Crystal structures and phase transitions of imidazolium hypodiphosphates

Two imidazolium hypodiphosphates, (C₃H₅N₂)(H₃P₂O₆) (I) and (C₃H₅N₂)₂(H₂P₂O₆) (II), have been synthesized and structurally characterized. In both metal-free organic–inorganic hybrids (I) and (II), the hypodiphosphate mono- and dianions, (H­₃P₂O₆)⁻ and (H₂P₂O₆)²⁻, form hydrogen-bonded frameworks of different types, to which the organic cations are linked via N—H...O and C—H...O hydrogen bonds. The purity of the compounds was confirmed by powder X-ray diffraction. Differential scanning calorimetry of compound (I) revealed two structural phase transitions: continuous at 311.8 K [cooling/heating; from high-temperature phase (HTP) to room-temperature phase (RTP)] and a discontinuous one at 287.9/289.2 K [RTP → low-temperature phase (LTP)]. Compound (I) is characterized in a wide temperature range by single-crystal and powder X-ray diffraction methods. Crystal structures of high- and low-temperature phases are determined, which show orthorhombic (HTP, Pnna, No. 52) → monoclinic (LTP, P2₁/n11, No. 14, a-axis doubled) structural change on cooling with an intermediate incommensurately modulated phase (RTP). Dynamic properties of polycrystalline (I) were studied by means of dielectric spectroscopy. The dielectric behaviour is explained by the motion of imidazolium cations.

Computing details

For all structures, data collection: CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018); cell refinement: CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018); data reduction: CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018). Program(s) used to solve structure: SHELXT-2014/7 (Sheldrick, 2015) for I-HTP, I_LTP, (II). For all structures, program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015).

(I-HTP)

Crystal data

(C3H5N2)·(H3O6P2)	Dx = 1.811 Mg m^−3
Mr = 230.05	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnna	Cell parameters from 4207 reflections
a = 7.014 (3) Å	θ = 4.7–29.0°
b = 8.361 (3) Å	µ = 0.52 mm^−1
c = 14.389 (5) Å	T = 326 K
V = 843.8 (6) Å^3	Plate, colourless
Z = 4	0.35 × 0.21 × 0.10 mm
F(000) = 472

Data collection

Agilent Technologies, Xcalibur R diffractometer	1134 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	863 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 10.6249 pixels mm^-1	θmax = 29.5°, θmin = 2.8°
ω scans	h = −9→9
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −11→11
Tmin = 0.879, Tmax = 0.960	l = −19→19
12181 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0507P)^2 + 0.2662P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
1134 reflections	Δρmax = 0.22 e Å^−3
101 parameters	Δρmin = −0.31 e Å^−3
64 restraints	Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: dual	Extinction coefficient: 0.065 (5)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1	0.59456 (8)	−0.00006 (5)	0.33491 (3)	0.0431 (2)
O1	0.5287 (3)	0.07335 (14)	0.42605 (9)	0.0594 (4)
H1	0.4973	0.0021	0.4620	0.089*	0.5
O2	0.5307 (2)	−0.17364 (15)	0.32531 (8)	0.0555 (4)
H2	0.5169	−0.1954	0.2702	0.083*	0.5
O3	0.5315 (2)	0.09995 (15)	0.25206 (9)	0.0539 (4)
H3	0.5339	0.1950	0.2661	0.081*	0.5
N1A	0.318 (3)	0.3850 (17)	0.4513 (12)	0.019 (4)*	0.1
H1NA	0.3469	0.2880	0.4373	0.023*	0.1
C2A	0.276 (3)	0.497 (2)	0.3892 (10)	0.023 (4)*	0.1
H2A	0.2699	0.4846	0.3250	0.028*	0.1
N3A	0.245 (4)	0.630 (2)	0.4369 (12)	0.035 (6)*	0.1
H3NA	0.2140	0.7215	0.4135	0.042*	0.1
C4A	0.270 (3)	0.5991 (19)	0.5292 (11)	0.037 (5)*	0.1
H4A	0.2621	0.6739	0.5769	0.045*	0.1
C5A	0.309 (4)	0.442 (2)	0.5402 (11)	0.033 (6)*	0.1
H5A	0.3258	0.3862	0.5954	0.039*	0.1
N1B	0.3068 (14)	0.3895 (9)	0.5180 (6)	0.038 (2)*	0.2
H1NB	0.3314	0.3065	0.5512	0.045*	0.2
C2B	0.2987 (17)	0.3952 (10)	0.4260 (6)	0.039 (3)*	0.2
H2B	0.3185	0.3097	0.3859	0.047*	0.2
N3B	0.2573 (15)	0.5438 (10)	0.4012 (6)	0.034 (2)*	0.2
H3NB	0.2395	0.5753	0.3450	0.041*	0.2
C4B	0.247 (2)	0.6397 (12)	0.4777 (6)	0.058 (4)*	0.2
H4B	0.2295	0.7499	0.4794	0.069*	0.2
C5B	0.2687 (15)	0.5398 (10)	0.5504 (6)	0.033 (3)*	0.2
H5B	0.2591	0.5685	0.6127	0.039*	0.2
N1C	0.212 (2)	0.5834 (16)	0.5399 (7)	0.021 (2)*	0.2
H1NC	0.1745	0.6461	0.5836	0.025*	0.2
C2C	0.254 (2)	0.4299 (17)	0.5503 (8)	0.045 (5)*	0.2
H2C	0.2476	0.3719	0.6054	0.054*	0.2
N3C	0.3059 (18)	0.3738 (11)	0.4679 (7)	0.027 (2)*	0.2
H3NC	0.3395	0.2769	0.4564	0.032*	0.2
C4C	0.2976 (15)	0.4949 (13)	0.4046 (7)	0.025 (2)*	0.2
H4C	0.3281	0.4874	0.3418	0.031*	0.2
C5C	0.237 (3)	0.6272 (14)	0.4492 (9)	0.034 (4)*	0.2
H5C	0.2172	0.7279	0.4235	0.041*	0.2

