C5—N7—C8—N9 | −0.69 (16) |
C4—C5—C6—O6 | 178.39 (14) | C4—N9—C8—N7 | 0.51 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(5)···O(4)i | 0.83 (3) | 1.74 (3) | 2.559 (2) | 173 (4) |
N(7)—H(7)···O(1W)ii | 0.91 (3) | 1.75 (3) | 2.658 (2) | 177 (3) |
N(9)—H(9)···O(3)iii | 0.87 (2) | 1.85 (2) | 2.721 (2) | 172 (2) |
O(1W)—H(11)···O(6)iv | 0.79 (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)v | 0.82 (3) | 2.00 (3) | 2.814 (2) | 170 (3) |
O(2W)—H(23)···O(4)i | 0.83 (3) | 2.07 (3) | 2.874 (2) | 164 (3) |
O(1W)—H(12)···O(4)vi | 0.81 (3) | 2.18 (3) | 2.907 (2) | 151 (3) |
N(2)—H(21)···N(3)iii | 0.88 (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) −x−1, −y, −z+1; (v) x−1, y, z; (vi) −x, y−1/2, −z+1/2. |
Crystal data top
(C5H6N5O1)+·(H2PO4)−·H2O | Z = 4 |
Mr = 267.15 | F(000) = 552 |
Monoclinic, P21/n | Dx = 1.715 Mg m−3 |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 4.5414 (3) Å | θ = 3.7–30.0° |
b = 12.5774 (6) Å | µ = 0.30 mm−1 |
c = 18.1485 (9) Å | T = 100 K |
β = 93.689 (5)° | Needle, white |
V = 1034.48 (10) Å3 | 0.42 × 0.10 × 0.07 mm |
Data collection top
Xcalibur-Saphire2 diffractometer | 3013 independent reflections |
Radiation source: fine-focus sealed tube | 2971 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
ϕ scans | θmax = 30.0°, θmin = 3.7° |
Absorption correction: integration Absorb, (DeTitta, 1985) | h = −6→5 |
Tmin = 0.87, Tmax = 0.98 | k = −17→17 |
42941 measured reflections | l = −25→25 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 1.11 | Δρmax = 0.54 e Å−3 |
3013 reflections | Δρmin = −0.38 e Å−3 |
194 parameters | |
Crystal data top
(C5H6N5O1)+·(H2PO4)−·H2O | V = 1034.48 (10) Å3 |
Mr = 267.15 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 4.5414 (3) Å | µ = 0.30 mm−1 |
b = 12.5774 (6) Å | T = 100 K |
c = 18.1485 (9) Å | 0.42 × 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 = 0.98 | Rint = 0.063 |
42941 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.54 e Å−3 |
3013 reflections | Δρmin = −0.38 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O6 | 0.7880 (2) | 0.47228 (8) | 0.26876 (6) | 0.0163 (2) | |
N7 | 0.5312 (2) | 0.70398 (9) | 0.27694 (6) | 0.0119 (2) | |
N9 | 0.2068 (2) | 0.73788 (9) | 0.35871 (6) | 0.0125 (2) | |
N2 | 0.1965 (3) | 0.38974 (10) | 0.45533 (7) | 0.0163 (2) | |
C4 | 0.2893 (3) | 0.63332 (10) | 0.36871 (7) | 0.0110 (2) | |
N1 | 0.4863 (2) | 0.43853 (9) | 0.36100 (6) | 0.0123 (2) | |
C8 | 0.3576 (3) | 0.77713 (10) | 0.30321 (7) | 0.0132 (2) | |
N3 | 0.1828 (2) | 0.56524 (9) | 0.41787 (6) | 0.0124 (2) | |
