Contributions to the application of the transferability principle and the multipolar modeling of H atoms: electron-density study of L-histidinium dihydrogen orthophosphate orthophosphoric acid. I

The electron density of L-histidinium dihydrogen orthophosphate orthophos­phoric acid has been determined from X-ray and neutron diffraction data at low temperature (120 K). Topological analysis of the electron density has been used to analyse the effect of the multipolar refinement strategy on the electron-density model in the hydrogen-bonding regions. The electron density at low temperature has also been used to acquire high-quality experimental thermal parameters at room temperature using the transferability principle. Molecular vibrations, TLS and normal mode analysis are discussed and studied at both temperatures.

Computing details

Data collection: CAD-4 (Enraf Nonius, 1989) for LHP-XR-A, LHP-XL-Nb. Cell refinement: CAD-4 (Enraf Nonius, 1989) for LHP-XR-A, LHP-XL-Nb. Data reduction: DREADD (Blessing 1987) for LHP-XR-A, LHP-XL-Nb. For all compounds, program(s) used to refine structure: MOLLY (Hansen & Coppens, 1978).

Figures

(LHP-XR-A)

Crystal data

C6H10N3O2·H3O4P·H2O4P	F(000) = 364
Mr = 351.09	Dx = 1.74 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 9.155 (2) Å	θ = 12–19°
b = 8.913 (1) Å	µ = 0.37 mm^−1
c = 8.806 (2) Å	T = 294 K
β = 111.35 (2)°	Prism, colourless
V = 669.2 (2) Å^3	0.50 × 0.30 × 0.20 mm
Z = 2

Data collection

κ-geometry diffractometer	Rint = 0.054
profile data from ω/2θ scans	θmax = 71.4°
Absorption correction: gaussian (DeTitta, 1985)	h = −22→22
Tmin = 0.870, Tmax = 0.938	k = −19→19
24122 measured reflections	l = −17→20
5860 independent reflections	3 standard reflections every 718 reflections
4033 reflections with I > 3u(I)	intensity decay: 8%

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.023	Weighting scheme based on measured s.u.'s
wR(F^2) = 0.063	(Δ/σ)max < 0.001
S = 0.75	Δρmax = 0.20 e Å^−3
5860 reflections	Δρmin = −0.30 e Å^−3
189 parameters

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

	x	y	z	Uiso*/Ueq
P1	0.59350 (3)	0.11024 (1)	0.99100 (2)	0.0237
O11	0.50344 (8)	0.12308 (9)	0.80991 (7)	0.0273
O12	0.54329 (13)	0.22475 (11)	1.08986 (9)	0.0661
O13	0.57666 (11)	−0.04611 (10)	1.05992 (9)	0.0351
O14	0.77016 (9)	0.13356 (12)	1.02067 (9)	0.0365
P2	0.55061 (3)	0.30458 (4)	0.47160 (2)	0.0253
O21	0.37665 (8)	0.31048 (12)	0.41511 (8)	0.0287
O22	0.63348 (9)	0.28631 (12)	0.65744 (8)	0.0331
O23	0.60889 (13)	0.17021 (13)	0.39509 (10)	0.0615
O24	0.62685 (10)	0.44919 (13)	0.43724 (11)	0.0436
O1	1.00866 (12)	0.84795 (10)	0.66641 (10)	0.0339
O2	1.06399 (9)	0.60422 (9)	0.67480 (8)	0.0325
C1	0.99972 (9)	0.72250 (10)	0.60375 (8)	0.0209
N1	0.78771 (8)	0.83688 (10)	0.37653 (8)	0.0270
C2	0.89932 (9)	0.70869 (9)	0.42198 (8)	0.0190
C3	1.00456 (10)	0.71105 (11)	0.32016 (9)	0.0248
C4	0.91860 (10)	0.67892 (10)	0.14386 (9)	0.0267
N5	0.87065 (11)	0.53619 (10)	0.08562 (9)	0.0317
C6	0.79681 (13)	0.54170 (14)	−0.07538 (11)	0.0332
N7	0.79569 (10)	0.68271 (12)	−0.12342 (9)	0.0383
C8	0.87061 (11)	0.77070 (11)	0.01163 (11)	0.0388
H1A	0.71044 (1)	0.83346 (1)	0.25715 (1)	0.0327*
H1B	0.72602 (1)	0.84402 (1)	0.45375 (1)	0.0327*
H1C	0.84863 (1)	0.93604 (1)	0.38613 (1)	0.0327*
H2	0.83123 (1)	0.60421 (1)	0.40297 (1)	0.0212*
H3A	1.10003 (1)	0.62923 (1)	0.36945 (1)	0.0266*
H3B	1.06419 (1)	0.81988 (1)	0.33232 (1)	0.0266*
H5	0.89483 (1)	0.44395 (1)	0.15694 (1)	0.0309*
H6	0.74425 (1)	0.44999 (1)	−0.15652 (1)	0.0358*
H7	0.73946 (1)	0.72655 (1)	−0.23523 (1)	0.0343*
H8	0.88218 (1)	0.89029 (1)	0.00260 (1)	0.0322*
H13	0.52607 (1)	−0.13041 (1)	0.99125 (1)	0.0470*
H14	0.83863 (1)	0.12845 (1)	1.13440 (1)	0.0507*
H22	0.58335 (1)	0.22353 (1)	0.71423 (1)	0.0485*
H23	0.58840 (1)	0.18595 (1)	0.28016 (1)	0.0636*
H24	0.57276 (1)	0.50515 (1)	0.33814 (1)	0.0560*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.02703 (8)	0.01826 (8)	0.01133 (6)	0.00102 (7)	0.00522 (6)	0.00144 (6)
O11	0.0325 (3)	0.0276 (3)	0.01274 (17)	−0.0028 (3)	0.00286 (18)	0.0019 (2)
O12	0.0723 (6)	0.0335 (4)	0.0214 (3)	0.0253 (4)	0.0211 (4)	0.0048 (3)
O13	0.0501 (4)	0.0221 (3)	0.0218 (3)	−0.0087 (3)	0.0025 (3)	0.0063 (2)
O14	0.0299 (3)	0.0498 (6)	0.0217 (3)	−0.0088 (3)	0.0057 (2)	0.0030 (3)
P2	0.02318 (8)	0.02886 (10)	0.01352 (6)	−0.00307 (8)	0.00663 (6)	0.00035 (7)
O21	0.0232 (2)	0.0437 (4)	0.0206 (2)	−0.0062 (3)	0.00693 (19)	−0.0088 (3)
O22	0.0353 (3)	0.0477 (5)	0.0141 (2)	−0.0122 (3)	0.0053 (2)	0.0016 (3)
O23	0.0564 (5)	0.0453 (5)	0.0254 (3)	0.0186 (4)	0.0187 (4)	0.0031 (3)
O24	0.0331 (4)	0.0434 (5)	0.0356 (4)	−0.0119 (3)	0.0036 (3)	0.0157 (4)
O1	0.0553 (5)	0.0239 (3)	0.0208 (3)	0.0064 (3)	−0.0069 (3)	−0.0082 (2)
O2	0.0380 (3)	0.0249 (3)	0.0175 (2)	0.0075 (3)	0.0008 (2)	−0.0003 (2)
C1	0.0229 (3)	0.0206 (3)	0.0133 (2)	−0.0000 (2)	0.0022 (2)	−0.0019 (2)
N1	0.0210 (2)	0.0291 (3)	0.0151 (2)	0.0026 (2)	0.00404 (18)	0.0026 (2)
C2	0.0192 (3)	0.0210 (3)	0.0128 (2)	−0.0031 (2)	0.00299 (19)	−0.0008 (2)
C3	0.0208 (3)	0.0291 (4)	0.0166 (2)	−0.0015 (3)	0.0058 (2)	−0.0027 (3)
C4	0.0244 (3)	0.0232 (3)	0.0143 (2)	0.0032 (3)	0.0066 (2)	0.0012 (2)
N5	0.0384 (4)	0.0235 (3)	0.0152 (2)	0.0030 (3)	0.0044 (2)	0.0013 (2)
C6	0.0393 (5)	0.0346 (5)	0.0157 (3)	0.0019 (4)	0.0028 (3)	−0.0033 (3)
N7	0.0304 (3)	0.0407 (5)	0.0146 (2)	0.0084 (3)	0.0054 (2)	0.0067 (3)
C8	0.0317 (4)	0.0266 (4)	0.0222 (3)	0.0061 (3)	0.0115 (3)	0.0073 (3)