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0726 (4)	0.0295 (3)	0.0271 (3)	−0.00982 (19)	0.00558 (18)	−0.00153 (16)
O1	0.1093 (12)	0.0349 (7)	0.0339 (7)	0.0028 (7)	0.0159 (7)	−0.0041 (5)
O2	0.0904 (10)	0.0317 (7)	0.0444 (7)	−0.0191 (7)	0.0149 (7)	−0.0047 (5)
O3	0.0817 (9)	0.0471 (7)	0.0328 (6)	−0.0095 (7)	−0.0079 (6)	0.0053 (5)

Geometric parameters (Å, º)

P1—O1	1.5198 (13)	N1B—H1NB	0.8600
P1—O3	1.5219 (13)	C2B—N3B	1.325 (3)
P1—O2	1.5252 (14)	C2B—H2B	0.9300
P1—P1^i	2.1805 (14)	N3B—C4B	1.364 (3)
O1—H1	0.8200	N3B—H3NB	0.8600
O2—H2	0.8200	C4B—C5B	1.347 (3)
O3—H3	0.8200	C4B—H4B	0.9300
N1A—C2A	1.327 (2)	C5B—H5B	0.9300
N1A—C5A	1.368 (2)	N1C—C2C	1.326 (3)
N1A—H1NA	0.8600	N1C—C5C	1.368 (3)
C2A—N3A	1.327 (2)	N1C—H1NC	0.8600
C2A—H2A	0.9300	C2C—N3C	1.326 (3)
N3A—C4A	1.366 (2)	C2C—H2C	0.9300
N3A—H3NA	0.8600	N3C—C4C	1.363 (3)
C4A—C5A	1.348 (2)	N3C—H3NC	0.8600
C4A—H4A	0.9300	C4C—C5C	1.347 (3)
C5A—H5A	0.9300	C4C—H4C	0.9300
N1B—C2B	1.326 (3)	C5C—H5C	0.9300
N1B—C5B	1.367 (3)
O1—P1—O3	111.45 (9)	N3B—C2B—N1B	108.2 (8)
O1—P1—O2	111.91 (7)	N3B—C2B—H2B	125.9
O3—P1—O2	111.50 (8)	N1B—C2B—H2B	125.9
O1—P1—P1^i	107.67 (7)	C2B—N3B—C4B	110.2 (9)
O3—P1—P1^i	106.89 (6)	C2B—N3B—H3NB	124.9
O2—P1—P1^i	107.11 (7)	C4B—N3B—H3NB	124.9
P1—O1—H1	109.5	C5B—C4B—N3B	104.9 (8)
P1—O2—H2	109.5	C5B—C4B—H4B	127.6
P1—O3—H3	109.5	N3B—C4B—H4B	127.6
C2A—N1A—C5A	111.8 (12)	C4B—C5B—N1B	109.1 (7)
C2A—N1A—H1NA	124.1	C4B—C5B—H5B	125.5
C5A—N1A—H1NA	124.1	N1B—C5B—H5B	125.5
N3A—C2A—N1A	106.4 (12)	C2C—N1C—C5C	109.8 (10)
N3A—C2A—H2A	126.8	C2C—N1C—H1NC	125.1
N1A—C2A—H2A	126.8	C5C—N1C—H1NC	125.1
C2A—N3A—C4A	108.7 (11)	N1C—C2C—N3C	107.6 (10)
C2A—N3A—H3NA	125.7	N1C—C2C—H2C	126.2
C4A—N3A—H3NA	125.7	N3C—C2C—H2C	126.2
C5A—C4A—N3A	109.1 (11)	C2C—N3C—C4C	108.9 (8)
C5A—C4A—H4A	125.5	C2C—N3C—H3NC	125.6
N3A—C4A—H4A	125.5	C4C—N3C—H3NC	125.6
C4A—C5A—N1A	103.9 (11)	C5C—C4C—N3C	107.8 (8)
C4A—C5A—H5A	128.1	C5C—C4C—H4C	126.1
N1A—C5A—H5A	128.1	N3C—C4C—H4C	126.1
C2B—N1B—C5B	107.4 (7)	C4C—C5C—N1C	106.0 (9)
C2B—N1B—H1NB	126.3	C4C—C5C—H5C	127.0
C5B—N1B—H1NB	126.3	N1C—C5C—H5C	127.0
C5A—N1A—C2A—N3A	1.8 (10)	C2C—N3C—C4C—C5C	−0.6 (14)
N1A—C2A—N3A—C4A	0.7 (10)	N3C—C4C—C5C—N1C	0.6 (15)
C2A—N3A—C4A—C5A	−2.9 (16)	C2C—N1C—C5C—C4C	−0.4 (13)
N3A—C4A—C5A—N1A	3.8 (18)	O1—P1—P1^i—O1^i	50.17 (11)
C2A—N1A—C5A—C4A	−3.5 (15)	O2—P1—P1^i—O1^i	−70.35 (7)
C5B—N1B—C2B—N3B	0.1 (8)	O3—P1—P1^i—O1^i	170.03 (7)
N1B—C2B—N3B—C4B	3.0 (8)	O1—P1—P1^i—O2^i	−70.35 (7)
C2B—N3B—C4B—C5B	−4.9 (11)	O2—P1—P1^i—O2^i	169.13 (10)
N3B—C4B—C5B—N1B	4.9 (12)	O3—P1—P1^i—O2^i	49.51 (7)
C2B—N1B—C5B—C4B	−3.3 (11)	O1—P1—P1^i—O3^i	170.03 (7)
C5C—N1C—C2C—N3C	0.1 (9)	O2—P1—P1^i—O3^i	49.51 (7)
N1C—C2C—N3C—C4C	0.3 (9)	O3—P1—P1^i—O3^i	−70.11 (11)