C6 | 0.6063 (3) | 0.50706 (10) | 0.31146 (7) | 0.0118 (2) | |
C2 | 0.2857 (3) | 0.46676 (10) | 0.41152 (7) | 0.0118 (2) | |
C5 | 0.4939 (3) | 0.61158 (10) | 0.31720 (7) | 0.0117 (2) | |
P1 | 0.53006 (7) | 0.13870 (2) | 0.38133 (2) | 0.00980 (10) | |
O3 | 0.7942 (2) | 0.07895 (8) | 0.42348 (6) | 0.0145 (2) | |
O1 | 0.3013 (2) | 0.16979 (8) | 0.43410 (5) | 0.01273 (19) | |
O2 | 0.6455 (2) | 0.23068 (8) | 0.33815 (5) | 0.0138 (2) | |
O4 | 0.3817 (2) | 0.05213 (8) | 0.32854 (6) | 0.0146 (2) | |
O1W | 0.7969 (2) | 0.85448 (8) | 0.41964 (6) | 0.0154 (2) | |
H8 | 0.341 (5) | 0.8484 (16) | 0.2869 (11) | 0.017 (5)* | |
H21 | 0.091 (5) | 0.4023 (18) | 0.4890 (13) | 0.024 (5)* | |
H1 | 0.539 (5) | 0.3695 (19) | 0.3581 (13) | 0.029 (6)* | |
H9 | 0.068 (5) | 0.775 (2) | 0.3853 (14) | 0.034 (6)* | |
H22 | 0.238 (5) | 0.3225 (19) | 0.4475 (12) | 0.024 (5)* | |
H7 | 0.637 (7) | 0.719 (2) | 0.2368 (17) | 0.054 (8)* | |
H12 | 0.740 (6) | 0.846 (2) | 0.4631 (16) | 0.040 (7)* | |
H11 | 0.820 (6) | 0.916 (3) | 0.4158 (16) | 0.047 (8)* | |
H4 | 0.500 (7) | 0.034 (2) | 0.2964 (17) | 0.051 (8)* | |
H3 | 0.972 (6) | 0.110 (2) | 0.4236 (13) | 0.033 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O6 | 0.0209 (5) | 0.0126 (4) | 0.0163 (5) | 0.0034 (3) | 0.0084 (4) | 0.0012 (3) |
N7 | 0.0145 (5) | 0.0096 (5) | 0.0118 (5) | 0.0000 (4) | 0.0025 (4) | 0.0005 (4) |
N9 | 0.0145 (5) | 0.0095 (5) | 0.0138 (5) | 0.0006 (4) | 0.0038 (4) | 0.0001 (4) |
N2 | 0.0223 (6) | 0.0103 (5) | 0.0176 (5) | 0.0020 (4) | 0.0108 (4) | 0.0027 (4) |
C4 | 0.0123 (5) | 0.0093 (5) | 0.0116 (5) | 0.0004 (4) | 0.0018 (4) | −0.0015 (4) |
N1 | 0.0149 (5) | 0.0094 (5) | 0.0130 (5) | 0.0016 (4) | 0.0051 (4) | 0.0008 (4) |
C8 | 0.0152 (5) | 0.0101 (5) | 0.0144 (6) | −0.0008 (4) | 0.0025 (4) | −0.0002 (4) |
N3 | 0.0151 (5) | 0.0098 (5) | 0.0125 (5) | 0.0002 (4) | 0.0038 (4) | 0.0000 (4) |
C6 | 0.0139 (5) | 0.0107 (5) | 0.0108 (5) | −0.0002 (4) | 0.0020 (4) | 0.0005 (4) |
C2 | 0.0135 (5) | 0.0116 (5) | 0.0107 (5) | 0.0004 (4) | 0.0029 (4) | 0.0001 (4) |
C5 | 0.0138 (5) | 0.0109 (5) | 0.0106 (5) | −0.0002 (4) | 0.0021 (4) | 0.0008 (4) |
P1 | 0.0103 (2) | 0.0083 (2) | 0.0110 (2) | 0.0006 (1) | 0.0026 (1) | 0.0004 (1) |
O3 | 0.0110 (4) | 0.0122 (4) | 0.0202 (5) | 0.0003 (3) | −0.0004 (3) | 0.0038 (3) |
O1 | 0.0128 (4) | 0.0126 (4) | 0.0133 (4) | 0.0007 (3) | 0.0051 (3) | −0.0008 (3) |
O2 | 0.0176 (4) | 0.0103 (4) | 0.0142 (4) | 0.0011 (3) | 0.0065 (3) | 0.0022 (3) |
O4 | 0.0156 (4) | 0.0137 (4) | 0.0146 (5) | −0.0012 (3) | 0.0025 (3) | −0.0035 (3) |