Geometric parameters (Å, º)

P1—O11	1.5095 (6)	N7—C8	1.3805 (13)
P1—O12	1.5173 (8)	C8—C4	1.3585 (11)
P1—O13	1.5499 (8)	N1—H1A	1.032 (1)
P1—O14	1.5555 (8)	N1—H1B	1.032 (1)
P2—O21	1.4865 (7)	N1—H1C	1.032 (1)
P2—O22	1.5415 (7)	C2—H2	1.099 (1)
P2—O23	1.5604 (9)	C3—H3A	1.099 (1)
P2—O24	1.5472 (9)	C3—H3B	1.099 (1)
C1—O1	1.2363 (11)	N5—H5	1.009 (1)
C1—O2	1.2574 (11)	C6—H6	1.077 (1)
C2—C1	1.5333 (10)	N7—H7	1.009 (1)
C2—N1	1.4872 (11)	C8—H8	1.077 (1)
C2—C3	1.5368 (11)	O13—H13	0.967 (1)
C3—C4	1.4906 (10)	O14—H14	0.967 (1)
C4—N5	1.3821 (12)	O22—H22	0.967 (1)
N5—C6	1.3310 (11)	O23—H23	0.967 (1)
C6—N7	1.3249 (16)	O24—H24	0.967 (1)
O11—P1—O12	113.08 (5)	C1—C2—N1	108.14 (6)
O11—P1—O13	112.82 (4)	C1—C2—C3	110.07 (6)
O11—P1—O14	107.58 (4)	C1—C2—H2	108.560 (1)
O12—P1—O13	106.62 (5)	N1—C2—C3	110.35 (7)
O12—P1—O14	109.11 (6)	N1—C2—H2	108.298 (1)
O13—P1—O14	107.45 (5)	C3—C2—H2	111.347 (1)
P1—O13—H13	123.050 (1)	C2—C3—C4	113.55 (6)
P1—O14—H14	114.125 (1)	C2—C3—H3A	109.747 (1)
O21—P2—O22	114.35 (4)	C2—C3—H3B	110.481 (1)
O21—P2—O23	112.07 (6)	C4—C3—H3A	109.043 (1)
O21—P2—O24	114.19 (6)	C4—C3—H3B	109.039 (1)
O22—P2—O23	105.30 (5)	H3A—C3—H3B	104.583 (1)
O22—P2—O24	102.29 (5)	C3—C4—N5	122.63 (7)
O23—P2—O24	107.78 (6)	C3—C4—C8	131.33 (9)
P2—O22—H22	117.770 (1)	N5—C4—C8	106.04 (7)
P2—O23—H23	111.893 (1)	C4—N5—C6	109.32 (8)
P2—O24—H24	119.041 (1)	C4—N5—H5	123.431 (1)
O1—C1—O2	126.39 (7)	C6—N5—H5	127.179 (1)
O1—C1—C2	117.11 (7)	N5—C6—N7	108.48 (9)
O2—C1—C2	116.50 (7)	N5—C6—H6	127.567 (1)
C2—N1—H1A	113.607 (1)	C6—N7—C8	108.67 (7)
C2—N1—H1B	110.928 (1)	C6—N7—H7	128.379 (1)
C2—N1—H1C	109.756 (1)	C8—N7—H7	122.516 (1)
H1A—N1—H1B	109.662 (1)	C4—C8—N7	107.49 (9)
H1A—N1—H1C	104.972 (1)	C4—C8—H8	130.497 (1)
H1B—N1—H1C	107.593 (1)	N7—C8—H8	122.009 (1)

(LHP-XL-Nb)

Crystal data

C6H10N3O2·H3O4P·H2O4P	F(000) = 364
Mr = 351.09	Dx = 1.76 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 9.084 (3) Å	θ = 12–29°
b = 8.913 (1) Å	µ = 0.37 mm^−1
c = 8.786 (2) Å	T = 120 K
β = 111.03 (2)°	Prism, colourless
V = 664.0 (3) Å^3	0.45 × 0.35 × 0.32 mm
Z = 2

Data collection

κ-geometry diffractometer	Rint = 0.025
profile data from ω/2θ scans	θmax = 73.6°
Absorption correction: gaussian (DeTitta, 1985)	h = −22→22
Tmin = 0.870, Tmax = 0.938	k = −23→23
27559 measured reflections	l = −16→22
7634 independent reflections	3 standard reflections every 156 reflections
6558 reflections with I > 2u(I)	intensity decay: 14%