Symmetry code: (i) −x+3/2, −y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1^ii	0.82	1.74	2.489 (3)	151
O2—H2···O2^iii	0.82	1.76	2.516 (2)	153
O3—H3···O3^iv	0.82	1.73	2.510 (3)	157
N1A—H1NA···O1	0.86	2.21	3.018 (14)	157
N3A—H3NA···O1^v	0.86	2.42	3.138 (18)	141
N1B—H1NB···O2^ii	0.86	2.31	3.105 (8)	154
N3B—H3NB···O3^vi	0.86	2.37	3.031 (9)	134
N1C—H1NC···O2^vii	0.86	2.24	3.083 (11)	168
N3C—H3NC···O1	0.86	2.20	3.019 (10)	159
C2A—H2A···O3^iv	0.93	2.26	2.828 (19)	119
C4A—H4A···O1^viii	0.93	2.57	3.147 (17)	120
C4A—H4A···O2^vii	0.93	2.50	3.289 (17)	143
C5A—H5A···O2^ii	0.93	2.34	3.171 (18)	149
C2B—H2B···O1	0.93	2.53	3.138 (9)	123
C4B—H4B···O1^v	0.93	2.46	3.171 (12)	133
C5B—H5B···O3^ix	0.93	2.50	3.261 (9)	139
C2C—H2C···O2^ii	0.93	2.48	3.175 (13)	131
C2C—H2C···O3^x	0.93	2.61	3.305 (12)	132
C4C—H4C···O3^iv	0.93	2.10	2.898 (10)	144
C5C—H5C···O1^v	0.93	2.40	3.141 (13)	137

Symmetry codes: (ii) −x+1, −y, −z+1; (iii) x, −y−1/2, −z+1/2; (iv) x, −y+1/2, −z+1/2; (v) −x+1/2, −y+1, z; (vi) −x+1/2, y+1/2, −z+1/2; (vii) x−1/2, y+1, −z+1; (viii) −x+1, −y+1, −z+1; (ix) −x+1, y+1/2, z+1/2; (x) x−1/2, −y+1/2, z+1/2.

(I_RTP)

Crystal data

(C3H5N2)·(H3O6P2)	Dx = 1.823 Mg m^−3
Mr = 230.05	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnna	Cell parameters from 4526 reflections
a = 6.962 (3) Å	θ = 4.7–29.1°
b = 8.368 (3) Å	µ = 0.52 mm^−1
c = 14.388 (4) Å	T = 291 K
V = 838.2 (5) Å^3	Plate, colourless
Z = 4	0.35 × 0.21 × 0.10 mm
F(000) = 472

Data collection

Agilent Technologies, Xcalibur R diffractometer	1128 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	901 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 10.6249 pixels mm^-1	θmax = 29.2°, θmin = 2.8°
ω scans	h = −9→9
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −11→11
Tmin = 0.868, Tmax = 0.957	l = −19→19
12065 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0419P)^2 + 0.4756P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1128 reflections	Δρmax = 0.24 e Å^−3
101 parameters	Δρmin = −0.39 e Å^−3
35 restraints	Extinction correction: SHELXL-2014/7 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: isomorphous structure methods	Extinction coefficient: 0.065 (4)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1	0.59322 (8)	0.00009 (5)	0.33478 (3)	0.0410 (2)
O1	0.5268 (3)	0.07328 (15)	0.42589 (9)	0.0537 (4)
H1	0.514694	0.002730	0.465006	0.081*	0.5
O2	0.5286 (3)	−0.17341 (16)	0.32510 (9)	0.0524 (4)
H2	0.522141	−0.196980	0.269866	0.079*	0.5
O3	0.5298 (2)	0.10050 (16)	0.25196 (9)	0.0509 (4)
H3	0.536109	0.195536	0.265515	0.076*	0.5
N1A	0.315 (4)	0.3899 (19)	0.4357 (10)	0.018 (5)*	0.1
H1A	0.341530	0.301228	0.408235	0.022*	0.1
C2A	0.262 (4)	0.519 (2)	0.3881 (10)	0.014 (4)*	0.1
H2A	0.240136	0.530347	0.324739	0.017*	0.1
N3A	0.249 (5)	0.626 (2)	0.4558 (12)	0.042 (11)*	0.1
H3A	0.222872	0.725672	0.446907	0.051*	0.1
C4A	0.282 (4)	0.5602 (19)	0.5414 (12)	0.027 (6)*	0.1
H4A	0.273958	0.613810	0.597862	0.033*	0.1
C5A	0.327 (3)	0.405 (2)	0.5304 (10)	0.010 (3)*	0.1
H5A	0.357571	0.328163	0.574925	0.012*	0.1
N1B	0.285 (2)	0.3941 (11)	0.5211 (7)	0.036 (3)*	0.2
H1B	0.309717	0.313912	0.556397	0.044*	0.2
C2B	0.268 (2)	0.3814 (9)	0.4293 (7)	0.029 (3)*	0.2
H2B	0.286994	0.292095	0.391904	0.035*	0.2
N3B	0.2177 (18)	0.5286 (9)	0.4046 (6)	0.024 (3)*	0.2
H3B	0.201627	0.558654	0.348010	0.028*	0.2
C4B	0.194 (2)	0.6268 (14)	0.4798 (7)	0.036 (3)*	0.2
H4B	0.143740	0.729692	0.479366	0.043*	0.2
C5B	0.259 (3)	0.5459 (12)	0.5546 (8)	0.038 (4)*	0.2
H5B	0.280296	0.583857	0.614431	0.046*	0.2
N1C	0.212 (3)	0.5622 (16)	0.5424 (8)	0.027 (3)*	0.2
H1C	0.165905	0.609116	0.590781	0.033*	0.2
C2C	0.274 (2)	0.4121 (16)	0.5447 (8)	0.018 (3)*	0.2
H2C	0.288262	0.344285	0.595466	0.022*	0.2
N3C	0.311 (3)	0.3842 (15)	0.4554 (8)	0.022 (3)*	0.2
H3C	0.343391	0.292508	0.433545	0.026*	0.2
C4C	0.290 (2)	0.5190 (15)	0.4027 (8)	0.027 (3)*	0.2
H4C	0.315575	0.527623	0.339451	0.032*	0.2
C5C	0.225 (3)	0.6374 (14)	0.4580 (10)	0.021 (4)*	0.2
H5C	0.196349	0.742762	0.442819	0.025*	0.2