O1W | 0.0201 (5) | 0.0114 (4) | 0.0150 (5) | 0.0025 (3) | 0.0044 (4) | −0.0004 (3) |
Geometric parameters (Å, º) top
O6—C6 | 1.2470 (16) | N1—C2 | 1.3798 (16) |
N7—C8 | 1.3205 (17) | N1—C6 | 1.3825 (16) |
N7—C5 | 1.3888 (16) | N3—C2 | 1.3315 (16) |
N9—C8 | 1.3475 (17) | C6—C5 | 1.4165 (18) |
N9—C4 | 1.3762 (16) | P1—O1 | 1.5090 (9) |
N2—C2 | 1.3328 (17) | P1—O2 | 1.5100 (10) |
C4—N3 | 1.3486 (16) | P1—O3 | 1.5717 (10) |
C4—C5 | 1.3870 (17) | P1—O4 | 1.5729 (10) |
| | | |
C8—N7—C5 | 107.29 (11) | N3—C2—N1 | 123.18 (12) |
C8—N9—C4 | 107.55 (11) | N2—C2—N1 | 116.65 (12) |
N3—C4—N9 | 126.00 (11) | C4—C5—N7 | 107.41 (11) |
N3—C4—C5 | 127.23 (12) | C4—C5—C6 | 119.52 (12) |
N9—C4—C5 | 106.74 (11) | N7—C5—C6 | 132.94 (12) |
C2—N1—C6 | 125.20 (11) | O1—P1—O2 | 114.01 (6) |
N7—C8—N9 | 111.01 (12) | O1—P1—O3 | 110.49 (6) |
C2—N3—C4 | 112.99 (11) | O2—P1—O3 | 109.84 (6) |
O6—C6—N1 | 119.32 (12) | O1—P1—O4 | 106.30 (6) |
O6—C6—C5 | 128.84 (12) | O2—P1—O4 | 111.32 (6) |
N1—C6—C5 | 111.83 (11) | O3—P1—O4 | 104.42 (6) |
N3—C2—N2 | 120.17 (12) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(3)—H(3)···O(1)i | 0.90 (3) | 1.67 (3) | 2.567 (1) | 174 (2) |
O(4)—H(4)···O(6)ii | 0.85 (3) | 1.75 (3) | 2.592 (1) | 169 (3) |
N(7)—H(7)···O(2)iii | 0.92 (3) | 1.74 (3) | 2.651 (2) | 173 (3) |
N(9)—H(9)···O(1W)iv | 0.94 (2) | 1.73 (2) | 2.665 (2) | 170 (2) |
O(1W)—H(12)···O(1)v | 0.85 (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)vi | 0.78 (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)vii | 0.82 (2) | 2.20 (2) | 3.016 (2) | 178 (3) |
Symmetry codes: (i) x+1, y, z; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2; (iv) x−1, 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)−·H2O | C5H6N5O+·H2O3P−·2(H2O) | (C5H6N5O1)+·(H2PO4)−·H2O |
Mr | 251.15 | 269.17 | 267.15 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/n |
Temperature (K) | 100 | 100 | 100 |
a, b, c (Å) | 4.9700 (2), 12.7506 (7), 15.0499 (8) | 4.6812 (4), 24.0561 (15), 9.5186 (7 | 4.5414 (3), 12.5774 (6), 18.1485 (9) |
β (°) | 92.293 (4) | 99.773 (7) | 93.689 (5) |
V (Å3) | 952.96 (8) | 1056.35 (14) | 1034.48 (10) |
Z | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.31 | 0.29 | 0.30 |
Crystal size (mm) | 0.40 × 0.15 × 0.10 | 0.60 × 0.15 × 0.10 | 0.42 × 0.10 × 0.07 |
|
Data collection |
Diffractometer | Xcalibur-Saphire2 diffractometer | Xcalibur-Saphire2 diffractometer | Xcalibur-Saphire2 diffractometer |
Absorption correction | Integration Absorb, (DeTitta, 1985) | Integration Absorb, (DeTitta, 1985) | Integration Absorb, (DeTitta, 1985) |