Refinement

Refinement on F	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.018	Weighting scheme based on measured s.u.'s
wR(F^2) = 0.032	(Δ/σ)max = 0.113
S = 0.86	Δρmax = 0.29 e Å^−3
6558 reflections	Δρmin = −0.21 e Å^−3
512 parameters

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

	x	y	z	Uiso*/Ueq
P1	0.59358 (1)	0.11024 (1)	0.99219 (1)	0.0114
O11	0.50173 (11)	0.12322 (12)	0.81092 (8)	0.0137
O12	0.54507 (18)	0.22536 (15)	1.09314 (11)	0.0310
O13	0.57481 (15)	−0.04667 (12)	1.06090 (11)	0.0173
O14	0.77206 (12)	0.13179 (15)	1.01964 (10)	0.0178
P2	0.55073 (1)	0.30673 (2)	0.47281 (1)	0.0120
O21	0.37494 (10)	0.31407 (15)	0.41429 (9)	0.0139
O22	0.63148 (12)	0.28966 (14)	0.65963 (9)	0.0158
O23	0.61058 (17)	0.17180 (17)	0.39774 (12)	0.0288
O24	0.62877 (14)	0.45233 (17)	0.43880 (14)	0.0212
O1	1.01111 (7)	0.85069 (9)	0.66654 (7)	0.0171
O2	1.06381 (5)	0.60491 (9)	0.67636 (6)	0.0160
C1	1.00043 (5)	0.72432 (7)	0.60425 (5)	0.0109
N1	0.78907 (6)	0.83946 (8)	0.37653 (6)	0.0138
C2	0.90073 (6)	0.71038 (7)	0.42229 (5)	0.0101
C3	1.00732 (6)	0.71203 (7)	0.32030 (6)	0.0127
C4	0.92041 (5)	0.68088 (7)	0.14370 (6)	0.0133
N5	0.87126 (6)	0.53826 (8)	0.08468 (6)	0.0154
C6	0.79672 (7)	0.54470 (9)	−0.07631 (7)	0.0165
N7	0.79620 (6)	0.68650 (9)	−0.12353 (7)	0.0186
C8	0.87196 (6)	0.77384 (8)	0.01148 (7)	0.0185
H1A	0.71168 (1)	0.83361 (1)	0.25868 (1)	0.0269
H1B	0.72498 (1)	0.84387 (1)	0.45448 (1)	0.0258
H1C	0.85112 (1)	0.93856 (1)	0.38708 (1)	0.0281
H2	0.83196 (1)	0.60677 (1)	0.40279 (1)	0.0254
H3A	1.10086 (1)	0.62886 (1)	0.37066 (1)	0.0252
H3B	1.06511 (1)	0.82138 (1)	0.33285 (1)	0.0320
H5	0.89557 (1)	0.44170 (1)	0.15823 (1)	0.0412
H6	0.74445 (1)	0.45156 (1)	−0.15630 (1)	0.0464
H7	0.73684 (1)	0.72886 (1)	−0.24094 (1)	0.0314
H8	0.88249 (1)	0.89289 (1)	0.00286 (1)	0.0473
H13	0.52050 (1)	−0.13804 (1)	0.98513 (1)	0.0309
H14	0.84269 (1)	0.12835 (1)	1.14189 (1)	0.0257
H22	0.57997 (1)	0.21872 (1)	0.71778 (1)	0.0288
H23	0.58763 (1)	0.18674 (1)	0.27693 (1)	0.0406
H24	0.57110 (1)	0.50685 (1)	0.33507 (1)	0.0306

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.01295 (4)	0.00886 (5)	0.00559 (3)	0.00054 (4)	0.00245 (3)	0.00065 (3)
O11	0.01579 (19)	0.0136 (2)	0.00652 (12)	−0.00100 (18)	0.00153 (13)	0.00092 (14)
O12	0.0339 (3)	0.0166 (3)	0.01024 (17)	0.0120 (3)	0.0093 (2)	0.00187 (18)
O13	0.0251 (3)	0.0110 (2)	0.01079 (17)	−0.0047 (2)	0.00121 (19)	0.00288 (16)
O14	0.0140 (2)	0.0253 (3)	0.01066 (16)	−0.0042 (2)	0.00260 (16)	0.00128 (19)
P2	0.01070 (4)	0.01407 (5)	0.00648 (3)	−0.00146 (4)	0.00291 (3)	0.00021 (4)
O21	0.01095 (16)	0.0211 (3)	0.01047 (14)	−0.0031 (2)	0.00322 (13)	−0.00436 (18)
O22	0.0172 (2)	0.0220 (3)	0.00667 (13)	−0.0058 (2)	0.00238 (14)	0.00126 (17)
O23	0.0263 (3)	0.0220 (3)	0.01172 (19)	0.0086 (3)	0.0084 (2)	0.0014 (2)
O24	0.0166 (2)	0.0214 (3)	0.0167 (2)	−0.0061 (2)	0.0016 (2)	0.0079 (2)
O1	0.0280 (3)	0.0118 (2)	0.01069 (16)	0.00261 (17)	−0.00309 (16)	−0.00407 (16)
O2	0.01817 (17)	0.0121 (2)	0.00910 (13)	0.00345 (15)	0.00052 (12)	0.00002 (16)
C1	0.01194 (15)	0.01044 (19)	0.00690 (12)	0.00016 (13)	0.00116 (11)	−0.00098 (13)
N1	0.01053 (16)	0.0144 (2)	0.00832 (13)	0.00106 (15)	0.00231 (12)	0.00129 (14)
C2	0.01022 (15)	0.01085 (18)	0.00666 (12)	−0.00149 (14)	0.00173 (11)	−0.00038 (12)
C3	0.01051 (16)	0.0149 (2)	0.00873 (14)	−0.00086 (16)	0.00288 (12)	−0.00125 (14)
C4	0.01201 (15)	0.01181 (18)	0.00717 (13)	0.00176 (13)	0.00284 (11)	0.00076 (13)
N5	0.01888 (19)	0.0113 (2)	0.00776 (13)	0.00120 (14)	0.00179 (12)	0.00083 (14)
C6	0.0193 (2)	0.0166 (3)	0.00825 (15)	0.00085 (17)	0.00143 (13)	−0.00122 (16)
N7	0.01490 (18)	0.0191 (3)	0.00769 (14)	0.00379 (15)	0.00260 (12)	0.00334 (16)
C8	0.01569 (18)	0.0126 (2)	0.01096 (15)	0.00258 (14)	0.00509 (13)	0.00322 (15)
H1A	0.02693 (1)	0.04255 (1)	0.01932 (1)	0.01076 (1)	0.00052 (1)	−0.00140 (1)
H1B	0.02575 (1)	0.03629 (1)	0.02381 (1)	0.00356 (1)	0.01220 (1)	0.00324 (1)
H1C	0.02815 (1)	0.02185 (1)	0.03382 (1)	−0.00268 (1)	0.01050 (1)	0.00428 (1)
H2	0.02543 (1)	0.02301 (1)	0.02422 (1)	−0.00920 (1)	0.00654 (1)	−0.00045 (1)
H3A	0.02520 (1)	0.03905 (1)	0.02360 (1)	0.01079 (1)	0.00532 (1)	0.00252 (1)
H3B	0.03200 (1)	0.03050 (1)	0.02790 (1)	−0.01337 (1)	0.01184 (1)	−0.00420 (1)
H5	0.04119 (1)	0.01974 (1)	0.02243 (1)	0.00114 (1)	0.00697 (1)	0.00428 (1)
H6	0.04639 (1)	0.03097 (1)	0.02451 (1)	−0.00598 (1)	0.00418 (1)	−0.01232 (1)
H7	0.03136 (1)	0.03954 (1)	0.01705 (1)	0.00373 (1)	0.00585 (1)	0.00819 (1)
H8	0.04728 (1)	0.01840 (1)	0.03396 (1)	−0.00096 (1)	0.01502 (1)	0.00403 (1)
H13	0.03085 (1)	0.02916 (1)	0.02263 (1)	−0.00207 (1)	0.00833 (1)	0.00124 (1)
H14	0.02568 (1)	0.03407 (1)	0.02337 (1)	−0.00404 (1)	0.00631 (1)	−0.00080 (1)
H22	0.02884 (1)	0.02813 (1)	0.01975 (1)	−0.00342 (1)	0.00847 (1)	0.00186 (1)
H23	0.04062 (1)	0.03552 (1)	0.02198 (1)	0.00779 (1)	0.01505 (1)	−0.00142 (1)
H24	0.03058 (1)	0.03145 (1)	0.02269 (1)	−0.00314 (1)	0.00500 (1)	0.00546 (1)