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0685 (4)	0.0304 (3)	0.0240 (3)	−0.0146 (2)	0.00466 (19)	−0.00231 (17)
O1	0.1012 (12)	0.0316 (7)	0.0283 (7)	−0.0010 (7)	0.0124 (7)	−0.0036 (5)
O2	0.0860 (11)	0.0316 (7)	0.0394 (7)	−0.0218 (7)	0.0148 (7)	−0.0052 (5)
O3	0.0763 (9)	0.0488 (8)	0.0276 (6)	−0.0128 (7)	−0.0064 (6)	0.0044 (5)

Geometric parameters (Å, º)

P1—O1	1.5190 (13)	N1B—H1B	0.8600
P1—O3	1.5234 (14)	C2B—N3B	1.330 (3)
P1—O2	1.5263 (14)	C2B—H2B	0.9300
P1—P1^i	2.1831 (15)	N3B—C4B	1.368 (3)
O1—H1	0.8200	N3B—H3B	0.8600
O2—H2	0.8200	C4B—C5B	1.348 (3)
O3—H3	0.8200	C4B—H4B	0.9300
N1A—C2A	1.330 (2)	C5B—H5B	0.9300
N1A—C5A	1.370 (2)	N1C—C2C	1.330 (3)
N1A—H1A	0.8600	N1C—C5C	1.371 (3)
C2A—N3A	1.330 (2)	N1C—H1C	0.8600
C2A—H2A	0.9300	C2C—N3C	1.330 (3)
N3A—C4A	1.369 (2)	C2C—H2C	0.9300
N3A—H3A	0.8600	N3C—C4C	1.368 (3)
C4A—C5A	1.349 (2)	N3C—H3C	0.8600
C4A—H4A	0.9300	C4C—C5C	1.348 (3)
C5A—H5A	0.9300	C4C—H4C	0.9300
N1B—C2B	1.329 (3)	C5C—H5C	0.9300
N1B—C5B	1.370 (3)
O1—P1—O3	111.37 (9)	N1B—C2B—N3B	102.3 (9)
O1—P1—O2	111.87 (8)	N1B—C2B—H2B	128.8
O3—P1—O2	111.58 (8)	N3B—C2B—H2B	128.8
O1—P1—P1^i	107.74 (7)	C2B—N3B—C4B	112.2 (10)
O3—P1—P1^i	106.87 (6)	C2B—N3B—H3B	123.9
O2—P1—P1^i	107.10 (8)	C4B—N3B—H3B	123.9
P1—O1—H1	109.5	C5B—C4B—N3B	106.8 (10)
P1—O2—H2	109.5	C5B—C4B—H4B	126.6
P1—O3—H3	109.5	N3B—C4B—H4B	126.6
C2A—N1A—C5A	117.1 (12)	C4B—C5B—N1B	103.2 (10)
C2A—N1A—H1A	121.5	C4B—C5B—H5B	128.4
C5A—N1A—H1A	121.5	N1B—C5B—H5B	128.4
N1A—C2A—N3A	101.1 (12)	C2C—N1C—C5C	115.7 (12)
N1A—C2A—H2A	129.5	C2C—N1C—H1C	122.2
N3A—C2A—H2A	129.5	C5C—N1C—H1C	122.2
C2A—N3A—C4A	111.9 (13)	N1C—C2C—N3C	101.8 (11)
C2A—N3A—H3A	124.1	N1C—C2C—H2C	129.1
C4A—N3A—H3A	124.1	N3C—C2C—H2C	129.1
C5A—C4A—N3A	108.9 (13)	C2C—N3C—C4C	111.8 (9)
C5A—C4A—H4A	125.5	C2C—N3C—H3C	124.1
N3A—C4A—H4A	125.5	C4C—N3C—H3C	124.1
C4A—C5A—N1A	100.9 (12)	C5C—C4C—N3C	108.3 (9)
C4A—C5A—H5A	129.5	C5C—C4C—H4C	125.9
N1A—C5A—H5A	129.5	N3C—C4C—H4C	125.9
C2B—N1B—C5B	114.4 (9)	C4C—C5C—N1C	102.0 (10)
C2B—N1B—H1B	122.8	C4C—C5C—H5C	129.0
C5B—N1B—H1B	122.8	N1C—C5C—H5C	129.0
C5A—N1A—C2A—N3A	4 (3)	C2C—N3C—C4C—C5C	−4 (2)
N1A—C2A—N3A—C4A	−4 (4)	N3C—C4C—C5C—N1C	0.1 (18)
C2A—N3A—C4A—C5A	3 (4)	C2C—N1C—C5C—C4C	4.1 (19)
N3A—C4A—C5A—N1A	−1 (3)	O1—P1—P1^i—O1^i	50.06 (11)
C2A—N1A—C5A—C4A	−2 (3)	O2—P1—P1^i—O1^i	−70.45 (7)
C5B—N1B—C2B—N3B	−3.9 (16)	O3—P1—P1^i—O1^i	169.85 (8)
N1B—C2B—N3B—C4B	−3.1 (14)	O1—P1—P1^i—O2^i	−70.45 (7)
C2B—N3B—C4B—C5B	8.9 (18)	O2—P1—P1^i—O2^i	169.04 (10)
N3B—C4B—C5B—N1B	−10.3 (19)	O3—P1—P1^i—O2^i	49.34 (8)
C2B—N1B—C5B—C4B	9 (2)	O1—P1—P1^i—O3^i	169.85 (8)
C5C—N1C—C2C—N3C	−6.4 (19)	O2—P1—P1^i—O3^i	49.34 (8)
N1C—C2C—N3C—C4C	6.2 (18)	O3—P1—P1^i—O3^i	−70.36 (12)