Tmin, Tmax | 0.93, 0.98 | 0.845, 0.972 | 0.87, 0.98 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13648, 2749, 2727 | 31247, 3086, 2911 | 42941, 3013, 2971 |
Rint | 0.041 | 0.040 | 0.063 |
(sin θ/λ)max (Å−1) | 0.702 | 0.703 | 0.703 |
|
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 reflections | 2749 | 3086 | 3013 |
No. of parameters | 185 | 202 | 194 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.62, −0.28 | 0.54, −0.28 | 0.54, −0.38 |
Hydrogen-bond geometry (Å, º) for (GPO3m) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(5)···O(4)i | 0.88 (3) | 1.66 (3) | 2.535 (2) | 177 (3) |
N(7)—H(7)···O(4)ii | 0.92 (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)iii | 0.84 (2) | 1.91 (2) | 2.714 (2) | 160 (2) |
O(1W)—H(12)···O(5)i | 0.88 (3) | 1.88 (3) | 2.755 (2) | 176 (2) |
O(1W)—H(11)···O(6)iv | 0.90 (3) | 1.92 (3) | 2.816 (2) | 172 (3) |
N(2)—H(22)···O(3)iii | 0.84 (3) | 2.24 (3) | 2.967 (2) | 145 (2) |
N(2)—H(21)···N(3)v | 0.88 (2) | 2.14 (2) | 3.022 (2) | 178 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, −y+3/2, z−1/2; (iii) x, y, z−1; (iv) x−1, −y+3/2, z+1/2; (v) −x, −y+1, −z. |
Hydrogen-bond geometry (Å, º) for (GPO3b) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(5)···O(4)i | 0.83 (3) | 1.74 (3) | 2.559 (2) | 173 (4) |
N(7)—H(7)···O(1W)ii | 0.91 (3) | 1.75 (3) | 2.658 (2) | 177 (3) |
N(9)—H(9)···O(3)iii | 0.87 (2) | 1.85 (2) | 2.721 (2) | 172 (2) |
O(1W)—H(11)···O(6)iv | 0.79 (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)v | 0.82 (3) | 2.00 (3) | 2.814 (2) | 170 (3) |
O(2W)—H(23)···O(4)i | 0.83 (3) | 2.07 (3) | 2.874 (2) | 164 (3) |
O(1W)—H(12)···O(4)vi | 0.81 (3) | 2.18 (3) | 2.907 (2) | 151 (3) |
N(2)—H(21)···N(3)iii | 0.88 (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) −x−1, −y, −z+1; (v) x−1, y, z; (vi) −x, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) for (GPO4) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(3)—H(3)···O(1)i | 0.90 (3) | 1.67 (3) | 2.567 (1) | 174 (2) |
O(4)—H(4)···O(6)ii | 0.85 (3) | 1.75 (3) | 2.592 (1) | 169 (3) |
N(7)—H(7)···O(2)iii | 0.92 (3) | 1.74 (3) | 2.651 (2) | 173 (3) |
N(9)—H(9)···O(1W)iv | 0.94 (2) | 1.73 (2) | 2.665 (2) | 170 (2) |
O(1W)—H(12)···O(1)v | 0.85 (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)vi | 0.78 (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)vii | 0.82 (2) | 2.20 (2) | 3.016 (2) | 178 (3) |
Symmetry codes: (i) x+1, y, z; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2; (iv) x−1, y, z; (v) −x+1, −y+1, −z+1; (vi) x, y+1, z; (vii) −x, −y+1, −z+1. |