Geometric parameters (Å, º)

P1—O11	1.5140 (7)	N7—C8	1.3786 (9)
P1—O12	1.5212 (10)	C8—C4	1.3648 (8)
P1—O13	1.5567 (10)	N1—H1A	1.0230 (1)
P1—O14	1.5630 (10)	N1—H1B	1.0467 (1)
P2—O21	1.4931 (9)	N1—H1C	1.0340 (1)
P2—O22	1.5464 (7)	C2—H2	1.0934 (1)
P2—O23	1.5602 (12)	C3—H3A	1.0943 (1)
P2—O24	1.5583 (12)	C3—H3B	1.0937 (1)
C1—O1	1.2407 (9)	N5—H5	1.0510 (1)
C1—O2	1.2664 (9)	C6—H6	1.0812 (1)
C2—C1	1.5338 (6)	N7—H7	1.0480 (1)
C2—N1	1.4904 (8)	C8—H8	1.0706 (1)
C2—C3	1.5374 (7)	O13—H13	1.0555 (1)
C3—C4	1.4929 (7)	O14—H14	1.0351 (1)
C4—N5	1.3849 (9)	O22—H22	1.0254 (1)
N5—C6	1.3323 (7)	O23—H23	1.0144 (1)
C6—N7	1.3298 (10)	O24—H24	0.9992 (1)
O11—P1—O12	113.34 (6)	C1—C2—N1	107.99 (4)
O11—P1—O13	112.39 (5)	C1—C2—C3	110.30 (4)
O11—P1—O14	107.61 (5)	C1—C2—H2	108.796 (1)
O12—P1—O13	106.55 (7)	N1—C2—C3	110.21 (4)
O12—P1—O14	109.18 (8)	N1—C2—H2	108.325 (1)
O13—P1—O14	107.61 (7)	C3—C2—H2	111.144 (1)
P1—O13—H13	122.690 (1)	C2—C3—C4	113.28 (4)
P1—O14—H14	112.261 (1)	C2—C3—H3A	108.535 (1)
O21—P2—O22	114.28 (5)	C2—C3—H3B	109.249 (1)
O21—P2—O23	112.34 (7)	C4—C3—H3A	109.792 (1)
O21—P2—O24	113.67 (7)	C4—C3—H3B	109.044 (1)
O22—P2—O23	105.57 (6)	H3A—C3—H3B	106.734 (1)
O22—P2—O24	102.14 (6)	C3—C4—N5	122.62 (5)
O23—P2—O24	108.02 (8)	C3—C4—C8	131.34 (6)
P2—O22—H22	117.523 (1)	N5—C4—C8	106.04 (5)
P2—O23—H23	111.667 (1)	C4—N5—C6	109.31 (6)
P2—O24—H24	117.012 (1)	C4—N5—H5	123.575 (1)
O1—C1—O2	126.35 (6)	C6—N5—H5	127.059 (1)
O1—C1—C2	117.18 (5)	N5—C6—N7	108.41 (6)
O2—C1—C2	116.47 (5)	N5—C6—H6	126.467 (1)
C2—N1—H1A	112.808 (1)	C6—N7—C8	108.87 (5)
C2—N1—H1B	109.691 (1)	C6—N7—H7	126.334 (1)
C2—N1—H1C	109.811 (1)	C8—N7—H7	124.418 (1)
H1A—N1—H1B	108.820 (1)	C4—C8—N7	107.37 (6)
H1A—N1—H1C	106.788 (1)	C4—C8—H8	130.707 (1)
H1B—N1—H1C	108.815 (1)	N7—C8—H8	121.902 (1)

(LHP-NR-A)

Crystal data

C6H10N3O2·H3O4P·H2O4P	Z = 2
Mr = 351.09	Dx = 1.74 Mg m^−3
Monoclinic, P21	Neutrons radiation, λ = 0.8308 Å
Hall symbol: P 2yb	Cell parameters from 16 reflections
a = 9.15 (1) Å	θ = 11.5–16.5°
b = 8.91 (1) Å	T = 293 K
c = 8.81 (1) Å	Prism, colourless
β = 111.4 (5)°	6 × 3 × 2 mm
V = 669 (3) Å^3