Symmetry code: (i) −x+3/2, −y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1^ii	0.82	1.72	2.488 (3)	156
O2—H2···O2^iii	0.82	1.75	2.513 (2)	155
O3—H3···O3^iv	0.82	1.73	2.503 (3)	157
N1A—H1A···O1	0.86	2.32	3.034 (17)	141
N3A—H3A···O1^v	0.86	2.44	3.19 (2)	147
N1B—H1B···O2^ii	0.86	2.36	3.162 (11)	156
N3B—H3B···O3^vi	0.86	2.19	2.900 (9)	140
N1C—H1C···O2^vii	0.86	2.39	3.186 (13)	155
N3C—H3C···O1	0.86	2.24	3.036 (12)	154
C2A—H2A···O3^vi	0.93	2.26	2.94 (2)	130
C4A—H4A···O3^viii	0.93	2.61	3.32 (2)	134
C5A—H5A···O2^ii	0.93	2.09	3.013 (14)	171
C2B—H2B···O1	0.93	2.53	3.145 (9)	124
C4B—H4B···O1^v	0.93	2.17	3.044 (12)	156
C5B—H5B···O3^viii	0.93	2.38	3.231 (13)	151
C2C—H2C···O2^ii	0.93	2.23	3.064 (14)	149
C4C—H4C···O3^iv	0.93	2.26	2.957 (14)	131
C5C—H5C···O1^v	0.93	2.20	3.024 (15)	147

Symmetry codes: (ii) −x+1, −y, −z+1; (iii) x, −y−1/2, −z+1/2; (iv) x, −y+1/2, −z+1/2; (v) −x+1/2, −y+1, z; (vi) −x+1/2, y+1/2, −z+1/2; (vii) x−1/2, y+1, −z+1; (viii) −x+1, y+1/2, z+1/2.

(I_LTP)

Crystal data

(C3H5N2)·(H3O6P2)	F(000) = 944
Mr = 230.05	Dx = 1.860 Mg m^−3
Monoclinic, P21/n11	Mo Kα radiation, λ = 0.71073 Å
a = 13.673 (2) Å	Cell parameters from 6843 reflections
b = 8.396 (2) Å	θ = 2.8–29.3°
c = 14.317 (3) Å	µ = 0.53 mm^−1
β = 90°	T = 100 K
V = 1643.5 (6) Å^3	Plate, colourless
Z = 8	0.35 × 0.21 × 0.10 mm

Data collection

Agilent Technologies, Xcalibur R diffractometer	4008 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	3358 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 10.6249 pixels mm^-1	θmax = 29.5°, θmin = 2.8°
ω scans	h = −18→17
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −11→10
Tmin = 0.868, Tmax = 0.952	l = −18→18
14185 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0355P)^2 + 1.1991P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4008 reflections	Δρmax = 0.43 e Å^−3
245 parameters	Δρmin = −0.47 e Å^−3
5 restraints	Extinction correction: SHELXL-2014/7 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: dual	Extinction coefficient: 0.0049 (3)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1A	0.28745 (3)	0.01736 (5)	0.33674 (3)	0.00790 (11)
P2A	0.44733 (3)	0.01986 (5)	0.33894 (3)	0.00804 (11)
O1A	0.25123 (9)	0.09237 (13)	0.42644 (8)	0.0109 (3)
O2A	0.25705 (9)	0.10470 (14)	0.24807 (8)	0.0108 (3)
O3A	0.25329 (9)	−0.15954 (13)	0.33107 (9)	0.0120 (3)
H3A	0.2625	−0.2064	0.2797	0.066 (10)*
O4A	0.47699 (9)	0.19232 (13)	0.33225 (8)	0.0107 (3)
O5A	0.48196 (9)	−0.06658 (14)	0.42585 (8)	0.0122 (3)
H5A	0.5000	0.0000	0.5000	0.082 (16)*
O6A	0.48091 (9)	−0.07278 (14)	0.24998 (8)	0.0117 (3)
H6A	0.4847	−0.1724	0.2537	0.069 (10)*
P1B	0.31216 (3)	0.50861 (5)	0.16782 (3)	0.00846 (11)
P2B	0.47219 (3)	0.51986 (5)	0.16949 (3)	0.00814 (11)
O1B	0.27275 (9)	0.67343 (13)	0.18213 (8)	0.0114 (3)
O2B	0.28276 (9)	0.39351 (14)	0.24509 (8)	0.0121 (3)
H2B	0.275 (3)	0.263 (4)	0.242 (2)	0.079 (11)*
O3B	0.28407 (9)	0.43198 (14)	0.07219 (8)	0.0124 (3)
H3B	0.2763	0.4955	0.0279	0.057 (9)*
O4B	0.50262 (9)	0.62797 (14)	0.24819 (8)	0.0114 (3)