Data collection

Four-circle diffractometer	θmax = 45°
profile data from ω/2θ scans	h = −13→15
4982 measured reflections	k = −15→0
3535 independent reflections	l = −14→6
2614 reflections with I > 3u(I)	2 standard reflections every 88 reflections
Rint = 0.039	intensity decay: 0.0%

Refinement

Refinement on F^2	Weighting scheme based on measured s.u.'s
R[F^2 > 2σ(F^2)] = 0.028	(Δ/σ)max = 0.048
wR(F^2) = 0.058	Δρmax = 0.46 e Å^−3
S = 1.06	Δρmin = −0.56 e Å^−3
3535 reflections	Extinction correction: B-C type 2 Lorentzian isotropic
325 parameters	Extinction coefficient: 0.255 (5)
All H-atom parameters refined

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

	x	y	z	Uiso*/Ueq
P1	0.59342 (17)	0.11024 (1)	0.99127 (15)	0.0215
O11	0.50336 (16)	0.1233 (2)	0.80988 (14)	0.0248
O12	0.5436 (2)	0.2248 (3)	1.08958 (17)	0.0596
O13	0.5755 (2)	−0.0450 (3)	1.05973 (17)	0.0327
O14	0.76974 (17)	0.1335 (3)	1.02066 (17)	0.0333
P2	0.55061 (16)	0.3046 (2)	0.47167 (14)	0.0220
O21	0.37661 (15)	0.3112 (3)	0.41466 (15)	0.0254
O22	0.63323 (17)	0.2868 (3)	0.65760 (15)	0.0292
O23	0.6091 (2)	0.1713 (3)	0.39548 (19)	0.0573
O24	0.62663 (19)	0.4496 (3)	0.4370 (2)	0.0382
O1	1.0094 (2)	0.8483 (2)	0.66632 (17)	0.0316
O2	1.06426 (18)	0.6045 (2)	0.67516 (16)	0.0291
C1	0.99974 (12)	0.7229 (2)	0.60390 (10)	0.0176
N1	0.78780 (9)	0.83749 (19)	0.37674 (8)	0.0240
C2	0.89971 (11)	0.7090 (2)	0.42207 (10)	0.0163
C3	1.00465 (12)	0.7115 (2)	0.32036 (12)	0.0214
C4	0.91856 (12)	0.6794 (2)	0.14381 (11)	0.0232
N5	0.87063 (11)	0.53671 (19)	0.08577 (9)	0.0283
C6	0.79671 (16)	0.5422 (2)	−0.07538 (13)	0.0302
N7	0.79609 (11)	0.6836 (2)	−0.12288 (9)	0.0352
C8	0.87045 (15)	0.7717 (2)	0.01144 (14)	0.0345
H1A	0.7110 (3)	0.8322 (5)	0.2598 (3)	0.0471
H1B	0.7241 (3)	0.8410 (4)	0.4539 (3)	0.0544
H1C	0.8486 (4)	0.9373 (4)	0.3880 (4)	0.0485
H2	0.8325 (3)	0.6047 (4)	0.4028 (3)	0.0323
H3A	1.0973 (3)	0.6287 (5)	0.3705 (3)	0.0532
H3B	1.0602 (4)	0.8214 (4)	0.3327 (4)	0.0448
H5	0.8964 (4)	0.4418 (4)	0.1595 (3)	0.0502
H6	0.7460 (5)	0.4496 (5)	−0.1546 (4)	0.0511
H7	0.7367 (4)	0.7244 (5)	−0.2401 (3)	0.0567
H8	0.8802 (5)	0.8899 (4)	0.0013 (4)	0.0691
H13	0.5213 (4)	−0.1383 (4)	0.9858 (3)	0.0501
H14	0.8396 (3)	0.1305 (4)	1.1418 (3)	0.0395
H22	0.5827 (3)	0.2176 (4)	0.7168 (3)	0.0391
H23	0.5858 (4)	0.1864 (5)	0.2759 (3)	0.0648
H24	0.5686 (4)	0.5051 (4)	0.3351 (3)	0.0460

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0251 (6)	0.0171 (5)	0.0097 (4)	0.0007 (5)	0.0045 (4)	0.0011 (4)
O11	0.0301 (6)	0.0267 (6)	0.0097 (4)	−0.0022 (5)	0.0019 (4)	0.0018 (4)
O12	0.0660 (11)	0.0330 (8)	0.0178 (5)	0.0237 (8)	0.0173 (6)	0.0034 (5)
O13	0.0484 (9)	0.0218 (6)	0.0179 (5)	−0.0086 (6)	0.0023 (5)	0.0059 (5)
O14	0.0260 (6)	0.0473 (10)	0.0197 (5)	−0.0078 (6)	0.0053 (5)	0.0019 (6)
P2	0.0200 (5)	0.0269 (7)	0.0110 (4)	−0.0028 (5)	0.0051 (4)	0.0004 (4)
O21	0.0188 (5)	0.0432 (8)	0.0181 (5)	−0.0060 (5)	0.0054 (4)	−0.0088 (5)
O22	0.0314 (7)	0.0457 (9)	0.0108 (4)	−0.0115 (6)	0.0032 (4)	0.0018 (5)
O23	0.0521 (10)	0.0418 (9)	0.0231 (6)	0.0181 (8)	0.0173 (6)	0.0038 (6)
O24	0.0284 (7)	0.0419 (9)	0.0314 (7)	−0.0122 (7)	0.0011 (5)	0.0144 (7)
O1	0.0534 (10)	0.0229 (7)	0.0181 (5)	0.0060 (7)	−0.0077 (6)	−0.0076 (5)
O2	0.0342 (7)	0.0230 (6)	0.0156 (5)	0.0068 (5)	−0.0004 (4)	0.0001 (4)
C1	0.0201 (4)	0.0189 (4)	0.0102 (3)	−0.0002 (4)	0.0011 (3)	−0.0021 (3)
N1	0.0182 (3)	0.0274 (4)	0.0127 (2)	0.0025 (3)	0.0033 (2)	0.0024 (3)
C2	0.0163 (4)	0.0204 (5)	0.0100 (3)	−0.0030 (4)	0.0022 (3)	−0.0010 (3)
C3	0.0169 (4)	0.0283 (5)	0.0138 (3)	−0.0022 (4)	0.0047 (3)	−0.0024 (4)
C4	0.0211 (4)	0.0224 (5)	0.0109 (3)	0.0034 (4)	0.0050 (3)	0.0008 (3)
N5	0.0351 (4)	0.0217 (4)	0.0130 (3)	0.0025 (3)	0.0031 (3)	0.0013 (3)
C6	0.0362 (6)	0.0322 (6)	0.0128 (4)	0.0016 (6)	0.0023 (4)	−0.0023 (4)
N7	0.0281 (4)	0.0374 (5)	0.0122 (3)	0.0083 (4)	0.0048 (2)	0.0067 (3)
C8	0.0281 (5)	0.0243 (5)	0.0194 (4)	0.0056 (4)	0.0100 (4)	0.0065 (4)
H1A	0.0367 (12)	0.066 (2)	0.0200 (9)	0.0124 (14)	−0.0019 (8)	−0.0012 (12)
H1B	0.0358 (12)	0.0506 (16)	0.0305 (10)	0.0099 (12)	0.0177 (9)	0.0047 (12)
H1C	0.0419 (14)	0.0290 (12)	0.0425 (13)	0.0009 (11)	0.0128 (11)	0.0033 (11)
H2	0.0372 (12)	0.0297 (11)	0.0286 (10)	−0.0138 (10)	0.0084 (9)	−0.0034 (9)
H3A	0.0332 (12)	0.062 (2)	0.0272 (11)	0.0183 (13)	0.0054 (9)	0.0022 (12)
H3B	0.0427 (14)	0.0454 (17)	0.0417 (14)	−0.0198 (13)	0.0192 (12)	−0.0087 (13)
H5	0.0612 (18)	0.0284 (12)	0.0284 (11)	0.0031 (12)	0.0083 (11)	0.0056 (10)
H6	0.076 (2)	0.0497 (19)	0.0305 (12)	−0.0092 (18)	0.0043 (14)	−0.0135 (14)
H7	0.0457 (14)	0.0612 (19)	0.0201 (8)	0.0090 (14)	0.0082 (9)	0.0128 (12)
H8	0.074 (2)	0.0299 (14)	0.0489 (17)	0.0007 (14)	0.0213 (17)	0.0101 (13)
H13	0.0413 (14)	0.0548 (18)	0.0271 (10)	−0.0023 (14)	0.0096 (10)	0.0074 (12)
H14	0.0354 (13)	0.0419 (16)	0.0323 (12)	−0.0062 (11)	0.0053 (10)	−0.0010 (11)
H22	0.0401 (12)	0.0407 (14)	0.0211 (8)	−0.0051 (11)	0.0076 (8)	0.0025 (10)
H23	0.0619 (18)	0.0535 (19)	0.0277 (11)	0.0163 (16)	0.0185 (11)	−0.0011 (12)
H24	0.0399 (13)	0.0396 (15)	0.0334 (11)	−0.0057 (11)	0.0104 (10)	0.0074 (10)

Geometric parameters (Å, º)

P1—O11	1.512 (3)	N7—C8	1.376 (3)
P1—O12	1.512 (4)	C8—C4	1.362 (3)
P1—O13	1.541 (4)	N1—H1A	1.015 (5)
P1—O14	1.552 (4)	N1—H1B	1.045 (5)
P2—O21	1.486 (4)	N1—H1C	1.035 (6)
P2—O22	1.542 (3)	C2—H2	1.094 (5)
P2—O23	1.553 (5)	C3—H3A	1.088 (6)
P2—O24	1.550 (4)	C3—H3B	1.090 (7)
C1—O1	1.234 (4)	N5—H5	1.039 (6)
C1—O2	1.260 (4)	C6—H6	1.071 (8)
C2—C1	1.533 (2)	N7—H7	1.041 (5)
C2—N1	1.490 (3)	C8—H8	1.064 (7)
C2—C3	1.534 (3)	O13—H13	1.061 (8)
C3—C4	1.492 (3)	O14—H14	1.025 (6)
C4—N5	1.381 (3)	O22—H22	1.020 (6)
N5—C6	1.332 (3)	O23—H23	1.005 (6)
C6—N7	1.327 (4)	O24—H24	0.992 (6)
O11—P1—O12	113.0 (4)	C1—C2—N1	107.9 (4)
O11—P1—O13	112.8 (4)	C1—C2—C3	110.3 (4)
O11—P1—O14	107.4 (4)	C1—C2—H2	108.6 (4)
O12—P1—O13	106.5 (4)	N1—C2—C3	110.4 (4)
O12—P1—O14	109.1 (4)	N1—C2—H2	108.6 (4)
O13—P1—O14	107.9 (4)	C3—C2—H2	111.0 (4)
P1—O13—H13	123.8 (4)	C2—C3—C4	113.7 (4)
P1—O14—H14	112.8 (4)	C2—C3—H3A	108.3 (4)
O21—P2—O22	114.4 (4)	C2—C3—H3B	108.9 (4)
O21—P2—O23	112.3 (4)	C4—C3—H3A	109.3 (4)
O21—P2—O24	113.8 (4)	C4—C3—H3B	109.0 (4)
O22—P2—O23	105.5 (4)	H3A—C3—H3B	107.6 (6)
O22—P2—O24	102.4 (4)	C3—C4—N5	122.5 (4)
O23—P2—O24	107.6 (4)	C3—C4—C8	131.3 (4)
P2—O22—H22	117.9 (4)	N5—C4—C8	106.2 (4)
P2—O23—H23	112.1 (6)	C4—N5—C6	109.3 (4)
P2—O24—H24	117.6 (6)	C4—N5—H5	123.3 (4)
O1—C1—O2	126.3 (4)	C6—N5—H5	127.4 (4)
O1—C1—C2	117.2 (4)	N5—C6—N7	108.2 (4)
O2—C1—C2	116.5 (4)	N5—C6—H6	126.7 (6)
C2—N1—H1A	113.0 (6)	C6—N7—C8	109.1 (4)
C2—N1—H1B	109.9 (4)	C6—N7—H7	125.8 (6)
C2—N1—H1C	110.0 (4)	C8—N7—H7	124.7 (6)
H1A—N1—H1B	108.5 (6)	C4—C8—N7	107.3 (4)
H1A—N1—H1C	106.6 (6)	C4—C8—H8	131.2 (6)
H1B—N1—H1C	108.7 (6)	N7—C8—H8	121.6 (4)

(LHP-NL-B)

Crystal data

C6H10N3O2·H3O4P·H2O4P	Z = 2
Mr = 351.09	Dx = 1.77 Mg m^−3
Monoclinic, P21	Neutrons radiation, λ = 0.8308 Å
Hall symbol: P 2yb	Cell parameters from 18 reflections
a = 9.037 (6) Å	θ = 16.5–25°
b = 8.906 (5) Å	T = 120 K
c = 8.759 (5) Å	Prism, colourless
β = 110.93 (9)°	6 × 3 × 2 mm
V = 658.4 (8) Å^3