O5B	0.50603 (9)	0.57711 (14)	0.07341 (8)	0.0113 (3)
H5B	0.5088	0.5162	0.0266	0.017*	0.5
O6B	0.50977 (9)	0.34540 (14)	0.18031 (9)	0.0117 (3)
H6B	0.5014	0.3034	0.2327	0.074 (11)*
N1A	0.15762 (11)	0.38999 (17)	0.45119 (10)	0.0123 (3)
H1NA	0.1801	0.2971	0.4318	0.015*
N3A	0.10820 (11)	0.63204 (17)	0.45115 (11)	0.0125 (3)
H3NA	0.0923	0.7277	0.4318	0.015*
C2A	0.14201 (13)	0.5153 (2)	0.39745 (13)	0.0136 (4)
H2AA	0.1531	0.5203	0.3320	0.016*
C4A	0.10181 (13)	0.5810 (2)	0.54167 (12)	0.0121 (4)
H4A	0.0797	0.6414	0.5940	0.015*
C5A	0.13314 (13)	0.4282 (2)	0.54205 (13)	0.0127 (4)
H5AA	0.1374	0.3604	0.5946	0.015*
N1B	0.40281 (11)	0.40332 (17)	0.46499 (10)	0.0119 (3)
H1NB	0.4246	0.3331	0.4239	0.014*
N3B	0.35492 (11)	0.50904 (17)	0.59381 (11)	0.0137 (3)
H3NB	0.3394	0.5212	0.6531	0.016*
C2B	0.38577 (13)	0.3749 (2)	0.55451 (13)	0.0141 (4)
H2BA	0.3942	0.2758	0.5850	0.017*
C4B	0.35081 (13)	0.6264 (2)	0.52792 (13)	0.0127 (4)
H4B	0.3306	0.7335	0.5376	0.015*
C5B	0.38112 (13)	0.5599 (2)	0.44651 (13)	0.0128 (4)
H5BA	0.3864	0.6114	0.3879	0.015*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1A	0.0103 (2)	0.0068 (2)	0.0067 (2)	−0.00010 (16)	0.00073 (17)	0.00033 (14)
P2A	0.0102 (2)	0.0067 (2)	0.0072 (2)	0.00057 (15)	0.00022 (17)	0.00017 (15)
O1A	0.0137 (6)	0.0100 (6)	0.0091 (6)	0.0018 (5)	0.0026 (5)	−0.0007 (4)
O2A	0.0140 (7)	0.0102 (6)	0.0082 (6)	−0.0020 (5)	−0.0019 (5)	0.0019 (4)
O3A	0.0164 (7)	0.0081 (6)	0.0117 (6)	−0.0023 (5)	0.0024 (5)	0.0000 (4)
O4A	0.0134 (6)	0.0081 (6)	0.0107 (6)	−0.0011 (5)	0.0003 (5)	−0.0007 (4)
O5A	0.0172 (7)	0.0104 (6)	0.0091 (6)	0.0022 (5)	−0.0032 (5)	0.0002 (4)
O6A	0.0167 (7)	0.0088 (6)	0.0096 (6)	0.0014 (5)	0.0022 (5)	−0.0014 (4)
P1B	0.0107 (2)	0.0068 (2)	0.0079 (2)	−0.00058 (16)	0.00009 (17)	−0.00017 (15)
P2B	0.0108 (2)	0.0068 (2)	0.0069 (2)	−0.00064 (16)	0.00065 (17)	−0.00094 (15)
O1B	0.0145 (6)	0.0083 (6)	0.0114 (6)	0.0014 (5)	−0.0005 (5)	−0.0002 (4)
O2B	0.0162 (7)	0.0099 (6)	0.0103 (6)	−0.0013 (5)	0.0025 (5)	0.0010 (4)
O3B	0.0186 (7)	0.0095 (6)	0.0089 (6)	−0.0018 (5)	−0.0030 (5)	−0.0005 (4)
O4B	0.0147 (6)	0.0095 (6)	0.0101 (6)	−0.0011 (5)	−0.0015 (5)	−0.0022 (4)
O5B	0.0165 (7)	0.0096 (6)	0.0078 (6)	−0.0029 (5)	0.0023 (5)	−0.0001 (4)
O6B	0.0151 (7)	0.0084 (6)	0.0117 (6)	0.0010 (5)	0.0022 (5)	0.0005 (5)
N1A	0.0116 (7)	0.0094 (7)	0.0160 (8)	0.0021 (6)	−0.0008 (6)	−0.0032 (5)
N3A	0.0122 (8)	0.0092 (7)	0.0164 (8)	0.0013 (6)	−0.0004 (6)	0.0030 (5)
C2A	0.0112 (9)	0.0177 (9)	0.0119 (9)	0.0002 (7)	0.0005 (7)	0.0000 (7)
C4A	0.0126 (9)	0.0137 (8)	0.0100 (9)	−0.0009 (7)	0.0014 (7)	−0.0021 (6)
C5A	0.0126 (9)	0.0136 (8)	0.0119 (9)	−0.0007 (7)	−0.0020 (7)	0.0029 (6)
N1B	0.0120 (8)	0.0105 (7)	0.0130 (8)	0.0005 (6)	0.0013 (6)	−0.0042 (5)
N3B	0.0160 (8)	0.0161 (8)	0.0089 (7)	0.0000 (6)	0.0030 (6)	−0.0014 (6)
C2B	0.0132 (9)	0.0122 (8)	0.0170 (9)	0.0003 (7)	−0.0012 (7)	0.0020 (7)
C4B	0.0121 (9)	0.0101 (8)	0.0159 (9)	0.0012 (7)	−0.0014 (7)	−0.0008 (6)
C5B	0.0148 (9)	0.0128 (8)	0.0109 (9)	−0.0012 (7)	−0.0009 (7)	0.0024 (6)

Geometric parameters (Å, º)

P1A—O1A	1.5083 (12)	O6B—H6B	0.8400
P1A—O2A	1.5299 (13)	N1A—C2A	1.327 (2)
P1A—O3A	1.5583 (12)	N1A—C5A	1.378 (2)
P1A—P2A	2.1863 (7)	N1A—H1NA	0.8800
P2A—O4A	1.5077 (12)	N3A—C2A	1.323 (2)
P2A—O5A	1.5222 (13)	N3A—C4A	1.372 (2)
P2A—O6A	1.5551 (12)	N3A—H3NA	0.8800
O2A—H2B	1.35 (3)	C2A—H2AA	0.9500
O3A—H3A	0.8403	C4A—C5A	1.353 (2)
O5A—H5A	1.220 (2)	C4A—H4A	0.9500
O6A—H6A	0.8404	C5A—H5AA	0.9500
P1B—O1B	1.4972 (12)	N1B—C2B	1.327 (2)
P1B—O2B	1.5299 (13)	N1B—C5B	1.376 (2)
P1B—O3B	1.5551 (12)	N1B—H1NB	0.8800
P1B—P2B	2.1902 (7)	N3B—C2B	1.323 (2)
P2B—O4B	1.4987 (12)	N3B—C4B	1.372 (2)
P2B—O5B	1.5331 (13)	N3B—H3NB	0.8800
P2B—O6B	1.5614 (13)	C2B—H2BA	0.9500
O2B—H2B	1.10 (3)	C4B—C5B	1.352 (2)
O3B—H3B	0.8402	C4B—H4B	0.9500
O5B—H5B	0.8400	C5B—H5BA	0.9500
O1A—P1A—O2A	114.69 (7)	P2B—O6B—H6B	116.5
O1A—P1A—O3A	109.61 (7)	C2A—N1A—C5A	109.27 (15)
O2A—P1A—O3A	109.86 (7)	C2A—N1A—H1NA	125.4
O1A—P1A—P2A	108.19 (5)	C5A—N1A—H1NA	125.4
O2A—P1A—P2A	106.20 (5)	C2A—N3A—C4A	109.56 (15)
O3A—P1A—P2A	108.03 (5)	C2A—N3A—H3NA	125.2
O4A—P2A—O5A	115.74 (7)	C4A—N3A—H3NA	125.2
O4A—P2A—O6A	109.96 (7)	N3A—C2A—N1A	107.85 (16)
O5A—P2A—O6A	109.81 (7)	N3A—C2A—H2AA	126.1
O4A—P2A—P1A	106.09 (5)	N1A—C2A—H2AA	126.1
O5A—P2A—P1A	108.55 (6)	C5A—C4A—N3A	106.77 (15)
O6A—P2A—P1A	106.19 (5)	C5A—C4A—H4A	126.6
P1A—O2A—H2B	118.9 (13)	N3A—C4A—H4A	126.6
P1A—O3A—H3A	116.0	C4A—C5A—N1A	106.55 (16)
P2A—O5A—H5A	123.79 (9)	C4A—C5A—H5AA	126.7
P2A—O6A—H6A	117.1	N1A—C5A—H5AA	126.7
O1B—P1B—O2B	113.34 (7)	C2B—N1B—C5B	109.23 (15)
O1B—P1B—O3B	113.91 (7)	C2B—N1B—H1NB	125.4
O2B—P1B—O3B	108.24 (7)	C5B—N1B—H1NB	125.4
O1B—P1B—P2B	108.56 (5)	C2B—N3B—C4B	109.55 (15)
O2B—P1B—P2B	106.38 (5)	C2B—N3B—H3NB	125.2
O3B—P1B—P2B	105.89 (5)	C4B—N3B—H3NB	125.2
O4B—P2B—O5B	113.44 (7)	N3B—C2B—N1B	107.83 (16)
O4B—P2B—O6B	113.32 (7)	N3B—C2B—H2BA	126.1
O5B—P2B—O6B	107.01 (7)	N1B—C2B—H2BA	126.1
O4B—P2B—P1B	108.13 (5)	C5B—C4B—N3B	106.70 (15)
O5B—P2B—P1B	107.79 (5)	C5B—C4B—H4B	126.7
O6B—P2B—P1B	106.82 (5)	N3B—C4B—H4B	126.7
P1B—O2B—H2B	129.2 (16)	C4B—C5B—N1B	106.69 (16)
P1B—O3B—H3B	115.9	C4B—C5B—H5BA	126.7
P2B—O5B—H5B	122.4	N1B—C5B—H5BA	126.7
O1A—P1A—P2A—O4A	−68.32 (7)	O3B—P1B—P2B—O5B	43.13 (7)
O2A—P1A—P2A—O4A	55.28 (7)	O1B—P1B—P2B—O6B	165.73 (7)
O3A—P1A—P2A—O4A	173.10 (7)	O2B—P1B—P2B—O6B	43.43 (7)
O1A—P1A—P2A—O5A	56.68 (7)	O3B—P1B—P2B—O6B	−71.58 (7)
O2A—P1A—P2A—O5A	−179.72 (7)	C4A—N3A—C2A—N1A	0.0 (2)
O3A—P1A—P2A—O5A	−61.90 (7)	C5A—N1A—C2A—N3A	−0.1 (2)
O1A—P1A—P2A—O6A	174.70 (7)	C2A—N3A—C4A—C5A	0.1 (2)
O2A—P1A—P2A—O6A	−61.70 (7)	N3A—C4A—C5A—N1A	−0.2 (2)
O3A—P1A—P2A—O6A	56.11 (7)	C2A—N1A—C5A—C4A	0.2 (2)
O1B—P1B—P2B—O4B	43.44 (8)	C4B—N3B—C2B—N1B	0.7 (2)
O2B—P1B—P2B—O4B	−78.85 (8)	C5B—N1B—C2B—N3B	−0.7 (2)
O3B—P1B—P2B—O4B	166.13 (7)	C2B—N3B—C4B—C5B	−0.5 (2)
O1B—P1B—P2B—O5B	−79.56 (7)	N3B—C4B—C5B—N1B	0.1 (2)
O2B—P1B—P2B—O5B	158.14 (7)	C2B—N1B—C5B—C4B	0.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3A—H3A···O1B^i	0.84	1.72	2.5544 (18)	171
O5A—H5A···O5A^ii	1.22 (1)	1.22 (1)	2.440 (2)	180
O6A—H6A···O4B^i	0.84	1.69	2.5298 (18)	172
O2B—H2B···O2A	1.10 (3)	1.35 (3)	2.4510 (18)	172 (3)
O3B—H3B···O1A^iii	0.84	1.71	2.5410 (19)	168
O5B—H5B···O5B^iv	0.84	1.64	2.463 (2)	167
O6B—H6B···O4A	0.84	1.74	2.5769 (19)	172
N1A—H1NA···O1A	0.88	1.98	2.8267 (19)	162
N3A—H3NA···O5B^v	0.88	2.02	2.8382 (19)	154
N1B—H1NB···O4A	0.88	1.90	2.7770 (19)	176
N3B—H3NB···O2A^vi	0.88	2.02	2.7985 (19)	148
C2A—H2AA···O2B	0.95	2.41	3.076 (2)	127
C4A—H4A···O6B^vi	0.95	2.43	3.333 (2)	158
C5A—H5AA···O1B^vii	0.95	2.36	3.215 (2)	149
C2B—H2BA···O5A^ii	0.95	2.44	3.173 (2)	133
C4B—H4B···O3B^vi	0.95	2.34	3.218 (2)	154
C5B—H5BA···O4B	0.95	2.56	3.344 (2)	140

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y, −z+1; (iii) −x+1/2, y+1/2, z−1/2; (iv) −x+1, −y+1, −z; (v) x−1/2, −y+3/2, −z+1/2; (vi) −x+1/2, y+1/2, z+1/2; (vii) −x+1/2, y−1/2, z+1/2.