Data collection

Four-circle diffractometer	Rint = 0.088
profile data from ω scans	θmax = 45°
Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983)	h = −15→15
Tmin = 0.702, Tmax = 1.264	k = −15→0
4658 measured reflections	l = −14→8
3553 independent reflections	2 standard reflections every 50 reflections
3279 reflections with I > 3u(I)	intensity decay: none

Refinement

Refinement on F^2	Weighting scheme based on measured s.u.'s
R[F^2 > 2σ(F^2)] = 0.035	(Δ/σ)max = 0.020
wR(F^2) = 0.076	Δρmax = 1.26 e Å^−3
S = 1.81	Δρmin = −1.18 e Å^−3
3553 reflections	Extinction correction: B-C type 2 Lorentzian isotropic
325 parameters	Extinction coefficient: 0.25 (1)
All H-atom parameters refined

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

	x	y	z	Uiso*/Ueq
P1	0.59328 (18)	0.11024 (1)	0.99255 (16)	0.0132
O11	0.50190 (17)	0.1227 (3)	0.81118 (15)	0.0156
O12	0.5453 (2)	0.2250 (3)	1.09340 (16)	0.0283
O13	0.5739 (2)	−0.0462 (3)	1.06062 (16)	0.0180
O14	0.77231 (18)	0.1316 (3)	1.01973 (17)	0.0189
P2	0.55104 (17)	0.3067 (3)	0.47296 (15)	0.0133
O21	0.37480 (17)	0.3140 (3)	0.41378 (15)	0.0160
O22	0.63077 (18)	0.2901 (3)	0.66007 (15)	0.0164
O23	0.6107 (2)	0.1718 (3)	0.39815 (17)	0.0288
O24	0.62842 (19)	0.4517 (3)	0.43875 (18)	0.0215
O1	1.0116 (2)	0.8504 (3)	0.66645 (16)	0.0185
O2	1.06308 (18)	0.6046 (3)	0.67621 (16)	0.0170
C1	1.00079 (14)	0.7239 (2)	0.60445 (12)	0.0124
N1	0.78950 (10)	0.8397 (2)	0.37674 (9)	0.0150
C2	0.90096 (13)	0.7104 (2)	0.42241 (12)	0.0116
C3	1.00814 (14)	0.7118 (3)	0.32036 (13)	0.0141
C4	0.92075 (14)	0.6810 (2)	0.14383 (12)	0.0140
N5	0.87126 (11)	0.5383 (2)	0.08468 (9)	0.0162
C6	0.79646 (16)	0.5449 (3)	−0.07637 (13)	0.0170
N7	0.79643 (11)	0.6867 (2)	−0.12319 (9)	0.0195
C8	0.87220 (15)	0.7741 (2)	0.01173 (13)	0.0199
H1A	0.7117 (4)	0.8336 (5)	0.2587 (3)	0.0336
H1B	0.7250 (4)	0.8438 (5)	0.4544 (3)	0.0362
H1C	0.8511 (4)	0.9385 (4)	0.3871 (4)	0.0340
H2	0.8320 (4)	0.6067 (4)	0.4028 (3)	0.0254
H3A	1.1008 (4)	0.6282 (5)	0.3707 (4)	0.0366
H3B	1.0651 (4)	0.8214 (5)	0.3329 (4)	0.0303
H5	0.8956 (5)	0.4417 (4)	0.1583 (3)	0.0338
H6	0.7445 (5)	0.4516 (5)	−0.1563 (4)	0.0314
H7	0.7369 (4)	0.7289 (5)	−0.2409 (3)	0.0362
H8	0.8824 (5)	0.8929 (4)	0.0029 (4)	0.0414
H13	0.5205 (4)	−0.1381 (5)	0.9851 (3)	0.0318
H14	0.8427 (4)	0.1283 (5)	1.1419 (4)	0.0299
H22	0.5800 (4)	0.2188 (4)	0.7178 (3)	0.0297
H23	0.5876 (4)	0.1867 (5)	0.2769 (4)	0.0412
H24	0.5711 (4)	0.5068 (5)	0.3351 (4)	0.0322

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0122 (5)	0.0087 (6)	0.0099 (4)	0.0001 (5)	0.0038 (4)	0.0008 (4)
O11	0.0149 (5)	0.0138 (6)	0.0103 (4)	−0.0011 (5)	0.0030 (4)	0.0015 (4)
O12	0.0276 (7)	0.0156 (6)	0.0141 (4)	0.0086 (6)	0.0092 (5)	0.0009 (5)
O13	0.0212 (6)	0.0112 (6)	0.0136 (4)	−0.0030 (5)	0.0027 (4)	0.0028 (4)
O14	0.0129 (5)	0.0227 (8)	0.0146 (4)	−0.0037 (6)	0.0047 (4)	0.0006 (5)
P2	0.0097 (5)	0.0138 (7)	0.0098 (4)	−0.0012 (5)	0.0039 (4)	0.0004 (4)
O21	0.0097 (5)	0.0213 (7)	0.0147 (4)	−0.0032 (5)	0.0053 (4)	−0.0039 (5)
O22	0.0144 (5)	0.0199 (7)	0.0111 (4)	−0.0049 (5)	0.0039 (4)	0.0003 (4)
O23	0.0231 (7)	0.0213 (8)	0.0155 (5)	0.0072 (6)	0.0090 (5)	0.0022 (5)
O24	0.0140 (6)	0.0200 (7)	0.0195 (5)	−0.0038 (6)	0.0031 (5)	0.0057 (5)
O1	0.0245 (7)	0.0118 (6)	0.0138 (5)	0.0029 (6)	−0.0005 (5)	−0.0029 (4)
O2	0.0150 (5)	0.0121 (6)	0.0135 (4)	0.0030 (5)	0.0024 (4)	0.0001 (4)
C1	0.0104 (4)	0.0106 (5)	0.0109 (3)	0.0002 (4)	0.0025 (3)	−0.0011 (3)
N1	0.0098 (3)	0.0139 (4)	0.0119 (2)	0.0003 (3)	0.0038 (2)	0.0013 (2)
C2	0.0087 (4)	0.0122 (5)	0.0102 (3)	−0.0015 (4)	0.0027 (3)	−0.0008 (3)
C3	0.0094 (4)	0.0150 (5)	0.0117 (3)	−0.0005 (4)	0.0041 (3)	−0.0012 (4)
C4	0.0105 (4)	0.0117 (5)	0.0113 (3)	0.0002 (4)	0.0041 (3)	0.0001 (3)
N5	0.0165 (3)	0.0111 (4)	0.0117 (3)	0.0002 (3)	0.0035 (2)	0.0006 (3)
C6	0.0169 (5)	0.0147 (5)	0.0122 (4)	0.0000 (5)	0.0031 (4)	−0.0008 (4)
N7	0.0134 (3)	0.0184 (4)	0.0112 (3)	0.0035 (3)	0.0040 (2)	0.0033 (3)
C8	0.0136 (5)	0.0129 (5)	0.0147 (4)	0.0027 (4)	0.0068 (3)	0.0029 (4)
H1A	0.0234 (12)	0.0380 (18)	0.0216 (9)	0.0089 (13)	0.0022 (9)	−0.0012 (11)
H1B	0.0225 (11)	0.0326 (16)	0.0255 (9)	0.0030 (12)	0.0123 (9)	0.0028 (11)
H1C	0.0243 (12)	0.0207 (13)	0.0339 (11)	−0.0025 (11)	0.0108 (10)	0.0039 (10)
H2	0.0221 (11)	0.0213 (13)	0.0258 (10)	−0.0082 (10)	0.0074 (9)	−0.0005 (9)
H3A	0.0221 (11)	0.0354 (17)	0.0252 (10)	0.0092 (12)	0.0063 (9)	0.0021 (11)
H3B	0.0276 (13)	0.0283 (15)	0.0290 (10)	−0.0120 (12)	0.0121 (10)	−0.0036 (11)
H5	0.0356 (15)	0.0183 (12)	0.0242 (10)	0.0009 (12)	0.0078 (10)	0.0037 (9)
H6	0.0401 (17)	0.0287 (15)	0.0258 (11)	−0.0053 (15)	0.0053 (11)	−0.0106 (11)
H7	0.0271 (13)	0.0359 (17)	0.0196 (8)	0.0031 (13)	0.0068 (9)	0.0069 (10)
H8	0.0413 (18)	0.0179 (13)	0.0340 (13)	−0.0013 (13)	0.0146 (13)	0.0033 (10)
H13	0.0268 (12)	0.0269 (14)	0.0243 (9)	−0.0022 (12)	0.0091 (9)	0.0010 (10)
H14	0.0224 (11)	0.0313 (16)	0.0249 (10)	−0.0036 (12)	0.0071 (9)	−0.0008 (11)
H22	0.0250 (12)	0.0260 (13)	0.0220 (9)	−0.0032 (11)	0.0092 (9)	0.0016 (10)
H23	0.0354 (15)	0.0319 (16)	0.0239 (10)	0.0066 (14)	0.0148 (10)	−0.0012 (11)
H24	0.0264 (13)	0.0288 (15)	0.0245 (10)	−0.0029 (11)	0.0061 (10)	0.0047 (10)

Geometric parameters (Å, º)

P1—O11	1.5088 (18)	N7—C8	1.3751 (15)
P1—O12	1.512 (2)	C8—C4	1.3618 (16)
P1—O13	1.550 (2)	N1—H1A	1.022 (3)
P1—O14	1.560 (2)	N1—H1B	1.044 (3)
P2—O21	1.489 (2)	N1—H1C	1.028 (4)
P2—O22	1.5425 (17)	C2—H2	1.093 (3)
P2—O23	1.554 (2)	C3—H3A	1.085 (4)
P2—O24	1.548 (2)	C3—H3B	1.090 (4)
C1—O1	1.239 (2)	N5—H5	1.050 (3)
C1—O2	1.2599 (19)	C6—H6	1.079 (4)
C2—C1	1.5292 (13)	N7—H7	1.047 (3)
C2—N1	1.4873 (16)	C8—H8	1.067 (4)
C2—C3	1.5358 (16)	O13—H13	1.054 (4)
C3—C4	1.4877 (14)	O14—H14	1.031 (3)
C4—N5	1.3849 (16)	O22—H22	1.018 (3)
N5—C6	1.3289 (13)	O23—H23	1.015 (3)
C6—N7	1.3281 (18)	O24—H24	0.998 (3)
O11—P1—O12	113.71 (13)	C1—C2—N1	107.97 (9)
O11—P1—O13	112.10 (12)	C1—C2—C3	110.30 (9)
O11—P1—O14	107.31 (11)	C1—C2—H2	108.68 (18)
O12—P1—O13	106.68 (13)	N1—C2—C3	110.18 (9)
O12—P1—O14	109.11 (14)	N1—C2—H2	108.6 (2)
O13—P1—O14	107.77 (13)	C3—C2—H2	110.99 (19)
P1—O13—H13	123.1 (2)	C2—C3—C4	113.13 (9)
P1—O14—H14	112.0 (2)	C2—C3—H3A	108.3 (2)
O21—P2—O22	114.05 (11)	C2—C3—H3B	108.8 (2)
O21—P2—O23	112.13 (13)	C4—C3—H3A	110.0 (2)
O21—P2—O24	113.40 (14)	C4—C3—H3B	108.94 (18)
O22—P2—O23	105.88 (13)	H3A—C3—H3B	107.5 (3)
O22—P2—O24	102.36 (12)	C3—C4—N5	122.52 (10)
O23—P2—O24	108.28 (13)	C3—C4—C8	131.29 (12)
P2—O22—H22	117.7 (2)	N5—C4—C8	106.18 (9)
P2—O23—H23	111.6 (3)	C4—N5—C6	109.25 (10)
P2—O24—H24	117.6 (2)	C4—N5—H5	123.65 (19)
O1—C1—O2	126.69 (11)	C6—N5—H5	127.0 (2)
O1—C1—C2	116.92 (12)	N5—C6—N7	108.26 (11)
O2—C1—C2	116.39 (11)	N5—C6—H6	126.3 (3)
C2—N1—H1A	112.6 (2)	C6—N7—C8	109.17 (9)
C2—N1—H1B	109.5 (2)	C6—N7—H7	126.1 (2)
C2—N1—H1C	110.3 (2)	C8—N7—H7	124.4 (3)
H1A—N1—H1B	108.6 (3)	C4—C8—N7	107.14 (11)
H1A—N1—H1C	106.8 (3)	C4—C8—H8	131.0 (2)
H1B—N1—H1C	109.0 (3)	N7—C8—H8	121.88 (19)