(II)

Crystal data

2(C3H5N2)·(H2O6P2)	Dx = 1.593 Mg m^−3
Mr = 298.14	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43212	Cell parameters from 5341 reflections
a = 8.966 (2) Å	θ = 2.6–28.4°
c = 15.462 (4) Å	µ = 0.38 mm^−1
V = 1243.0 (6) Å^3	T = 110 K
Z = 4	Column, colourless
F(000) = 616	0.42 × 0.06 × 0.05 mm

Data collection

Agilent Technologies, Xcalibur R diffractometer	1550 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	1444 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 10.3456 pixels mm^-1	θmax = 28.8°, θmin = 2.6°
ω scans	h = −11→11
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −11→10
Tmin = 0.867, Tmax = 0.983	l = −20→19
13584 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.065	w = 1/[σ^2(Fo^2) + (0.0313P)^2 + 0.3895P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
1550 reflections	Δρmax = 0.30 e Å^−3
94 parameters	Δρmin = −0.30 e Å^−3
0 restraints	Absolute structure: Flack x determined using 519 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: dual	Absolute structure parameter: 0.03 (4)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.31970 (6)	0.24790 (6)	0.56384 (3)	0.01203 (14)
O1	0.29901 (18)	0.08245 (17)	0.57054 (11)	0.0214 (4)
O2	0.47546 (16)	0.30850 (17)	0.57853 (10)	0.0161 (3)
O3	0.21351 (18)	0.33388 (19)	0.62805 (10)	0.0189 (4)
H3	0.131 (4)	0.288 (4)	0.635 (2)	0.054 (11)*
N1	0.4969 (2)	0.6045 (2)	0.61837 (13)	0.0187 (4)
H1N	0.493 (4)	0.518 (4)	0.606 (2)	0.038 (9)*
N3	0.4378 (2)	0.8365 (2)	0.61309 (13)	0.0189 (4)
H3N	0.401 (4)	0.911 (4)	0.599 (2)	0.046 (10)*
C2	0.4252 (3)	0.7072 (2)	0.57305 (15)	0.0195 (5)
H2	0.3733	0.6906	0.5204	0.023*
C4	0.5189 (2)	0.8159 (3)	0.68759 (16)	0.0196 (5)
H4	0.5442	0.8902	0.7288	0.024*
C5	0.5557 (2)	0.6700 (2)	0.69101 (15)	0.0187 (4)
H5	0.6115	0.6220	0.7352	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0132 (3)	0.0100 (3)	0.0128 (2)	−0.0007 (2)	−0.0022 (2)	0.0010 (2)
O1	0.0240 (9)	0.0120 (7)	0.0281 (9)	−0.0015 (6)	−0.0086 (7)	0.0037 (7)
O2	0.0146 (8)	0.0151 (7)	0.0188 (8)	−0.0008 (6)	−0.0040 (6)	0.0010 (6)
O3	0.0188 (8)	0.0208 (9)	0.0170 (8)	−0.0051 (7)	0.0040 (6)	−0.0033 (6)
N1	0.0191 (10)	0.0135 (10)	0.0236 (10)	0.0007 (7)	0.0005 (8)	−0.0021 (8)
N3	0.0217 (10)	0.0127 (10)	0.0225 (10)	0.0030 (8)	−0.0044 (8)	0.0001 (8)
C2	0.0203 (11)	0.0181 (11)	0.0200 (11)	0.0009 (8)	−0.0032 (9)	−0.0025 (8)
C4	0.0201 (11)	0.0172 (11)	0.0216 (11)	0.0001 (9)	−0.0037 (10)	−0.0027 (10)
C5	0.0181 (10)	0.0177 (11)	0.0201 (10)	−0.0006 (9)	−0.0023 (9)	0.0003 (10)

Geometric parameters (Å, º)

P1—O1	1.4986 (17)	N3—C2	1.319 (3)
P1—O2	1.5157 (16)	N3—C4	1.375 (3)
P1—O3	1.5768 (17)	N3—H3N	0.77 (4)
P1—P1^i	2.1741 (11)	C2—H2	0.9500
O3—H3	0.86 (4)	C4—C5	1.349 (3)
N1—C2	1.324 (3)	C4—H4	0.9500
N1—C5	1.373 (3)	C5—H5	0.9500
N1—H1N	0.80 (4)
O1—P1—O2	117.29 (9)	C2—N3—H3N	126 (2)
O1—P1—O3	111.45 (10)	C4—N3—H3N	125 (2)
O2—P1—O3	106.66 (9)	N3—C2—N1	108.8 (2)
O1—P1—P1^i	108.62 (7)	N3—C2—H2	125.6
O2—P1—P1^i	107.62 (6)	N1—C2—H2	125.6
O3—P1—P1^i	104.37 (7)	C5—C4—N3	107.0 (2)
P1—O3—H3	112 (2)	C5—C4—H4	126.5
C2—N1—C5	108.7 (2)	N3—C4—H4	126.5
C2—N1—H1N	122 (2)	C4—C5—N1	106.8 (2)
C5—N1—H1N	129 (2)	C4—C5—H5	126.6
C2—N3—C4	108.7 (2)	N1—C5—H5	126.6
C4—N3—C2—N1	−0.8 (3)	O3—P1—P1^i—O1^i	−51.39 (9)
C5—N1—C2—N3	1.0 (3)	O1—P1—P1^i—O2^i	−164.46 (9)
C2—N3—C4—C5	0.4 (3)	O2—P1—P1^i—O2^i	−36.54 (13)
N3—C4—C5—N1	0.2 (3)	O3—P1—P1^i—O2^i	76.54 (9)
C2—N1—C5—C4	−0.7 (3)	O1—P1—P1^i—O3^i	−51.39 (10)
O1—P1—P1^i—O1^i	67.61 (15)	O2—P1—P1^i—O3^i	76.54 (9)
O2—P1—P1^i—O1^i	−164.46 (9)	O3—P1—P1^i—O3^i	−170.38 (13)

Symmetry code: (i) y, x, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2^ii	0.86 (4)	1.73 (4)	2.576 (2)	169 (4)
N1—H1N···O2	0.80 (4)	1.93 (4)	2.731 (3)	178 (3)
N3—H3N···O1^iii	0.77 (4)	1.84 (4)	2.616 (3)	175 (4)
C2—H2···O2^i	0.95	2.53	3.302 (3)	139

Symmetry codes: (i) y, x, −z+1; (ii) x−1/2, −y+1/2, −z+5/4; (iii) x, y+1, z.